Winchester, VA Homes

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  /15

  $509,990 New Construction

  • 3 Beds
  • 2 Baths
  • 2,050 Sq Ft

  107 Sunflower Way, Winchester, VA 22603

  Welcome to your ideal one-level villa- the Hemingway! This thoughtfully designed home centers around a spacious kitchen, perfect for both daily life and entertaining guests. The main level offers two generous bedrooms, including a primary suite featuring a large walk-in closet and a private en suite bathroom for ultimate comfort. Convenience is key with a laundry room located just off the 2-car

  Brookfield Residential Builder

  107 Sunflower Way, Winchester, VA 22603
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  /15

  $1,600 per month

  • 3 Beds
  • 1,040 Sq Ft
  • House for Rent

  209 Shenandoah Ave, Winchester, VA 22601

  Good Credit Score 650+/ Copy Credit Report must be provided by tenant. $40 per adult application processing fee.Deposit $1600 required.NO-PETS / NO SMOKERS Allowed. Lawn Care Included. Nice one floor ranch home 3 bedrooms and 1 bath walk-in shower fully remodeled. New heatpump installed 2025

  Barbara Gaul Jim Barb Realty, Inc.

  209 Shenandoah Ave, Winchester, VA 22601
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  /72

  $700,000 Sold Oct 29, 2025

  292 Green Spring Rd, Winchester, VA 22603

  • 4 Beds
  • 4.5 Baths
  • 4,320 Sq Ft
  • Built 1990

  Last Sold Summary

  • $162/SF
  • 87 Days On Market

  Current Estimated Value $741,138

  Last Listing Agent Katie Landi Jordan Samson Properties

  292 Green Spring Rd, Winchester, VA 22603
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  /40

  Est $383,088 Not Listed For Sale

  112 Copeley Cir, Winchester, VA 22602

  • 3 Beds
  • 2.5 Baths
  • 1,724 Sq Ft
  • Built 2022

  112 Copeley Cir, Winchester, VA 22602

  Last Sold Summary

  • 2% Above List Price
  • $218/SF
  • 17 Days On Market

  Last Sold Price $375,000

  Last Listing Agent Leah Clowser RE/MAX
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  /12

  $16,000

  • Land
  • 0.26 Acre
  • $61,538 per Acre

  Lot 23 Panther Dr, Winchester, VA 22602

  Nestled in the tranquil community of Wilde Acres, this partially cleared, .26 acre lot offers endless potential for your dream home. Enjoy the serenity of nature while still being just a short drive from local amenities, the perfect balance of peace and convenience. Whether you’re looking for a weekend retreat or a full-time residence, this property provides the ideal setting to make your vision

  Amanda Toothman Dandridge Realty Group, LLC

  Lot 23 Panther Dr, Winchester, VA 22602
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  /39

  $2,500 per month

  • 4 Beds
  • 3.5 Baths
  • 1,920 Sq Ft
  • Townhouse for Rent

  1829 Harvest Dr, Winchester, VA 22601

  Brand new, pristine townhome, spacious end unit. Security system, featuring remote keyless entry and a video doorbell. Kitchen with stainless appliances and large island, opens to dining deck. Conveniently located with easy access to schools, hospital, shopping, services and major commuting thoroughfares. Landscaping maintenance and snow removal provided, city trash pick-up. Landlord requires a

  Dallas Croft Samson Properties

  1829 Harvest Dr, Winchester, VA 22601
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  /2

  $800,000 Sold Oct 29, 2025

  601 Fall Run Ln, Winchester, VA 22602

  • 3 Beds
  • 2 Baths
  • 2,175 Sq Ft
  • Built 2022

  Last Sold Summary

  • $368/SF
  • 75 Days On Market

  Current Estimated Value $802,047

  Last Listing Agent Theo Theologis Slones Real Estate

  601 Fall Run Ln, Winchester, VA 22602
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  /14

  Not Listed For Sale

  238 Lehigh Dr Unit HARLOW II 002, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 4,034 Sq Ft
  • Built 2024

  238 Lehigh Dr Unit HARLOW II 002, Winchester, VA 22602

  Last Sold Summary

  • $149/SF
  • 18 Days On Market

  Last Sold Price $599,990

  Last Listing Agent Julia Foard-Lynch Samson Properties
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  /12

