Winchester, VA Homes for Sale with Pool

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  /64

  $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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  /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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  /27

  $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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  /58

  $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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  /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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  /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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  /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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  /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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  /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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  /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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  /38

  $548,990

  New Construction

  • 2 Beds
  • 2 Baths
  • 1,748 Sq Ft

  BRISTOL Plan at Willow Run, Winchester, VA 22601

  We're excited to introduce the Bristol, our stunning new ranch design! This floorplan starts at 1,748 square feet and features 3 bedrooms, 2 bathrooms, and a 2-car garage.Step into a welcoming foyer that guides you past two cozy secondary bedrooms and into the main living area, where the family room, charming dining nook, and beautifully designed kitchen come together. The kitchen boasts

  D.R. Horton Builder

  105 Trellis View Ln Unit 36406038, Winchester, VA 22601
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  /27

  $429,990

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,168 Sq Ft

  FREEPORT DUPLEX Plan at Willow Run - Duplexes, Winchester, VA 22601

  Looking for a beautiful home that meets all your needs? Look no further than the Freeport! This stunning 1,492 square foot residence features three bedrooms, two baths, and a convenient two-car garage, all designed with your active adult lifestyle in mind.As you step into the foyer, you are greeted by the open-concept kitchen and living area with plenty of space for cooking, dining, and

  D.R. Horton Builder

  105 Trellis View Ln Unit 36406838, Winchester, VA 22601
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  /81

  $345,000

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,824 Sq Ft

  120 Scirocco Ln, Winchester, VA 22602

  This beautifully maintained 3-bedroom, 1.5-bath townhome offers three finished levels of living space with even more potential in the basement to create an additional bedroom, office, or recreation room.Step inside to find numerous recent updates, including new LVP flooring, fresh paint, updated lighting, new carpet upstairs, updated interior door hardware, a new washer and dryer, and a

  Nicole Mongold Mountains Edge Realty LLC

  120 Scirocco Ln, Winchester, VA 22602
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  /2

  $541,990

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,958 Sq Ft

  DOVER Plan at Willow Run, Winchester, VA 22601

  The Dover by D.R. Horton is a stunning new construction, ranch home plan featuring 1,958 square feet of living space, 3 bedrooms, 2 bathrooms and a 2-car garage.The foyer welcomes you in with two versatile bedrooms, sharing a well-appointed full bathroom. As you continue down the foyer, you’ll find a spacious office, coat closet, and laundry room. At the heart of the home is the kitchen,

  D.R. Horton Builder

  105 Trellis View Ln Unit 36406788, Winchester, VA 22601
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  /17

  $424,990

  New Construction $10K PRICE INCREASE

  • 3 Beds
  • 3.5 Baths
  • 2,094 Sq Ft

  110 Coriander Dr, Winchester, VA 22603

  BUILDER OFFERING BELOW MARKET RATE FINANCING OPTIONS ON THIS QUICK MOVE IN HOME!!Brand-New Dual Primary Townhome—Late Summer Move-In!Step into modern living with this beautifully designed dual primary bedroom home, ideally located just steps from Snowden Bridge’s newest amenities. The entry-level bedroom with a full bath offers flexible space for guests, multigenerational living, or a

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  110 Coriander Dr, Winchester, VA 22603
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  /40

  $439,900

  • 3 Beds
  • 2 Baths
  • 1,307 Sq Ft

  153 Fox Dr, Winchester, VA 22601

  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

  Amber Jenkins Century 21 Redwood Realty

  153 Fox Dr, Winchester, VA 22601
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  /70

  $3,500,000

  • 3 Beds
  • 3.5 Baths
  • 4,421 Sq Ft

  450 Green Spring Rd, Winchester, VA 22603

  Be sure to see the video and 3D tour to fully explore this property! **Briede Family Vineyards** presents an exceptional opportunity to acquire one of Virginia's distinguished boutique vineyard estates. Offering far more than beautiful real estate, it provides the new owners the opportunity to continue a well-established legacy within the Commonwealth's thriving wine industry. Combining

