Winchester County, VA Homes

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  /35

  $279,000

  • 2 Beds
  • 1 Bath
  • 1,176 Sq Ft

  239 Chestnut St, Winchester, VA 22601

  ******Price Reduction******239 Chestnut Street is a charming rancher in the heart of Winchester. 2 bedrooms, 1 bath, a large rear deck, eat in kitchen, laundry room could be converted into a third bedroom. Building in the back yard could be used as storage or a 1 car garage. This is a solid starter or downsizing home convenient to shopping,schools and parks. A little TLC will go a long way

  William Wertz Wildhawks Realty LLC

  239 Chestnut St, Winchester, VA 22601
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  /10

  $1,750 per month

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

  15 E Piccadilly St Unit 303, Winchester, VA 22601

  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 make this loft your desired spot for year or years depending on your stay in Winchester! Water/Sewer, Parking space, electronic locks( Latch/Butterfly) all included in rent. RentSpree Required by all applicants/Pets case

  Dave Spence RE/MAX Roots

  15 E Piccadilly St Unit 303, Winchester, VA 22601
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  /42

  $386,350 Sold Mar 14, 2025

  315 Gray Ave, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,638 Sq Ft
  • Built 1931

  Last Sold Summary

  • $236/SF
  • 1 Day On Market

  Last Listing Agent Devon Fox Samson Properties

  315 Gray Ave, Winchester, VA 22601
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  /6

  Est $292,159 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  3037 Papermill Rd, Winchester, VA 22601

  3037 Papermill Rd, Winchester, VA 22601
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  /55

  $685,000 Pending

  • 5 Beds
  • 4 Baths
  • 4,576 Sq Ft

  800 Lake Dr, Winchester, VA 22601

  Location Location Location! Welcome to 800 Lake Dr. Winchester VA 22601, Located in the highly sought-after Rolling Hills community and situated on a 0.37 acre lot, This expansive home offers 4,500+ sqft. of living space, featuring 5 bedrooms, 4 Full baths, finished basement, and 2 car garage! Step inside to find gleaming hardwood floors in the formal living and dining rooms. The unique

  Lisa Behr Hunt Country Sotheby's International Realty

  800 Lake Dr, Winchester, VA 22601
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  /15

  $1,500 - $1,575 per month

  Woodstock Terrace

  2 Beds

  1016 Woodstock Ln, Winchester, VA 22601

  Fully furnished apartments! TV, Internet provided!

  1016 Woodstock Ln, Winchester, VA 22601
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  /47

  $295,000 Sold Nov 03, 2025

  2964 Grace St, Winchester, VA 22601

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft
  • Built 1955

  Last Sold Summary

  • $378/SF
  • 22 Days On Market

  Current Estimated Value $295,149

  Last Listing Agent Jane Norton United Real Estate Premier

  2964 Grace St, Winchester, VA 22601
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  /24

  Est $327,680 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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  /2

  $300,000

  • 3 Beds
  • 1 Bath
  • 1,789 Sq Ft

  501 Battle Ave, Winchester, VA 22601

  Unwind on the covered front porch of this charming stone Cape Cod, ideally located on a spacious corner lot with sidewalks and a large, fenced backyard. Inside, the inviting living room features hardwood floors and a brick gas-log fireplace—perfect for cozy evenings. Hardwood flooring continues throughout the home, complemented by a convenient kitchen and dining combination. Two bedrooms are

  Susan Caulfield Pearson Smith Realty, LLC

  501 Battle Ave, Winchester, VA 22601
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  /29

  $2,550 per month

  • 2 Beds
  • 1.5 Baths
  • 1,465 Sq Ft
  • Condo for Rent

  122 N Loudoun St Unit 202, Winchester, VA 22601

  Step through the doors of this luxurious flat and immerse yourself in the grandeur of Old Town Winchester. Floor to ceiling windows, gleaming hardwood floors, and premium natural quartz counter tops leave nothing to be desired. Highlighted in this contemporary design are keyless entry, dish TV, WiFi, and sleek balconies. Call now to view theFlats@Bells!

  Dave Spence RE/MAX Roots

  122 N Loudoun St Unit 202, Winchester, VA 22601
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  /45

  $500,000 Sold Oct 15, 2025

  436 W Leicester St, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,592 Sq Ft
  • Built 1925

  Last Sold Summary

  • $314/SF

  Current Estimated Value $503,777

  Last Listing Agent Jeanne Mezzatesta Colony Realty

  436 W Leicester St, Winchester, VA 22601
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  /21

  Est $324,379 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,020 Sq Ft

  121 Summit Ave, Winchester, VA 22601

  121 Summit Ave, Winchester, VA 22601
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  /21

  $384,900

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

  711 E Cork St, Winchester, VA 22601

  This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door.

  Marco Novillo Spring Hill Real Estate, LLC.

