Refine Search
Map
Sort by
$725,000
5 Beds ⋅ 4 Baths

223 Fairfield Dr, Winchester

Listing courtesy of Samson Properties. Contact: 7033788810
$749,900
5 Beds ⋅ 5 Baths
**Freshly Updated Estate on 3.46 Acres with Mountain Views | Now $749,900** Freshly reintroduced to the market with significant new upgrades and a new price! This exceptional 5-bedroom, 4.5-bath estate offers over 3,700 finished sq. ft. on 3.46 private acres with beautiful mountain views. Recent improvements give the home a fresh, elevated feel, including new interior paint, coffered ceilings, recessed lighting, an updated double-sided fireplace, new basement flooring, and new French doors. The gormet kitchen features Thor appliances, modern cabinetry, updated countertops, flooring, and fixtures. A spacious main-level primary suite offers a soaking tub, dual vanities, and separate shower. The fully finished walkout basement provides incredible flexibility with two additional bedrooms, two full baths, and a large recreation area—perfect for guests, multigenerational living, a home gym, office, or entertaining. Outside, enjoy a Trex deck, multiple patios, built-in firepit, and peaceful mountain views. Additional updates include a newer well pump, pressurized water tank, water softening system, and upstairs AC condensing unit. Adding to its one-of-a-kind story, the home was once owned by NFL MVP and Washington Redskins legend Mark Moseley. Now offered at $749,900—an incredible opportunity for this much space, acreage, character, and recent updates. Fresh look. Fresh price. Ready for its next chapter!

199 Meeting House Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$439,900
2 Beds ⋅ 2 Baths
Set on nearly two acres just minutes from historic downtown Winchester, this beautifully maintained one-level home delivers the rare combination of open country space and everyday convenience. A classic covered front porch welcomes you in, opening to a bright, open-concept kitchen and living with 10' ceilings. This central living area is designed for easy flow — cooking, gathering, and relaxing all in one connected space. Two comfortable bedrooms and two full baths include a spa-inspired retreat. One with a luxurious walk-in shower and the other with a step-up soaking tub. Out back, a covered patio overlooks the wide, level lawn — a quiet spot for morning coffee or evening entertaining, framed by mature trees and open sky. Storage and workspace are never an issue here: a two-car attached garage plus a separate detached garage offer room for vehicles, tools, hobbies, or a workshop. Manicured landscaping, crisp white siding, and a white-fenced property line complete the picture. Move-in ready, meticulously cared for, and surrounded by room to breathe — all within a short drive of Winchester's shops, dining, and Old Town district.

211 Marple Rd, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact: (301) 365-0664
$439,900
3 Beds ⋅ 2 Baths
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. 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
3 Beds ⋅ 1 Baths
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 and faucet. 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 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:

$849,900
3 Beds ⋅ 2 Baths
Permitted and delivery 4 months. Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house (new PIN OAK model); it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of single-level living in this immaculate, brand-new residence, meticulously designed with a flowing 2,488 sq. ft. open floor plan. The builder has redefined "standard features," integrating premium elements throughout the home that others typically label as costly upgrades. Key Features & Elegant Finishes: Striking Curb Appeal: A distinguished full brick front complemented by durable cement siding creates a timeless exterior, highlighted by a large, welcoming concrete front porch and lead walk. Exquisite Main Level: Rich, stained Early American hardwood flooring flows seamlessly across the entire main level, excluding the elegant tiled bathrooms and laundry room, creating a warm, inviting atmosphere. Seamless Indoor/Outdoor Entertaining: Step through to your private outdoor oasis. A covered and screened deck provides an ideal spot for year-round relaxation, extending onto an attached open deck perfect for grilling and sunbathing. This exquisite home represents a unique blend of craftsmanship, luxury, and exclusivity. Don't miss the chance to claim your spot in this premier community.

lot 12 Keval Gyan Way, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$766,000
5 Beds ⋅ 3 Baths
Beautiful 5-bedroom, 2.5-bath brick-front home situated on 2 private acres, offering the perfect blend of space, comfort, and recent updates. Major updates provide peace of mind, including a new roof (2025), HVAC systems replaced in 2023, 2024, and 2025, a new pressure tank, water heater, sump pump, Culligan water softener, and updated light fixtures Enjoy outdoor living on the spacious deck and paver patio, ideal for entertaining or relaxing. Inside, the kitchen features hardwood flooring, Corian countertops, a pantry, and ample cabinet space. The main level showcases elegant crown molding, a convenient laundry room with a shower, and freshly painted rooms that give the home a bright, refreshed feel. The oversized primary suite includes a huge walk-in closet for exceptional storage. . Full, unfinished, walkout level basement. Enjoy the privacy of country living while still being conveniently located to nearby amenities.

