Winchester, VA Homes for Sale

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  $459,000

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

  2250 Roosevelt Blvd, Winchester, VA 22601

  Charming Cape Cod nestled in a quiet residential neighborhood, just minutes from Route 11 and I-81 for easy commuting. This light-filled home welcomes you with a bright living room featuring a stunning stone fireplace as its centerpiece. The cabinet-packed kitchen is the heart of the home and offers granite countertops and a bar-height peninsula that opens seamlessly to the living room . The main

  Heloisa Amar Samson Properties

  2250 Roosevelt Blvd, Winchester, VA 22601
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  $950,000

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

  226 Summerfield Dr, Winchester, VA 22602

  Nestled in the charming and sought-after Raven Pointe neighborhood,adjacent to farmland yet 7 minutes from Old Town Winchester, thisstunning Colonial home offers a perfect blend of modern comfort andtimeless elegance. This spacious residence boasts 4,714 finishedsquare feet, providing ample room for both relaxation andentertainment. Front porch entrance greets guests with a

  Rebecca Sims Century 21 Redwood Realty

  226 Summerfield Dr, Winchester, VA 22602
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  $629,900

  • 3 Beds
  • 2 Baths
  • 2,834 Sq Ft

  126 Harvest Ridge Dr, Winchester, VA 22601

  This meticulously cared-for home is located in the sought-after 55+ community The Village at Harvest Ridge, where comfort and convenience meet. Step inside to find hardwood floors that flow through the main level, connecting open and light-filled spaces. Premier 55+ and better community - The Village at Harvest Ridge. Exceptional Home, approximately 5000 square feet home, gourmet kitchen,

  Susan Raburn Long & Foster Real Estate, Inc.

  126 Harvest Ridge Dr, Winchester, VA 22601
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  /20

  $374,990 New Construction

  • 3 Beds
  • 4 Baths
  • 1,910 Sq Ft

  105 Boone Ct, Winchester, VA 22602

  Brand New! Move-in ready at Rossum Crossing townhome community, conveniently located near shopping and dining options. The St. Paul Townhome features three bedrooms, two full and two half baths, and a one-car garage. The main floor boasts an open-concept floor plan, with a spacious family room that flows into a fully equipped kitchen. The kitchen includes an island, a pantry closet, and a

  Dorelba Estrada New Home Star Virginia, LLC

  105 Boone Ct, Winchester, VA 22602
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  $1,325,000

  • 5 Beds
  • 4.5 Baths
  • 4,100 Sq Ft

  100 Country Club Cir, Winchester, VA 22602

  This regal 1950s Colonial, named Eagle Gate, sits atop a knoll overlooking 6.34 pastoral acres on the east side of Winchester. This elegant home dazzles with nearly 4,000 finished square feet, three levels, five bedrooms, 4.5 baths, an expansive garage, a swimming pool, and renovations and updates that elevate the living experience to decadent. Majestic pillars are the hallmark of the handsome

  Dan Whitacre Colony Realty

  100 Country Club Cir, Winchester, VA 22602
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  /4

  $9,500

  • Land
  • 0.25 Acre
  • $38,000 per Acre

  Lot 5 Quail, Winchester, VA 22602

  Discover a serene 0.25-acre lot nestled in Winchester's Wilde Acres subdivision, where nature meets tranquility. This beautifully wooded parcel offers a perfect canvas for your dream home, surrounded by lush trees that provide both privacy and a picturesque backdrop. With convenient road frontage, access to your future home or cozy weekend retreat is effortless. The enchanting views of the

  Bridget Aikens Colony Realty

  Lot 5 Quail, Winchester, VA 22602
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  $429,000

  • 4 Beds
  • 3 Baths
  • 1,783 Sq Ft

  570 Welltown Rd, Winchester, VA 22603

  Built to last but updated and move in ready! This charming brick home has a lot to offer. The location is perfect with quick access to I-81 for commuting, is only minutes away from restaurants, shopping and other amenities, and maybe best of all, it has a separate in-law suite on the lower level (tenant is currently on a month to month lease and is happy to stay if new owner allows)! The basement

