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$539,900

Enjoy city living in this spacious and light-filled home featuring 5 bedrooms and 3.5 baths. Fresh new carpeting has been installed on the upper level and in the family room, complemented by hardwood floors throughout the main living areas. The kitchen is equipped with stainless steel appliances, double ovens, and a center island—perfect for cooking and entertaining. Formal living and dining rooms offer plenty of space for gatherings, while large windows provide abundant natural light throughout the home. The walk-up basement includes a full bath, rec room, and a versatile 5th bedroom that can also serve as an office or playroom (no egress window). Outside, enjoy a stamped concrete patio and fully fenced rear yard. Located in a sidewalk-lined neighborhood with streetlights and a nearby playground, this home is just 5 minutes from downtown. A wonderful place to call home!

5 Beds ⋅ 4 Baths

Enjoy city living in this spacious and light-filled home featuring 5 bedrooms and 3.5 baths. Fresh new carpeting has been installed on the upper level and in the family room, complemented by hardwood floors throughout the main living areas. The kitchen is equipped with stainless steel appliances, double ovens, and a center island—perfect for cooking and entertaining. Formal living and dining rooms offer plenty of space for gatherings, while large windows provide abundant natural light throughout the home. The walk-up basement includes a full bath, rec room, and a versatile 5th bedroom that can also serve as an office or playroom (no egress window). Outside, enjoy a stamped concrete patio and fully fenced rear yard. Located in a sidewalk-lined neighborhood with streetlights and a nearby playground, this home is just 5 minutes from downtown. A wonderful place to call home!

660 Beehive Way, Winchester

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

$399,900

Seeking the perfect blend of historic character and modern urban living? This exceptional Urban Lofts Condominium is just one and a half blocks from Old Town Winchester Walking Mall, offering easy access to restaurants, boutiques, entertainment, and vibrant downtown living. Originally built in the early 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural charm, and thoughtfully curated modern finishes throughout. A welcoming front porch adds to the home's character and curb appeal, while inside, the gourmet kitchen features upgraded cabinetry, premium quartz countertops, stainless steel appliances, and sleek designer touches. The home also features an energy-efficient hybrid heat pump water heater, which uses approximately one-third the electricity of a traditional electric water heater, helping reduce utility costs while providing reliable hot water. Spa-like baths offer stunning tile work, custom cabinetry, and stylish lighting. One of the standout features of this home is the charming private rear patio—an ideal outdoor extension of the living space, perfect for entertaining, dining al fresco, or simply relaxing. The property also includes a dedicated assigned parking space that is pre-wired and EV charger ready, offering added convenience for modern living. A spacious unfinished dry basement provides exceptional storage space, an uncommon and highly desirable feature for downtown living, offering plenty of room for seasonal décor, bicycles, outdoor gear, and more. The monthly condo fee also includes exterior maintenance of common areas, snow removal, water & sewer service, adding value and helping simplify your monthly household expenses. Whether you are seeking a sophisticated primary residence, a lock-and-leave weekend retreat, or an investment opportunity, this move-in ready condo offers an exceptional combination of location, character, energy efficiency, storage, and modern upgrades that are difficult to duplicate. This is a wonderful opportunity to purchase pieces that complement the home's style and make moving in even easier. Please inquire for a list of available items and pricing. Schedule your private showing today and experience downtown Winchester living at its fines 🏡✨ Love the furnishings? Buy it furnished for $415000!

2 Beds ⋅ 2 Baths

Seeking the perfect blend of historic character and modern urban living? This exceptional Urban Lofts Condominium is just one and a half blocks from Old Town Winchester Walking Mall, offering easy access to restaurants, boutiques, entertainment, and vibrant downtown living. Originally built in the early 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural charm, and thoughtfully curated modern finishes throughout. A welcoming front porch adds to the home's character and curb appeal, while inside, the gourmet kitchen features upgraded cabinetry, premium quartz countertops, stainless steel appliances, and sleek designer touches. The home also features an energy-efficient hybrid heat pump water heater, which uses approximately one-third the electricity of a traditional electric water heater, helping reduce utility costs while providing reliable hot water. Spa-like baths offer stunning tile work, custom cabinetry, and stylish lighting. One of the standout features of this home is the charming private rear patio—an ideal outdoor extension of the living space, perfect for entertaining, dining al fresco, or simply relaxing. The property also includes a dedicated assigned parking space that is pre-wired and EV charger ready, offering added convenience for modern living. A spacious unfinished dry basement provides exceptional storage space, an uncommon and highly desirable feature for downtown living, offering plenty of room for seasonal décor, bicycles, outdoor gear, and more. The monthly condo fee also includes exterior maintenance of common areas, snow removal, water & sewer service, adding value and helping simplify your monthly household expenses. Whether you are seeking a sophisticated primary residence, a lock-and-leave weekend retreat, or an investment opportunity, this move-in ready condo offers an exceptional combination of location, character, energy efficiency, storage, and modern upgrades that are difficult to duplicate. This is a wonderful opportunity to purchase pieces that complement the home's style and make moving in even easier. Please inquire for a list of available items and pricing. Schedule your private showing today and experience downtown Winchester living at its fines 🏡✨ Love the furnishings? Buy it furnished for $415000!

