Studio to 3 Bedroom Homes for Sale in Winchester, VA

• 

  

  

  /24

  $265,000

  • 2 Beds
  • 1 Bath
  • 882 Sq Ft

  204 Shenandoah Ave, Winchester, VA 22601

  Great opportunity to own this 2-bed, 1-bath Winchester City charmer that sits just minutes from Shenandoah University and the Old Town walking mall. Main level living with a bright comfortable living area, an eat-in kitchen home that includes a bonus room providing flexible space for an office, playroom, fitness area, or guest room, central air and the convenience of an in-home washer & dryer

  Janet Flaherty Keller Williams Realty

  204 Shenandoah Ave, Winchester, VA 22601
• 

  

  

  /53

  $654,000

  • Studio
  • 3,511 Sq Ft

  1400 Valley Ave, Winchester, VA 22601

  Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful wood floors, tall ceilings, fireplace, sunroom, and a stunning staircase that adds timeless character. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you can rent out both

  Danielle Spriggs Real Broker LLC

  1400 Valley Ave, Winchester, VA 22601
• 

  

  

  /19

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft

  369 Charles St, Winchester, VA 22601

  This two-story home offers classic charm with a covered front porch, fenced backyard, and upper-level balcony. Located just minutes from downtown, 369 Charles Street features a recently updated kitchen with modern cabinetry, granite countertops, and stainless steel appliances. The main level features updated flooring, while the upstairs level provides access to a private, covered balcony. Two

  Marisa Varley ERA Oakcrest Realty, Inc.

  369 Charles St, Winchester, VA 22601
• 

  

  

  /37

  $396,500

  • 3 Beds
  • 1.5 Baths
  • 1,416 Sq Ft

  31 W Whitlock Ave, Winchester, VA 22601

  Charming Home Near Handley High School – Move-In Ready! Welcome to this beautifully updated home in a fantastic downtown location—just a short walk to shops, restaurants, and all that the vibrant city center has to offer. This property features a converted garage that now serves as a versatile studio space, perfect for a home office, art studio, or guest suite. Enjoy a spacious, fenced-in

  Meridee Powars Link Realty Services LLC

  31 W Whitlock Ave, Winchester, VA 22601
• 

  

  

  /27

  $414,990 New Construction

  • 3 Beds
  • 1.5 Baths
  • 2,433 Sq Ft

  119 Heirloom Way, Winchester, VA 22603

  This stunning two-level villa boasts a modern open concept design that seamlessly connects living spaces for an inviting and spacious feel. The main level features a living room that opens effortlessly to the dining area, creating a perfect space for entertaining and family gatherings. The expansive rear kitchen includes an L-shaped layout with an eating bar and an island with additional bar

  Brookfield Residential Builder

  119 Heirloom Way, Winchester, VA 22603
• 

  

  /26

  $299,990

  • 3 Beds
  • 1 Bath
  • 1,205 Sq Ft

  627 Watson Ave, Winchester, VA 22601

  CLASSIC CHARM MEETS CONTEMPORARY COMFORT IN THIS FANTASTIC DUPLEX UNIT! This charming Winchester duplex unit seamlessly blends timeless character with modern conveniences, offering the perfect balance of historic flair and contemporary living. Nestled just minutes from the vibrant heart of downtown Winchester, this inviting property combines an unbeatable location with a thoughtfully-updated

  Kristin Crosby Samson Properties

  627 Watson Ave, Winchester, VA 22601
• 

  $389,880 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,966 Sq Ft

  109 Boone Ct, Winchester, VA 22602

  Introducing the St. Paul, one of Maronda’s latest townhome designs.The St. Paul offers a range of 1,966 to 1,989 square feet of living space, including 3 to 4 bedrooms, 2.5 to 3.5 bathrooms, and a spacious 1-car garage. This new design offers plenty of personalization opportunities to fit your family’s unique needs.On the first floor of the home, you will find a spacious, open-concept floor plan.

  Maronda Homes Builder

  109 Boone Ct, Winchester, VA 22602
• 

  

  /22

  $315,000

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

  140 Mccormick Cir Unit 403, Winchester, VA 22602

  Motivated Sellers! Bring all offers.Nearly-new 55+ condominium located in Winchester Landing, offering comfort, convenience, and style just minutes from town. Step inside to an open floor plan filled with natural light, featuring a bright and modern kitchen with quartz countertops, a center island with sink, and sleek lighting that makes entertaining a breeze. The oversized primary suite is a

  Sharon Farinholt Realty ONE Group Old Towne

  140 Mccormick Cir Unit 403, Winchester, VA 22602
• 

  

  /22

  $235,000

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

  157 Brookland Terrace Unit 11, Winchester, VA 22602

  Top-Floor Gem with Vaulted Ceilings, Modern Upgrades & Quick Seller Move-Out!Welcome home to this bright and airy 2-bedroom, 2-bath top-level condo that perfectly blends comfort, style, and convenience — and offers buyers the advantage of quick seller vacancy for a smooth and flexible closing! Step inside and be greeted by soaring vaulted ceilings and abundant natural light streaming through

