Winchester, VA Homes for Sale

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  $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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  /32

  $329,900

  • 3 Beds
  • 2.5 Baths
  • 1,488 Sq Ft

  103 Trade Wind Ln, Winchester, VA 22602

  Welcome home to 103 Trade Wind Lane, a beautifully updated townhome offering low-maintenance living on Winchester’s desirable east side! Perfectly situated near top schools, shopping, dining, and major commuter routes, this turn-key residence delivers both comfort and ultimate convenience. Natural light pours into the bright living room, where modern flooring lead you straight into the open

  Dan Whitacre Colony Realty

  103 Trade Wind Ln, Winchester, VA 22602
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  /33

  $599,990

  New Construction $51K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,865 Sq Ft

  239 Hydrangea Way, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Clifton floorplan is a thoughtfully designed 1,865 sq. ft. ranch home, blending style and functionality in a single-level open layout. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The kitchen opens to a large great room with two windows that let in

  D.R. Horton Builder

  239 Hydrangea Way, Winchester, VA 22602
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  /17

  $449,990

  New Construction $3K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,657 Sq Ft

  136 Wappinger Terrace, Winchester, VA 22602

  Step into 1,657 square feet of well-designed living space in the Cabral, featuring 3 spacious bedrooms, 2.5 bathrooms, and a flexible loft upstairs—perfect for a home office, playroom, or additional lounge area. This home showcases a charming white siding exterior with stone accents, while the interior boasts sleek white kitchen and bathroom cabinets paired with modern finishes throughout. Enjoy

  D.R. Horton Builder

  136 Wappinger Terrace, Winchester, VA 22602
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  /60

  $935,000

  $10K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,278 Sq Ft

  218 Babbs Mountain Rd, Winchester, VA 22603

  A PRIVATE CUSTOM-BUILT ESTATE SURROUNDED BY NATURE — WITH YOUR OWN RESORT-STYLE POOL! Set on an extraordinary 6.44 private acres, this exquisite custom-built residence offers nearly 4,700 square feet of beautifully finished living space across three levels, combining luxurious indoor living with an incredible outdoor setting. Tucked away among the trees, this is the kind of property where you can

  John Ginty Samson Properties

  218 Babbs Mountain Rd, Winchester, VA 22603
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  /51

  $579,990

  $19K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,442 Sq Ft

  139 Poe Dr, Winchester, VA 22602

  Welcome to this nearly new 4-bedroom, 3-bath home in the sought-after Raven Oaks community, offering a convenient Winchester location, modern finishes, flexible living space, and desirable community amenities. Ideally situated with easy access to Route 50 and I-81, the home is just minutes from Shenandoah University, Jim Barnett Park, shopping, restaurants, and everyday conveniences. Historic Old

  Sheila Pack RE/MAX Roots

  139 Poe Dr, Winchester, VA 22602
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  /65

  $559,000

  $41K PRICE DROP

  • Studio
  • 3,511 Sq Ft

  1400 Valley Ave, Winchester, VA 22601

  Versatile on Valley!So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful wood floors, tall ceilings, fireplace, sunroom, and a stunning staircase that adds timeless character. Each Unit has 3 bedrooms and 1.5 baths. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income

  Danielle Spriggs Samson Properties

  1400 Valley Ave, Winchester, VA 22601
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  /51

  $224,900

  $34K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  8 Brookland Ct Unit 8, Winchester, VA 22602

  2 Bed, 2 bath condominium. New appliances, including water heater and heat pump. Gas fireplace, open concept with separate dining room. Patio/ porch with french doors and skylights in living room allow tons of natural light. Primary suite includes walk-in closet. Conveniently located off rt 7 and 81.

  Vicki Broy RE/MAX Roots

  8 Brookland Ct Unit 8, Winchester, VA 22602
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  /52

  $369,990

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  229 Monteith Dr, Winchester, VA 22601

  The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room. ***OFFERING UP TO $5K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED

  Brittany Newman DRB Group Realty, LLC

  229 Monteith Dr, Winchester, VA 22601
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  /19

  $141,500

  • Land
  • 11.1 Acres
  • $12,748 per Acre

  0 Hodges Lot 14 Ln, Winchester, VA 22603

  Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Hodges Lot 14 Ln, Winchester, VA 22603
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  /32

  $629,000

  Open Sun 12PM - 2PM $21K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,967 Sq Ft

  115 Marion Dr, Winchester, VA 22603

  Seller is offering a $2,500 credit toward the purchaser's closing costs, mortgage rate buy-down, prepaid expenses, moving costs, or other allowable buyer expenses. Situated on approximately 2.57 acres in Frederick County, this beautifully maintained 4-bedroom, 2.5-bath Traditional home offers nearly 3,000 square feet of thoughtfully designed living space. Built in 2020, the home features a

