Winchester, VA Homes

• 

  

  

  /46

  $425,000

  • 3 Beds
  • 3 Baths
  • 1,806 Sq Ft

  133 Woodrow Rd, Winchester, VA 22602

  Welcome home to this charming split foyer in Carlisle Heights, ideally located on the east side of Winchester—just off Route 7 for an easy commute!Step inside to a light-filled interior featuring low-maintenance flooring throughout the main living areas and bedrooms, offering both comfort and practicality. The spacious, updated kitchen showcases white cabinetry, stainless steel

  

  Angie Ordonez

  NextHome Realty Select

  (540) 384-4063

  133 Woodrow Rd, Winchester, VA 22602
• 

  Explore Winchester

• 

  

  

  /12

  $2,400 per month

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  21 S Stewart St Unit 4, Winchester, VA 22601

  Charming Remodeled 2-Bedroom Apartment Near Old Town Winchester!Enjoy the perfect mix of comfort and convenience in this beautifully remodeled 2 bedroom, 2 bathroom apartment located just steps from historic Old Town Winchester. This spacious unit features modern updates, in-unit laundry, and a fully fenced private yard—ideal for relaxing or entertaining. You'll also love the generous storage

  

  Frank Armstrong, IV

  Colony Realty

  (540) 781-1596

  21 S Stewart St Unit 4, Winchester, VA 22601
• 

  

  

  /46

  $430,000 Sold Aug 04, 2025

  • 1,612 Sq Ft
  • $267/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1991

  105 Tucks Cir, Winchester, VA 22602

  **We've received tremendous interest in this wonderful home and have set a DEADLINE of SUNDAY at 4 PM for all offers. We're looking forward to finding the next owner who will love and care for it just as much.** This charming, move-in ready rambler in Winchester offers a bright and open floor plan that feels instantly like home. Hardwood floors flow throughout the main living areas, while

  Brittney Hunt Pearson Smith Realty LLC

  105 Tucks Cir, Winchester, VA 22602
• 

  

  

  /37

  Est $427,003 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,052 Sq Ft

  222 E Piccadilly St, Winchester, VA 22601

  222 E Piccadilly St, Winchester, VA 22601
• 

  

  

  /71

  $1,250,000 Under Contract

  • Studio
  • 8,616 Sq Ft

  202 S Washington St, Winchester, VA 22601

  Back on the market due to NO fault of the Seller! Currently a single family home with a private “guest apartment”, but zoned multi-family with the potential for up to 4 units and potentially $4000.00+ in monthly rental income! Fantastic opportunity! The private guest suite currently has 2 bedrooms. The 3rd floor also has an additional 2 bedrooms, full bathroom and could laundry room that

  

  Lori Bales

  Keller Williams Realty

  (540) 917-5619

  202 S Washington St, Winchester, VA 22601
• 

  

  /8

  $1,150 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  2259 Papermill Rd Unit 4, Winchester, VA 22601

  This lower level apartment is an end unit. 1 bedroom,1 bath apartment is in a great location close to shopping and restaurants. NO Smoking, NO pets, NO Vaping. $30 application fee to cover credit and background check. Landlord is looking for around 700 credit score.

  

  Frank Armstrong, IV

  Colony Realty

  (540) 701-4871

  2259 Papermill Rd Unit 4, Winchester, VA 22601
• 

  

  /43

  $355,000 Sold Aug 04, 2025

  • 1,941 Sq Ft
  • $183/SF
  • 7 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2003

  120 Seabreeze Ln, Winchester, VA 22602

  Tastefully Updated & Spacious 3 Bedroom & 3.5 Bath End Unit Townhome Conveniently Located in the WINDSTONE Subdivision with Close Proximity to Schools, Shopping, Commuter Routes, Route 7 & 81. Fresh New Paint Throughout, Country Kitchen w/ Table Space & Sliding Glass Door Opens to the Deck, White Cabinetry, Pantry, Granite Counter Tops, Stainless Steel Appliances, Brand New Dishwasher, LVP

  Bill Fritz RE/MAX Executives

  120 Seabreeze Ln, Winchester, VA 22602
• 

  

