Winchester, VA Homes

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  /60

  $550,000 Open Sun 12PM - 2PM

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

  121 N Washington St, Winchester, VA 22601

  A MUST SEE INSIDE!!!! This 2.5 story historic gem offers 3-4 beds, 2.5 baths and gourmet kitchen with brand new state of art appliances includes wine fridge, drawer style microwave, and pot filler. Formal living/dining room(s). Extras include den, office(s), nooks, and 3rd floor bonus room (perfect for kid's getaway). Laundry hook-ups on both main level and 2nd level. This home has been

  M. Kelly Walker RE/MAX Roots

  121 N Washington St, Winchester, VA 22601
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  /15

  $1,435 per month

  • 650 Sq Ft
  • House for Rent

  422 W Clifford St Unit 2, Winchester, VA 22601

  Bright, Beautiful, and Private! High-end, newly renovated 1-bedroom apartment with private deck located in the heart of downtown Winchester, easy walking distance to the walking mall. Apartment features air conditioning, granite countertops, stainless steel appliances (including a dishwasher), hardwood floors throughout, and a custom marble tile bathroom. Seeking long-term tenant. Strict no pets

  Gillian Greenfield Coldwell Banker Premier

  422 W Clifford St Unit 2, 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
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  /19

  Est $324,758 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,472 Sq Ft

  2928 First St, Winchester, VA 22601

  2928 First St, Winchester, VA 22601
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  /17

  $399,990 Open House 9/27

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

  TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601

  **SPECIAL OFFER! Receive Up to 15K IN FLEX CASH FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!**Featuring Bedford II in Valor Crossing! Open concept kitchen located next to the country kitchen and living room. Optional features include box bay rear window and 10' x 14' deck. Primary suite with large walk-in closet, dual vanity, and oversized seated shower in primary bath.

  Brittany Newman DRB Group Realty, LLC

  TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601
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  /37

  $4,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,409 Sq Ft
  • House for Rent

  126 Hawthorne Dr, Winchester, VA 22601

  Step into stylish comfort in this fully furnished mid-century modern home, ideally located near Winchester Medical Center and just a short walk to vibrant downtown Winchester. 3 bedroom, 2.5 baths, Perfect for doctors, traveling nurses, or anyone in need of a seamless transitional home, this property offers a turnkey living experience—just bring your suitcase. Enjoy the ease of lawn and exterior

  Randolph Craun Oakcrest Commercial LLC.

  126 Hawthorne Dr, Winchester, VA 22601
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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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  /8

  Est $238,756 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,064 Sq Ft

  521 Monticello St, Winchester, VA 22601

  521 Monticello St, Winchester, VA 22601
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  /57

  $575,000 Open House 10/05

  • 4 Beds
  • 3.5 Baths
  • 4,326 Sq Ft

  106 Homer Dr, Winchester, VA 22602

  Welcome to 106 Homer Dr – a well-maintained 4,326 sq ft colonial home nestled in the desirable Merrimans Chase community. This 4-bedroom, 3.5-bath home features an open floor plan ideal for modern living and entertaining. Enjoy generous living spaces including a finished walk-out basement. Thoughtfully designed with both functionality and comfort in mind, this home offers large bedrooms including

  RoxAnn Grimes RE/MAX Roots

  106 Homer Dr, Winchester, VA 22602
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  /52

  $1,950 per month

  • 3 Beds
  • 1.5 Baths
  • 1,612 Sq Ft
  • House for Rent

  440 N Loudoun St, Winchester, VA 22601

  Downtown living with historic charm! Just steps away from the award-winning Pizzoco Pizza—named one of the best in the Shenandoah Valley—and the historic downtown walking mall, this 3-bedroom, 1.5-bath home puts you right in the heart of it all. Inside, you’ll enjoy hardwood floors throughout, main-level laundry, and an updated full bath on the bedroom level. A huge attic offers plenty of extra

  Stephanie Feltner Realty ONE Group Old Towne

  440 N Loudoun St, Winchester, VA 22601
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  /18

  $258,000 Sold Aug 25, 2025

  • 1,360 Sq Ft
  • $190/SF
  • 52 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1944

  221 Boyd Ave, Winchester, VA 22601

  CHARMING HOME LOCATED CLOSE TO I-81 AND RT.7 HOME HAS 3 BEDROOMS WITH FULL BATH ON SECOND FLOOR AND HALF BATH ON FIRST. ADD YOUR PERSONAL TOUCHES AND MAKE THISA CUTE AND INVITING HOME. FRONT PORCH HAS BEEN GLASSED IN. PERFECT SPOT FOR YOUR MORNING COFFEE. **HOME BEING SOLD AS IS**

  Mary Hammond Jim Barb Realty Inc.