175 Shields Dr, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$375,000
3 Beds ⋅ 1 Baths
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
$300,000
3 Beds ⋅ 3 Baths
Charming Country Farmhouse with Modern Updates & Unrestricted Property! Welcome to this charming 1940's farmhouse, thoughtfully renovated and expanded in 2006 to blend timeless character with modern convenience. Offering 3 bedrooms and 3 full bathrooms, this inviting home provides a flexible layout that's perfect for a variety of lifestyles. The main level features a kitchen that flows seamlessly into the living room, creating the perfect gathering space. Two bedrooms and two full bathrooms are conveniently located on the main floor, including a comfortable primary suite complete with a generously sized walk-in closet and private ensuite bath. Upstairs, you'll find a spacious landing area leading to the third bedroom, which boasts its own ensuite full bath and access to a private outdoor deck—an ideal spot to enjoy your morning coffee or unwind at the end of the day. The walk-up attic offers excellent potential to finish and create additional living space, whether you envision a home office, bonus room, or hobby area. Comfort is ensured year-round with a central HVAC system, supplemented by a mini-split system and propane heater for added flexibility. The home also includes both an interior-access cellar and a traditional exterior root cellar, providing abundant storage options. Situated on a quarter-acre lot, the property also features a 24' x 24' detached two-car garage with automatic door openers and 30-amp electrical service, making it ideal for vehicles, a workshop, or recreational equipment. With no restrictions, this property offers many possibilities. Whether you're looking for modern living in a peaceful rural setting, homestead living, or simply room to create your own, this unique property is ready to welcome you home.

2346 Welltown Rd, Winchester

Listing courtesy of Touchstone Realty, LLC. Contact:

$1,350,000
4 Beds ⋅ 4 Baths
Welcome to an extraordinary custom-built all-brick estate nestled on five beautifully manicured acres in the highly sought-after Apple Pie Ridge area. This exceptional property blends timeless elegance, quality craftsmanship, and modern updates to create a truly one-of-a-kind retreat. From the moment you arrive, the winding approach and picturesque setting set the stage for what's inside. Designed for both grand entertaining and everyday comfort, the home features three spacious bedrooms, three full bathrooms, and two half baths, with flexible living spaces that can easily accommodate a bedroom, guest suite, or recreation room. The heart of the home is the spectacular gourmet kitchen, where culinary enthusiasts will appreciate granite countertops, a commercial-size refrigerator, two Wolf wall ovens, a cooktop with downdraft ventilation, an expansive multi-level island with prep sink, and instant hot water. The kitchen flows effortlessly into the inviting family room with custom built-ins and a cozy gas fireplace, while the adjoining sunroom fills the home with natural light and offers panoramic views of the backyard oasis. Outside, resort-style living awaits. The inground pool is the centerpiece of the backyard, creating the perfect setting for relaxing afternoons, gatherings, and unforgettable summer entertaining. A brick patio overlooks the beautifully landscaped grounds, offering a peaceful space to unwind and enjoy the privacy of your surroundings. The primary suite is a private sanctuary complete with its own gas fireplace, cedar-lined walk-in closets with custom built-ins, and an impressive spa-inspired bath featuring a jetted soaking tub and separate shower. Additional bedrooms are generously sized, while a spacious office with custom built-ins provides the ideal work-from-home space. A large bonus room with a full bath offers endless possibilities and the fourth-floor bedroom is an incredible private retreat that any teenager or overnight guest will love. Movie nights become an event in the dedicated theater room, while the expansive unfinished basement offers tremendous potential for additional finished living space, a home gym, workshop, or recreation area. Car collectors, hobbyists, and outdoor enthusiasts will appreciate the attached and detached garages with room for up to six vehicles. The detached heated and cooled three-bay garage includes a full bath, separate septic system, and unfinished space above offering endless possibilities. This meticulously maintained home has been thoughtfully updated with two new HVAC systems, a new hot water heater, a new water softener, a new dishwasher, and a new washer and dryer. The original portion of the home also features premium Andersen windows with upgraded screens, enhancing both energy efficiency and timeless appeal. Properties of this caliber rarely become available.

