Winchester, VA Homes

• 

  $452,539 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  0 Homesite 20 Monteith Dr Unit 36425637, Winchester, VA 22601

  End Of Row Townhome With 1 Car Garage, Gourmet Kitchen & Rear Deck! This home has a Gourmet Kitchen: cooktop with chimney style hood, wall microwave, wall oven, upgraded gourmet Energy Star stainless steel appliances, Refrigerator is a French 2 door style, the kitchen island is extended to comfortably seat 4, a box bay window in the rear of the home for extra lighting, and a 10 ft. x 14 ft. deck.

  

  DRB Homes

  Builder

  0 Homesite 20 Monteith Dr Unit 36425637, Winchester, VA 22601
• 

  

  

  /17

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 2,240 Sq Ft
  • House for Rent

  216 N Braddock St, Winchester, VA 22601

  Old charm meets custom architectural design. Remodeled to perfection including a modern kitchen, sunken living room and spa-like bathrooms. Backyard paradise allows you to enjoy the outdoor space. Rare oversized detached garage. Above the garage is a finished office space fit for an architect. So quit your commute and come work from home. Located in Historic downtown Winchester convenient to

  Amanda Slate Keller Williams Realty

  216 N Braddock St, Winchester, VA 22601
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  /18

  $330,000 Sold Jul 28, 2025

  • 1,202 Sq Ft
  • $275/SF
  • 0 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1830

  411 N Loudoun St Unit 104, Winchester, VA 22601

  Just minutes from the walking mall and the charming shops and restaurants of downtown Winchester, this fantastic two-story condo offers the perfect blend of historic character and modern comfort.Step inside to find beautiful hardwood floors and stylish finishes throughout. The fully equipped kitchen features rich dark cabinetry, granite countertops, gas cooking, and a spacious peninsula that

  Lori Bales Keller Williams Realty

  411 N Loudoun St Unit 104, Winchester, VA 22601
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  /2

  Est $903,054 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,190 Sq Ft

  137 W Boscawen St, Winchester, VA 22601

  137 W Boscawen St, Winchester, VA 22601
• 

  $433,880 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  0 Homesite 117 Monteith Dr Unit 36422335, Winchester, VA 22601

  3 Level End of Row Townhome With 1 Car Garage & Rear Deck! Beautiful open concept living 3 level town home built on concrete slab with a walk-out lower level. Finished Rec Room - 13 ft. 1 in. x 11 ft. 1 in. with a door to the outside/backyard. The living room area is 15 ft. 3 in. x 17 ft., open kitchen layout with an extended island, a box bay window and 10 ft. x 14 ft. deck in the rear of home.

  

  DRB Homes

  Builder

  0 Homesite 117 Monteith Dr Unit 36422335, Winchester, VA 22601
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  /17

  $500 - $2,000 per month

  Brookfield Corporate Apartments

  1 - 2 Beds

  548 Brookfield Dr, Winchester, VA 22601

  We are excited to share that we are under new ownership and management, and we're eager to welcome new guests to our community.Located at 500 Brookfield Drive, Winchester, VA 22601, Brookfield Corporate Apartments offers spacious, fully furnished one and two-bedroom apartments. Each apartment is designed with your comfort in mind and comes equipped with linens, kitchenware, two TVs with

  548 Brookfield Dr, Winchester, VA 22601
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  /47

  $309,000 Sold Jul 28, 2025

  • 2,348 Sq Ft
  • $132/SF
  • 6 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1950

  233 Molden Dr, Winchester, VA 22601

  Charming All-Brick Ranch with Endless Potential in Established Neighborhood! Don't miss this solid 3+ bedroom, 1.5 bath all-brick ranch offering timeless appeal and the opportunity to make it your own. Nestled in a well-established neighborhood, this home features original hardwood floors, a cozy fireplace for chilly evenings, and radiant ceiling heat for comfortable, energy-efficient warmth

