Winchester, VA Homes

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  /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
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  /32

  $1,650 per month

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Townhouse for Rent

  138 Parkside Dr, Winchester, VA 22602

  Call or Text Listing agent Jas Kaur to schedule showing. Tenant occupied. We would need a 2 hour minimum notice for showing. Welcome to 138 Parkside Drive, a charming 3-bedroom, 1.5-bath townhome in a quiet, convenient Winchester neighborhood! This home offers the perfect blend of comfort, style, and location — ideal for families, young professionals, or anyone seeking a peaceful place to call

  Jas Kaur Prime Properties DMV, LLC.

  138 Parkside Dr, Winchester, VA 22602
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  /69

  $419,350 Sold Oct 31, 2025

  • 2,189 Sq Ft
  • $192/SF
  • 90 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1964

  1793 N Hayfield Rd, Winchester, VA 22603

  Charming all-brick ranch home on a spacious .97-acre lot, featuring 3 bedrooms, 2.5 baths, and traditional style throughout. Enjoy a covered front porch, rear deck, living room with fireplace, separate dining room, and eat-in kitchen. Includes a 2-car garage and no HOA. Ideally located—peaceful setting just outside of town, yet only 10 minutes to shopping and Winchester Medical Center, and just

  RoxAnn Grimes RE/MAX Roots

  1793 N Hayfield Rd, Winchester, VA 22603
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  /38

  Est $516,753 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft

  3022 Saratoga Dr, Winchester, VA 22601

  3022 Saratoga Dr, Winchester, VA 22601
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  /43

  $490,000

  • 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. The front porch sets the tone, offering a perfect spot for quiet mornings in the heart of downtown Winchester. Inside, the main level has an easy flow: a bright living room, a dining space ready for gatherings, and a sun-filled enclosed sunroom that naturally becomes a favorite place to slow down. The kitchen has all new

  Leah Marabella Realty ONE Group Old Towne

  227 Miller St, Winchester, VA 22601
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  /7

  $1,895 per month

  • 3 Beds
  • 2 Baths
  • 1,004 Sq Ft
  • Townhouse for Rent

  125 Early Dr, Winchester, VA 22603

  Excellent location for commuters and shopping in the area. This 3 Bedroom 2 Bath home has newer flooring in kitchen and bathrooms, newer paint. updated kitchen and much more. Large backyard mostly fenced in with large storage shed! Pets are case by case, there are certain breed restrictions for dogs, $250 pet deposit per pet and $30 per month additional pet rent. Owner looking for at least 3x

  Jarrett Sowder RE/MAX Roots

  125 Early Dr, Winchester, VA 22603
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  /27

  $289,000 Sold Oct 31, 2025

  • 1,056 Sq Ft
  • $274/SF
  • 3 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1977

  210 Zeiger Dr, Winchester, VA 22602

  Looking for a home just outside the city limits? You are 3 miles from Rt 37 and the hospital. This charming 3-bedroom, 1-bath rancher sits on 1.1 acres at the end of a cul-de-sac, surrounded by trees for extra privacy. Enjoy quiet mornings on the covered front porch or unwind in the evenings on the spacious wrap-around deck. Inside, the home has been tastefully remodeled and is move-in ready.

  Melissa Crider Sager Real Estate

  210 Zeiger Dr, Winchester, VA 22602
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  /5

  Est $436,849 Not Listed For Sale

  329 Longview Ave, Winchester, VA 22601

  329 Longview Ave, Winchester, VA 22601
• 

  

  /61

  $499,000

  • 4 Beds
  • 2.5 Baths
  • 1,959 Sq Ft

  129 Old Wagon Rd, Winchester, VA 22602

  *Sellers are offering $850 towards a home warranty of the buyer's choice* "Outstanding On Old Wagon" This 4 bedroom, 2 1/2 bath colonial style home sits in a cul-de-sac in the highly desirable Pioneer Heights Neighborhood. This home has had a ton of upgrades over the years! Gorgeous, updated custom kitchen with Frigidaire Gallery Appliances, custom built cabinets with pull out shelves, extra