  /14

  Not Listed For Sale

  0 Susquehanna Trail, Winchester, VA 22602

  0 Susquehanna Trail, Winchester, VA 22602
• 

  

  /46

  $995,000

  • 4 Beds
  • 2.5 Baths
  • 2,859 Sq Ft

  247 Mcguire Rd, Winchester, VA 22603

  Tucked away on a private 2.7-acre wooded lot, this stunning all-brick colonial has been fully renovated from top to bottom. Inside, 3/4" solid ash, 5"wide herringbone flooring flows throughout, accented by designer lighting, crown molding, and elegant chair rail trim. The chef’s kitchen is a true showstopper—featuring a massive island, striking white and gold appliances, and custom finishes. The

  

  Lori Bales

  Keller Williams Realty

  (540) 701-5541

  247 Mcguire Rd, Winchester, VA 22603
• 

  

  /11

  $1,700 per month

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

  44 S Loudoun St Unit 12, Winchester, VA 22601

  Discover the pinnacle of urban living in this charming 1-bedroom, 1-bathroom apartment located in the heart of the historic Winchester downtown walking mall. This comfortably spacious apartment merges the charm of its historic surroundings with the convenience of modern amenities, creating an exceptional rental choice. Perfectly positioned on the bustling Winchester walking mall, the apartment is

  

  Brock Harris

  Samson Properties

  (540) 584-1912

  44 S Loudoun St Unit 12, Winchester, VA 22601
• 

  

  /46

  $460,000 Sold Aug 04, 2025

  • 2,524 Sq Ft
  • $182/SF
  • 18 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1994

  131 Asbury Rd, Winchester, VA 22602

  Charming and updated Cape Cod in an established Winchester neighborhood with a fantastic commuter location just off Route 7. This 4-bedroom, 2.5-bath home features a main-level primary suite with a beautifully renovated bath, including a new walk-in shower and modern finishes. The kitchen offers updated stainless steel appliances, and the spacious upper-level bedrooms provide flexible living

  Chris Kershisnik EXP Realty, LLC

  131 Asbury Rd, Winchester, VA 22602
• 

  

  /43

  Est $714,242 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,569 Sq Ft

  121 Wales Ct, Winchester, VA 22602

  121 Wales Ct, Winchester, VA 22602
• 

  

  /13

  $749,000 Coming Soon

  • 3 Beds
  • 3.5 Baths
  • 5,802 Sq Ft

  1205 Caroline St, Winchester, VA 22601

  **Do Not Miss This One!**Professional Photos Coming Soon** Don’t miss this rare opportunity in the heart of Winchester! Offered for the first time since it was custom built in 2001, this stunning all-brick ranch sits on a beautifully landscaped and private 0.94-acre lot that feels like your own personal park. With nearly 3,000 square feet of thoughtfully designed space on the main level, this

  

  Jim Shebest

  Coldwell Banker Realty

  (540) 802-5378

  1205 Caroline St, Winchester, VA 22601
• 

  

  /13

  $1,700 - $2,400 per month

  The Local

  1 - 4 Beds

  230 Spring St, Winchester, VA 22601

  Modern designs, elegant finishes, and the most desirable amenities await you at the area’s newest apartment home living destination, the Local. Our Winchester apartments come in one, two, three, and four-bedroom floorplans, each featuring spacious and adaptable layouts. Various interior extras adorn them including an open floorplan concept, walk-in closets, in-unit washers/dryers, and more. As a

  230 Spring St, Winchester, VA 22601
• 

  

  /29

  $330,000 Sold Aug 01, 2025

  • 1,217 Sq Ft
  • $271/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  709 Panther Dr, Winchester, VA 22602

  Brand new and affordably priced! Built by Beiler and Company, this quality home offers an open layout with granite countertops, stainless steel appliances, and luxury vinyl plank flooring throughout. The smart split-bedroom design includes a private primary suite with dual closet and a walk-in shower. Nestled in a tranquil. wooded setting, this home also features a full walk-out basement ready to

  Lisa Gill ERA Oakcrest Realty, Inc.