  Abby Walters Preslee Real Estate

  115 Marion Dr, Winchester, VA 22603
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  /23

  $127,750

  • Land
  • 8.11 Acres
  • $15,752 per Acre

  0 Wolf Spring Trail Unit VAFV2043748, Winchester, VA 22602

  Rare opportunity to own three adjoining fully wooded parcels in the quiet and peaceful Shawneeland community. Numerous residential and recreational possibilities exist with ownership of these tracts. Located just a few miles west of Winchester in the Rosenberger area of the county. Access is secured via extensive road frontage on paved Wolf Spring Trail. Utilities are close by making for easy and

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Wolf Spring Trail Unit VAFV2043748, Winchester, VA 22602
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  /2

  $175,000

  $25K PRICE DROP

  • 1 Bed
  • 1 Bath

  5737 N Frederick Pike, Winchester, VA 22603

  4.2 Acres, Sold As-Is, Flat Usable Lot, Partially Wooded, Well and Septic Exists, Just Outside of Winchester VA, No HOA, Unrestricted. Well and septic on property . Well is located in back of old mobile home at water pump. Septic located further back behind old mobile home marked wirh red sparay paint. Health department docs are in bright. Neither house nor mobile home livable.Sold As Is With

  Tracy Link Coldwell Banker Premier

  5737 N Frederick Pike, Winchester, VA 22603
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  /52

  $569,000

  • 4 Beds
  • 4 Baths
  • 2,489 Sq Ft

  687 Woodland Ave, Winchester, VA 22601

  ONE-OF-A-KIND HOME WITH INCREDIBLE FLEXIBILITY! This custom all-brick Winchester home offers a layout you simply don't find every day—4 bedrooms, 4 full baths, two main-level bedrooms, flexible private living spaces, a detached 2-car garage and NO HOA!Step inside to a bright, welcoming floor plan featuring beautiful hardwood floors, abundant natural light, custom built-ins and a cozy gas

  Katy Donovan Keller Williams Realty

  687 Woodland Ave, Winchester, VA 22601
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  /67

  $740,000

  New Construction $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,129 Sq Ft

  230 Tranquil Wood Ln, Winchester, VA 22602

  Tucked away on over 3 private acres in the scenic countryside of Frederick County, this newly completed modern farmhouse offers peaceful country living with the convenience of nearby Winchester amenities and major commuter routes. Custom built by Water Creek Homes, the home showcases quality craftsmanship, elevated finishes, and carefully curated details throughout. Designed to stand apart from

  Monique Rodriguez Pearson Smith Realty LLC

  230 Tranquil Wood Ln, Winchester, VA 22602
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  /39

  $290,000

  $25K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,170 Sq Ft

  126 Marple Rd, Winchester, VA 22603

  Charming Cape Cod-style home located at 126 Marple Rd in the desirable north end of Winchester! This well-maintained 3-bedroom, 1.5-bath home offers timeless character, functional living space, and a convenient commuter-friendly location. The main level features a bedroom with a 1/2 bath, a living room, a dining room, and a kitchen. Upstairs, you’ll find additional bedrooms with a shared

  RoxAnn Grimes RE/MAX Roots

  126 Marple Rd, Winchester, VA 22603
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  /33

  $348,000

  $12K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  302 Wentworth Dr, Winchester, VA 22601

  Enjoy one-level living in this spectacularly located brick rambler, nestled in a quiet residential neighborhood while remaining conveniently close to Route 11 with easy access to I-81. The property currently has a long term month-to-month tenant paying under market value, offering flexibility for an owner-occupant or an investor seeking rental income with potential for increased rent. Situated on

  Heloisa Amar Samson Properties

  302 Wentworth Dr, Winchester, VA 22601
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  /35

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft

  112 W Germain St, Winchester, VA 22601

  100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025!This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic

  Amanda Magana RE/MAX Roots

  112 W Germain St, Winchester, VA 22601
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  /40

  $555,900

  $31K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,460 Sq Ft

  104 Murphy Ct, Winchester, VA 22602

  Gorgeous 4-Bedroom Colonial in Sought-After Sovereign Village! This beautifully maintained home is nestled on a large cul-de-sac, offering privacy, space, and comfort both inside and out. This home boasts a well-designed layout perfect for everyday living and entertaining. The bright, open main level with shining hardwood floors creates a warm and inviting atmosphere. Cozy up by the gas fireplace

  Jennifer Hoyer Epic Realty, LLC.