  Matt Kilmer Samson Properties

  129 Old Wagon Rd, Winchester, VA 22602
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  /20

  $2,399 per month

  • 4 Beds
  • 3.5 Baths
  • 2,100 Sq Ft
  • Townhouse for Rent

  115 Boone Ct, Winchester, VA 22602

  Be sure to view the Virtual Tour! This brand-new home offers a complete, modern interior. Featuring 4 bedrooms, 3.5 baths, a 1-car garage, a 10' x 16' composite deck, and a partial fenced yard. The lower level includes a private bedroom with a full bath and walk-out access. The main level boasts luxury vinyl tile flooring throughout, a beautifully open floor plan, and stainless steel appliances.

  Raj Patel Ikon Realty - Ashburn

  115 Boone Ct, Winchester, VA 22602
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  /33

  $370,000 Sold Oct 31, 2025

  • 1,560 Sq Ft
  • $237/SF
  • 25 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1960

  107 Fay St, Winchester, VA 22602

  This beauty will be available mid august or earlier has exceptional renovation and superb location off Rt.11 and great proximity to I-81/Rt.37 corridor. They have done all the big ticket items like installing a new roof, upgrading the baths, BRAND NEW WINDOWS (we all love those!), and considered the most important..newly installed HVAC for keeping your home cool during the summer and warm during

  Dave Spence RE/MAX Roots

  107 Fay St, Winchester, VA 22602
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  /43

  Est $443,171 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,355 Sq Ft

  2817 Broadview St, Winchester, VA 22601

  2817 Broadview St, Winchester, VA 22601
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  /42

  $469,000

  • 4 Beds
  • 1.5 Baths
  • 1,932 Sq Ft

  420 W Cork St, Winchester, VA 22601

  Discover the perfect blend of historic charm and modern convenience at 420 W Cork Street. This captivating four-level brick home offers 4 bedrooms and 1.5 baths, boasting beautiful hardwood floors, gorgeous trim and plenty of space for you and yours. The main level offers a spacious living room, dining room and kitchen. Upstairs you will find 4 sizable bedrooms and a full bath. The top level is a

  Dan Whitacre Colony Realty

  420 W Cork St, Winchester, VA 22601
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  /10

  $1,599 per month

  • 2 Beds
  • 1.5 Baths
  • 900 Sq Ft
  • Townhouse for Rent

  3107 Shawnee Dr Unit 12, Winchester, VA 22601

  Beautifully Renovated Unit Two level townhome*Full size Washer & Dryer*Hardwood like Floors* Huge Brand New Eat-In Kitchen*Ganite counters & Stainless Steel Appliances*Spacious bedrooms*Large closets*Individually controlled HVAC and hot water heater*Plenty of parking*1 mile from great shopping on Valley Avenue, 10 minute from downtown Winchester and 9 minute from Shenandoah University *Photos are

  Steve DuBrueler Coldwell Banker Premier

  3107 Shawnee Dr Unit 12, Winchester, VA 22601
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  /20

  $355,900 Sold Oct 31, 2025

  • 1,208 Sq Ft
  • $295/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  108 Fenwick Ct, Winchester, VA 22602

  Step inside this well-loved one-level home, perfect for starting out or settling in. With 3 comfortable bedrooms and 2 full baths, there’s plenty of space to relax and make your own. The easy single-floor layout makes everyday living a breeze, while the convenient location near Route 7 keeps you close to everything you need. A wonderful opportunity in a welcoming neighborhood. Come see the

  Kathleen Hobbs ERA Oakcrest Realty, Inc.

