Winchester County, VA Homes

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  /52

  $401,290

  Sold Jan 22, 2026

  1814 Blythe Way, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $212/SF
  • 8 Days On Market

  D.R. Horton Abrams Crossing at Meadow Branch

  1814 Blythe Way, Winchester, VA 22601
• 

  

  

  /41

  Est $468,272

  Not Listed For Sale

  610 Quartzite Cir, Winchester, VA 22601

  • 3 Beds
  • 3 Baths
  • 2,002 Sq Ft
  • Built 1998

  610 Quartzite Cir, Winchester, VA 22601

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Teresa Strohmeyer ERA Oakcrest Realty, Inc.
• 

  

  

  /86

  $559,900

  Open House 8/16

  • 2 Beds
  • 2.5 Baths
  • 2,031 Sq Ft

  411-U105 N Loudoun St Unit 105, Winchester, VA 22601

  Experience a rare opportunity to own a piece of Winchester history at The Fort, one of Old Town's most distinctive residential communities. Located just blocks from the vibrant Walking Mall, this beautifully renovated 2-bedroom, 2.5-bath condominium seamlessly blends historic character with modern luxury. Unit 105 features an open-concept floor plan with soaring ceilings, rich architectural

  Jen Richards MarketPlace REALTY

  411-U105 N Loudoun St Unit 105, Winchester, VA 22601
• 

  

  

  /34

  $350,000

  Sold Sep 19, 2025

  216 Monticello Square, Winchester, VA 22602

  • 3 Beds
  • 2.5 Baths
  • 2,436 Sq Ft
  • Built 2010

  Last Sold Summary

  • $144/SF
  • 26 Days On Market

  Current Estimated Value $364,149

  Last Listing Agent LESLIE WEBB Long & Foster Real Estate, Inc.

  216 Monticello Square, Winchester, VA 22602
• 

  

  

  /37

  Est $415,613

  Not Listed For Sale

  2671 Daniel Terrace, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,754 Sq Ft
  • Built 1997

  2671 Daniel Terrace, Winchester, VA 22601

  Last Sold Summary

  • 162 Days On Market

  Last Listing Agent Eric Kronenwetter RE/MAX Roots
• 

  

  /46

  $339,000

  $21K PRICE DROP

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

  307 1/2 E Piccadilly St, Winchester, VA 22601

  Welcome to 307 1/2 E Piccadilly Street, a charming detached home offering comfort, convenience, and character in the heart of Winchester. Ideally located just minutes from Old Town Winchester, the Walking Mall, local restaurants, shopping, parks, and commuter routes, this property places you close to downtown amenities while still offering the privacy and feel of a standalone home. Inside, you’ll

  Nate Crandell HoneyWay

  307 1/2 E Piccadilly St, Winchester, VA 22601
• 

  

  /56

  $297,900

  Sold Dec 04, 2025

  129 E Cork St, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 935 Sq Ft
  • Built 1900

  Last Sold Summary

  • $319/SF
  • 56 Days On Market

  Current Estimated Value $304,765

  Last Listing Agent Melissa Crider Sager Real Estate

  129 E Cork St, Winchester, VA 22601
• 

  

  /58

  Est $576,746

  Not Listed For Sale

  2721 Middle Rd, Winchester, VA 22601

  • 6 Beds
  • 3 Baths
  • 3,452 Sq Ft
  • Built 2002

  2721 Middle Rd, Winchester, VA 22601

  Last Sold Summary

  • 90 Days On Market

  Last Listing Agent Chad Lesman RE/MAX Roots
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  /51

  $364,000

  $15K PRICE DROP

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

  2055 Cidermill Ln, Winchester, VA 22601

  PRICE ADJUSTMENT. Welcome home to this beautifully maintained 3-bedroom, 2-full-bath/2 half bath, end-of-row townhouse! Perfectly situated in a highly desirable, family-friendly neighborhood, step inside to find gleaming hardwood floors and large, sunlit rooms that offer plenty of space to live and entertain. The heart of the home features a spacious kitchen that flows seamlessly onto a private

  Karen O'Hare Colony Realty

  2055 Cidermill Ln, Winchester, VA 22601
• 

  

