Winchester, VA Homes for Sale under $500,000

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  /21

  $269,000

  • 3 Beds
  • 1.5 Baths
  • 1,280 Sq Ft

  321 N Kent St, Winchester, VA 22601

  Wonderful opportunity to own in downtown Winchester! Walking distance to the Old Town Mall restaurants, shopping, the library and more. Easy access to Rt. 7 and 81. The main level has a nice open floor plan, consisting of kitchen, dining and living areas. The main level also features a half bath and bonus room, perfect for an office or den. Upstairs you will find three bedrooms, full bathroom and

  Amy Capitano MarketPlace REALTY

  321 N Kent St, Winchester, VA 22601
• 

  

  

  /33

  $353,990

  New Construction

  • 3 Beds
  • 4 Baths
  • 1,669 Sq Ft

  136 Swansong Place, Winchester, VA 22603

  Brand New, townhome with 3 finished levels, is under construction and will be ready for you to call home this Summer! With builder incentives available, there is no reason to wait to make this the next place you call home!Backing to open space in the newest section of Snowden Bridge, this home will be in close proximity to all of the newest amenities. Natural light flows through the kitchen

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  136 Swansong Place, Winchester, VA 22603
• 

  

  

  /40

  $389,900

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,838 Sq Ft

  106 Plantation Dr, Winchester, VA 22602

  Charming 4-bedroom, 2-bath rancher situated on a .34-acre lot with mature trees providing shade in both the front and back yards. Enjoy outdoor living with a fenced backyard, rear deck, and storage shed. Inside, the vaulted-ceiling living room with a wood-burning fireplace creates a bright and inviting gathering space. The walkout lower level offers excellent flexibility with a spacious family

  Sheila Pack RE/MAX Roots

  106 Plantation Dr, Winchester, VA 22602
• 

  

  

  /51

  $480,000

  • 4 Beds
  • 2 Baths
  • 2,268 Sq Ft

  1306 Vanceright Cir, Winchester, VA 22601

  Filled with storybook charm and timeless character, this enchanting cottage-style home is much larger than it appears! Newly refinished hardwood floors flow throughout the home, blending warmth and elegance with everyday comfort. The updated kitchen offers modern convenience while maintaining the home's inviting charm. The partially finished basement provides flexible space for a family room,

  Julie Teets ERA Oakcrest Realty, Inc.

  1306 Vanceright Cir, Winchester, VA 22601
• 

  

  

  /41

  $370,000

  $80K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,625 Sq Ft

  110 Rugby Place, Winchester, VA 22603

  ** Bank approved Short sale price ** opportunity with a significant price reduction—bring all offers. Welcome to 110 Rugby—a striking 3-bedroom, 2.5-bath home designed with space, style, and modern comfort in mind. Hardwood floors, a dramatic two-story foyer, recessed lighting, and a statement fireplace set the tone throughout. The open-concept kitchen features quartz countertops, warm wood

  Brandon Hatchett Samson Properties

  110 Rugby Place, Winchester, VA 22603
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  /35

  $295,000

  $5K PRICE DROP

  • 2 Beds
  • 3 Baths
  • 1,028 Sq Ft

  902 Enfield Dr, Winchester, VA 22602

  Will Walraven Realty One Group Key Properties

  902 Enfield Dr, Winchester, VA 22602
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  /54

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 1,702 Sq Ft

  209 W Cedarmeade Ave, Winchester, VA 22601

  Ideal concept for one-level living with an open floor plan that still provides areas for private spaces. Lovely hardwood floors tie the plan together, from the cozy fireplace to warm winter evenings, to the shady screened porch to catch the Spring and Fall breezes. Well maintained neighborhood near services, shopping, schools and access to commuting thoroughfares. Newer roof, new rear fence, new

  Dallas Croft Samson Properties

  209 W Cedarmeade Ave, Winchester, VA 22601
• 

  

  /20

  $409,900

  New Construction $10K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,660 Sq Ft

  123 Killbuck Trail, Winchester, VA 22602

  Under construction and same home completed 211 Inca TrailPremium Finishes: Enjoy a builder-upgraded interior featuring gleaming hardwood floors throughout the entire home (including all bedrooms) and elegant tile in all bathrooms.Gourmet Kitchen: Equipped with upgraded cabinetry, sleek granite countertops, a central island, and a sunny breakfast nook.Modern Layout: An airy, open floor

