Winchester, VA Homes for Sale

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  $399,000

  • Land
  • 3,920 Sq Ft
  • $4,433,333 per Acre

  1 N Braddock St, Winchester, VA 22601

  Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and

  Gillian Greenfield Coldwell Banker Premier

  1 N Braddock St, Winchester, VA 22601
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  /96

  $535,000

  • 4 Beds
  • 2.5 Baths
  • 3,258 Sq Ft

  118 Marlise Ln, Winchester, VA 22602

  118 Marlise Ln is a residence with a functional layout and comfortable living spaces throughout. The kitchen features stainless steel appliances and an accent backsplash, creating a well-equipped space for cooking and entertaining. The primary bathroom includes double sinks for everyday convenience and a separate tub and shower. A deck extends the living space outdoors, flowing to a fully fenced

  Jacqueline Moore Open Door Brokerage, LLC

  118 Marlise Ln, Winchester, VA 22602
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  /34

  $350,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  411 Cardinal Dr, Winchester, VA 22602

  Back on the market at no fault of the seller or the property. The previous buyer was unable to satisfy their home sale contingency, creating a new opportunity for interested buyers. Schedule your showing today!Welcome to 411 Cardinal Dr., a newly completed home offering 3 bedrooms, 2 bathrooms, and thoughtfully designed one-level living. This property features an open layout with durable

  Abby Walters Preslee Real Estate

  411 Cardinal Dr, Winchester, VA 22602
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  /30

  $385,000

  • 3 Beds
  • 1 Bath
  • 1,280 Sq Ft

  540 Bellview Ave, Winchester, VA 22601

  Attention investors! Charming rambler just minutes from historic Old Town Winchester with convenient access to I-81, making commuting simple and stress-free. This inviting home features beautiful hardwood floors, a spacious living room with a cozy fireplace, and a formal dining room perfect for hosting family and friends. The kitchen offers easy access to the backyard, creating a seamless flow

  Heloisa Amar Samson Properties

  540 Bellview Ave, Winchester, VA 22601
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  /31

  $499,900

  $60K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,068 Sq Ft

  110 Russelcroft Rd, Winchester, VA 22601

  Nestled in the established Cedarmeade community, this beautifully updated 4-bedroom, 3-bath ranch home offers the perfect combination of comfort, style, and functionality. With over 2,000 square feet of finished living space, this home is designed to accommodate both everyday living and effortless entertaining.Step inside to find warm hardwood flooring, abundant natural light, and

  Grace Mooney Coldwell Banker Premier

  110 Russelcroft Rd, Winchester, VA 22601
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  /2

  $250,000

  • Land
  • 5 Acres
  • $50,000 per Acre

  341 Laurel Grove Rd, Winchester, VA 22602

  THERE ARE 2 -5 ACRE BUILDING LOTS W/4 BR CONVENTIONAL PERKS APPROVED. LOT 3 IS UP ON THE HILL AND LOT 4 FRONTS THE ROAD. THESE LOTS ARE CREATED FROM A LARGER PARCEL BY WAY OF A BOUNDRY LINE ADJUSTMENT. NEW PLATS AND BOUNDRY LINE ADJUSTMENTS INCLUDED IN DOCUMENTS. NEW DEEDS WILL BE ISSUED AT CLOSING. TAX ASSESSMENTS AND TAXES ARE BASED ON THE ENTIRE PROPERTY PRIOR TO BOUNDRY LINE ADJUSTMENT. NEW

  Barbara Singhas Crum Realty, Inc.

  341 Laurel Grove Rd, Winchester, VA 22602
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  /2

  $24,900

  • Land
  • 20,473 Sq Ft
  • $52,979 per Acre

  Lot 162 Bobcat Trail, Winchester, VA 22602

  Imagine creating your own mountain getaway atop Great North Mountain. Tucked among the trees in Shawneeland, this just-under-half-acre lot offers a peaceful wooded setting, privacy, and the potential for beautiful westerly mountain views.The property includes a relatively level area that may offer possibilities for a future homesite. With thoughtful planning and clearing, envision a cozy

  Natasha Roberts Realty ONE Group Old Towne

  Lot 162 Bobcat Trail, Winchester, VA 22602
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  $760,000

  • 5 Beds
  • 4.5 Baths
  • 4,438 Sq Ft

  769 Seldon Dr, Winchester, VA 22601

  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. Create wealth with this income producing opportunity.The main level features a generously sized