  Rick Guthrie Keller Williams Realty

  450 Green Spring Rd, Winchester, VA 22603
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  /44

  $402,160

  New Construction

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

  169 Sequoia Dr, Winchester, VA 22602

  Move into your new home this October and enjoy the best of fall in this stunning Adams end-unit townhome! Featuring a classic white siding exterior and bright, timeless white cabinetry, this home offers 4 bedrooms, 3.5 baths, a 1-car garage, and 1,889 square feet of thoughtfully designed living space across three levels. The main level showcases 9-foot ceilings, luxury vinyl plank flooring,

  Victoria Clark D R Horton Realty of Virginia LLC

  169 Sequoia Dr, Winchester, VA 22602
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  /59

  $667,000

  $18K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,399 Sq Ft

  108 Nevermore Dr, Winchester, VA 22602

  ATTENTION:Best price per sq ft in the development . Practicality meets long-term value with a $70,000 IN UPGRADES to install a 32 PANEL SOLAR SYSTEM., that that virtually reduces monthly electric bills. An additional $30,000 was invested into a COMPOSITE DECK AND FENCE.Welcome to 108 Nevermore Drive, nestled in the sought-after Raven Oaks community of Winchester, where comfort, energy

  Mike Dotterweich RE/MAX Gateway, LLC

  108 Nevermore Dr, Winchester, VA 22602
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  /74

  $624,900

  $40K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,904 Sq Ft

  104 Bramble Ct, Winchester, VA 22602

  Welcome to this beautifully maintained 3-level Colonial tucked away on a quiet cul-de-sac in sought-after Oakdale Crossing. With 4 bedrooms, 2.5 baths, a remodeled kitchen, spacious living areas, and room to make the home your own, this is the kind of place that checks the boxes for today—and gives you plenty of space for whatever comes next.The main level is made for living, hosting, and

  Laura White ERA Oakcrest Realty, Inc.

  104 Bramble Ct, Winchester, VA 22602
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  /90

  $649,900

  $25K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 4,030 Sq Ft

  146 Stonebrook Rd, Winchester, VA 22602

  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

  Bradley Comstock ERA Oakcrest Realty, Inc.

  146 Stonebrook Rd, Winchester, VA 22602
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  /41

  $568,990

  New Construction

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

  AZALEA Plan at Willow Run, Winchester, VA 22601

  Discover the charm of the Azalea at Willow Run, a thoughtfully designed 1,888 square foot ranch home that embodies comfort and accessibility. With three spacious bedrooms and two modern bathrooms, this single-story layout caters to those who appreciate both style and functionality.Step inside to find an inviting foyer that leads to a seamless open floor plan, merging the dining room,

  D.R. Horton Builder

  105 Trellis View Ln Unit 36405635, Winchester, VA 22601
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  /63

  $749,050

  $26K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,757 Sq Ft

  107 Cahille Dr, Winchester, VA 22602

  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

  Laura White ERA Oakcrest Realty, Inc.

  107 Cahille Dr, Winchester, VA 22602
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  /82

  $1,239,000

  • 4 Beds
  • 7.5 Baths
  • 5,662 Sq Ft

  1022 Heth Place, Winchester, VA 22601

  This amazing property is ready for you! Located close to Winchester Medical Center, Churches, Shopping, Historic Downtown Winchester, John Kerr Elementary School, and John Handley High School. This property is beautifully landscaped with plush gardens, a koi pond, waterfalls, a large pool, pool room, large deck overlooking the property, and a fenced backyard lined with mature trees for privacy.