118 1/2 E Cork St, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099

$3,250,000

Rare opportunity to own a 22,320 sq. ft. indoor sports and entertainment facility situated on 3 acres with Industrial zoning. Formerly a youth development center, the building features two gymnasiums, a theater area, multiple kitchens with dining spaces, and several large restroom areas. The flexible layout supports single-tenant or multi-tenant use, making it ideal for recreational, institutional, or commercial operations. The property also offers extensive on-site parking and excellent potential for adaptive reuse. Unique large-scale facility with a wide range of possible uses.

3 Battaile Dr, Winchester

Listing courtesy of Commercial Specialists. Contact:

$339,000

Welcome to 307 1/2 E Piccadilly Street, a charming detached home offering comfort, convenience, and character in the heart of Winchester. Ideally located just minutes from Old Town Winchester, the Walking Mall, local restaurants, shopping, parks, and commuter routes, this property places you close to downtown amenities while still offering the privacy and feel of a standalone home. Inside, you’ll find a practical and inviting layout featuring 3 bedrooms, 1.5 bathrooms, a spacious kitchen, separate living and dining areas, main-level laundry, and additional storage space. Recent updates add extra peace of mind, including an HVAC system installed in 2020 and a roof recoated in 2021. Outside, the home offers valuable city-living features, including off-street parking and usable outdoor space for relaxing, gardening, pets, or entertaining. The surrounding streetscape is also seeing meaningful improvements, with the street being repaved, sidewalks redone, and new trees expected to be planted along the street. Whether you are searching for a primary residence, a Winchester-area home base, or a potential investment property, this home offers a strong combination of location, utility, and opportunity in an established Winchester neighborhood with quick access to major roadways and the surrounding Shenandoah Valley. Seller offering up to $2,500 towards painting with acceptable offer.

3 Beds ⋅ 2 Baths

Welcome to 307 1/2 E Piccadilly Street, a charming detached home offering comfort, convenience, and character in the heart of Winchester. Ideally located just minutes from Old Town Winchester, the Walking Mall, local restaurants, shopping, parks, and commuter routes, this property places you close to downtown amenities while still offering the privacy and feel of a standalone home. Inside, you’ll find a practical and inviting layout featuring 3 bedrooms, 1.5 bathrooms, a spacious kitchen, separate living and dining areas, main-level laundry, and additional storage space. Recent updates add extra peace of mind, including an HVAC system installed in 2020 and a roof recoated in 2021. Outside, the home offers valuable city-living features, including off-street parking and usable outdoor space for relaxing, gardening, pets, or entertaining. The surrounding streetscape is also seeing meaningful improvements, with the street being repaved, sidewalks redone, and new trees expected to be planted along the street. Whether you are searching for a primary residence, a Winchester-area home base, or a potential investment property, this home offers a strong combination of location, utility, and opportunity in an established Winchester neighborhood with quick access to major roadways and the surrounding Shenandoah Valley. Seller offering up to $2,500 towards painting with acceptable offer.

307 E Piccadilly St, Winchester

Listing courtesy of HoneyWay. Contact: 5402149682

$1,179,000

Stepping onto the Southern style covered front porc.h you enter the large foyer with a Schoenbek chandelier. There is a living room to the left which opens to a separate dining room with a hand painted blue and gold ceiling. The kitchen is eating size with granite counter and large island. Double doors lead to a small back porch and stairs to the patio. The first floor family room has a gas fireplace, built-in cabinets, a built-in window seat and two-story windows. The garden room has tile floor, built-in bookcases and windows on two sides overlook the rose garden and back yard. There is a powder room off the family room. The second floor has four bedrooms and three full baths. The master bedroom is very large with a three-sided fireplace and sitting area with tray ceilings. There is a large walk-in closet with custom built ins. The master bath has two separate vanities with vessel sinks. The generous shower is glass sided and there is a large spa tub with a Schoenbek chandlier. The bath has a tile floor and artistic tiles around the shower, spa tub and vanities. Two bedrooms share a jack and jill bath with each haviing it's own vanity.. All the bathrooms have marble counters. There is a library on this floor with built in bookcases which could be turned into a fifth bedroom. The upper hall has an overlook to the family room below. You enter the lower level from the kitchen and there is an exit from the recreation room onto the patio at the rear. There is a gas fireplace in the large family room with a wet bar and a generous adjoining area for activities. There is a gym with a wall of mirrors, an office, a large cedar closet, half bath and storage room. The entire house has crown molding, many shadow boxes, and 5" baseboards. All the walks, the driveway and the patio are done in architectual concrete. The rear yard has a waterfall, brick walls and extensive plantings. On the side of the home there is a large rose garden. The house has a security system; and also, the entire home is wired with speakers for music. The roof is less than 5 years old. The oven and microwave were new in 2025. Details about each room is found in documents. This home is within 5 minutes of Medical Center, Museum of the Shenandoah Valley and the Green Trail and within 10 minutes of Old Town Walking Mall, Shenandoah University and shopping, Note: one owner is licensed broker/real estate agent & other owner is licensed real estate agent