  Amanda Slate Keller Williams Realty

  769 Seldon Dr, Winchester, VA 22601
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  /12

  $598,990

  New Construction

  • 3 Beds
  • 2 Baths
  • 3,056 Sq Ft

  TO BE BUILT-HOMESITE Williamson Rd, Winchester, VA 22602

  TO BE BUILT – This home has not been constructed yet. Photos are of a similar model and may show optional features. Appointment at model home – 154 Williamson Rd. Price reflects base price plus options. Estimated delivery timeline is approximately 6–7 months. The Drexel offers generous living space in a beautifully designed ranch home featuring 3 bedrooms and 3 bathrooms, with approximately 3,213

  Greta Fernandez New Home Star Virginia, LLC

  TO BE BUILT-HOMESITE Williamson Rd, Winchester, VA 22602
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  /46

  $360,000

  $10K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,362 Sq Ft

  300 Elk Trail, Winchester, VA 22602

  Looking for a newer home with room to spread out and a peaceful wooded setting? Welcome to 300 Elk Trail.Built in 2021 and tucked among the trees in the Mountain Falls/Wilde Acres area, this 4-bedroom, 3-bath home offers the perfect blend of modern convenience and country living. The open main level creates a welcoming space for gathering with family and friends, while the finished lower

  Abby Walters Preslee Real Estate

  300 Elk Trail, Winchester, VA 22602
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  /10

  $750,000

  • Studio
  • 3,484 Sq Ft

  224 Sharp St, Winchester, VA 22601

  Rare Historical Winchester Investment Opportunity – Three Properties in One LocationAn outstanding investment opportunity awaits in the heart of Winchester City. This unique portfolio comprises three properties positioned along the same street, offering exceptional potential for developers, investors, or those seeking a landmark project for multi-unit rentals or commercial development. Both

  Stacey Rowe Real Broker LLC

  224 Sharp St, Winchester, VA 22601
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  $715,000

  • 3 Beds
  • 4 Baths
  • 2,931 Sq Ft

  336 Apple Valley Rd, Winchester, VA 22602

  Spacious contemporary craftsman style home built in 2007 on .5 acre lot with rare 3 car attached side load garage as well as a detached 2 car & 1 car garages behind the home. This is a car lover's dream with a total 6 garaged parking spaces as well as the driveway or perfect for home based business (with appropriate County approval) - NO HOA!!! Located next to the green space of Kernstown

  Sandra Brill Century 21 Redwood Realty

  336 Apple Valley Rd, Winchester, VA 22602
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  /8

  $2,286,000

  • Land
  • 5.08 Acres
  • $450,000 per Acre

  0 Market St Unit VAFV2004914, Winchester, VA 22602

  5.08 Acres zoned B-2 in Rutherford Crossing shopping center. Owner will consider subdivision of the property. Directly across from Lowes and Target and next to Spring Hill Marriot Hotel and Suites and FEMA call center. Ideal for hotels, restaurants, office buildings, retail, etc... John Schroth and John Scully, owners are licensed Realtors in the state of Virginia.

  John Schroth Colony Realty

  0 Market St Unit VAFV2004914, Winchester, VA 22602
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  $260,000

  • 2 Beds
  • 1.5 Baths
  • 1,068 Sq Ft

  103 E Germain St, Winchester, VA 22601

  Welcome to 103 E Germain St, a charming end-of-row townhouse just blocks from downtown Winchester! Enjoy easy access to restaurants, shops, breweries, entertainment, and historic attractions while enjoying low-maintenance living. The bright main level features an open floor plan, beautiful hardwood flooring, a spacious living room, kitchen, and dining area, plus a convenient half bath. Upstairs

  RoxAnn Grimes RE/MAX Roots

  103 E Germain St, Winchester, VA 22601
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  $340,000

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft

  197 Denny Ln, Winchester, VA 22603

  Charming 3-bedroom, 2-bathroom cottage located off Berryville Ave. This inviting home features a large fully fenced back yard complete with a firepit, perfect for outdoor gatherings and relaxation.On the main level, you'll find two cozy bedrooms, kitchen with stainless appliances and a living room with shiplap accent wall. Upstairs, the spacious primary suite awaits, boasting a large dual

  Amanda Whitson Realty ONE Group Old Towne

  197 Denny Ln, Winchester, VA 22603
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  $784,900

  $5K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 5,310 Sq Ft

  118 Aulee Ct, Winchester, VA 22602

  This beautiful, well-cared-for home occupies a peaceful setting overlooking a lake and stream directly behind the house. The well-stocked lake has an easily accessible walking trail near the back of the house. The owners have painted the entire interior and added new lighting fixtures, blinds, and window treatments, all of which convey. The main-floor half bath has new wallpaper, a new vanity &

