37,094

Winchester, VA Homes

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  • /5

    $89,000

    • Land
    • 40,075 Sq Ft
    • $96,739 per Acre

    Lot 14A Timber Ridge Trail, Winchester, VA 22602

    Enjoy Stunning Sunsets and Endless Sky on This Nearly One-Acre Lot! Imagine unwinding every evening with spectacular sunsets glowing across the valley—the back of this beautiful lot faces northwest, perfect for soaking in nature’s spectacular evening show. Located just 30 minutes from downtown Winchester, this serene oasis offers the ideal blend of peaceful country living and convenient city

    Kristin Crosby Samson Properties

    Lot 14A Timber Ridge Trail, Winchester, VA 22602
  • /40

    $2,300 Per Month

    • 4 Beds
    • 3.5 Baths
    • 1,889 Sq Ft
    • Townhouse for Rent

    188 Sioux Loop, Winchester, VA 22602

    STOP SCROLLING - THIS IS THE ONE!! Welcome to your next DREAM HOME in the highly sought-after Retreat at Winding Creek! This BRAND-NEW 2026-built 4-bedroom, 3.5-bath townhome offers nearly 1,900 sq ft of gorgeous, move-in-ready living space across three beautifully designed levels. Picture yourself cooking in a chef-worthy kitchen with a massive center island, sleek stainless

    Shakha Agrawal Pearson Smith Realty, LLC

    188 Sioux Loop, Winchester, VA 22602
  • /22

    $398,990

    Sold Apr 01, 2026

    2420 Swansong Place, Winchester, VA 22603

    • 4 Beds
    • 3.5 Baths
    • 2,094 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $191/SF
    • 23 Days On Market

    Brookfield Residential Snowden Bridge - Townhome Collection

    2420 Swansong Place, Winchester, VA 22603
    • /54

      Not Listed For Sale

      102 Nootka Way, Winchester, VA 22602

      • 3 Beds
      • 2.5 Baths
      • 1,500 Sq Ft
      • Built 2025
      102 Nootka Way, Winchester, VA 22602

      Last Sold Summary

      • 15 Days On Market

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

  • /25

    $1,315,000

    • Land
    • 2.23 Acres
    • $589,686 per Acre

    0 N Frederick Pike Unit VAFV2042578, Winchester, VA 22603

    Opportunities like this are becoming increasingly difficult to find within the growing Winchester market. Strategically positioned along the Rt. 522 corridor, this 2.23-acre commercial property offers the ideal combination of visibility, accessibility, flexibility, and future potential. Surrounded by established medical facilities, national businesses, residential communities, and expanding

    Team Dickinson Century 21 Redwood Realty

    0 N Frederick Pike Unit VAFV2042578, Winchester, VA 22603
  • /26

    $2,250 Per Month

    • 3 Beds
    • 2 Baths
    • 1,725 Sq Ft
    • House for Rent

    2141 Valley Ave, Winchester, VA 22601

    Renovated cape cod on Valley Avenue with 3 bedrooms and 2 full baths (tiled showers), open kitchen living concept, fresh new paint, Luxury Vinyl Plank flooring throughout, HVAC, and large parking area with side yard. Brand new Quartz countertops, cabinets, and appliances. Rentspree application required and pets case by case but no more than two animals will be accepted. Owner/Agent

    Dave Spence RE/MAX Roots

    2141 Valley Ave, Winchester, VA 22601
  • /74

    $460,000

    Sold May 15, 2026

    320 Shawnee Trail, Winchester, VA 22602

    • 3 Beds
    • 3 Baths
    • 2,860 Sq Ft
    • Built 1999

    Last Sold Summary

    • 2% Above List Price
    • $161/SF
    • 10 Days On Market

    Current Estimated Value $453,630

    Last Listing Agent Stacey Mullins ERA Oakcrest Realty, Inc.

    320 Shawnee Trail, Winchester, VA 22602
    • /5

      Not Listed For Sale

      0 Bobcat Trail Unit 2500019, Winchester, VA 22602

      0 Bobcat Trail Unit 2500019, Winchester, VA 22602

      Last Sold Summary

      • 58 Days On Market

      Last Listing Agent Andy Austin Double A Auction & Realty

  • /79

    $899,990

    Open Sat 3PM - 5PM $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,803 Sq Ft

    300 Tavistock Dr, Winchester, VA 22602

    Discover the perfect blend of space, privacy and convenience this expansive 3500 sq ft plus ranch home situated on 7.12 beautiful acres. Located just 10 mins from shopping, medical facilities and highway access, this property offers peaceful country living. Inside, you'll spacious one-level living with plenty of room to spread out. A large unfinished bonus space on the second floor provides

    Pamela Baber Coldwell Banker Premier

    300 Tavistock Dr, Winchester, VA 22602
  • /12

    $2,100 Per Month

    • 3 Beds
    • 1 Bath
    • 2,781 Sq Ft
    • Condo for Rent

    107 Morgan St, Winchester, VA 22601

    3 bedroom 1 bath apartment on the 2nd and 3rd floors. Spacious with lots of light. Great location. No pets.Tenant is responsible for all utilities.This unit includes the detached 1 car garage and use of the driveway. In addition on street parking is available.

