Winchester, VA Homes

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  $1,595,000

  • Land
  • 158.44 Acres
  • $10,067 per Acre

  158.5 Acres Lot 3 Laurel Grove Rd, Winchester, VA 22602

  Incredible opportunity to own 158.443 acres of pristine, private land in an exclusive 3-lot, 440-acre subdivision. This is the most secluded parcel of the three, offering unmatched 360-degree panoramic views and a level of privacy that’s increasingly rare—yet just 15 minutes from town. Tucked away from the lights and sounds of civilization, this property provides a peaceful, off-the-beaten-path

  Nadeem Helfer Corcoran McEnearney

  158.5 Acres Lot 3 Laurel Grove Rd, Winchester, VA 22602
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  /38

  $2,700 per month

  • 4 Beds
  • 2.5 Baths
  • House for Rent

  218 Munsee Cir, Winchester, VA 22602

  Charming Brand-New 4-Bedroom Home in Premier Winchester Community – Available for RentBedrooms: 4 | Bathrooms: 2.5 | Approx. 1,953 sq ft Welcome to your ideal rental home! Nestled in the desirable Retreat at Winding Creek community, this recently built (2025) single-family residence offers modern comfort, thoughtful design and excellent location. Interior HighlightsBright and open main

  Sreedhar Maram Maram Realty, LLC

  218 Munsee Cir, Winchester, VA 22602
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  /71

  $779,000 Sold Sep 04, 2025

  251 Heather Hill Ln, Winchester, VA 22603

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 2002

  Last Sold Summary

  • $535/SF
  • 110 Days On Market

  Current Estimated Value $658,293

  Last Listing Agent Amber Jenkins Century 21 Redwood Realty

  251 Heather Hill Ln, Winchester, VA 22603
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  /19

  Est $333,091 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  2927 S Pleasant Valley Rd, Winchester, VA 22601

  2927 S Pleasant Valley Rd, Winchester, VA 22601
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  /55

  $685,000 Pending

  • 5 Beds
  • 4 Baths
  • 4,576 Sq Ft

  800 Lake Dr, Winchester, VA 22601

  Location Location Location! Welcome to 800 Lake Dr. Winchester VA 22601, Located in the highly sought-after Rolling Hills community and situated on a 0.37 acre lot, This expansive home offers 4,500+ sqft. of living space, featuring 5 bedrooms, 4 Full baths, finished basement, and 2 car garage! Step inside to find gleaming hardwood floors in the formal living and dining rooms. The unique

  Lisa Behr Coldwell Banker Premier

  800 Lake Dr, Winchester, VA 22601
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  /9

  $1,100 per month

  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  522 N Loudoun St Unit 2, Winchester, VA 22601

  Furnished efficiency ready for occupancy in downtown historic Winchester VA. Just a few blocks away from the downtown walking mall. 3 month minimum lease terms. Utilities included, electric with $100/per month limit and tenant pays anything over the amount. Coin op washer/dryer and off street parking. No animals, no smoking. VAR or NVAR rental application with $50/per person application fee paid

  Mandie Gladwell OliveTree Property Group, LLC

  522 N Loudoun St Unit 2, Winchester, VA 22601
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  /28

  $580,000 Sold Oct 24, 2025

  230 W Boscawen St, Winchester, VA 22601

  • 7,650 Sq Ft
  • Built 1891

  Last Sold Summary

  • $76/SF
  • 284 Days On Market

  Last Listing Agent Gillian Greenfield Coldwell Banker Premier

  230 W Boscawen St, Winchester, VA 22601
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  /21

  Est $326,591 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,060 Sq Ft

  2922 S Pleasant Valley Rd, Winchester, VA 22601

  2922 S Pleasant Valley Rd, Winchester, VA 22601
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  /12

  $632,990 New Construction

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

  5 Williamson Rd, Winchester, VA 22602

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

  Dick Bryan New Home Star Virginia, LLC

  5 Williamson Rd, Winchester, VA 22602
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  /27

  $2,100 per month

  • 3 Beds
  • 2.5 Baths
  • 1,442 Sq Ft
  • Townhouse for Rent

  623 Laurelwood Cir, Winchester, VA 22601

  Experience the best of contemporary living in the new Laurelwood Commons community, a serene enclave of just 34 newly constructed townhomes in the heart of Winchester. This community is designed for convenience and a tranquil lifestyle, with townhomes situated on a single, U-shaped street, creating a cozy and private feel. This new construction townhouse, completed in 2025, offers the perfect