  108 Fenwick Ct, Winchester, VA 22602
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  /39

  Est $439,546 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,560 Sq Ft

  421 Longview Ave, Winchester, VA 22601

  421 Longview Ave, Winchester, VA 22601
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  /47

  $467,000

  • 4 Beds
  • 3 Baths
  • 2,654 Sq Ft

  219 Milam Dr, Winchester, VA 22602

  Welcome to 219 Milam Drive, a spacious and updated all-brick rancher tucked in a quiet neighborhood just minutes from downtown Winchester, Route 7, and I-81. This four-bedroom, three-bath home offers over 2,700 square feet of finished living space, including a partially finished basement and additional storage or hobby rooms to suit your needs. Inside, you’ll find warm hardwood flooring, modern

  Kira Grubb Realty ONE Group Old Towne

  219 Milam Dr, Winchester, VA 22602
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  /10

  $1,950 per month

  • 3 Beds
  • 2.5 Baths
  • 1,560 Sq Ft
  • House for Rent

  511 National Ave, Winchester, VA 22601

  elcome to this spacious and well-maintained 2-story home, perfect for families or professionals! Located just minutes from downtown Winchester, this home offers the ideal balance of comfort and convenience.

  Meridee Powars Link Realty Services LLC

  511 National Ave, Winchester, VA 22601
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  /27

  $324,000 Sold Oct 31, 2025

  • 1,119 Sq Ft
  • $290/SF
  • 20 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  414 Raccoon Dr, Winchester, VA 22602

  Affordable Gem! Better than new home just over 1 year old with added wood rear fence $12,000 and shed.$5,000 Level flat lot (over 1/2 acre) close to entrance (98% paved roads to home). Covered front porch (trex). Open floor plan with LVP flooring (no carpeting). Tiled baths and wooden shelves/organizer walk in closet.

  Jim Thomson Realty ONE Group Old Towne

  414 Raccoon Dr, Winchester, VA 22602
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  /38

  Est $451,971 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  425 Longview Ave, Winchester, VA 22601

  425 Longview Ave, Winchester, VA 22601
• 

  

  /94

  $499,900

  • 4 Beds
  • 3.5 Baths
  • 2,976 Sq Ft

  2812 Ridgetop Ct, Winchester, VA 22601

  HUGE PRICE IMPROVEMENT! Welcome to this beautiful "picture perfect" brick front 4-bedroom, 3.5-bath home in the desirable Rolling Hills community of Winchester, VA. Perfectly located at the end of a cul-de-sac in an established (and sought after) neighborhood, this one-owner property has been meticulously maintained and is ready for its next chapter.Inside, you’ll find a spacious and inviting

  Sara Duncan RE/MAX Distinctive Real Estate

  2812 Ridgetop Ct, Winchester, VA 22601
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  /45

  $1,850 per month

  • 2 Beds
  • 1 Bath
  • 997 Sq Ft
  • House for Rent

  108 Martin Dr, Winchester, VA 22602

  Charming brick rambler on corner lot. Situated on a quiet street but just a few minutes to route 7 and I-81, this rental offers the perfect commuting location. The open floor features large windows that fill the space with light. An eat-in kitchen offers plenty of cabinetry and room for casual dining. Enjoy the ease of indoor laundry with direct access to the yard. The home includes 2 spacious

  Heloisa Amar Samson Properties

  108 Martin Dr, Winchester, VA 22602
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  /31

  $305,000 Sold Oct 31, 2025

  • 1,690 Sq Ft
  • $180/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1998

  106 Sutton Ct, Winchester, VA 22601

  Looking for convenience, comfort, and updates already in place? This delightful townhouse is located in Winchester in the Huntington Meadows neighborhood, just minutes from shopping, dining, and all the amenities you need. Step inside to find a welcoming living space featuring newer flooring in the living room, new ceiling fans and a bright, functional kitchen with a new floor, updated

  Sharon Farinholt Realty ONE Group Old Towne

  106 Sutton Ct, Winchester, VA 22601
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  /33

  Est $418,135 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,366 Sq Ft

  417 Circle Dr, Winchester, VA 22601

  417 Circle Dr, Winchester, VA 22601
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  /42

  $479,900

  • 3 Beds
  • 2.5 Baths
  • 1,976 Sq Ft

  703 National Ave, Winchester, VA 22601

  Fully renovated in 2025, this 3-bedroom, 2.5-bath home is ideally located within Winchester city limits—just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment, as well as Jim Barnett Park for outdoor recreation. Thoughtful updates and fresh landscaping enhance its curb appeal. Inside, you’ll find brand-new bathrooms with updated lighting, vanities,

