Winchester, VA 2-Story Homes for Sale

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  /2

  $519,900

  Coming Soon

  • 4 Beds
  • 2 Baths
  • 2,014 Sq Ft

  502 Fortress Dr, Winchester, VA 22603

  Discover the charm of this stunning Colonial-style home, nestled in a vibrant community that offers the perfect blend of comfort and convenience. Built in 2003, this meticulously maintained residence boasts 2,014 square feet of living space, featuring four spacious bedrooms and two full bathrooms, ideal for creating lasting memories. The heart of this home is its inviting living area, complete

  Sky Raciborski Realty ONE Group Old Towne

  502 Fortress Dr, Winchester, VA 22603
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  /47

  $519,900

  $79K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,837 Sq Ft

  1317 Caroline St, Winchester, VA 22601

  Welcome to 1317 Caroline Street, a well-appointed brick rancher in a fantastic Winchester location that perfectly balances professional convenience with residential comfort. Situated just minutes from Winchester Medical Center and major commuter routes, this home offers an effortless transition from a busy day to a relaxing evening. This sense of ease begins the moment you step inside the main

  Dan Whitacre Colony Realty

  1317 Caroline St, Winchester, VA 22601
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  /46

  $524,990

  New Construction $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,284 Sq Ft

  253 Rossmann Blvd, Winchester, VA 22602

  Contact me to learn how you can receive up to $30,000 in builder-paid closing costs! The home is vacant, move-in ready, and includes pre-selected upgrades and a new-construction warranty. Welcome to this beautifully crafted new home by a respected local builder, offering almost 2,300 square feet of thoughtfully designed living space in the desirable Sovereign Village community. The inviting,

  Marisa Varley ERA Oakcrest Realty, Inc.

  253 Rossmann Blvd, Winchester, VA 22602
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  /39

  $484,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,906 Sq Ft

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

  The Deerfield is a thoughtfully designed home with four bedrooms and two-and-a-half baths. The kitchen features a walk-in pantry and a breakfast island, which includes a sink, making it perfect for food preparation, and has plenty of room for stools, so you can entertain. The kitchen looks out over the open-concept dining area and great room. All four bedroom are upstairs along with the Laundry

  D.R. Horton Builder

  137 Seminole Dr Unit 36203782, Winchester, VA 22602
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  /23

  $542,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,476 Sq Ft

  2465 Saffron Crest Dr, Winchester, VA 22603

  Easy living starts here—and time is running out to move in this year. Construct this thoughtfully designed main‐level living home and have the opportunity to personalize your style with your choice of flooring, cabinets, countertops, and fixtures. The main level features low‐maintenance LVP flooring throughout, vaulted ceilings in the family room, and a spacious primary suite with a deluxe bath

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  2465 Saffron Crest Dr, Winchester, VA 22603
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  /20

  $409,900

  New Construction $10K PRICE INCREASE

  • 3 Beds
  • 3 Baths
  • 1,914 Sq Ft

  103 Tonto Trail, Winchester, VA 22602

  Current Shawneeland Inventory107 Pinto Trail (split foyer)208 Beaver Trail210 Beaver Trail212 Falcon Trail211 Inca Trail116 Pinto Trail103 Tonto Trail123 Killbuck TrailStunning 3BR/3BA home on over 1/3 acre lot with available Xfinity internet (not all streets have it). Easy entrance access. Open floor plan features vaulted family room & kitchen. Upgraded

  Jim Thomson Realty ONE Group Old Towne

  103 Tonto Trail, Winchester, VA 22602
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  /26

  $400,000

  • 5 Beds
  • 2 Baths
  • 1,011 Sq Ft

  605 Dunlap St, Winchester, VA 22601

  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

  Alexandra Brown Spring Hill Real Estate, LLC.