4 Beds ⋅ 5 Baths

Stepping onto the Southern style covered front porc.h you enter the large foyer with a Schoenbek chandelier. There is a living room to the left which opens to a separate dining room with a hand painted blue and gold ceiling. The kitchen is eating size with granite counter and large island. Double doors lead to a small back porch and stairs to the patio. The first floor family room has a gas fireplace, built-in cabinets, a built-in window seat and two-story windows. The garden room has tile floor, built-in bookcases and windows on two sides overlook the rose garden and back yard. There is a powder room off the family room. The second floor has four bedrooms and three full baths. The master bedroom is very large with a three-sided fireplace and sitting area with tray ceilings. There is a large walk-in closet with custom built ins. The master bath has two separate vanities with vessel sinks. The generous shower is glass sided and there is a large spa tub with a Schoenbek chandlier. The bath has a tile floor and artistic tiles around the shower, spa tub and vanities. Two bedrooms share a jack and jill bath with each haviing it's own vanity.. All the bathrooms have marble counters. There is a library on this floor with built in bookcases which could be turned into a fifth bedroom. The upper hall has an overlook to the family room below. You enter the lower level from the kitchen and there is an exit from the recreation room onto the patio at the rear. There is a gas fireplace in the large family room with a wet bar and a generous adjoining area for activities. There is a gym with a wall of mirrors, an office, a large cedar closet, half bath and storage room. The entire house has crown molding, many shadow boxes, and 5" baseboards. All the walks, the driveway and the patio are done in architectual concrete. The rear yard has a waterfall, brick walls and extensive plantings. On the side of the home there is a large rose garden. The house has a security system; and also, the entire home is wired with speakers for music. The roof is less than 5 years old. The oven and microwave were new in 2025. Details about each room is found in documents. This home is within 5 minutes of Medical Center, Museum of the Shenandoah Valley and the Green Trail and within 10 minutes of Old Town Walking Mall, Shenandoah University and shopping, Note: one owner is licensed broker/real estate agent & other owner is licensed real estate agent

1004 Heth Pl, Winchester

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

$359,000

Price Reduced $15,000! Highly Motivated Seller! Welcome to this meticulously maintained, 3 bedroom, move-in-ready ranch home located within Winchester City limits. Perfectly situated on a premium, near-half-acre lot (.46 acres) off Papermill Road, this property offers the ultimate blend of city convenience and peaceful privacy with no backyard neighbors. Kitchen and downstairs bathroom to be painted. Property Highlights: 3 bedrooms on main level of home. Wonderful natural lighting throughout. Expansive Basement: 75% finished lower level with carpet offers endless possibilities for a rec room, gym, or home office. The remaining 25% provides excellent storage space and a dedicated workshop area. Recent Upgrades: Complete peace of mind with a new HVAC system (2019), a brand-new water heater (2025), and newer energy-efficient windows throughout. Outdoor Oasis: Relax on your covered back patio overlooking a massive backyard that borders Buffalo Lick Run. Perfect for watching local wildlife! Includes a handy storage shed. Perks & Location: No HOA fees (and city trash pickup is included!). Walk to the scenic paths at Weaver Park, and enjoy prime shopping and dining less than a mile away. Don't miss out on this city gem with a country feel—schedule your tour today!

3 Beds ⋅ 2 Baths

Price Reduced $15,000! Highly Motivated Seller! Welcome to this meticulously maintained, 3 bedroom, move-in-ready ranch home located within Winchester City limits. Perfectly situated on a premium, near-half-acre lot (.46 acres) off Papermill Road, this property offers the ultimate blend of city convenience and peaceful privacy with no backyard neighbors. Kitchen and downstairs bathroom to be painted. Property Highlights: 3 bedrooms on main level of home. Wonderful natural lighting throughout. Expansive Basement: 75% finished lower level with carpet offers endless possibilities for a rec room, gym, or home office. The remaining 25% provides excellent storage space and a dedicated workshop area. Recent Upgrades: Complete peace of mind with a new HVAC system (2019), a brand-new water heater (2025), and newer energy-efficient windows throughout. Outdoor Oasis: Relax on your covered back patio overlooking a massive backyard that borders Buffalo Lick Run. Perfect for watching local wildlife! Includes a handy storage shed. Perks & Location: No HOA fees (and city trash pickup is included!). Walk to the scenic paths at Weaver Park, and enjoy prime shopping and dining less than a mile away. Don't miss out on this city gem with a country feel—schedule your tour today!

328 Longview Ave, Winchester

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

$379,900

This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door. The home looks bright and beautiful from the inside and out. The bathrooms have also gotten a modern makeover, complete with touch mirrors that add a touch of luxury. This one's a must-see!