  709 Panther Dr, Winchester, VA 22602
• 

  

  /20

  Est $445,348 Not Listed For Sale

  • 2 Beds
  • 4 Baths
  • 2,160 Sq Ft

  206 N Kent St, Winchester, VA 22601

  206 N Kent St, Winchester, VA 22601
• 

  

  /9

  $225,000 Under Contract

  • Land
  • 6 Acres
  • $37,563 per Acre

  Lot 3 Cedar Creek Grade, Winchester, VA

  Beautiful lot in a small neighborhood on the very desirable west side of Winchester off Cedar Creek Grade! Lot is already perked for an alternative septic system. This opportunity doesn’t come along often! Rolling hills with beautiful surroundings and views. The location is less than 10 minutes to grocery stores, downtown Winchester, or Winchester Medical Center. It’s also located within 2

  

  Lori Bales

  Keller Williams Realty

  (540) 974-1542

  Lot 3 Cedar Creek Grade, Winchester, VA
• 

  

  /110

  $3,950 per month

  • 4 Beds
  • 4 Baths
  • 4,881 Sq Ft
  • House for Rent

  101 Lynnehaven Dr, Winchester, VA 22602

  Gorgeous stately home that has been newly renovated to look like a model home! This home boasts over 5,000 finished square feet of spacious living space with a 2 car attached garage & all wooden and tile floors on all three levels. It features a gourmet kitchen with island, granite, backsplash and even a built in desk. The 2 story family room has a lovely gas fireplace with a 2 story stone

  Virginia Echols United Real Estate

  101 Lynnehaven Dr, Winchester, VA 22602
• 

  

  /47

  $525,000 Sold Aug 01, 2025

  • 1,865 Sq Ft
  • $282/SF
  • 42 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1941

  336 Miller St, Winchester, VA 22601

  This beautiful cottage, nestled on the very sought after Miller St, supplies the utmost convenience for what Winchester has to offer. From walking distance to eateries and Old Town entertainment, a quick drive to supermarkets all around and Handley High School just one street away! Supplying 3 bedrooms 2 1/2 bathrooms across three levels you can appreciate the character of an older home with

  Julie Teets Long & Foster Real Estate, Inc.

  336 Miller St, Winchester, VA 22601
• 

  

  /30

  Not Listed For Sale

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

  4255 Middle Rd, Winchester, VA 22602

  4255 Middle Rd, Winchester, VA 22602
• 

  

  /8

  $225,000 Under Contract

  • Land
  • 6 Acres
  • $40,761 per Acre

  Lot 6 Cedar Creek Grade, Winchester, VA

  Beautiful lot in a small neighborhood on the very desirable west side of Winchester off Cedar Creek Grade! Lot is already perked for an alternative septic system. This opportunity doesn’t come along often! Rolling hills with beautiful surroundings and views. The location is less than 10 minutes to grocery stores, downtown Winchester, or Winchester Medical Center. It’s also located within 2

  

  Lori Bales

  Keller Williams Realty

  (540) 974-1542

  Lot 6 Cedar Creek Grade, Winchester, VA
• 

  

  /22

  $1,799 - $2,231 per month

  Meadow Branch Luxury Apartments

  1 - 2 Beds

  424 Ridgewood Ln, Winchester, VA 22601

  Welcome to Meadow Branch, where luxury and convenience are standard. Our community offers beautiful 1,2 and 3 bedroom apartment homes. Community means convenience and at Meadow Branch, everything you need is nearby. We are conveniently located adjacent to Winchester Medical Center and 2 miles from Old Town Winchester.

