Winchester, VA Homes for Sale under $500,000

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  /47

  $399,000

  • 5 Beds
  • 3 Baths
  • 2,387 Sq Ft

  303 Pembridge Dr, Winchester, VA 22602

  Discover the potential of this charming split-level home nestled in the desirable Pembridge Heights community. This residence features five spacious bedrooms and three full bathrooms, providing ample room for relaxation and comfort. The large basement rec room adds versatility, perfect for a cozy family room, home office, or play area. Imagine hosting gatherings in the inviting living spaces,

  Rebecca Sims Century 21 Redwood Realty

  303 Pembridge Dr, Winchester, VA 22602
• 

  

  

  /35

  $459,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,905 Sq Ft

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

  The Adams II townhome features 1,905 sq. ft. of stylish and flexible living space, including 4 bedrooms, 3.5 bathrooms, and a 1-car rear-load garage. The gourmet kitchen is equipped with quartz countertops, stainless steel appliances, recessed lighting, a generous island, and sleek Duraform cabinetry. The lower-level bonus room offers endless possibilities—use it as a rec room, home office, or an

  D.R. Horton Builder

  1831 Reese Ct Unit 37025141, Winchester, VA 22601
• 

  

  

  /26

  $374,990

  New Construction

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

  HOMESITE 8 Monteith Dr, Winchester, VA 22601

  End of Row Townhome with 3 Bedrooms & 3.5 Bathrooms! All Three Levels Finished! Explore Winchester’s new luxury townhome community. This three level end unit home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with an extended island that seats four at counter

  DRB Homes Builder

  HOMESITE 8 Monteith Dr, Winchester, VA 22601
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  /83

  $437,750

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,327 Sq Ft

  131 Country Club Cir, Winchester, VA 22602

  Welcome to 131 Country Club Circle, a beautifully appointed all-brick masonry residence offering timeless construction and exceptional living space. This impressive home showcases tall ceilings and real hardwood flooring throughout the main level, creating a warm yet refined atmosphere. The thoughtfully designed layout includes a sunroom on the main level, ideal as a home office or flex space,

  Alexi Faraco Smart Realty, LLC

  131 Country Club Cir, Winchester, VA 22602
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  /15

  $220,000

  • Land
  • 5.39 Acres
  • $40,816 per Acre

  TBD (0) Cather Ln, Winchester, VA 22602

  Searching for the ideal place to build your dream home? This awesome 5.39 acre parcel delivers stunning views and a convenient location just minutes from town. Situated right off Rt 50 with easy access to Rt 37 and Interstate 81, you’ll be close to gas stations, restaurants, shopping, the hospital, and so much more—offering the perfect blend of peaceful country living and everyday convenience.

  Brian Doman Preslee Real Estate

  TBD (0) Cather Ln, Winchester, VA 22602
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  /49

  $320,000

  • 4 Beds
  • 2 Baths
  • 2,034 Sq Ft

  410 S Cameron St, Winchester, VA 22601

  Step into a home where timeless character and modern opportunity come together. This spacious property is filled with antique charm and unique details throughout.Featuring 4 bedrooms, 2 full bathrooms, and several versatile flex spaces, this home can easily adapt to your needs or offer increased income potential with a renovation. Enjoy the outdoor living opportunities with a private

  Heloisa Amar Samson Properties

  410 S Cameron St, Winchester, VA 22601
• 

  /2

  $249,000

  Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,257 Sq Ft

  1576 Brookland Terrace Unit 6, Winchester, VA 22602

  Coming Soon to the Market! Fantastic location! This spacious second-floor condo offers more square footage than most units in the community and features an open, light-filled layout, and durable flooring throughout with NO carpet. The thoughtfully designed floor plan includes a large living room, separate dining area, two generously sized bedrooms, and two full bathrooms. The primary suite offers

  Kim Hurst MarketPlace REALTY

  1576 Brookland Terrace Unit 6, Winchester, VA 22602
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  /29

  $275,000

  • 2 Beds
  • 1 Bath
  • 1,734 Sq Ft

  11 W Germain St, Winchester, VA 22601

  Back on the Market!...Beautifully located in the heart of Historic Winchester, this charming home offers 2 bedrooms, 1 full bath, and a versatile bonus room on the second floor-perfect for an office, guest space, or hobby room. Enjoy the convenience of being within walking distance to downtown Winchester's shops, restaurants, entertainment, and the famous Apple Blossom Festival festivities.