  605 Dunlap St, Winchester, VA 22601
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  /82

  $370,000

  • 3 Beds
  • 1.5 Baths
  • 1,036 Sq Ft

  2431 Cedar Creek Grade, Winchester, VA 22602

  NEW SEPTIC JUST INSTALLED. This is a unique opportunity to purchase a piece of history. The Glass Mill (Glass/Rinker/Cooper Mill) is available. The Mill was constructed during the years 1812-1815. At the base, the structure has stone walls that are 3' thick, tapering to about half that at the gable ends. The Mill has a "mechanics level", the lower level with dirt floor and water source when the

  Edward Beightol Cedar Creek Real Estate

  2431 Cedar Creek Grade, Winchester, VA 22602
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  /97

  $869,000

  $66K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 4,545 Sq Ft

  620 Lake Serene Dr, Winchester, VA 22603

  Classic waterfront home, diligently updated and modernized with quality improvements and thoughtful design from well and septic and new floating dock on the outside, to totally renovated kitchen and primary bedroom suite and baths on the inside. Continue the seller's active lifestyle with the conveyance of a variety of boats and an indoor lap pool. Enjoy the seller's efforts to maintain this

  Dallas Croft Samson Properties

  620 Lake Serene Dr, Winchester, VA 22603
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  /52

  $419,900

  • 3 Beds
  • 2 Baths
  • 2,067 Sq Ft

  1115 Opequon Ave, Winchester, VA 22601

  Well-maintained 3 bed/2 bath rancher just blocks from Jim Barnett Park and close to schools, shopping, dining, and entertainment. Hardwood flooring throughout the main level. Spacious eat-in kitchen with a skylight , featuring Corian countertops, center island, pantry, and additional storage closet. Separate formal dining room. Relax on the 20x6 covered front porch or the 12x16 covered rear deck

  Sheila Pack RE/MAX Roots

  1115 Opequon Ave, Winchester, VA 22601
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  /31

  $519,990

  New Construction

  • 5 Beds
  • 3 Baths
  • 2,415 Sq Ft

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

  Introducing the Elm, a contemporary 2,415 square feet two-story home, featuring five bedrooms, three bathrooms, a loft, and a two-car garage. As you step into the distinct foyer you will appreciate the open concept floorplan. The spacious kitchen boasts an abundance of cabinetry and counter space, an ample walk-in pantry, a large island with room for seating and stainless-steel appliances. The

  D.R. Horton Builder

  137 Seminole Dr Unit 36203780, Winchester, VA 22602
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  /23

  $239,900

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  139 Little River Dr, Winchester, VA 22602

  Nestled in the charming Brookland Heights community, this delightful Colonial townhouse offers a perfect blend of comfort and style. Built in 1989, this home features a warm and inviting atmosphere, ideal for creating lasting memories. Step inside to discover a cozy interior that boasts a thoughtfully designed kitchen with ample table space, perfect for casual dining or entertaining friends. The

  Rebecca Sims Century 21 Redwood Realty

  139 Little River Dr, Winchester, VA 22602
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  /53

  $799,000

  • 4 Beds
  • 3 Baths
  • 3,366 Sq Ft

  135 Kinross Dr, Winchester, VA 22602

  Discover the charm of this beautiful custom Craftsman-style home nestled in the desirable Ravenwing community. Built in 2018, this residence boasts a perfect blend of contemporary design and classic comfort, featuring four spacious bedrooms and three full bathrooms. Step inside to find an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas, ideal for both

  Wendy Conner Coldwell Banker Premier

  135 Kinross Dr, Winchester, VA 22602
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  /89

  $1,139,000

  $111K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,188 Sq Ft

  1015 Redbud Rd, Winchester, VA 22603

  Set on over 10 private acres in the quiet Locust Level Estates community, this beautifully designed 4-bedroom, 4.5-bath ranch-style home offers the rare combination of peaceful country living without feeling isolated from everyday conveniences. Thoughtfully designed for comfortable main-level living, the home blends manageable luxury, functionality, and scenic countryside beauty, creating an

  Ryan Rice Keller Williams Capital Properties

  1015 Redbud Rd, Winchester, VA 22603
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  $1,130,000

  New Construction $70K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,211 Sq Ft

  00 Light Rd, Winchester, VA 22603

  Your Dream Home in the Woods – To Be Built on 20 Unrestricted Acres! Create your own family compound, farm, hobbies, your choice. Imagine coming home to this stunning new construction nestled on twenty wooded and open acres with pleasant peaceful views. This thoughtfully designed home features spacious living areas, modern finishes, and a classic exterior that blends beautifully with its natural

  Melissa Johnston ERA Oakcrest Realty, Inc.