2 Beds ⋅ 2 Baths

This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door. The home looks bright and beautiful from the inside and out. The bathrooms have also gotten a modern makeover, complete with touch mirrors that add a touch of luxury. This one's a must-see!

711 E Cork St, Winchester

Listing courtesy of Spring Hill Real Estate, LLC.. Contact: 7038914520

$339,900

"Beautifully Renovated On Pall Mall St." This 2-bedroom, 2-full bath ranch style home is ready for you to move right in! Home has been completely painted on the inside, and the outside brick/concrete, side handrails, outside/inside of doors have been freshly painted. The kitchen has new granite counters, new sink & faucet, new LVP flooring and new stainless-steel appliances. Huge family room with a large wood burning fireplace, two new windows, a new storm door, new LVP flooring, new baseboard heaters, new window A/C unit and remodeled full bathroom off of it. Both bedrooms have gorgeous, refinished hardwood floors that continue down the hall area and into a living room and dining room. Hallway bathroom has new LVP flooring, new window, new toilet and tile around the tub/shower. Large laundry room with new LVP flooring, new baseboard heater and new window. Huge deck out back with new floorboards, new top railings and new step/concrete pad down to the yard. Two great sized sheds (One with new doors). New HVAC, new thermostat and new water heater! Both Crawl Spaces have new insulation, new moisture barriers and new entrance doors. Roof was replaced in October of 2019. Chimney was inspected, cleaned and repaired as recommended so it's ready for you to enjoy! New switches, receptacles, smoke detectors, doorknobs and light fixtures throughout the home. Home has been power washed and fresh mulch put down. Agent/Owner

2 Beds ⋅ 2 Baths

"Beautifully Renovated On Pall Mall St." This 2-bedroom, 2-full bath ranch style home is ready for you to move right in! Home has been completely painted on the inside, and the outside brick/concrete, side handrails, outside/inside of doors have been freshly painted. The kitchen has new granite counters, new sink & faucet, new LVP flooring and new stainless-steel appliances. Huge family room with a large wood burning fireplace, two new windows, a new storm door, new LVP flooring, new baseboard heaters, new window A/C unit and remodeled full bathroom off of it. Both bedrooms have gorgeous, refinished hardwood floors that continue down the hall area and into a living room and dining room. Hallway bathroom has new LVP flooring, new window, new toilet and tile around the tub/shower. Large laundry room with new LVP flooring, new baseboard heater and new window. Huge deck out back with new floorboards, new top railings and new step/concrete pad down to the yard. Two great sized sheds (One with new doors). New HVAC, new thermostat and new water heater! Both Crawl Spaces have new insulation, new moisture barriers and new entrance doors. Roof was replaced in October of 2019. Chimney was inspected, cleaned and repaired as recommended so it's ready for you to enjoy! New switches, receptacles, smoke detectors, doorknobs and light fixtures throughout the home. Home has been power washed and fresh mulch put down. Agent/Owner

420 E Pall Mall St, Winchester

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

$760,000

Welcome to 769 Seldon Drive—an elegant brick-front colonial situated on nearly half an acre in one of Winchester’s most desirable neighborhoods. Offering over 4,500 finished square feet, this spacious 5-bedroom, 4.5-bath home is designed for comfort, flexibility, and multi-generational living. The main level features a generously sized primary suite with a walk-in closet and en-suite bath, along with formal living and dining rooms, a warm and inviting family room with fireplace, and a well-equipped kitchen with center island and breakfast area. Hardwood floors and detailed trim work add classic character throughout. A standout feature of this home is the private ground-level apartment with its own entrance—complete with a full kitchen, bedroom, bathroom, living space, and dedicated laundry. Perfect for guests, extended family, or potential rental income. Upstairs, you'll find additional spacious bedrooms and full baths, offering plenty of room for everyone. Enjoy the outdoors from your beautifully landscaped yard with space to garden, entertain, or relax. A two-car garage and extended driveway provide ample parking. Conveniently located just minutes to downtown Winchester, parks, shopping, dining, and commuter routes—this home offers the space and versatility you've been searching for. Schedule your private showing today!

5 Beds ⋅ 5 Baths

Welcome to 769 Seldon Drive—an elegant brick-front colonial situated on nearly half an acre in one of Winchester’s most desirable neighborhoods. Offering over 4,500 finished square feet, this spacious 5-bedroom, 4.5-bath home is designed for comfort, flexibility, and multi-generational living. The main level features a generously sized primary suite with a walk-in closet and en-suite bath, along with formal living and dining rooms, a warm and inviting family room with fireplace, and a well-equipped kitchen with center island and breakfast area. Hardwood floors and detailed trim work add classic character throughout. A standout feature of this home is the private ground-level apartment with its own entrance—complete with a full kitchen, bedroom, bathroom, living space, and dedicated laundry. Perfect for guests, extended family, or potential rental income. Upstairs, you'll find additional spacious bedrooms and full baths, offering plenty of room for everyone. Enjoy the outdoors from your beautifully landscaped yard with space to garden, entertain, or relax. A two-car garage and extended driveway provide ample parking. Conveniently located just minutes to downtown Winchester, parks, shopping, dining, and commuter routes—this home offers the space and versatility you've been searching for. Schedule your private showing today!