  /20

  $350,000

  Sold Jul 12, 2026

  105 Boone Ct, Winchester, VA 22602

  • 3 Beds
  • 4 Baths
  • 2,000 Sq Ft
  • Built 2026

  Last Sold Summary

  • 4% Below List Price
  • $175/SF
  • 48 Days On Market

  Last Listing Agent Jimmy Thomas New Home Star Virginia, LLC

  105 Boone Ct, Winchester, VA 22602
• 

  

  /49

  Est $571,383

  Not Listed For Sale

  2717 Middle Rd, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 3,408 Sq Ft
  • Built 2002

  2717 Middle Rd, Winchester, VA 22601

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Ben Barnes Jim Barb Realty Inc.
• 

  

  /6

  $4,500,000

  Under Contract

  • Land
  • 11.43 Acres
  • $393,701 per Acre

  801 Fairmont Ave, Winchester, VA 22601

  Unprecedented Development Opportunity, City of Winchester, 10.34 acres plus 3 SFH fronting Fairmont Ave (additional 1.09 acres). Gateway to downtown Old Town Winchester. Prime location for high density multifamily and mixed use commercial. Public utilities to site. Truly a catalyst development opportunity, located in the fast growing metropolitan area in Virginia. Voted #1 Main Street and Places

  Gillian Greenfield Coldwell Banker Premier

  801 Fairmont Ave, Winchester, VA 22601
• 

  

  /34

  $337,000

  Sold Apr 09, 2026

  19 W Germain St, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,280 Sq Ft
  • Built 2004

  Last Sold Summary

  • $263/SF
  • 18 Days On Market

  Current Estimated Value $335,961

  Last Listing Agent Angela Duncan MarketPlace REALTY

  19 W Germain St, Winchester, VA 22601
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  /52

  Est $535,858

  Not Listed For Sale

  904 W View Ln, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,243 Sq Ft
  • Built 2002

  904 W View Ln, Winchester, VA 22601

  Last Sold Summary

  • 86 Days On Market

  Last Listing Agent Sheila Pack RE/MAX Roots
• 

  

  /19

  $406,190

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,689 Sq Ft

  1813 Sloane St, Winchester, VA 22601

  1813 Sloane St. is an attractive new 3 level townhome with full brick front in Winchester, VA for August move-in. Included Deck for first 3 homebuyers! Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances.

  D.R. Horton Builder

  1813 Sloane St, Winchester, VA 22601
• 

  

  /28

  $380,000

  Sold Dec 18, 2025

  312 Fox Dr, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,105 Sq Ft
  • Built 1959

  Last Sold Summary

  • $344/SF
  • 28 Days On Market

  Current Estimated Value $382,000

  Last Listing Agent Alicia Harris Keller Williams Realty

  312 Fox Dr, Winchester, VA 22601
• 

  

  /3

  Est $535,078

  Not Listed For Sale

  2635 Middle Rd, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,547 Sq Ft
  • Built 2002

  2635 Middle Rd, Winchester, VA 22601

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Stuart Sinclair Coldwell Banker Premier
• 

  

  /29

  $259,900

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  1125 Conway St, Winchester, VA 22601

  Check out this Very Cute Bungalow in Winchester City! It has a Brand NEW Roof, Freshly Painted throughout, NEW kitchen/hall/bath flooring, NEW Stainless Steel Refrigerator, Restored deck, and Lovely Hardwood! Cozy with 2 Bedrooms and 1 Bath. Surely to be perfect for the first time Home Buyer! Great Location close to shopping & restaurants. Great for commuters as well as it's on the East side of

  Jodi Costello ERA Oakcrest Realty, Inc.

  1125 Conway St, Winchester, VA 22601
• 

  

  /19

  $175,000

  Sold May 28, 2026

  253 Opequon Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,266 Sq Ft
  • Built 1956

  Last Sold Summary

  • 7% Below List Price
  • $138/SF
  • 7 Days On Market

  Current Estimated Value $201,558

  Last Listing Agent Marisa Varley ERA Oakcrest Realty, Inc.

  253 Opequon Ave, Winchester, VA 22601
• 

  

  /40

  Est $391,917

  Not Listed For Sale

  2717 Blue Ridge Terrace, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft
  • Built 1959

  2717 Blue Ridge Terrace, Winchester, VA 22601

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Jim Stafford ERA Oakcrest Realty, Inc.
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  /6

  $220,000

  $79K PRICE DROP

  • Studio
  • 1,730 Sq Ft

  384 National Ave, Winchester, VA 22601

  Discover the potential of this 4-bedroom, 2-bath multi-family property offering 1,730 sq ft of living space ona 2,684 sq ft lot. Built in 1930, this property is a great opportunity for investors or buyers looking torenovate and add value. Don't miss your chance to make this income-producing property your next project!