  221 Boyd Ave, Winchester, VA 22601
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  /71

  Est $354,243 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,600 Sq Ft

  517 Armour Dale, Winchester, VA 22601

  517 Armour Dale, Winchester, VA 22601
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  /44

  $539,000

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

  420 Westside Station Dr, Winchester, VA 22601

  Location Location. This is not your standard cookie cutter home. This meticulously maintained contemporary home is minutes from Winchester Medical Center and less than a mile to Rt. 37. Hardwood floors throughout the property. Beautiful new deck overlooks spacious backyard that backs to trees. Property offers a living room that serves as a perfect office. Kitchen features granite counters

  Kelly Bauer Coldwell Banker Premier

  420 Westside Station Dr, Winchester, VA 22601
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  /25

  $1,900 per month

  • 3 Beds
  • 1.5 Baths
  • 1,390 Sq Ft
  • Townhouse for Rent

  213 Copperfield Ln, Winchester, VA 22602

  Charming Townhome! Comfort, Convenience & Character.This inviting townhome is ready to welcome its next tenant with open arms. Thoughtfully updated and lovingly maintained, it offers the perfect blend of traditional design and modern comfort. Recent upgrades include:- New HVAC system (2024) for year-round efficiency- Fresh carpet and luxury vinyl plank flooring

  Donna McInturff Berkshire Hathaway HomeServices PenFed Realty

  213 Copperfield Ln, Winchester, VA 22602
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  /73

  $497,000 Sold Aug 25, 2025

  • 3,204 Sq Ft
  • $155/SF
  • 64 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2006

  903 Crestview Terrace, Winchester, VA 22601

  Seller offering $10,000 credit towards repair costs or closing costs depending on lender approval and the purchase agreement. Spacious 3-Level Colonial in Winchester’s Prime LocationNestled next to a charming park and within city limits, this 3-level brick-front Colonial offers both comfort and convenience. The home boasts a new roof installed in 2024 and a no HOA community, providing the

  MARIA STRIBLING EXP Realty, LLC

  903 Crestview Terrace, Winchester, VA 22601
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  /46

  Est $512,278 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,568 Sq Ft

  605 Kernstown Ct, Winchester, VA 22601

  605 Kernstown Ct, Winchester, VA 22601
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  /38

  $574,999

  • 4 Beds
  • 3.5 Baths
  • 3,824 Sq Ft

  102 Caliber Ct, Winchester, VA 22603

  Beautiful 4-Bedroom Home with Mountain Views – No HOA!Discover this stunning 4-bedroom, 3.5-bath home tucked away in a peaceful cul-de-sac, offering breathtaking northeast-facing views of the mountains and city skyline from the inviting front porch. Designed with both comfort and function in mind, the open-concept main level features a spacious living area, a well-appointed kitchen, and a

  Amy Emerson-Kerns Cambridge Premier Realty, LLC.

  102 Caliber Ct, Winchester, VA 22603
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  /31

  $2,000 per month

  • 3 Beds
  • 2.5 Baths
  • 1,220 Sq Ft
  • Townhouse for Rent

  290 Sage Cir, Winchester, VA 22603

  **PLEASE SEE DOCUMENTS FOR RENTAL APPLICATION INSTRUCTIONS**

  Rachel Olsen Keller Williams Realty

  290 Sage Cir, Winchester, VA 22603
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  /50

  $435,000 Sold Aug 22, 2025

  • 1,889 Sq Ft
  • $230/SF
  • 3 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2024

  107 Lakota St, Winchester, VA 22602

  Have you dreamed of living in a model home? This beautifully designed 1,889 sq. ft. Adams model townhome offers a custom-painted, 3-level layout perfect for modern living. Featuring 4 spacious bedrooms and 3.5 bathrooms, it’s ideal for all types of lifestyles. The front boasts a first-floor stone elevation, enhancing its curb appeal, and includes a convenient 1-car garage and composite deck.

  Brooks Sears D R Horton Realty of Virginia LLC

  107 Lakota St, Winchester, VA 22602
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  /67

  Est $525,055 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,732 Sq Ft

  624 Kernstown Ct, Winchester, VA 22601

  624 Kernstown Ct, Winchester, VA 22601
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  /65

  $529,000

  • 4 Beds
  • 2.5 Baths
  • 1,958 Sq Ft

  341 Warm Springs Rd, Winchester, VA 22603

  What a find! Gorgeous views with this 4BR 2.5BA Colonial situated on 1.22 acre lot. Features main level family room, living room, dining room and kitchen. Enjoy the screened in porch with hot tub; refreshing in ground pool with privacy fence. 2 car garage, basement for added comfort. Must see to appreciate!