194 Glendobbin Ln, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$675,000
5 Beds ⋅ 3 Baths
Spacious ranch home on a beautiful 1-acre lot in the highly desirable Stonebrook Farms community! Surrounded by mature trees and offering a peaceful setting, this home combines the space of country living with the convenience of being just minutes from shopping, dining, medical facilities, and all that Winchester has to offer. Designed with flexibility in mind, this home features 5 bedrooms and 3 full baths, including a private wing tucked behind the garage with a bedroom, full bath, and adjoining den. Located just off the kitchen, this space is ideal for an in-law suite, guest quarters, home office, or multi-generational living. The finished lower level provides even more living space with an additional bedroom, full bath, kitchen, and dining area, creating endless possibilities for recreation, extended family, or entertaining. Step outside to enjoy the spacious backyard, mature landscaping, and patio, offering plenty of room to relax, garden, or host gatherings. Stonebrook Farms is one of Winchester's most sought-after neighborhoods, offering the opportunity to join the optional Stonebrook Club, featuring swimming, tennis, pickleball, and social activities. With its combination of generous living space, a beautiful setting, and an exceptional location, this home is ready for its next chapter.

146 Stonebrook Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$400,000
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
$799,000
4 Beds ⋅ 4 Baths
Situated on nearly 3 acres of peaceful, private land, 4241 Cedar Creek Grade offers a truly remarkable retreat framed by sweeping, 360-degree views of rolling hills and lush greenery. The exterior commands immediate curb appeal, highlighted by an impressive covered front porch with pillars, a well-manicured lawn, a wide driveway, and an attached three-car garage. Inside, the main level features high-end finishes like pristine hardwood floors and detailed crown molding throughout. A stately formal living room boasts elegant lunette windows, while the separate formal dining room showcases classic wainscoting and tray ceilings. At the heart of the home, the gourmet kitchen shines with upgraded countertops, maple cabinetry, a breakfast bar for additional seating, and stainless steel appliances. It seamlessly flows into a light-filled family room anchored by built-in storage and a cozy gas fireplace, extending into a captivating sunroom where vaulted wooden ceilings and wall-to-wall windows frame uninterrupted, panoramic views of the countryside. A convenient half bath completes the main floor. Upstairs, the expansive primary suite serves as a restful haven, featuring morning views, tray ceiling, a large walk-in closet, and a spa-like ensuite bath equipped with double sinks, a walk-in steam shower, and a relaxing corner soaking tub. Two additional bedrooms share a full bath, while a massive bonus room with its own attached full bath provides endless possibilities as a spacious fourth bedroom, recreation room, playroom, home office or gym. A dedicated upper-level laundry room adds ultimate everyday convenience. Additionally, the full unfinished walkout basement includes rough-in plumbing offering the perfect blank canvas for future expansion, while Glofiber high-speed internet ensures seamless connectivity throughout the property. Beyond the interior, the property unfolds into an extraordinary outdoor oasis built for lavish entertaining. Unwind in the private hot tub on the deck, dine alfresco on the patio, or relax under the cool shade of the covered gazebo—all set against the backdrop of a level, sprawling yard and picturesque scenery. This is more than just a home; it is a private sanctuary offering a lifestyle of unmatched tranquility and effortless luxury just minutes from town.

