Winchester County VA Homes for Sale

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  $670,000

  • 3 Beds
  • 2 Baths
  • 2,450 Sq Ft

  1400 Gordon Place, Winchester, VA 22601

  ONE LEVEL LIVING AND BRAND NEW ROOF in The Downs at Meadowbranch, a sought after community convenient to shopping, medical center, and Old Town Winchester. OPEN SATURDAY 1PM-3PM! Expansive all-brick home offers 3 bedrooms, 2 bathrooms, attached 2-car garage and 2450 square feet of living space! What's better than an idyllic 1/5 acre corner lot... how about an idyllic 1/5 acre corner lot you don't

  Stacy Rodgers Berkshire Hathaway HomeServices PenFed Realty

  1400 Gordon Place, Winchester, VA 22601
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  $385,000

  Open Sun 1PM - 3PM $15K PRICE DROP

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

  1853 Rosser Ln, Winchester, VA 22601

  Welcome to easy one-level living in Willow Lawn Cottages, a popular 55+ community in Winchester! This well-maintained home has been freshly painted and offers 2 bedrooms and 2 full bathrooms. The open floor plan feels bright and spacious, with vaulted ceilings, plenty of natural light, and luxury vinyl plank flooring throughout. The kitchen includes granite countertops, updated cabinets,

  Sarena Baker Realty FC, LLC

  1853 Rosser Ln, Winchester, VA 22601
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  /97

  $1,100,000

  • 6 Beds
  • 6 Baths
  • 6,789 Sq Ft

  1030 Breckinridge Ln, Winchester, VA 22601

  Welcome to this inviting, beautifully maintained 6-bedroom, 4-full-bathroom, 2-half-bathroom all-brick home in the desirable Meadow Branch subdivision in Winchester, Virginia. Offering over 6,000 square feet of finished living space, this impressive residence combines generous room sizes, timeless construction, exceptional storage, and comfortable living spaces designed for both everyday life and

  Joleen Haymaker Samson Properties

  1030 Breckinridge Ln, Winchester, VA 22601
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  /59

  $519,900

  $55K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  660 Beehive Way, Winchester, VA 22601

  Enjoy city living in this spacious and light-filled home featuring 5 bedrooms and 3.5 baths. Fresh new carpeting has been installed on the upper level and in the family room, complemented by hardwood floors throughout the main living areas.The kitchen is equipped with stainless steel appliances, double ovens, and a center island—perfect for cooking and entertaining. Formal living and

  Traci Shoberg Samson Properties

  660 Beehive Way, Winchester, VA 22601
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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
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  /32

  $471,000

  • 3 Beds
  • 2.5 Baths
  • 2,260 Sq Ft

  421 Longview Ave, Winchester, VA 22601

  A must see property! This is a beautifull well kept colonial house with 3 bedrooms, 2 full bath and 1 half bath. The basement is unfinish but is ready to be build. As you enter the main level, you will see a nice welcoming livingroom, diningroom and beautiful granite countertops in the kitchen, with stainless steel appliances and high effitiency washer and dryer to the side. From the kitchen you

  Valentin Bonilla Samson Properties

  421 Longview Ave, Winchester, VA 22601
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  /36

  $376,990

  New Construction

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

  HOMESITE 3 Monteith Dr, Winchester, VA 22601

  ***OFFERING UP TO $9,500 IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home backing to trees for added privacy and peaceful views.

  Brittany Newman DRB Group Realty, LLC

  HOMESITE 3 Monteith Dr, Winchester, VA 22601
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  /19

  $329,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,576 Sq Ft

  305 Smalts Cir, Winchester, VA 22601

  Currently under construction, this beautiful new home is scheduled for a December move-in, giving you the opportunity to enjoy a brand-new home without the wait in a walkable location, just steps from Old Town!This home features 3 beds, 2.5 baths, quartz countertops, stainless steel appliances, finished rec room and more! Plus, enjoy all closing costs paid with use of NVR Mortgage!