  Kevin Smith Sager Real Estate

  233 Molden Dr, Winchester, VA 22601
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  /3

  Not Listed For Sale

  2902 Valley Ave, Winchester, VA 22601

  2902 Valley Ave, Winchester, VA 22601
• 

  $429,340 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  0 Homesite 114 Monteith Dr Unit 36422292, Winchester, VA 22601

  3 Level Townhome With Over 1,600 Finished sq. ft., 1 Car Garage & Rear Deck! Bedford II, 3 level townhome features a partial stone front with 1 car garage. This home features 3 Bedrooms and 3.5 Baths. It is fully finished top to bottom. The front door leads directly into the spacious lower level including 9 ft. ceilings, foyer with a double coat closet, access to the garage with a garage door

  

  DRB Homes

  Builder

  0 Homesite 114 Monteith Dr Unit 36422292, Winchester, VA 22601
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  /18

  $2,150 per month

  • 3 Beds
  • 2.5 Baths
  • 1,500 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 Ikon Realty - Ashburn

  413 Tevis St, Winchester, VA 22601
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  /68

  $700,000 Sold Jul 25, 2025

  • 1,664 Sq Ft
  • $421/SF
  • 8 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1967

  516 Merrimans Ln, Winchester, VA 22601

  Amazing Opportunity--First time on the market, this mid-century Ranch comes with updated bathrooms and custom kitchen. The 1.4 acre property includes an in-ground pool and guest house with full bath and kitchenette. Densely landscaped property provides almost complete privacy on one of the few remaining spacious lots inside the city. A large Lanai complements the property for entertaining or

  Dallas Croft Samson Properties

  516 Merrimans Ln, Winchester, VA 22601
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  /2

  Not Listed For Sale

  • Studio
  • 1,693 Sq Ft

  408 Diehl St, Winchester, VA 22601

  408 Diehl St, Winchester, VA 22601
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  /48

  $534,900 Open Sat 1PM - 3PM

  • 3 Beds
  • 3 Baths
  • 2,285 Sq Ft

  257 Jefferson St, Winchester, VA 22601

  Charming Craftsman in West Whitlock Avenue – Walk to John Handley!Welcome to 257 Jefferson Street, a beautifully maintained 3-bedroom, 1 full and 2 half bath Craftsman-style home located in the highly desirable West Whitlock Avenue subdivision. This 2,285 sq ft gem offers timeless charm, modern updates, and a prime location within walking distance to the prestigious John Handley High

  Kathrin Donovan Keller Williams Realty

  257 Jefferson St, Winchester, VA 22601
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  /26

  $1,695 - $1,702 per month

  Fort Collier Terrace

  1 - 3 Beds

  900-1024 N Braddock St, Winchester, VA 22601

  Welcome to Fort Collier Terrace, an inviting community you'll love being part of. Our apartments in Winchester, VA, come in one, two, and three-bedroom layouts that range from 800 to 1,000 square feet. Aside from the generous living quarters, you'll find everything you need to feel right at home.Located near N Cameron Street and Martinsburg Pike, you're a stone's throw away from the top dining,

  900-1024 N Braddock St, Winchester, VA 22601
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  /27

  $325,000 Sold Jul 25, 2025

  • 1,900 Sq Ft
  • $171/SF
  • 3 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1964

  412 Fairview Ave, Winchester, VA 22601

  Welcome to 412 Fairview Ave. A ranch-style home with a full basement.This house features hardwood floors, a gas fireplace in the living room, and a central vacuum system.On the main level, you'll find three bedrooms and two full bathrooms. The kitchen comes fully equipped with a stove, refrigerator, microwave, and dishwasher, all of which convey along with the window treatments.

  Junue Hernandez Rojas Long & Foster Real Estate, Inc.