    Kenny Ritenour Samson Properties

    107 Morgan St, Winchester, VA 22601
  • /65

    $800,000

    Sold Mar 31, 2026

    2411 Hunting Ridge Rd, Winchester, VA 22603

    • 4 Beds
    • 3.5 Baths
    • 5,040 Sq Ft
    • Built 2005

    Last Sold Summary

    • 3% Below List Price
    • $159/SF
    • 151 Days On Market

    Current Estimated Value $795,856

    Last Listing Agent Amanda White Nova Home Hunters Realty

    2411 Hunting Ridge Rd, Winchester, VA 22603
    • /12

      Not Listed For Sale

      Lot 21 Cardinal Dr, Winchester, VA 22602

      Lot 21 Cardinal Dr, Winchester, VA 22602

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Kristin Crosby Samson Properties

  • /89

    $1,100,000

    $150K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,188 Sq Ft

    1015 Redbud Rd, Winchester, VA 22603

    Set on over 10private acres in the quiet Locust Level Estates community, this beautifully designed 4-bedroom, 4.5-bath ranch-style home offers the rare combination of peaceful country living without feeling isolated from everyday conveniences. Thoughtfully designed for comfortable main-level living, the home blends manageable luxury, functionality, and scenic countryside beauty, creating an ideal

    Ryan Rice Keller Williams Capital Properties

    1015 Redbud Rd, Winchester, VA 22603
  • /21

    $1,650 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,120 Sq Ft
    • Townhouse for Rent

    255 Waterford Ln, Winchester, VA 22602

    Welcome home to this charming and well-maintained 2-bedroom, 1.5-bath townhouse, offering the perfect combination of comfort, convenience, and low-maintenance living. Nestled in a quiet, family-friendly neighborhood, this inviting home is move-in ready. Step inside to a spacious living room featuring beautiful hardwood floors that lead to a bright, eat-in kitchen with ceramic tile flooring and

    Vilma (Liliana) Uriarte Long & Foster Real Estate, Inc.

    255 Waterford Ln, Winchester, VA 22602
  • /2

    $575,000

    Sold Jul 01, 2026

    447 Plow Run Ln, Winchester, VA 22602

    • 3 Beds
    • 2 Baths
    • 1,949 Sq Ft
    • Built 2019

    Last Sold Summary

    • 1% Above List Price
    • $295/SF
    • 12 Days On Market

    Current Estimated Value $568,817

    Last Listing Agent Denise Bishop Long & Foster Real Estate, Inc.

    447 Plow Run Ln, Winchester, VA 22602
    • /3

      Not Listed For Sale

      704 Pheasant Dr, Winchester, VA 22602

      704 Pheasant Dr, Winchester, VA 22602

      Last Sold Summary

      • 80 Days On Market

      Last Listing Agent Kimberly Schroeder Long & Foster Real Estate, Inc.

  • /24

    $674,900

    • 4 Beds
    • 3 Baths
    • 2,967 Sq Ft

    1611 Apple Pie Ridge Rd, Winchester, VA 22603

    This custom-built beautiful home has only been lived in by one family since being built. It offers 4 bedrooms and 3 full baths. They have kept this home in excellent condition. Upgraded kitchen cabinets and all appliances will convey with this sale. Washer and Dryer located on main level will also convey with this sale. The finished basement offers an added bonus for any family. Has 2.3 acres

    Leo Smith CENTURY 21 New Millennium

    1611 Apple Pie Ridge Rd, Winchester, VA 22603
  • /18

    $1,625 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    129 Brookland Terrace Unit 10, Winchester, VA 22602

    Welcome home to this spacious 2-bedroom, 2-bathroom condo located in the desirable Park Place community. Conveniently situated near Route 7 and I-81, you'll enjoy easy access to shopping, restaurants, pharmacies, and everyday conveniences, with a community playground located just across the parking lot. Inside, you'll find an open and inviting floor plan featuring vaulted ceilings, skylights that