  00 Light Rd, Winchester, VA 22603
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  /52

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,799 Sq Ft

  437 Beechcroft Rd, Winchester, VA 22601

  BRICK BEAUTY ON A CORNER LOT WITH AN ATTACHED CARPORT AND A FULL BASEMENT. This remodeled and freshly painted 2-bedroom, 2-bath rancher with newly refinished hardwood floors is move-in ready. In-town convenience with nearby shopping, restaurants and services. A short drive to commuter routes 81, 37 and 50, downtown and Winchester Medical Center. Perfect for those who are downsizing or just

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  437 Beechcroft Rd, Winchester, VA 22601
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  /18

  $539,990

  New Construction

  • 3 Beds
  • 3 Baths
  • 2,050 Sq Ft

  108 Zinnia Ln, Winchester, VA 22603

  This stunning twin/semi‐detached home is ready for move in and located within the desirable 55+ gated community, Hiatt Pointe at Snowden Bridge. Designed for effortless main‐level living, the home features both a primary and secondary bedroom on the first floor—perfect for comfort and convenience.An open floor plan seamlessly connects the family room and kitchen, creating an inviting space

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  108 Zinnia Ln, Winchester, VA 22603
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  /48

  $639,900

  $10K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,419 Sq Ft

  151 Darby Dr, Winchester, VA 22602

  Lovely contemporary home in the established Ravenwing subdivision, featuring a highly desirable main-level primary suite and a layout you’ll instantly fall in love with. The well-designed floor plan offers spacious second-floor bedrooms, a finished basement complete with a kitchenette, and a screened rear porch overlooking a fenced yard. Enjoy peaceful views of the picturesque common area and

  Dave Spence RE/MAX Roots

  151 Darby Dr, Winchester, VA 22602
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  /12

  $632,990

  New Construction $36K PRICE DROP

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

  5 Williamson Rd, Winchester, VA 22602

  Welcome to Abrams Pointe, featuring new single-family homes in an established Winchester neighborhood, complete with wooded cul-de-sac homesites. The Drexel Floorplan is a spacious and versatile single-family home designed to suit a variety of lifestyles. With up to 3,213 finished square feet, the Drexel offers generous living space that can be customized to meet your needs. It features

  Dick Bryan New Home Star Virginia, LLC

  5 Williamson Rd, Winchester, VA 22602
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  /49

  $689,990

  • 5 Beds
  • 3.5 Baths
  • 4,035 Sq Ft

  220 Lehigh Dr, Winchester, VA 22602

  Luxury, Lifestyle & Nearly $100,000 in Premium Upgrades in Winchester's Desirable Senseny Village Welcome to 220 Lehigh Drive, an exceptional residence where modern construction meets thoughtful luxury upgrades and resort-style outdoor living. Built in 2023 and extensively enhanced by the current owner, this stunning 5-bedroom, 3.5-bath home offers the rare opportunity to enjoy the benefits of

  Susan Wathen EXP Realty, LLC

  220 Lehigh Dr, Winchester, VA 22602
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  /16

  $364,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,966 Sq Ft

  105 Bonnings Dr, Winchester, VA 22603

  Introducing the St. Paul, one of Maronda’s latest townhome designs.The St. Paul offers a range of 1,966 to 1,989 square feet of living space, including 3 to 4 bedrooms, 2.5 to 3.5 bathrooms, and a spacious 1-car garage. This new design offers plenty of personalization opportunities to fit your family’s unique needs.On the first floor of the home, you will find a spacious, open-concept floor plan.

  Maronda Homes Builder

  105 Bonnings Dr, Winchester, VA 22603
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  $399,500

  $50K PRICE DROP

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

  155 Royal Ave, Winchester, VA 22602

  Super location in Winchester, VA. This property is located just past Costco off of Rte. 522S. Situated on a quiet street this Cape Cod has a wonderful covered front porch with the addition of a rear closed in porch. The main and upstairs have hardwood flooring. The main floor consists of a bedroom, full bath, living room,dining room, and a large kitchen with plenty of room for a breakfast area.

  Jim Stafford ERA Oakcrest Realty, Inc.