  Jody Elson Dream Real Estate

  623 Laurelwood Cir, Winchester, VA 22601
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  /30

  $325,000 Sold Oct 20, 2025

  966 Woodstock Ln, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,529 Sq Ft
  • Built 1980

  Last Sold Summary

  • $213/SF
  • 31 Days On Market

  Last Listing Agent Anselm Tamasang Weichert Realtors - Blue Ribbon

  966 Woodstock Ln, Winchester, VA 22601
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  /23

  Est $354,325 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,388 Sq Ft

  2919 S Pleasant Valley Rd, Winchester, VA 22601

  2919 S Pleasant Valley Rd, Winchester, VA 22601
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  $434,990 New Construction

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

  127 Lakota St, Winchester, VA 22602

  Don't miss this fantastic Adams interior unit townhome with included deck, washer and dryer, and blinds! The Adams offers 4 bedrooms, 3.5 baths, and a 1-car garage spread across three levels with a total of 1,889 square feet. The main level features 9-foot ceilings, luxury vinyl plank flooring, white cabinets with granite countertops, and stainless steel appliances by Whirlpool. With all the

  D.R. Horton Builder

  127 Lakota St, Winchester, VA 22602
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  /26

  $1,750 per month

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft
  • House for Rent

  105 E Pall Mall St, Winchester, VA 22601

  SO AFFORDABLE! Spacious 3-bedroom house with 2 full baths, wood floors, fenced back yard. Near historic Old Town Winchester, Shenandoah University, shopping, services, museums and commuter routes 50, 7 and I-81. Laundry room with washer and dryer. Main-level bath has shower. Upstairs bath has tub. Eat-in kitchen with pantry. Kitchen appliances, washer and dryer included. 13 X 7 walk-in closet and

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  105 E Pall Mall St, Winchester, VA 22601
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  /17

  $379,990 Sold Mar 24, 2025

  109 Nootka Way, Winchester, VA 22602

  • 3 Beds
  • 2.5 Baths
  • 1,509 Sq Ft
  • Built 2024

  Last Sold Summary

  • $252/SF
  • 100 Days On Market

  Last Listing Agent Tracy Jennings D R Horton Realty of Virginia LLC

  109 Nootka Way, Winchester, VA 22602
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  /19

  Est $330,059 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  2951 S Pleasant Valley Rd, Winchester, VA 22601

  2951 S Pleasant Valley Rd, Winchester, VA 22601
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  /13

  $235,000 Under Contract

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

  129 Brookland Terrace Unit 1, Winchester, VA 22602

  Great two bedroom ,two bath condo. Very convenient first floor entrance. Zero steps. Great commuter location off Rt. 7

  John Scully Colony Realty

  129 Brookland Terrace Unit 1, Winchester, VA 22602
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  /10

  $1,199 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  3105 Shawnee Dr Unit 7, Winchester, VA 22601

  We invite you to make this 1943 Farmhouse converted into7 apartments your future home. The hallways have beenrecently renovated in addition to the apartment homes.Boasting 12+’ ceilings and original hardwood floors in thecorridors, join us and be part of the history of this greathome. This newly renovated one-bedroom, one bathroomapartment offers the best of all worlds.

  Steve DuBrueler Coldwell Banker Premier

  3105 Shawnee Dr Unit 7, Winchester, VA 22601
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  /34

  $309,000 Sold Feb 14, 2025

  302 Chatham Square, Winchester, VA 22601

  • 3 Beds
  • 3.5 Baths
  • 1,814 Sq Ft
  • Built 1995

  Last Sold Summary

  • $170/SF
  • 1 Day On Market

  Current Estimated Value $313,908

  Last Listing Agent Kerry Wysong Long & Foster Real Estate, Inc.