  George Glaize George W. Glaize, Jr., Inc. REALTOR

  118 Aulee Ct, Winchester, VA 22602
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  $429,000

  • 4 Beds
  • 2 Baths
  • 1,844 Sq Ft

  1310 Whittier Ave, Winchester, VA 22601

  Turn-key and move-in ready! This beautifully updated 4-bedroom, 2-bath home features a modern kitchen with recently updated appliances, a new HVAC system, and a new hot water heater for added peace of mind. Enjoy the spacious backyard, perfect for outdoor entertaining, along with convenient off-street parking and the freedom of no HOA. Nestled in an established neighborhood with large yards and a

  Sarah Hott Realty ONE Group Old Towne

  1310 Whittier Ave, Winchester, VA 22601
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  $539,000

  Open Sat 11AM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 2,884 Sq Ft

  111 Sovereign Ct, Winchester, VA 22602

  Step into the lifestyle you deserve at 111 Sovereign Ct in Freedom Manor! This 3-level, 4-bedroom, 3.5-bath home is crafted for modern living. The main level has an open-concept layout that makes entertaining a breeze. Whether you are hosting a large group or relaxing in the family room, the layout is designed to flow seamlessly. The upper-level primary suite is your personal sanctuary, with

  Kerry & Ed Stinson Berkshire Hathaway HomeServices PenFed Realty

  111 Sovereign Ct, Winchester, VA 22602
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  /56

  $899,000

  Open House 10/03 Coming Soon Sep 1

  • Land
  • 152.44 Acres
  • $5,897 per Acre

  TRACT 1: 152.44+/- A Off of Laurel Grove Rd, Winchester, VA 22602

  152± BEAUTIFUL ACRES IN WINCHESTER, VA! This outstanding property offers an incredible opportunity to build your dream home, cabin, or private retreat. The property features beautiful views, a cleared building site, an approved five-bedroom perc site, and electric has been run to the property, providing an excellent foundation for future development. Outdoor enthusiasts will appreciate the great

  Matthew Hurley Hurley Real Estate & Auctions

  TRACT 1: 152.44+/- A Off of Laurel Grove Rd, Winchester, VA 22602
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  $310,000

  • 3 Beds
  • 2 Baths
  • 1,532 Sq Ft

  204 Cochise Trail, Winchester, VA 22602

  Adorable rancher in Shawneeland with access to a lake, trails, beach, and fishing. Ideally you wish for spacious living quarters,3 bedrooms, 2 full baths, and a walkout basement with a finished room for gym/office/den..well we have all that and more so come take a gander and make it your own before the summer ends.

  Dave Spence RE/MAX Roots

  204 Cochise Trail, Winchester, VA 22602
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  $410,000

  $85K PRICE DROP

  • Land
  • 20 Acres
  • $20,500 per Acre

  000 Light Rd, Winchester, VA 22603

  Gentle stretches of open meadow roll into quiet, wooded groves where sunlight filters through the trees. Hidden among them, peaceful little ponds shimmer like jewels, inviting you to pause and simply breathe. Imagine sundrenched mornings, afternoons exploring your own private trails, and evenings watching the sky glow across wide open fields. Whether you long to build a cozy retreat, a forever

  Melissa Johnston ERA Oakcrest Realty, Inc.

  000 Light Rd, Winchester, VA 22603
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  $359,000

  $16K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,474 Sq Ft

  805 Pennsylvania Ave, Winchester, VA 22601

  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

  Sherry Santmyer Hunt Country Sotheby's International Realty

  805 Pennsylvania Ave, Winchester, VA 22601
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  $320,000

  $30K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  913 Orchard Hill Dr, Winchester, VA 22601

  New roof, new windows, all brick exterior, wood burning fireplace, screened porch. Perfect opportunity for buyers to bring the interior of the property to neighborhood standards and enhance the value through sweat equity. This home has a great floor plan and an enviable location in beautifully maintained, established area. Located with easy access to amenities, shopping and commuter

  Dallas Croft Samson Properties

  913 Orchard Hill Dr, Winchester, VA 22601
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  $389,000

  $9K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,552 Sq Ft

  103 Elaine Dr, Winchester, VA 22602

  This is the one you’ve been waiting for — a beautifully maintained ranch‑style home with thoughtful updates and a bright, comfortable layout throughout. A newer roof, updated HVAC, and fresh carpet provide peace of mind and move‑in readiness from day one.The primary ensuite serves as a true retreat, featuring a spa‑like bath and a walk‑in closet. Two additional bedrooms offer flexible living

  LESLIE WEBB Long & Foster Real Estate, Inc.

