Winchester, VA Homes

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  /66

  $1,200,000

  • Land
  • 124 Acres
  • $9,677 per Acre

  0 Frog Hollow Rd Unit LotWP001, Winchester, VA 22603

  Here’s a piece of pristine land on the market for the first time since the late 70’s with nearly endless possibilities for the next owner(s). This property is located north of Winchester and very near the West Virginia line. This prime piece of real estate has been family-owned and operated for decades. It is a mix of mostly flat hay ground and wooded acreage that stretches to the top

  Chad Pangle Whitetail Properties Real Estate

  0 Frog Hollow Rd Unit LotWP001, Winchester, VA 22603
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  /40

  $2,900 per month

  • 5 Beds
  • 3 Baths
  • House for Rent

  220 Munsee Cir, Winchester, VA 22602

  Discover an exquisite opportunity to lease a brand-new contemporary residence in the prestigious Abrams Pointe community, available from November 4, 2025. This stunning 5-bedroom, 4-bathroom home boasts an open floor plan that seamlessly integrates the living, dining, and kitchen areas, perfect for entertaining. The gourmet kitchen features a spacious island, ENERGY STAR appliances, and a

  Sridevi Miriyala Maram Realty, LLC

  220 Munsee Cir, Winchester, VA 22602
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  /47

  $295,000 Sold Nov 03, 2025

  • 780 Sq Ft
  • $378/SF
  • 22 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1955

  2964 Grace St, Winchester, VA 22601

  Wonderful Light filled 2 story Mid-Century Bungalow Updated for Modern Living while Maintaining its Original Charm and Style. An inviting Front Porch with Fabulous Wood Floors runs the length of the front of the home. Enter and Enjoy Beautiful Laminate Plank Floors and Arched Doorways and Recessed Lighting throughout the Main Floor. The Eat In Kitchen maintains it’s Cottage Core Aesthetic. 2

  Jane Norton United Real Estate

  2964 Grace St, Winchester, VA 22601
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  /25

  Est $367,961 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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  /41

  $77,700

  • Land
  • 6.09 Acres
  • $12,759 per Acre

  440 Iris Ln, Winchester, VA 22602

  Owner Financing Available! (see details below)Enjoy breathtaking, unrivaled views of the Shenandoah Valley below from this ridgetop property on Little North Mountain.Property Overview:Address: 440 Iris Lane, Winchester, VA 22602Size: 6.09 AcresKey Features:Gorgeous Sunset Valley ViewsTwo Lots in One Build on Both or Split Off!Extensive Road

  Robert Scott AcreTown.com

  440 Iris Ln, Winchester, VA 22602
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  /9

  $1,325 per month

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

  45 Race St Unit 45, Winchester, VA 22601

  Brand new renovation to market, this 2 bed 1 bath apartment has been fully updated with all new kitchen, bath, flooring, appliances and laundry in unit! Unbeatable for the price! Call or email to schedule a tour today!

  45 Race St Unit 45, Winchester, VA 22601
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  /35

  $403,000 Sold Nov 03, 2025

  • 1,993 Sq Ft
  • $202/SF
  • 6 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2008

  277 McDonald Rd, Winchester, VA 22602

  Beautifully updated 3-bedroom, 2.5-bath home just minutes from Winchester Medical Center and I-81. This move-in-ready property combines timeless charm with modern upgrades throughout. Step into the spacious main level featuring fresh paint, newer carpet, and a bright, updated kitchen with new cabinets and an island bar perfect for entertaining. Upstairs, the primary suite offers a walk-in closet

  christine ruffner Morris & Co. Realty, LLC

  277 McDonald Rd, Winchester, VA 22602
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  /22

  Est $294,459 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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  /60

  $395,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,582 Sq Ft

  859 Brush Creek Rd, Winchester, VA 22603

  This rustic home on acreage is located north of Winchester in the Cross Junction area of the county. On the market for the first time since the 1950’s the home features 3 bedrooms, 1 bathroom, and nearly 1600 +/- square feet of living space. Access is secured via extensive road frontage on paved and state maintained Brush Creek Road. Electricity, well, and septic are already installed

  Chad Pangle Whitetail Properties Real Estate, LLC

  859 Brush Creek Rd, Winchester, VA 22603
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  /11

  $1,700 per month

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Condo for Rent

  302 N Kent St, Winchester, VA 22601

  Experience the charm of this beautifully renovated 3-bedroom, 2-bathroom Colonial apartment, set to unveil in 2025. Nestled in a serene environment, this unit boasts a timeless brick exterior and a thoughtfully designed layout that exudes warmth and comfort. Enjoy the convenience of in-unit washer and dryer hookups, ensuring effortless laundry days. The property offers an exclusive lifestyle with

