Winchester, VA Homes

• 

  

  

  /52

  $410,000 Under Contract

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

  128 Killbuck Trail, Winchester, VA 22602

  Welcome to 128 Killbuck Trail, a beautifully maintained 2019 split-foyer home that truly shows like new. Freshly painted throughout, this residence features granite countertops in the kitchen and bathrooms and has an open, inviting floor plan perfect for everyday living and entertaining.The main level offers three spacious bedrooms, including a primary suite with an en-suite bath. The lower

  Leah Clowser RE/MAX Roots

  128 Killbuck Trail, Winchester, VA 22602
• 

  

  

  /8

  $1,595 per month

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Townhouse for Rent

  202 E Whitlock Ave, Winchester, VA 22601

  Experience the charm of this beautifully renovated end-of-row townhouse in the heart of the City of Winchester, available for lease starting November 19, 2025. This residence, originally built in 1956, will undergo a major renovation, ensuring modern luxury meets classic elegance. With three spacious bedrooms and a full bath, this home is designed for comfort and style. The partially finished

  Brandon Pifer Pifer Realty, LLC

  202 E Whitlock Ave, Winchester, VA 22601
• 

  

  

  /75

  $1,071,134 Sold Jul 31, 2025

  220 Anna Margaret Dr, Winchester, VA 22602

  • 4 Beds
  • 5 Baths
  • 5,000 Sq Ft
  • Built 2006

  Last Sold Summary

  • $214/SF
  • 1 Day On Market

  Current Estimated Value $1,042,885

  Last Listing Agent Bradley Comstock ERA Oakcrest Realty, Inc.

  220 Anna Margaret Dr, Winchester, VA 22602
• 

  

  

  /22

  Not Listed For Sale

  3146 Eton Place, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,928 Sq Ft
  • Built 2024

  3146 Eton Place, Winchester, VA 22601

  Last Sold Summary

  • $210/SF
  • 51 Days On Market

  Last Sold Price $405,250

  Last Listing Agent Brittany Newman DRB Group Realty, LLC
• 

  

  

  /56

  $439,000 Coming Soon

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  743 Berryville Ave, Winchester, VA 22601

  Welcome to 743 Berryville Ave in the heart of Downtown Winchester! This unique and versatile property offers exceptional space and flexibility with two fully equipped living areas on one lot.The main house features 4 bedrooms, 2 full bathrooms, 2 kitchens, and 2 laundry areas—ideal for multi-generational living or added convenience. Enjoy a spacious layout with plenty of room for everyone to

  Sineenat Sirimas Pearson Smith Realty, LLC

  743 Berryville Ave, Winchester, VA 22601
• 

  

  /7

  $1,795 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 and central AC. updated kitchen and much more. Large backyard that is 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

  Jarrett Sowder RE/MAX Roots

  125 Early Dr, Winchester, VA 22603
• 

  

  /58

  $445,000 Sold Dec 09, 2025

  125 Alliance Ct, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 2,176 Sq Ft
  • Built 2021

  Last Sold Summary

  • $205/SF
  • 6 Days On Market

  Current Estimated Value $449,404

  Last Listing Agent Rhonda Shade ERA Oakcrest Realty, Inc.

  125 Alliance Ct, Winchester, VA 22602
• 

  

  /22

  Not Listed For Sale

  3132 Eton Place, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 2,074 Sq Ft
  • Built 2024

  3132 Eton Place, Winchester, VA 22601

  Last Sold Summary

  • $193/SF
  • 21 Days On Market

  Last Sold Price $400,736

  Last Listing Agent Brittany Newman DRB Group Realty, LLC
• 

  

  /49

  $675,000

  • 5 Beds
  • 3.5 Baths
  • 3,294 Sq Ft

  200 & 210 W Fairfax Ln, Winchester, VA 22601

  Nestled in the heart of Winchester's cherished historic district, this enchanting circa 1928 cottage blends timeless charm with exceptional opportunity. Rich in character and architectural detail, the home showcases the craftsmanship of a bygone era - warm hardwood floors, inviting living spaces, and distinctive period touches that create an atmosphere both welcoming and refined. The home's

  John Schroth Colony Realty

  200 & 210 W Fairfax Ln, 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. Freshly painted and move-in ready. 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 650 or

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  24 Jackson Ave Unit 2, Winchester, VA 22601
• 

  

