Winchester, VA Homes

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  /46

  $425,000

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

  133 Woodrow Rd, Winchester, VA 22602

  Welcome home to this charming split foyer in Carlisle Heights, ideally located on the east side of Winchester—just off Route 7 for an easy commute!Step inside to a light-filled interior featuring low-maintenance flooring throughout the main living areas and bedrooms, offering both comfort and practicality. The spacious, updated kitchen showcases white cabinetry, stainless steel

  

  Angie Ordonez

  NextHome Realty Select

  (540) 384-4063

  133 Woodrow Rd, Winchester, VA 22602
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  Explore Winchester

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  /8

  $1,150 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  2259 Papermill Rd Unit 4, Winchester, VA 22601

  This lower level apartment is an end unit. 1 bedroom,1 bath apartment is in a great location close to shopping and restaurants. NO Smoking, NO pets, NO Vaping. $30 application fee to cover credit and background check. Landlord is looking for around 700 credit score.

  

  Frank Armstrong, IV

  Colony Realty

  (540) 701-4871

  2259 Papermill Rd Unit 4, Winchester, VA 22601
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  /29

  $330,000 Sold Aug 01, 2025

  • 1,217 Sq Ft
  • $271/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  709 Panther Dr, Winchester, VA 22602

  Brand new and affordably priced! Built by Beiler and Company, this quality home offers an open layout with granite countertops, stainless steel appliances, and luxury vinyl plank flooring throughout. The smart split-bedroom design includes a private primary suite with dual closet and a walk-in shower. Nestled in a tranquil. wooded setting, this home also features a full walk-out basement ready to

  Lisa Gill ERA Oakcrest Realty, Inc.

  709 Panther Dr, Winchester, VA 22602
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  /43

  Est $434,835 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,190 Sq Ft

  512 Lanny Dr, Winchester, VA 22601

  512 Lanny Dr, Winchester, VA 22601
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  /71

  $1,250,000 Under Contract

  • Studio
  • 8,616 Sq Ft

  202 S Washington St, Winchester, VA 22601

  Back on the market due to NO fault of the Seller! Currently a single family home with a private “guest apartment”, but zoned multi-family with the potential for up to 4 units and potentially $4000.00+ in monthly rental income! Fantastic opportunity! The private guest suite currently has 2 bedrooms. The 3rd floor also has an additional 2 bedrooms, full bathroom and could laundry room that

  

  Lori Bales

  Keller Williams Realty

  (540) 917-5619

  202 S Washington St, Winchester, VA 22601
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  /12

  $2,400 per month

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  21 S Stewart St Unit 4, Winchester, VA 22601

  Charming Remodeled 2-Bedroom Apartment Near Old Town Winchester!Enjoy the perfect mix of comfort and convenience in this beautifully remodeled 2 bedroom, 2 bathroom apartment located just steps from historic Old Town Winchester. This spacious unit features modern updates, in-unit laundry, and a fully fenced private yard—ideal for relaxing or entertaining. You'll also love the generous storage

  

  Frank Armstrong, IV

  Colony Realty

  (540) 781-1596

  21 S Stewart St Unit 4, Winchester, VA 22601
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  /47

  $525,000 Sold Aug 01, 2025

  • 1,865 Sq Ft
  • $282/SF
  • 42 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1941

  336 Miller St, Winchester, VA 22601

  This beautiful cottage, nestled on the very sought after Miller St, supplies the utmost convenience for what Winchester has to offer. From walking distance to eateries and Old Town entertainment, a quick drive to supermarkets all around and Handley High School just one street away! Supplying 3 bedrooms 2 1/2 bathrooms across three levels you can appreciate the character of an older home with

  Julie Teets Long & Foster Real Estate, Inc.