769 Seldon Dr, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099

$599,950

Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking for 3-4 cars. Plus, dry basement storage available for tenant or landlord

446 N Loudoun St, Winchester

Listing courtesy of Homes By Owner, Inc.. Contact: 3013556104

$599,950

Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking for 3-4 cars. Plus, dry basement storage available for tenant or landlord

5 Beds ⋅ 2 Baths

Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking for 3-4 cars. Plus, dry basement storage available for tenant or landlord

446 N Loudoun St, Winchester

Listing courtesy of Homes By Owner, Inc.. Contact: 3013556104

$328,500

Charming 3-bedroom, 1-bath ranch-style home in a highly convenient Winchester location! This well-maintained home is in great condition and has been freshly painted, offering a clean, move-in ready feel. Featuring beautiful hardwood floors throughout and a fully fenced backyard—perfect for pets, entertaining, or relaxing evenings. Central heating and air conditioning for year-round comfort. Convenient one-level living throughout. Ideally situated just off Berryville Avenue, with quick access to shopping, dining, and major commuter routes, making it a great option for those traveling to Northern Virginia. Don’t miss this opportunity!

3 Beds ⋅ 1 Baths

Charming 3-bedroom, 1-bath ranch-style home in a highly convenient Winchester location! This well-maintained home is in great condition and has been freshly painted, offering a clean, move-in ready feel. Featuring beautiful hardwood floors throughout and a fully fenced backyard—perfect for pets, entertaining, or relaxing evenings. Central heating and air conditioning for year-round comfort. Convenient one-level living throughout. Ideally situated just off Berryville Avenue, with quick access to shopping, dining, and major commuter routes, making it a great option for those traveling to Northern Virginia. Don’t miss this opportunity!

608 Dunlap St, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$320,000

Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett Park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. New roof installed in 2018. Open House on Sunday, August 16th from 1-4pm.

3 Beds ⋅ 3 Baths

Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett Park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. New roof installed in 2018. Open House on Sunday, August 16th from 1-4pm.

115 S Purcell Ave, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$447,000

Discover a stunning blend of Colonial and Contemporary architecture in this exquisite 3-bedroom, 2.5-bathroom residence, built in 2024. Step inside to find luxurious vinyl plank flooring and plush carpeting that exude warmth and sophistication. The gourmet kitchen is a chef's dream, equipped with high-end appliances including a sleek wall oven, cooktop, and energy-efficient refrigerator, ensuring culinary excellence at every turn. Recessed lighting and elegant window treatments enhance the ambiance, creating a serene retreat. The exterior boasts tasteful features such as exterior lighting and a well-designed gutter system, while the expansive half-acre lot offers ample space for outdoor activities. Enjoy evenings on the spacious deck, perfect for al fresco dining or simply soaking in the tranquility of your surroundings. Additional highlights include an attached two-car garage with a front entry and convenient asphalt driveway, ensuring ease of access. Safety is paramount with smoke and carbon monoxide detectors installed throughout. This property is not just a home; it's a lifestyle of luxury and comfort, where every detail has been thoughtfully curated for your enjoyment. Embrace the opportunity to elevate your living experience in this exceptional residence.

3 Beds ⋅ 3 Baths

Discover a stunning blend of Colonial and Contemporary architecture in this exquisite 3-bedroom, 2.5-bathroom residence, built in 2024. Step inside to find luxurious vinyl plank flooring and plush carpeting that exude warmth and sophistication. The gourmet kitchen is a chef's dream, equipped with high-end appliances including a sleek wall oven, cooktop, and energy-efficient refrigerator, ensuring culinary excellence at every turn. Recessed lighting and elegant window treatments enhance the ambiance, creating a serene retreat. The exterior boasts tasteful features such as exterior lighting and a well-designed gutter system, while the expansive half-acre lot offers ample space for outdoor activities. Enjoy evenings on the spacious deck, perfect for al fresco dining or simply soaking in the tranquility of your surroundings. Additional highlights include an attached two-car garage with a front entry and convenient asphalt driveway, ensuring ease of access. Safety is paramount with smoke and carbon monoxide detectors installed throughout. This property is not just a home; it's a lifestyle of luxury and comfort, where every detail has been thoughtfully curated for your enjoyment. Embrace the opportunity to elevate your living experience in this exceptional residence.

310 Longview Ave, Winchester

Listing courtesy of Coldwell Banker Realty. Contact: 7034717220

$575,000

Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful original hardwood floors, tall ceilings, fireplace, 4 season sunroom, and a stunning staircase that adds timeless character. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you can rent out both units for a strong investment. The rear unit is already leased to a reliable tenant, providing immediate cash flow. The entire home can easily be converted back to one large living space with the removal of drywall over two doorways. The new roof and gutters were installed in 2024 and both full bathrooms have been updated to include walk-in tiled showers. The heating fuel was converted to natural gas and new boilers were installed in 2011. Each unit has separate utilities except for water and sewer. With its unique character, flexible layout, and proven rental history, this property offers endless possibilities for living, investing, or both!