  155 Royal Ave, Winchester, VA 22602
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  $1,150,000

  $100K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,880 Sq Ft

  199 Laurel Grove Rd, Winchester, VA 22602

  Nestled in the scenic countryside of Winchester, this impressive custom built home offers space, privacy, and beautiful Shenandoah Valley surroundings. Located in Frederick County, the property combines peaceful rural living with convenient access to shopping, dining, and commuter routes.Custom built in 2020, this spacious residence offers approximately 4,800+ square feet of living space on

  RoxAnn Grimes RE/MAX Roots

  199 Laurel Grove Rd, Winchester, VA 22602
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  $310,500

  • 3 Beds
  • 2 Baths
  • 1,474 Sq Ft

  406 Highland Ave, Winchester, VA 22601

  DIRECTIONS FOR PARKING; FROM NAT AVE TAKE RIGHT ON ATHEY ALLY TO 4 CAR PARKING AREA ON LEFT - LOOK FOR 406 MARKER. Located in The Historic Old Town Winchester area with private parking right off of Athey Alley, we are happy to list this nicely remodeled 2 story circa 1930s, center hall home.. Since the purchase of this home, the owners have totally resurfaced and painted the metal roof, installed

  Lisette Turner Century 21 Redwood Realty

  406 Highland Ave, Winchester, VA 22601
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  $320,000

  • 3 Beds
  • 3 Baths
  • 1,281 Sq Ft

  115 S Purcell Ave, Winchester, VA 22601

  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. Great investment opportunity! Currently tenant-occupied, offering

  Matthew Berry MarketPlace REALTY

  115 S Purcell Ave, Winchester, VA 22601
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  /41

  $395,900

  $13K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,615 Sq Ft

  114 Woodys Place, Winchester, VA 22602

  TOTALLY Renovated & Everything SHINES!! If this home had a Brand, it would be NEW!! The 3Br. 2 Ba. home features an excellent floorplan, providing an open & airy feel with skylights & cathedral ceilings that run the span of both levels. The main level features a master suite w/ private full bath, & walk in closet, the kitchen gleams with Top end appliances, gorgeous Granite countertops & abundant

  Dave Lyne Motion Realty, LLC

  114 Woodys Place, Winchester, VA 22602
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  /34

  $799,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,139 Sq Ft

  169 Cather Ln, Winchester, VA 22602

  Estimated completion August 2026. Photos shown are of a similar home previously constructed by the builder. Finishes and features may vary. Welcome to 169 Cather Lane, a spacious rancher situated on 5 beautiful pastoral acres with stunning views and an unbeatable location just minutes from town. Built by local builder Scott & Scott Construction, this home offers the perfect blend of quality

  Kaitlyn Behr Samson Properties

  169 Cather Ln, Winchester, VA 22602
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  /24

  $519,990

  New Construction

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

  TBD Munsee Cir, Winchester, VA 22602

  The Pine offers 1,964 square feet of modern living space - perfect for growing families or those who love to entertain. This well-designed single family home includes four spacious bedrooms, two and a half bathrooms, and a two-car garage on slab foundation. The open-concept design showcases a contemporary kitchen with stainless steel appliances, quartz countertops, and white cabinetry - combining

  D.R. Horton Builder

  TBD Munsee Cir, Winchester, VA 22602
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  /36

  $385,000

  $14K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,601 Sq Ft

  13 E Leicester St, Winchester, VA 22601

  Incredible location, incredible home! Relax on the elevated front porch overlooking Leicester St, or retreat to the private back yard. Inside, gleaming wood floors and original trim compliment the new kitchen and bathrooms. HVAC, wiring, plumbing, windows, roofing, and siding have been lovingly replaced/updated in the last 5 years. This home is walkable to everything, and sits on a calm side

  William Steinmetz RE/MAX Roots

  13 E Leicester St, Winchester, VA 22601
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  /15

  $391,990

  New Construction

  • 3 Beds
  • 1.5 Baths
  • 1,752 Sq Ft

  105 Heirloom Way, Winchester, VA 22603

  This stunning two-level villa boasts a modern open concept design that seamlessly connects living spaces for an inviting and spacious feel. The main level features a living room that opens effortlessly to the dining area, creating a perfect space for entertaining and family gatherings. The expansive rear kitchen includes an L-shaped layout with an eating bar and an island with additional bar

  Brookfield Residential Builder

  105 Heirloom Way, Winchester, VA 22603
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  /96

  $489,900

  • 5 Beds
  • 3 Baths
  • 1,887 Sq Ft

  419 Summit Ave, Winchester, VA 22601

  Welcome Home! This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment. With 5 spacious

  Waqas Abbasi Lifestyle Realty, LLC.

