Newest Homes for Sale in Winchester, VA

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  /22

  $235,000

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

  157 Brookland Terrace Unit 11, Winchester, VA 22602

  Top-Floor Gem with Vaulted Ceilings, Modern Upgrades & Quick Seller Move-Out!Welcome home to this bright and airy 2-bedroom, 2-bath top-level condo that perfectly blends comfort, style, and convenience — and offers buyers the advantage of quick seller vacancy for a smooth and flexible closing! Step inside and be greeted by soaring vaulted ceilings and abundant natural light streaming through

  Becky Green Samson Properties

  157 Brookland Terrace Unit 11, Winchester, VA 22602
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  /62

  $850,000 Coming Soon

  • 4 Beds
  • 4 Baths
  • 4,417 Sq Ft

  1006 Armistead St, Winchester, VA 22601

  Grand Elegance with Endless Potential – Spacious 3-Sided Brick Colonial with Soaring Ceilings and Room to Grow! Set on an elevated lot with commanding curb appeal, this stately all-brick-front Colonial welcomes you with timeless architecture and a wide front and back lawn. This spacious 4-bedroom, 2.5-bath home is full of opportunity for buyers ready to make it their own. Priced below tax value,

  Chris Craddock EXP Realty, LLC

  1006 Armistead St, Winchester, VA 22601
• 

  

  

  /25

  $275,000

  • 2 Beds
  • 1 Bath
  • 572 Sq Ft

  177 Dicks Hollow Rd, Winchester, VA 22603

  Adorable and fully renovated 2-bedroom, 1-bath bungalow just minutes from Winchester Medical Center! You’ll love the spacious open layout that connects the living room and kitchen, complete with brand-new stainless steel appliances and beautiful LVP flooring throughout. The large bedrooms offer plenty of space to relax, and the laundry/mudroom adds extra convenience. The bright bathroom features

  Amy Emerson-Kerns Cambridge Premier Realty, LLC.

  177 Dicks Hollow Rd, Winchester, VA 22603
• 

  

  

  /98

  $419,000

  • 3 Beds
  • 2 Baths
  • 2,325 Sq Ft

  1133 Tomahawk Trail, Winchester, VA 22602

  Nestled in the serene Shawneeland community, this exquisite chalet-style residence offers a perfect blend of rustic charm and modern comfort. Set against a backdrop of breathtaking mountain views and scenic vistas, this home is a sanctuary for those seeking tranquility and an exclusive lifestyle. As you approach the property, the warm cedar exterior invites you in, exuding a sense of timeless

  Sue Goodwin Long & Foster Real Estate, Inc.

  1133 Tomahawk Trail, Winchester, VA 22602
• 

  

  

  /62

  $560,000

  • 4 Beds
  • 3.5 Baths
  • 3,132 Sq Ft

  308 Lehigh Dr, Winchester, VA 22602

  IF you are looking for a deal, this is IT! Welcome to 308 Lehigh Drive, a beautifully updated and move-in ready home offering the perfect blend of space, style, and comfort. Built in 2023 - this modern, open-concept floor plan is filled with natural light and designed for effortless everyday living and impressive entertaining. The heart of the home is the chef’s kitchen, complete with a gas

  Sean Smith Real Broker, LLC

  308 Lehigh Dr, Winchester, VA 22602
• 

  

  /46

  $575,000 New Construction

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

  253 Rossmann Blvd, Winchester, VA 22602

  Move-In Ready New Construction with Builder Incentives! Select inventory homes in Winchester, VA, are now offering builder-paid buyer incentives. Homes are vacant, move-in ready, and include 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

  Marisa Varley ERA Oakcrest Realty, Inc.

  253 Rossmann Blvd, Winchester, VA 22602
• 

  

  /35

  $290,000

  • 2 Beds
  • 1 Bath
  • 1,176 Sq Ft

  239 Chestnut St, Winchester, VA 22601

  ******Price Reduction******239 Chestnut Street is a charming rancher in the heart of Winchester. 2 bedrooms, 1 bath, a large rear deck, eat in kitchen, laundry room could be converted into a third bedroom. Building in the back yard could be used as storage or a 1 car garage. This is a solid starter or downsizing home convenient to shopping,schools and parks. A little TLC will go a long way

  William Wertz Wildhawks Realty LLC

  239 Chestnut St, Winchester, VA 22601
• 

  

  /32

  $395,000

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

  151 Mccormick Cir Unit 201, Winchester, VA 22602

  Price improvement!! Experience Effortless 55+ Living at Winchester Landing – The Sapphire by Ryan Homes Discover the perfect blend of comfort and convenience in the Sapphire model, a spacious single-level condo offering over 1,500 sq. ft. of thoughtfully designed living space. The open-concept layout seamlessly connects a modern kitchen, large island, and bright great room, creating an inviting

  

  Rhonda Shade

  ERA Oakcrest Realty, Inc.