  Jim Thomson Realty ONE Group Old Towne

  123 Killbuck Trail, Winchester, VA 22602
• 

  

  /40

  $299,900

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

  110 Brookland Ct Unit 10, Winchester, VA 22602

  Welcome home to this one-of-a-kind, fully renovated penthouse condo that has been transformed right down to the studs! Offering luxury finishes rarely found at this price point, this stunning residence is unlike anything else available in Frederick County under $300,000. Every detail has been thoughtfully updated, including a new gas furnace, new HVAC system, new flooring throughout, neutral

  Traci Shoberg Samson Properties

  110 Brookland Ct Unit 10, Winchester, VA 22602
• 

  

  /46

  $372,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  ADAMS Plan at Retreat at Winding Creek - Townhomes, Winchester, VA 22602

  The 1,889 sq. ft. Adams townhome design comes complete with 4 bedrooms, 3.5 bathrooms, and a 1-car garage. You will love the granite counter tops, stainless steel appliances, and recessed lighting in the kitchen. Create the rec room, home office or 4th bedroom of your dreams in the lower level bonus space! The Adams comes with a 12'x10' deck off the rear of the home, perfect for outdoor

  D.R. Horton Builder

  137 Seminole Dr Unit 36203787, Winchester, VA 22602
• 

  

  /23

  $419,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,094 Sq Ft

  126 Swansong Place, Winchester, VA 22603

  Exceptional value for a 4‐bedroom END‐UNIT townhome is ready for move‐in! Brand‐new construction offers modern style and comfort with oak stairs with upgraded railings and durable LVP flooring throughout the main level. Backing to open space in the newest section of Snowden Bridge, this spacious home includes a flexible entry‐level bedroom with full bath, a bright open‐concept main living area,

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  126 Swansong Place, Winchester, VA 22603
• 

  

  /15

  $319,000

  $11K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  211 Fair Ln, Winchester, VA 22603

  Beautifully newly remodeled ranch-style home set on a spacious 0.62-acre flat lot. This move-in ready residence features a fully updated interior with a modern kitchen complete with granite countertops, brand-new stainless steel appliances, and all-new cabinetry. The home showcases rich hardwood flooring throughout and has been thoughtfully upgraded with new windows and a newer metal roof for

  Kenny Ritenour Samson Properties

  211 Fair Ln, Winchester, VA 22603
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  /37

  $379,900

  • 2 Beds
  • 1.5 Baths
  • 1,186 Sq Ft

  711 E Cork St, Winchester, VA 22601

  This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door.

  Marco Novillo Spring Hill Real Estate, LLC.

  711 E Cork St, Winchester, VA 22601
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  /55

  $409,999

  $40K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,850 Sq Ft

  1105 Henry Dr, Winchester, VA 22602

  Home offers nearly 3000 sqft of finished living space that has Luxury Vinyl flooring through out both levels (absolutely no carpet) that features 4 bedrooms and 2.5 baths situated on over a 1/2 acre (.61) of ground. Upon entering you will find an open floor plan that encompasses a large living room and dining room with canned lighting then pours into the large eat in kitchen (new appliances) that

  James Amick RE/MAX Roots

  1105 Henry Dr, Winchester, VA 22602
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  /42

  $349,900

  $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,532 Sq Ft

  117 Coralyrose Ct, Winchester, VA 22602

  4 Years Young and Move-In Ready! This beautifully maintained, like-new home is nestled in a small, private community on the desirable east side of Frederick County. Enjoy an unbeatable location with easy access to I-81 and Route 7, just minutes from Jim Barnett Park, Shenandoah University, shopping, dining, and Historic Downtown Winchester. Plus, you're only approximately 1 hour and 15 minutes

  Vanessa Couture Samson Properties

  117 Coralyrose Ct, Winchester, VA 22602
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  /47

  $439,934

  • 4 Beds
  • 2 Baths
  • 1,868 Sq Ft

  187 Village Ct, Winchester, VA 22602

  Great Location! Move-In Ready! No HOA! Updated Split Foyer with Oversized 2-Car Garage!!! | Fresh Paint from Top to Bottom | All New Carpet, Granite Counters & Stainless Steel Appliances In Kitchen | Gleaming Hardwoods & New LVP on the Main Level | 3 BR & 2 BA Upstairs | 4th BR + Large Rec Room & Laundry Room in Basement, |Deck(as-is) off the Main Level overlooks treed back yard | Covered Front

  Bob Caines RE/MAX Distinctive Real Estate, Inc.