  412 Fairview Ave, Winchester, VA 22601
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  /4

  Est $890,867 Not Listed For Sale

  601 W Jubal Early Dr, Winchester, VA 22601

  601 W Jubal Early Dr, Winchester, VA 22601
• 

  

  /90

  $515,000

  • 3 Beds
  • 2.5 Baths
  • 1,984 Sq Ft

  2623 Middle Rd, Winchester, VA 22601

  Welcome home to 2623 Middle Rd! Located near all that Winchester has to offer, Middle Rd is a lovely private oasis to come home to. With a myriad of upgrades including a gorgeous screened in back porch, this home offers many conveniences, a spacious layout and bedrooms, and plenty of room for entertainment, hobbies, and whatever you can dream of. Outfitted with a new greenhouse and shed, both

  Nicole Lewis Coldwell Banker Premier

  2623 Middle Rd, Winchester, VA 22601
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  /34

  $1,395 per month

  • 2 Beds
  • 1 Bath
  • 1,022 Sq Ft
  • Townhouse for Rent

  221 Baker St, Winchester, VA 22601

  MOVE-IN READY Adorable downtown Winchester duplex in a quiet neighborhood! Features:Spacious living area on the main floorFreshly painted all throughoutKitchen with separate dining areaMicrowave, washer, and dryer includedTwo bedrooms & one bathroom upstairsCharming front porch & backyard with storage shed accessPhotos from last year Rental

  Elna Brown Pearson Smith Realty, LLC

  221 Baker St, Winchester, VA 22601
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  /31

  $310,000 Sold Jul 25, 2025

  • 1,620 Sq Ft
  • $191/SF
  • 0 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1986

  7 E Hart St, Winchester, VA 22601

  Beautifully Maintained and Ideally Located!Nestled within city limits and just minutes from shopping, local dining, and the vibrant downtown walking mall, this home offers the perfect blend of comfort and convenience. Recent updates include fresh paint on all interior levels (2025), new carpet (2025), upgraded granite countertops (2019), a 30-year Timberline American Harvest roof (2017),

  Jennifer Sacco RE/MAX Roots

  7 E Hart St, Winchester, VA 22601
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  /12

  Not Listed For Sale

  • Studio
  • 2,376 Sq Ft

  1021 Franklin St, Winchester, VA 22601

  1021 Franklin St, Winchester, VA 22601
• 

  

  /46

  $460,000

  • 4 Beds
  • 2.5 Baths
  • 2,523 Sq Ft

  2876 Packer St, Winchester, VA 22601

  Spacious 4-Bedroom Colonial in a Prime Winchester Location!This 4-bedroom, 2.5-bath colonial offers over 2,500 square feet of finished living space across three levels, ideally located just minutes from I‐81 and Route 66 for easy commuting and convenience.Inside, hardwood floors span the main level, where a bright, open layout is perfect for everyday living and entertaining. The kitchen

  Kristina Towns Weichert Realtors - Blue Ribbon

  2876 Packer St, Winchester, VA 22601
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  /22

  $1,490 - $1,745 per month

  Blue Ridge Apartments

  2 - 4 Beds

  2260 Wilson Blvd, Winchester, VA 22601

  Discover the perfect blend of comfort and convenience at Blue Ridge Apartments in Winchester, VA. Our recently updated homes feature a variety of floor plans. Nestled in a pet-friendly community, you're just minutes away from Winchester's scenic spots, historic downtown, Apple Blossom Mall, and major employers. With easy access to I-81 and Route 7, the best of Winchester is always within reach.

  2260 Wilson Blvd, Winchester, VA 22601
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  /48

  $335,200 Sold Jul 25, 2025

  • 2,606 Sq Ft
  • $129/SF
  • 25 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1961

  128 Fox Dr, Winchester, VA 22601

  Welcome to 128 Fox Dr — a spacious, move-in ready home nestled in the heart of Winchester, offering three levels spanning over 2,600 square feet of flexible living space, with 4 bedrooms, 3 bathrooms, and unbeatable convenience! This Cape Cod-style home features a thoughtful layout with at least one bedroom and a full bathroom on every level. Step into the main level to discover hardwood floors