  Jennifer Sacco RE/MAX Roots

  703 National Ave, Winchester, VA 22601
• 

  

  /25

  $1,250 per month

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft
  • Condo for Rent

  24 Jackson Ave Unit 2, Winchester, VA 22601

  AFFORDABLE AND CHARMING. Short drive to downtown, Winchester Medical Center, I-81 and Rt. 37. Convenient to shopping and services. Spacious 2-bedroom upstairs apartment with off-street parking in the rear, front porch and a private 16x12 rear deck. Eat-in kitchen with refrigerator and oven/range. No smoking. No pets. Landlord prefers credit scores of 680 or higher, minimum monthly income of 3x

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  24 Jackson Ave Unit 2, Winchester, VA 22601
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  /22

  $760,000 Sold Oct 31, 2025

  • 2,786 Sq Ft
  • $273/SF
  • 6 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1988

  505 Glendobbin Rd, Winchester, VA 22603

  Set on a bucolic 5.5-acre lot in the coveted area of Apple Pie Ridge, this beautifully renovated 4-bedroom, 2.5-bath Colonial blends a classic floor plan (2,750 sq.ft.) with new on-trend updates.Enter to gorgeous new hardwood floors throughout the main level. A spacious, light-filled living room with a wood-burning fireplace flows into the kitchen, which boasts new cabinetry, countertops, and

  Rachael Duvall TTR Sotheby's International Realty

  505 Glendobbin Rd, Winchester, VA 22603
• 

  

  /35

  Est $354,332 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,508 Sq Ft

  416 Superior Ave, Winchester, VA 22601

  416 Superior Ave, Winchester, VA 22601
• 

  

  /49

  $489,970

  • 5 Beds
  • 3 Baths
  • 3,116 Sq Ft

  110 Carter Place, Winchester, VA 22602

  Contract fell through! Interest rates have gone down! Extensive Renovations: The home has been fully renovated in 2025, including updates to kitchen, bathrooms, flooring, and fresh paint throughout. Designed to accommodate two families comfortably, featuring large rooms that are flooded with natural light like the entire house. The lower level is equipped with wheelchair-accessible features,

  Rodrigo Cruz Long & Foster Real Estate, Inc.

  110 Carter Place, Winchester, VA 22602
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  /6

  $2,000 per month

  • 3 Beds
  • 2.5 Baths
  • 1,554 Sq Ft
  • House for Rent

  1958 Cidermill Ln, Winchester, VA 22601

  Three bedroom 2.5 bath duplex in Orchard Hill close to end of Cidermill Lane, carpet/vinyl floor covering, stove, refrigerator, dishwasher, microwave in galley style kitchen, corner natural gas fireplace, large laundry room with washer/dryer hookup, one car garage, deck off dining room with landscaped back yard, sitting area at back of yard Application in one person's name, credit score of 650+,

  James Golladay Crum Realty, Inc.

  1958 Cidermill Ln, Winchester, VA 22601
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  /81

  $585,000 Sold Oct 30, 2025

  • 2,400 Sq Ft
  • $244/SF
  • 12 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2003

  432 Lilys Way, Winchester, VA 22602

  Spacious 2 story home with an in-ground pool and low maintenance yard on the East side of Winchester! A 4 bedroom home with 2.5 baths all on the main level. Large family room with lots of natural light and a gas fireplace. Separate dining room for entertaining. You will love the layout of this home home Updated kitchen with granite counters, tile backsplash. and stainless steel updated

  Diana Geremia Long & Foster Real Estate, Inc.