4241 Cedar Creek Grade, Winchester

Listing courtesy of Colony Realty. Contact:

$799,900
3 Beds ⋅ 3 Baths
Beautifully renovated 1918 farmhouse situated on 10 scenic acres with views of Opequon Creek, accessible creek frontage, a picturesque pond, and some fenced acreage. Conveniently located approximately five miles from downtown Winchester with easy access to shopping, dining, entertainment, Jim Barnett Park, the Trails at the Museum of the Shenandoah Valley, and Rose Hill Park within walking distance. This 3-bedroom, 2.5-bath home blends historic character with modern updates. The remodeled kitchen features new cabinetry, granite countertops, and stainless steel appliances. All bathrooms have been updated with new vanities, tile flooring, lighting, tubs, showers, toilets, and mirrors. Original hardwood floors, stairs, and wood trim have been refinished, while additional improvements include new windows, three exterior doors, fresh interior paint, updated lighting, outlets, ceiling fans, a new roof, and a renovated upper porch with new flooring, ceiling, and railings. Major updates include replaced water and drain lines to the kitchen and bathrooms, replacement boiler for the first-floor oil heat, second-floor HVAC systems and ductwork (2019), electric water heater (2019), new septic distribution box with a completed 8/2026 septic inspection, replacement Permacast front porch columns, updated gutters with gutter guards (2020), and a newer basement steel entry door (2019). The detached garage has also been renovated with a new roof, gutters, fascia, soffit, overhead door and opener, entry door, and concrete floor. A new brick paver walkway and landscaping complete this move-in-ready property, offering the perfect combination of acreage, water views, and modern updates just minutes from Winchester. Chimney Disclosure: All chimneys convey as-is. The chimney behind the kitchen has been permanently sealed and is not functional. The living room chimney is lined for use with a wood or pellet stove. The rear porch chimney serves the boiler heat system. The garage chimney is capped; the cap may be removed if desired. *Agent is related to owner* The information contained herein is for informational purposes only. RE/MAX Roots makes no representation as to the accuracy or reliability of the information. The buyer is to verify information provided and related to the property that is material to a buyer’s decision to purchase the property. All documents and other information attached to this listing are provided as a courtesy and should be researched and verified by the buyer agent.

2122 Jones Road, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$360,000
3 Beds ⋅ 2 Baths
NEW CONSTRUCTION built by a trusted local builder with over 20 years of experience! This beautifully crafted 3-bedroom, 2-bath ranch home offers the perfect blend of quality construction and modern finishes. Built using the ZIP System® exterior sheathing for enhanced weather protection and durability, this home was designed with attention to detail from the ground up. Inside, you’ll find an open-concept floor plan featuring luxury vinyl plank flooring throughout, soft-close cabinetry, stainless steel appliances, and a spacious center island that anchors the kitchen and living area. The private primary suite includes a full bath, while two additional bedrooms and a second full bath provide comfortable living for family or guests. The unfinished basement is equipped with a rough-in for a future full-bath and offers limitless potential! Step outside onto the rear deck overlooking a wooded backdrop and enjoy the peaceful setting. The full walkout basement offers an additional 1,232 square feet ready for storage, a workshop, or future finished living space. The covered front porch, sizable back deck and thoughtful craftsmanship complete this exceptional new home. Enjoy the benefits of mountain living with community amenities including lake access, walking trails, picnic areas, playgrounds, and recreational courts—all while remaining within a convenient drive of Winchester. Why settle for someone else’s worn finishes when you can enjoy the confidence and peace of mind that comes with brand-new construction? Schedule your private showing today!

302 Pheasant Dr, Winchester

Listing courtesy of Virginia Real Estate. Contact: 5406452999
$280,000
3 Beds ⋅ 1 Baths
Recently renovated and move-in ready! This updated 3-bedroom, 1-bath home offers the perfect combination of modern finishes and worry-free living with major upgrades already completed. Enjoy peace of mind with a new roof, new windows, new siding, and a brand-new HVAC system, providing comfort and energy efficiency for years to come. Inside, you'll find stylish luxury vinyl plank (LVP) flooring throughout, creating a seamless and low-maintenance living space. The updated kitchen features all-new stainless steel appliances, offering both functionality and a sleek, contemporary look that's ready for everyday living or entertaining. Conveniently located on N. Frederick Pike with easy access to shopping, dining, schools, and commuter routes, this home is an excellent opportunity for first-time buyers, those looking to downsize, or anyone seeking a turnkey property. Don't miss your chance to own this beautifully renovated home, schedule your private showing today!