  Ryan Homes Builder

  305 Smalts Cir, Winchester, VA 22601
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  $425,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,030 Sq Ft

  413 Superior Ave, Winchester, VA 22601

  ***Sellers offering $5k credit towards a mini-split -or- for closing cost assistance.*** This beautiful rancher sits on 0.38 acres with an expansive, level backyard that is fully fenced and shaded by gorgeous, mature trees. A large deck spans the back of the home and incorporates a charming stock-tank plunge pool with liner and filtration system, creating a fantastic space for relaxing and

  Steph Mitchell Samson Properties

  413 Superior Ave, Winchester, VA 22601
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  /25

  $250,000

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  1125 Conway St, Winchester, VA 22601

  Welcome to 1125 Conway Ave, a charming bungalow in Winchester City that's move-in ready and full of character! This cozy 2-bedroom, 1-bath home features beautiful hardwood floors and numerous recent updates, including a new roof, fresh interior paint, kitchen remodel, hallway and bathroom flooring, and a new stainless steel refrigerator. The deck has also been restored, providing a great spot to

  Curtis Siever NextHome Realty Select

  1125 Conway St, Winchester, VA 22601
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  /29

  $284,900

  • 2 Beds
  • 2.5 Baths
  • 1,540 Sq Ft

  5 E Hart St, Winchester, VA 22601

  Enjoy the convenience of downtown Winchester living in this charming 2-bedroom, 2-bath townhome, ideally located within walking distance of restaurants, shopping, school games and more. The main level features a comfortable living area and an eat-in kitchen with doors leading to a beautiful Trex deck, perfect for morning coffee, grilling or relaxing at the end of the day. Upstairs, both bedrooms

  Leah Marabella Realty ONE Group Old Towne

  5 E Hart St, Winchester, VA 22601
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  /26

  $354,990

  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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  $299,900

  • 4 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  1 E Hart St, Winchester, VA 22601

  Enjoy downtown Winchester living with plenty of flexibility! This 4-bedroom, 2.5-bath townhome offers a functional layout in a convenient location close to restaurants, shopping, schools, Handley games, and all that downtown Winchester has to offer. The main level features a comfortable living area, kitchen with eat-in space, and access to a beautiful Trex deck overlooking the fully fenced

  Leah Marabella Realty ONE Group Old Towne

  1 E Hart St, Winchester, VA 22601
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  /39

  $369,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,578 Sq Ft

  1414 S Braddock St, Winchester, VA 22601

  PRICE REDUCED $10,000. Come Check out this charming Cape Cod home in Winchester City, built in 1950 and beautifully renovated in 2026, offers a perfect blend of classic character and modern convenience. With 2 spacious bedrooms and 2 full bathrooms, including a luxurious walk-in shower, this residence is designed for comfort. The heart of the home features a bright kitchen equipped with stainless

  Richard Kozlowski Long & Foster Real Estate, Inc.

  1414 S Braddock St, Winchester, VA 22601
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  $479,000

  Open Sun 4PM - 6PM $51K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,505 Sq Ft

  108 Morgan St, Winchester, VA 22601

  OPEN HOUSE 09/27/2026 FROM 4:00 PM - 6:00 PMWelcome to this charming historic home in Old Town Winchester. This spacious 3-bedroom Colonial blends timeless character with modern comfort in a convenient downtown location. Thoughtfully updated with today’s buyer in mind, this inviting residence offers upgraded amenities while preserving its classic appeal.Ideally situated within

  Stacey Rowe Real Broker LLC

  108 Morgan St, Winchester, VA 22601
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  $359,000

  • 3 Beds
  • 1.5 Baths
  • 1,710 Sq Ft

  812 Appleseed Ct, Winchester, VA 22601

  Nestled on a quiet cul-de-sac surrounded by mature trees in the highly desirable Orchard Hills Subdivision with no HOA fees or restrictions, this traditional all-brick home features 3 bedrooms, 1.5 bathrooms, a 2-car driveway, and three beautifully finished levels of move-in-ready living space. From the tree-lined sidewalks and charming street lighting, you are welcomed onto a main level boasting

  Feletia Sharples Realty FC, LLC

  812 Appleseed Ct, Winchester, VA 22601
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  /26

  $374,990

  New Construction

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

  HOMESITE 8 Monteith Dr, Winchester, VA 22601

  Open House this Saturday & Sunday from 2-4 PM!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

  DRB Homes Builder

  HOMESITE 8 Monteith Dr, Winchester, VA 22601
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  $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
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  /31

  $265,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,734 Sq Ft

  11 W Germain St, Winchester, VA 22601

  BACK ON THE MARKET -NO FAULT OF THE SELLERS -Step inside this historic home in the heart of Winchester and discover a home that offers far more than you might expect. Generously sized rooms provide plenty of space to relax, or enjoy your favorite hobbies, while a light-filled sunroom creates the perfect spot for morning coffee, reading, plants, or simply slowing down and enjoying the

  Magnolia Halkowitz ERA Oakcrest Realty, Inc.

  11 W Germain St, Winchester, VA 22601
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  /58

  $399,000

  • 3 Beds
  • 1.5 Baths
  • 1,725 Sq Ft

  633 Pennsylvania Ave, Winchester, VA 22601

  OPEN HOUSE SATURDAY SEPTEMBER 19TH 1:30 TO 3:30PM Charming 1932 Craftsman Near Downtown Winchester! Step into this classic 1932 Craftsman home, where timeless historic character perfectly meets modern updates. Stunning original craftsman style windows in every room. Boasting an abundance of original woodwork and original wood floors throughout, this home radiates warmth, style, and craftsmanship.

  Karen O'Hare Colony Realty

  633 Pennsylvania Ave, Winchester, VA 22601
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  /19

  $393,190

  New Construction

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

  644 Arden Ct, Winchester, VA 22601

  644 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for September move-in. 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

  644 Arden Ct, Winchester, VA 22601
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  /26

  $300,000

  • 2 Beds
  • 1 Bath
  • 1,097 Sq Ft

  310 Bellview Ave, Winchester, VA 22601

  Classic Winchester charm awaits at 310 Bellview Avenue! This inviting Cape Cod combines character, convenience, and plenty of opportunity to make the space your own. Inside, you’ll find hardwood floors, comfortable living areas, two main-level bedrooms, a full bathroom, and an additional half bath upstairs. A full basement offers extra storage and future possibilities, while the detached one-car

  Cindy Greenya Keller Williams Realty

  310 Bellview Ave, Winchester, VA 22601
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  /51

  $364,900

  • 3 Beds
  • 3 Baths
  • 2,064 Sq Ft

  802 Appleseed Ct, Winchester, VA 22601

  NO HOA-City of Winchester on cul-de-sac with a spacious yard that feels like a private oasis.Charming and inviting townhome offering an unusual and versatile four-level floor plan with wonderful indoor and outdoor living spaces! The main level features a welcoming living room with a beautiful bay window, fireplace and built-in shelving, along with a dining room accented by crown molding and chair

  Darcy Amburn Colony Realty

  802 Appleseed Ct, Winchester, VA 22601
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  /47

  $329,900

  $10K PRICE INCREASE

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

  936 Allen Dr, Winchester, VA 22601

  Charming, beautifully maintained all-brick ranch home at 936 Allen Drive! Built in 1965 by Kingsberry Homes using the sought-after Belden model, this special property has been lovingly cared for by one family since its construction and even includes the original architectural floor plans. Inside, the move-in-ready home offers stunning hardwood floors and an enclosed carport seamlessly converted

  Jody Elson Dream Real Estate

  936 Allen Dr, Winchester, VA 22601
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  /18

  $250,000

  $25K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 740 Sq Ft

  135 S Kent St Unit 202, Winchester, VA 22601

  Step into the charm of Historic Downtown Winchester with this beautifully renovated Urban Lofts Condominium, where history and modern living come together. Located in a home built in 1825, this unique property is just a short stroll to Winchester's favorite restaurants, boutique shopping, coffee shops, museums, and downtown events.Renovated in 2021, the condo offers stylish updates while

  Sharon Farinholt Realty ONE Group Old Towne

  135 S Kent St Unit 202, Winchester, VA 22601
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  /2

  $350,000

  • 3 Beds
  • 1.5 Baths
  • 1,507 Sq Ft

  1048 Woodland Ave, Winchester, VA 22601

  Nestled in a charming neighborhood, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this brick beauty exudes timeless appeal while providing modern living spaces that cater to today's lifestyle. With 1,507 square feet of thoughtfully designed space, this residence features three cozy bedrooms and one and a half bathrooms, making it an ideal

  Shane Bowman RE/MAX Roots

  1048 Woodland Ave, Winchester, VA 22601
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  /39

  $384,990

  New Construction

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

  HOMESITE 126 Monteith Dr, Winchester, VA 22601

  The most affordable townhomes in Winchester City! END OF ROW Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home 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 ***OFFERING UP TO $5K IN

  DRB Homes Builder

  HOMESITE 126 Monteith Dr, Winchester, VA 22601
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  /25

  $177,000

  $12K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 896 Sq Ft

  313 Avon Ct, Winchester, VA 22601

  Newly remodeled 2-level townhouse located in a quiet, established neighborhood! This move-in ready home features a bright, sun-filled kitchen with a spacious eat-in dining area, two generously sized bedrooms, and 1.5 bathrooms. Enjoy the convenience of one assigned parking space directly in front of the home, plus a guest parking pass for unmarked spaces.Relax on the private rear deck or

  Ms. Sophia Alam AMN Realty, LLC.

  313 Avon Ct, Winchester, VA 22601
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  /2

  $389,000

  Coming Soon Oct 6

  • 2 Beds
  • 1 Bath
  • 1,216 Sq Ft

  116 E Cork St, Winchester, VA 22601

  A RARE DOWNTOWN GEM IN THE HEART OF HISTORIC WINCHESTER! Discover the charm and convenience of this beautifully restored circa-1900 row house, ideally located just one block from Winchester’s iconic Walking Mall. Enjoy an exceptional walkable lifestyle with an array of restaurants, coffee shops, boutiques, and nightlife right outside your door. Thoughtfully renovated from top to bottom, this home

  Karl Achstetter Keller Williams Realty

  116 E Cork St, Winchester, VA 22601
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  $449,000

  • 4 Beds
  • 1.5 Baths
  • 1,932 Sq Ft

  420 W Cork St, Winchester, VA 22601

  Discover the perfect blend of historic charm and modern convenience at 420 W Cork Street. This captivating four-level brick home offers 4 bedrooms and 1.5 baths, boasting beautiful hardwood floors, gorgeous trim and plenty of space for you and yours. The main level offers a spacious living room, dining room and kitchen. Upstairs you will find 4 sizable bedrooms and a full bath. The top level is a

  Dan Whitacre Colony Realty

  420 W Cork St, Winchester, VA 22601
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  /46

  $329,000

  $31K 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
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  /57

  $599,990

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,386 Sq Ft

  112 Worsham Terrace, Winchester, VA 22602

  Situated on a desirable cul-de-sac homesite backing to community open space, this thoughtfully designed home offers the perfect blend of comfort and functionality. The main level features a spacious owner's suite, formal dining room, laundry room, powder room, and an open-concept kitchen overlooking the living and dining areas. The kitchen includes quartz countertops, an island with seating,

  Victoria Clark D R Horton Realty of Virginia LLC

  112 Worsham Terrace, Winchester, VA 22602
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  /51

  $349,000

  $30K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 2,592 Sq Ft

  2055 Cidermill Ln, Winchester, VA 22601

  PRICE IMPROVEMENT. OPEN HOUSE SATURDAY, SEPTEMBER 19TH 11:00 AM TO 1:00PM. Welcome home to this beautifully maintained 3-bedroom, 2-full-bath/2 half bath, end-of-row townhouse! Perfectly situated in a highly desirable, family-friendly neighborhood, step inside to find gleaming hardwood floors and large, sunlit rooms that offer plenty of space to live and entertain. The heart of the home features

  Karen O'Hare Colony Realty

  2055 Cidermill Ln, Winchester, VA 22601
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  /59

  $600,000

  • 3 Beds
  • 1.5 Baths
  • 3,483 Sq Ft

  1311 Handley Ave, Winchester, VA 22601

  Nestled in the charming City of Winchester, this delightful Colonial home, built in 1952, exudes warmth and character. With its classic brick exterior and excellent condition, this residence invites you to experience a blend of traditional elegance and modern comfort. Step inside to discover a thoughtfully designed interior featuring beautiful hardwood floors that flow seamlessly throughout. The

  Kim Hurst MarketPlace REALTY

  1311 Handley Ave, Winchester, VA 22601
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  /58

  $748,900

  • 5 Beds
  • 3 Baths
  • 5,430 Sq Ft

  416 Briarmont Dr, Winchester, VA 22601

  Classic all-brick home in a highly desirable Winchester location! Well maintained and thoughtfully designed, this five bedroom, three full bath home offers timeless character, spacious living areas and exceptional convenience. The main level features a gracious living room with fireplace, cozy den with fireplace and bookshelves and a primary bedroom on the main level. Four additional bedrooms

  John Schroth Colony Realty

  416 Briarmont Dr, Winchester, VA 22601

Showing Results 81 - 115, Page 3 of 3