  MJ Frazier Serhant

  128 Fox Dr, Winchester, VA 22601
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  /41

  Est $461,891 Not Listed For Sale

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

  2060 Taylor Grace Ct, Winchester, VA 22601

  2060 Taylor Grace Ct, Winchester, VA 22601
• 

  

  /39

  $419,900 Open House 8/17

  • 5 Beds
  • 2 Baths
  • 2,363 Sq Ft

  707 S Braddock St, Winchester, VA 22601

  Welcome to this charming, fully remodeled home located in the heart of Winchester.Experience the timeless appeal of Old Winchester charm, just minutes from the vibrant walking mall, shops, restaurants, and the famous Apple Blossom Parade route. This beautifully remodeled home features LVP flooring throughout and a light-filled open floor plan that seamlessly blends historic character with

  Heloisa Amar Samson Properties

  707 S Braddock St, Winchester, VA 22601
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  /22

  $1,495 per month

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

  7 W Piccadilly St Unit F, Winchester, VA 22601

  Live, work and play in historic downtown Winchester! Presenting this beautiful 1 bedroom, 1 bathroom apartment conveniently located on Piccadilly Street right next to the pedestrian mall. The apartment offers beautiful hardwood floors, tall ceilings, washer and dryer in the unit and more. You will also receive an assigned parking space next to the building. A literal stone's throw from shops and

  Chris Roszko Colony Realty

  7 W Piccadilly St Unit F, Winchester, VA 22601
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  /14

  Sold Jul 24, 2025

  • 1,442 Sq Ft

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  611 Laurelwood Cir, Winchester, VA 22601

  Quick Move-In Poplar available at Laurelwood Commons in Winchester, VA - walkable to downtown and parks! July delivery, 3 beds, 2.5 baths, 1-car garage, white cabinets, LVP flooring in the great room, kitchen island, washer/dryer, included lawn maintenance and more! Enjoy ALL closing costs paid with use of NVR Mortgage.* Learn more.

  Ryan Homes

  611 Laurelwood Cir, Winchester, VA 22601
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  /43

  Est $550,163 Not Listed For Sale

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

  2044 Taylor Grace Ct, Winchester, VA 22601

  2044 Taylor Grace Ct, Winchester, VA 22601
• 

  

  /49

  $669,000

  • 4 Beds
  • 2.5 Baths
  • 3,512 Sq Ft

  2321 Stoneridge Rd, Winchester, VA 22601

  Must see colonial in Harvest Ridge on just over 0 .4 acre in the city of Winchester. The open foyer invites you into this spacious home boasting over 3500 sq.ft. plus a full walk-out basement, ready to finish for additional square footage. Large living and dining rooms with hardwood, den or office. Large kitchen features granite counters, stainless steel appliances, and a breakfast area that

  John Schroth Colony Realty

  2321 Stoneridge Rd, Winchester, VA 22601
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  /2

  $1,600 - $1,800 per month

  Apartment for Rent

  1 - 2 Beds

  148 N Loudoun St, Winchester, VA 22601

  Beautiful 1 and 2 bedroom fully furnished apartments. Located directly on the old town walking mall. Washer dryer included in the unit. On site parking.

  148 N Loudoun St, Winchester, VA 22601
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  /59

  $630,000 Sold Jul 24, 2025

  • 3,842 Sq Ft
  • $164/SF
  • 31 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1988

  1532 Dalton Place, Winchester, VA 22601

  This home charms from the outside in. The facade is a handsome combination of brick and slate blue siding with a gabled roof and attractive octagonal bump-out. Surrounded by lush landscaping and nestled atop a small hill, the brick walk welcomes you like a personal invitation. Inside, the blend of old school craftsmanship and chic continues. Real hardwood floors, tasteful contemporary paint

  Dan Whitacre Colony Realty

  1532 Dalton Place, Winchester, VA 22601
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  /45

  Est $558,141 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,426 Sq Ft

  2040 Taylor Grace Ct, Winchester, VA 22601

  2040 Taylor Grace Ct, Winchester, VA 22601
• 

  

