Winchester, VA Homes

• 

  

  

  /19

  $454,990 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,637 Sq Ft

  117 Monacan St, Winchester, VA 22602

  The Cabral is a 1,665-square-foot, two-story home with three bedrooms, 2.5 bathrooms, a loft, and a two-car garage. The open-concept main level features a spacious living room, an eat-in kitchen with stainless steel appliances, a walk-in pantry, and a sliding glass door to the backyard. Upstairs, the owner’s suite boasts a large bedroom, walk-in closet, and luxurious bath, complemented by two

  Tracy Jennings D R Horton Realty of Virginia LLC

  117 Monacan St, Winchester, VA 22602
• 

  

  /2

  $1,600 - $1,800 per month

  Apartment for Rent

  1-2 Beds

  148 N Loudoun St, Winchester, VA 22601

  Beautiful 1 and 2 bedroom fully furnished apartments. Located directly on the old town walking mall. Washer dryer included in the unit. On site parking.

  148 N Loudoun St, Winchester, VA 22601
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  /5

  $255,000 Sold Jun 10, 2025

  • Land
  • 7 Acres
  • $39,171 per Acre

  • 1 Day On Market

  0 0 Unit VAFV2034582, Winchester, VA 22602

  Lovely rolling 6.51 acres of farm land with 18x27 barn with stalls. Newer 25x45 run-in/machine shed metal building and 18x30 garage attached to barn. 1/2 acre pond recently redone. Within minutes of city amenities in a lovely rural community. Owner will not perk. Sold "as is".

  Cathy Durbin Crum Realty, Inc.

  0 0 Unit VAFV2034582, Winchester, VA 22602
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  /72

  Est $1,027,519 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,340 Sq Ft

  2101 Cedar Grove Rd, Winchester, VA 22603

  2101 Cedar Grove Rd, Winchester, VA 22603
• 

  

  

  /35

  $724,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,113 Sq Ft

  761 Fall Run Ln, Winchester, VA 22602

  Prepare to be captivated by the beauty and tranquility of this exceptional custom-built home, nestled on 8.59 acres with breathtaking mountain views. Offering desirable one-level living, this nearly new (under 3 years old) residence boasts two expansive patios perfect for savoring the stunning surroundings. Step inside to discover a meticulously designed open-plan layout, ideal for both

  Theo Theologis Slones Real Estate

  761 Fall Run Ln, Winchester, VA 22602
• 

  

  /5

  $1,000 per month

  • 1 Bath
  • 2,431 Sq Ft
  • Condo for Rent

  506 N Loudoun St Unit 2, Winchester, VA 22601

  Located within walking distance of Old Town Winchester this spacious efficiency is now available for rent. Water/sewer and trash included in rent. Tenant pays electric. No smoking, no pets. VAR or NVAR rental application w/ $50 per person application fee or apply online.

  Mandie Gladwell OliveTree Property Group, LLC

  506 N Loudoun St Unit 2, Winchester, VA 22601
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  /46

  $486,000 Sold Jun 10, 2025

  • 3,344 Sq Ft
  • $145/SF
  • 12 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1996

  112 Rebels Cir, Winchester, VA 22602

  Nestled on a quiet cul-de-sac in the desirable Pioneer Heights subdivision on Winchester’s East Side, this charming 4-bedroom, 3-bath rancher offers the perfect blend of comfort, style, and flexibility.Enjoy a generous backyard framed by mature trees, with a newer composite deck that’s perfect for outdoor entertaining. Inside, the expansive family room features a cozy gas fireplace and opens to a

  Laura White ERA Oakcrest Realty, Inc.

  112 Rebels Cir, Winchester, VA 22602
• 

  

  /19

  Not Listed For Sale

  • 2 Beds
  • 4 Baths
  • 2,052 Sq Ft

  204 N Kent St, Winchester, VA 22601

  204 N Kent St, Winchester, VA 22601
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  /59

  $485,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,400 Sq Ft

  2796 Green Spring Rd, Winchester, VA 22603

  This impressive home and property blend the perfect mix of being close to town, and living in quiet, picturesque surroundings. The house is 2400 square feet with 4 bedrooms and 2 bathrooms. There was an expansive two-story addition completed in 2000, boasting a large primary suite with two walk-in closets and an additional storage room upstairs. The main level features three bedrooms and one

  Jessica Corliss Dandridge Realty Group, LLC

  2796 Green Spring Rd, Winchester, VA 22603
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  /20

  $1,512 - $2,098 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
• 

  