  (540) 787-2320

  151 Mccormick Cir Unit 201, Winchester, VA 22602
• 

  

  /48

  $520,000

  • 5 Beds
  • 4 Baths
  • 2,288 Sq Ft

  144 Morning Glory Dr, Winchester, VA 22602

  Motivated Seller! Extraordinary 5-Bedroom Home with Pool and Dual Kitchens in Winchester This exceptional 5-bedroom, 3.5-bathroom home — complete with a private office — offers comfort, functionality, and modern elegance. Thoughtfully designed for both everyday living and relaxed entertaining, this residence features two fully renovated kitchens (one on the main level and one in the walkout

  Julieta Russell Keller Williams Realty Dulles

  144 Morning Glory Dr, Winchester, VA 22602
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  /59

  $635,000

  • 4 Beds
  • 3.5 Baths
  • 4,632 Sq Ft

  930 Wayne Dr, Winchester, VA 22601

  Beautiful brick-front Colonial in a prime location! Nestled in a quiet neighborhood yet just minutes from I-81 and local amenities, this stunning home offers the perfect blend of convenience and tranquility.Step into the grand two-story foyer, flanked by a formal living room and dining room accented with elegant columns and a cozy fireplace. To the right, you’ll find a spectacular

  Elizabeth Flood Keller Williams Realty

  930 Wayne Dr, Winchester, VA 22601
• 

  

  /46

  $498,119 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,181 Sq Ft

  108 Keystone, Winchester, VA 22603

  Embrace the Vera 30-F2 – Homesite 1094 at Hiatt Pointe—a two-car, front-load garage villa with three bedrooms, two full bathrooms, and one half bathroom is ready for you to move in IMMEDIATELY. Be welcomed by 9’ ceilings on both levels, oak main stairs, and expertly selected finishes that make this villa feel effortlessly unique. The kitchen, central to the entire home, is complete with

  Shannon L Bray Pearson Smith Realty, LLC

  108 Keystone, Winchester, VA 22603
• 

  

  /51

  $414,999

  • 3 Beds
  • 2 Baths
  • 2,131 Sq Ft

  204 Ridge Rd, Winchester, VA 22602

  Well maintained brick Rancher(upgraded vinyl clad tilt windows,newer architectural roof) on a full basement on the east side of Winchester featuring over 2100 sqft of finished living space that offers true hardwood flooring on the main level with 3 bedrooms and 1 full bath. Spacious living room that features a gas log fireplace that has a woodstove insert included. Basement is 90% finished with a

  James Amick RE/MAX Roots

  204 Ridge Rd, Winchester, VA 22602
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  /69

  $605,000

  • Studio
  • 4,396 Sq Ft

  540 Monticello St, Winchester, VA 22601

  Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location!Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers

  Laura King MarketPlace REALTY

  540 Monticello St, Winchester, VA 22601
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  /41

  $485,000

  • 4 Beds
  • 3.5 Baths
  • 3,884 Sq Ft

  700 Crow Dr, Winchester, VA 22602

  Motivated Sellers!!! willing to negotiate a reasonable offer. Welcome to 700 Crow Drive, situated in the beautiful Wilde Acres subdivision in Frederick County, VA. This lovingly cared for and well-maintained three-level colonial home offers four bedrooms and three and a half baths, showcasing both space and style throughout. Priced below the tax assessment, this home presents an incredible

  Deisi Hernandez Fairfax Realty Select

  700 Crow Dr, Winchester, VA 22602
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  /20

  $455,000

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

  2250 Roosevelt Blvd, Winchester, VA 22601

  Sellers are highly motivated and ready to make a deal!Beautifully Renovated Single-Family Home with a little Pool, Workshop, and Detached GaragesWelcome to this stunning fully renovated 4-bedroom, 3-bathroom single-family home that perfectly blends comfort, style, and functionality. Step inside to find an open-concept layout filled with natural light, ideal for both everyday living and

  Silvana Rojas Spring Hill Real Estate, LLC.