2810 N Frederick Pike, Winchester

Listing courtesy of Weichert Realtors - Blue Ribbon. Contact: 3042628700
$409,900
3 Beds ⋅ 3 Baths
Discover this well-appointed 3-bedroom, 3-bathroom single-family home offering approximately 2,150+ square feet of comfortable living space on a generous 0.44-acre lot. Designed with an open floor plan and practical updates, this residence balances everyday convenience with flexible living options in a highly accessible Winchester location. Main Level: Hardwood flooring flows through the open living areas, creating a bright and inviting atmosphere ideal for both daily living and entertaining. The primary suite features a walk-in closet and private full bathroom. Two additional bedrooms share a full hallway bathroom. Finished Lower Level: The finished basement expands the home’s functionality with a full bathroom, dedicated office, and versatile den—perfect for remote work, a media room, guest space, or family activities. Walk-out access leads directly to the deck. Outdoor Living & Parking Enjoy a walk-out deck overlooking a large backyard, ideal for outdoor dining, recreation, or simply relaxing. A two-car attached garage provides convenient parking and storage. Location & Neighborhood Amenities Situated in a convenient Winchester location with easy access to major routes including I-81, Route 37, and Route 11. Residents enjoy proximity to the charm of Old Town Winchester and its walkable Loudoun Street Pedestrian Mall, filled with local shops, restaurants, and historic character. Nearby amenities include shopping centers, Jim Barnett Park with trails and recreational facilities, the Museum of the Shenandoah Valley, and everyday conveniences. The area also offers access to outdoor recreation throughout the Shenandoah Valley while remaining close to major employers and services. This home combines comfortable main-level living, flexible lower-level space, and a private outdoor setting in a location that supports both convenience and lifestyle. Ideal for those seeking space to grow while remaining connected to everything Winchester has to offer.

101 Fay St, Winchester

Listing courtesy of Fairfax Realty Premier. Contact: 3014399500
$598,895
3 Beds ⋅ 4 Baths
Enjoy the ease of true main-level living in this meticulously maintained ranch home offering more than 4,300 finished square feet on an oversized 0.37-acre lot in Winchester's desirable Star Fort community | NO HOA | With nearly 2,300 square feet on the main level and an additional 2,100+ finished square feet in the walk-out basement, this home offers an abundance of flexible living space, all complemented by breathtaking panoramic valley views from the expansive 63-foot deck | Covered Front Porch Leads to Welcoming Foyer | Spacious Dining Room w/Triple Window has Room for a Crowd as does the 17' x 15' Family Room w/Gas Fireplace | Immaculate Kitchen w/Updated Appliances, Recessed Lighting, Pantry & Breakfast Nook w/Sliding Doors to Deck | Main Level Primary Suite w/2 Huge Walk-In Closets + French Doors to the Deck + En Suite Bath with Walk-In Jetted Soaking Tub & Separate Shower | 2 Additional Bedrooms w/Great Closet Space on Main Level Share the 2nd Full Bath + 13' x 12' Flex Room for Guests or Home Office | Convenient Main Level Laundry/Mudroom + 2-Car Side-Load Garage | Fully Finished Walkout Basement has Tremendous Space for Anything! 35' x 33' Rec Room w/Built-in Cabinet Storage + 2 Additional Rooms (27' x 16' & 27' x 26') with Endless Possibilities + 3rd Full Bath | Delightful Fenced Back Yard + Covered Storage Under Deck | Numerous recent improvements including Painted Porch/Lead Walk, Interior Paint, New Flooring + Carpet/Padding & Updated Kitchen Appliances as well as a Resealed Deck (2026) + Replaced Deck Surface (2024), New Attic Insulation (2025), New Insulated Garage Door (2023), New Roof (2018), Washer & Dryer (2018/2017) Additional features include a whole-house generator, whole-house water softener, invisible fence + fully fenced back yard, and walk-in bathtub | Fantastic Winchester Location Convenient to Old Town Winchester & 81 + Shopping, Dining & Recreation