  /40

  $469,900

  • 5 Beds
  • 2 Baths
  • 1,956 Sq Ft

  116 S Pleasant Valley Rd, Winchester, VA 22601

  Welcome to 116 South Pleasant Valley Road! This fully-renovated gem has been meticulously transformed to offer a truly luxurious and modern living experience. You'll immediately appreciate the high-end finishes that grace every corner, making it feel brand new. Featuring 2 HVAC systems. The updated kitchen is a chef's delight, featuring new porcelain tile floors, sleek modern cabinetry, and

  Dan Whitacre Colony Realty

  116 S Pleasant Valley Rd, Winchester, VA 22601
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  /19

  $3,100 per month

  • 3 Beds
  • 1.5 Baths
  • 1,696 Sq Ft
  • House for Rent

  1315 Handley Ave, Winchester, VA 22601

  1 block away from Handley High School! This all brick 2 story home features 3 bedroom 1 1/2 baths with hardwood floors throughout the first and 2nd floors, freshly painted throughout, all new windows, and new flooring in the kitchen. Large family room with built in shelving and fireplace with woodstove insert. Full unfinished attic and basement. Beautifully landscaped rear lawn with patio and

  Misty Miller OliveTree Property Group, LLC

  1315 Handley Ave, Winchester, VA 22601
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  /63

  $535,000 Sold Jul 24, 2025

  • 3,118 Sq Ft
  • $172/SF
  • 56 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1974

  303 Walker St, Winchester, VA 22601

  Welcome to this beautifully maintained 4-bedroom, 3-bathroom home on a prime corner lot in Whittier Acres! Located on a quiet cul-de-sac and just a short stroll to Whittier Park and the Museum of the Shenandoah Valley, this home offers both convenience and charm. The meticulously landscaped yard sets the tone for the care found throughout the property. Inside, you'll find refinished hardwood

  Frank Armstrong, IV Colony Realty

  303 Walker St, Winchester, VA 22601
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  /26

  Est $383,204 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  444 Superior Ave, Winchester, VA 22601

  444 Superior Ave, Winchester, VA 22601
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  /114

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 1,798 Sq Ft

  720 S Kent St, Winchester, VA 22601

  Welcome to the beautifully preserved American Foursquare where music legend Patsy Cline once lived with her mother—and later, with her husband, Charlie Dick. Built in 1931, this four-bedroom, one-and-a-half-bath home blends timeless character with thoughtful updates, all wrapped in the charm of one of Winchester’s most historic neighborhoods.Inside, you’ll find nearly 1,800 square feet of

  Krissy Cruse Pearson Smith Realty, LLC

  720 S Kent St, Winchester, VA 22601
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  /20

  $1,600 - $2,600 per month

  Apartment for Rent

  Studio - 2 Beds

  114 N Loudoun St, Winchester, VA 22601

  Brand new fully furnished extended stay apartments in the heart of Old Town Winchester Virginia including all utilities, washer /dyer, high speed internet, free nightly and weekend parking ( 5pm to 8 am), keyless entry, 10' ceilings, exposed brick interior partitions and optional weekly cleaning.. More information can be found at themerchantsuites

  114 N Loudoun St, Winchester, VA 22601
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  /34

  $412,000 Sold Jul 23, 2025

  • 1,762 Sq Ft
  • $234/SF
  • 136 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2006

  2320 Tower Ave, Winchester, VA 22601

  Seller is offering $10,000 closing cost assistance!!!Don't drag your feet before this one disappear!!! Welcome to 2320 Tower Ave , Two Car garages ,4 legal bedrooms , 2 full bathrooms single family in quiet cul-de-sac is what you are waiting for is finally here to make it yours, the entire house just came out of renovations from freshly painted , Master Bathroom/Quartz, High

  Alex Adomako-Acheampong Samson Properties

  2320 Tower Ave, Winchester, VA 22601
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  /24

  Est $414,620 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,288 Sq Ft

  428 Superior Ave, Winchester, VA 22601

  428 Superior Ave, Winchester, VA 22601

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