37

Winchester, VA Homes for Sale under $100,000

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  • /10

    $61,900

    • Land
    • 0.69 Acre
    • $89,710 per Acre

    Lots 4 & 5 Glen Ridge Rd, Winchester, VA 22602

    Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for

    Agent Photo

    Bradley Comstock

    ERA Oakcrest Realty, Inc.

    (540) 402-9785

    Lots 4 & 5 Glen Ridge Rd, Winchester, VA 22602
  • /11

    $61,900

    • Land
    • 0.69 Acre
    • $89,710 per Acre

    Lots 14 & 15 Glen Ridge Rd, Winchester, VA 22602

    Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for

    Agent Photo

    Bradley Comstock

    ERA Oakcrest Realty, Inc.

    (540) 712-6303

    Lots 14 & 15 Glen Ridge Rd, Winchester, VA 22602
  • /11

    $51,900

    • Land
    • 0.34 Acre
    • $152,647 per Acre

    Lot 10 Glen Ridge Rd, Winchester, VA 22602

    Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for

    Agent Photo

    Bradley Comstock

    ERA Oakcrest Realty, Inc.

    (540) 732-7734

    Lot 10 Glen Ridge Rd, Winchester, VA 22602
  • /11

    $61,900

    • Land
    • 0.69 Acre
    • $89,710 per Acre

    Lots 11 & 12 Glen Ridge Rd, Winchester, VA 22602

    Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for

    Agent Photo

    Bradley Comstock

    ERA Oakcrest Realty, Inc.

    (540) 698-4594

    Lots 11 & 12 Glen Ridge Rd, Winchester, VA 22602
  • /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
  • /6

    $24,900

    • Land
    • 0.47 Acre
    • $52,979 per Acre

    Lot 162 Bobcat Trail, Winchester, VA 22602

    Perched atop Great North Mountain, this beautiful wooded lot offers the potential for stunning westerly mountain views. Just under half an acre, the property offers a small driveway already cut in and a level homesite area, an ideal setting for your future mountain retreat, whether a chalet, cabin, or full-time residence. Enjoy privacy, nature, and elevated views while still being approximately

    Natasha Roberts Realty ONE Group Old Towne

    Lot 162 Bobcat Trail, Winchester, VA 22602
  • /11

    $90,000

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    152 Fiddler Ave Unit C318, Winchester, VA 22603

    Welcome to Regency Lakes a all age active and vibrant community, where you can find yourself in your dream home. We have updated 2001 3 bed, 2 bath home featuring a large open floor plan. Step inside to find a bright and airy open floor plan, stone wood burning fireplace and updated bathrooms. The spacious kitchen boasts a multi level center island and a pass through, perfect for both everyday

    Kristina Kelly Regency Lakes

    152 Fiddler Ave Unit C318, Winchester, VA 22603
  • /11

    $34,900

    • Land
    • 0.81 Acre
    • $43,086 per Acre

    Lot 9, 11, 13 Cougar Trail, Winchester, VA 22602

    Tucked into the scenic mountains of Wilde Acres subdivision, this 0.81-acre offering combines three wooded lots into one unique opportunity for your future homesite or getaway retreat. Surrounded by mature trees and natural beauty, the property offers privacy, flexibility, and the potential to build in a peaceful setting away from the noise of town. Whether you're looking to create a full-time

    Brad Cohen Connexa Real Estate

    Lot 9, 11, 13 Cougar Trail, Winchester, VA 22602
  • /4

    $9,500

    • Land
    • 0.25 Acre
    • $38,000 per Acre

    Lot 5 Quail, Winchester, VA 22602

    Discover a serene 0.25-acre lot nestled in Winchester's Wilde Acres subdivision, where nature meets tranquility. This beautifully wooded parcel offers a perfect canvas for your dream home, surrounded by lush trees that provide both privacy and a picturesque backdrop. With convenient road frontage, access to your future home or cozy weekend retreat is effortless. The enchanting views of the

    Bridget Aikens Colony Realty

    Lot 5 Quail, Winchester, VA 22602
  • /4

    $9,500

    • Land
    • 0.25 Acre
    • $38,000 per Acre

    Lot 6 Quail Dr, Winchester, VA 22602

    Discover a serene 0.25-acre lot nestled in Winchester's Wilde Acres subdivision, where nature meets tranquility. This beautifully wooded parcel on Quail Drive offers a perfect canvas for your dream home, surrounded by lush trees that provide both privacy and a picturesque backdrop. With convenient road frontage, access to your future home or cozy weekend retreat is effortless. The