  336 Miller St, Winchester, VA 22601
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  /37

  Est $427,003 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,052 Sq Ft

  222 E Piccadilly St, Winchester, VA 22601

  222 E Piccadilly St, Winchester, VA 22601
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  /46

  $995,000

  • 4 Beds
  • 2.5 Baths
  • 2,859 Sq Ft

  247 Mcguire Rd, Winchester, VA 22603

  Tucked away on a private 2.7-acre wooded lot, this stunning all-brick colonial has been fully renovated from top to bottom. Inside, 3/4" solid ash, 5"wide herringbone flooring flows throughout, accented by designer lighting, crown molding, and elegant chair rail trim. The chef’s kitchen is a true showstopper—featuring a massive island, striking white and gold appliances, and custom finishes. The

  

  Lori Bales

  Keller Williams Realty

  (540) 701-5541

  247 Mcguire Rd, Winchester, VA 22603
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  /13

  $1,700 - $2,400 per month

  The Local

  1 - 4 Beds

  230 Spring St, Winchester, VA 22601

  Modern designs, elegant finishes, and the most desirable amenities await you at the area’s newest apartment home living destination, the Local. Our Winchester apartments come in one, two, three, and four-bedroom floorplans, each featuring spacious and adaptable layouts. Various interior extras adorn them including an open floorplan concept, walk-in closets, in-unit washers/dryers, and more. As a

  230 Spring St, Winchester, VA 22601
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  /68

  $635,000 Sold Aug 01, 2025

  • 2,639 Sq Ft
  • $241/SF
  • 22 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2009

  800 Kennedy Dr, Winchester, VA 22601

  Welcome to 800 Kennedy Drive, a spacious Colonial by Richmond American Homes located in the desirable Rolling Hills Estates. This home offers three finished levels with a smart, open layout—perfect for everyday living and entertaining. The main level flows seamlessly from room to room, featuring beautiful hardwood floors and fresh new carpet throughout. The large family room, featuring a stone

  Cindy Greenya Keller Williams Realty

  800 Kennedy Dr, Winchester, VA 22601
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  /14

  Not Listed For Sale

  0 Susquehanna Trail, Winchester, VA 22602

  0 Susquehanna Trail, Winchester, VA 22602
• 

  

  /49

  $649,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,591 Sq Ft

  101 Morgan St, Winchester, VA 22601

  Downtown Winchester - 2 blocks from the walking mall with in-law suite or lower level rental potential! From the moment you arrive, you’ll be drawn in by this home’s timeless symmetry, classic brick exterior, and welcoming front porch. Thoughtful landscaping and charming details set the stage for what’s inside. With 5 bedrooms and 3 full baths, there’s plenty of space for everyone. The

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 858-1339

  101 Morgan St, 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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  /51

  $350,000 Sold Jul 31, 2025

  • 1,445 Sq Ft
  • $242/SF
  • 44 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1961

  671 Fox Dr, Winchester, VA 22603

  ESTATE SALE..... "owner's pride" this cozy Ranch well taken care of, PROPERTY OFFERS....separate laundry room with back door entry, 13x13 family room, dining room with patio door going out onto a 10x19 covered deck, one bevel living, beautiful hardwood floors throughout, cozy brick fireplace in living room, pull down attic for extra storage, fenced backyard with dusk-to-dawn pole light, garage

  Wanda Garris Miller Century 21 Redwood Realty

  671 Fox Dr, Winchester, VA 22603
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  /43

  Est $693,455 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,569 Sq Ft

  121 Wales Ct, Winchester, VA 22602

  121 Wales Ct, Winchester, VA 22602
• 

  

  /13

  $749,000 Coming Soon

  • 3 Beds
  • 3.5 Baths
  • 5,802 Sq Ft

  1205 Caroline St, Winchester, VA 22601

  **Do Not Miss This One!**Professional Photos Coming Soon** Don’t miss this rare opportunity in the heart of Winchester! Offered for the first time since it was custom built in 2001, this stunning all-brick ranch sits on a beautifully landscaped and private 0.94-acre lot that feels like your own personal park. With nearly 3,000 square feet of thoughtfully designed space on the main level, this