  Toni Carone Long & Foster Real Estate, Inc.

  341 Warm Springs Rd, Winchester, VA 22603
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  /19

  $2,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,637 Sq Ft
  • House for Rent

  114 Haida Ln, Winchester, VA 22602

  Welcome to this spacious and inviting home featuring 3 bedrooms, 2.5 bathrooms, an open loft, and a 2-car garage. Whether you’re looking for a quiet office space or a second living area, the open loft upstairs offers that perfect flexibility.Step into the bright and airy open-concept living room, which flows seamlessly into a well-appointed eat-in kitchen. The kitchen features a tasteful

  Mauricio Argandona Fairfax Realty Select

  114 Haida Ln, Winchester, VA 22602
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  /36

  $390,000 Sold Aug 22, 2025

  • 2,238 Sq Ft
  • $174/SF
  • 3 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2016

  103 Sequoia Dr, Winchester, VA 22602

  103 Sequoia Drive is a beautifully upgraded 3-bedroom, 3.5-bath townhome offering over 2,200 square feet of finished living space. Located on the east side of Winchester, this home is a commuter’s dream with quick access to Route 7, Route 50, and I-81.The main level features an open-concept layout with gleaming hardwood floors, a spacious and sun-filled living room, and a gourmet kitchen

  Barton Chasler Realty ONE Group Old Towne

  103 Sequoia Dr, Winchester, VA 22602
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  /38

  Est $520,703 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft

  3022 Saratoga Dr, Winchester, VA 22601

  3022 Saratoga Dr, Winchester, VA 22601
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  /90

  $515,000 Open House 9/27

  • 3 Beds
  • 2.5 Baths
  • 1,984 Sq Ft

  2623 Middle Rd, Winchester, VA 22601

  Welcome home to 2623 Middle Rd! Now with a Virtual Tour of this beautiful home! Located near all that Winchester has to offer, Middle Rd is a lovely private oasis to come home to. With a myriad of upgrades including a gorgeous screened in back porch, this home offers many conveniences, a spacious layout and bedrooms, and plenty of room for entertainment, hobbies, and whatever you can dream of.

  Nicole Lewis Coldwell Banker Premier

  2623 Middle Rd, Winchester, VA 22601
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  /17

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 2,240 Sq Ft
  • House for Rent

  216 N Braddock St, Winchester, VA 22601

  Old charm meets custom architectural design. Remodeled to perfection including a modern kitchen, sunken living room and spa-like bathrooms. Backyard paradise allows you to enjoy the outdoor space. Rare oversized detached garage. Above the garage is a finished office space fit for an architect. So quit your commute and come work from home. Located in Historic downtown Winchester convenient to

  Amanda Slate Keller Williams Realty

  216 N Braddock St, Winchester, VA 22601
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  /107

  $775,000 Sold Aug 22, 2025

  • 5,161 Sq Ft
  • $150/SF
  • 35 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1999

  132 Wilton Dr, Winchester, VA 22603

  Beautifully Conceived Custom Colonial on 2.59 manicured acres with mature trees and landscaping. Versatile floor plan with Main Floor Primary and generous room sizes for elegant one level living, complemented by multiple bedrooms above and a fully finished basement--possible in-law suite with level walkout. Large composite deck features a screened gazebo and overlooks beautiful patio with stone

  Dallas Croft Samson Properties

  132 Wilton Dr, Winchester, VA 22603
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  /5

  Est $440,646 Not Listed For Sale

  329 Longview Ave, Winchester, VA 22601

  329 Longview Ave, Winchester, VA 22601
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  /36

  $549,000

  • 3 Beds
  • 2 Baths
  • 2,517 Sq Ft

  101 Dutton Place, Winchester, VA 22601

  Welcome to 101 Dutton Place— Location, Location, Location! + One Level living! Nestled just inside the Frederick County line in the highly sought-after Merrimans Estates community. This beautifully maintained ranch-style home is ideally situated on a peaceful and meticulously landscaped 1.26-acre lot, minutes from WMC Hospital, downtown Winchester & major commuter routes! Step through

  Lisa Behr Coldwell Banker Premier

  101 Dutton Place, Winchester, VA 22601
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  /34

  $1,395 per month

  • 2 Beds
  • 1 Bath
  • 1,022 Sq Ft
  • Townhouse for Rent

  221 Baker St, Winchester, VA 22601

  MOVE-IN READY Adorable downtown Winchester duplex in a quiet neighborhood! Features:Spacious living area on the main floorFreshly painted all throughoutKitchen with separate dining areaMicrowave, washer, and dryer includedTwo bedrooms & one bathroom upstairsCharming front porch & backyard with storage shed accessPhotos from last year Rental