  Becky Green Samson Properties

  157 Brookland Terrace Unit 11, Winchester, VA 22602
• 

  

  /34

  $500,000

  • 3 Beds
  • 2.5 Baths
  • 1,978 Sq Ft

  236 Miller St, Winchester, VA 22601

  Charming 3-Bedroom/ 2.5 Bath Colonial just blocks from Old Town Winchester, offering easy access to dining, entertainment, and shopping! This home offers classic charm and everyday comfort with a covered front porch, fenced backyard, and rear patio—perfect for relaxing or entertaining. A 2-car detached garage (with electric), off-street parking, and attractive landscaping enhance both

  Sheila Pack RE/MAX Roots

  236 Miller St, Winchester, VA 22601
• 

  

  /43

  $459,000

  • 3 Beds
  • 2 Baths
  • 2,648 Sq Ft

  1332 Ramseur Ln, Winchester, VA 22601

  Welcome home to a rare find in the Mews of Meadow Branch - this exceptional all-brick exterior condo offering 3 bedrooms and 2 full baths. Rich hardwood floors flow throughout the home. The primary bedroom includes a cozy fireplace perfect for relaxing evenings. Updated appliances, such as washer, dryer, refrigerator, stove and microwave. Enjoy the ease of your own private elevator within the

  James King RE/MAX Roots

  1332 Ramseur Ln, Winchester, VA 22601
• 

  

  /17

  $330,000

  • 3 Beds
  • 1 Bath
  • 1,237 Sq Ft

  117 W Oates Ave, Winchester, VA 22601

  This charming bungalow, nestled in the heart of the Arthur C Oates Estate, offers a delightful blend of comfort and community. Built in 1953, this home features 3 cozy bedrooms, 1 full bathrooms, and an upstairs loft perfect for relaxation. The inviting kitchen is equipped with essential appliances, including a single oven and refrigerator, making meal preparation a breeze. The unfinished

  Jeffrey Konrady Realty ONE Group Old Towne

  117 W Oates Ave, Winchester, VA 22601
• 

  

  /45

  $950,000

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

  Lot 12 Keval Gyan Way, Winchester, VA 22603

  Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house; it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of single-level living in this immaculate,

  Jim Thomson Realty ONE Group Old Towne

  Lot 12 Keval Gyan Way, Winchester, VA 22603
• 

  

  /64

  $669,409 New Construction

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

  120 Magpie Ln, Winchester, VA 22603

  MOVE IN READY HOME AND OFFERING UP TO $15,000 IN CLOSING COST ASSISTANCE WITH USE OF VAN METRE'S PREFERRED LENDER/TITLE COMPANY.55+ Active Adult living just got better in Winchester Virginia with Hiatt Pointe, Van Metre Homes newest gated community. You have to come see for yourself these stunning new single family and villa homes. Hiatt Pointe is a resort style community and has it all

  Cynthia Butler Samson Properties

  120 Magpie Ln, Winchester, VA 22603
• 

  

  /22

  $549,990 Open Sun 12PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,658 Sq Ft

  Homesite 195 Malbec, Winchester, VA 22602

  Welcome to Abrams Pointe, featuring new single-family homes in an established Winchester neighborhood, complete with wooded cul-de-sac homesites. The Avalon is a beautiful 3-bedroom, 2 bath home with up to 2,538 square feet of living space. This single-family home design features main-level living with an open floor plan, highlighted by a spacious great room, a light-filled kitchen, and a

  Dorelba Estrada New Home Star Virginia, LLC

  Homesite 195 Malbec, Winchester, VA 22602
• 

  

  /22

  $300,000

  • 3 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  534 N Kent St, Winchester, VA 22601

  Just minutes from the downtown walking mall, this single family home offers three bedrooms, stainless steel appliances and granite countertops, a great yard, off street parking, and a front porch. The home comes with an electric car charger usable for all brands.

  Katie Landi Jordan Samson Properties

  534 N Kent St, Winchester, VA 22601
• 

  

  /46

  $599,900

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft

  289 Westview Dr, Winchester, VA 22603

  Welcome to your private contemporary retreat at 289 Westview Drive in Winchester, VA! This truly exceptional property offers the ultimate escape, situated on over 13 magnificent acres with gorgeous mature trees, stunning views, and unparalleled peace and quiet. Step inside the sun-filled main level, featuring an open layout that seamlessly connects the living room, dining room, and kitchen.

  Dan Whitacre Colony Realty

  289 Westview Dr, Winchester, VA 22603
• 

  

  /29

  $289,900

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  1125 Conway St, Winchester, VA 22601

  Check out this Very Cute Bungalow in Winchester City! It has a Brand NEW Roof, Freshly Painted throughout, NEW kitchen/hall/bath flooring, NEW Stainless Steel Refrigerator, Restored deck, and Lovely Hardwood! Cozy with 2 Bedrooms and 1 Bath. Surely to be perfect for the first time Home Buyer! Great Location close to shopping & restaurants. Great for commuters as well as it's on the East side of

  Jodi Costello ERA Oakcrest Realty, Inc.