    Ashley Crabill Coldwell Banker Premier

    129 Brookland Terrace Unit 10, Winchester, VA 22602
  • /57

    $648,900

    Sold Jun 12, 2026

    930 Wayne Dr, Winchester, VA 22601

    • 4 Beds
    • 3.5 Baths
    • 4,188 Sq Ft
    • Built 2003

    Last Sold Summary

    • 1% Above List Price
    • $155/SF
    • 24 Days On Market

    Current Estimated Value $649,501

    Last Listing Agent Elizabeth Flood Keller Williams Realty

    930 Wayne Dr, Winchester, VA 22601
    • /28

      Not Listed For Sale

      303 Summerfield Dr, Winchester, VA 22602

      • 4 Beds
      • 3.5 Baths
      • 3,200 Sq Ft
      • Built 2025
      303 Summerfield Dr, Winchester, VA 22602

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent JP Carr Merrifield Realty, LLC

  • /48

    $580,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 3,328 Sq Ft

    608 Bellview Ave, Winchester, VA 22601

    Open House Sunday, July 19th from 12pm - 2pm! Welcome home to this spacious single-family home in the sought-after Williamsburg Heights community! This great home, located in the Winchester City limits, features 4 bedrooms, 2.5 bathrooms, 1 car detached garage, 3200 finished square feet on 2 levels, a huge deck, brick patio and vinyl fenced backyard.Recent updates include the kitchen with

    Kevin LaRue Century 21 Redwood Realty

    608 Bellview Ave, Winchester, VA 22601
  • /18

    $2,199 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,504 Sq Ft
    • Townhouse for Rent

    413 Tevis St, Winchester, VA 22601

    NEWER UNIT HAS AN OPEN KITCHEN WITH GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, LED LIGHTING AND 1 USB/OUTLET COMBO IN KITCHEN. WHOLE HOUSE WINDOW TREATMENTS INCLUDED, WASHER/DRYER AND PROGRAMABLE THERMOSTAT. RENT INCLUDES EXTERIOR LAWN CARE AND SNOW REMOVAL. WASHER AND DRYER INCLUDED. VERY NEAR TO 1-81 AND ALL SHOPPING

    Rajesh Cheruku FAB Realty LLC

    413 Tevis St, Winchester, VA 22601
  • /2

    $585,000

    Sold May 04, 2026

    328 Sheridan Ave, Winchester, VA 22601

    • 4 Beds
    • 2.5 Baths
    • 2,909 Sq Ft
    • Built 1958

    Last Sold Summary

    • $201/SF
    • 3 Days On Market

    Current Estimated Value $580,750

    Last Listing Agent Mary Casselano Dream Real Estate

    328 Sheridan Ave, Winchester, VA 22601
    • /10

      Not Listed For Sale

      113 Pawn Ct, Winchester, VA 22602

      • 3 Beds
      • 2 Baths
      • 2,850 Sq Ft
      • Built 2025
      113 Pawn Ct, Winchester, VA 22602

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Jay Day LPT Realty, LLC

  • /33

    $230,000

    Under Contract
    • 3 Beds
    • 1 Bath
    • 924 Sq Ft

    554 N Kent St, Winchester, VA 22601

    Conveniently located in the heart of the City of Winchester, this charming home is just a short walk to the shops, restaurants, entertainment, and events of historic Old Town Winchester. Offering 3 bedrooms and 1 full bath, the home features an eat-in kitchen, a fenced backyard, and a storage shed for added convenience. Ready for your personal touches, this property offers an excellent

    Leah Clowser RE/MAX Roots

    554 N Kent St, Winchester, VA 22601
  • /25

    $2,400 Per Month

    • 4 Beds
    • 3.5 Baths
    • Townhouse for Rent

    241 Monteith Dr, Winchester, VA 22601

    Welcome to this stunning new construction 3-level townhome offering 4 bedrooms, 3.5 baths, and a 1-car garage with extra storage space, perfectly situated on a premium homesite backing to mature trees for added privacy and peaceful views. The entry level features a versatile fourth bedroom with a private full bath and walk-in shower, making it ideal as a guest suite, home office, or recreation

    Denise Finley Pearson Smith Realty, LLC

    241 Monteith Dr, Winchester, VA 22601
  • /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 $708,301

    Last Listing Agent Amber Jenkins Century 21 Redwood Realty

    251 Heather Hill Ln, Winchester, VA 22603
    • /13

      Not Listed For Sale

      117 Pawn Ct, Winchester, VA 22602

      • 4 Beds
      • 4.5 Baths
      • 4,450 Sq Ft
      • Built 2025
      117 Pawn Ct, Winchester, VA 22602

      Last Sold Summary

      • 74 Days On Market

      Last Listing Agent Jay Day LPT Realty, LLC

  • /65

    $374,990

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 1,752 Sq Ft

    115 Castaway Place, Winchester, VA 22603

    Live more, maintain less.This move‐in ready villa in Hiatt Pointe at Snowden Bridge is designed for easy, low‐maintenance living in a gated 55+ community built around connection and convenience.Enjoy true main‐level living with a peaceful primary suite, laundry on the first floor, and a one‐car garage for effortless daily routines. Snow removal, trash, and recycling are all included—so

    Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

    115 Castaway Place, Winchester, VA 22603
  • /31

    $2,100 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,674 Sq Ft
    • Townhouse for Rent

    1957 Cidermill Ln, Winchester, VA 22601

    "Come On Down To Cidermill" Beautiful 3 bedroom, 2 1/2 bath duplex style townhome at end of street! All 3 bedrooms on upper level. Spacious family room, large eat in kitchen and back deck with stairs down to the yard. Large laundry room on basement level. One car garage and spacious driveway. Conveniently located in Winchester City. No pets and no smoking. Home has just been remolded with the

    Matt Kilmer Samson Properties

    1957 Cidermill Ln, Winchester, VA 22601
  • /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

    Current Estimated Value $589,981

    Last Listing Agent Gillian Greenfield Coldwell Banker Premier

    230 W Boscawen St, Winchester, VA 22601
    • /15

      Not Listed For Sale

      3138 Eton Place, Winchester, VA 22601

      • 3 Beds
      • 2.5 Baths
      • 1,916 Sq Ft
      • Built 2024
      3138 Eton Place, Winchester, VA 22601

      Last Sold Summary

      • 220 Days On Market

      Last Listing Agent Brittany Newman DRB Group Realty, LLC

  • /47

    $349,990

    $40K PRICE DROP Pending
    • 3 Beds
    • 1 Bath
    • 2,102 Sq Ft

    519 Fairmont Ave, Winchester, VA 22601

    Expect a long love affair with this home.Some homes feel like they were built with patience, pride, and a sense of permanence—and this historic Winchester beauty has that feeling the moment you step inside. Set near Old Town Winchester and positioned right next to the approved Cider Hill Neighborhood Design District, it offers something rare: preserved historic character today, with a

    Hannah Won Samson Properties

    519 Fairmont Ave, Winchester, VA 22601
  • /2

    $1,595 Per Month

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Townhouse for Rent

    346 Gray Ave, Winchester, VA 22601

    This charming Colonial townhouse, built in 1930 and set for a major renovation in 2026, offers a unique blend of historic character and modern comfort. With three spacious bedrooms and a full bathroom, this home is perfect for those seeking a cozy retreat. The inviting hardwood and luxury vinyl plank flooring throughout enhances the warmth of the space. Located in a vibrant neighborhood, you'll

    Brandon Pifer Pifer Realty, LLC

    346 Gray Ave, Winchester, VA 22601
  • /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

    Current Estimated Value $345,224

    Last Listing Agent Anselm Tamasang Weichert Realtors - Blue Ribbon

    966 Woodstock Ln, Winchester, VA 22601
    • /32

      Not Listed For Sale

      570 Glaize Orchard Rd, Winchester, VA 22603

      • 3 Beds
      • 3 Baths
      • 1,850 Sq Ft
      • Built 2025
      570 Glaize Orchard Rd, Winchester, VA 22603

      Last Sold Summary

      • 187 Days On Market

      Last Listing Agent Jim Thomson Realty ONE Group Old Towne

  • /30

    $389,900

    $9K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,909 Sq Ft

    527 Grouse Dr, Winchester, VA 22602

    Welcome to 527 Grouse Drive—almost new construction offering the perfect blend of modern finishes, functional living space, and peaceful mountain surroundings. This beautifully updated split foyer home features 3 bedrooms, 2.5 bathrooms, and over 1,900 finished square feet situated on a spacious lot.Open-concept layout filled with natural light, fresh paint throughout, updated light fixtures,

    Amanda Magana RE/MAX Roots

    527 Grouse Dr, Winchester, VA 22602
  • /8

    $1,595 Per Month

    • 3 Beds
    • 1 Bath
    • 900 Sq Ft
    • Townhouse for Rent

    0 S Cameron St, Winchester, VA 22601

    This charming Colonial townhouse, built in 1930 and set for a major renovation in 2024, offers a unique blend of historic character and modern comfort. With three spacious bedrooms and a full bathroom, this home is perfect for those seeking a cozy retreat. The end-of-row design provides added privacy and natural light, enhancing the inviting atmosphere. Located in a vibrant neighborhood, you'll

    Brandon Pifer Pifer Realty, LLC

    0 S Cameron St, Winchester, VA 22601
  • /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

    Current Estimated Value $670,618

    Last Listing Agent Leigh Phillips MarketPlace REALTY

    315 W Leicester St, Winchester, VA 22601
    • /63

      Not Listed For Sale

      327 Russellcroft Rd, Winchester, VA 22601

      • 3 Beds
      • 3 Baths
      • 3,873 Sq Ft
      • Built 1968
      327 Russellcroft Rd, Winchester, VA 22601

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Matt Kilmer Samson Properties

Showing Results 481 - 520, Page 13 of 18

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