  Marielle Thoburn Keller Williams Realty

  570 Welltown Rd, Winchester, VA 22603
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  $282,500

  • 2 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  128 Little River Dr, Winchester, VA 22602

  3% SELLER SUBSIDY TO BUYER AT CLOSING! TURN KEY and in EXCELLENT CONDITION! Finished basement that adds additional office space, bonus room, etc. Walk out basement and adjacent to neighborhood playground! Natural light throughout and hardwood floors. COOL HVAC! Freshly painted, TONS OF STORAGE, and eat in HUGE KITCHEN! Enjoy your AWESOME DECK that overlooks the playground and peaceful,

  Richard Butcher Coldwell Banker Premier

  128 Little River Dr, Winchester, VA 22602
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  $499,000 Open Sat 3PM - 6PM

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  823 Woodland Ave, Winchester, VA 22601

  Charming on the outside, modern on the inside Located in the heart of charming Old Town, this home offers the perfect blend of timeless character and a fully modern renovation. Featuring 3 beautifully updated levels, the home showcases new Bruce hardwood flooring throughout with no transitions—creating a seamless, elegant flow and easy mobility. Every detail has been thoughtfully upgraded while

  Lenora Zaccur Coldwell Banker Realty

  823 Woodland Ave, Winchester, VA 22601
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  $399,990 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
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  /8

  $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
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  /11

  $599,990 New Construction

  • 3 Beds
  • 1 Bath
  • 2,812 Sq Ft

  108 Lawford, Winchester, VA 22603

  Experience the epitome of modern living in the Matisse. This thoughtfully designed home offers main-level living at its finest, providing unparalleled comfort and flexibility to suit your unique lifestyle. The heart of the home is an open-concept haven, seamlessly blending a gourmet kitchen, dining room, and spacious family room. The kitchen, a chef's dream, features a functional island, abundant

  Brookfield Residential Builder

  108 Lawford, Winchester, VA 22603
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  $509,000

  • 4 Beds
  • 3 Baths
  • 1,935 Sq Ft

  4494 Cedar Creek Grade, Winchester, VA 22602

  Escape to Your Private Almost 3-Acre Oasis: The Ultimate Modern Homestead!Rarely does a property offer the perfect synergy of a high-end interior renovation and a fully functional hobby farm. Nestled on a lush, 2.87-acre lot, this stunning 4-bedroom, 3-full bath home has been reimagined from top to bottom. As you enter the circular driveway lined with budding spring trees, you’ll feel the

  Jaclyn Michelle Berkshire Hathaway HomeServices PenFed Realty

  4494 Cedar Creek Grade, Winchester, VA 22602
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  /55

  $434,999

  • 4 Beds
  • 2.5 Baths
  • 2,850 Sq Ft

  1105 Henry Dr, Winchester, VA 22602

  Home offers nearly 3000 sqft of finished living space that has Luxury Vinyl flooring through out both levels (absolutely no carpet) that features 4 bedrooms and 2.5 baths situated on over a 1/2 acre (.61) of ground. Upon entering you will find an open floor plan that encompasses a large living room and dining room with canned lighting then pours into the large eat in kitchen (new appliances) that

  James Amick RE/MAX Roots

  1105 Henry Dr, Winchester, VA 22602
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  /2

  $3,200,000

  • Land
  • 451 Acres
  • $7,095 per Acre

  472 Mccubbin, Winchester, VA 22601

  Adrian Small TTR Sotheby's International Realty

  472 Mccubbin, Winchester, VA 22601
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  /2

  $465,000 Coming Soon

  • 1,771 Sq Ft

  303 Asbury Rd, Winchester, VA 22602

  Nestled in the charming Pioneer Heights, this delightful Colonial-style custom home offers a perfect blend of comfort and functionality. With 1,771 square feet of living space, this residence invites you to create lasting memories. The warm ambiance is enhanced by a cozy fireplace, perfect for those chilly evenings spent with loved ones. Set on a generous half acre lot, the outdoor space provides