  Magnolia Halkowitz ERA Oakcrest Realty, Inc.

  11 W Germain St, Winchester, VA 22601
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  /24

  $359,990

  New Construction $5K PRICE DROP

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

  12 Monteith Dr, Winchester, VA 22601

  3 Level Townhome with 3 Bedrooms! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! 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 beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen

  DRB Homes Builder

  12 Monteith Dr, Winchester, VA 22601
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  /28

  $420,000

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  775 Pack Horse Rd, Winchester, VA 22603

  Completely remodeled and move-in ready, this charming property at 775 Pack Horse Road in Frederick County, VA offers the perfect blend of modern updates and peaceful country living. Situated on a picturesque setting, the home has been thoughtfully renovated throughout, featuring updated finishes, refreshed interiors, and attention to detail in every room. Enjoy the convenience of a detached

  Amanda Slate Keller Williams Realty

  775 Pack Horse Rd, Winchester, VA 22603
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  /55

  $365,000

  • 3 Beds
  • 2 Baths
  • 2,280 Sq Ft

  617 Fox Trail, Winchester, VA 22602

  Looking for a mountain top getaway? This adorable rancher is it with 3 bedrooms, 2 full baths. Updated kitchen w/stainless appliances and tons of light. Back deck is an oasis with a gazebo and a place to sip morning coffee and overlook the incredible wooded lot. This home has an extra building lot as well (lot is to the left of the home)! Full basement with family room, rec room w/pool table and

  Traci Shoberg Samson Properties

  617 Fox Trail, Winchester, VA 22602
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  /28

  $482,990

  New Construction $17K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,216 Sq Ft

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

  The Glendale is a new construction home plan featuring 2,216 square feet of living space, 4 bedrooms, 3.5 baths and a 2-car garage. The Glendale gives you the features you’re looking for at the price you want! You’ll immediately feel at home as you enter into the spacious family room. This living space flows nicely into the eat-in kitchen which highlights a peninsula island overlooking the family

  D.R. Horton Builder

  137 Seminole Dr Unit 39403232, Winchester, VA 22602
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  /41

  $489,990

  New Construction $45K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,284 Sq Ft

  100 Brockham Ct, Winchester, VA 22602

  This move-in-ready home includes pre-selected upgrades and a new-construction warranty. Welcome to this beautifully crafted new home by a respected local builder, offering almost 2,300 square feet of thoughtfully designed living space in the desirable Sovereign Village community. The inviting, open-concept main level features a spacious kitchen with a large island, perfect for gathering and

  Marisa Varley ERA Oakcrest Realty, Inc.

  100 Brockham Ct, Winchester, VA 22602
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  /3

  $275,000

  • Land
  • 5.79 Acres
  • $47,496 per Acre

  LOT 1 - Handley Dr, Winchester, VA 22603

  Spring Valley Estates. A rare opportunity to find a 5-Acre lots within 5 minutes of downtown Winchester and the Valley Health Medical Center. James Wood High School and Apple Pie Elementary within a mile of this lot. Fully built lot with approved perc on file. Buyer can buy the lot and build their dream house or for future investment purposes. This corner lot is cleared with existing road

  JP Carr Merrifield Realty, LLC

  LOT 1 - Handley Dr, Winchester, VA 22603
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  /26

  $399,990

  New Construction

  • 3 Beds
  • 4 Baths
  • 2,026 Sq Ft

  116 Swansong Place, Winchester, VA 22603

  Exceptional Value – Brand-New 3-Bedroom Townhome for Summer Move-In!Don’t miss this incredible opportunity to own a beautifully crafted new construction townhome in the newest section of Snowden Bridge.Designed for modern living, this home features oak stairs with upgraded railings and durable luxury vinyl plank flooring throughout the main level. The bright, stylish kitchen boasts white

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  116 Swansong Place, Winchester, VA 22603
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  /33

  $420,000

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft

  104 Lloyds Rd, Winchester, VA 22602

  This charming ranch-style home is filled with warmth and sophistication. Step inside to discover an inviting atmosphere, accentuated by exquisite interior features such as chair railings and crown moldings. The thoughtfully designed space features three spacious bedrooms and two luxurious baths, including a primary suite with a whirlpool tub and separate shower. Rich wood floors create a cozy

