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Welcome home to this beautifully maintained 3-bedroom, 2-bath home offering comfort, convenience, and exceptional outdoor living. Ideally located just minutes from shopping, schools, the hospital, and other everyday amenities, this home combines a prime location with thoughtful updates. Inside, you'll find two recently remodeled bathrooms featuring modern finished and stylish upgrades. The functional layout provides comfortable living spaces perfect for everyday life. The basement has also been professionally waterproofed, and the existing waterproofing warranty will transfer to the new owner, providing added peace of mind. Step outside to enjoy the fully fenced backyard, offering privacy and plenty of space for children, pets, or entertaining. The extensive hardscaping creates a beautiful, low-maintenance outdoor retreat, while the paver driveway adds outstanding curb appeal. An above-ground pool provides the perfect place to cool off on warm summer days, and the storage shed offers ample space for lawn equipment, tools, and seasonal items. Move-in ready and conveniently located, this home offers the perfect blend of comfort, style. and accessibility. Don't miss your opportunity to make it yours-schedule your private showing today!

153 Fox Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$399,000

Charming 1932 Craftsman Near Downtown Winchester! Step into this classic 1932 Craftsman home, where timeless historic character perfectly meets modern updates. Stunning original craftsman style windows in every room. Boasting an abundance of original woodwork and original wood floors throughout, this home radiates warmth, style, and craftsmanship. The main level highlights Large, open rooms designed for seamless living and entertaining. Bright and open kitchen enjoys newer double ovens, dishwasher, new cooktop and SS hood, new kitchen sink, faucet and new butcher block countertops! The Sunroom features beautiful, heated terracotta tile floors and new double pane windows that flood the space with natural light. Outdoor boasts your classic front porch spanning the width of the house, perfect for relaxing with your favorite beverage. The main floor hosts a 1/2 bath and convenient laundry room. The second level with three generous bedrooms, each equipped with spacious closets, also features a large hall linen closet. The renovated Full Bath comes with custom tile flooring and a sleek, walk-in glass shower. Enjoy the perfect blend of neighborhood charm and urban convenience. If outdoors is your vibe, relaxing on the stone patio with plenty of room for outdoor furniture and a deep, fully fenced yard for kids and pets to enjoy! This home sits just minutes from vibrant downtown restaurants, shopping, and entertainment. Don't miss the opportunity to own a piece of history featuring the perfect balance of original 1930s details and thoughtful modern updates! Call me today to arrange your private showing. PROFESSIONAL PHOTOS COMING SOON.

Charming 1932 Craftsman Near Downtown Winchester! Step into this classic 1932 Craftsman home, where timeless historic character perfectly meets modern updates. Stunning original craftsman style windows in every room. Boasting an abundance of original woodwork and original wood floors throughout, this home radiates warmth, style, and craftsmanship. The main level highlights Large, open rooms designed for seamless living and entertaining. Bright and open kitchen enjoys newer double ovens, dishwasher, new cooktop and SS hood, new kitchen sink, faucet and new butcher block countertops! The Sunroom features beautiful, heated terracotta tile floors and new double pane windows that flood the space with natural light. Outdoor boasts your classic front porch spanning the width of the house, perfect for relaxing with your favorite beverage. The main floor hosts a 1/2 bath and convenient laundry room. The second level with three generous bedrooms, each equipped with spacious closets, also features a large hall linen closet. The renovated Full Bath comes with custom tile flooring and a sleek, walk-in glass shower. Enjoy the perfect blend of neighborhood charm and urban convenience. If outdoors is your vibe, relaxing on the stone patio with plenty of room for outdoor furniture and a deep, fully fenced yard for kids and pets to enjoy! This home sits just minutes from vibrant downtown restaurants, shopping, and entertainment. Don't miss the opportunity to own a piece of history featuring the perfect balance of original 1930s details and thoughtful modern updates! Call me today to arrange your private showing. PROFESSIONAL PHOTOS COMING SOON.

633 Pennsylvania Ave, Winchester

Listing courtesy of Colony Realty. Contact:

$375,000

Lovingly maintained, this charming brick rancher is the perfect starter home or investment opportunity! The main level offers three comfortable bedrooms, one full bath, a bright eat-in kitchen, and a spacious living room filled with natural light. The full unfinished basement provides endless potential for additional finished living space, while an existing hobby room is already in place—perfect for sewing, crafts, a workshop, or a home office. A unique bonus is the custom-built "catio" just off the back of the home, creating a safe outdoor retreat for your feline friends. Outside, enjoy a private backyard with mature landscaping and a detached one-car garage. Ideally located just minutes from Old Town Winchester, the Walking Mall, the Museum of the Shenandoah Valley, Winchester Medical Center, shopping, dining, and commuter routes, this home offers both convenience and charm. Major updates completed in 2016 include new windows, HVAC, roof, driveway, and beautifully refinished hardwood floors. The home is served by public water and a private septic system.

Lovingly maintained, this charming brick rancher is the perfect starter home or investment opportunity! The main level offers three comfortable bedrooms, one full bath, a bright eat-in kitchen, and a spacious living room filled with natural light. The full unfinished basement provides endless potential for additional finished living space, while an existing hobby room is already in place—perfect for sewing, crafts, a workshop, or a home office. A unique bonus is the custom-built "catio" just off the back of the home, creating a safe outdoor retreat for your feline friends. Outside, enjoy a private backyard with mature landscaping and a detached one-car garage. Ideally located just minutes from Old Town Winchester, the Walking Mall, the Museum of the Shenandoah Valley, Winchester Medical Center, shopping, dining, and commuter routes, this home offers both convenience and charm. Major updates completed in 2016 include new windows, HVAC, roof, driveway, and beautifully refinished hardwood floors. The home is served by public water and a private septic system.

805 Pennsylvania Ave, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact: (540) 687-8500

$400,000

Welcome to easy one-level living in Willow Lawn Cottages, a popular 55+ community in Winchester! This well-maintained home has been freshly painted and offers 2 bedrooms and 2 full bathrooms. The open floor plan feels bright and spacious, with vaulted ceilings, plenty of natural light, and luxury vinyl plank flooring throughout. The kitchen includes granite countertops, updated cabinets, stainless steel appliances, and a built-in microwave. The primary bedroom has a walk-in closet and a private bathroom with a walk-in shower. You’ll also find main-level laundry, an attached one-car garage, a covered front porch, and a rear patio where you can relax outdoors. The HOA takes care of lawn maintenance and snow removal and provides access to the community clubhouse, gathering spaces, and sidewalks. Located close to Winchester Medical Center, shopping, restaurants, and historic downtown Winchester, this home offers comfort and convenience in a welcoming community.

2 Beds ⋅ 2 Baths

Welcome to easy one-level living in Willow Lawn Cottages, a popular 55+ community in Winchester! This well-maintained home has been freshly painted and offers 2 bedrooms and 2 full bathrooms. The open floor plan feels bright and spacious, with vaulted ceilings, plenty of natural light, and luxury vinyl plank flooring throughout. The kitchen includes granite countertops, updated cabinets, stainless steel appliances, and a built-in microwave. The primary bedroom has a walk-in closet and a private bathroom with a walk-in shower. You’ll also find main-level laundry, an attached one-car garage, a covered front porch, and a rear patio where you can relax outdoors. The HOA takes care of lawn maintenance and snow removal and provides access to the community clubhouse, gathering spaces, and sidewalks. Located close to Winchester Medical Center, shopping, restaurants, and historic downtown Winchester, this home offers comfort and convenience in a welcoming community.