  187 Village Ct, Winchester, VA 22602
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  /27

  $474,490

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,168 Sq Ft

  113 Trellis View Ln, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Freeport floorplan is a thoughtfully designed villa blending style and functionality in a single-level open layout and finished loft. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen,

  D.R. Horton Builder

  113 Trellis View Ln, Winchester, VA 22602
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  /33

  $352,999

  $7K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,218 Sq Ft

  544 Bluebird Trail, Winchester, VA 22602

  Escape to the peaceful mountain community of Wilde Acres and discover this charming 3-bedroom, 2-bath home situated on a spacious 1⁄2-acre lot. This well-maintained property offers privacy, tranquility, and numerous recent upgrades throughout. The entire home has been freshly repainted, featuring brand-new flooring in the foyer and basement landing, all new locks, and new door handles on every

  Dona Shiley ERA Oakcrest Realty, Inc.

  544 Bluebird Trail, Winchester, VA 22602
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  /32

  $359,500

  New Construction Coming Soon

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

  604 Gatling Dr, Winchester, VA 22602

  Welcome to this beautiful 3-bedroom, 2-bathroom split-level home, a brand-new build nestled on a spacious 0.26-acre lot in the Mountain Falls Park community. Enjoy a warm welcome with a cozy covered porch. Inside, the home features luxury vinyl plank flooring throughout, providing a modern, durable finish. The kitchen is a chef's delight, with stainless steel appliances, premium shaker-style

  Sheila Pack RE/MAX Roots

  604 Gatling Dr, Winchester, VA 22602
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  /25

  $275,000

  $45K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,222 Sq Ft

  317 Fairview Ave, Winchester, VA 22601

  Price improvement - bring offers! Fully Renovated SFH in Historic Winchester! Prime location. Just minutes from charming Historic Downtown Winchester featuring local shops, restaurants, entertainment, and more! Beautifully Updated throughout. This charming home offers bright, inviting living spaces with modern finishes and thoughtfully updates designed for comfortable everyday living. w Just Move

  Donna Lutkins Real Broker, LLC

  317 Fairview Ave, Winchester, VA 22601
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  /2

  $365,000

  • 4 Beds
  • 2.5 Baths
  • 2,678 Sq Ft

  719 National Ave, Winchester, VA 22601

  A true Federal‐style gem, this solid brick home offers the chance to restore a piece of architectural history. Rich with original craftsmanship, it features high ceilings, original hardwood floors, solid wood doors and trim, and a beautiful covered front porch—timeless details that showcase the home’s enduring character. Designed with good bones and a layout that adapts to many visions, this

  Windy Harris Hunt Country Sotheby's International Realty

  719 National Ave, Winchester, VA 22601
• 

  

  /20

  $274,900

  • Land
  • 6.84 Acres
  • $40,190 per Acre

  202 Cedar Grove Rd, Winchester, VA 22603

  Calling investors and outdoors enthusiasts: This property is close to town with a large shop, and a potential small home after renovations! The vacant home is in need of love and repairs, but has electric, water from a private well, and a permitted septic rated for 2 bedrooms. The large shop has electric and an adjacent H2O hydrant, as well as a loft for extra space. Backing up to quiet

  Ryan Foster Keller Williams Realty

  202 Cedar Grove Rd, Winchester, VA 22603
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  /39

  $320,000

  • 3 Beds
  • 1 Bath
  • 1,988 Sq Ft

  528 Battle Ave, Winchester, VA 22601

  Adorable Cape Cod in the heart of Winchester! Beautifully appointed with hardwood floors, signature arched doorways from that era adding tons of charm to this lovely home. Two main floor bedrooms, renovated and updated bath, living room with gas fireplace and brick surround, kitchen with brand new gas range, expanded space perfect for dining and entertaining with doors to the front and rear