  Brad Meletti Samson Properties

  303 Asbury Rd, Winchester, VA 22602
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  /7

  $1,045,000 New Construction

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

  60 Gravenstein Ct, Winchester, VA 22602

  DECORATED MODEL HOME located at 156 Covey Lane Winchester VaOpen SATURDAYS and SUNDAYS from 11am to 5pmCall Sales Manager for Appointment MAIN LEVEL LIVING in an Idyllic Setting - Welcome to Stonymeade ! -2 acre Home Site in Winchester Virginia Base price shown is for the Dogwood MAIN LEVEL LIVING FLOORPLAN and we have many other plans including those with first floor primary suites,

  Daniel Boris Pearson Smith Realty, LLC

  60 Gravenstein Ct, Winchester, VA 22602
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  /3

  $3,200,000

  • Land
  • 13.05 Acres
  • $245,211 per Acre

  0 0 Northwestern Pike, Winchester, VA 22602

  Prime opportunity on 13.05 acres in an unbeatable high-visibility location along Route 50 in Winchester, VA. Positioned directly across from major retailers and conveniences—including Walmart, Sheetz, Tractor Supply, Applebee’s, Dunkin’, Bojangles, and the Winchester Medical Center campus—this property offers exceptional exposure and accessibility. Zoned for multiple development possibilities,

  Sarah Reynolds Keller Williams Realty

  0 0 Northwestern Pike, Winchester, VA 22602
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  $850,000 New Construction

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

  Lot 5 Keval Gyan Way, Winchester, VA 22603

  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 large family living in this

  Jim Thomson Realty ONE Group Old Towne

  Lot 5 Keval Gyan Way, Winchester, VA 22603
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  $889,000 Open Sat 1PM - 3PM

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

  107 Launchris Dr, Winchester, VA 22602

  Step into timeless elegance with this stately Colonial, set on nearly an acre of picturesque land. Blending classic charm with thoughtful modern upgrades, this home offers the perfect balance of comfort, space, and sophistication. The current owner has invested over $150,000 in upgrades since purchasing, 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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  $479,000

  • 3 Beds
  • 2 Baths
  • 1,703 Sq Ft

  231 Bentley Ave, Winchester, VA 22602

  Easy main-level living with bonus space when you need it—this one just works. A beautiful, covered front porch welcomes you into a foyer that opens to a comfortable living room centered around a gas fireplace with built-ins, creating a space that feels both open and inviting. Toward the rear of the home, the dining area is filled with natural light from well-placed windows. The kitchen is

  Natalie Langford ERA Oakcrest Realty, Inc.

  231 Bentley Ave, Winchester, VA 22602
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  $609,990 New Construction

  • 4 Beds
  • 3 Baths
  • 1,748 Sq Ft

  121 Scented Rose 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

  121 Scented Rose Way, Winchester, VA 22602
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  $9,500

  • Land
  • 0.55 Acre
  • $17,273 per Acre

  LOTS 8 & 9 Elk Trail, Winchester, VA 22602

  Great opportunity to own two beautiful wooded lots full of mature trees and plenty of privacy! These adjoining parcels offer a wonderful chance to connect with nature and enjoy peaceful surroundings. Located just about 30 minutes from downtown Winchester, you get the perfect mix of country calm and town convenience. Whether you’re thinking about outdoor fun, future plans, or simply an investment,

  Kristin Crosby Samson Properties

  LOTS 8 & 9 Elk Trail, Winchester, VA 22602
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  $1,049,900 New Construction

  • 3 Beds
  • 3.5 Baths
  • 3,100 Sq Ft

  2225 Cedar Grove Rd, Winchester, VA 22603

  4-6-26 Cabinets in. Painted,, trimmed, and hardwood floors stained and finished. Getting close. Delivery estimated April.At front of Keplinger Estates near the Apple Pie Ridge area.Seize a truly unique opportunity to own a brand-new, luxury estate set on over 7 acres of private, wooded land. While this stunning property sits at the entrance to the prestigious, upper-scale 15-lot Keplinger