1853 Rosser Ln, Winchester

Listing courtesy of Realty FC. Contact: (540) 931-0144

$650,000

Welcome to 1529 Dalton Place, an exceptional home tucked away on a quiet cul-de-sac in one of Winchester's most desirable locations. Offering 4 spacious bedrooms, 3.5 bathrooms, and an expansive floor plan, this beautifully designed residence delivers the perfect blend of comfort, style, and functionality. From the moment you enter, you'll appreciate the generous room sizes throughout, including elegant formal living and dining rooms ideal for entertaining. The heart of the home features an inviting open-concept kitchen and family room, creating the perfect space for everyday living and gathering with family and friends. A bright and airy sunroom provides the perfect spot to relax while overlooking the backyard. The finished basement offers exceptional flexibility with abundant space for a recreation room, home theater, fitness area, office, or guest suite. A spacious 2-car garage provides plenty of storage and convenience. Ideally situated in a prime location close to shopping, dining, schools, commuter routes, and all that Winchester has to offer, this impressive home combines space, convenience, and timeless appeal. If you're searching for a move-in-ready home with generous living areas and an unbeatable location, 1529 Dalton Place is one you won't want to miss. All sizes are approximate.

4 Beds ⋅ 4 Baths

Welcome to 1529 Dalton Place, an exceptional home tucked away on a quiet cul-de-sac in one of Winchester's most desirable locations. Offering 4 spacious bedrooms, 3.5 bathrooms, and an expansive floor plan, this beautifully designed residence delivers the perfect blend of comfort, style, and functionality. From the moment you enter, you'll appreciate the generous room sizes throughout, including elegant formal living and dining rooms ideal for entertaining. The heart of the home features an inviting open-concept kitchen and family room, creating the perfect space for everyday living and gathering with family and friends. A bright and airy sunroom provides the perfect spot to relax while overlooking the backyard. The finished basement offers exceptional flexibility with abundant space for a recreation room, home theater, fitness area, office, or guest suite. A spacious 2-car garage provides plenty of storage and convenience. Ideally situated in a prime location close to shopping, dining, schools, commuter routes, and all that Winchester has to offer, this impressive home combines space, convenience, and timeless appeal. If you're searching for a move-in-ready home with generous living areas and an unbeatable location, 1529 Dalton Place is one you won't want to miss. All sizes are approximate.

1529 Dalton Pl, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362

$375,000

Charming, Updated Rancher in the Heart of Winchester! Welcome home to this impeccably maintained 3-bedroom, 2-bath ranch offering the perfect blend of comfort, character, and convenience—all on one level! From the moment you arrive, you'll appreciate the pride of ownership and thoughtful updates throughout. The spacious kitchen is the heart of the home, offering abundant cabinetry and room to gather with family and friends. Multiple living areas provide the flexibility to create a cozy family room, home office, playroom, or hobby space—giving everyone room to spread out. Major updates provide peace of mind, including a new roof, siding, and side porch—all completed within the last year. Other updates include added storage, updated bathrooms, updated flooring, and lots of other touches throughout. Additional features include a gas furnace, central air conditioning, and an abundance of storage rarely found in homes of this size. Located within the City of Winchester, you'll enjoy the convenience of nearby shopping, dining, parks, and commuter routes while coming home to a property filled with warmth, charm, and timeless character. This lovingly cared-for home is a true hidden gem that's move-in ready and waiting for its next owner. Schedule your private tour today before this one is gone!

Charming, Updated Rancher in the Heart of Winchester! Welcome home to this impeccably maintained 3-bedroom, 2-bath ranch offering the perfect blend of comfort, character, and convenience—all on one level! From the moment you arrive, you'll appreciate the pride of ownership and thoughtful updates throughout. The spacious kitchen is the heart of the home, offering abundant cabinetry and room to gather with family and friends. Multiple living areas provide the flexibility to create a cozy family room, home office, playroom, or hobby space—giving everyone room to spread out. Major updates provide peace of mind, including a new roof, siding, and side porch—all completed within the last year. Other updates include added storage, updated bathrooms, updated flooring, and lots of other touches throughout. Additional features include a gas furnace, central air conditioning, and an abundance of storage rarely found in homes of this size. Located within the City of Winchester, you'll enjoy the convenience of nearby shopping, dining, parks, and commuter routes while coming home to a property filled with warmth, charm, and timeless character. This lovingly cared-for home is a true hidden gem that's move-in ready and waiting for its next owner. Schedule your private tour today before this one is gone!

1004 Pennsylvania Ave, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911

$180,000

Opportunity awaits at 309 Liberty Avenue in Winchester City. This classic Cape Cod offers the chance to create something truly special in an area experiencing continued growth, infrastructure improvements, and neighborhood investment. The property does require substantial work, making cash financing the most likely option; however, the potential is significant for a buyer with the vision to transform it into a distinctive home while building meaningful sweat equity. The level backyard provides plenty of usable outdoor space, and the rear alley creates the possibility of adding a gated entrance for convenient off-street parking behind the home. A rare opportunity to reimagine a well-located Winchester property and make it entirely your own.

Opportunity awaits at 309 Liberty Avenue in Winchester City. This classic Cape Cod offers the chance to create something truly special in an area experiencing continued growth, infrastructure improvements, and neighborhood investment. The property does require substantial work, making cash financing the most likely option; however, the potential is significant for a buyer with the vision to transform it into a distinctive home while building meaningful sweat equity. The level backyard provides plenty of usable outdoor space, and the rear alley creates the possibility of adding a gated entrance for convenient off-street parking behind the home. A rare opportunity to reimagine a well-located Winchester property and make it entirely your own.

309 Liberty Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099

$719,000

Situated on a prominent corner lot in an exclusive cul-de-sac enclave of distinguished homes, this impressive stone-front residence offers exceptional space, comfort, and timeless appeal in one of the area’s most desirable neighborhoods. Ideally located near fine dining, shopping, banks, and everyday conveniences, the home combines luxury living with unmatched accessibility. Built in 2011 and meticulously maintained, freshly painted, with new wall to wall carpet, this expansive residence features 7 bedrooms and 5 full bathrooms thoughtfully designed for both elegant entertaining and comfortable everyday living. A dramatic two-story foyer creates a grand first impression, flanked by formal living and dining rooms that add sophistication and charm. The upper level includes a luxurious owner’s suite with a spacious bedroom and spa-inspired bath, along with generously sized secondary bedrooms, including a Jack-and-Jill bath and an additional hall bath arrangement designed for convenience and privacy. The main level offers a desirable guest suite with a full bath, ideal for multigenerational living or visiting guests. At the heart of the home is a beautifully appointed gourmet kitchen featuring upgraded cabinetry, granite countertops, a center island, breakfast area, and seamless flow into the expansive family room. The finished lower level provides exceptional versatility with a large recreation/family room, an additional suite, and three flexible rooms perfectly suited for guest accommodations, home offices, fitness space, or playrooms. Step outside to the inviting deck overlooking the gently rolling backyard — an ideal setting for relaxing mornings, outdoor dining, and entertaining in a peaceful, private setting. House blueprints provided in this listing are for reference only and may not accurately reflect the current structure. Call your real estate agent and schedule a showing today!