  Beckwith Bolle Carter Braxton Preferred Properties

  528 Battle Ave, Winchester, VA 22601
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  /52

  $290,000

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft

  700 Tomahawk Trail, Winchester, VA 22602

  Welcome to this charming ranch-style home situated on a spacious .44-acre corner lot in the desirable Shawneeland community. Thoughtfully updated and well maintained, this home offers comfort, functionality, and modern touches throughout. The kitchen has been enhanced with a newly added pantry (2026) making everyday living and entertaining effortless. The primary bedroom features French doors

  Lindsey Gomes Real Broker, LLC

  700 Tomahawk Trail, Winchester, VA 22602
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  /32

  $380,000

  • 3 Beds
  • 2.5 Baths
  • 1,497 Sq Ft

  120 Pomo Ln, Winchester, VA 22602

  Welcome to The Retreat at Winding Creek, where modern style, low-maintenance living, and a prime Winchester location come together beautifully. Investors ** First Time Buyers ** Down Sizers ** Less than a year old and in move in condition! This nearly new end-unit garage townhome offers 3 spacious bedrooms, 2.5 baths, and the added privacy and natural light that only an end unit can provide. 3

  Sue Smith Compass

  120 Pomo Ln, Winchester, VA 22602
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  /26

  $369,990

  New Construction $5K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  13 Monteith Dr, Winchester, VA 22601

  3 Level Townhome with Deck! The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home with backing to trees for added privacy and peaceful views. Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room. This

  DRB Homes Builder

  13 Monteith Dr, Winchester, VA 22601
• 

  

  /15

  $394,990

  New Construction

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

  111 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

  111 Heirloom Way, Winchester, VA 22603
• 

  

  /20

  $365,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft

  813 Crow Dr, Winchester, VA 22602

  This newly constructed 3-bedroom, 2.5-bath Colonial offers approximately 1,512 finished square feet, a 1-car garage, and a thoughtfully designed floor plan with quality finishes throughout. The main level features an open-concept layout with luxury vinyl plank flooring, a spacious family room, dining area, and a well-appointed kitchen with upgraded countertops and pantry. A convenient half bath

  Abby Walters Preslee Real Estate

  813 Crow Dr, Winchester, VA 22602
• 

  

  /39

  $484,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,906 Sq Ft

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

  The Deerfield is a thoughtfully designed home with four bedrooms and two-and-a-half baths. The kitchen features a walk-in pantry and a breakfast island, which includes a sink, making it perfect for food preparation, and has plenty of room for stools, so you can entertain. The kitchen looks out over the open-concept dining area and great room. All four bedroom are upstairs along with the Laundry

  D.R. Horton Builder

  137 Seminole Dr Unit 36203782, Winchester, VA 22602
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  /21

  $213,000

  $22K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 970 Sq Ft

  127 Geronimo Trail, Winchester, VA 22602

  Nestled in the serene Shawneeland community, this charming ranch-style home offers a perfect blend of comfort and tranquility. Set on a generous 1.92-acre lot, the property features a gently sloping landscape adorned with mature trees, creating a peaceful retreat from the hustle and bustle of everyday life. This 3-bedroom, 1-bathroom home invites you to unwind and make lasting memories. The

  Steve DuBrueler Coldwell Banker Premier

  127 Geronimo Trail, Winchester, VA 22602
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  /16

  $249,900

  • Land
  • 1 Acre
  • $249,900 per Acre

  Lot 36 Lake Serene Dr, Winchester, VA 22603

  Lake Serene Winchester Va. Don’t miss this rare opportunity to own the last available build-able lot in peaceful, secluded Lake Serene, a private, established lake community quietly tucked away, yet only 10 minutes from Old Town Winchester! You will never find an opportunity like this to enjoy the peace and tranquility of waterfront living with the added bonus of being only a few miles from

  Mark Jenkins Rappahannock Real Estate, LLC.