  Brandon Pifer Pifer Realty, LLC

  302 N Kent St, Winchester, VA 22601
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  /42

  $549,000 Sold Nov 03, 2025

  • 2,772 Sq Ft
  • $198/SF
  • 3 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1996

  234 Asbury Rd, Winchester, VA 22602

  Welcome to 234 Asbury Rd, Winchester, VA 22602 – a stunning brick-front residence nestled in the established and sought-after Pioneer Heights community. This spacious home offers over 2,700+ square feet of beautifully finished living space, thoughtfully designed with both entertaining and everyday comfort in mind. The main level showcases a traditional layout with gleaming hardwood flooring,

  Lisa Behr Coldwell Banker Premier

  234 Asbury Rd, Winchester, VA 22602
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  /29

  Est $304,146 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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  /80

  $650,000

  • 5 Beds
  • 3.5 Baths
  • 3,552 Sq Ft

  2708 Cassidy Ct, Winchester, VA 22601

  Rolling Hills Estates located in the Winchester City area, this beautifully maintained 5-bedroom, 3.5-bath home offers 3,552 sq ft of finished living space on a .35-acre cul-de-sac lot. Featuring a 3-car garage w/220 Car Charger, fully fenced backyard, covered front porch, and a rear Trex deck with lighting and stairs to the yard, this home is built for comfortable living and entertaining.

  Geri Deane Hunt Country Sotheby's International Realty

  2708 Cassidy Ct, Winchester, VA 22601
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  /13

  $1,400 per month

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

  542 N Loudoun St Unit A, Winchester, VA 22601

  542 N Loudoun St Unit A, Winchester, VA 22601
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  /2

  $1,400,000 Sold Nov 03, 2025

  • Land
  • 5 Acres
  • $280,000 per Acre

  • 46 Days On Market

  260 Costello, Winchester, VA 22601

  Five acres of B2 land near Costco, Army Corp of Engineers, Frederick Country Public Safety Building, and the new One Logistics Park commercial center. An adjacent parcel of ten acres is available for sale for a combined parcel of 15 acres. Perfect for a large-scale commercial development.

  Jason Aikens RE/MAX Roots

  260 Costello, Winchester, VA 22601
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  /31

  Est $266,819 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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  /43

  $564,900

  • 3 Beds
  • 4 Baths
  • 2,489 Sq Ft

  687 Woodland Ave, Winchester, VA 22601

  Experience refined living in this stunning two-level brick residence, designed with an open-concept layout that seamlessly blends sophistication and comfort. The home features 4 spacious bedrooms, each with a private full bathroom.The kitchen boasts granite countertops and elegant finishes, flowing effortlessly into the dining and living areas — perfect for entertaining or relaxing by the gas

  Mauricio Argandona Fairfax Realty Select

  687 Woodland Ave, Winchester, VA 22601
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  /11

  $1,800 per month

  • 3 Beds
  • 1.5 Baths
  • 1,250 Sq Ft
  • House for Rent

  557 Eagle Dr, Winchester, VA 22601

  Discover a charming retreat in this beautifully maintained ranch-style home, exuding warmth and comfort. Built in 1960, this detached gem features three spacious bedrooms and one and a half bathrooms, perfect for those seeking a blend of classic design and modern living. Step inside to find a welcoming atmosphere, where natural light dances through the windows, illuminating the inviting spaces.

  Brandon Pifer Pifer Realty, LLC

  557 Eagle Dr, Winchester, VA 22601
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  /45

  $366,500 Sold Nov 03, 2025

  • 1,272 Sq Ft
  • $288/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  146 Sunshine Dr, Winchester, VA 22602

  Perfect and adorable 3-bedroom, 2-bath home! Step in from your covered carport—ideal for keeping the weather off your car—into a spacious mudroom with a washer and dryer that convey (only 2 years old!), cabinets for storage, and a convenient utility sink. The kitchen has been freshly painted, and features upgraded countertops, a stylish backsplash, and tile flooring. The open floor plan flows

  Brandi Marcum Pearson Smith Realty, LLC

  146 Sunshine Dr, Winchester, VA 22602
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  /19

  Est $320,609 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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  /34

  $514,000

  • 3 Beds
  • 2.5 Baths
  • 1,978 Sq Ft

  236 Miller St, Winchester, VA 22601

  Charming 3 Bedroom, 2.5 Bath Colonial just blocks from Old Town Winchester, offering easy access to dining, entertainment, and shopping! Enjoy outdoor living on the spacious covered front porch or in the fenced backyard. The landscaping features beautiful lilac and rose bushes. The eat-in kitchen features granite countertops, a tile backsplash, hardwood floors, and newer stainless steel