7 Beds ⋅ 5 Baths

Situated on a prominent corner lot in an exclusive cul-de-sac enclave of distinguished homes, this impressive stone-front residence offers exceptional space, comfort, and timeless appeal in one of the area’s most desirable neighborhoods. Ideally located near fine dining, shopping, banks, and everyday conveniences, the home combines luxury living with unmatched accessibility. Built in 2011 and meticulously maintained, freshly painted, with new wall to wall carpet, this expansive residence features 7 bedrooms and 5 full bathrooms thoughtfully designed for both elegant entertaining and comfortable everyday living. A dramatic two-story foyer creates a grand first impression, flanked by formal living and dining rooms that add sophistication and charm. The upper level includes a luxurious owner’s suite with a spacious bedroom and spa-inspired bath, along with generously sized secondary bedrooms, including a Jack-and-Jill bath and an additional hall bath arrangement designed for convenience and privacy. The main level offers a desirable guest suite with a full bath, ideal for multigenerational living or visiting guests. At the heart of the home is a beautifully appointed gourmet kitchen featuring upgraded cabinetry, granite countertops, a center island, breakfast area, and seamless flow into the expansive family room. The finished lower level provides exceptional versatility with a large recreation/family room, an additional suite, and three flexible rooms perfectly suited for guest accommodations, home offices, fitness space, or playrooms. Step outside to the inviting deck overlooking the gently rolling backyard — an ideal setting for relaxing mornings, outdoor dining, and entertaining in a peaceful, private setting. House blueprints provided in this listing are for reference only and may not accurately reflect the current structure. Call your real estate agent and schedule a showing today!

2700 Loyalty Ct, Winchester

Listing courtesy of Elcy & Co. Realty, LLC.. Contact: 5403230675

$429,000

Turn-key and move-in ready! This beautifully updated 4-bedroom, 2-bath home features a modern kitchen with recently updated appliances, a new HVAC system, and a new hot water heater for added peace of mind. Enjoy the spacious backyard, perfect for outdoor entertaining, along with convenient off-street parking and the freedom of no HOA. Nestled in an established neighborhood with large yards and a charming community park, this home is ideally located just minutes from Winchester Medical Center, the Museum of the Shenandoah Valley, and Old Town Winchester's restaurants, shops, and entertainment.

4 Beds ⋅ 2 Baths

Turn-key and move-in ready! This beautifully updated 4-bedroom, 2-bath home features a modern kitchen with recently updated appliances, a new HVAC system, and a new hot water heater for added peace of mind. Enjoy the spacious backyard, perfect for outdoor entertaining, along with convenient off-street parking and the freedom of no HOA. Nestled in an established neighborhood with large yards and a charming community park, this home is ideally located just minutes from Winchester Medical Center, the Museum of the Shenandoah Valley, and Old Town Winchester's restaurants, shops, and entertainment.

1310 Whittier Ave, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475

$500,900

Welcome to 609 Quartzite Circle! A beautifully maintained 4-bedroom, 3-bath home offering a spacious and functional layout designed for modern living. The main level features inviting living spaces, hardwood flooring, and an open kitchen with ample cabinetry and table space. The primary suite includes a walk-in closet and a private bath with a soaking tub, while the finished lower level provides a generous recreation room, an additional bedroom, and a full bath, offering flexible space for guests, a home office, or everyday living. Enjoy the fully fenced backyard with a patio, perfect for relaxing or entertaining, along with the convenience of an attached 2-car garage. Ideally located near shopping, dining, schools, parks, and major commuter routes, this home combines comfort, versatility, and a convenient Winchester location.

Welcome to 609 Quartzite Circle! A beautifully maintained 4-bedroom, 3-bath home offering a spacious and functional layout designed for modern living. The main level features inviting living spaces, hardwood flooring, and an open kitchen with ample cabinetry and table space. The primary suite includes a walk-in closet and a private bath with a soaking tub, while the finished lower level provides a generous recreation room, an additional bedroom, and a full bath, offering flexible space for guests, a home office, or everyday living. Enjoy the fully fenced backyard with a patio, perfect for relaxing or entertaining, along with the convenience of an attached 2-car garage. Ideally located near shopping, dining, schools, parks, and major commuter routes, this home combines comfort, versatility, and a convenient Winchester location.

609 Quartzite Cir, Winchester

Listing courtesy of Samson Properties. Contact: 7033788810

$360,000

Welcome home to 117 E Pall Mall St! Ideally located within a mile of Shenandoah University and historic downtown Winchester! This 3 bedroom, 2.5 bath has lots of updates and upgrades! Updated kitchen and baths, stainless steel appliances, & a fenced in backyard! 2023 - Roof, siding, & electrical panel (and all breakers), updated kitchen and all baths, 2024 - repaired sump pump & new hot water heater, 2025 - new sewer line under driveway & from driveway to street, new LVP in kitchen, 2026 - replaced / leveled living room floor & subfloor, new LVP. Schedule your tour today!

3 Beds ⋅ 3 Baths

Welcome home to 117 E Pall Mall St! Ideally located within a mile of Shenandoah University and historic downtown Winchester! This 3 bedroom, 2.5 bath has lots of updates and upgrades! Updated kitchen and baths, stainless steel appliances, & a fenced in backyard! 2023 - Roof, siding, & electrical panel (and all breakers), updated kitchen and all baths, 2024 - repaired sump pump & new hot water heater, 2025 - new sewer line under driveway & from driveway to street, new LVP in kitchen, 2026 - replaced / leveled living room floor & subfloor, new LVP. Schedule your tour today!

117 E Pall Mall St, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com

$449,000

Discover the perfect blend of historic charm and modern convenience at 420 W Cork Street. This captivating four-level brick home offers 4 bedrooms and 1.5 baths, boasting beautiful hardwood floors, gorgeous trim and plenty of space for you and yours. The main level offers a spacious living room, dining room and kitchen. Upstairs you will find 4 sizable bedrooms and a full bath. The top level is a true gem—a finished attic with an exposed brick wall, providing a unique, flexible space ideal for a home office, a creative studio, or a quiet retreat. Step outside and discover the large covered front porch. Adorned with a stylish wooden ceiling, it's the perfect spot to relax and enjoy the neighborhood. The rear deck and fully-fenced backyard offer a private oasis for outdoor gatherings. Situated on a desirable corner lot, the home's prime location puts you just moments away from Winchester's best shopping, dining, and schools. Parking is a breeze with a detached garage and a private driveway, providing abundant off-street parking—a valuable convenience in this downtown neighborhood. Offering recently updated HVAC on 3 levels.

4 Beds ⋅ 2 Baths

Discover the perfect blend of historic charm and modern convenience at 420 W Cork Street. This captivating four-level brick home offers 4 bedrooms and 1.5 baths, boasting beautiful hardwood floors, gorgeous trim and plenty of space for you and yours. The main level offers a spacious living room, dining room and kitchen. Upstairs you will find 4 sizable bedrooms and a full bath. The top level is a true gem—a finished attic with an exposed brick wall, providing a unique, flexible space ideal for a home office, a creative studio, or a quiet retreat. Step outside and discover the large covered front porch. Adorned with a stylish wooden ceiling, it's the perfect spot to relax and enjoy the neighborhood. The rear deck and fully-fenced backyard offer a private oasis for outdoor gatherings. Situated on a desirable corner lot, the home's prime location puts you just moments away from Winchester's best shopping, dining, and schools. Parking is a breeze with a detached garage and a private driveway, providing abundant off-street parking—a valuable convenience in this downtown neighborhood. Offering recently updated HVAC on 3 levels.