  302 Chatham Square, Winchester, VA 22601
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  /19

  Est $329,814 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  2947 S Pleasant Valley Rd, Winchester, VA 22601

  2947 S Pleasant Valley Rd, Winchester, VA 22601
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  /37

  $629,990 New Construction

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

  111 Scented Rose 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

  111 Scented Rose Way, Winchester, VA 22602
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  /32

  $2,650 per month

  • 4 Beds
  • 4 Baths
  • 1,627 Sq Ft
  • House for Rent

  201 Parkway St, Winchester, VA 22601

  Freshly Renovated Charmer in Winchester! Welcome to 201 Parkway Street, a freshly updated home in the heart of Winchester! Previously tenant-occupied, this property has been thoughtfully refreshed and is ready for new owners. Recent Updates Include: Fresh interior paint throughout Renovated kitchen and bath Updated fixtures and finishes Clean, move-in ready condition This home offers the perfect

  Cherish Green Coldwell Banker Elite

  201 Parkway St, Winchester, VA 22601
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  /10

  $74,900 Sold Mar 19, 2025

  405 Crescent Dr, Winchester, VA 22601

  • Land
  • 0.19 Acre
  • $394,211 per Acre

  Last Sold Summary

  • 5 Days On Market

  Current Estimated Value $78,831

  Last Listing Agent Matt Kilmer Samson Properties

  405 Crescent Dr, Winchester, VA 22601
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  /13

  Est $362,360 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  2912 Grace St, Winchester, VA 22601

  2912 Grace St, Winchester, VA 22601
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  /34

  $399,000

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

  318 E Piccadilly St, Winchester, VA 22601

  This delightful brick Colonial, perfectly situated in the heart of downtown Winchester, combines classic architecture with modern updates and an unbeatable location close to every downtown amenity, including restaurants, schools, shopping, parks, and major commuter routes. The home welcomes you with a large foyer featuring newly refinished hardwood floors that extend throughout the entire

  Dan Whitacre Colony Realty

  318 E Piccadilly St, Winchester, VA 22601
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  /19

  $1,350 per month

  • 2 Beds
  • 1 Bath
  • 8,508 Sq Ft
  • Condo for Rent

  113 W Boscawen St Unit 3, Winchester, VA 22601

  3rd floor walk-up apartment. Downtown Winchester is this 2 bedroom, 1 bath apartment featuring an abundancy of light with numerous windows, large rooms and hardwood floors. Primary bedroom has direct access to bathroom. Water, sewer and trash pick-up is provided in the monthly rent as is 1 parking space in the Braddock Street Parking Garage. Tenant is responsible for electricity and natural gas

  Barbara Gaul Jim Barb Realty, Inc.

  113 W Boscawen St Unit 3, Winchester, VA 22601
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  /36

  $635,500 Sold Nov 19, 2025

  315 W Leicester St, Winchester, VA 22601

  • 4 Beds
  • 4 Baths
  • 3,100 Sq Ft
  • Built 1923

  Last Sold Summary

  • $205/SF
  • 5 Days On Market

  Last Listing Agent Leigh Phillips MarketPlace REALTY

  315 W Leicester St, Winchester, VA 22601
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  /25

  Est $326,840 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  2817 Papermill Rd, Winchester, VA 22601

  2817 Papermill Rd, Winchester, VA 22601
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  /41

  $485,000 Pending

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

  700 Crow Dr, Winchester, VA 22602

  Motivated Sellers!!!. 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 opportunity for its next owners. The owners

  Deisi Hernandez Fairfax Realty Select

  700 Crow Dr, Winchester, VA 22602
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  /32

  $2,800 per month

  • 2 Beds
  • 2 Baths
  • 1,230 Sq Ft
  • Condo for Rent

  210 E Boscawen St Unit 202, Winchester, VA 22601

  This stunning apartment features 9 south facing windows for maximum natural light, just steps from all of the restaurants, night life and events in Old Town Winchester. The historic Winchester Star building has been renovated for luxury living that includes private parking, a rarity downtown. Two large bedrooms, each with their own en-suite and walk-in closet are set apart by the open space

  Katie Landi Jordan Samson Properties

  210 E Boscawen St Unit 202, Winchester, VA 22601
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  /20

  $450,000 Sold Jul 18, 2025

  111 Yurok Ct, Winchester, VA 22602

  • 3 Beds
  • 2.5 Baths
  • 1,657 Sq Ft
  • Built 2025

  Last Sold Summary

  • $272/SF
  • 69 Days On Market

  Last Listing Agent Brooks Sears D R Horton Realty of Virginia LLC

  111 Yurok Ct, Winchester, VA 22602
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  /19

  Est $328,582 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  2918 S Pleasant Valley Rd, Winchester, VA 22601