  $80,000

  • Land
  • 0.13 Acre
  • $615,385 per Acre

  520 Highland Ave, Winchester, VA 22601

  Empty lot ready to build a home one. The lot is fully fenced with front and rear gates. The front of the lot meets the sidewalks and road of Highland Ave. The rear of the lot meets a gravel alley way that could give access to off street parking on this lot. Homes in the city are in demand, so don't miss this opportunity. Zoned HR-1Can only be used for single family dwellingsFront setback:

  Michael Sprague Samson Properties

  520 Highland Ave, Winchester, VA 22601
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  /7

  $995 per month

  • 500 Sq Ft
  • Condo for Rent

  1816 Valley Ave Unit 3, Winchester, VA 22601

  We are okay with 6 months or Yearly lease.Freshly Remodeled Studio Apartment available. Centered in the heart of Winchester, walking distance to shops, restaurants, and entertainment. Utilities and WIFI are included at no charge. No pets allowed. Come and enjoy all of what Winchester has to offer. $995 per Month or $275 per Week. Handicap Ramp for easily access to the unit. On-site

  Raj Patel Ikon Realty - Ashburn

  1816 Valley Ave Unit 3, Winchester, VA 22601
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  /32

  $400,000 Sold Oct 09, 2025

  225 Parkway St, Winchester, VA 22601

  • 4 Beds
  • 2 Baths
  • 2,256 Sq Ft
  • Built 1928

  Last Sold Summary

  • $177/SF
  • 13 Days On Market

  Current Estimated Value $399,012

  Last Listing Agent Tracy Jewell Samson Properties

  225 Parkway St, Winchester, VA 22601
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  /8

  Not Listed For Sale

  Lot 1A Fishel Rd, Winchester, VA 22602

  Lot 1A Fishel Rd, Winchester, VA 22602

  Last Sold Summary

  • 3 Days On Market

  Last Sold Price $100,000

  Last Listing Agent RoxAnn Grimes RE/MAX
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  /11

  $80,000

  • Land
  • 0.08 Acre
  • $1,000,000 per Acre

  24 N Pleasant Valley Rd, Winchester, VA 22601

  Ready for building! Clear open lot that is ready for a home to be built. Winchester City is the fastest growing city in the state and homes are in high demand. Don't miss your opportunity. Property has road front access as well as a gravel alley in the rear that could be used for access to off street parking.Zoned MR - medium density residential districtCan only be used for single family

  Michael Sprague Samson Properties

  24 N Pleasant Valley Rd, Winchester, VA 22601
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  /25

  $2,250 per month

  • 3 Beds
  • 3.5 Baths
  • 2,970 Sq Ft
  • Townhouse for Rent

  103 Cheshire Ct, Winchester, VA 22602

  Nearly 3,000 sq. ft. of living space! This is a former Builder Model and is the largest townhome in the neighborhood. The rent includes yard maintenance & lawn mowing for carefree living. The main level offers a large formal living & dining room, a powder room, a spacious family room, a kitchen with double ovens, and a breakfast room leading to a deck with a view of trees. The upper level offers

  Theo Theologis Slones Real Estate

  103 Cheshire Ct, Winchester, VA 22602
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  /65

  $397,000 Sold Mar 27, 2025

  205 Cobble Stone Dr, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 2,263 Sq Ft
  • Built 2014

  Last Sold Summary

  • $175/SF
  • 6 Days On Market

  Current Estimated Value $408,960

  Last Listing Agent Jeffrey Konrady Realty ONE Group Old Towne

  205 Cobble Stone Dr, Winchester, VA 22602
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  /7

  Not Listed For Sale

  Lot 1B Fishel Rd, Winchester, VA 22602

  Lot 1B Fishel Rd, Winchester, VA 22602

  Last Sold Summary

  • 3 Days On Market

  Last Sold Price $125,000

  Last Listing Agent RoxAnn Grimes RE/MAX
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  /42