  /59

  $562,000 Sold Jun 10, 2025

  • 3,386 Sq Ft
  • $166/SF
  • 24 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2025

  119 Manasquan Way, Winchester, VA 22602

  Quick Move-In Salem Model with Below-Market Interest Rates Available! This spacious 4 bedroom, 3.5 bath home offers 2686 sq ft on the top two floors with a first-floor primary suite for easy main-level living. The open-concept design is perfect for entertaining, and the stone front elevation adds timeless curb appeal. Enjoy the added space of a finished recreation room with an additional

  Brooks Sears D R Horton Realty of Virginia LLC

  119 Manasquan Way, Winchester, VA 22602
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  /66

  Est $544,998 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,930 Sq Ft

  3392 Back Mountain Rd, Winchester, VA 22602

  3392 Back Mountain Rd, Winchester, VA 22602
• 

  

  /49

  $280,000

  • Land
  • 25 Acres
  • $11,129 per Acre

  Mockingbird Lane Lot Unit WP007A, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Mockingbird Lane. Features a fully functional hunting cabin wired for a generator hook up with a wood stove and propane used for heating and cooking. The cabin has an open layout and separate sleeping quarters in

  Chad Pangle

  Mockingbird Lane Lot Unit WP007A, Winchester, VA 22603
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  /17

  $1,600 per month

  • 3 Beds
  • 1 Bath
  • 950 Sq Ft
  • House for Rent

  122 Chandler Ct, Winchester, VA 22603

  Beautiful 3bd 1 bath house located 10 minutes from Winchester Medical Center. Hardwood flooring throughout most of the home. Wash and dryer included. Tenant(s) responsible for yard maintenance. $47 application fee. REQUIREMENTS TO QUALIFY: (1) Household annual income $72k minimum, (2) Good credit, (3) Good landlord reference

  Courtney Spaid Crum Realty, Inc.

  122 Chandler Ct, Winchester, VA 22603
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  /66

  $650,000 Sold Jun 10, 2025

  • 2,824 Sq Ft
  • $230/SF
  • 41 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1988

  5321 Middle Rd, Winchester, VA 22602

  Discover your dream retreat with this charming all-brick rancher, perfectly situated on 7.47 acres of picturesque landscape, just minutes from town, shopping, and schools. This exceptional property includes an additional parcel with previously approved 1 bedroom perc, offering additional opportunity or buffer space. Step inside to hardwood floors and an traditional layout that boasts a spacious

  Tiffany Hunter ERA Oakcrest Realty, Inc.

  5321 Middle Rd, Winchester, VA 22602
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  /37

  Not Listed For Sale

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

  216 E Piccadilly St, Winchester, VA 22601

  216 E Piccadilly St, Winchester, VA 22601
• 

  

  /50

  $345,000

  • Land
  • 40 Acres
  • $8,582 per Acre

  Mockingbird Lane Lot Unit WP008, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Mockingbird Lane. Features a fully functional hunting cabin with a wood stove and propane used for heating and cooking. The cabin has an open layout and separate sleeping quarters via a loft. Experience exciting

  Chad Pangle

  Mockingbird Lane Lot Unit WP008, Winchester, VA 22603
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  /20

  $1,510 - $1,560 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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  /31

  $328,000 Sold Jun 10, 2025

  • 1,012 Sq Ft
  • $324/SF
  • 55 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1997

  2617 Cornerstone Cir, Winchester, VA 22601

  Seller putting on new roof! Charming 2-bedroom, 1.5-bathroom brick-front home located within the city limits of Winchester. Enjoy outdoor living with a fenced backyard and a screened-in sun porch, perfect for relaxing or entertaining. The oversized one-car garage offers ample storage space. Interior highlights include plantation shutters.Located in a community with a clubhouse, with HOA services

  Sheila Pack RE/MAX Roots

  2617 Cornerstone Cir, Winchester, VA 22601
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  /21

  Est $306,181 Not Listed For Sale

  • Studio
  • 539 Sq Ft

  3464 Papermill Rd, Winchester, VA 22602

  3464 Papermill Rd, Winchester, VA 22602
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  /26

  $245,000

  • Land
  • 23 Acres
  • $10,452 per Acre

  Mockingbird Lane Lot Unit WP007, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Mockingbird Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey and many small game species. There are potential building sites located throughout the

  Chad Pangle

  Mockingbird Lane Lot Unit WP007, Winchester, VA 22603
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  /20

  $1,700 per month

  • 3 Beds
  • 1.5 Baths
  • 1,214 Sq Ft
  • Townhouse for Rent

  403 Chatham Square, Winchester, VA 22601

  Great townhouse at the east side of Winchester, close to the intersection of routes 7 and 81. Easy access to restaurants, pharmacy, grocery stores and gas stations. This property offers 3 bedrooms and one and a half baths. No pets, no smoking in the property; income equal or higher than 4X the monthly rent and 660+ credit required.