  Val Nicole Clark Realty FC, LLC

  104 Lloyds Rd, Winchester, VA 22602
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  /17

  $475,000

  • Land
  • 89.87 Acres
  • $5,285 per Acre

  0 Shockeysville Rd Unit VAFV2041652, Winchester, VA 22603

  Approximately 90-acre wooded parcel offering abundant space for recreation, hunting, and enjoying nature, with Little Brush Creek bordering the property. This private retreat features approximately 2,500 feet of creek frontage and has been recently surveyed. The property is accessed by frontage on Shockyeville Road or established easement and offers a peaceful, remote setting while still being

  Brandi Marcum Pearson Smith Realty, LLC

  0 Shockeysville Rd Unit VAFV2041652, Winchester, VA 22603
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  /22

  $369,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,000 Sq Ft

  HOMESITE 44 Shuoner Ct, Winchester, VA 22602

  110 SHUONER Ct – Model Home | We Have spec homes Summer 2026 Delivery AvailableSt. Paul TBB | 4 BR | 3.5 BA | 1-Car Garage | Finished Lower Level + Larger Deck Beautiful wooded homesites available!Offering up to 2,000 sq. ft. of modern, open-concept living — customize your home the way you like, or keep everything as-is at this price, including a 4th bedroom. Home Highlights Open-concept

  Jimmy Thomas New Home Star Virginia, LLC

  HOMESITE 44 Shuoner Ct, Winchester, VA 22602
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  /37

  $329,000

  • 3 Beds
  • 2 Baths
  • 2,075 Sq Ft

  129 Jalapa Trail, Winchester, VA 22602

  Perched high above the Shenandoah Valley in the sought-after mountain community of Shawneeland, 129 Jalapa Trail offers a rare opportunity to embrace the beauty, tranquility, and adventure of mountain living. Surrounded by mature trees and breathtaking long-range views, this private retreat invites you to wake up each morning to spectacular sunrises and endless vistas stretching across the valley

  Vivian Garcete Samson Properties

  129 Jalapa Trail, Winchester, VA 22602
• 

  /2

  $215,000

  • Land
  • 40,075 Sq Ft
  • $233,696 per Acre

  0 7 Building Lots In Shawneeland Unit VAFV2032844, Winchester, VA 22602

  REDUCED by $20k! CALLING ALL BUILDERS!! 7 BUILDING LOTS for $215,000 (being sold as a bundle) located in Shawneeland in Frederick County, VA. . Perc approved certification letter, plat and sewer docs on file for each lot. The lots range in size from 0.40-0.92 acres. Potential home sites for permanent home or weekends and vacations. Enjoy hiking, fishing, swimming in the lake, nature walks and

  Caroline W. Barb, REALTOR Jim Barb Realty, Inc.

  0 7 Building Lots In Shawneeland Unit VAFV2032844, Winchester, VA 22602
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  /11

  $249,900

  • Land
  • 7.1 Acres
  • $35,197 per Acre

  384 Frog Hollow Rd, Winchester, VA 22603

  7 scenic acres with no restrictions and endless potential. Offering over 450' feet of road frontage, this beautiful parcel features a gentle slope and a thoughtfully prepared layout for future development. A partially cleared area is ready for a potential homesite, with an additional cleared septic location already in place. Current owner is in the process of obtaining well and septic

  Jennifer Sacco RE/MAX Roots

  384 Frog Hollow Rd, Winchester, VA 22603
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  /49

  $395,000

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  1355 Perry Rd, Winchester, VA 22602

  This beautifully remodeled home showcases quality and attention to detail from the moment you step inside. The kitchen has been completely transformed with abundant cabinetry, generous counter space, and brand-new stainless steel appliances, creating both style and functionality. Throughout the home, you will find new flooring, doors, trim, and fresh paint, giving every room a clean, modern feel.

  Roxane Morrison NextHome Realty Select

  1355 Perry Rd, Winchester, VA 22602
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  /47

  $319,900

  • 3 Beds
  • 1.5 Baths
  • 1,242 Sq Ft

  936 Allen Dr, Winchester, VA 22601

  Charming, beautifully maintained ranch home in a well-established Winchester neighborhood! Meticulously maintained and thoughtfully updated over the years, this special property was built in 1965 by Kingsberry Homes using the sought-after Belden model. Lovingly cared for by just one family since its construction, the home even comes with the original architectural floor plans provided by the

  Jody Elson Dream Real Estate

  936 Allen Dr, Winchester, VA 22601
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  /47

  $349,000

  • 3 Beds
  • 2.5 Baths
  • 1,566 Sq Ft

  101 Locust Ave, Winchester, VA 22601

  Welcome to 101 Locust Avenue in the heart of Winchester on a spacious corner lot! This solid brick ranch home offers 3 bedrooms, 2.5 bathrooms, and comfortable one-level living with additional space in the lower level. The bright and spacious living room serves as the centerpiece of the home, featuring a large bay window that fills the space with natural light. On the main level there are three