  104 Murphy Ct, Winchester, VA 22602
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  /81

  $969,000

  • 5 Beds
  • 3.5 Baths
  • 3,932 Sq Ft

  485 Lake Serene Dr, Winchester, VA 22603

  A rare opportunity to live on Lake Serene - Welcome to your private lakefront retreat on Lake Serene, where lake-life meets timeless craftsmanship. 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

  Angela Duncan MarketPlace REALTY

  485 Lake Serene Dr, Winchester, VA 22603
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  /58

  $749,900

  $50K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,952 Sq Ft

  2122 Jones Rd, Winchester, VA 22602

  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

  Jennifer Sacco RE/MAX Roots

  2122 Jones Rd, Winchester, VA 22602
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  /32

  $399,900

  $29K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,419 Sq Ft

  118 1/2 E Cork St, Winchester, VA 22601

  Seeking the perfect blend of historic character and modern urban living? This exceptional Urban Lofts Condominium is just one and a half blocks from Old Town Winchester Walking Mall, offering easy access to restaurants, boutiques, entertainment, and vibrant downtown living. Originally built in the early 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural

  Janet Flaherty Keller Williams Realty

  118 1/2 E Cork St, Winchester, VA 22601
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  /25

  $419,900

  $10K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,800 Sq Ft

  112 Hites St, Winchester, VA 22602

  This beautiful home features two primary suites, one on each level, offering flexibility and convenience. The upper-level primary suite includes a versatile flex space, perfect for a home office, nursery, or sitting area. Freshly painted and featuring wood floors throughout, the home is move-in ready.Additional highlights include an attached one-car garage and a desirable location in

  Rolando Sabogal First Decision Realty LLC

  112 Hites St, Winchester, VA 22602
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  /26

  $374,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  HomeSite 5 Shuoner Ct, Winchester, VA 22602

  MOVE IN READYSt. Paul Townhome TBB | 3 BR | 2.5 BA | 1-Car Garage | Finished Lower LevelBeautiful wooded homesites available!Offering up to 2,000 sq. ft. of modern, open-concept living designed for today's lifestyle.Home HighlightsOpen-concept main level — perfect for entertaining family and friendsGranite countertopsStainless steel

  Jimmy Thomas New Home Star Virginia, LLC

  HomeSite 5 Shuoner Ct, Winchester, VA 22602
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  /5

  $10,000

  • Land
  • 0 Sq Ft

  Lot 13 Tomahawk Trai 0, Winchester, VA 22602

  Welcome to Shawneeland! This mountain community is tucked away in a rural setting and a short distance to shopping, restaurants and Winchester's Historic Downtown. Utilize this 0.48 acre lot as a potential building lot, recreational space or enjoy the amenities such as Lake Cherokee with a beach area, fishing and picnic areas. Purchaser to verify location of boundary lines.

  Kim Hurst MarketPlace REALTY

  Lot 13 Tomahawk Trai 0, Winchester, VA 22602
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  /70

  $400,000

  $10K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 1,568 Sq Ft

  112 Ashley Dr, Winchester, VA 22602

  REDUCED PRIICE FOR A QUICK SALE !! HURRY UP!! READY TO MOVE ! This well-maintained residence combines comfort, functionality, and convenience. The main level features an inviting open-concept layout filled with natural light—perfect for everyday living and entertaining. The spacious kitchen offers ample counter space, abundant cabinetry, and direct access to the rear deck, making indoor-outdoor

  Martha Sanchez Spring Hill Real Estate, LLC.

  112 Ashley Dr, Winchester, VA 22602
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  /13

  $598,990

  New Construction $76K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,875 Sq Ft

  TO BE BUILT-HOMESITE Duke Ct, 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 Duke Ct, Winchester, VA 22602
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  /2

  $4,500

  $1K PRICE INCREASE

  • Land
  • 10,890 Sq Ft
  • $18,000 per Acre

  107 Fox Trail, Winchester, VA 22602

  Lot 109 is also available for sale but not listed.

  Babak Taghavi Venture Realty

  107 Fox Trail, Winchester, VA 22602
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  /8

  $760,000

  New Construction $15K PRICE INCREASE

  • 3 Beds
  • 3.5 Baths
  • 2,550 Sq Ft

  0 Tumble Leaf Ln, Winchester, VA 22602

  CARRINGTON HOMES AT FALL RIDGE ESTATES- 5 Acre Wooded LOTS WITH MOUNTAIN VIEWS. Choose from 7 different floorplans including our Dogwood model ( One Story Living ) with standard 10' main level ceilings and 13' ceilings in the Family Room.Model Home Open on Weekends from 11-5 at 156 Covey Lane Winchester Va