  Sheila Pack RE/MAX Roots

  236 Miller St, Winchester, VA 22601
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  /2

  $1,400 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Townhouse for Rent

  382 Woodstock Ln, Winchester, VA 22601

  This property at 382 Woodstock Ln features 2 bedrooms and 1 bathroom within a total living space of 1,000 square feet. The living room offers ample space for relaxation and entertainment. The bathroom includes a tub/shower combination for convenience. Each bedroom is designed to accommodate various furniture arrangements and provides adequate closet space. Additional amenities include storage

  382 Woodstock Ln, Winchester, VA 22601
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  /25

  $300,000 Sold Nov 03, 2025

  • 1,710 Sq Ft
  • $175/SF
  • 23 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1962

  428 Imperial St, Winchester, VA 22601

  Enjoy the ease of one-level living in the heart of Winchester City thats ready for your personal touches! Ideally located just minutes from shopping, dining, and local conveniences, this charming all-brick rancher with a full walk-up basement offers both comfort and functionality. The kitchen features space for a dining table, while the inviting living room boasts a cozy fireplace with a lovely

  Leah Clowser RE/MAX Roots

  428 Imperial St, Winchester, VA 22601
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  /8

  Est $242,364 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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  /95

  $660,000

  • 4 Beds
  • 3.5 Baths
  • 4,101 Sq Ft

  608 Kernstown Ct, Winchester, VA 22601

  Discover the charm and serenity of suburban living at 608 Kernstown Court, nestled in the storied landscape of Winchester, Virginia. This picturesque address offers an ideal blend of history, convenience, and modern comfort, an inviting sanctuary for families, professionals, or anyone seeking a peaceful yet well connected lifestyle.This desirable property features a beautifully appointed

  Aaron Richert Realty FC, LLC

  608 Kernstown Ct, Winchester, VA 22601
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  /30

  $1,650 per month

  • 3 Beds
  • 1.5 Baths
  • 1,080 Sq Ft
  • Townhouse for Rent

  211 Kimberly Way, Winchester, VA 22601

  Two level townhouse with 3 bedrooms and one and a half bathroom

  Jose Barrientos JB Home Realty LLC

  211 Kimberly Way, Winchester, VA 22601
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  /38

  $425,000 Sold Nov 03, 2025

  • 1,588 Sq Ft
  • $268/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1997

  110 Clevenger Ct, Winchester, VA 22601

  Highest and best offer due by 9/30/25 at 7:00pm.Welcome to this well-maintained 3-bedroom, 2-bath ranch home offering main-level living on a private lot at the end of a cul-de-sac. Prime location—just minutes to shopping, restaurants, schools, Winchester Medical Center, and Old Town Winchester Walking Mall, yet just outside the city limits. A traditional-style home with a living room and

  RoxAnn Grimes RE/MAX Roots

  110 Clevenger Ct, Winchester, VA 22601
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  /22

  Est $247,350 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 765 Sq Ft

  514 Armour Dale, Winchester, VA 22601

  514 Armour Dale, Winchester, VA 22601
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  /116

  $599,900

  • 3 Beds
  • 1.5 Baths
  • 2,874 Sq Ft

  510 S Washington St, Winchester, VA 22601

  Welcome to a piece of Winchester History. This historic Colonial Revival residence, built of enduring brick construction, offers an opportunity of owning a significant piece of the city's heritage. Situated on a .20 city acre lot, this property is ideally positioned directly on the route of the Shenandoah Apple Blossom Festival Parade, offering unparalleled viewing opportunities.With winter

  Laurie Webber Century 21 Modern Realty Results

  510 S Washington St, Winchester, VA 22601
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  /19

  $2,300 per month

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft
  • Townhouse for Rent

  152 Munsee Cir, Winchester, VA 22602

  Move in ready 3-level townhome available for immediate lease. This gorgeous Adams model built by DR Horton offers 4 bedrooms, 3.5 baths, with a 1-car garage. The kitchen features stainless steel appliances, granite countertops and family room off the kitchen. Open floor plan with 1/2 bath in the second level feel adequate to hang with friends and family. Have access to deck from kitchen to enjoy

  Ujjwal Shrestha Signature Realtors Inc

  152 Munsee Cir, Winchester, VA 22602
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  /57

  $625,000 Sold Oct 31, 2025

  • 4,787 Sq Ft
  • $131/SF
  • 5 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2007