  /60

  $400,000 Sold Aug 26, 2025

  319 Beechcroft Rd, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 2,538 Sq Ft
  • Built 1961

  Last Sold Summary

  • $158/SF
  • 4 Days On Market

  Current Estimated Value $393,391

  Last Listing Agent Gidget Smallwood Coldwell Banker Premier

  319 Beechcroft Rd, Winchester, VA 22601
• 

  

  /41

  Est $478,117 Not Listed For Sale

  2060 Taylor Grace Ct, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 1,776 Sq Ft
  • Built 2011

  2060 Taylor Grace Ct, Winchester, VA 22601

  Last Sold Summary

  • 10% Above List Price
  • $244/SF
  • 22 Days On Market

  Last Sold Price $433,000

  Last Listing Agent Paul Gallagher Colony Realty
• 

  

  /43

  $592,990 New Construction

  • 6 Beds
  • 4.5 Baths
  • 3,619 Sq Ft

  125 Mascouten St, Winchester, VA 22602

  Quick Move-In Salem! This spacious 6 bedroom, 4.5 bath home offers 2,686 sq ft on the top two floors with a first-floor primary suite for easy main-level living. The open-concept design is perfect for entertaining, and the stone front elevation adds timeless curb appeal. Enjoy the added space of a finished recreation room with an additional bedroom—ideal for guests or a home office. Ask about

  D.R. Horton Builder

  125 Mascouten St, Winchester, VA 22602
• 

  

  /23

  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Townhouse for Rent

  321 N Braddock St, Winchester, VA 22601

  Gorgeously remodeled 2 Bedroom 1 Bath two-story apartment located in Charming Historic Downtown Winchester. This apartment has been freshly painted and updated with Brand New Appliances to include Refrigerator, stove, rangehood, washer and dryer. Additional updates include new kitchen sink, countertops, light fixtures, blinds, and ceramic tub surround. Light and Bright this apartment has two

  Angela Duncan MarketPlace REALTY

  321 N Braddock St, Winchester, VA 22601
• 

  

  /28

  $440,000 Sold Jan 26, 2026

  386 Round Hill Rd, Winchester, VA 22602

  • Studio
  • 2,736 Sq Ft
  • Built 1950

  Last Sold Summary

  • $161/SF
  • 186 Days On Market

  Current Estimated Value $446,046

  Last Listing Agent Bridget Aikens Colony Realty

  386 Round Hill Rd, Winchester, VA 22602
• 

  

  /43

  Est $573,077 Not Listed For Sale

  2044 Taylor Grace Ct, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 3,568 Sq Ft
  • Built 2011

  2044 Taylor Grace Ct, Winchester, VA 22601

  Last Sold Summary

  • 4% Above List Price
  • $154/SF
  • 10 Days On Market

  Last Sold Price $549,900

  Last Listing Agent Cynthia Lee RE/MAX
• 

  

  /8

  $785,000 New Construction

  • 3 Beds
  • 3 Baths
  • 2,548 Sq Ft

  0 Apple Pie Ridge Rd Unit VAFV2039276, Winchester, VA 22603

  Dogwood - One Story Living Carrington Homes Western Loudoun’sPremiere Home builder introduces its newWinchester Collection of single familyHomes on a private 2 acre lot.Custom style homes designedBy James McDonald Architects One story and two story plans withFirst floor multi generational options available DECORATED MODELS located at 156 Covey Lane Winchester

  Daniel Boris Pearson Smith Realty, LLC

  0 Apple Pie Ridge Rd Unit VAFV2039276, Winchester, VA 22603
• 

  

  /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
• 

  

  /33

  $607,990 Sold Nov 05, 2025

  111 Mascouten St, Winchester, VA 22602

  • 5 Beds
  • 3 Baths
  • 2,511 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $242/SF
  • 15 Days On Market

  D.R. Horton Retreat at Winding Creek - Single Family

  111 Mascouten St, Winchester, VA 22602
• 

  

  /31

  Est $344,244 Not Listed For Sale

  123 Monticello Square, Winchester, VA 22602

  • 3 Beds
  • 4 Baths
  • 1,740 Sq Ft
  • Built 2009

  123 Monticello Square, Winchester, VA 22602

  Last Sold Summary

  • 6% Above List Price
  • $187/SF
  • 9 Days On Market

  Last Sold Price $324,990

  Last Listing Agent Paul Gallagher Colony Realty
• 

  

  /91

  $674,900 Under Contract

  • 7 Beds
  • 3.5 Baths
  • 4,276 Sq Ft

  225 Lehigh Dr, Winchester, VA 22602

  This beautiful energy-efficient home backs to open space with a tot lot and offers abundant natural light along with thoughtful upgrades throughout. A 9 kW peak solar panel system installed in November 2024 provides electricity for the home, significantly reducing energy costs. Additional enhancements include a whole-house water softener, an upgraded washer and dryer with storage located in a

  RAFIQUE JAMAL Pi Realty Group, Inc.