  Elna Brown Pearson Smith Realty, LLC

  221 Baker St, Winchester, VA 22601
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  /61

  $400,000 Sold Aug 22, 2025

  • 2,200 Sq Ft
  • $182/SF
  • 26 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1922

  121 E James St, Winchester, VA 22601

  If your goal is to have an easy walk to Old Town Winchester, this is the home for you! Built in the early 1900's and full of charm!! The family room addition was done in1971 and is absolutely amazing!! Featuring 4 bedroom and 2 baths with approximately 2200 finished square feet!! Heating and air conditioning has been recently updated. The downstairs openness and light is incredible for this age

  Lisa Gill ERA Oakcrest Realty, Inc.

  121 E James St, Winchester, VA 22601
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  /43

  Est $418,377 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,355 Sq Ft

  2817 Broadview St, Winchester, VA 22601

  2817 Broadview St, Winchester, VA 22601
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  /114

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 1,798 Sq Ft

  720 S Kent St, Winchester, VA 22601

  Welcome to the beautifully preserved American Foursquare where music legend Patsy Cline once lived with her mother—and later, with her husband, Charlie Dick. Built in 1931, this four-bedroom, one-and-a-half-bath home blends timeless character with thoughtful updates, all wrapped in the charm of one of Winchester’s most historic neighborhoods.Inside, you’ll find nearly 1,800 square feet of

  Krissy Cruse Pearson Smith Realty, LLC

  720 S Kent St, Winchester, VA 22601
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  /10

  $2,000 per month

  • 2 Beds
  • 1 Bath
  • 1,650 Sq Ft
  • Condo for Rent

  107 Nevermore Dr, Winchester, VA 22602

  FULLY FURNISHED SHORT /MID/LONG term corporate rental. ALL UTILTIES /INTERNET/CABLE included. This is a beautiful “like new” spacious 2 BR 2 BA basement apt just off of Rt. 50 in Winchester Virginia. Great commuter location. Owners live upstairs but apt is 100% private..NO SMOKING / NO PETS Short Rental term must be a MINIMUM of 6 months— and then can be extended month to

  michele bouve hoffman Pearson Smith Realty, LLC

  107 Nevermore Dr, Winchester, VA 22602
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  /20

  $440,000 Sold Aug 22, 2025

  • 1,935 Sq Ft
  • $227/SF
  • 56 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2025

  101 Glenridge Dr, Winchester, VA 22602

  New construction! Conveniently located just minutes from town, this home offers comfort and style. With 3 bedrooms and 3 full baths, you will find many features such as beautiful hardwood floors throughout the main level, primary bedroom with walk in closet and bath with walk in shower, crown molding, granite counter top, 2 car garage and so much more! Don't miss the opportunity to make this

  Pamela Russell CENTURY 21 New Millennium

  101 Glenridge Dr, Winchester, VA 22602
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  /39

  Est $438,015 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,560 Sq Ft

  421 Longview Ave, Winchester, VA 22601

  421 Longview Ave, Winchester, VA 22601
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  /52

  $556,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,192 Sq Ft

  109 Murphy Ct, Winchester, VA 22602

  ****Project My Home Approved Listing, special financing available, call agent for details.******Charming Brick 4-Bedroom Rancher in Sought-After Sovereign Village – Winchester, VAWelcome to your new home in the desirable Sovereign Village neighborhood! This beautifully maintained detached ranch-style home is nestled on a large cul-de-sac lot, offering privacy, space, and comfort both

  Kathrin Donovan Keller Williams Realty

  109 Murphy Ct, Winchester, VA 22602
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  /14

  $1,750 per month

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

  15 E Piccadilly St Unit 201, Winchester, VA 22601

  "The Monument Lofts" are industrial style loft on the downtown walking mall with masterful design and high-end finishes. Sealed cement floors, high vaulted ceilings, wide open kitchen/living combination, and access to quaint workout facility and storage room make this loft your desired spot for year or years depending on your stay in Winchester! Parking space, Water/Sewer, electronic locks(

  Dave Spence RE/MAX Roots

  15 E Piccadilly St Unit 201, Winchester, VA 22601
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  /9

  $95,000 Sold Aug 22, 2025

  • 84 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1957

  1114 Cedar Grove Rd, Winchester, VA 22603

  Property has a great location but is probably a tear down. Health Documents available showing location of well/septic.

  Dave Spence RE/MAX Roots

  1114 Cedar Grove Rd, Winchester, VA 22603
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  /38

  Est $451,896 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  425 Longview Ave, Winchester, VA 22601

  425 Longview Ave, Winchester, VA 22601

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