  101 Arthur Ln, Winchester, VA 22602

  Stunning 5BR, 4BA Colonial with nearly 4,800 sq ft of beautifully finished space on three levels, loaded with upgrades and move-in ready! Enjoy brand new carpet upstairs and fresh paint throughout the main and upper levels, creating a bright and inviting feel. Main level features hardwood floors, 9-ft ceilings, a spacious family room with gas fireplace, and a sunroom with vaulted ceilings. The

  Scotti Sellers Compass

  101 Arthur Ln, Winchester, VA 22602
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  /71

  Est $337,701 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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  /49

  $623,790

  • 3 Beds
  • 3 Baths
  • 3,200 Sq Ft

  0 Magpie Ln Unit VAFV2037494, Winchester, VA 22603

  Discover new 55+ SINGLE FAMILY HOMES by Van Metre Homes at Hiatt Pointe (55+) in Winchester, VA that will be ready for you to move in 2026. Step into the Sierra 39-F2 at Hiatt Pointe—a two-car, front-load garage single family home with up to four bedrooms and three full bathrooms. Designed for ease and everyday function, this floorplan welcomes you with a charming front porch and

  Shannon L Bray Pearson Smith Realty, LLC

  0 Magpie Ln Unit VAFV2037494, Winchester, VA 22603
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  /16

  $1,595 per month

  • 1 Bed
  • 1 Bath
  • 1,024 Sq Ft
  • House for Rent

  219 Millwood Ave Unit 2, Winchester, VA 22601

  Live in a piece of Historic Winchester! This fabulous and spacious four bedroom, two bath home in downtown Winchester was built in 1868 and is totally updated. You get the charm of old town Winchester and all the modern conveniences! Walkable to everything. This recently renovated home is clean, bright, and ready for you. Great kitchen and in unit laundry. Just a quick walk to Shenandoah

  Amanda White Nova Home Hunters Realty

  219 Millwood Ave Unit 2, Winchester, VA 22601
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  /43

  $295,500 Sold Oct 31, 2025

  • 1,604 Sq Ft
  • $184/SF
  • 6 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1994

  206 Barrington Ln, Winchester, VA 22601

  Welcome home to this inviting three-level townhome with plenty of space and comfort. The open family and dining area features classic columns, hardwood floors, and a bright bay window that adds lots of natural light. The kitchen offers a handy pass-through, walk-in pantry, and luxury vinyl plank flooring. Upstairs you’ll find a spacious primary bedroom with a walk-in closet, a second bedroom, and

  Laura White ERA Oakcrest Realty, Inc.

  206 Barrington Ln, Winchester, VA 22601
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  /46

  Est $513,586 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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  /29

  $409,900

  • 3 Beds
  • 2.5 Baths
  • 1,962 Sq Ft

  117 Tye Ct, Winchester, VA 22602

  Modern Townhome with Premium Upgrades. Great for Investor as it is currently rented. Ideally located just outside the bustle of Winchester with an easy commute to the DC Metro area, this 2023-built townhome offers the perfect balance of comfort, convenience, and style. Freshly and professionally painted throughout, the home features an open-concept main level with durable LVP flooring, granite

  Rick Cockrill Keller Williams Realty

  117 Tye Ct, Winchester, VA 22602
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  /24

  $1,450 per month

  • 2 Beds
  • 1.5 Baths
  • 1,010 Sq Ft
  • Townhouse for Rent

  214 Waterford Ln, Winchester, VA 22602

  This charming 2-bedroom, 1.5-bathroom home at 214 Waterford Ave in Winchester, VA, offers the perfect blend of classic character and modern amenities. The spacious living area features beautiful hardwood floors, and the kitchen is equipped with plenty of storage. The generously sized bedrooms provide comfort and convenience, while the large backyard with a deck is ideal for outdoor relaxation and

  Rachel Olsen Keller Williams Realty

  214 Waterford Ln, Winchester, VA 22602
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  /65

  $600,000 Sold Oct 31, 2025

  • 3,283 Sq Ft
  • $183/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  231 Gun Barrel Ln, Winchester, VA 22603

  Spectacular, move-in ready rancher on over 6 acres. Completely remodeled within the past 3 years with all appliances, HVAC systems, roof, flooring and more less than 3 years old. The home offers a beautiful new kitchen with upgraded cabinets and quartz countertops. All bathrooms have also been completely updated with top-of-the-line vanities, tile and flooring. The lower level is finished into

  Dennis Virts RE/MAX Distinctive Real Estate, Inc.

  231 Gun Barrel Ln, Winchester, VA 22603
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  /67

  Est $524,271 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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