  2250 Roosevelt Blvd, Winchester, VA 22601
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  /18

  $598,990 New Construction

  • 3 Beds
  • 2 - 3 Baths
  • 3,213 Sq Ft

  Drexel Plan at Abrams Pointe, Winchester, VA 22602

  The Drexel home design is a spacious and versatile single-family home designed to suit a variety of lifestyles. With 3,213 finished square feet, the Drexel offers generous living space that can be customized to meet your needs. It features main-level living with three bedrooms, including a private master suite with a walk-in closet and en-suite bathroom, along with two full bathrooms and a 2-car

  Maronda Homes Builder

  161 Williamson Rd Unit 38167756, Winchester, VA 22602
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  /42

  $549,990 New Construction

  • 3 - 4 Beds
  • 2 - 3 Baths
  • 2,418 Sq Ft

  Avalon Plan at Abrams Pointe, Winchester, VA 22602

  The Avalon home design by Maronda Homes blends elegant design with everyday functionality to create a home that's both stylish and smart. With 3 bedrooms, 2 bathrooms, and 2,418 square feet of living space, the Avalon is ideal for those looking for main-level living. As soon as you walk in, you will be greeted by a spacious, open-concept layout. The main level includes the option to convert a

  Maronda Homes Builder

  161 Williamson Rd Unit 38167752, Winchester, VA 22602
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  /86

  $2,125,000

  • 5 Beds
  • 4 Baths
  • 4,166 Sq Ft

  1631 Back Mountain Rd, Winchester, VA 22602

  This unique property is the definition of an oasis in the woods. Surrounded by 180 glorious private acres, this home dazzles with grandeur while blending natural elements that mesh with the environment. The handsome hunter green standing seam metal roof with matching accents against wood siding is the ideal look for this 4,166 square foot architectural marvel. Indoors, there’s a thoughtful

  Dan Whitacre Colony Realty

  1631 Back Mountain Rd, Winchester, VA 22602
• 

  

  /22

  $549,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,658 Sq Ft

  Homesite 195 Malbec, 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 Avalon is a beautiful 3-bedroom, 2 bath home with up to 2,538 square feet of living space. This single-family home design features main-level living with an open floor plan, highlighted by a spacious great room, a light-filled kitchen, and a

  Dorelba Estrada New Home Star Virginia, LLC

  Homesite 195 Malbec, Winchester, VA 22602
• 

  

  /23

  $514,929 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,195 Sq Ft

  119 Wagtail Ln, Winchester, VA 22603

  MOVE IN READY HOME AND OFFERING UP TO $15,000 IN CLOSING COST ASSISTANCE WITH USE OF VAN METRE'S PREFERRED LENDER/TITLE CO. 55+ Active Adult living just got better in Winchester Virginia with Hiatt Pointe, Van Metre Homes newest gated community. You have to come see for yourself this stunning new villa home. Hiatt Pointe is a resort style community and has it all clubhouse, swimming pool, hot

  Cynthia Butler Samson Properties

  119 Wagtail Ln, Winchester, VA 22603
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  /88

  $435,000

  • Studio
  • 2,152 Sq Ft

  26 A Jackson Ave, Winchester, VA 22601

  Rare Opportunity: Turnkey Duplex in Winchester – Vacant, Updated, and Ready for Your Next Move! A rare and an exceptional opportunity to own a two-unit duplex in Winchester City— vacant and ready for your plans. Whether you’re an investor seeking strong cash flow or an owner-occupant looking to live in one unit and rent the other, this property offers flexibility, income potential, and low

  

  Melanie Lucero

  Real Broker, LLC

  (540) 386-1285

  26 A Jackson Ave, Winchester, VA 22601
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  /66

  $1,200,000

  • Land
  • 124 Acres
  • $9,677 per Acre

  0 Frog Hollow Rd Unit LotWP001, Winchester, VA 22603

  Here’s a piece of pristine land on the market for the first time since the late 70’s with nearly endless possibilities for the next owner(s). This property is located north of Winchester and very near the West Virginia line. This prime piece of real estate has been family-owned and operated for decades. It is a mix of mostly flat hay ground and wooded acreage that stretches to the top

  Chad Pangle Whitetail Properties Real Estate

  0 Frog Hollow Rd Unit LotWP001, Winchester, VA 22603
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  /72

  $699,900

  • 4 Beds
  • 3.5 Baths
  • 3,475 Sq Ft

  132 Amherst St, Winchester, VA 22601

  Step back in time with this Beautifully preserved VICTORIAN Brick Home Built in 1880, a true piece of Winchester's history. This is a Registered Historic Property that showcases original architectural details, high ceilings, ornate trim, and original wood floors that reflect the artistry of a bygone era. A Well Designed Addition has allowed for generous space along with modern comfort and

  Jodi Costello ERA Oakcrest Realty, Inc.