  Cynthia Butler Samson Properties

  1022 Heth Place, Winchester, VA 22601
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  /25

  $559,990

  New Construction $16K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 2,511 Sq Ft

  133 Wappinger Terrace, Winchester, VA 22602

  The Hayden is a spacious two-story home offering 6 bedrooms, 4 bathrooms, and over 3,100 square feet of thoughtfully designed living space, perfect for both everyday living and entertaining. The main level features a versatile flex room off the foyer, ideal for a formal dining room, home office, or additional living space. The gourmet kitchen includes an oversized island with seating, a large

  D.R. Horton Builder

  133 Wappinger Terrace, Winchester, VA 22602
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  /31

  $608,745

  New Construction

  • 2 Beds
  • 2 Baths
  • 1,748 Sq Ft

  227 Hydrangea Way, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Bristol floorplan is a thoughtfully designed 1,748 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

  227 Hydrangea Way, Winchester, VA 22602
• 

  

  /46

  $372,990

  New Construction

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

  ADAMS Plan at Retreat at Winding Creek - Townhomes, Winchester, VA 22602

  The 1,889 sq. ft. Adams townhome design comes complete with 4 bedrooms, 3.5 bathrooms, and a 1-car garage. You will love the granite counter tops, stainless steel appliances, and recessed lighting in the kitchen. Create the rec room, home office or 4th bedroom of your dreams in the lower level bonus space! The Adams comes with a 12'x10' deck off the rear of the home, perfect for outdoor

  D.R. Horton Builder

  137 Seminole Dr Unit 36203787, Winchester, VA 22602
• 

  

  /22

  $574,990

  New Construction

  • 3 - 5 Beds
  • 2 - 4 Baths
  • 2,137+ Sq Ft

  Rembrandt Plan at Hiatt Pointe at Snowden Bridge - 55+ Single Family Homes Collection, Winchester, VA 22603

  The Rembrandt is thoughtfully designed to offer a seamless balance of private and communal spaces, all while prioritizing main-level living. A covered entryway gracefully welcomes you home, leading to a central gathering area encompassing the family room, kitchen, and dining area. The kitchen is a culinary enthusiast's haven, featuring a substantial center island, ample cabinetry, and a

  Brookfield Residential Builder

  105 Wagtail Ln Unit 36578844, Winchester, VA 22603
• 

  

  /27

  $609,990

  New Construction

  • 4 Beds
  • 3 Baths
  • 3,000 Sq Ft

  601 Granite Ridge Dr, Winchester, VA 22603

  Brand New Main Level home is under construction and with special financing and closing cost assistance available, there is no reason to wait to make this the next place you call home! Located within Hiatt Pointe at Snowden Bridge, an active adult community for those 55 or better!This Rembrandt, located on a corner lot, a stunning home offering a harmonious blend of private sanctuaries and

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  601 Granite Ridge Dr, Winchester, VA 22603
• 

  

  /23

  $424,990

  New Construction $5K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 2,094 Sq Ft

  126 Swansong Place, Winchester, VA 22603

  BUILDER OFFERING BELOW MARKET RATE FINANCING ON THIS MOVE IN READY HOME!!Exceptional value for a 4‑bedroom END‑UNIT townhome is ready for move‑in! Brand‑new construction offers modern style and comfort with oak stairs with upgraded railings and durable LVP flooring throughout the main level. Backing to open space in the newest section of Snowden Bridge, this spacious home includes a flexible

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  126 Swansong Place, Winchester, VA 22603
• 

  

  /50

  $849,900

  New Construction

  • 5 Beds
  • 3 Baths
  • 3,057 Sq Ft

  Lot 10 Desant Cir, 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; 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 a

  Jim Thomson Realty ONE Group Old Towne

  Lot 10 Desant Cir, Winchester, VA 22603
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  /83

  $825,000

  $64K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,800 Sq Ft

  107 Launchris Dr, Winchester, VA 22602

  Looking for a home that gives you space, style, privacy, and the freedom to make it your own? Welcome to this stately Colonial set on nearly an acre of beautiful, private land—where timeless architecture meets the upgrades today's buyers want.The seller has invested more than $150,000 in improvements, including a fully renovated HVAC system with all-new ductwork and high-end components.

  Laura White ERA Oakcrest Realty, Inc.

  107 Launchris Dr, Winchester, VA 22602

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