420 W Cork St, Winchester

Listing courtesy of Colony Realty. Contact:

$295,000

1314 S Braddock St is a one-story Winchester single-family home with a functional single-level layout. The kitchen is equipped with stainless steel appliances for everyday cooking and cleanup. The bathroom includes a tub and shower for daily use, and a dedicated laundry area with a stacked washer and dryer keeps utility tasks out of the main living space. Multiple bedrooms provide flexible room for sleeping or work-from-home use. Outdoors, a covered front porch offers a shaded sitting area, a rear deck extends the usable outdoor space, and a fully fenced backyard defines the grounds for outdoor activities. Clean interior finishes complete this well-maintained residence with practical amenities throughout every room.. Included 100-Day Home Warranty with buyer activation

1314 S Braddock St is a one-story Winchester single-family home with a functional single-level layout. The kitchen is equipped with stainless steel appliances for everyday cooking and cleanup. The bathroom includes a tub and shower for daily use, and a dedicated laundry area with a stacked washer and dryer keeps utility tasks out of the main living space. Multiple bedrooms provide flexible room for sleeping or work-from-home use. Outdoors, a covered front porch offers a shaded sitting area, a rear deck extends the usable outdoor space, and a fully fenced backyard defines the grounds for outdoor activities. Clean interior finishes complete this well-maintained residence with practical amenities throughout every room.. Included 100-Day Home Warranty with buyer activation

1314 S Braddock St, Winchester

Listing courtesy of Open Door Brokerage, LLC. Contact: 4804625392

$435,000

Come home to Whittier Acres and this well maintained Rancher with 1-car garage just minutes from Winchester Medical Center. You'll love the cozy living room with wood burning fireplace, crown molding & built in bookshelves. Gleaming hardwood floors grace the main level (just refinished). The kitchen has a French door refrigerator, electric range, built-in microwave, dishwasher, a built-in spice rack & a tile backsplash. The primary suite includes a remodeled primary bath (2023). There is a cozy sun porch on the rear of the home. Enjoy your morning coffee on the inviting front porch or out on the rear deck. The partially finished basement offers a large recreation room with wood stove for all your favorite hobbies. There is also a spacious storage room for your holiday decor, etc. The fenced backyard has a fire pit perfect for cooler fall evenings. There is also a shed for storing your gardening tools.

Come home to Whittier Acres and this well maintained Rancher with 1-car garage just minutes from Winchester Medical Center. You'll love the cozy living room with wood burning fireplace, crown molding & built in bookshelves. Gleaming hardwood floors grace the main level (just refinished). The kitchen has a French door refrigerator, electric range, built-in microwave, dishwasher, a built-in spice rack & a tile backsplash. The primary suite includes a remodeled primary bath (2023). There is a cozy sun porch on the rear of the home. Enjoy your morning coffee on the inviting front porch or out on the rear deck. The partially finished basement offers a large recreation room with wood stove for all your favorite hobbies. There is also a spacious storage room for your holiday decor, etc. The fenced backyard has a fire pit perfect for cooler fall evenings. There is also a shed for storing your gardening tools.

338 Lanny Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$600,000

Nestled in the charming City of Winchester, this delightful Colonial home, built in 1952, exudes warmth and character. With its classic brick exterior and excellent condition, this residence invites you to experience a blend of traditional elegance and modern comfort. Step inside to discover a thoughtfully designed interior featuring beautiful hardwood floors that flow seamlessly throughout. The home spans approximately 3,480 square feet (1,844 main living areas + 804 sunroom + 832 basement). The traditional floor plan offers a formal dining room, perfect for hosting gatherings, while the butler's pantry adds a touch of convenience for entertaining. The kitchen is equipped with upgraded countertops and modern appliances, including a built-in microwave, cooktop, range hood, wall oven, dishwasher, and refrigerator, making meal preparation a joy. The home boasts three well-appointed bedrooms, each with ample closet space, including a walk-in closet in the master suite. The bathrooms are designed for comfort, featuring a full bath with a tub shower and a convenient half bath for guests. The property also includes a connecting stairway to the basement, where you'll find additional storage and laundry facilities. Outside, the extensive hardscape provides a relaxing outdoor space, perfect for enjoying the fresh air or hosting outdoor gatherings. A shed offers extra storage options for gardening tools or recreational equipment. Living in this vibrant community means enjoying the benefits of nearby parks, schools, and public services. The City of Winchester is known for its friendly atmosphere and active community life, with local events and activities that foster a sense of belonging. With on-street parking and a location that offers easy access to local amenities, this home is a perfect blend of comfort, style, and community spirit. Experience the charm of this Colonial residence and make it your own, where every corner feels like home. (See documents for improvements list)

Nestled in the charming City of Winchester, this delightful Colonial home, built in 1952, exudes warmth and character. With its classic brick exterior and excellent condition, this residence invites you to experience a blend of traditional elegance and modern comfort. Step inside to discover a thoughtfully designed interior featuring beautiful hardwood floors that flow seamlessly throughout. The home spans approximately 3,480 square feet (1,844 main living areas + 804 sunroom + 832 basement). The traditional floor plan offers a formal dining room, perfect for hosting gatherings, while the butler's pantry adds a touch of convenience for entertaining. The kitchen is equipped with upgraded countertops and modern appliances, including a built-in microwave, cooktop, range hood, wall oven, dishwasher, and refrigerator, making meal preparation a joy. The home boasts three well-appointed bedrooms, each with ample closet space, including a walk-in closet in the master suite. The bathrooms are designed for comfort, featuring a full bath with a tub shower and a convenient half bath for guests. The property also includes a connecting stairway to the basement, where you'll find additional storage and laundry facilities. Outside, the extensive hardscape provides a relaxing outdoor space, perfect for enjoying the fresh air or hosting outdoor gatherings. A shed offers extra storage options for gardening tools or recreational equipment. Living in this vibrant community means enjoying the benefits of nearby parks, schools, and public services. The City of Winchester is known for its friendly atmosphere and active community life, with local events and activities that foster a sense of belonging. With on-street parking and a location that offers easy access to local amenities, this home is a perfect blend of comfort, style, and community spirit. Experience the charm of this Colonial residence and make it your own, where every corner feels like home. (See documents for improvements list)

1311 Handley Ave, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$435,000

Seller offering closing cost assistance on select offers—contact the listing agent for details. Welcome to this beautifully renovated historic home in the heart of Old Town Winchester, where timeless charm meets modern living. This move-in-ready 4-bedroom, 2-bath home has been thoughtfully updated throughout, featuring a stunning kitchen with quartz countertops, custom cabinetry, stainless steel appliances, and designer finishes. Enjoy new flooring, fresh paint, updated lighting, and renovated bathrooms. Outside, relax on the inviting covered front porch or entertain on the rear patio overlooking the spacious fenced backyard. Just minutes away from the Winchester Walking Mall, restaurants, shopping, breweries, parks, and local events, this turnkey home offers the perfect blend of historic character, modern updates, and an unbeatable location. Schedule your private tour today!