  132 Amherst St, Winchester, VA 22601
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  /58

  $635,000

  • 6 Beds
  • 4 Baths
  • 2,672 Sq Ft

  220 Snappy Ln, Winchester, VA 22602

  This stunning two-level home sits on a flat, picturesque 5 acre acre lot, offering endless possibilities for the right buyer.Adding the two lots together is 7.44 acres.The basement was completely remodeled in 2025, featuring a brand-new kitchen, a full bathroom, and plenty of open living space—perfect for guests, recreation, or rental potential. A property with this much land and

  Mauricio Argandona Fairfax Realty Select

  220 Snappy Ln, Winchester, VA 22602
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  /3

  $1,200,000

  • Land
  • 2.38 Acres
  • $504,202 per Acre

  0 Prosperity Dr, Winchester, VA 22602

  2.38 Acres at the intersection of Valley Pike and Prosperity Drive. Located in the Kernstown area of Frederick County/Winchester. Property is located across from the street from CMA Honda, Aldi Supermarket, Outback Steakhouse, and Carrabba's Italian Grill & Restaurant. Located in close proximity to the intersection of I-81, US Route 37, and US Route 11. Excellent signage opportunities,

  H. Paige Manuel Oakcrest Commercial LLC.

  0 Prosperity Dr, Winchester, VA 22602
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  /62

  $1,200,000

  • Land
  • 124 Acres
  • $9,677 per Acre

  0 Frog Hollow Rd, Winchester, VA 22603

  Here’s a piece of pristine land on the market for the first time since the late 70’s with nearly endless possibilities for the next owner(s). This property is located north of Winchester and very near the West Virginia line. This prime piece of real estate has been family owned and operated for decades. Mix of mostly flat hay ground and wooded acreage that stretches to the top of North Mountain.

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Frog Hollow Rd, Winchester, VA 22603
• 

  /2

  $60,000

  • Land
  • 0.58 Acre
  • $103,448 per Acre

  0 0 Unit VAFV2036672, Winchester, VA 22602

  Kelly Hayes Samson Properties

  0 0 Unit VAFV2036672, Winchester, VA 22602
• 

  

  /44

  $496,129 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,195 Sq Ft

  117 Wagtail Ln, Winchester, VA 22603

  Embrace the Vera 30-F2 – Homesite 1031 at Hiatt Pointe—a two-car, front-load garage VILLA with three bedrooms, two full bathrooms, and one half bathroom will be ready IMMEDIATELY. The kitchen, central to the entire home, is complete with light brown soft-close cabinetry, white quartz countertops, an island with a built-in trash can, and a pantry with solid shelving off the mud room. The Samsung®

  Shannon L Bray Pearson Smith Realty, LLC

  117 Wagtail Ln, Winchester, VA 22603
• 

  

  /40

  $650,434 New Construction

  • 3 Beds
  • 3 Baths
  • 3,200 Sq Ft

  116 Magpie Ln, Winchester, VA 22603

  Step into the Sierra 39-F2 – Homesite 1037 at Hiatt Pointe (55+)—a two-car, front-load garage SINGLE FAMILY home with three bedrooms and three full bathrooms will be ready IMMEDIATELY. Designed for ease and everyday function, this factory-framed floorplan is as innovative as it stylish! Enter through the inviting front porch and be immediately welcomed by 9’ ceilings on both levels, oak main

  Shannon L Bray Pearson Smith Realty, LLC

  116 Magpie Ln, Winchester, VA 22603
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  /115

  $469,999

  • 5 Beds
  • 3 Baths
  • 2,080 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

  Waqas Abbasi Lifestyle Realty, LLC.

  419 Summit Ave, Winchester, VA 22601
• 

  

  /38

  $335,000

  • 4 Beds
  • 1.5 Baths
  • 1,411 Sq Ft

  298 Bufflick Rd, Winchester, VA 22602

  Meet Convenience with Old World Charm!Welcome to this beautifully renovated home just minutes from Winchester. New is the key to loving this property—with updates inside and out that provide comfort, efficiency, and style.This spacious home features 4 bedrooms, a fully renovated full bath upstairs, and a renovated half bath on the main level. The kitchen has been completely redone with

  Mary Cox Berkshire Hathaway HomeServices PenFed Realty

  298 Bufflick Rd, Winchester, VA 22602
• 

  

  /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 Corcoran McEnearney

  LOT 5A Fox Trail, Winchester, VA 22602
• 

  

  /32

  $540,000

  • 3 Beds
  • 2 Baths
  • 1,829 Sq Ft

  105 Lenore Ln, Winchester, VA 22602

  Showcase-quality living without the new-construction wait. This former Richmond American model home has been meticulously maintained and loaded with premium builder upgrades and designer finishes throughout. The single-level layout offers 3 bedrooms, 2 baths, and 1,829 square feet of bright, open living space highlighted by high ceilings and thoughtful details at every turn. The kitchen is the