  Angela Duncan MarketPlace REALTY

  101 Locust Ave, Winchester, VA 22601
• 

  

  /15

  $405,990

  New Construction

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

  112 Coriander Way, Winchester, VA 22603

  The three-level Skyline model masterfully combines a traditional exterior with a contemporary, open-concept floor plan. On the main level, you’ll find an expansive living room, bathed in natural light from numerous windows, flows effortlessly into the dining area and kitchen. The kitchen is designed with an L-shaped countertop and an island that borders the dining room. A cozy nook serves as a

  Brookfield Residential Builder

  112 Coriander Way, Winchester, VA 22603
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  /40

  $315,000

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

  406 Raccoon Dr, Winchester, VA 22602

  Back on market, no fault of seller! Seller has replaced main beam and has replaced several logs. Tucked away in the peaceful Wilde Acres neighborhood, this beautiful home offers the perfect balance of privacy, character, and comfort. Inside, you’re welcomed by stunning wide-plank heart pine flooring that brings warmth and timeless character to the living space. A newly updated shower adds a

  STEVEN REESE EXP REALTY LLC - STAFFORD

  406 Raccoon Dr, Winchester, VA 22602
• 

  

  /35

  $365,000

  $30K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,656 Sq Ft

  330 Wardensville Grade, Winchester, VA 22602

  MOTIVATED SELLER! Experience the perfect blend of peaceful country charm and modern convenience in this beautifully remodeled 3-bedroom, 1.5-bath home offering comfortable two-level living and true move-in-ready appeal. Sitting on 1.38 acres, this home features all new windows, siding, and roof installed in 2022, along with a HVAC system installed in 2021 with warranty coverage for added peace of

  Stacey Rowe Real Broker LLC

  330 Wardensville Grade, Winchester, VA 22602
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  /46

  $345,000

  $15K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  307 1/2 E Piccadilly St, Winchester, VA 22601

  Welcome to 307 1/2 E Piccadilly Street, a charming detached home offering comfort, convenience, and character in the heart of Winchester. Ideally located just minutes from Old Town Winchester, the Walking Mall, local restaurants, shopping, parks, and commuter routes, this property places you close to downtown amenities while still offering the privacy and feel of a standalone home. Inside, you’ll

  Nate Crandell HoneyWay

  307 1/2 E Piccadilly St, Winchester, VA 22601
• 

  

  /58

  $429,900

  Open Sat 11AM - 1PM

  • 4 Beds
  • 2.5 Baths
  • 1,714 Sq Ft

  101 Charlton Rd, Winchester, VA 22602

  Welcome to 101 Charlton Road, a charming 4-bedroom, 2.5-bath Cape Cod situated on a desirable corner lot. This well-maintained home features a main-level primary suite and beautiful hardwood floors throughout the main living areas. The spacious kitchen is equipped with stainless steel appliances, a center island, breakfast nook, and flows seamlessly into the separate dining room and inviting

  RoxAnn Grimes RE/MAX Roots

  101 Charlton Rd, Winchester, VA 22602
• 

  

  /18

  $388,190

  New Construction $2K PRICE INCREASE

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

  1805 Sloane St, Winchester, VA 22601

  1805 Sloane St. is an attractive new 3 level townhome with full brick front in Winchester, VA for August move-in. Free Deck for first 3 homebuyers! Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances. The

  D.R. Horton Builder

  1805 Sloane St, Winchester, VA 22601
• 

  

  /19

  $406,190

  New Construction $2K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 1,923 Sq Ft

  1813 Sloane St, Winchester, VA 22601

  1813 Sloane St. is an attractive new 3 level townhome with full brick front in Winchester, VA for August move-in. Included Deck for first 3 homebuyers! Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances.

  D.R. Horton Builder

  1813 Sloane St, Winchester, VA 22601
• 

  

  /29

  $259,900

  • 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

  $369,900

  • Land
  • 11.49 Acres
  • $32,193 per Acre

  Lot 1 Tavistock Dr, Winchester, VA 22602

  Beautiful 11.49 acre Lot, approved for 3 bedroom perk, Tavistock Estates one of the last lots remaining! A gorgeous 7 minute drive from town through farmland and full of mountain views. Excellent neighborhood, road access is great, level lot among 'horse country' estates! Build your dream mini equestrian farm or just enjoy peace, quiet, and serenity with the genius of a quick commute into town!