  Derek Greene The Greene Realty Group

  384 National Ave, Winchester, VA 22601
• 

  

  /50

  $450,000

  Sold Oct 06, 2025

  25 E Hart St, Winchester, VA 22601

  • 5 Beds
  • 3 Baths
  • 2,680 Sq Ft
  • Built 1945

  Last Sold Summary

  • $168/SF
  • 15 Days On Market

  Current Estimated Value $465,478

  Last Listing Agent Liz Owings Samson Properties

  25 E Hart St, Winchester, VA 22601
• 

  

  /26

  Est $234,484

  Not Listed For Sale

  22 Jigsaw Place, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,160 Sq Ft
  • Built 1984

  22 Jigsaw Place, Winchester, VA 22601

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Dan Whitacre Colony Realty
• 

  

  /50

  $379,000

  • 3 Beds
  • 3.5 Baths
  • 2,160 Sq Ft

  2104 Stoneleigh Dr, Winchester, VA 22601

  Situated in the charming Orchard Hill subdivision, this delightful twin home offers a perfect blend of comfort and functionality. Built in 1987, this Colonial-style residence boasts a classic brick exterior that exudes warmth and character. With over 2,000 square feet of thoughtfully designed living space, this home is ideal for those seeking a cozy retreat. As you approach the property, you'll

  Kim Hurst MarketPlace REALTY

  2104 Stoneleigh Dr, Winchester, VA 22601
• 

  

  /58

  $535,000

  Sold Apr 15, 2026

  1917 Harvest Dr, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,234 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $239/SF
  • 20 Days On Market

  Current Estimated Value $543,140

  Last Listing Agent Brock Harris Samson Properties

  1917 Harvest Dr, Winchester, VA 22601
• 

  

  /29

  Est $247,246

  Not Listed For Sale

  31 Jigsaw Place, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,160 Sq Ft
  • Built 1985

  31 Jigsaw Place, Winchester, VA 22601

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Susan Raburn Long & Foster Real Estate, Inc.
• 

  

  /34

  $359,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,809 Sq Ft

  328 Longview Ave, Winchester, VA 22601

  Price Reduced $15,000! Highly Motivated Seller! Welcome to this meticulously maintained, 3 bedroom, move-in-ready ranch home located within Winchester City limits. Perfectly situated on a premium, near-half-acre lot (.46 acres) off Papermill Road, this property offers the ultimate blend of city convenience and peaceful privacy with no backyard neighbors. Kitchen and downstairs bathroom to be

  Kelly Bauer Coldwell Banker Premier

  328 Longview Ave, Winchester, VA 22601
• 

  

  /67

  $675,000

  Sold Dec 05, 2025

  316 W Whitlock Ave, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 3,278 Sq Ft
  • Built 1940

  Last Sold Summary

  • $206/SF
  • 4 Days On Market

  Current Estimated Value $700,372

  Last Listing Agent Carla Houchens Pearson Smith Realty, LLC

  316 W Whitlock Ave, Winchester, VA 22601
• 

  

  /42

  Est $345,596

  Not Listed For Sale

  2513 Hillside Terrace, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,823 Sq Ft
  • Built 1967

  2513 Hillside Terrace, Winchester, VA 22601

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Frank Armstrong, IV Colony Realty
• 

  

  /16

  $249,000

  $111K PRICE DROP Pending

  • Studio
  • 1,249 Sq Ft

  45 and 45 1/2 Race St, Winchester, VA 22601

  BACK ON THE MARKET - If you want the "scoop" call me. Property will be vacant soon and updates completed if the buyer request them. Or take this "AS IS" for a big discount. Situated just minutes from the historic Old Town Winchester pedestrian mall and major commuter routes, this is a "set-and-forget" asset in one of the areas strongest rental markets. This is a great starter property for those

  Teri Domanski Your Home Sold Guaranteed Realty - East LLC

  45 and 45 1/2 Race St, Winchester, VA 22601
• 

  