  

  Jim Shebest

  Coldwell Banker Realty

  (540) 802-5378

  1205 Caroline St, Winchester, VA 22601
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  /22

  $1,799 - $2,231 per month

  Meadow Branch Luxury Apartments

  1 - 2 Beds

  424 Ridgewood Ln, Winchester, VA 22601

  Welcome to Meadow Branch, where luxury and convenience are standard. Our community offers beautiful 1,2 and 3 bedroom apartment homes. Community means convenience and at Meadow Branch, everything you need is nearby. We are conveniently located adjacent to Winchester Medical Center and 2 miles from Old Town Winchester.

  424 Ridgewood Ln, Winchester, VA 22601
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  /75

  $1,071,134 Sold Jul 31, 2025

  • 5,000 Sq Ft
  • $214/SF
  • 1 Day On Market

  • 4 Beds
  • 5 Baths
  • Built 2006

  220 Anna Margaret Dr, Winchester, VA 22602

  Just minutes from town, this impressive all-brick residence in the sought-after Granville Estates offers the perfect blend of space, elegance, and versatility. Situated on nearly 3 acres, the home features over 5,000 square feet of thoughtfully designed living space, including a fully finished walkout basement and a detached 4-bay garage with an exceptional in-law suite.Step inside to a

  Bradley Comstock ERA Oakcrest Realty, Inc.

  220 Anna Margaret Dr, Winchester, VA 22602
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  /20

  Est $445,348 Not Listed For Sale

  • 2 Beds
  • 4 Baths
  • 2,160 Sq Ft

  206 N Kent St, Winchester, VA 22601

  206 N Kent St, Winchester, VA 22601
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  /9

  $225,000 Under Contract

  • Land
  • 6 Acres
  • $37,563 per Acre

  Lot 3 Cedar Creek Grade, Winchester, VA

  Beautiful lot in a small neighborhood on the very desirable west side of Winchester off Cedar Creek Grade! Lot is already perked for an alternative septic system. This opportunity doesn’t come along often! Rolling hills with beautiful surroundings and views. The location is less than 10 minutes to grocery stores, downtown Winchester, or Winchester Medical Center. It’s also located within 2

  

  Lori Bales

  Keller Williams Realty

  (540) 974-1542

  Lot 3 Cedar Creek Grade, Winchester, VA
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  /18

  $2,150 per month

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Townhouse for Rent

  413 Tevis St, Winchester, VA 22601

  NEWER UNIT HAS AN OPEN KITCHEN WITH GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, LED LIGHTING AND 1 USB/OUTLET COMBO IN KITCHEN. WHOLE HOUSE WINDOW TREATMENTS INCLUDED, WASHER/DRYER AND PROGRAMABLE THERMOSTAT. RENT INCLUDES EXTERIOR LAWN CARE AND SNOW REMOVAL. WASHER AND DRYER INCLUDED. VERY NEAR TO 1-81 AND ALL SHOPPING

  Rajesh Cheruku Ikon Realty - Ashburn

  413 Tevis St, Winchester, VA 22601
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  /21

  $500,000 Sold Jul 31, 2025

  • Land
  • 29 Acres
  • $16,972 per Acre

  • 180 Days On Market

  Tract 1 Golds Hill Rd, Winchester, VA 22603

  The seller will consider a backup offer.Prime Land Opportunity -29.46 acres located on Golds Hill Rd. Winchester VA. Property can be subdivided with county approval. It already has one perk site approved. Nestled just outside of Winchester, this property offers a rare opportunity to own a piece of real estate with exceptional potential. This vacant land is a canvas for your imagination,

  RoxAnn Grimes RE/MAX Roots

  Tract 1 Golds Hill Rd, Winchester, VA 22603
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  /30