142 Fortress Dr, Winchester

Listing courtesy of RE/MAX Distinctive Real Estate, Inc.. Contact: (703) 858-9108
$115,000
Ever dreamed of owning your own private A-frame cabin in the woods? Whether you're searching for the perfect weekend retreat, a unique short-term rental opportunity, or a peaceful getaway to enjoy with family, friends, or clients, this charming mountain cabin is full of potential. Tucked away in a quiet, wooded setting with easy year-round access, this hidden gem offers the perfect balance of privacy and convenience. Relax on the spacious front deck surrounded by mature trees with peaceful wooded views, or unwind on the rear deck while taking in breathtaking long-range mountain views that truly feel like a million-dollar backdrop. Inside, you'll find a cozy A-frame cabin that is being sold furnished. The current owner has enjoyed it as a weekend getaway, and it's ready for the next owner to complete the vision and create their own mountain retreat. The loft provides additional sleeping space while maintaining the classic A-frame design. Located approximately 30 minutes from Historic Downtown Winchester, about 30 minutes from Front Royal, and roughly 1½ hours from Fairfax, this property is close enough for an easy weekend escape while feeling worlds away from the hustle and bustle. Residents enjoy low real estate taxes, low HOA dues, and community amenities including a scenic pond and waterfall. As more homes continue to be built throughout the community, this peaceful mountain neighborhood is quickly becoming a hidden gem with strong future potential. Property is being sold furnished and strictly As-Is.

403 Stag Trl, Winchester

Listing courtesy of Colony Realty. Contact:

$650,000
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
3 Beds ⋅ 2 Baths
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
3 Beds ⋅ 1 Baths
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
$969,000
5 Beds ⋅ 4 Baths
A rare opportunity to live on Lake Serene - Welcome to your private waterfront retreat on Lake Serene, where resort-style outdoor living meets timeless modern craftsmanship. Rarely does an opportunity like this come along. Tucked among the trees on one of Frederick County's most sought-after private lakes, this beautifully renovated waterfront home offers the perfect balance of luxury, recreation, and everyday comfort. Completely transformed in 2016 with a 2-story addition along with thoughtful updates & remodeling, the home features a stunning custom Chef's kitchen with rich cherry cabinetry, elegant soapstone countertops, and quality finishes include KitchenAid gas range and Viking range hood. Designed for gathering with family and friends we have 5 bedrooms and 3.5 beautifully remodeled bathrooms, numerous living areas on two spacious levels making this THE gathering place! Offering one level living for all daily activity the main level is host to gorgeous family room with soaring ceilings, kitchen, dining room, living room with fireplace, laundry, 3 bedrooms & 2.5 baths. The lower level offers additional space to spread out with game room, recreation room, wet bar and two additional bedrooms and storage. Step outside and discover your own private retreat. Extensive hardscaping, an oval in-ground heated pool, multiple outdoor entertaining spaces, and mature landscaping create a resort-like setting that's perfect for summer afternoons or evening sunsets with views of the lake. A detached 2-bay garage also has a finished area w/ fireplace which was originally utilized as an office now acts as a pool house. Life at Lake Serene is about more than the home itself. Enjoy boating, kayaking, fishing, paddleboarding, or simply relaxing by the water. Inventory on Lake Serene is exceptionally limited, with many properties remaining in the same families for generations. Even more uncommon is finding a home that has already been tastefully updated—allowing you to begin enjoying the lake lifestyle immediately instead of planning years of renovations. Whether you're searching for a full-time residence or the ultimate weekend escape, this exceptional waterfront property offers a rare opportunity to own one of the area's most desirable lake homes. Come experience why life is simply better at Lake Serene.

485 Lake Serene Dr, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$385,000
3 Beds ⋅ 2 Baths
New construction one-level home on a spacious 1-acre lot! Currently under construction and anticipated to be completed in early October 2026, this thoughtfully designed 3-bedroom, 2-bath ranch offers the ease of single-level living with an open-concept floor plan, luxury vinyl plank flooring, granite countertops, upgraded stainless steel appliances, and an attached two-car garage. The open kitchen flows seamlessly into the dining and living areas, creating a bright, welcoming space that's ideal for everyday living and entertaining. The private primary suite, spacious secondary bedrooms, modern finishes, and abundant cabinet space combine comfort, style, and functionality throughout the home. Whether you're buying your first home, downsizing, retiring, or simply looking for the convenience of one-level living, this home offers a comfortable, low-maintenance lifestyle on a beautiful 1-acre lot with room to enjoy the outdoors. Construction is anticipated to be completed in early October 2026. Buyers may still have the opportunity to make certain finish selections, depending on the stage of construction. Contact the listing agent for current construction updates, available selections, and additional details. Taxes currently reflect the land only.