  /18

  $252,500

  Sold May 08, 2026

  2640 Limestone Ct, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,024 Sq Ft
  • Built 1994

  Last Sold Summary

  • 6% Below List Price
  • $247/SF
  • 5 Days On Market

  Current Estimated Value $259,645

  Last Listing Agent Ned Stock Berkshire Hathaway HomeServices PenFed Realty

  2640 Limestone Ct, Winchester, VA 22601
• 

  

  /42

  Est $346,707

  Not Listed For Sale

  2428 Massanutten Terrace, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,676 Sq Ft
  • Built 1956

  2428 Massanutten Terrace, Winchester, VA 22601

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Renee Waymire Samson Properties
• 

  

  /59

  $600,000

  • 3 Beds
  • 1.5 Baths
  • 3,483 Sq Ft

  1311 Handley Ave, Winchester, VA 22601

  Nestled in the charming City of Winchester, this delightful Colonial home, built in 1952, exudes warmth and character. With its classic brick exterior and excellent condition, this residence invites you to experience a blend of traditional elegance and modern comfort. Step inside to discover a thoughtfully designed interior featuring beautiful hardwood floors that flow seamlessly throughout. The

  Kim Hurst MarketPlace REALTY

  1311 Handley Ave, Winchester, VA 22601
• 

  

  /32

  $400,000

  Sold Sep 02, 2025

  423 Crescent Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,548 Sq Ft
  • Built 1998

  Last Sold Summary

  • $258/SF
  • 4 Days On Market

  Current Estimated Value $417,029

  Last Listing Agent Sharon Farinholt Realty ONE Group Old Towne

  423 Crescent Dr, Winchester, VA 22601
• 

  

  /33

  Est $243,259

  Not Listed For Sale

  2518 Hockman Ave, Winchester, VA 22601

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft
  • Built 1954

  2518 Hockman Ave, Winchester, VA 22601

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Jodi Cilley Realty ONE Group Old Towne
• 

  

  /19

  $329,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,576 Sq Ft

  Juniper Plan at Old Town Green, Winchester, VA 22601

  Welcome to Ryan Homes at Old Town Green, experience life in Old Town Winchester with the city's lowest priced garage townhomes, just a short walk to shops, dining and recreation. The Juniper townhome combines all the amenities of single-family living with total convenience. The main level is highlighted by a gourmet kitchen that's open to the living area so you'll never miss a moment. The kitchen

  Ryan Homes Builder

  306 Smalts Cir Unit 41303475, Winchester, VA 22601
• 

  

  /60

  $405,000

  Sold Mar 30, 2026

  139 Biscane Ct, Winchester, VA 22602

  • 3 Beds
  • 3.5 Baths
  • 2,250 Sq Ft
  • Built 2018

  Last Sold Summary

  • 4% Below List Price
  • $180/SF
  • 28 Days On Market

  Current Estimated Value $408,451

  Last Listing Agent Roberto Cardoza Orellana Pearson Smith Realty, LLC

  139 Biscane Ct, Winchester, VA 22602
• 

  

  /76

  Est $484,913

  Not Listed For Sale

  2316 Tower Ave, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,095 Sq Ft
  • Built 2006

  2316 Tower Ave, Winchester, VA 22601

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Brian Yoder Realty ONE Group Old Towne
• 

  

  /23

  $359,900

  Under Contract

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft

  236 Shawnee Ave, Winchester, VA 22601

  Welcome to this beautifully updated brick home offering the perfect blend of charm and modern updates. Major improvements completed in 2021 include a new roof, windows, HVAC system, kitchen cabinets with granite countertops, and a renovated main-level bathroom. A new water heater was installed in 2024. In 2026, a city-permitted addition created a spacious new primary bedroom and bathroom, along

  Jennifer Sacco RE/MAX Roots

  236 Shawnee Ave, Winchester, VA 22601
• 

  

  /36

  $299,900

  Sold Jun 29, 2026

  126 S Euclid Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,086 Sq Ft
  • Built 1989

  Last Sold Summary

  • 6% Below List Price
  • $276/SF
  • 55 Days On Market

  Current Estimated Value $297,924

  Last Listing Agent Matt Kilmer Samson Properties

  126 S Euclid Ave, Winchester, VA 22601

Showing Results 441 - 480, Page 12 of 18