  Elcy Pereira Elcy & Co. Realty, LLC.

  403 Chatham Square, Winchester, VA 22601
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  /74

  $724,000 Sold Jun 10, 2025

  • 5,045 Sq Ft
  • $144/SF
  • 13 Days On Market

  • 6 Beds
  • 6 Baths
  • Built 2005

  131 Cahille Dr, Winchester, VA 22602

  Located in the sought-after Raven Pointe neighborhood, this massive brick front colonial is loaded with upgrades and has all of the space you are looking for! This home features 6 bedrooms, 6 full bathrooms, a finished basement with a second full kitchen, and over 5,000 finished sq. ft. on .28 acres. The grand two-story foyer, dual staircase to the upper level, hardwood flooring throughout, and

  Crystal Dudurich ERA Liberty Realty

  131 Cahille Dr, Winchester, VA 22602
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  /2

  Est $230,687 Not Listed For Sale

  • Studio

  128 Rappahannock Trail, Winchester, VA 22602

  128 Rappahannock Trail, Winchester, VA 22602
• 

  

  /31

  $125,000

  • Land
  • 23 Acres
  • $5,383 per Acre

  0 Bear Trail Unit LotWP001 22365692, Winchester, VA 22602

  Idyllic, mostly wooded mountaintop sanctuary made up of three parcels with many residential and recreational possibilities. It is located just a few miles west of Winchester above Shawneeland. The large parcel is part of the Great North Mountain Wilderness community. The soil work on one of the small parcels is approved for a two-bedroom septic system, and the owner has stated that at one time,

  Chad Pangle Whitetail Properties Real Estate

  0 Bear Trail Unit LotWP001 22365692, Winchester, VA 22602
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  /9

  $1,800 - $2,600 per month

  Apartment for Rent

  1-2 Beds

  210 S Cameron St, Winchester, VA 22601

  This fully furnished and recently renovated property is located in the heart off Old Town Winchester and includes a log cabin structure, premium appliances, granite countertops and assigned parking spaces.Come and enjoy the excitement of living in Old Town with many excellent restaurants and drinking establishments , six breweries, multiple music venues, fabulous shopping, museums and art

  210 S Cameron St, Winchester, VA 22601
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  /66

  $690,000 Sold Jun 10, 2025

  • 2,780 Sq Ft
  • $248/SF
  • 251 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2025

  118 Pawn Ct, Winchester, VA 22602

  Quick-Move in with Builder Special financing available! Last Homesite remaining at Abrams! Explore this handsome Amherst home in cul de sac, ready for quick move-in. Included features: a welcoming porch; a large family room with an electric fireplace; a gourmet kitchen offering a roomy pantry and a center island; a spacious living room; an elegant dining room; an airy nook; a convenient laundry;

  Jay Day LPT Realty, LLC

  118 Pawn Ct, Winchester, VA 22602
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  /2

  Est $892,966 Not Listed For Sale

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

  137 W Boscawen St, Winchester, VA 22601

  137 W Boscawen St, Winchester, VA 22601
• 

  

  /32

  $55,559

  • Land
  • 6 Acres
  • $9,546 per Acre

  0 Pack Horse Rd Unit LotWP00E 21685367, Winchester, VA 22603

  Enjoy rural living and fun on this building lot in the Valley Estates community. This land is located off of Pack Horse Road, not far from the West Virginia state line. This prime wooded lot perked for a three-bedroom septic system just recently. Access is secured via road frontage on Pack Horse Road, which is a state-maintained gravel road. Electricity and other utilities are nearby, making for

  Chad Pangle Whitetail Properties Real Estate

  0 Pack Horse Rd Unit LotWP00E 21685367, Winchester, VA 22603
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  /8

  $2,597 per month

  • 4 Beds
  • 3.5 Baths
  • 2,100 Sq Ft
  • Townhouse for Rent

  119 Boone Ct, Winchester, VA 22602

  Be sure to view the Virtual Tour! This brand-new home is currently under construction and offers a complete, modern interior. Featuring 4 bedrooms, 3.5 baths, a 2-car garage, a 10' x 16' composite deck, and a fenced yard. The lower level includes a private bedroom with a full bath and walk-out access. The main level boasts luxury vinyl tile flooring throughout, a beautifully open floor plan, and

  Raj Patel Ikon Realty - Ashburn

  119 Boone Ct, Winchester, VA 22602
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  /45

  $385,000 Sold Jun 09, 2025

  • 1,104 Sq Ft
  • $349/SF
  • 5 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1967

  200 Dogwood Rd, Winchester, VA 22602

  Almost 1 acre off of Rt 7! Close to town! Welcome to this beautifully maintained 3-bedroom, 1.5-bath rancher, ideally situated near Route 7 E, Route 50 E, and I-81—perfect for commuters! This inviting home features a classic brick front, a covered front porch for relaxing mornings, and a screened back porch overlooking the huge fenced backyard—ideal for outdoor gatherings. Inside, you'll find

  Sheila Pack RE/MAX Roots

  200 Dogwood Rd, Winchester, VA 22602
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  /3

  Not Listed For Sale

  2902 Valley Ave, Winchester, VA 22601

  2902 Valley Ave, Winchester, VA 22601
• 

  

  /23

  $168,000

  • Land
  • 10 Acres
  • $16,800 per Acre

  0 Gough Rd Unit LotWP002 20612085, Winchester, VA 22602

  Enjoy rural living and fun on this building lot in the Long Ridge Estates community. This prime building lot is located off of Gough Road in the High View Manor area of the county. This parcel has a septic certification letter on record with the county health department for a four-bedroom septic system. Access is secured via a 50 ft deeded access easement, which has already been installed and

  Chad Pangle Whitetail Properties Real Estate

  0 Gough Rd Unit LotWP002 20612085, Winchester, VA 22602
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  /20

  $2,125 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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  /67

  $490,000 Sold Jun 09, 2025

  • 1,604 Sq Ft
  • $305/SF
  • 0 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1956

  435 Mosby St, Winchester, VA 22601

  You absolutely must see this incredible Brick Ranch home with main level living and full basement! The mountain views are simply stunning. Nicely updated and in a highly desirable location, with just a short walk to Old Town Winchester, schools, and restaurants. This home complete with a newer roof, newer windows, and a newer HVAC system. The kitchen has been beautifully updated with granite

  Angela Duncan MarketPlace REALTY

  435 Mosby St, Winchester, VA 22601
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  /39

  Est $359,827 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  230 Falcon Trail, Winchester, VA 22602

  230 Falcon Trail, Winchester, VA 22602
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  /52

  $495,000

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft

  111 Shelby Ct, Winchester, VA 22602

  Here's a breath of fresh air! Welcome to a beautifully Upgraded and Updated one level home situated on level, fully fenced, cul-de-sac lot and loaded with the WOW factor. Setting the stage for what's to come is the Front Entryway which is a "Knotty Alder Front Door with Sidelights" installed in 2023. Breeze through entry to find desirable open floor plan with vaulted ceiling and dramatic

  Angela Duncan MarketPlace REALTY

  111 Shelby Ct, Winchester, VA 22602
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  /39

  $1,600 per month

  • 2 Beds
  • 1.5 Baths
  • 920 Sq Ft
  • Townhouse for Rent

  527 Gray Ave Unit 2, Winchester, VA 22601

  Unit fully renovated, professionally cleaned and ready for immediate move in. Washer/dryer hook ups in unit, Pets allowed on a case by case basis, Trash, water, sewer and all exterior maintenance included in rent. Owner looking for 640 credit score or better.

  Joshua Jenkins Samson Properties

  527 Gray Ave Unit 2, Winchester, VA 22601
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  /69

  $512,552 Sold Jun 06, 2025

  • 2,028 Sq Ft
  • $253/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1940

  256 Parkway St, Winchester, VA 22601

  Picturesque on Parkway - If you’ve been looking for the beauty and bones of an older home that has been updated tastefully, respecting the original charm, look no further. As you step into this immaculate 1940 colonial, you will be greeted with beautiful hardwood floors running throughout the main living area. The living room boasts built in bookshelves that run to the ceiling and tall windows

  Danielle Spriggs ICON Real Estate, LLC

  256 Parkway St, Winchester, VA 22601
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  /38

  Est $303,553 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,380 Sq Ft

  1172 Purcell Ln, Winchester, VA 22603

  1172 Purcell Ln, Winchester, VA 22603

Showing Results 81 - 120, Page 3 of 18