  424 Ridgewood Ln, Winchester, VA 22601
• 

  

  /68

  $635,000 Sold Aug 01, 2025

  • 2,639 Sq Ft
  • $241/SF
  • 22 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2009

  800 Kennedy Dr, Winchester, VA 22601

  Welcome to 800 Kennedy Drive, a spacious Colonial by Richmond American Homes located in the desirable Rolling Hills Estates. This home offers three finished levels with a smart, open layout—perfect for everyday living and entertaining. The main level flows seamlessly from room to room, featuring beautiful hardwood floors and fresh new carpet throughout. The large family room, featuring a stone

  Cindy Greenya Keller Williams Realty

  800 Kennedy Dr, Winchester, VA 22601
• 

  

  /43

  Est $632,902 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,729 Sq Ft

  405 Lynnehaven Dr, Winchester, VA 22602

  405 Lynnehaven Dr, Winchester, VA 22602
• 

  

  /38

  $315,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  109 Lake Sever Dr, Winchester, VA 22603

  LOCATION! LOCATION! LOCATION! This is your chance to own your own home!! This turnkey rancher with 3 bedrooms and 2 full bathrooms sits on a quiet 1/4 acre fenced lot in Regency Heights! The first "wow" moment occurs when you pull in to see a spacious covered front porch with hanging baskets and a front porch swing ready for morning coffee and evening relaxation! Through the front door, the

  

  Tracey Scott

  Path Realty

  (540) 530-4171

  109 Lake Sever Dr, Winchester, VA 22603
• 

  

  /26

  $1,950 per month

  • 3 Beds
  • 1.5 Baths
  • 980 Sq Ft
  • House for Rent

  1309 Commerce St, Winchester, VA 22601

  This charming 3-bedroom, 1.5-bathroom home in the heart of Winchester offers comfort, character, and a prime location. Inside, you’ll find freshly painted walls, hardwood floors, new windows, a brand-new HVAC system, and updated electrical throughout. The home also features a basement with plenty of storage space and a washer and dryer for added convenience. The layout is both functional and

  James King RE/MAX Roots

  1309 Commerce St, Winchester, VA 22601
• 

  

  /52

  $424,990 Sold Aug 01, 2025

  • 1,889 Sq Ft
  • $225/SF
  • 20 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2025

  170 Munsee Cir, Winchester, VA 22602

  The Adams townhome design comes complete with 4 bedrooms, 3.5 bathrooms, and a 1 car garage. You will love the granite countertops, stainless steel appliances, and recessed lighting in the kitchen. Create the 4th bedroom of your dreams in the lower level bonus space! Other highlights include: Spacious 9 ft ceilings on the main level, over-sized kitchen island, upgraded cabinets, stainless

  Brooks Sears D R Horton Realty of Virginia LLC

  170 Munsee Cir, Winchester, VA 22602
• 

  

  /6

  Not Listed For Sale

  • Studio
  • 1,710 Sq Ft

  13 E North Ave, Winchester, VA 22601

  13 E North Ave, Winchester, VA 22601
• 

  

  /39

  $450,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 3,190 Sq Ft

  102 Shockey Cir, Winchester, VA 22602

  What a fantastic opportunity for 1-level living in a very desirable neighborhood within 3 minutes to downtown Winchester. This beautiful, all-brick home is located in Fairway Estates, also adjacent to the Winchester Country Club and golf course. It’s been very well-maintained of the years - move in ready and also happy to receive your updated touches. The full, large basement offers a guest

  

  Lori Bales

  Keller Williams Realty

  (540) 215-8959

  102 Shockey Cir, Winchester, VA 22602
• 

  

  /46

  $1,775 - $2,355 per month

  Stuart Hill

  1 - 3 Beds

  1981 Randolph Place, Winchester, VA 22601

  Nestled in the picturesque Shenandoah Valley in historic Winchester, Virginia, Stuart Hill Apartments combines convenience, a quality lifestyle, and warm, personalized service. Ideally situated just minutes from Historic Downtown Winchester, local shopping and dining, Shenandoah University, and the top-rated Winchester Medical Center, our community offers unparalleled access to everything you

  1981 Randolph Place, Winchester, VA 22601
• 

  

  /71

  $1,025,000 Sold Aug 01, 2025

  • 6,517 Sq Ft
  • $157/SF
  • 36 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 1863

  331 N Braddock St, Winchester, VA 22601

  This circa 1863 Italianate home is located in the heart of Winchester's historic district within a short walk to Handley Library and downtown. The home has been elegantly restored, blending timeless charm with modern comforts. The interior is restored to its original grandeur with high ceilings, hardwood floors, decorative moldings, and fireplaces in every room. Fully updated gourmet kitchen with

  John Schroth Colony Realty

  331 N Braddock St, Winchester, VA 22601
• 

  

  /29

  Est $524,480 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,151 Sq Ft

  442 Canyon Rd, Winchester, VA 22602

  442 Canyon Rd, Winchester, VA 22602
• 

  

  /45

  $475,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,466 Sq Ft

  106 Poe Dr, Winchester, VA 22602

  Welcome to This Lovely Richmond American Homes, Pearl Model. A Beautiful Single Family Home Located On An Oversized Corner Lot. 4 Bedroom, 3 Full Bathrooms. Gourmet Kitchen Boasts Quartz Counters, Stainless Steel Appliances, A Grand Island Housing the Farmhouse sink and quiet Dishwasher. An Spacious, Open Concept Main Level Featuring An Electric Fireplace. This Home Offers A Main Level Bedroom

  

  Adrian Blakeney

  EXP Realty, LLC

  (540) 805-8133

  106 Poe Dr, Winchester, VA 22602
• 

  

  /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
• 

  

  /51

  $350,000 Sold Jul 31, 2025

  • 1,445 Sq Ft
  • $242/SF
  • 44 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1961

  671 Fox Dr, Winchester, VA 22603

  ESTATE SALE..... "owner's pride" this cozy Ranch well taken care of, PROPERTY OFFERS....separate laundry room with back door entry, 13x13 family room, dining room with patio door going out onto a 10x19 covered deck, one bevel living, beautiful hardwood floors throughout, cozy brick fireplace in living room, pull down attic for extra storage, fenced backyard with dusk-to-dawn pole light, garage

  Wanda Garris Miller Century 21 Redwood Realty

  671 Fox Dr, Winchester, VA 22603
• 

  

  /60

  Est $407,579 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,300 Sq Ft

  152 Solara Dr, Winchester, VA 22602

  152 Solara Dr, Winchester, VA 22602
• 

  

  /51

  $699,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft

  881 Adams Rd, Winchester, VA 22603

  *Price Adjustment on this beautiful property!*Welcome to this exquisite 3-bedroom, 2-bath rancher nestled on nearly 9 private acres, offering 2,250 square feet of refined living space and unmatched serenity. From the moment you enter, you'll be captivated by the elegance of rich wood floors, 9-foot ceilings, and exquisite crown molding with wide baseboards throughout. The great room is a true

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 402-9684

  881 Adams Rd, Winchester, VA 22603
• 

  

  /50

  $1,785 - $3,144 per month

  The Lofts at Jubal Square

  1 - 3 Beds

  1864 Old Jube Square, Winchester, VA 22601

  Weve got it all at the Lofts at Jubal Square, the newest addition to the charming andhistoric Winchester cityscape. We offer a total commitment to better living, boasting largeapartments with loft and garage options, as well as amenities ideal for all those seeking anexceptional apartment lifestyle. Discover the Lofts at Jubal Square and discover what itmeans to live the good life.

  1864 Old Jube Square, Winchester, VA 22601
• 

  

  /75

  $1,071,134 Sold Jul 31, 2025

  • 5,000 Sq Ft
  • $214/SF
  • 1 Day On Market

  • 4 Beds
  • 5 Baths
  • Built 2006

  220 Anna Margaret Dr, Winchester, VA 22602

  Just minutes from town, this impressive all-brick residence in the sought-after Granville Estates offers the perfect blend of space, elegance, and versatility. Situated on nearly 3 acres, the home features over 5,000 square feet of thoughtfully designed living space, including a fully finished walkout basement and a detached 4-bay garage with an exceptional in-law suite.Step inside to a

  Bradley Comstock ERA Oakcrest Realty, Inc.

  220 Anna Margaret Dr, Winchester, VA 22602
• 

  

  /27

  Est $372,975 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  427 Washout Ln, Winchester, VA 22603

  427 Washout Ln, Winchester, VA 22603

Showing Results 1 - 40, Page 1 of 18