  Lot 36 Lake Serene Dr, Winchester, VA 22603
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  /38

  $409,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  Adams Plan at Abrams Crossing at Meadow Branch, Winchester, VA 22601

  The Adams I townhome offers 1,889 sq. ft. of thoughtfully designed living space, featuring 4 bedrooms, 3.5 bathrooms, and a convenient 1-car front-load garage. The modern kitchen showcases quartz countertops, stainless steel appliances, a spacious island, recessed lighting, and upgraded cabinets. Enjoy the flexibility of a finished lower-level bonus space—perfect for a rec room, home office, or

  D.R. Horton Builder

  1831 Reese Ct Unit 37025140, Winchester, VA 22601
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  /32

  $399,900

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,764 Sq Ft

  114 Williamson Rd, Winchester, VA 22602

  Welcome home to this spacious, beautifully maintained all-brick residence on the east side of Winchester. Combining timeless curb appeal with low-maintenance, energy-efficient construction, this home offers over 2,000 square feet of comfortable one-level living, including a bright and inviting sunroom. Inside, you'll find a thoughtfully designed floor plan featuring formal living and dining rooms

  Dave Spence RE/MAX Roots

  114 Williamson Rd, Winchester, VA 22602
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  /33

  $415,000

  • 4 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  123 Etnam St, Winchester, VA 22602

  Well-maintained colonial available in one of Winchester’s premier subdivisions, Pembridge Heights. The main level features a formal dining room just off the foyer, perfect for family gatherings, which flows into the eat-in kitchen with LVP flooring, stainless steel appliances, a tile backsplash, custom wood cabinetry, and access to the deck overlooking a semi-flat backyard with a koi pond. The

  Paul Sneeringer Keller Williams Realty

  123 Etnam St, Winchester, VA 22602
• 

  

  /23

  $459,990

  New Construction

  • 2 - 3 Beds
  • 1 Bath
  • 1,564+ Sq Ft

  Hemingway Plan at Hiatt Pointe at Snowden Bridge - 55+ Garden Homes Collection, 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

  105 Wagtail Ln Unit 36578850, Winchester, VA 22603
• 

  

  /22

  $378,260

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  118 Shuoner Ct, Winchester, VA 22602

  Summer 2026 Delivery Available St. Paul Townhome TBB | 3 BR | 2.5 BA | 1-Car Garage | Finished Lower Level Beautiful wooded homesites available! Offering up to 2,000 sq. ft. of modern, open-concept living designed for today's lifestyle. Home Highlights Open-concept main level — perfect for entertaining family and friends Granite countertops Stainless steel appliances Luxury vinyl plank flooring

  Jimmy Thomas New Home Star Virginia, LLC

  118 Shuoner Ct, Winchester, VA 22602
• 

  

  /61

  $475,000

  $25K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,686 Sq Ft

  179 Woodridge Ln, Winchester, VA 22603

  Spacious Ranch Home with In-Law Suite Potential on 1.58 Acres Discover the perfect blend of space, comfort, and convenience in this ranch home offering over 3,700 finished square feet of living space. The main level features more than 2,100 square feet above grade, including 3 bedrooms, 2 full bathrooms, a spacious kitchen, beautiful hardwood floors, and an attached 2-car garage plus another

  Traci Shoberg Samson Properties

  179 Woodridge Ln, Winchester, VA 22603
• 

  

  /10

  $280,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 817 Sq Ft

  580 York Ave, Winchester, VA 22601

  This charming bungalow in the heart of the City of Winchester has already been beautifully renovated, offering the perfect blend of classic charm and modern living. Featuring 2 cozy bedrooms and a full bathroom, the home is designed with comfort and functionality in mind. Enjoy an updated kitchen and bathrooms, new appliances, and central A/C for a fresh, modern feel. The newly added front deck

  Yoselin Mejia The Vasquez Group LLC

  580 York Ave, Winchester, VA 22601
• 

  

  /41

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft

  703 S Loudoun St, Winchester, VA 22601

  Located in the heart of Winchester’s Historic District, this remarkable property offers a rare opportunity to own a piece of the city’s rich architectural heritage just moments from vibrant Old Town Winchester. Blending timeless character with flexible living options, the home showcases classic historic charm paired with thoughtful updates that support today’s lifestyle. Inside the main

  John Ginty Samson Properties

  703 S Loudoun St, Winchester, VA 22601
• 

  

  /26

  $295,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 984 Sq Ft

  110 Duwamish Trail, Winchester, VA 22602

  Charming and Move-In Ready Ranch in a Peaceful Setting!Welcome home to this beautifully refreshed single-level ranch nestled on a spacious, tree-lined lot. This inviting home features a bright and functional layout with updated finishes throughout. The kitchen offers grey cabinetry, granite countertops, and stainless steel appliances, creating a clean and modern space perfect for everyday

  Tina Jacobin Main Street Realty

  110 Duwamish Trail, Winchester, VA 22602

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