  103 Elaine Dr, Winchester, VA 22602
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  /2

  $199,900

  • Land
  • 6,969 Sq Ft
  • $1,249,375 per Acre

  1415 Ramseur Ln, Winchester, VA 22601

  Steve DuBrueler Coldwell Banker Premier

  1415 Ramseur Ln, Winchester, VA 22601
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  /37

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  163 Margaret Ln, Winchester, VA 22603

  (Magnificent Margaret) This home has a lot to offer: All bedrooms and bathrooms on the main level, fully updated kitchen with Stainless Steel Appliances (Fridge, Dishwasher, Stove, Microwave) Quartz counter top, built in pantry, remodeled bathrooms with a double vanity in the primary bathroom and a walk-in tile shower, Central Heating & Air, New windows, Laundry room, large driveway, two car

  Michael Sprague Samson Properties

  163 Margaret Ln, Winchester, VA 22603
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  /12

  $8,900

  • Land
  • 12,632 Sq Ft
  • $30,690 per Acre

  155 Hawk Trail, Winchester, VA 22602

  Looking for affordable land in Shawneeland? Inventory is moving quickly in several sections, making this a rare opportunity to secure a lower‑mountain lot with easy access—ideal for those seeking both convenience and a peaceful, natural setting.This raw land parcel is on a hard surface road in a scenic, mountainous residential community just 12 miles from Winchester, Virginia. Enjoy the fresh

  Rebecca McTavish Long & Foster Real Estate, Inc.

  155 Hawk Trail, Winchester, VA 22602
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  $240,000

  Open Sun 12PM - 2PM

  • 2 Beds
  • 1 Bath
  • 757 Sq Ft

  17 Glaize Ave, Winchester, VA 22601

  Welcome to this charming Winchester home, coming soon!This adorable 2-bedroom, 1-bath property offers 757 square feet of cozy living space and plenty of character. Enjoy the inviting front porch, spacious yard, and convenient location. Whether you’re a first-time buyer, downsizing, or looking for an investment opportunity, this home is worth a look. More details and professional photos coming

  Tina Purcell Pearson Smith Realty, LLC

  17 Glaize Ave, Winchester, VA 22601
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  $995,000

  • Land
  • 43,124 Sq Ft
  • $1,005,051 per Acre

  0 Amoco Unit VAFV2010648, Winchester, VA 22601

  Interstate Commercial Lot for Sale: 1-acre +/- parcel zoned B2 with potential to rezone to B3. Graded pad with all utilities to site. Ideal for restaurant, retail business, etc. Interstate signage opportunity. Neighbors include Sheetz, National Tire and Battery, Highway 55 Burgers and Shakes, and a 78 room Wyndham Microtel Hotel. The area is also home to FEMA, Amazon Distribution Center, Proctor

  Randolph Craun Oakcrest Commercial LLC.

  0 Amoco Unit VAFV2010648, Winchester, VA 22601
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  $339,999

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  113 Windmill Ln, Winchester, VA 22602

  Why rent when you can own? This spacious townhome has everything you are looking for. Located steps away from Route 7 & I Interstate 81, with grocery stores, pharmacy and restaurants. Who needs to go out when you can entertain at home. LARGE rooms, well equipped Kitchen w/ walk-in Pantry & Island, Microwave & Glass Top cooking Range & durable easy to clean Corian Countertops. Kitchen flows to

  Sarah Hott Realty ONE Group Old Towne

  113 Windmill Ln, Winchester, VA 22602
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  $349,900

  • 3 Beds
  • 2 Baths
  • 1,673 Sq Ft

  904 Archwood Trail, Winchester, VA 22602

  "Escape To Archwood" Whether you're looking for a weekend retreat or a primary residence this 3-bedroom, 2-bathroom Chalet Style home is it! With incredible mountain views, privacy and room to stretch out this home can be your happy place! Open concept on the upper level with vaulted ceilings and a large kitchen with stainless steel appliances. Primary bedroom with a sliding door to the deck and

  Matt Kilmer Samson Properties

  904 Archwood Trail, Winchester, VA 22602
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  $489,990

  New Construction $40K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,971 Sq Ft

  251 Rossmann Blvd, Winchester, VA 22602

  The home is vacant, move-in ready, with a full basement, preselected upgrades, and a one-year home warranty. Welcome to this beautifully crafted new home by a respected local builder, offering almost 2,000 square feet of thoughtfully designed living space in the desirable Sovereign Village community, with room to grow in the improved basement. The inviting, open-concept main level features a

  Marisa Varley ERA Oakcrest Realty, Inc.