300 Panther, Winchester

Listing courtesy of Preslee Real Estate. Contact: 5402274416
$235,000
2 Beds ⋅ 2 Baths
This home includes two bedrooms, each with an attached bathroom, and is over 1,500 square feet. It features an open floor plan with cathedral ceilings, exposed beams, and hardwood floors. The front family room boasts winter mountain views. The rear sunroom is perfect for enjoying the backyard wildlife. Shawneeland offers a private community beach, lake, playgrounds, and trails. The property was built before 1978; lead-based paint may be present.

114 Inca Trl, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$635,690
3 Beds ⋅ 4 Baths
Rare Dual Primary Suites on the Main Level! Backing to trees, this stunning new Matisse at Hiatt Pointe at Snowden Bridge offers the perfect blend of comfort and flexibility for active adults 55+. Personalize your finishes and move in this spring! Enjoy a gourmet kitchen with SS appliances including hood, quartz countertops, an oversized island, and walk-in pantry. The open layout features 10' ceilings, a gas fireplace, and a screened porch overlooking the wooded homesite. The finished lower level adds a rec room, third bedroom, and full bath. Enjoy resort-style amenities including a gated entrance, clubhouse, fitness center, pickleball, bocce, pool, and hot tub. Ask about builder incentives!

3168 Ruby Royce Dr, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322
$622,490
3 Beds ⋅ 3 Baths
MOVE-IN READY and designed for Active Adult (55+) living, this never lived-in before SINGLE FAMILY HOME offers main-level living and low-maintenance design at Hiatt Pointe, a gated community in Winchester, VA. Experience a true RESORT-STYLE lifestyle with exceptional onsite community amenities including a clubhouse, fitness center, pickleball and bocce courts, pool and hot tub, yoga studio, outdoor kitchen, fireside lounge, wine lockers, walking trails, and more. A full calendar of resident activities, from water aerobics and Mahjong game nights to Friday happy hours, creates endless opportunities to stay active, socialize, and enjoy everything Hiatt Pointe by Van Metre Homes has to offer! -----Spanning 3,200 finished square feet, this two-level single family home welcomes you with a covered front porch, 9ft. ceilings, and Luxury Vinyl Plank (LVP) flooring throughout the entire main level. Homesite 1014 features three bedrooms, three full bathrooms, and a finished two-car front-load garage. At the heart of the home, the kitchen features granite countertops, soft-close cabinetry, an oversized island, a walk-in pantry with solid shelving, and Samsung® stainless steel appliances. Enjoy a walkout deck off the great room for seamless outdoor living. The open-concept main level includes a spacious great room with an electric fireplace, a dedicated dining area, a secondary bedroom, and a luxurious primary suite. The primary bath has dual vanities and a roll-in frameless shower with floor-to-ceiling tile. A second full bath, family foyer with access to the laundry room, pantry, and two-car garage, complete the main level. The finished attached garage includes an electric opener and exterior keypad, while the home is solar-ready for future energy upgrades. The walkout finished basement adds a bedroom, full bath, and spacious rec room ideal for guests, entertaining, or flexible living. Being a new build, your home is constructed to the highest energy efficiency standards and comes with a post-settlement warranty. This home offers available closing cost assistance when financing with Intercoastal Mortgage and closing with Walker Title. -----Hiatt Pointe (55+) is located in Frederick County with convenient access to historic Downtown Winchester, Route 7, I-81, and I-66. Nearby shopping and dining includes Rutherford Crossing (4 mins away), Apple Blossom Mall (11 mins away), Downtown Winchester (13 mins away), and Winchester Commons (14 mins away). -----This home is available for self-guided touring through NterNow, no agent or appointment required. Buyers may visit independently during daylight hours. Scan the QR code at the door for instant access and follow a few quick prompts to let yourself in. For more information, visit our website or call Van Metre Homes. -----*Other homesites and delivery dates may be available. Pricing, offers, and availability are subject to change without notice. Images, renderings, and site plans are for illustrative purposes only and may not reflect actual homes or features. Some images and renderings may depict interior designs created in collaboration with AI or may represent a similar home. Additional terms and conditions may apply. Please see a Van Metre New Home Advisor for details.