  432 Lilys Way, Winchester, VA 22602
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  /36

  Est $514,812 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,600 Sq Ft

  2816 Baldwin St, Winchester, VA 22601

  2816 Baldwin St, Winchester, VA 22601
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  /32

  $474,500

  • 4 Beds
  • 4 Baths
  • 1,627 Sq Ft

  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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  /37

  $2,200 per month

  • 3 Beds
  • 2.5 Baths
  • 1,220 Sq Ft
  • Townhouse for Rent

  109 Lance Way, Winchester, VA 22603

  Welcome home to 109 Lance Way in Winchester, VA! This beautiful 3-bedroom, 2.5-bath home offers the perfect blend of comfort and convenience. Ideally located near Old Town Winchester, shopping, dining, and major commuter routes, you’ll love the easy access to everything you need to include grocery and restaurant just down the road. Enjoy a bright, open layout with spacious living areas, a deck

  Gloria Sheridan Keller Williams Realty

  109 Lance Way, Winchester, VA 22603
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  /53

  $665,000 Sold Oct 30, 2025

  • 2,981 Sq Ft
  • $223/SF
  • 47 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2024

  124 Triangle Ct, Winchester, VA 22602

  Don’t miss your chance to own this gorgeous home in Abrams Pointe! Built in 2024, this colonial home is nearly new and features 4 bedrooms, 3.5 bathrooms, a 3-car garage, a private study, and a fenced yard, all on a .28 acre premium lot. The covered front porch will be sure to impress you upon arriving, as well as the grand two-story foyer with an abundance of windows and natural lighting. Just

  Crystal Dudurich ERA Liberty Realty

  124 Triangle Ct, Winchester, VA 22602
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  /52

  Est $413,393 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,702 Sq Ft

  209 W Cedarmeade Ave, Winchester, VA 22601

  209 W Cedarmeade Ave, Winchester, VA 22601
• 

  

  /28

  $475,000

  • 6 Beds
  • 3 Baths
  • 2,736 Sq Ft

  386 Round Hill Rd, Winchester, VA 22602

  *** ATTENTION INVESTORS - OFFERED AT A NEW PRICE!! *** You will want to check out this fantastic opportunity - with a history of POSITIVE CASH FLOW these two ADJACENT PROPERTIES on a combined total of 1.91-acres in Winchester (just minutes from Valley Health Campus, shopping, restaurants and Rt. 37) may be what you are looking for! *** These two parcels are to be sold TOGETHER; they are not

  Bridget Aikens Colony Realty

  386 Round Hill Rd, Winchester, VA 22602
• 

  

  /11

  $2,199 per month

  • 3 Beds
  • 2.5 Baths
  • 2,180 Sq Ft
  • Townhouse for Rent

  115 Stribling Way, Winchester, VA 22602

  3 YEAR YOUNG IN FREEDOM MANOR AVAILABLE FOR RENT*GRANITECOUNTER TOPS*STAINLESS STEEL APPLIANCES*. IDEALLY LOCATED BETWEEN 7 AND 50, EAST OF 81 - THIS 3 LEVEL GARAGE UNIT W/EXTENSIONS IS READY FOR THE NICE TENANTS. MAIN LEVEL FEATURES OPEN CONCEPT LAYOUT WITH SPACIOUS LIVING SPACE, POWDER ROOM, KITCHEN WITH LARGE ISLAND AND BREAKFAST NOOK, . UPPER LEVEL HAS PRIMARY BEDROOM WITH ENSUITE BATH AND

  Rajesh Cheruku Ikon Realty - Ashburn

  115 Stribling Way, Winchester, VA 22602
• 

  

  /35

  $540,000 Sold Oct 30, 2025

  • 2,233 Sq Ft
  • $242/SF
  • 44 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2005

  143 Harvest Ridge Dr, Winchester, VA 22601

  Welcome to 143 Harvest Ridge Drive located in the highly desirable VILLAGE AT HARVEST RIDGE, a 55+ community in Winchester, Virginia. The address says Winchester, but the home is located in Frederick County, just outside of the Winchester City limits making it convenient for shopping, dining out, and medical appointments. This home is elegant, well designed, and meticulously maintained. The

  Elizabeth Page Boxwell MarketPlace REALTY

  143 Harvest Ridge Dr, Winchester, VA 22601
• 

  

  /53

  Est $478,694 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,518 Sq Ft

  102 Russelcroft Rd, Winchester, VA 22601

  102 Russelcroft Rd, Winchester, VA 22601

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