  251 Rossmann Blvd, Winchester, VA 22602
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  $849,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,512 Sq Ft

  Lot 12 Keval Gyan Way, Winchester, VA 22603

  Four month build time from contract. 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 (Aspen); 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

  Jim Thomson Realty ONE Group Old Towne

  Lot 12 Keval Gyan Way, Winchester, VA 22603
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  $547,000

  $28K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,290 Sq Ft

  114 Settlers Cir, Winchester, VA 22602

  BACK ON THE MARKET AFTER THE INSTALLATION OF NEW CARPET !! MOVE IN CONDITION PRICED TO SELL FAST LOCATED IN THE CUL-DE-SAC WHICH HAS A PLAYGROUND - SEPERATE IN-LAW-SUITE IN BASEMENT WITH SEPARATE ENTRANCE FULL BATH LIVING ROOM OFFICE OR COULD MAKE INTO KITCHEN AREA - JUST FULLY PAINTED THRU-OUT NEW CARPET INSTALLED AND THE HARDWOOD FLOORS LOOK NEW. GAS FIREPLACE - KITCHEN WITH BAR AND TABLE SPACE

  Thomas Dawe Winchester Real Estate Connection

  114 Settlers Cir, Winchester, VA 22602
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  $260,000

  • 2 Beds
  • 1 Bath
  • 997 Sq Ft

  108 Martin Dr, Winchester, VA 22602

  Attention investors! Charming brick rambler situated on a spacious corner lot, just minutes from Route 7 and I-81—an ideal location for commuters. The property offers a driveway and a carport, perfect for convenient parking or doubling as a shaded outdoor space for entertaining, along with generous storage space. Inside, you’ll find an open-concept living room and eat-in kitchen with large

  Heloisa Amar Samson Properties

  108 Martin Dr, Winchester, VA 22602
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  $330,000

  • 4 Beds
  • 2 Baths
  • 1,592 Sq Ft

  805 S Kent St, Winchester, VA 22601

  Very well-maintained 2-level home offering 4 bedrooms and 2 full baths in the heart of Winchester. This home features a functional layout with a blend of classic charm and thoughtful updates throughout. Pride of ownership shows inside and out, with comfortable living spaces, a fully fenced yard, and a private driveway for off-street parking. Conveniently located near downtown, shopping, and

  Carolina Mosquera Weichert, REALTORS

  805 S Kent St, Winchester, VA 22601
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  /17

  $295,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  1314 S Braddock St, Winchester, VA 22601

  1314 S Braddock St is a one-story Winchester single-family home with a functional single-level layout. The kitchen is equipped with stainless steel appliances for everyday cooking and cleanup. The bathroom includes a tub and shower for daily use, and a dedicated laundry area with a stacked washer and dryer keeps utility tasks out of the main living space. Multiple bedrooms provide flexible room

  Jacqueline Moore Open Door Brokerage, LLC

  1314 S Braddock St, Winchester, VA 22601
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  /76

  $725,000

  Open Sat 11AM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 4,636 Sq Ft

  217 Ashland Dr, Winchester, VA 22603

  Welcome home to Ashland Dr! This very well maintained ranch, is simply waiting for you to move in and make your own. From fresh paint throughout, new carpet in the primary bedroom (installed after 3D tour), newly updated kitchen appliances, countertop and backsplash to the extensive 4+ acres, Ashland is perfect for entertaining, creating memories and making the space entirely as you envision.

  Nicole Lewis Coldwell Banker Premier

  217 Ashland Dr, Winchester, VA 22603
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  /38

  $339,000

  Open House 9/13 $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,667 Sq Ft

  204 Cougar Trail, Winchester, VA 22602

  Nestled in the serene Wilde Acres subdivision, this charming split foyer home, built in 2020, offers a perfect blend of modern comfort and natural beauty. With 3 spacious bedrooms and 2.5 bathrooms, this residence is designed for both relaxation and entertaining. Step inside to discover a warm and inviting interior featuring laminated flooring throughout. The heart of the home is the combination

  Gerald Owens Realty ONE Group Old Towne

  204 Cougar Trail, Winchester, VA 22602
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  /28

  $485,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,953 Sq Ft

  PINE Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

  The Pine is a 1,953 square foot open concept home, offering four bedrooms, two and a half bathrooms and a two-car garage. A foyer with a powder room and coat closet greets you as you enter this home. The open floorplan allows you and your loved ones to spend quality time together while in the living room, casual dining area and kitchen. The spacious kitchen has a large island with room for

  D.R. Horton Builder

  137 Seminole Dr Unit 36203779, Winchester, VA 22602

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