6 Beds ⋅ 4 Baths

Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful original hardwood floors, tall ceilings, fireplace, 4 season sunroom, and a stunning staircase that adds timeless character. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you can rent out both units for a strong investment. The rear unit is already leased to a reliable tenant, providing immediate cash flow. The entire home can easily be converted back to one large living space with the removal of drywall over two doorways. The new roof and gutters were installed in 2024 and both full bathrooms have been updated to include walk-in tiled showers. The heating fuel was converted to natural gas and new boilers were installed in 2011. Each unit has separate utilities except for water and sewer. With its unique character, flexible layout, and proven rental history, this property offers endless possibilities for living, investing, or both!

1400 Valley Ave, Winchester

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

$575,000

Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful wood floors, tall ceilings, fireplace, sunroom, and a stunning staircase that adds timeless character. Each Unit has 3 bedrooms and 1.5 baths. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you can rent out both units for a strong investment. The rear unit is already leased to a reliable tenant, providing immediate cash flow. The new roof and gutters were installed just last year and both full bathrooms have been updated to include walk-in tiled showers. The heating fuel was converted to natural gas and new boilers were installed in 2011. Each unit has separate utilities except for water and sewer. With its unique character, flexible layout, and proven rental history, this property offers endless possibilities for living, investing, or both!

1400 Valley Ave, Winchester

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

$399,000

TONS OF UPGRADES! This home has been updated top to bottom. From the roof, windows, kitchen, bathrooms, light fixtures, HVAC, and so on. Located just 1 block from Handley High School, this home and all of its high end improvements make it a treasure waiting to be discovered. As you walk through this home you'll notice that a ton of care and thoughtfulness was put into what it is today. The bathrooms having double vanities, fully tiled showers, upgrades to the flooring, walk-in closes in two bedrooms, a mud room in the rear of the home with a half bath for your guests, and a beautiful front porch to enjoy all of the downtown Winchester events.

3 Beds ⋅ 3 Baths

TONS OF UPGRADES! This home has been updated top to bottom. From the roof, windows, kitchen, bathrooms, light fixtures, HVAC, and so on. Located just 1 block from Handley High School, this home and all of its high end improvements make it a treasure waiting to be discovered. As you walk through this home you'll notice that a ton of care and thoughtfulness was put into what it is today. The bathrooms having double vanities, fully tiled showers, upgrades to the flooring, walk-in closes in two bedrooms, a mud room in the rear of the home with a half bath for your guests, and a beautiful front porch to enjoy all of the downtown Winchester events.

1025 S Loudoun St, Winchester

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

$675,000

100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025! This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic Winchester Award of Merit, this home showcases exceptional craftsmanship and dedication to preserving its character while delivering today’s comforts. Major improvements include all-new electrical, plumbing, and ductwork, along with professionally engineered structural reinforcements for long-term integrity and peace of mind. Inside, you’ll find two brand-new HVAC systems, energy-efficient windows and doors, and beautifully refinished original hardwood floors throughout. The designer kitchen features granite countertops and a custom slide-up serving window that opens to a stylish outdoor bar—perfect for entertaining. Bathrooms offer elegant tile finishes and a jetted tub for a spa-like retreat. Custom details such as barn doors, solid wood interior doors, and upgraded lighting elevate the home’s unique character. The exterior is equally impressive, featuring a custom front door, welcoming new front porch, vinyl privacy fencing, a freshly seeded backyard, and a slate patio accented with ambient string lighting. A cobblestone driveway provides two off-street parking spaces—an added luxury in this walkable downtown location. A rare opportunity to own a one-of-a-kind home that perfectly balances historic appeal, modern efficiency, and exceptional craftsmanship in one of Winchester’s most desirable neighborhoods.

3 Beds ⋅ 3 Baths

100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025! This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic Winchester Award of Merit, this home showcases exceptional craftsmanship and dedication to preserving its character while delivering today’s comforts. Major improvements include all-new electrical, plumbing, and ductwork, along with professionally engineered structural reinforcements for long-term integrity and peace of mind. Inside, you’ll find two brand-new HVAC systems, energy-efficient windows and doors, and beautifully refinished original hardwood floors throughout. The designer kitchen features granite countertops and a custom slide-up serving window that opens to a stylish outdoor bar—perfect for entertaining. Bathrooms offer elegant tile finishes and a jetted tub for a spa-like retreat. Custom details such as barn doors, solid wood interior doors, and upgraded lighting elevate the home’s unique character. The exterior is equally impressive, featuring a custom front door, welcoming new front porch, vinyl privacy fencing, a freshly seeded backyard, and a slate patio accented with ambient string lighting. A cobblestone driveway provides two off-street parking spaces—an added luxury in this walkable downtown location. A rare opportunity to own a one-of-a-kind home that perfectly balances historic appeal, modern efficiency, and exceptional craftsmanship in one of Winchester’s most desirable neighborhoods.