134 Wagtail Ln Unit #HOMESITE 1014, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
$644,490
6 Beds ⋅ 6 Baths
6-bedroom, 5.5-bath Monroe sits on a desirable cul-de-sac in Snowden Bridge and is still under construction, giving you time to select your own cabinets, countertops, and flooring. The main level features a convenient guest suite. The kitchen boasts Gourmet Stainless Steel Appliances with hood, quartz counters and a farmhouse style sink. Oak stairs lead to the 2nd level. The primary suite has 2 walk in closets, and the ensuite offers dual vanities and shower with frameless door. 3 secondary bedrooms and 2 additional baths are found on the upper level along with the convenient laundry room. Walkout lower level with 9' foundation walls, comes finished with recreation room, bedroom and full bath, making this the perfect place to call home. Snowden Bridge is a premier master-planned community with exceptional amenities including a swimming pool, pirate water park, indoor sportsplex, community park, fenced in dog park, and playground. In addition, there is a bike track, walking trails, and a picnic pavilion. You won’t have to leave to have fun, but when you do you’re just minutes from all the convenience and entertainment around Winchester. Ask about builder incentives! Please note the photos are of a similar home while under construction.

2484 Scotch Bonnet Dr, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322
$399,000
3 Beds ⋅ 2 Baths
Situated directly across from historic Third Battle of Winchester Park, this charming brick ranch offers a rare opportunity to enjoy more than six miles of scenic walking trails, interpretive markers, and historic monuments just steps from your front door. Conveniently located with quick access to Routes 7, 11, and I-81, the property combines peaceful surroundings with exceptional accessibility. Set on approximately 2.37 mostly level, usable acres, the property provides plenty of space for gardening, outdoor recreation, or future expansion. The home features more than 1,300 square feet of living space on the main level, plus an additional 1,300-square-foot basement, offering endless possibilities. Inside, you'll find three bedrooms, one and half bath's, and original hardwood floors in the family room and bedrooms, all ready for your personal updates and finishing touches. The full walk-out basement, with its separate exterior entrance, expands the home's potential for additional living space, a recreation room, home office, or workshop. Partially finished and previously used as a recreation area, it also includes a large unfinished section with built-in shelving for exceptional storage or hobby space. Owned by the same family since it was built, this well-constructed home features a timeless brick exterior, an attached carport, a spacious rear deck, and several outbuildings ideal for storing lawn equipment, gardening tools, or outdoor gear. With solid construction, a functional layout, beautiful acreage, and an unbeatable location across from one of the area's most treasured historic parks, this property is brimming with potential and ready for its next chapter. Whether you're looking for a peaceful place to call home or an opportunity to create your dream property, this is one you won't want to miss.

735 Redbud, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$775,000
4 Beds ⋅ 4 Baths
Welcome to this exceptional 4-bedroom, 3.5-bath Colonial in the sought-after Raven Pointe subdivision, where luxury living extends well beyond the front door. The backyard is a true showstopper, featuring a one-year-old 20' x 40' heated Hayward OmniLogic saltwater pool with a tanning ledge, sunken spa, and Coverstar automatic safety cover. A covered Trex deck with a porch swing overlooks the private backyard, creating the perfect space for relaxing or entertaining. Inside, the main level offers a private home office with custom built-ins, a formal dining room, a spacious family room with a gas fireplace, and a beautifully appointed kitchen featuring a large center island, butler's pantry, stainless steel appliances, gas cooking, and a bright breakfast room. Upstairs, the spacious primary suite includes luxury vinyl plank flooring, a walk-in closet, and a spa-like bath with a jetted tub, walk-in shower, and dual vanities. Three additional bedrooms, a versatile bonus room, and an upper-level laundry room complete the second floor. The finished walk-up basement is made for entertaining with a large recreation room, wet bar with a built-in ice maker, full bath, storage room, and a flexible bonus room that can serve as a fifth bedroom, home gym, or office. Located in Raven Pointe with sidewalks and streetlights, this home is just minutes from shopping, dining, schools, and commuter routes. Offering an incredible combination of elegant living spaces and a resort-style backyard, this is a home you won't want to miss.

107 Cahille Dr, Winchester

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