  Daniel Boris Pearson Smith Realty, LLC

  0 Tumble Leaf Ln, Winchester, VA 22602
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  /3

  $754,725

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,380 Sq Ft

  120 Malbec Ct, Winchester, VA 22602

  The Somerset home design by Maronda Homes is designed with today’s lifestyle in mind—blending open-concept living, functional spaces, and refined details into one beautifully crafted home. With 4 bedrooms, 2 to 4 bathrooms, and 3,194 square feet of living space, the Somerset offers flexibility for families at every stage of life.The heart of the home is the expansive great room, which opens to a

  Maronda Homes Builder

  120 Malbec Ct, Winchester, VA 22602
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  /9

  $379,990

  New Construction

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

  109 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

  109 Heirloom Way, Winchester, VA 22603
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  /19

  $381,690

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  652 Arden Ct, Winchester, VA 22601

  652 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for September move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances.

  D.R. Horton Builder

  652 Arden Ct, Winchester, VA 22601
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  /39

  $498,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,023 Sq Ft

  39 Rossmann Blvd, Winchester, VA 22602

  To be built-choose your colors and upgrades! Photos are similar and include upgrades. Beautifully crafted new home by a respected local builder, offering over 2,000 square feet of thoughtfully designed living space in the desirable Sovereign Village community. The inviting, open-concept main level features a spacious kitchen with a large island, perfect for gathering and entertaining, that

  Marisa Varley ERA Oakcrest Realty, Inc.

  39 Rossmann Blvd, Winchester, VA 22602
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  /14

  $389,990

  New Construction

  • 3 Beds
  • 4 Baths
  • 1,905 Sq Ft

  116 Swansong Place, Winchester, VA 22603

  The three-level Skyline model masterfully combines a traditional exterior with a contemporary, open-concept floor plan. On the main level, you’ll find an expansive living room, bathed in natural light from numerous windows, flows effortlessly into the dining area and kitchen. The kitchen is designed with an L-shaped countertop and an island that borders the dining room. A cozy nook serves as a

  Brookfield Residential Builder

  116 Swansong Place, Winchester, VA 22603
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  /36

  $646,045

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft

  228 Hydrangea Way, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Azalea floorplan is a thoughtfully designed 1,888 sq. ft. ranch home blending style and functionality in a single-level open layout. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen,

  D.R. Horton Builder

  228 Hydrangea Way, Winchester, VA 22602
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  /23

  $349,990

  New Construction

  • 3 Beds
  • 1.5 Baths
  • 1,893 Sq Ft

  117 Castaway Place, 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

  117 Castaway Place, Winchester, VA 22603
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  /24

  $25,000

  • Land
  • 1.43 Acres
  • $17,483 per Acre

  LOT 5A Fox Trail, Winchester, VA 22602

  Beautiful building lot located in Mountain Falls Park – Wilde Acres. This is the last lot on the right on Fox Trail, offering excellent privacy and seclusion. The property backs to permanent open space, providing a peaceful setting with mountain views and abundant wildlife. Approved for a 3-bedroom septic system with a certification letter on file. A current survey is also available. This is an

  Nadeem Helfer Samson Properties

  LOT 5A Fox Trail, Winchester, VA 22602
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  /69

  $639,900

  $10K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,179 Sq Ft

  1529 Dalton Place, Winchester, VA 22601

  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

  RoxAnn Grimes RE/MAX Roots

  1529 Dalton Place, Winchester, VA 22601
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  /106

  $849,000

  • 6 Beds
  • 4.5 Baths
  • 4,714 Sq Ft

  226 Summerfield Dr, Winchester, VA 22602

  UP TO $5000 SELLER CONCESSION FOR PAINT. CALL FOR DETAILS. Welcome to this stunning Colonial estate nestled in the highly sought-after Raven Pointe neighborhood of Winchester, VA. This exceptional home flawlessly pairs a grand interior layout with panoramic views, perfectly situated directly adjacent to peaceful farmland while remaining just 7 minutes away from historic Old Town Winchester. Built

  Jeffrey Stack CENTURY 21 New Millennium

  226 Summerfield Dr, Winchester, VA 22602
• 

  

  /15

  $435,000

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

  122 Cherry Hill Cir, Winchester, VA 22602

  Nestled in the charming Green Acres subdivision, this delightful split-level home offers a perfect blend of comfort and functionality. With five spacious bedrooms and four full bathrooms, there's ample room for everyone to unwind and thrive. The heart of the home features a cozy fireplace, inviting you to gather with loved ones during chilly evenings. The fully finished basement, complete with

  Jen Moore ERA Oakcrest Realty, Inc.

  122 Cherry Hill Cir, Winchester, VA 22602

Showing Results 201 - 240, Page 6 of 13