  419 Summit Ave, Winchester, VA 22601
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  /8

  $399,999

  Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,808 Sq Ft

  217 Pembridge Dr, Winchester, VA 22602

  COMING SOON! Welcome to this well-maintained home in the sought-after Pembridge Heights community on the east side of Winchester. Conveniently located with easy access to Route 50, I-81, shopping, dining, and commuter routes, this property offers a blend of comfort, functionality, and numerous recent updates. The kitchen features granite countertops and updated appliances, including a

  Sue Goodwin Long & Foster Real Estate, Inc.

  217 Pembridge Dr, Winchester, VA 22602
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  /48

  $549,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,279 Sq Ft

  104 Wagtail Ln, Winchester, VA 22603

  *****LENDER CREDIT WITH AN OFFER AND USE OF LENDER!!!*****Welcome to the Vale at Hiatt Pointe—THIS IS ONE OF A KIND WITH THIS VIEW! a brand-new 2025 end-unit villa that is ready for immediate move-in. This beautifully upgraded two-car front-load garage home features three bedrooms, two full baths, and one half bath, offering the perfect blend of style, comfort, and convenience.Enjoy peace

  Kathrin Donovan Keller Williams Realty

  104 Wagtail Ln, Winchester, VA 22603
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  /18

  $324,900

  New Construction $5K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,152 Sq Ft

  212 Falcon Trail, Winchester, VA 22602

  Mearing completion! Current Shawneeland Inventory107 Pinto Trail (split foyer)208 Beaver Trail (split foyer)210 Beaver Trail (split foyer)212 Falcon Trail (colonial)211 Inca Trail (colonial)103 Tonto Trail (split foyer)123 Killbuck Trail (colonial)1/3 Acre – No Carpet!This affordable 2-bed, 2.5-bath home offers high-end finishes and incredible growth

  Jim Thomson Realty ONE Group Old Towne

  212 Falcon Trail, Winchester, VA 22602
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  /83

  $2,200,000

  • 5 Beds
  • 4.5 Baths
  • 5,884 Sq Ft

  2230 Jones Rd, Winchester, VA 22602

  Set on 21.5 acres just minutes from downtown Winchester, this 5-bedroom home offers over 5,800 finished square feet with a blend of space, functionality, and outdoor living in a highly convenient location. Combining usable land, thoughtful improvements, and indoor and outdoor entertaining spaces, this property offers a rare opportunity close to town amenities. The main living areas feature an

  Jennifer Sacco RE/MAX Roots

  2230 Jones Rd, Winchester, VA 22602
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  /28

  $400,000

  $29K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,432 Sq Ft

  115 E Monmouth St, Winchester, VA 22601

  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!

  Mafe Zambrano Inmobiliaria De Las Casas LLC

  115 E Monmouth St, Winchester, VA 22601
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  /33

  $424,900

  Open Sat 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  1025 S Loudoun St, Winchester, VA 22601

  **Motivated sellers!! Now offering to pay buyers closing costs!!** 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

  Michael Sprague Samson Properties

  1025 S Loudoun St, Winchester, VA 22601
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  /59

  $699,900

  • 3 Beds
  • 3 Baths
  • 3,280 Sq Ft

  407 Mikey Ct, Winchester, VA 22601

  One owner meticulously cared for home located in this 55+ sought after community, The Village at Harvest Ridge. Address is Winchester 22601 but its taxed in Frederick Co., Va. one block from city limits convenient for shopping, dining out and near medical services. Step inside to find hardwood floors that flow through the main level to a open floor plan dining/living room with gas log fireplace.

  George Johnson Jim Barb Realty Inc.

  407 Mikey Ct, Winchester, VA 22601
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  /2

  $449,900

  Coming Soon

  • 4 Beds
  • 3 Baths
  • 1,764 Sq Ft

  100 Huntcrest Cir, Winchester, VA 22602

  It’s almost time. Stay tuned — professional photos and full details to follow

  LESLIE WEBB Long & Foster Real Estate, Inc.

  100 Huntcrest Cir, Winchester, VA 22602
• 

  

  /23

  $649,990

  New Construction $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,412 Sq Ft

  116 Sunflower Way, Winchester, VA 22603

  New, main level living home is under construction and will be ready this spring!! This Rockwell with 10 year builder warranty is located on a corner homesite, backing to open space, in Hiatt Pointe at Snowden Bridge, an active adult community for those 55 or better!The stunning kitchen showcases Gourmet Stainless Steel Appliances with hood, white cabinets, quartz countertops, and an oversized

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  116 Sunflower Way, Winchester, VA 22603

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