  $314,900

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft

  140 Mccormick Cir Unit 302, Winchester, VA 22602

  Welcome home to this gorgeous, like-new condo located in scenic and historic Winchester! This this gleaming home was just constructed and offers the perfect blend of modern elegance and cozy comfort. Enjoy top-tier finishes like quartz countertops, stainless steel appliances, and beautiful LVP flooring throughout. Relax and unwind on your private balcony overlooking the meticulously manicured

  Karl Achstetter Keller Williams Realty

  140 Mccormick Cir Unit 302, Winchester, VA 22602
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  /14

  $1,810 per month

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

  137 Fox Dr, Winchester, VA 22601

  House has been completely remodeled and looks great! This property is very close to the Winchester Hospital and it's at walking distance to downtown Winchester. The ideal tenant would have credit score 660+, monthly income corresponding to at least 4 times the amount of monthly rent, job stability, great references. Available on March 1st. Schedule a showing today!

  Elcy Pereira Elcy & Co. Realty, LLC.

  137 Fox Dr, Winchester, VA 22601
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  /24

  $370,000 Sold Nov 14, 2025

  613 Laurelwood Cir, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Dev Patel Samson Properties

  613 Laurelwood Cir, Winchester, VA 22601
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  /9

  Not Listed For Sale

  0 Shenandoah Trail, Winchester, VA 22602

  0 Shenandoah Trail, Winchester, VA 22602

  Last Sold Summary

  • 2 Days On Market

  Last Sold Price $15,000

  Last Listing Agent Stephanie Feltner Realty ONE Group Old Towne
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  /23

  $279,999 Under Contract

  • 2 Beds
  • 1.5 Baths
  • 954 Sq Ft

  407 van Fossen St, Winchester, VA 22601

  Welcome to this charming 2-bedroom, 1.5-bath home in Winchester! Featuring a recently replaced roof (2024) and double-hung windows, this home combines character and functionality. The main floor offers a bedroom with half bath, perfect for guests or home office use, while upstairs boasts a large bedroom with full bath. Enjoy cozy evenings by the brick wood-burning fireplace and the beautiful

  Michele Gibson Samson Properties

  407 van Fossen St, Winchester, VA 22601
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  /10

  $1,549 per month

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

  3107 Shawnee Dr Unit 11, Winchester, VA 22601

  *** NOW ACCPETING PETS ON CASE BY CASE BASIS***Beautifully Renovated Unit Two level townhome*Full size Washer & Dryer*Hardwood like Floors* Huge Brand New Eat-In Kitchen*Granite 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

  Steve DuBrueler Coldwell Banker Premier

  3107 Shawnee Dr Unit 11, Winchester, VA 22601
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  /57

  $420,000 Sold Mar 07, 2025

  384 Perry Rd, Winchester, VA 22602

  • 4 Beds
  • 3 Baths
  • 1,688 Sq Ft
  • Built 1969

  Last Sold Summary

  • $249/SF
  • 6 Days On Market

  Current Estimated Value $444,383

  Last Listing Agent Janet Flaherty Keller Williams Realty

  384 Perry Rd, Winchester, VA 22602
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  /14

  Not Listed For Sale

  0 Doe Trail Unit VAFV2022816, Winchester, VA 22602

  0 Doe Trail Unit VAFV2022816, Winchester, VA 22602

  Last Sold Summary

  • 2 Days On Market

  Last Sold Price $25,000

  Last Listing Agent Stephanie Feltner Realty ONE Group Old Towne
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  /31