4 Beds ⋅ 2 Baths

Seller offering closing cost assistance on select offers—contact the listing agent for details. Welcome to this beautifully renovated historic home in the heart of Old Town Winchester, where timeless charm meets modern living. This move-in-ready 4-bedroom, 2-bath home has been thoughtfully updated throughout, featuring a stunning kitchen with quartz countertops, custom cabinetry, stainless steel appliances, and designer finishes. Enjoy new flooring, fresh paint, updated lighting, and renovated bathrooms. Outside, relax on the inviting covered front porch or entertain on the rear patio overlooking the spacious fenced backyard. Just minutes away from the Winchester Walking Mall, restaurants, shopping, breweries, parks, and local events, this turnkey home offers the perfect blend of historic character, modern updates, and an unbeatable location. Schedule your private tour today!

21 E Germain St, Winchester

Listing courtesy of Samson Properties. Contact: 7033788810

$420,000

Welcome to 1826 Kershaw Lane in Willow Lawn Cottages, one of Winchester, Virginia's most sought-after 55+ active adult communities, offering low-maintenance, single-level living just minutes from Historic Old Town Winchester. This beautifully maintained 2-bedroom, 2-bath ranch home showcases exceptional pride of ownership with beautiful hardwood flooring, soaring vaulted ceilings, and an open floor plan filled with natural light. The kitchen features a decorative ceramic tile backsplash, an updated Moen faucet, a new refrigerator, and a new microwave, combining style and functionality for the home chef. The spacious primary suite offers a relaxing retreat with a private en-suite bath and generous closet space. A second bedroom and full bathroom provide comfortable accommodations for family and guests. The inviting sunroom is bathed in natural light, creating the perfect space for morning coffee, reading, hobbies, or a home office. Additional updates include new gas fireplace logs, adding warmth and charm to the living area. Outside, you'll enjoy a beautifully landscaped garden that creates a peaceful setting for relaxing or entertaining. French drains have also been installed to enhance drainage and provide added peace of mind. Residents of Willow Lawn Cottages enjoy a friendly community atmosphere with convenient access to Historic Old Town Winchester, Shenandoah University, Winchester Medical Center, Jim Barnett Park, the Museum of the Shenandoah Valley, and the Winchester Green Circle Trail. Shopping, dining, healthcare, and year-round events are just minutes away.

2 Beds ⋅ 2 Baths

Welcome to 1826 Kershaw Lane in Willow Lawn Cottages, one of Winchester, Virginia's most sought-after 55+ active adult communities, offering low-maintenance, single-level living just minutes from Historic Old Town Winchester. This beautifully maintained 2-bedroom, 2-bath ranch home showcases exceptional pride of ownership with beautiful hardwood flooring, soaring vaulted ceilings, and an open floor plan filled with natural light. The kitchen features a decorative ceramic tile backsplash, an updated Moen faucet, a new refrigerator, and a new microwave, combining style and functionality for the home chef. The spacious primary suite offers a relaxing retreat with a private en-suite bath and generous closet space. A second bedroom and full bathroom provide comfortable accommodations for family and guests. The inviting sunroom is bathed in natural light, creating the perfect space for morning coffee, reading, hobbies, or a home office. Additional updates include new gas fireplace logs, adding warmth and charm to the living area. Outside, you'll enjoy a beautifully landscaped garden that creates a peaceful setting for relaxing or entertaining. French drains have also been installed to enhance drainage and provide added peace of mind. Residents of Willow Lawn Cottages enjoy a friendly community atmosphere with convenient access to Historic Old Town Winchester, Shenandoah University, Winchester Medical Center, Jim Barnett Park, the Museum of the Shenandoah Valley, and the Winchester Green Circle Trail. Shopping, dining, healthcare, and year-round events are just minutes away.

1826 Kershaw Ln, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362

$569,000

Exceptional opportunity to own this beautifully crafted custom all-brick home on Winchester's desirable east side, nestled in an established neighborhood just minutes from Route 7, downtown Winchester, schools, shopping, dining, hospitals, and major commuter routes. Designed for both everyday living and entertaining, this impressive residence features an open-concept floor plan with gleaming hardwood floors, abundant natural light, custom built-ins, and a cozy gas fireplace. The contemporary gourmet kitchen showcases granite countertops, stainless steel appliances, a spacious pantry, and a generous breakfast area, flowing seamlessly into the Large dining and living spaces. The thoughtfully designed layout offers four spacious bedrooms, each with access to a full bathroom. On the main level, you'll find a welcoming guest bedroom with a nearby full bath, along with the luxurious primary suite featuring a private ensuite bath with a tub/shower combination and walk-in closet. A convenient laundry room with utility sink is located just off the kitchen and provides access to a covered carport and outdoor sitting area. A private upper-level suite includes its own entrance on main level with a connected living room, two upper level bedrooms, and full bath, and sitting area making it ideal for an in-law suite, au pair quarters, or private guest accommodations. Adding even more versatility, the detached two-car garage is topped by a fully equipped apartment complete with a bedroom, full bath, and kitchen/living area—perfect for rental income, multigenerational living, a home office, or long-term guests. Parking is abundant with front and rear driveways, the detached two-car garage, and additional street parking. Combining timeless craftsmanship, flexible living spaces, income-producing potential, and an unbeatable location, this one-of-a-kind property truly offers something for everyone. Don't miss the opportunity to make this exceptional home yours!

4 Beds ⋅ 4 Baths

Exceptional opportunity to own this beautifully crafted custom all-brick home on Winchester's desirable east side, nestled in an established neighborhood just minutes from Route 7, downtown Winchester, schools, shopping, dining, hospitals, and major commuter routes. Designed for both everyday living and entertaining, this impressive residence features an open-concept floor plan with gleaming hardwood floors, abundant natural light, custom built-ins, and a cozy gas fireplace. The contemporary gourmet kitchen showcases granite countertops, stainless steel appliances, a spacious pantry, and a generous breakfast area, flowing seamlessly into the Large dining and living spaces. The thoughtfully designed layout offers four spacious bedrooms, each with access to a full bathroom. On the main level, you'll find a welcoming guest bedroom with a nearby full bath, along with the luxurious primary suite featuring a private ensuite bath with a tub/shower combination and walk-in closet. A convenient laundry room with utility sink is located just off the kitchen and provides access to a covered carport and outdoor sitting area. A private upper-level suite includes its own entrance on main level with a connected living room, two upper level bedrooms, and full bath, and sitting area making it ideal for an in-law suite, au pair quarters, or private guest accommodations. Adding even more versatility, the detached two-car garage is topped by a fully equipped apartment complete with a bedroom, full bath, and kitchen/living area—perfect for rental income, multigenerational living, a home office, or long-term guests. Parking is abundant with front and rear driveways, the detached two-car garage, and additional street parking. Combining timeless craftsmanship, flexible living spaces, income-producing potential, and an unbeatable location, this one-of-a-kind property truly offers something for everyone. Don't miss the opportunity to make this exceptional home yours!