  2918 S Pleasant Valley Rd, Winchester, VA 22601
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  /44

  $319,000 Under Contract

  • 1 Bed
  • 1 Bath
  • 1,348 Sq Ft

  242 Footstone Ln, Winchester, VA 22603

  Peaceful Country Retreat on 4.7 Acres – Minutes from WinchesterThis private country home combines solid craftsmanship with serene mountain views. Located on a quiet gravel lane with a road maintenance agreement, the property features a durable stone-and-brick exterior and hardwood floors throughout. Inside, two stone fireplaces—including one in the primary bedroom—add warmth and character.

  Kristina Towns Weichert Realtors - Blue Ribbon

  242 Footstone Ln, Winchester, VA 22603
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  /20

  $3,400 per month

  • 2 Beds
  • 2.5 Baths
  • 1,981 Sq Ft
  • Condo for Rent

  210 E Boscawen St Unit 204, Winchester, VA 22601

  This stunning apartment has nearly 2000 sq ft on one level. Just steps from all of the restaurants, night life and events in Old Town Winchester. The historic Winchester Star building has been renovated for luxury living that includes private parking, a rarity downtown. There are two large bedrooms, each with their own en-suite and walk-in closet, ample living and dining spaces, a separate

  Katie Landi Jordan Samson Properties

  210 E Boscawen St Unit 204, Winchester, VA 22601
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  /35

  $540,000 Sold Jul 01, 2025

  2008 Taylor Grace Ct, Winchester, VA 22601

  • 4 Beds
  • 4 Baths
  • 1,976 Sq Ft
  • Built 2008

  Last Sold Summary

  • $273/SF
  • 26 Days On Market

  Current Estimated Value $547,479

  Last Listing Agent Kent Mull Link Realty Services LLC

  2008 Taylor Grace Ct, Winchester, VA 22601
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  /21

  Est $350,081 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,388 Sq Ft

  2915 S Pleasant Valley Rd, Winchester, VA 22601

  2915 S Pleasant Valley Rd, Winchester, VA 22601
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  /57

  $559,000

  • 4 Beds
  • 3.5 Baths
  • 3,829 Sq Ft

  114 Nassau Dr, Winchester, VA 22602

  4 bed/ 3.5 bath colonial in a prime commuter location just minutes from I-81 and Route 7. Enjoy outdoor living with a fenced backyard, low-maintenance composite decking, brick patio, outdoor fireplace, and a storage shed! The spacious primary suite includes a large walk-in closet and sitting room. The finished basement is ideal for entertaining, featuring a full bath and wet bar. Recent upgrades

  Sheila Pack RE/MAX Roots

  114 Nassau Dr, Winchester, VA 22602
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  /46

  $1,950 per month

  • 2 Beds
  • 2 Baths
  • 1,024 Sq Ft
  • Condo for Rent

  1310 Ramseur Ln, Winchester, VA 22601

  Price Reduced + Owners will consider furnishing for the right tenant!! This 2 bedroom, 2 bath luxury condo has been upgraded with all new plank flooring, new SS appliances in the kitchen, a new counter, upgraded bathrooms, a new HVAC unit, plus a new stack washer/dryer unit. Every room has 9' + ceilings with crown molding and the master bedroom has a nice walk-in closet for all your essentials!

  Cindy Butler Virginia Property Group, Inc.

  1310 Ramseur Ln, Winchester, VA 22601
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  /116

  $537,500 Sold Jan 08, 2026

  510 S Washington St, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 2,874 Sq Ft
  • Built 1920

  Last Sold Summary

  • $187/SF
  • 14 Days On Market

  Last Listing Agent Laurie Webber Century 21 Modern Realty Results

  510 S Washington St, Winchester, VA 22601
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  /23

  Est $267,662 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,252 Sq Ft

  2905 Sorrell Ct, Winchester, VA 22601

  2905 Sorrell Ct, Winchester, VA 22601

Showing Results 481 - 520, Page 13 of 18