  Gillian Greenfield Coldwell Banker Premier

  Lot 1 Tavistock Dr, Winchester, VA 22602
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  /39

  $374,000

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,809 Sq Ft

  328 Longview Ave, Winchester, VA 22601

  Price Reduced $15,000! Highly Motivated Seller! Welcome to this meticulously maintained, move-in-ready ranch home located within Winchester City limits. Perfectly situated on a premium, near-half-acre lot (.46 acres) off Papermill Road, this property offers the ultimate blend of city convenience and peaceful privacy with no backyard neighbors. Property Highlights:Flexible Layout: Features

  Kelly Bauer Coldwell Banker Premier

  328 Longview Ave, Winchester, VA 22601
• 

  

  /19

  $399,900

  New Construction Open Sat 11AM - 2PM $10K PRICE INCREASE

  • 3 Beds
  • 3 Baths
  • 1,914 Sq Ft

  107 Pinto Trail, Winchester, VA 22602

  I AM DONE AND READY! Split foyer low in community and flat lot with easy access out of subdivision (mailboxes, community trash drop off and exit very close to home).

  Jim Thomson Realty ONE Group Old Towne

  107 Pinto Trail, Winchester, VA 22602
• 

  

  /16

  $250,000

  $110K PRICE DROP

  • Studio
  • 1,249 Sq Ft

  45 and 45 1/2 Race St, Winchester, VA 22601

  INVESTORS - at this price you have a fabulous income property with an 11% cap rate. Here's the math - two units renting at $1,250 = $30,000 income. Subtract taxes and insurance = approximately $28,600. This is a great starter property for those looking to build a real estate portfolio or add to an existing one. Both apartments were completely rehabbed last year - new wiring and plumbing, new

  Teri Domanski Your Home Sold Guaranteed Realty - East LLC

  45 and 45 1/2 Race St, Winchester, VA 22601
• 

  

  /61

  $435,000

  • 3 Beds
  • 2.5 Baths
  • 1,634 Sq Ft

  113 Wertland Place, Winchester, VA 22602

  Luxury upgrades and thoughtful custom features make this exceptional end-unit townhome a standout in the desirable Winchester Landing 55+ community. With over $80,000 in owner-added upgrades, this beautifully appointed residence offers 3 bedrooms, 2.5 baths, and the convenience of main-level living with premium finishes throughout. The spacious main-level primary suite provides a private retreat,

  Laura White ERA Oakcrest Realty, Inc.

  113 Wertland Place, Winchester, VA 22602
• 

  

  /29

  $369,900

  $19K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,263 Sq Ft

  224 Hawk Trail, Winchester, VA 22602

  Welcome home to this charming retreat nestled in the Shawneeland community of Winchester, Virginia. This beautifully reimaged rambler has been fully remodeled. The 3-bedroom, 2-bathroom home offers the perfect blend of modern finishes and relaxed mountain community living – ready for you to move-in and enjoy! Step outside and breathe it all in. A delightful front porch sets the tone the moment

  Joelle Graham Weichert, REALTORS

  224 Hawk Trail, Winchester, VA 22602
• 

  

  /26

  $380,000

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft

  140 Graywolf Trail, Winchester, VA 22602

  This fully finished 1,840 sq. ft. home offers the space, updates, and setting buyers are looking for. Featuring a fully finished walkout-level basement, newer hardwood flooring, updated bathrooms, fresh paint, a beautiful rock fireplace, stainless steel appliances, quartz countertops, and two spacious decks, this home is move-in ready and perfect for enjoying the peaceful surroundings of Shawnee

  Rick Guthrie Keller Williams Realty

  140 Graywolf Trail, Winchester, VA 22602
• 

  

  /36

  $350,000

  New Construction $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft

  513 Pheasant Dr, Winchester, VA 22602

  Welcome to this newly built colonial in Wilde Acres situated on 1/4 acre lot nestled among the trees and surrounded by a wall made of native stone. Upon entry, enjoy the open living area and wood floors which make the space warm and comfortable. The galley kitchen offers ample counterspace and new stainless steel appliances. The convenient main level full bath also has hookup for stackable washer

  Ismael Carino MarketPlace REALTY

  513 Pheasant Dr, Winchester, VA 22602

Showing Results 161 - 200, Page 5 of 6