687 Woodland Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099

$3,175,000

A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city limits. Perfectly positioned on 5.49 acres of breathtaking, park-like grounds, this historic masterpiece is a true private oasis. Painstakingly and lovingly renovated, the estate offers an unparalleled blend of 18th-century charm and contemporary convenience across 8,593 finished square feet, featuring 6 bedrooms, 5 full baths, and 2 half baths. The heart of the residence is the original 1765 portion, which stands as a museum-quality testament to early American craftsmanship. It showcases meticulously preserved original flooring, windows, doors, period hardware, stately mantles, and staircase. As the estate evolved, a first major addition was seamlessly introduced in 1940, followed by a second grand addition in 2000. True to the property's legacy of excellence, the 1940 wing underwent a major, high-end renovation in 2019 to ensure flawless modern style. Yet, behind the historic craftsmanship lies a completely modernized infrastructure: the entire home boasts fully updated plumbing, electrical, and central heating and A/C. Step outside to find your own secluded sanctuary, complete with a natural spring and a picturesque pond. This is a living piece of art, offering the perfect synergy of historical beauty, absolute privacy, and contemporary convenience. For additional information, full ownership history starting in 1735 and comprehensive renovation highlights please view the accompanying documents. Schedule your private tour to experience this once-in-a-lifetime legacy property. See accompanying files for full Historical Lineage starting in 1735, and details about the architecture and features.

6 Beds ⋅ 7 Baths

A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city limits. Perfectly positioned on 5.49 acres of breathtaking, park-like grounds, this historic masterpiece is a true private oasis. Painstakingly and lovingly renovated, the estate offers an unparalleled blend of 18th-century charm and contemporary convenience across 8,593 finished square feet, featuring 6 bedrooms, 5 full baths, and 2 half baths. The heart of the residence is the original 1765 portion, which stands as a museum-quality testament to early American craftsmanship. It showcases meticulously preserved original flooring, windows, doors, period hardware, stately mantles, and staircase. As the estate evolved, a first major addition was seamlessly introduced in 1940, followed by a second grand addition in 2000. True to the property's legacy of excellence, the 1940 wing underwent a major, high-end renovation in 2019 to ensure flawless modern style. Yet, behind the historic craftsmanship lies a completely modernized infrastructure: the entire home boasts fully updated plumbing, electrical, and central heating and A/C. Step outside to find your own secluded sanctuary, complete with a natural spring and a picturesque pond. This is a living piece of art, offering the perfect synergy of historical beauty, absolute privacy, and contemporary convenience. For additional information, full ownership history starting in 1735 and comprehensive renovation highlights please view the accompanying documents. Schedule your private tour to experience this once-in-a-lifetime legacy property. See accompanying files for full Historical Lineage starting in 1735, and details about the architecture and features.

730 Merrimans Ln, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$530,000

Welcome to this charming historic home in Old Town. A spacious 3-bedroom Colonial, where timeless character meets modern comfort in the heart of Winchester. Thoughtfully updated with today's buyer in mind, this charming residence offers upgraded amenities while preserving its classic appeal. Inside, you'll find generous living spaces filled with natural light, along with a walk-up attic offering abundant storage or future expansion potential. The full basement is ready to be finished, providing the perfect opportunity to create additional living space, a home gym, recreation room, or workshop. Outside, the detached garage offers exceptional versatility for parking, storage, hobbies, or a workshop. Ideally situated just minutes from the heart of historic Old Town Winchester, you'll enjoy the convenience of walking to local restaurants, boutique shopping, entertainment, the Shenandoah Valley Museum, and Valley Health Winchester Medical Center. Whether you're looking for a primary residence or an investment in one of Winchester's most desirable locations, this move-in-ready home offers the perfect combination of historic charm, modern updates, and unbeatable convenience.

Welcome to this charming historic home in Old Town. A spacious 3-bedroom Colonial, where timeless character meets modern comfort in the heart of Winchester. Thoughtfully updated with today's buyer in mind, this charming residence offers upgraded amenities while preserving its classic appeal. Inside, you'll find generous living spaces filled with natural light, along with a walk-up attic offering abundant storage or future expansion potential. The full basement is ready to be finished, providing the perfect opportunity to create additional living space, a home gym, recreation room, or workshop. Outside, the detached garage offers exceptional versatility for parking, storage, hobbies, or a workshop. Ideally situated just minutes from the heart of historic Old Town Winchester, you'll enjoy the convenience of walking to local restaurants, boutique shopping, entertainment, the Shenandoah Valley Museum, and Valley Health Winchester Medical Center. Whether you're looking for a primary residence or an investment in one of Winchester's most desirable locations, this move-in-ready home offers the perfect combination of historic charm, modern updates, and unbeatable convenience.

108 Morgan St, Winchester

Listing courtesy of Real Broker LLC- Winchester. Contact:

$285,000

Classic charm in this brick Cape Cod located in Winchester City, just minutes from shopping, dining, and commuter routes. Set in a sidewalk-lined neighborhood, this home is full of character with arched doorways, hardwood floors throughout, and a wood-burning fireplace that creates a warm focal point in the living room. The kitchen features white cabinetry, stainless steel appliances, and granite countertops, offering both style and functionality. A bright sunroom provides additional living space overlooking the backyard, while the deck is perfect for relaxing or entertaining outdoors. A detached one-car garage in the backyard adds convenient parking and extra storage, making this home an exceptional opportunity.

Classic charm in this brick Cape Cod located in Winchester City, just minutes from shopping, dining, and commuter routes. Set in a sidewalk-lined neighborhood, this home is full of character with arched doorways, hardwood floors throughout, and a wood-burning fireplace that creates a warm focal point in the living room. The kitchen features white cabinetry, stainless steel appliances, and granite countertops, offering both style and functionality. A bright sunroom provides additional living space overlooking the backyard, while the deck is perfect for relaxing or entertaining outdoors. A detached one-car garage in the backyard adds convenient parking and extra storage, making this home an exceptional opportunity.

304 Shenandoah Ave, Winchester

Listing courtesy of Re/Max Roots. Contact: (540) 686-7362

$330,000

Welcome to 101 Locust Avenue in the heart of Winchester on a spacious corner lot! This solid brick ranch home offers 3 bedrooms, 2.5 bathrooms, and comfortable one-level living with additional space in the lower level. The bright and spacious living room serves as the centerpiece of the home, featuring a large bay window that fills the space with natural light. On the main level there are three bedrooms, a full bath, and a convenient half bath. The lower level offers interior access and includes a finished room and full bathroom, providing flexible space for a home office, recreation room, hobby area, or additional living space, while the unfinished portion offers excellent storage potential. Outside, enjoy a fully fenced backyard and a covered carport for one vehicle on a spacious lot. Recent updates include a freshly painted interior completed in June 2026 and the addition of a full bathroom in the lower level in 2022/2023 Ideally located with easy access to I-81, this property is approximately 10 minutes from Shenandoah University and just minutes from shopping, dining, and other everyday conveniences. Successfully maintained as a rental property for the past four years, this home presents an excellent opportunity for both owners and investors seeking a well-cared-for property in a convenient location.

3 Beds ⋅ 3 Baths

Welcome to 101 Locust Avenue in the heart of Winchester on a spacious corner lot! This solid brick ranch home offers 3 bedrooms, 2.5 bathrooms, and comfortable one-level living with additional space in the lower level. The bright and spacious living room serves as the centerpiece of the home, featuring a large bay window that fills the space with natural light. On the main level there are three bedrooms, a full bath, and a convenient half bath. The lower level offers interior access and includes a finished room and full bathroom, providing flexible space for a home office, recreation room, hobby area, or additional living space, while the unfinished portion offers excellent storage potential. Outside, enjoy a fully fenced backyard and a covered carport for one vehicle on a spacious lot. Recent updates include a freshly painted interior completed in June 2026 and the addition of a full bathroom in the lower level in 2022/2023 Ideally located with easy access to I-81, this property is approximately 10 minutes from Shenandoah University and just minutes from shopping, dining, and other everyday conveniences. Successfully maintained as a rental property for the past four years, this home presents an excellent opportunity for both owners and investors seeking a well-cared-for property in a convenient location.