  1125 Conway St, Winchester, VA 22601
• 

  

  /12

  $598,990 Open Sun 12PM - 4PM

  • 3 Beds
  • 2 Baths
  • 3,056 Sq Ft

  24 Williamson Rd, Winchester, VA 22602

  Welcome to Abrams Pointe, featuring new single-family homes in an established Winchester neighborhood, complete with wooded cul-de-sac homesites. The Drexel Floorplan is a spacious and versatile single-family home designed to suit a variety of lifestyles. With up to 3,213 finished square feet, the Drexel offers generous living space that can be customized to meet your needs. It features

  Dorelba Estrada New Home Star Virginia, LLC

  24 Williamson Rd, Winchester, VA 22602
• 

  

  /71

  $449,900

  • 3 Beds
  • 2.5 Baths
  • 2,012 Sq Ft

  4403 Back Mountain Rd, Winchester, VA 22602

  Nestled on two private wooded acres, 4403 Back Mountain Road in Winchester, VA offers a peaceful country retreat with no HOA or restrictions. Built in 2001, this traditional Colonial-style home features approximately 2,012 square feet of comfortable finished living space, including three bedrooms and two and a half baths . The walk-out basement provides excellent storage and potential for future

  RoxAnn Grimes RE/MAX Roots

  4403 Back Mountain Rd, Winchester, VA 22602
• 

  

  /23

  $514,929 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,195 Sq Ft

  119 Wagtail Ln, Winchester, VA 22603

  MOVE IN READY HOME AND OFFERING UP TO $15,000 IN CLOSING COST ASSISTANCE WITH USE OF VAN METRE'S PREFERRED LENDER/TITLE CO. 55+ Active Adult living just got better in Winchester Virginia with Hiatt Pointe, Van Metre Homes newest gated community. You have to come see for yourself this stunning new villa home. Hiatt Pointe is a resort style community and has it all clubhouse, swimming pool, hot

  Cynthia Butler Samson Properties

  119 Wagtail Ln, Winchester, VA 22603
• 

  

  /8

  $349,900 New Construction

  • 2 Beds
  • 1 Bath
  • 1,064 Sq Ft

  131 Hawk Trail, Winchester, VA 22602

  Offering $10,000 towards purchaser closing costs with acceptable offer. Pictures as of 12-17-25. Drywalled as of 12-20-25. Comcast/Xfinity available on this street. New plan on almost 1/3 of acre! Affordable new home close to town with full unfinished basement (two double windows and walkout exit with ruff in for future bath) for future needs. Upgrades include: Hardwood floors throughout (sanded

  Jim Thomson Realty ONE Group Old Towne

  131 Hawk Trail, Winchester, VA 22602
• 

  

  /19

  $349,900

  • 3 Beds
  • 3 Baths
  • 1,850 Sq Ft

  1619 Tomahawk Trail, Winchester, VA 22602

  Discover the best value for square footage in this stunning 3 bed, 3 bath home. Perched on over half an acre with panoramic mountain views. Enjoy an open floor plan, vaulted kitchen, hardwood floors throughout the main level & bedrooms, and a huge finished rec room. Builder bonuses include granite counters, kitchen island, and upgraded cabinets. Side-load 2-car garage & paved drive. A must-see!

  Jim Thomson Realty ONE Group Old Towne

  1619 Tomahawk Trail, Winchester, VA 22602
• 

  

  /23

  $449,900

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

  104 Primrose Place, Winchester, VA 22602

  Moe Gahche Long & Foster Real Estate, Inc.

  104 Primrose Place, Winchester, VA 22602
• 

  

  /11

  $269,000

  • 2 Beds
  • 1.5 Baths
  • 1,116 Sq Ft

  518 Yorktowne Place, Winchester, VA 22601

  This exquisite end-of-row townhouse, underwent a major renovation in 2025, offers a perfect blend of modern luxury and timeless comfort. With two spacious bedrooms and one and a half elegantly appointed bathrooms, this home is designed for both relaxation and entertaining. Step inside to discover a gourmet kitchen that will inspire your culinary adventures. Featuring upgraded granite countertops,

  Brandon Pifer Pifer Realty, LLC

  518 Yorktowne Place, Winchester, VA 22601
• 

  

  /4

  $849,999

  • 3 Beds
  • 2 Baths
  • 2,488 Sq Ft

  Lot 11 Keval Gyan Way, Winchester, VA 22603

  Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house (new PIN OAK model); it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of single-level living

  Jim Thomson Realty ONE Group Old Towne

  Lot 11 Keval Gyan Way, Winchester, VA 22603

Showing Results 121 - 146, Page 4 of 4