112 W Germain St, Winchester

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

$390,000

Priced to reflect the need for some updating, this home offers opportunities and personalization while remaining move-in ready 1011sf total living space. This home is in very good shape. The sellers are selling this property completely As-IS. NO HOA Perfectly home on a quiet lot embraced by mature, stately trees, this 5-bedroom, 2 full-bathroom home offers both seclusion and incredible proximity to Winchester's finest amenities, schools, shopping, and major commuter routes. You have to come and see it. This home is seller's Occupied.

5 Beds ⋅ 2 Baths

Priced to reflect the need for some updating, this home offers opportunities and personalization while remaining move-in ready 1011sf total living space. This home is in very good shape. The sellers are selling this property completely As-IS. NO HOA Perfectly home on a quiet lot embraced by mature, stately trees, this 5-bedroom, 2 full-bathroom home offers both seclusion and incredible proximity to Winchester's finest amenities, schools, shopping, and major commuter routes. You have to come and see it. This home is seller's Occupied.

605 Dunlap St, Winchester

Listing courtesy of Spring Hill Real Estate, LLC.. Contact: 7038914520

$199,900

NEW CITY LOT! This newly configured lot in the heart of downtown Winchester has been expanded and is ready for you to build your dream home. Featuring a width of approximately 100 feet, you have plenty of space to accommodate nearly any home of your choice. As a bonus, the driveway will be on the neighboring lot, which allows even more buildable space. Additionally, you do not have to worry about anyone building behind you. The lot sits, just outside of the historic district, making your building process significantly easier. This is a truly rare opportunity to purchase one of the last remaining lots in downtown Winchester. The Seller also has plans available to qualified buyers.

506 Fairmont Ave, Winchester

Listing courtesy of Colony Realty. Contact:

$400,000

Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

4 Beds ⋅ 2 Baths

Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

115 E Monmouth St, Winchester

Listing courtesy of Inmobiliaria De Las Casas LLC. Contact: 5713539363

$700,000

0.7230 Acres located at 2970 Valley Avenue featuring a former used car lot that will offer enough area to display for 30-40 cars. There is pubic water and sewer available. The used car lot does not have an office building. An office building would have to be built or a mobile office could be utilized. A new site plan will be required from the City of Winchester to operate a used car lot.

2970 Valley Ave, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$650,000

0.429 acres located at 2970 Valley Avenue. This site could be a used car lot that will offer enough area to display for 30 cars. There is a public water and sewer available. 2978 Valley Avenue presently features 5 rental units producing gross monthly revenue of approximately $4,000. The list price for purchase is $1,350000 for both properties with 1.15 acres. Both properties can be ground leased for $6,000/month.

2978 Valley Ave, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$995,000

Yost Building Positioned in the heart of downtown, this distinguished office building—formerly the executive wing of F&M National—offers an outstanding opportunity for businesses seeking a prestigious and highly walkable location. Multiple suite sizes are available, making it ideal for professional firms, government-adjacent services, or organizations looking to establish a prominent presence in the city’s core. Situated adjacent to City Hall and steps from the Historic Walking Mall, this property provides unparalleled convenience for employees and clients alike. Within a quick walk, you’ll find the Frederick County Administrative Buildings, the Courthouse, and numerous public parking structures, ensuring seamless access for daily operations. With its prime location, flexible floorplan offerings, and proximity to key civic and commercial amenities, this downtown office building represents a rare opportunity to secure space in one of the most strategic and sought-after areas of the city. ALSO LISTED FOR LEASE

38 Rouss Ave, Winchester

Listing courtesy of Colony Realty. Contact:

$1,250,000

Located in the heart of the historic downtown district, this versatile B1-zoned property offers a rare blend of immediate income and long-term upside. The building features approximately 7,000 SF of office space complemented by 2,000 SF of ground-level shop, supported by 12 on-site parking spaces, important in the urban core. Beyond its current use, the property presents exceptional redevelopment potential, it could be conversion to nine residential units on a single floor and the ability to add up to two additional stories, creating a total of 27 residential units. Ideal for investors or developers seeking a high-visibility downtown location with historic character, flexible zoning, and significant value-add potential.

314 N Braddock St, Winchester

Listing courtesy of Colony Realty. Contact:

$175,000

Vacant Lot in Rolling Hills One of the last opportunities to own a vacant lot in the desirable Rolling Hills community. This property offers the perfect setting to build your new home or presents an excellent opportunity for a long-term investment. Enjoy a well-established neighborhood with limited remaining buildable lots. Buyer to verify zoning, utilities, and intended use. Water and Sewer tap Fees have NOT been paid.