101 Locust Ave, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$325,000

Priced to sell! A true Federal‑style gem, this solid brick home offers the chance to restore a piece of architectural history. Rich with original craftsmanship, it features high ceilings, original hardwood floors, solid wood doors and trim, and a beautiful covered front porch—timeless details that showcase the home’s enduring character. Designed with good bones and a layout that adapts to many visions, this property is the ideal project for someone ready to create something extraordinary. The home was once configured with an upper‑level apartment, complete with a private entrance, back stairway, and space for a second kitchen and bath—perfect for multi‑generational living, rental income, or reimagining the entire second floor into a spacious primary suite. Updated vinyl, energy‑efficient windows and a durable metal roof provide a strong start for renovation. A walk‑up attic offers excellent storage and the potential to be finished for additional living space. The upper level could accommodate three full bathrooms, allowing for a highly functional and modern second floor once renovated. An unfinished basement with both interior access and a walk‑up exit is even more space for storage. New electrical and plumbing updates are needed giving the next owner the opportunity to modernize the home exactly to their taste. With its architectural pedigree, adaptable layout, and solid structural foundation, this property is a rare chance to bring a historic home back to life and create something truly special.

Priced to sell! A true Federal‑style gem, this solid brick home offers the chance to restore a piece of architectural history. Rich with original craftsmanship, it features high ceilings, original hardwood floors, solid wood doors and trim, and a beautiful covered front porch—timeless details that showcase the home’s enduring character. Designed with good bones and a layout that adapts to many visions, this property is the ideal project for someone ready to create something extraordinary. The home was once configured with an upper‑level apartment, complete with a private entrance, back stairway, and space for a second kitchen and bath—perfect for multi‑generational living, rental income, or reimagining the entire second floor into a spacious primary suite. Updated vinyl, energy‑efficient windows and a durable metal roof provide a strong start for renovation. A walk‑up attic offers excellent storage and the potential to be finished for additional living space. The upper level could accommodate three full bathrooms, allowing for a highly functional and modern second floor once renovated. An unfinished basement with both interior access and a walk‑up exit is even more space for storage. New electrical and plumbing updates are needed giving the next owner the opportunity to modernize the home exactly to their taste. With its architectural pedigree, adaptable layout, and solid structural foundation, this property is a rare chance to bring a historic home back to life and create something truly special.

719 National Ave, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

$899,000

Your long search is over! Beautifully renovated all-brick ranch home situated on a secluded 2.03-acre lot in the city of Winchester, just a short walk to Valley Health. Offering an exceptional combination of privacy, convenience, and quality. This home features spacious living areas, three fireplaces, including one in the primary bedroom. The finished lower level provides outstanding flexibility with a large rec room, full kitchen, and full bath-ideas for guests, extended family, or entertaining. Outdoor living is a grand feature, with multiple brick patios and private spaces designed to take full advantage of the tranquil park setting. The property also has a unique barn for storage or a workshop. Recent improvements include a newer metal roof, while the expansive lot offers a rare sense of seclusion within the City limits. A truly unique property that combines timeless all-brick construction, modern renovations, and an unbeatable location near medical facilities, shopping, dining, downtown Winchester, and the Museum of the Shenandoah Valley.

3 Beds ⋅ 4 Baths

Your long search is over! Beautifully renovated all-brick ranch home situated on a secluded 2.03-acre lot in the city of Winchester, just a short walk to Valley Health. Offering an exceptional combination of privacy, convenience, and quality. This home features spacious living areas, three fireplaces, including one in the primary bedroom. The finished lower level provides outstanding flexibility with a large rec room, full kitchen, and full bath-ideas for guests, extended family, or entertaining. Outdoor living is a grand feature, with multiple brick patios and private spaces designed to take full advantage of the tranquil park setting. The property also has a unique barn for storage or a workshop. Recent improvements include a newer metal roof, while the expansive lot offers a rare sense of seclusion within the City limits. A truly unique property that combines timeless all-brick construction, modern renovations, and an unbeatable location near medical facilities, shopping, dining, downtown Winchester, and the Museum of the Shenandoah Valley.

466 Merrimans Ln, Winchester

Listing courtesy of Colony Realty. Contact:

$539,000

Nestled on one of Winchester's most sought-after streets, this distinctive mid-century contemporary home offers a rare blend of character, space, and convenience just moments from downtown dining, shopping, and entertainment. Designed for comfortable main-level living, the home combines timeless architectural appeal with thoughtful functionality. The main level features a spacious primary suite with an expansive walk-in closet and private en-suite bath. The bright and inviting living room flows seamlessly into the kitchen, complete with granite countertops, abundant cabinetry, and a charming pass-through to the separate dining area. Just off the kitchen, you'll find a conveniently located laundry area with additional cabinetry and countertop workspace. Step outside to a private patio, perfect for entertaining or relaxing after an evening downtown. A fenced side yard provides additional outdoor space for pets, gardening, or play. Upstairs, an open loft creates the perfect reading nook, home office, or cozy sitting area, alongside two additional bedrooms and a full bath. The expansive partially finished basement provides exceptional flexibility, featuring a bonus room, full bathroom, second laundry area, and abundant storage, with plenty of room for future customization. Combining architectural character, flexible living spaces, and an exceptional location, this home presents a unique opportunity in the heart of Winchester.

3 Beds ⋅ 4 Baths

Nestled on one of Winchester's most sought-after streets, this distinctive mid-century contemporary home offers a rare blend of character, space, and convenience just moments from downtown dining, shopping, and entertainment. Designed for comfortable main-level living, the home combines timeless architectural appeal with thoughtful functionality. The main level features a spacious primary suite with an expansive walk-in closet and private en-suite bath. The bright and inviting living room flows seamlessly into the kitchen, complete with granite countertops, abundant cabinetry, and a charming pass-through to the separate dining area. Just off the kitchen, you'll find a conveniently located laundry area with additional cabinetry and countertop workspace. Step outside to a private patio, perfect for entertaining or relaxing after an evening downtown. A fenced side yard provides additional outdoor space for pets, gardening, or play. Upstairs, an open loft creates the perfect reading nook, home office, or cozy sitting area, alongside two additional bedrooms and a full bath. The expansive partially finished basement provides exceptional flexibility, featuring a bonus room, full bathroom, second laundry area, and abundant storage, with plenty of room for future customization. Combining architectural character, flexible living spaces, and an exceptional location, this home presents a unique opportunity in the heart of Winchester.

1202 Handley Ave, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475

$545,000

Nestled in the established Cedarmeade community, this beautifully updated 4-bedroom, 3-bath ranch home offers the perfect combination of comfort, style, and functionality. With over 2,000 square feet of finished living space, this home is designed to accommodate both everyday living and effortless entertaining. Step inside to find warm hardwood flooring, abundant natural light, and thoughtfully renovated spaces throughout. The updated kitchen serves as the centerpiece of the home, featuring a large island, pantry, recessed lighting, and a seamless connection to the dining area. Two charming brick fireplaces add character and create inviting spaces to gather with family and friends. The finished lower level provides even more room to spread out, complete with a spacious recreation area, built-in bar, full bathroom, garage access, and a separate exterior entrance. Whether you’re hosting game day, creating a home office, or setting up a guest retreat, this versatile space offers endless possibilities. Outside, enjoy a spacious backyard ideal for entertaining, gardening, or simply relaxing in your own private outdoor oasis. The welcoming front porch and mature neighborhood setting enhance the home’s curb appeal and charm. Ideally located near schools, parks, shopping, dining, and commuter routes, this move-in ready home offers modern updates, generous living space, and a prime location. Don’t miss the opportunity to make this Cedarmeade gem your next home.