  Jim Thomson Realty ONE Group Old Towne

  2225 Cedar Grove Rd, Winchester, VA 22603
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  $450,000

  • 4 Beds
  • 2.5 Baths
  • 2,072 Sq Ft

  129 Doonbeg Ct, Winchester, VA 22602

  ENJOY YOUR RETIREMENT! Newer, beautifully maintained 4-bedroom home with open floor plan and upgrades. On a pleasant cul-de-sac in Cottage Glen, an age 55-plus community that's convenient to I-81 and Rt. 37 and near restaurants, shopping, services, regional Medical Center and historic downtown Winchester. National publications and TV have hailed Winchester as a prime location for retirement.

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  129 Doonbeg Ct, Winchester, VA 22602
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  $579,900

  • 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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  /4

  $9,500

  • Land
  • 0.25 Acre
  • $38,000 per Acre

  Lot 6 Quail Dr, Winchester, VA 22602

  Discover a serene 0.25-acre lot nestled in Winchester's Wilde Acres subdivision, where nature meets tranquility. This beautifully wooded parcel on Quail Drive offers a perfect canvas for your dream home, surrounded by lush trees that provide both privacy and a picturesque backdrop. With convenient road frontage, access to your future home or cozy weekend retreat is effortless. The

  Bridget Aikens Colony Realty

  Lot 6 Quail Dr, Winchester, VA 22602
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  /14

  $359,990 New Construction

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

  119 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

  119 Castaway Place, Winchester, VA 22603
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  /30

  $320,000

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  2912 2nd St, Winchester, VA 22601

  2912 2nd Street — a cozy 3-bedroom, 1-bath ranch-style home offering comfortable single-level living in Winchester. The home opens to a light-filled living area with hardwood floors that add warmth and character, creating an inviting space to relax or gather. The eat-in kitchen provides practical workspace, with an easy flow that keeps everything connected. Both bedrooms are located on the main

  Sabrina Priest Preslee Real Estate

  2912 2nd St, Winchester, VA 22601
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  $767,900

  • 3 Beds
  • 3 Baths
  • 2,112 Sq Ft

  1049 Laurel Grove Rd, Winchester, VA 22602

  This custom-built 3-bedroom, 3-bath home is perfectly positioned on a private, wooded lot with sweeping mountain views and a sense of seclusion. The setting feels like a peaceful retreat, offering a serene, park-like atmosphere while still providing convenient access to everyday amenities. The main-level primary suite is a standout, featuring an elegant bathroom with a walk-in shower and a

  LESLIE WEBB Long & Foster Real Estate, Inc.

  1049 Laurel Grove Rd, Winchester, VA 22602
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  $399,000

  • 3 Beds
  • 2 Baths
  • 1,999 Sq Ft

  520 N Braddock St, Winchester, VA 22601

  Welcome to this charming home in the heart of Winchester offering character, natural light, and a highly walkable location.This home features 3 bedrooms and 2 full bathrooms, with all bedrooms located on the upper level. At the top of the stairs you’ll find a spacious primary bedroom filled with natural light, creating a bright and inviting retreat. Large windows throughout the home allow

  Angela Duncan MarketPlace REALTY

  520 N Braddock St, Winchester, VA 22601
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  /55

  $473,500

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

  620 Crystal Ct, Winchester, VA 22601

  Back and better than EVER! New Sales Price!! Rare Cul-de-Sac Gem in the Heart of Winchester! Now priced nearly $20,000 under appraisal value!! Discover the perfect blend of tranquility and city convenience at 620 Crystal Court. Situated in a sought-after, quiet cul-de-sac right in the center of Winchester, this stunning 4-bedroom, 2.5-bathroom residence has been thoughtfully updated and is ready

  VAIBHAV AGARWAL Realty FC, LLC

  620 Crystal Ct, Winchester, VA 22601
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  $535,000 Open Sat 1PM - 3PM

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

  253 Rossmann Blvd, Winchester, VA 22602

  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, open-concept main level features a spacious kitchen with a large island, perfect for

  Marisa Varley ERA Oakcrest Realty, Inc.

  253 Rossmann Blvd, Winchester, VA 22602
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  $574,900

  • 4 Beds
  • 2.5 Baths
  • 2,428 Sq Ft

  104 Monet Terrace, Winchester, VA 22602

  Located in an established cul-de-sac this 4 bedrooms, 2 1⁄2 bath, home has an unfinished basement. Also a deep two vehicle garage and storage building with a fenced yard and rear covered porch. The kitchen has Corian counters and loads of beautiful cabinets, an arch pass through, and hardwood floors. The house has crown molding, chair rail, wainscoting and hardwood floors throughout the main

  Janet Jackson MarketPlace REALTY

  104 Monet Terrace, Winchester, VA 22602
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  $699,000

  • 4 Beds
  • 3.5 Baths
  • 3,120 Sq Ft

  256 Brookneil Dr, Winchester, VA 22602

  Step into something special at 256 Brookneil Dr—where space, privacy, and flexibility come together beautifully. Nestled on 2.1 wooded acres just minutes from Winchester, this property offers a peaceful retreat with the soothing sounds of nature all around. Whether you're sipping coffee on the deck or unwinding after a long day, the setting delivers the kind of tranquility that’s hard to find.

  Jacquelyn Sowers ERA Oakcrest Realty, Inc.

  256 Brookneil Dr, Winchester, VA 22602
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  $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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  /14

  $605,990 Open Sat 12PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 3,134 Sq Ft

  207 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 Carlisle Floorplan is a beautiful 4-bedroom, 2.5-bath home with up to 3,789 square feet of living space. This single-family home design features an open floor plan, highlighted by a spacious great room, a light-filled kitchen, and a breakfast area.

  Holly Horne Poole New Home Star Virginia, LLC

  207 Williamson Rd, Winchester, VA 22602
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  /2

  $365,000 Coming Soon

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

  113 Deer Trail, Winchester, VA 22602

  Welcome home to this beautifully updated 3 bed, 2 bath property in Winchester! Step inside to an open-concept kitchen complete with a center island, brand new stainless steel appliances, and stylish finishes—ideal for both everyday living and entertaining. The home has been freshly painted and boasts new LVP flooring throughout the main living areas and new carpet in the bedrooms, creating a

  Caleb Fowler Samson Properties

  113 Deer Trail, Winchester, VA 22602
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  /15

  $699,990 New Construction

  • 3 Beds
  • 2 Baths
  • 3,292 Sq Ft

  116 Sunflower Way, Winchester, VA 22603

  Welcome home to the Rockwell, a versatile main-level living home designed for your lifestyle. The Rockwell's open-concept main floor seamlessly blends the kitchen, breakfast nook, and family room, creating a spacious and inviting atmosphere. The kitchen is a culinary enthusiast's dream, featuring a functional island with optional extension, ample storage, and a butler's pantry. The adjacent

  Brookfield Residential Builder

  116 Sunflower Way, Winchester, VA 22603
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  /30

  $925,000

  • Land
  • 156.58 Acres
  • $5,908 per Acre

  950 Stony Hill Rd, Winchester, VA 22603

  A truly rare opportunity to own over 150 acres , just a few miles west of the scenic Shenandoah Valley—where rolling pasture, privacy, and possibility come together. 950 Stony Hill Rd. offers a stunning blend of open farmland and natural beauty. With significant portions of the land farmable, this property is perfectly suited for agricultural use, equestrian pursuits, or creating a remarkable

  Jennifer Watt Century 21 Redwood Realty

  950 Stony Hill Rd, Winchester, VA 22603

Showing Results 241 - 280, Page 7 of 10