  711 E Cork St, Winchester, VA 22601
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  /25

  $1,675 - $1,810 per month

  CEDAR HILL APARTMENTS

  2 - 3 Beds

  2250 Sofia Way, Winchester, VA 22601

  Cedar Hill Apartments offers well-appointed accommodations located in a convenient and relaxing environment. Only minutes away from Route 37, Route 11, and Jubal Early Drive, Cedar Hill apartments offers its tenants easy access to the Winchester Medical Center, Shenandoah University, loads of shopping and restaurants. Interior features include vaulted ceilings, gas fireplace, wood vanity

  2250 Sofia Way, Winchester, VA 22601
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  /30

  $329,400 Sold Aug 08, 2025

  613 Watson Ave, Winchester, VA 22601

  • 4 Beds
  • 2 Baths
  • 1,668 Sq Ft
  • Built 1946

  Last Sold Summary

  • $197/SF
  • 4 Days On Market

  Current Estimated Value $331,139

  Last Listing Agent Teri Domanski Corcoran McEnearney

  613 Watson Ave, Winchester, VA 22601
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  /40

  Est $295,293 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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  /38

  $320,000

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft

  1610 S Loudoun St, Winchester, VA 22601

  Welcome to this charming Cape Cod located in the heart of Winchester. Centrally situated just minutes from Old Town Winchester and Shenandoah University, this home offers both convenience and character.Step inside to a spacious living room featuring a cozy fireplace, which flows seamlessly into the kitchen and continues on to the dining room, creating an inviting layout for everyday living

  Heloisa Amar Samson Properties

  1610 S Loudoun St, Winchester, VA 22601
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  /6

  $1,000 per month

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

  510 N Kent St Unit 1, Winchester, VA 22601

  This 1 bedroom, 1 bath apartment is located on the first floor. Water & Sewer included in rent. Off street parking.

  Marisa Varley ERA Oakcrest Realty, Inc.

  510 N Kent St Unit 1, Winchester, VA 22601
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  /40

  $449,990 Sold Aug 12, 2025

  1827 Reese Ct, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 1,923 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $234/SF
  • 6 Days On Market

  D.R. Horton Abrams Crossing at Meadow Branch

  1827 Reese Ct, Winchester, VA 22601
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  /25

  Est $366,066 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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  /2

  $500,000

  • Studio
  • 1,175 Sq Ft

  513 and 525 Monticello St, Winchester, VA 22601

  For Sale – 1.89 + Acres Redevelopment Site located just off Valley Avenue in southern Winchester. Property consists of 2 parcels and includes a single family detached rental and one unimproved lot. Lot is zoned MR and Improved parcel is zoned B-2. Property is ideally suited for multi-family development. All properties are leased. Call listing broker for additional information. Do not disturb

  Brett Haynes Oakcrest Commercial LLC.

  513 and 525 Monticello St, Winchester, VA 22601
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  /20

  $1,499 - $1,919 per month

  Peppertree VA

  1 - 3 Beds

  221 Peppertree Ln, Winchester, VA 22601

  Tastefully designed 1, 2 and 3 bedroom floor plans and richly landscaped surroundings make for a welcome sight to call your home. Located in the heart of Winchester, Peppertree offers the conveniences of city living in a park-like setting. Peppertree is in close proximity to shopping, restaurants, schools and Winchester Medical Center.

  221 Peppertree Ln, Winchester, VA 22601
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  /36

  $525,000 Sold Nov 14, 2025

  2723 Windwood Dr, Winchester, VA 22601

  • 3 Beds
  • 3 Baths
  • 2,726 Sq Ft
  • Built 1999

  Last Sold Summary

  • $193/SF
  • 38 Days On Market

  Last Listing Agent LESLIE WEBB Long & Foster Real Estate, Inc.

  2723 Windwood Dr, Winchester, VA 22601
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  /22

  Est $291,696 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 954 Sq Ft

  313 Summit Ave, Winchester, VA 22601

  313 Summit Ave, Winchester, VA 22601
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  /10

  $370,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,868 Sq Ft

  126 N Euclid Ave, Winchester, VA 22601

  Discover this charming brick home that offers a perfect blend of classic character and modern convenience. This detached home features 4 spacious bedrooms and 3 full bathrooms, providing ample space for relaxation and privacy. The inviting living area boasts a cozy fireplace, ideal for creating warm memories during chilly evenings and on this level, you'll also have 2 bedrooms and a full bath.

  Marta Bingham Real Broker, LLC

  126 N Euclid Ave, Winchester, VA 22601
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  /7

  $1,450 per month

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

  208 W Boscawen St Unit 5, Winchester, VA 22601

  Enjoy the charm & convenience of downtown living in this 2 bedroom, 1 bath second floor apartment located just steps from Winchester's historic shops, restaurants & entertainment. This comfortable apartment features an efficient layout with easy access to coin operated laundry facilities on the main floor. A shared rear deck area provides a great spot to relax. New energy efficient windows

  Marisa Varley ERA Oakcrest Realty, Inc.