Nestled in the established Cedarmeade community, this beautifully updated 4-bedroom, 3-bath ranch home offers the perfect combination of comfort, style, and functionality. With over 2,000 square feet of finished living space, this home is designed to accommodate both everyday living and effortless entertaining. Step inside to find warm hardwood flooring, abundant natural light, and thoughtfully renovated spaces throughout. The updated kitchen serves as the centerpiece of the home, featuring a large island, pantry, recessed lighting, and a seamless connection to the dining area. Two charming brick fireplaces add character and create inviting spaces to gather with family and friends. The finished lower level provides even more room to spread out, complete with a spacious recreation area, built-in bar, full bathroom, garage access, and a separate exterior entrance. Whether you’re hosting game day, creating a home office, or setting up a guest retreat, this versatile space offers endless possibilities. Outside, enjoy a spacious backyard ideal for entertaining, gardening, or simply relaxing in your own private outdoor oasis. The welcoming front porch and mature neighborhood setting enhance the home’s curb appeal and charm. Ideally located near schools, parks, shopping, dining, and commuter routes, this move-in ready home offers modern updates, generous living space, and a prime location. Don’t miss the opportunity to make this Cedarmeade gem your next home.

110 Russellcroft Rd, Winchester

Listing courtesy of Coldwell Banker Premier. Contact: 990007.lead@leads.leadrouter.com

$348,000

Enjoy one-level living in this spectacularly located brick rambler, nestled in a quiet residential neighborhood while remaining conveniently close to Route 11 with easy access to I-81. The property currently has a long term month-to-month tenant paying under market value, offering flexibility for an owner-occupant or an investor seeking rental income with potential for increased rent. Situated on a desirable corner lot, the home features ample driveway parking and presents a variety of opportunities to suit your needs.

Enjoy one-level living in this spectacularly located brick rambler, nestled in a quiet residential neighborhood while remaining conveniently close to Route 11 with easy access to I-81. The property currently has a long term month-to-month tenant paying under market value, offering flexibility for an owner-occupant or an investor seeking rental income with potential for increased rent. Situated on a desirable corner lot, the home features ample driveway parking and presents a variety of opportunities to suit your needs.

302 Wentworth Dr, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911

$295,000

Ideally situated just minutes from I-81 and a short drive to historic Old Town Winchester, this centrally located rambler offers both convenience and investment potential. Situated on a desirable corner lot, the property features a fenced yard and a storage shed for added functionality. The home has been recently refreshed with new paint and landscaping, providing excellent curb appeal and a well-maintained appearance. Whether you're looking to expand your investment portfolio or secure a future owner-occupied residence, this property presents a great opportunity. A tenant is currently in place through November 8, 2026, paying below market value, with potential for future rent increases. Enjoy immediate rental income and long-term upside in a sought-after location.

Ideally situated just minutes from I-81 and a short drive to historic Old Town Winchester, this centrally located rambler offers both convenience and investment potential. Situated on a desirable corner lot, the property features a fenced yard and a storage shed for added functionality. The home has been recently refreshed with new paint and landscaping, providing excellent curb appeal and a well-maintained appearance. Whether you're looking to expand your investment portfolio or secure a future owner-occupied residence, this property presents a great opportunity. A tenant is currently in place through November 8, 2026, paying below market value, with potential for future rent increases. Enjoy immediate rental income and long-term upside in a sought-after location.

405 Shenandoah Ave, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911

$359,900

Enchanting Cape Cod in an ideal in‑town location, this home has a welcoming ease to it, offering 3–4 bedrooms and 2.5 bathrooms with a layout that adapts beautifully to everyday living. The main level includes two convenient bedrooms, a comfortable, light‑filled living room, a separate dining area, and a renovated kitchen featuring new cabinets and stainless‑steel appliances. In 2021, the home received a thoughtful refresh: new vinyl plank flooring throughout, renovated bathrooms, new light fixtures, new receptacles/switches/covers, a new roof, and more—paired with updated plumbing for added peace of mind. Upstairs, you’ll find two additional rooms and a bathroom, including a potential fourth bedroom or bonus room ideal for an office or extra space. With over 2,000 sq ft of finished living space, the home also includes a finished basement with a full bath and a door leading directly to the backyard, offering room to expand, unwind, or create a second living area. Outside you will find a spacious deck and fully fenced backyard with privacy fencing creating a comfortable outdoor retreat—perfect for relaxed evenings, weekend grilling, and easy gatherings. All of this in a downtown Winchester location, close to shopping, restaurants, and everyday conveniences. For anyone searching for a place that simply feels right the moment you arrive—a reminder that home isn’t just a place, it’s a feeling—this enchanting Cape Cod captures it. Schedule your tour today!

Enchanting Cape Cod in an ideal in‑town location, this home has a welcoming ease to it, offering 3–4 bedrooms and 2.5 bathrooms with a layout that adapts beautifully to everyday living. The main level includes two convenient bedrooms, a comfortable, light‑filled living room, a separate dining area, and a renovated kitchen featuring new cabinets and stainless‑steel appliances. In 2021, the home received a thoughtful refresh: new vinyl plank flooring throughout, renovated bathrooms, new light fixtures, new receptacles/switches/covers, a new roof, and more—paired with updated plumbing for added peace of mind. Upstairs, you’ll find two additional rooms and a bathroom, including a potential fourth bedroom or bonus room ideal for an office or extra space. With over 2,000 sq ft of finished living space, the home also includes a finished basement with a full bath and a door leading directly to the backyard, offering room to expand, unwind, or create a second living area. Outside you will find a spacious deck and fully fenced backyard with privacy fencing creating a comfortable outdoor retreat—perfect for relaxed evenings, weekend grilling, and easy gatherings. All of this in a downtown Winchester location, close to shopping, restaurants, and everyday conveniences. For anyone searching for a place that simply feels right the moment you arrive—a reminder that home isn’t just a place, it’s a feeling—this enchanting Cape Cod captures it. Schedule your tour today!

621 Patterson Ave, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484

$359,900

Welcome to Gray Avenue! This beautifully updated 3-bedroom, 2-bath home offers over 1,700 square feet of stylish living space, blending timeless charm with modern finishes throughout. Rich hardwood floors flow throughout the home, creating warmth and character from the moment you step inside. The sun-filled living room feels bright and inviting, highlighted by a custom light fixture and a seamless connection to the formal dining area—perfect for hosting friends and family. The kitchen is a standout feature, boasting granite countertops, stainless steel appliances, white cabinetry, and designer-inspired finishes that make both cooking and entertaining a pleasure. Each bedroom is generously sized with ample closet space, while the thoughtful layout provides comfort and functionality throughout. Outside, a private cement parking pad adds everyday convenience. Packed with charm, natural light, and updates you'll love, Gray Avenue is the perfect place to call home.