  225 Lehigh Dr, Winchester, VA 22602
• 

  

  /47

  $2,195 per month

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • House for Rent

  2253 Papermill Rd, Winchester, VA 22601

  ** AVAILABLE NOW **A fantastic, rare opportunity to rent a 3-bedroom, 2-bathroom single-family home in the heart of Winchester, Virginia. The home features a highly desirable open-concept layout with an abundance of natural light and spacious rooms throughout. The kitchen is designed for functionality and features a full suite of high-end appliances and ample cabinetry, ready for your cookware

  Raman Singh Prime Properties DMV, LLC.

  2253 Papermill Rd, Winchester, VA 22601
• 

  

  /17

  $364,990 Sold Mar 28, 2025

  107 Nootka Way, Winchester, VA 22602

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

  Last Sold Summary

  • $242/SF
  • 114 Days On Market

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

  107 Nootka Way, Winchester, VA 22602
• 

  

  /29

  Est $338,206 Not Listed For Sale

  308 Fawn Dr, Winchester, VA 22602

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • Built 2009

  308 Fawn Dr, Winchester, VA 22602

  Last Sold Summary

  • 7% Above List Price
  • $188/SF
  • 1 Day On Market

  Last Sold Price $315,000

  Last Listing Agent Lisa Cromwell Atoka Properties | Middleburg Real Estate
• 

  

  /51

  $739,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,442 Sq Ft

  806 Mahone Dr, Winchester, VA 22601

  Gorgeous Home in Meadow Branch!Welcome to this beautifully maintained home in the highly desirable Meadow Branch community! Featuring a sought-after main level primary suite, this property offers comfort, convenience, and easy living in one of Winchester’s most popular neighborhoods. The spacious primary bath feels like a private retreat with its spa-like atmosphere — the perfect place to

  Tiffany Hunter ERA Oakcrest Realty, Inc.

  806 Mahone Dr, Winchester, VA 22601
• 

  

  /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
• 

  

  /27

  $165,000 Sold Apr 25, 2025

  1436 Pack Horse Rd, Winchester, VA 22603

  • 3 Beds
  • 2 Baths
  • Built 1990

  Last Sold Summary

  • 149 Days On Market

  Last Listing Agent Roxane Morrison NextHome Realty Select

  1436 Pack Horse Rd, Winchester, VA 22603
• 

  

  /44

  Not Listed For Sale

  412 Fawn Dr, Winchester, VA 22602

  • 3 Beds
  • 2.5 Baths
  • 1,285 Sq Ft
  • Built 2009

  412 Fawn Dr, Winchester, VA 22602

  Last Sold Summary

  • 1% Below List Price
  • $246/SF
  • 3 Days On Market

  Last Sold Price $316,000

  Last Listing Agent Jodi Costello ERA Oakcrest Realty, Inc.
• 

  

  /33

  $245,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  815 Pheasant Dr, Winchester, VA 22602

  Affordable and move-in ready ranch-style home on a little more than a half acre. The mature trees, abundant wildlife, and quiet location make this a serene location. Featuring 2 bedrooms and 1 full bath, this home was freshly painted (Nov 2025) and underwent a major renovation in 2017 (roof, HVAC, water heater, floors, fixtures, and more). Enjoy the comfort of 1-level living with plenty of

  Eric Kronenwetter RE/MAX Roots

  815 Pheasant Dr, Winchester, VA 22602
• 

  

  /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
• 

  

  /25

  $360,000 Sold Jul 22, 2025

  108 Oakmont Cir, Winchester, VA 22602

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft
  • Built 1986

  Last Sold Summary

  • $268/SF
  • 4 Days On Market

  Current Estimated Value $356,104

  Last Listing Agent Stacey Mullins ERA Oakcrest Realty, Inc.