  Barton Chasler Realty ONE Group Old Towne

  105 Lenore Ln, Winchester, VA 22602
• 

  

  /26

  $379,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,660 Sq Ft

  129 Indiana Trail, Winchester, VA 22602

  I am done! Large lot on private street with valley views and private. HW floors entire main floor and stairs, tile floors in all baths, BUILDER BONUS HARDWOOD TO INCLUDE BEDROOMS (no carpet in house), UPGRADED CABINETS, GRANITE COUNTERTOPS IN KITCHEN. New Colonial home. 3 bed, 2.5 full baths, open floor plan, family rm, Kitchen w/ island and breakfast rm & sep. dining rm, Lg owner suite & true

  Jim Thomson Realty ONE Group Old Towne

  129 Indiana Trail, Winchester, VA 22602
• 

  

  /7

  $235,000

  • Land
  • 17.8 Acres
  • $13,202 per Acre

  0 Dr, Winchester, VA 22603

  Outstanding Opportunity – 17.80 Acres in Winchester, VAEmbrace the beauty and serenity of Virginia’s countryside with this expansive 17.80-acre parcel, ideally boarder's both sides of Snake Drive. The property showcases rolling topography and walkable terrain, offering a picturesque setting for your future home, weekend retreat, or recreational getaway.This parcel has an approved perk

  Jocelyn Tweedie Coldwell Banker Premier

  0 Dr, Winchester, VA 22603
• 

  

  /67

  $399,999

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  707 E Cork St, Winchester, VA 22601

  Don't let this location fool you - Plenty of parking on the side and back of the home and a large turn around space to exit onto Cork St easily! Centrally located colonial with gorgeous hardwood flooring and trim throughout! Step back in time, but enjoy all of the modern amenities with easy access to Jim Barnett Park just down the street, downtown walking mall and commuter roads, and even views

  Misty Weaver Samson Properties

  707 E Cork St, Winchester, VA 22601
• 

  

  /36

  $410,000

  • 4 Beds
  • 3.5 Baths
  • 2,261 Sq Ft

  125 Cheshire Ct, Winchester, VA 22602

  Beautiful and well-maintained 4 bedroom, 3.5 bath townhouse at the end of a quiet cul-de-sac on the east side of Winchester. Conveniently located to Rt 7 and I-81 and historic downtown Winchester. The 3-level townhouse backs to a wooded tree area and has a fenced rear yard. New luxury vinyl floor installed in majority of the home. As you enter, you will be welcomed into a large foyer with

  Eric Kronenwetter RE/MAX Roots

  125 Cheshire Ct, Winchester, VA 22602
• 

  

  /51

  $479,900

  • 3 Beds
  • 4 Baths
  • 3,359 Sq Ft

  227 Miller St, Winchester, VA 22601

  Welcome to 227 Miller Street — a home that instantly feels inviting. Recent improvements include new flooring in both upstairs and downstairs bathrooms (2025), new toilets in all bathrooms (2024), refreshed hardwood floors (2025), a professionally cleaned chimney (2025), a new sump pump (2025), and a fully dug-out and waterproofed basement completed in 2025. The back deck was replaced in 2024,

  Leah Marabella Realty ONE Group Old Towne

  227 Miller St, Winchester, VA 22601
• 

  

  /42

  $503,929 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,181 Sq Ft

  116 Keystone, Winchester, VA 22603

  Embrace the Vera 30-F2 – Homesite 1097 at Hiatt Pointe—a two-car, front-load garage END UNIT VILLA with three bedrooms, two full bathrooms, and one half bathroom will be ready IMMEDIATELY. Be welcomed by 9’ ceilings on both levels, oak main stairs, and expertly selected finishes that make this villa feel effortlessly unique. The kitchen, central to the entire home, is complete with soft-close

  Shannon L Bray Pearson Smith Realty, LLC

  116 Keystone, Winchester, VA 22603
• 

  

  /63

  $365,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  508 Grouse Dr, Winchester, VA 22602

  Nestled in the charming Wilde Acres community, this stunning new construction home, completed in 2025, offers a perfect blend of modern design and traditional comfort. The Colonial architectural style, adorned with durable vinyl siding, invites you into a warm and welcoming space. Step inside to discover a thoughtfully designed interior featuring a traditional floor plan that seamlessly connects

  Steve DuBrueler Coldwell Banker Premier

  508 Grouse Dr, Winchester, VA 22602

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