  208 W Boscawen St Unit 5, Winchester, VA 22601
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  /47

  $555,000 Sold Dec 22, 2025

  2307 Stoneridge Rd, Winchester, VA 22601

  • 5 Beds
  • 3.5 Baths
  • 3,280 Sq Ft
  • Built 2016

  Last Sold Summary

  • $169/SF
  • 5 Days On Market

  Last Listing Agent Dave Spence RE/MAX Roots

  2307 Stoneridge Rd, Winchester, VA 22601
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  /29

  Est $304,251 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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  /16

  $279,900 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,332 Sq Ft

  2901 Sorrell Ct, Winchester, VA 22601

  *Investor Opportunity, current tenants have a lease until May of 2027* Welcome to your new home! This beautifully maintained 3 -bedroom, 1.5 bath townhome offers comfort, convenience, and style in a great location. On the main level you will find a spacious kitchen with ample cabinetry and a breakfast area, the living room offers plenty of natural light, off the living room is a convenient half

  Amber Jenkins Century 21 Redwood Realty

  2901 Sorrell Ct, Winchester, VA 22601
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  /20

  $1,525 - $2,010 per month

  PEMBERTON

  2 - 3 Beds

  660 Pemberton Dr, Winchester, VA 22601

  Pemberton Village Apartments in Winchester VA is located in the prestigious Meadow Branch subdivision near the intersection of Jubal Early Drive and Harvest Drive. It is a ten building, 120 unit community easily assessable from Interstate 81 or Route 37. Conveniently located near the Apple Blossom Mall, fitness centers, John Handley High School, and Valley Health Medical Center; Pemberton Village

  660 Pemberton Dr, Winchester, VA 22601
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  /36

  $370,000 Sold May 13, 2025

  520 N Loudoun St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,459 Sq Ft
  • Built 1930

  Last Sold Summary

  • $254/SF
  • 32 Days On Market

  Current Estimated Value $374,648

  Last Listing Agent Dan Whitacre Colony Realty

  520 N Loudoun St, Winchester, VA 22601
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  /31

  Est $278,892 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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  /105

  $1,199,000 Under Contract

  • 5 Beds
  • 3.5 Baths
  • 5,262 Sq Ft

  819 Armistead St, Winchester, VA 22601

  Welcome to 819 Armistead Street. Located in the prestigious Meadow Branch neighborhood, this Colonial Revival style home has a nice Georgian flair to it. Marble floors welcome you into a large foyer. To your left is a living room with arched windows and wood floors. To your right, you'll find the dining room with arched windows, wood floors, and the original chandelier and toile wall paper chosen

  Natalie Langford ERA Oakcrest Realty, Inc.

  819 Armistead St, Winchester, VA 22601
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  /5

  $1,300 per month

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

  208 W Boscawen St Unit 12, Winchester, VA 22601

  This apartment is conveniently located to downtown Winchester. Coin Op Washer & Dryer on the main level. Rear deck access. Water & Sewer, weekly trash service and monthly pest treatment included in rent. Cat considered, no dogs. Minimum credit score of 650 and income equaled to 3X the rent required to apply. No Prior evictions.

  Marisa Varley ERA Oakcrest Realty, Inc.

  208 W Boscawen St Unit 12, Winchester, VA 22601
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  /50

  $465,000 Sold Jul 10, 2025

  350 Lanny Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 2,371 Sq Ft
  • Built 1967

  Last Sold Summary

  • $196/SF
  • 22 Days On Market

  Current Estimated Value $472,568

  Last Listing Agent Sheila Pack RE/MAX Roots

  350 Lanny Dr, Winchester, VA 22601
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  /19

  Est $326,803 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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  /52

  $374,900

  • 3 Beds
  • 1 Bath
  • 907 Sq Ft

  217 Myrtle Ave, Winchester, VA 22601

  Newly renovated and move-in ready! Everything is brand new in this super cute ranch home with a craftsman-style feel. Located in the City of Winchester in Northwestern Hills, schedule your appointment to see this stunning 3 BR 1 BA home with detached garage. New vinyl siding, roof, heat pump, GE appliances, cabinets, granite countertops, undercabinet lighting, flooring, landscaping, doors,

  Pamela Foltz Realty ONE Group Old Towne

  217 Myrtle Ave, Winchester, VA 22601
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  /29

  $1,975 per month

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Condo for Rent

  342 Fairmont Ave Unit 3, Winchester, VA 22601

  Gorgeous, large, fully furnished two bedroom apartment.Amazing location in beautiful well-established neighborhood. Just two short walking blocks to the Old Town Winchester pedestrian mall with shops, restaurants, cafes and entertainment.Located inside an 1840s hstoric house, this two bedroom apartment features original hardwood floors, high ceilings, crown molding, large windows,

  342 Fairmont Ave Unit 3, Winchester, VA 22601
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  /14

  $460,000 Sold Aug 07, 2025

  2620 Stonegate Dr, Winchester, VA 22601

  • 5 Beds
  • 3 Baths
  • 2,974 Sq Ft
  • Built 1995

  Last Sold Summary

  • $155/SF
  • 10 Days On Market

  Current Estimated Value $471,776

  Last Listing Agent Anthony Adamovich Key Move Properties, LLC.

  2620 Stonegate Dr, Winchester, VA 22601
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  /8

  Est $239,936 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

Showing Results 161 - 200, Page 5 of 18