  $454,900

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

  1025 S Loudoun St, Winchester, VA 22601

  Prepare to be wowed by this stunning renovation in downtown Winchester! This charming Colonial has been fully remodeled and is ready for new owners. No detail was spared—original features were thoughtfully preserved to maintain the home’s historic charm, while modern conveniences were added throughout for everyday living. The original hardwood floors were refinished and run throughout the house,

  Heloisa Amar Samson Properties

  1025 S Loudoun St, Winchester, VA 22601
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  /29

  $2,550 per month

  • 2 Beds
  • 1.5 Baths
  • 1,465 Sq Ft
  • Condo for Rent

  122 N Loudoun St Unit 202, Winchester, VA 22601

  Step through the doors of this luxurious flat and immerse yourself in the grandeur of Old Town Winchester. Floor to ceiling windows, gleaming hardwood floors, and premium natural quartz counter tops leave nothing to be desired. Highlighted in this contemporary design are keyless entry, dish TV, WiFi, and sleek balconies. Call now to view theFlats@Bells!

  Dave Spence RE/MAX Roots

  122 N Loudoun St Unit 202, Winchester, VA 22601
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  /37

  $345,000 Sold Apr 24, 2025

  108 Willow Trail, Winchester, VA 22602

  • 3 Beds
  • 3 Baths
  • 1,340 Sq Ft
  • Built 2007

  Last Sold Summary

  • $257/SF
  • 110 Days On Market

  Current Estimated Value $342,706

  Last Listing Agent Pamela Foltz Realty ONE Group Old Towne

  108 Willow Trail, Winchester, VA 22602
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  /4

  Not Listed For Sale

  Lot 16 E Lincoln Estates Subdivision, Winchester, VA 22602

  Lot 16 E Lincoln Estates Subdivision, Winchester, VA 22602

  Last Sold Summary

  • 14 Days On Market

  Last Sold Price $40,000

  Last Listing Agent Tracy Link Coldwell Banker Premier
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  /7

  $4,000,000 Under Contract

  • Land
  • 27.2 Acres
  • $147,059 per Acre

  0 N Frederick Pike Unit VAWI2007698, Winchester, VA 22603

  Unprecedented Development Opportunity, County of Frederick, 27.2 acres in land use plan for high density rezoning (RP) and development (currently zoned RA, will require rezoning). Ideal townhouse and apartment project. Gateway to downtown Old Town Winchester. Public utilities to site. Truly a catalyst development opportunity, located in the fast growing metropolitan area in Virginia. Voted #1

  Gillian Greenfield Coldwell Banker Premier

  0 N Frederick Pike Unit VAWI2007698, Winchester, VA 22603
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  /28

  $2,800 per month

  • 4 Beds
  • 2.5 Baths
  • 1,953 Sq Ft
  • House for Rent

  108 Manasquan Way, Winchester, VA 22602

  Relatively new home available in amenity rich new DR Horton community on Route 7 on Winchester East Side for September move-in for rental. The Pine is a 1,953 square foot open concept home, offering four bedrooms, two and a half bathrooms and a two-car garage. A foyer with a powder room and coat closet greets you as you enter this home. The open floorplan allows you and your loved ones to spend

  Vijaya Rallabandi Partners Real Estate

  108 Manasquan Way, Winchester, VA 22602
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  /60

  $660,000 Sold Oct 01, 2025

  109 Aulee Ct, Winchester, VA 22602

  • 4 Beds
  • 2.5 Baths
  • 3,165 Sq Ft
  • Built 2006

  Last Sold Summary

  • $209/SF
  • 110 Days On Market

  Current Estimated Value $657,933

  Last Listing Agent Kim Spear Keller Williams Realty

  109 Aulee Ct, Winchester, VA 22602
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  /11

  Not Listed For Sale

  LOTS 36 & 37 Meadow Way, Winchester, VA 22602

  LOTS 36 & 37 Meadow Way, Winchester, VA 22602

  Last Sold Summary

  Last Sold Price $49,900

  Last Listing Agent Bradley Comstock ERA Oakcrest Realty, Inc.
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  /49