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,442 Sq Ft

  4255 Middle Rd, Winchester, VA 22602

  4255 Middle Rd, Winchester, VA 22602
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  /8

  $225,000 Under Contract

  • Land
  • 6 Acres
  • $40,761 per Acre

  Lot 6 Cedar Creek Grade, Winchester, VA

  Beautiful lot in a small neighborhood on the very desirable west side of Winchester off Cedar Creek Grade! Lot is already perked for an alternative septic system. This opportunity doesn’t come along often! Rolling hills with beautiful surroundings and views. The location is less than 10 minutes to grocery stores, downtown Winchester, or Winchester Medical Center. It’s also located within 2

  

  Lori Bales

  Keller Williams Realty

  (540) 974-1542

  Lot 6 Cedar Creek Grade, Winchester, VA
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  /46

  $1,775 - $2,355 per month

  Stuart Hill

  1 - 3 Beds

  1981 Randolph Place, Winchester, VA 22601

  Nestled in the picturesque Shenandoah Valley in historic Winchester, Virginia, Stuart Hill Apartments combines convenience, a quality lifestyle, and warm, personalized service. Ideally situated just minutes from Historic Downtown Winchester, local shopping and dining, Shenandoah University, and the top-rated Winchester Medical Center, our community offers unparalleled access to everything you

  1981 Randolph Place, Winchester, VA 22601
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  /24

  $242,500 Sold Jul 30, 2025

  • 1,080 Sq Ft
  • $225/SF
  • 19 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1986

  208 Kimberly Way, Winchester, VA 22601

  Just Listed in Winchester, VA!A beautifully maintained 2-bedroom, 2.5-bath townhome. Offering 1,080 square feet of comfortable living space. This property combines small-town charm with functional features that make everyday living a breeze. Inside, a bright and airy living room and kitchen welcomes you with large windows and an exit door to the deck that allow natural light to pour in,

  Janet Smith NextHome Realty Select

  208 Kimberly Way, Winchester, VA 22601
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  /43

  Est $632,902 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,729 Sq Ft

  405 Lynnehaven Dr, Winchester, VA 22602

  405 Lynnehaven Dr, Winchester, VA 22602
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  /39

  $450,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 3,190 Sq Ft

  102 Shockey Cir, Winchester, VA 22602

  What a fantastic opportunity for 1-level living in a very desirable neighborhood within 3 minutes to downtown Winchester. This beautiful, all-brick home is located in Fairway Estates, also adjacent to the Winchester Country Club and golf course. It’s been very well-maintained of the years - move in ready and also happy to receive your updated touches. The full, large basement offers a guest

  

  Lori Bales

  Keller Williams Realty

  (540) 215-8959

  102 Shockey Cir, Winchester, VA 22602
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  /14

  $2,050 per month

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft
  • House for Rent

  116 Mill Race Dr, Winchester, VA 22602

  Looking for a great commuter rental on the east side of town? You found it ! 3BR 2.5 BA with large fenced rear yard that overlooks a horse farm. Nice sized master bedroom with master bath, main floor office/den with french doors. Wood laminate floors with separate dining room/generous sized living room with glass sliding doors to deck. Perfect for entertaining. Eat in kitchen with built in desk

  michele bouve hoffman Pearson Smith Realty, LLC

  116 Mill Race Dr, Winchester, VA 22602
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  /61

  $550,000 Sold Jul 30, 2025

  • 3,160 Sq Ft
  • $174/SF
  • 3 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1975

  683 Lake Saint Clair Dr, Winchester, VA 22603

  A rare find. House on Lake Saint Clair about 15 minutes from downtown Winchester. 35-acre lake and use of 175 acres, trails, hunting, and a shooting range. Lake St. Clair transfer fee of $5000.00 due at closing. Electric motorboats only, gasoline-powered boats are not allowed.