  108 Oakmont Cir, Winchester, VA 22602
• 

  

  /27

  Est $342,168 Not Listed For Sale

  113 Monticello Square, Winchester, VA 22602

  • 3 Beds
  • 4 Baths
  • 1,740 Sq Ft
  • Built 2009

  113 Monticello Square, Winchester, VA 22602

  Last Sold Summary

  • 1% Above List Price
  • $195/SF
  • 7 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Angie Ordonez NextHome Realty Select
• 

  

  /39

  $579,990 New Construction

  • 6 Beds
  • 4 Baths
  • 3,127 Sq Ft

  HAYDEN Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

  The Hayden is a two-story plan with 6 bedrooms and 3 bathrooms in over 3,100 total square feet. The main level features a flex room adjacent to the foyer, ideal for a formal dining room or home office. The gourmet kitchen has an oversized island for extra seating and a large pantry, and it opens to the dining area and a spacious living room. A bedroom with a full bathroom completes the main

  D.R. Horton Builder

  137 Seminole Dr Unit 36203781, Winchester, VA 22602
• 

  

  /15

  $1,600 per month

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

  307 Willowbrook Ct, Winchester, VA 22602

  Located in the highly sought-after East End of Winchester, this exceptional all-brick end-unit townhome is just minutes from Rt. 7 and I-81, offering an unbeatable commuter location. Close to shopping and only a short drive to the charming downtown Winchester walking mall, this home is perfectly positioned for convenience and comfort.Meticulously maintained by the owners, this move-in ready

  Jeff Boppe Long & Foster Real Estate, Inc.

  307 Willowbrook Ct, Winchester, VA 22602
• 

  /2

  $205,000 Sold Apr 30, 2025

  264 Shenandoah Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 913 Sq Ft
  • Built 1954

  Last Sold Summary

  • $225/SF
  • 0 Days On Market

  Current Estimated Value $218,438

  Last Listing Agent Pamela Dors Keller Williams Realty Advantage

  264 Shenandoah Ave, Winchester, VA 22601
• 

  

  /58

  Est $681,988 Not Listed For Sale

  730 Old Baltimore Rd, Winchester, VA 22603

  • 4 Beds
  • 2.5 Baths
  • 3,912 Sq Ft
  • Built 2009

  730 Old Baltimore Rd, Winchester, VA 22603

  Last Sold Summary

  • 13% Above List Price
  • $154/SF
  • 44 Days On Market

  Last Sold Price $602,000

  Last Listing Agent Cara Wilkins MarketPlace REALTY
• 

  

  /17

  $459,999 Coming Soon

  • 4 Beds
  • 3 Baths
  • 2,632 Sq Ft

  119 Foxglove Dr, Winchester, VA 22602

  Welcome to 119 Foxglove Drive! This beautifully maintained home is tucked away in a quiet Winchester neighborhood in a GREAT location, close to Rt 7 & downtown Winchester City. This home offers the perfect blend of comfort, space, and convenience. From the moment you arrive, you’ll appreciate the inviting curb appeal and the quiet and private cul de sac.Step inside to discover a bright and

  Michele Gibson Samson Properties

  119 Foxglove Dr, Winchester, VA 22602
• 

  

  /13

  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Condo for Rent

  5 Brookland Ct, Winchester, VA 22602

  Well maintained 2 bedroom 2 bath unit on 2nd floor. Gas fireplace and private balcony. Ready for move in. Landlord requires Minimum credit score of 700 and income of 3X the rent. Pets are welcome case by case. No prior evictions. Apply online using RentSpree link. All adults over 18 must apply $35 application fee per applicant.

  Hushai Mesfin Samson Properties

  5 Brookland Ct, Winchester, VA 22602
• 

  

  /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 $586,434

  Last Listing Agent Amber Jenkins Century 21 Redwood Realty

  251 Heather Hill Ln, Winchester, VA 22603
• 

  

  /11

  Est $227,095 Not Listed For Sale

  164 Brookland Ct Unit 11, Winchester, VA 22602

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Built 2002

  164 Brookland Ct Unit 11, Winchester, VA 22602

  Last Sold Summary

  • 26% Above List Price
  • $153/SF
  • 17 Days On Market

  Last Sold Price $180,000

  Last Listing Agent Kevin Drake Coldwell Banker Premier

Showing Results 441 - 480, Page 12 of 18