719 Kennedy Dr, Winchester

Listing courtesy of Colony Realty. Contact:

$525,000

Back on the market, at no fault of the seller. All-brick rancher located in the sought-after Early’s Green at Meadow Branch community, offering 1,974 finished square feet with 9-foot ceilings and true one-level living. The open floor plan provides excellent flow and is ideal for both everyday living and entertaining. Recent interior updates include new hardwood flooring in the main living room, and new carpet in all bedrooms. Tile flooring has been thoughtfully retained in the kitchen, entry, and guest bath. Recessed lighting has been added to the main living area, along with multiple updated light fixtures, creating a bright and welcoming feel. The kitchen features a breakfast nook with a bay window and now includes custom built pantry storage, while the living room has been enhanced with a custom built-in with integrated lighting. A former bar area was removed and replaced with a large storage closet, significantly improving functionality. The primary bathroom has been fully gutted and completely redesigned, featuring a modern walk-in shower, contemporary fixtures, and an aging-in-place–friendly layout with grab bars and improved accessibility. The sunroom has been reconfigured for better flow, with the original sliding doors removed, a new cased opening added, and HVAC extended to the space, allowing it to be enjoyed year-round. A rear deck extends the living space outdoors. Exterior improvements include over $10,000 in rear landscaping designed to buffer Meadow Branch Avenue, featuring Crepe Myrtles, Emerald Green Arborvitae, and Hollies. A crawlspace fan/radon-style ventilation system has also been installed. Situated on a cul-de-sac and conveniently located near hospitals, shopping, dining, fitness facilities, walking trails, coffee shops, and Old Town Winchester. HOA covers lawn maintenance, snow removal, pool, and tennis courts. Not a 55+ community. Homes offering this level of care, thoughtful upgrades, and low-maintenance living in this location are rarely available.

3 Beds ⋅ 2 Baths

Back on the market, at no fault of the seller. All-brick rancher located in the sought-after Early’s Green at Meadow Branch community, offering 1,974 finished square feet with 9-foot ceilings and true one-level living. The open floor plan provides excellent flow and is ideal for both everyday living and entertaining. Recent interior updates include new hardwood flooring in the main living room, and new carpet in all bedrooms. Tile flooring has been thoughtfully retained in the kitchen, entry, and guest bath. Recessed lighting has been added to the main living area, along with multiple updated light fixtures, creating a bright and welcoming feel. The kitchen features a breakfast nook with a bay window and now includes custom built pantry storage, while the living room has been enhanced with a custom built-in with integrated lighting. A former bar area was removed and replaced with a large storage closet, significantly improving functionality. The primary bathroom has been fully gutted and completely redesigned, featuring a modern walk-in shower, contemporary fixtures, and an aging-in-place–friendly layout with grab bars and improved accessibility. The sunroom has been reconfigured for better flow, with the original sliding doors removed, a new cased opening added, and HVAC extended to the space, allowing it to be enjoyed year-round. A rear deck extends the living space outdoors. Exterior improvements include over $10,000 in rear landscaping designed to buffer Meadow Branch Avenue, featuring Crepe Myrtles, Emerald Green Arborvitae, and Hollies. A crawlspace fan/radon-style ventilation system has also been installed. Situated on a cul-de-sac and conveniently located near hospitals, shopping, dining, fitness facilities, walking trails, coffee shops, and Old Town Winchester. HOA covers lawn maintenance, snow removal, pool, and tennis courts. Not a 55+ community. Homes offering this level of care, thoughtful upgrades, and low-maintenance living in this location are rarely available.

832 Winder Ct, Winchester

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

$199,900

1415 Ramseur Ln, Winchester

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

$259,900

Check out this Very Cute Bungalow in Winchester City! It has a Brand NEW Roof, Freshly Painted throughout, NEW kitchen/hall/bath flooring, NEW Stainless Steel Refrigerator, Restored deck, and Lovely Hardwood! Cozy with 2 Bedrooms and 1 Bath. Surely to be perfect for the first time Home Buyer! Great Location close to shopping & restaurants. Great for commuters as well as it's on the East side of town and close to I-81. Schedule your showing today!

2 Beds ⋅ 1 Baths

Check out this Very Cute Bungalow in Winchester City! It has a Brand NEW Roof, Freshly Painted throughout, NEW kitchen/hall/bath flooring, NEW Stainless Steel Refrigerator, Restored deck, and Lovely Hardwood! Cozy with 2 Bedrooms and 1 Bath. Surely to be perfect for the first time Home Buyer! Great Location close to shopping & restaurants. Great for commuters as well as it's on the East side of town and close to I-81. Schedule your showing today!

1125 Conway St, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360

$995,000

Prime office or retail space in Winchester’s Opequon Center featuring ample parking, snow removal, and landscaping services. These are condominium units with 2 separate spaces available: Suite 200 and Suite 201. This is an ideal situation for the owner/investor who occupies one unit for their office or business and leases the second unit as an income-producing investment. Suite 200 will soon be vacant, and Suite 201 is leased by One Source, Inc. which is a company providing human resource recruitment, background investigation, and identity verification services. These spaces are on the second floor with elevator service. Each of the two spaces has a floor area of approximately 2,500 SF. These condominiums are located in a professionally managed office and business park with reputable neighbors such as medical offices, a real estate firm, an orthodontist, and a physical therapist.

3052 Valley Avenue Unit #200, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact: