Winchester, VA Homes

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  /55

  $499,000

  • 3 Beds
  • 1 Bath
  • 2,050 Sq Ft

  3634 Wardensville Grade, Winchester, VA 22602

  Country charm meets convenience at 3634 Wardensville Grade—just minutes to Old Town Winchester, Rt 50, Rt 37 and I 81—set on just under 9 acres with 2,572 sq ft, 3 bedrooms, and 1 bath. This light-filled home offers an easy-flow layout with generous gathering spaces, a bright kitchen, and flexible rooms ideal for a home office or hobby area. Cozy warmth comes from two woodstoves and a pellet

  Kira Grubb Realty ONE Group Old Towne

  3634 Wardensville Grade, Winchester, VA 22602
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  /54

  $3,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,164 Sq Ft
  • House for Rent

  604 Bittersweet Ct, Winchester, VA 22601

  Great location in the City of Winchester on a cul de sac! ONE PET may be acceptable. Case by Case. Five minutes from Winchester Medical Center.Spacious, freshly painted home, approximately 3,000 finished sq feet ! Finished basement with a full bath. Covered deck to relax on in the mornings or afternoons! New roof 2025, new shutters 2024, new screens 2024, new washer/dryer 2025, two

  Sheila Pack RE/MAX Roots

  604 Bittersweet Ct, Winchester, VA 22601
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  /13

  $190,000 Sold Aug 28, 2025

  • Land
  • 5.4 Acres
  • $35,185 per Acre

  • 34 Days On Market

  LOT B 4661 Middle Rd, Winchester, VA 22602

  Prime level 5.4- acre lot approved for a 4-bedroom standard septic system and well. Gently rolling and surrounded by nature, it the perfect canvas for your custom built-home. Don't miss this rare opportunity to own a piece of the country side just minutes from downtown Winchester. Call listing Agent to see property.

  Maureen Cunningham Century 21 Redwood Realty

  LOT B 4661 Middle Rd, Winchester, VA 22602
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  /30

  Est $295,706 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 829 Sq Ft

  3105 Papermill Rd, Winchester, VA 22601

  3105 Papermill Rd, Winchester, VA 22601
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  /56

  $760,000

  • 4 Beds
  • 2.5 Baths
  • 2,937 Sq Ft

  442 Frog Hollow Rd, Winchester, VA 22603

  Nestled in the serene Frog Hollow Estates, this charming Colonial home offers a perfect blend of comfort and functionality. With four spacious bedrooms and 2.5 bathrooms, the interior is designed for modern living. The traditional floor plan flows seamlessly into a family room off the kitchen, creating a warm atmosphere for entertaining. Step outside to discover 11 acres of picturesque land,

  Wendy Conner Coldwell Banker Premier

  442 Frog Hollow Rd, Winchester, VA 22603
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  /33

  $2,325 per month

  • 3 Beds
  • 2.5 Baths
  • 1,200 Sq Ft
  • Townhouse for Rent

  104 Reign Way, Winchester, VA 22603

  Discover this spacious three-level, beautiful townhome, built by Ryan Homes in 2018, now available for long-term lease! All professional photos will be added soon.This beautiful townhouse features three bedrooms, each with walk-in closets, two full bathrooms, and one half-bath. The open floor plan includes a generously sized kitchen with an island, a spacious dining area, and a separate

  Kalyan Karki Pearson Smith Realty, LLC

  104 Reign Way, Winchester, VA 22603
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  /81

  $315,000 Sold Aug 27, 2025

  • 1,317 Sq Ft
  • $239/SF
  • 5 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1936

  709 N Braddock St, Winchester, VA 22601

  Welcome to this charming two-story in-town home offering 3 bedrooms, 2 baths, and an oversized yard with a true backyard oasis. A detached garage, wired for electric, provides ample space for parking, storage, or outdoor entertaining. The covered front porch offers a peaceful spot to sit, sip, and rejuvenate.Inside, the main level showcases a traditional layout with many restored original

  Jaclyn Michelle Berkshire Hathaway HomeServices PenFed Realty

  709 N Braddock St, Winchester, VA 22601
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  /37

  Est $339,911 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft

  2905 First St, Winchester, VA 22601

  2905 First St, Winchester, VA 22601
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  /53

  $679,000 Open Sun 11AM - 1PM

  • 6 Beds
  • 4 Baths
  • 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

  Danielle Spriggs Real Broker LLC

  1400 Valley Ave, Winchester, VA 22601
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  /45

  $2,300 per month

  • 2 Beds
  • 2 Baths
  • 1,024 Sq Ft
  • Condo for Rent

  1310 Ramseur Ln, Winchester, VA 22601

  Wonderful condo that's just waiting for you! This 2 bedroom, 2 bath condo has been upgraded with all new plank flooring, new SS appliances in the kitchen, a new counter, upgraded bathrooms, plus a new stack washer/dryer unit. Every room has 9' + ceilings with crown molding and the master bedroom has a nice walk-in closet for all your essentials! For extra storage, there's a locked room with

  Cindy Butler Virginia Property Group, Inc.

  1310 Ramseur Ln, Winchester, VA 22601
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  /74

  $794,000 Sold Aug 27, 2025

  • 4,295 Sq Ft
  • $185/SF
  • 4 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2005

  1001 Armistead St, Winchester, VA 22601

  Spacious & Elegant 5-Bedroom Colonial in the Heart of Winchester!This beautifully maintained 5-bedroom, 4-bath Colonial offers over 4,000 sq. ft. of comfortable living in the City of Winchester. Hardwood flooring flows throughout the home, creating a warm and inviting atmosphere. The main level includes a convenient bedroom, a sunroom filled with natural light, and access to a large

  Sheila Pack RE/MAX Roots

  1001 Armistead St, Winchester, VA 22601
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  /24

  Est $328,995 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  2959 S Pleasant Valley Rd, Winchester, VA 22601

  2959 S Pleasant Valley Rd, Winchester, VA 22601
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  /50

  $570,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,862 Sq Ft

  114 Harold Ct, Winchester, VA 22602

  Welcome to this beautiful brick-front home, perfectly situated on a private cul-de-sac in the highly sought-after Abrams Pointe neighborhood. This move-in ready property, built by Joseph Mohr Construction, has been meticulously maintained by its original owners. An open floorplan begins in the dining space, enhanced by a stylish tray ceiling and classic chair railings, and flows seamlessly into

  Lisa Lowery Keller Williams Realty

  114 Harold Ct, Winchester, VA 22602
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  /15

  $1,900 per month

  • 2 Beds
  • 2.5 Baths
  • 1,280 Sq Ft
  • Townhouse for Rent

  2975 Sorrell Ct, Winchester, VA 22601

  Fantastic end unit townhouse in a great location! This clean and spacious two bedroom/two and a half bath townhome is available immediately. Fresh paint and carpet! Located in the City of Winchester and convenient to shopping, restaurants, and all the local amenities. Enjoy the private corner lot with a large and fully fenced rear yard, generous patio, and shed for exterior storage. The main

  Amanda White Nova Home Hunters Realty

  2975 Sorrell Ct, Winchester, VA 22601
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  /61

  $600,000 Sold Aug 27, 2025

  • 2,898 Sq Ft
  • $207/SF
  • 2 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1993

  315 W Whitlock Ave, Winchester, VA 22601

  Come home to 315 W Whitlock Avenue, a charming and meticulously maintained 2,898 sq ft Cape Cod Colonial nestled in a desirable, close-knit Winchester neighborhood. This unique one-owner home, originally built in 1992 and significantly updated in 2013 and 2021, seamlessly blends classic architectural style with modern amenities. This home offers two full stories, featuring a classic brick front

  Dan Whitacre Colony Realty

  315 W Whitlock Ave, Winchester, VA 22601
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  /40

  Est $292,231 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  2937 Grace St, Winchester, VA 22601

  2937 Grace St, Winchester, VA 22601
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  /42

  $767,900

  • 3 Beds
  • 3 Baths
  • 2,112 Sq Ft

  1049 Laurel Grove Rd, Winchester, VA 22602

  Tucked away on a quiet cul-de-sac, this custom 3-bedroom, 3-bath home is sited on a private, wooded lot offering stunning mountain views and a true sense of seclusion. The property provides a serene, park-like setting that feels worlds away, yet is conveniently located. The main-level primary suite features an elegant bathroom with a walk-in shower and soaking tub. The additional Two bedrooms on

  LESLIE WEBB Long & Foster Real Estate, Inc.

  1049 Laurel Grove Rd, Winchester, VA 22602
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  /22

  $1,550 per month

  • 2 Beds
  • 1 Bath
  • 868 Sq Ft
  • Townhouse for Rent

  2641 Valley Ave, Winchester, VA 22601

  Freshly renovated and ready to rent! 2 bedroom, 1 bath back apartment right off Valley Ave for convenience. Exposed beams, new flooring, ceiling fans, new appliances, brick accent wall, have it all. Off street shared parking. Jack & Jill bathroom, updated and new for you. Back bedroom has separate entrance too. Building has new metel roof & siding will be replaced next. Be close to it all in

  Sarah Abderrazzaq Realty ONE Group Old Towne

  2641 Valley Ave, Winchester, VA 22601
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  /115

  $365,000 Sold Aug 27, 2025

  • 2,254 Sq Ft
  • $162/SF
  • 5 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2001

  112 Eagle Trail, Winchester, VA 22602

  Beautiful Split Foyer "one of a kind" inside and out! in front of the house is a beautiful stone patio with retaining stone wall, outside is fenced, flower beds, stone retaining flowerbed walls, custom sidewalks, the front yard is a framework of landscaping a beautiful Rock Garden filled with lights, flowers, rocks, and stones, it has the perfect appropriate planting, that adds to this formal

  Wanda Garris Miller Century 21 Redwood Realty

  112 Eagle Trail, Winchester, VA 22602
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  /26

  Est $306,133 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  2952 Grace St, Winchester, VA 22601

  2952 Grace St, Winchester, VA 22601
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  /42

  $549,000

  • 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

  Dan Whitacre Colony Realty

  420 W Cork St, Winchester, VA 22601
• 

  

  /19

  $2,200 per month

  • 3 Beds
  • 2.5 Baths
  • 1,509 Sq Ft
  • Townhouse for Rent

  115 Nootka Way, Winchester, VA 22602

  Discover the epitome of luxury living in this stunning new construction townhouse located in the exclusive Retreat at Winding Creek. Completed in 2025, this exquisite residence features an open floor plan that seamlessly blends the gourmet kitchen with the inviting living area, perfect for entertaining. Enjoy high-end finishes, including upgraded countertops, stainless steel appliances, and

  Ken Isaacman Keller Williams Realty

  115 Nootka Way, Winchester, VA 22602
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  /32

  $469,000 Sold Aug 27, 2025

  • 2,850 Sq Ft
  • $165/SF
  • 25 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1964

  152 Burnt Church Rd, Winchester, VA 22603

  Beautifully updated, all-brick multi-generational home with space, privacy, and location all in one!Completely modernized, this move-in ready home offers over 2,800 finished square feet across two fully functional levels, ideal for families who want to live together with the freedom of their own space. Featuring 3 large bedrooms and 2 full bathrooms on the main level, plus a full in-law

  Cheryl Spangler Spangler Real Estate

  152 Burnt Church Rd, Winchester, VA 22603
• 

  

  /25

  Est $384,261 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,147 Sq Ft

  2921 Second St, Winchester, VA 22601

  2921 Second St, Winchester, VA 22601
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  /59

  $625,000

  • 4 Beds
  • 3.5 Baths
  • 3,296 Sq Ft

  478 Brookneil Dr, Winchester, VA 22602

  Welcome to 478 Brookneil Drive, a solidly built 4-bedroom, 3.5-bath home nestled on 5.16 acres in sought after Brookneil Subdivision. This property blends the best of rural living with the convenience of being just minutes from town, major commuter routes, schools, shopping, 7 minutes to Winchester Medical Center and all that Winchester has to offer.The home itself offers a timeless floor

  Katrina Smith RE/MAX Roots

  478 Brookneil Dr, Winchester, VA 22602
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  /31

  $2,400 per month

  • 3 Beds
  • 2.5 Baths
  • 1,962 Sq Ft
  • Townhouse for Rent

  113 Tye Ct, Winchester, VA 22602

  Beautiful 3 bedroom, 2.5 bath townhome for rent in Winchester at Senensy Village. This townhome has 3 levels, a 1-car garage, and an open floor plan. The lower and main levels have luxury vinyl planking, stainless steel appliances and granite countertops in the kitchen, as well as a Ring doorbell available for tenant to use. Upstairs has laundry room with Washer and Dryer included, 3 bedrooms,

  April Geyer CENTURY 21 New Millennium

  113 Tye Ct, Winchester, VA 22602
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  /37

  $430,000 Sold Aug 27, 2025

  • 68 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  2824 Broadview St, Winchester, VA 22601

  Welcome to this stunningly new built 3-bedroom beautiful home located in the heart of Winchester. Enjoy the unbeatable convenience of being just moments from shopping Centers, playgrounds, theatres, and more.Step inside to experience the fresh scent of new construction and move-in-ready living, complete with brand new-flooring, modern appliances, and a thoughtfully designed layout perfect for

  Elizabeth Flood Keller Williams Realty

  2824 Broadview St, Winchester, VA 22601
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  /22

  Est $297,543 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 954 Sq Ft

  313 Summit Ave, Winchester, VA 22601

  313 Summit Ave, Winchester, VA 22601
• 

  

  /59

  $655,000

  • 4 Beds
  • 3 Baths
  • 4,385 Sq Ft

  150 Harvest Ridge Dr, Winchester, VA 22601

  Find comfort and elegance in this spacious and ready-to-move-in Craftsman-style home in The Village at Harvest Ridge. Designed for a vibrant lifestyle in a welcoming community, this home showcases a harmonious blend of modern comfort and timeless craftsmanship, and offers nearly 4,500 square feet of lovingly maintained living space.Step inside to discover an inviting open floor plan

  Bridget Aikens Colony Realty

  150 Harvest Ridge Dr, Winchester, VA 22601
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  /15

  $1,148 per month

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

  1816 Valley Ave Unit 1, Winchester, VA 22601

  Freshly Remodeled 1 BR Apartment available. Centered in the heart of Winchester, walking distance to shops, restaurants, and entertainment. Utilities and WIFI are included at no charge. No pets allowed. Come and enjoy all of what Winchester has to offer. On-site Laundromat, WIFI and Camera Monitoring.

  Raj Patel Ikon Realty - Ashburn

  1816 Valley Ave Unit 1, Winchester, VA 22601
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  /60

  $400,000 Sold Aug 26, 2025

  • 2,538 Sq Ft
  • $158/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  319 Beechcroft Rd, Winchester, VA 22601

  Charming Brick Rancher with Modern Updates and Timeless Character.Welcome to this beautifully maintained brick rancher offering the perfect blend of classic charm and thoughtful updates. Featuring 3 spacious bedrooms and 2 full bathrooms, this home is designed for comfort, function, and style.Step onto the covered front porch, complete with a ceiling fan, Timber tech flooring and a

  Gidget Smallwood Coldwell Banker Premier

  319 Beechcroft Rd, Winchester, VA 22601
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  /29

  Est $307,678 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft

  2917 First St, Winchester, VA 22601

  2917 First St, Winchester, VA 22601
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  /68

  $509,900

  • 4 Beds
  • 2.5 Baths
  • 2,414 Sq Ft

  438 Mountain Falls Blvd, Winchester, VA 22602

  A RARE Find in Wilde Acres for such a MAGNIFICENT Property! So Majestic with Incredible Curb Appeal! You will be SO Taken by the Beauty of this Very Well Maintained Home/LOT (1 AC) & Additional Lots (.25 AC EA) 2 additional LOTS (separate tax records: TAX ID: 58-A02-R-5-5 AND TAX ID: 58-A02-R-5-24). All together 1.5 ACRES! Sit on the new trex deck to view the small creek with a

  Jodi Costello ERA Oakcrest Realty, Inc.

  438 Mountain Falls Blvd, Winchester, VA 22602
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  /3

  $995 per month

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

  1816 Valley Ave Unit 7, Winchester, VA 22601

  We are okay with Short term or Yearly lease.Freshly Remodeled Studio Apartment available. Centered in the heart of Winchester, walking distance to shops, restaurants, and entertainment. Utilities and WIFI are included at no charge. No pets allowed. Come and enjoy all of what Winchester has to offer. $995 per Month or $275 per WeekOn-site Laundromat, WIFI and Camera Monitoring.

  Raj Patel Ikon Realty - Ashburn

  1816 Valley Ave Unit 7, Winchester, VA 22601
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  /34

  $360,000 Sold Aug 26, 2025

  • 1,773 Sq Ft
  • $203/SF
  • 11 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1992

  203 Pembridge Dr, Winchester, VA 22602

  Welcome to this well-maintained split-foyer home, offering five bedrooms and two full bathrooms across two thoughtfully designed levels. Hardwood floors extend throughout the main level, adding warmth and character to the central living spaces.The kitchen is both functional and stylish, featuring stainless steel appliances—including a new refrigerator and dishwasher (2023)—along with

  Chris Craddock EXP Realty, LLC

  203 Pembridge Dr, Winchester, VA 22602
• 

  

  /31

  Est $266,856 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 850 Sq Ft

  2944 Second St, Winchester, VA 22601

  2944 Second St, Winchester, VA 22601
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  /46

  $489,000

  • 4 Beds
  • 3 Baths
  • 2,654 Sq Ft

  219 Milam Dr, Winchester, VA 22602

  Welcome to 219 Milam Drive, a spacious and updated all-brick rancher tucked in a quiet neighborhood just minutes from downtown Winchester, Route 7, and I-81. This four-bedroom, three-bath home offers over 2,700 square feet of finished living space, including a partially finished basement and additional storage or hobby rooms to suit your needs. Inside, you’ll find warm hardwood flooring, modern

  Kira Grubb Realty ONE Group Old Towne

  219 Milam Dr, Winchester, VA 22602
• 

  

  /19

  $1,850 per month

  • 3 Beds
  • 2.5 Baths
  • 1,488 Sq Ft
  • Townhouse for Rent

  127 Lighthouse Ln, Winchester, VA 22602

  Location, Location, Location!!! This 3 level townhome features 3 bedrooms, 2 1/2 baths, large eat-in country kitchen with pantry, living room, office and garage with auto-opener. All appliances included. There is a deck off the dining area. Primary bedroom has full bath and walk-in closet. Community amenities include fenced pool and mowing. Landlord pays the HOA Fee. Non smoking. No

  Barbara Gaul Jim Barb Realty, Inc.

  127 Lighthouse Ln, Winchester, VA 22602
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  /34

  $350,000 Sold Aug 26, 2025

  • 1,330 Sq Ft
  • $263/SF
  • 3 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1981

  303 Beechcroft Rd, Winchester, VA 22601

  Enjoy the ease of single-story living in this spacious brick rancher, ideally located just minutes from all the in-town amenities Winchester has to offer. Set on a lovely lot with mature trees in the backyard, this home offers both comfort and convenience in a timeless layout.Relax on the welcoming front porch, perfect for morning coffee or evening chats, and enjoy the practical benefits

  Bradley Comstock ERA Oakcrest Realty, Inc.

  303 Beechcroft Rd, Winchester, VA 22601
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  /28

  Est $292,671 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 975 Sq Ft

  2916 First St, Winchester, VA 22601

  2916 First St, Winchester, VA 22601

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