  $422,999

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft

  709 Dicks Hollow Rd, Winchester, VA 22603

  Welcome to this private gem nestled on a corner lot in beautiful Winchester, VA! This stunning 3-bedroom, 2-bath home offers the perfect balance of modern upgrades, comfort, and peace of mind. Step inside to find a fully remodeled primary bathroom featuring a luxurious walk-in shower — a spa-like retreat in the comfort of your own home. Enjoy the confidence of a brand-new roof with a 30-year

  Fehiber Rosario NBI Realty, LLC

  709 Dicks Hollow Rd, Winchester, VA 22603
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  /7

  $1,450 per month

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

  208 W Boscawen St Unit 5, Winchester, VA 22601

  Enjoy the charm & convenience of downtown living in this 2 bedroom, 1 bath second floor apartment located just steps from Winchester's historic shops, restaurants & entertainment. This comfortable apartment features an efficient layout with easy access to coin operated laundry facilities on the main floor. A shared rear deck area provides a great spot to relax. New energy efficient windows

  Marisa Varley ERA Oakcrest Realty, Inc.

  208 W Boscawen St Unit 5, Winchester, VA 22601
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  /34

  $567,990 Sold Jul 17, 2025

  116 Munsee Cir, Winchester, VA 22602

  • 5 Beds
  • 4 Baths
  • 2,968 Sq Ft
  • Built 2025

  Last Sold Summary

  • $191/SF
  • 29 Days On Market

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

  116 Munsee Cir, Winchester, VA 22602
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  /31

  Est $333,415 Not Listed For Sale

  616 Cardinal Dr, Winchester, VA 22602

  • 3 Beds
  • 2 Baths
  • 2,072 Sq Ft
  • Built 2024

  616 Cardinal Dr, Winchester, VA 22602

  Last Sold Summary

  • 2% Below List Price
  • $164/SF
  • 55 Days On Market

  Last Sold Price $339,000

  Last Listing Agent Sheila Pack RE/MAX
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  /14

  $915,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,879 Sq Ft

  206 Covey Ln, Winchester, VA 22602

  Carrington Homes Model Home for Sale. This stunning 5-bedroom, 4.5-bathroom home with Main Level Bedroom, built in 2025. Nestled on 2.66 acres, this residence offers a serene view of lush trees and woods, creating a peaceful backdrop for your everyday life. The heart of the home features a gourmet kitchen equipped with ENERGY STAR stainless steel appliances, including a double oven and built-in

  Daniel Boris Pearson Smith Realty, LLC

  206 Covey Ln, Winchester, VA 22602
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  /5

  $1,300 per month

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

  208 W Boscawen St Unit 12, Winchester, VA 22601

  This apartment is conveniently located to downtown Winchester. Coin Op Washer & Dryer on the main level. Rear deck access. Water & Sewer, weekly trash service and monthly pest treatment included in rent. Cat considered, no dogs. Minimum credit score of 650 and income equaled to 3X the rent required to apply. No Prior evictions.

  Marisa Varley ERA Oakcrest Realty, Inc.

  208 W Boscawen St Unit 12, Winchester, VA 22601
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  $1,299,000 Sold Aug 05, 2025

  374 Stonymeade Dr, Winchester, VA 22602

  • 5 Beds
  • 3.5 Baths
  • 4,702 Sq Ft
  • Built 2019

  Last Sold Summary

  • $276/SF
  • 3 Days On Market

  Current Estimated Value $1,252,182

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

  374 Stonymeade Dr, Winchester, VA 22602
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  /35

  Est $600,867 Not Listed For Sale

  440 Cattail, Winchester, VA 22603

  • 3 Beds
  • 2 Baths
  • 1,616 Sq Ft
  • Built 2013

  440 Cattail, Winchester, VA 22603

  Last Sold Summary

  • 12% Above List Price
  • $332/SF
  • 14 Days On Market

  Last Sold Price $536,000

  Last Listing Agent Katherine (Kat) Wetzel Century 21 Redwood Realty

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