  John Schroth Colony Realty

  683 Lake Saint Clair Dr, Winchester, VA 22603
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  /6

  Not Listed For Sale

  • Studio
  • 1,710 Sq Ft

  13 E North Ave, Winchester, VA 22601

  13 E North Ave, Winchester, VA 22601
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  /45

  $475,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,466 Sq Ft

  106 Poe Dr, Winchester, VA 22602

  Welcome to This Lovely Richmond American Homes, Pearl Model. A Beautiful Single Family Home Located On An Oversized Corner Lot. 4 Bedroom, 3 Full Bathrooms. Gourmet Kitchen Boasts Quartz Counters, Stainless Steel Appliances, A Grand Island Housing the Farmhouse sink and quiet Dishwasher. An Spacious, Open Concept Main Level Featuring An Electric Fireplace. This Home Offers A Main Level Bedroom

  

  Adrian Blakeney

  EXP Realty, LLC

  (540) 805-8133

  106 Poe Dr, Winchester, VA 22602
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  /50

  $1,785 - $3,144 per month

  The Lofts at Jubal Square

  1 - 3 Beds

  1864 Old Jube Square, Winchester, VA 22601

  Weve got it all at the Lofts at Jubal Square, the newest addition to the charming andhistoric Winchester cityscape. We offer a total commitment to better living, boasting largeapartments with loft and garage options, as well as amenities ideal for all those seeking anexceptional apartment lifestyle. Discover the Lofts at Jubal Square and discover what itmeans to live the good life.

  1864 Old Jube Square, Winchester, VA 22601
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  /98

  $603,500 Sold Jul 30, 2025

  • 2,332 Sq Ft
  • $259/SF
  • 7 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2004

  107 Sesar Ct, Winchester, VA 22602

  BEAUTIFUL Brick home on Private Oasis on quiet cul-de-sac with spacious front porch, gorgeous HEATED IN-GROUND SWIMMING POOL & HOT TUB! Fully fenced backyard ready for the kids and pets, with large deck and multiple entertaining areas & stone patios, making your home "THE PLACE TO BE"!From the front porch, you will step into the 2-story foyer and notice the real hardwood flooring that leads

  Michele Gibson Samson Properties

  107 Sesar Ct, Winchester, VA 22602
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  /29

  Est $524,480 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,151 Sq Ft

  442 Canyon Rd, Winchester, VA 22602

  442 Canyon Rd, Winchester, VA 22602
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  /51

  $699,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft

  881 Adams Rd, Winchester, VA 22603

  *Price Adjustment on this beautiful property!*Welcome to this exquisite 3-bedroom, 2-bath rancher nestled on nearly 9 private acres, offering 2,250 square feet of refined living space and unmatched serenity. From the moment you enter, you'll be captivated by the elegance of rich wood floors, 9-foot ceilings, and exquisite crown molding with wide baseboards throughout. The great room is a true

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 402-9684

  881 Adams Rd, Winchester, VA 22603
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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

  Adorable downtown Winchester Duplex in quiet neighborhood . Spacious living area on primary floor along with kitchen, separate dining area, and washer dryer hook-up. Two bedrooms and one bathroom on the upper floor. Relax on the front porch or enjoy the back yard with access to a storage shed. Minimum Income $55,800.00 for maximum two adults income qualification. At least 680 credit

  Elna Brown Pearson Smith Realty, LLC

  221 Baker St, Winchester, VA 22601
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  /64

  $343,000 Sold Jul 30, 2025

  • 1,333 Sq Ft
  • $257/SF
  • 24 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2024

  151 Mccormick Cir Unit 200, Winchester, VA 22602

  Welcome to Winchester Landing, a thoughtfully designed 55+ condo community offering comfort, convenience, and modern living—unlike anything else available in a 55+ setting. There truly are no other condos like these!Ruby style condo features an updated, open floor plan where the kitchen flows seamlessly into the spacious great room—perfect for both daily living and entertaining. The

  Rhonda Shade ERA Oakcrest Realty, Inc.

  151 Mccormick Cir Unit 200, Winchester, VA 22602
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  /60

  Est $407,579 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,300 Sq Ft

  152 Solara Dr, Winchester, VA 22602

  152 Solara Dr, Winchester, VA 22602

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