    Bridget Aikens Colony Realty

    Lot 6 Quail Dr, Winchester, VA 22602
  • /3

    $6,500

    • Land
    • 0.26 Acre
    • $25,000 per Acre

    0 Fox Trail Unit VAFV2040348, Winchester, VA 22602

    Vacant lot on Fox Trail in Wilde Acres! This is raw land, no perc test has been done. Affordable and at the top, for lots of views of North Mountain. Private - not many homes around this lot. Sign on Property

    Traci Shoberg Samson Properties

    0 Fox Trail Unit VAFV2040348, Winchester, VA 22602
  • /9

    $9,500

    • Land
    • 0.55 Acre
    • $17,273 per Acre

    LOTS 8 & 9 Elk Trail, Winchester, VA 22602

    Great opportunity to own two beautiful wooded lots full of mature trees and plenty of privacy! These adjoining parcels offer a wonderful chance to connect with nature and enjoy peaceful surroundings. Located just about 30 minutes from downtown Winchester, you get the perfect mix of country calm and town convenience. Whether you’re thinking about outdoor fun, future plans, or simply an investment,

    Kristin Crosby Samson Properties

    LOTS 8 & 9 Elk Trail, Winchester, VA 22602
  • /4

    $44,999

    • Land
    • 1.35 Acres
    • $33,333 per Acre

    129 Huntcrest Cir, Winchester, VA 22602

    2 lots in 1 Sale! These vacant lots offer an excellent opportunity to build your future home or make a smart investment. Situated in a desirable neighborhood, the combined 1.35 acres feature wooded terrain and public utilities available. Enjoy a peaceful setting while remaining conveniently located near shopping, dining, schools, and major highways, providing easy access to city amenities.

    Joel Hinckley PlatLabs, LLC

    129 Huntcrest Cir, Winchester, VA 22602
  • /5

    $10,000

    • Land
    • 0 Acre

    Lot 13 Tomahawk Trai 0, Winchester, VA 22602

    Welcome to Shawneeland! This mountain community is tucked away in a rural setting and a short distance to shopping, restaurants and Winchester's Historic Downtown. Utilize this 0.48 acre lot as a potential building lot, recreational space or enjoy the amenities such as Lake Cherokee with a beach area, fishing and picnic areas. Purchaser to verify location of boundary lines.

    Kim Hurst MarketPlace REALTY

    Lot 13 Tomahawk Trai 0, Winchester, VA 22602
  • /10

    $75,900

    • 3 Beds
    • 2 Baths
    • 1,136 Sq Ft

    212 Artifact Ave Unit 429, Winchester, VA 22603

    Welcome to Regency Lakes an all age]active and vibrant community, where you can find yourself in your dream home. We have a stunning, 2016 3 bed, 2 bath home for sale featuring a wonderful open floor plan. Located in Winchester, this property offers the perfect blend of modern amenities and timeless charm. Step inside to find an impeccably maintained home featuring new flooring throughout. The

    Kristina Kelly Regency Lakes

    212 Artifact Ave Unit 429, Winchester, VA 22603
  • /13

    $85,000

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    108 Dwayne Place Unit A135, Winchester, VA 22603

    Welcome to Regency Lakes a all age active and vibrant community, where you can find yourself in your dream home. We have a beautiful, well maintained 1995 3 bed, 2 bath home featuring 1512.00 sq ft of beautifully designed living space, New carpeting throughout, and new garden tub. Located Winchester, this property offers the perfect blend of modern amenities and timeless charm. Step inside to

    Kristina Kelly Regency Lakes

    108 Dwayne Place Unit A135, Winchester, VA 22603
  • /10

    $17,500

    • Land
    • 0.27 Acre
    • $64,815 per Acre

    Lot 18 Pheasant Dr, Winchester, VA 22602

    Talk about Location! Situated in Scenic Mountain Falls (Wilde Acres) It's beautiful & peaceful with mountain views coming and going. Enjoy the amenities of the community, Recreational Park, Pond, Picnic Pavilion Playground & more. Build a full or part time home on this rather level .27 acre lot. Certification Letter - 3 bedroom Perc. Short Distance to Schools, Rt 50, Shopping, Hospital, Downtown

    Gina Griffith MarketPlace REALTY

    Lot 18 Pheasant Dr, Winchester, VA 22602
  • /22

    $79,900

    • 3 Beds
    • 2 Baths
    • 1,118 Sq Ft

    107 Smith Dr, Winchester, VA 22603

    Resort-Style Living at Regency Lakes! Enjoy an amenity-rich community that also offers easy access to route 7 and many shopping and dining options nearby. The home features vinyl flooring in the main living areas and carpet in the bedrooms. A light and bright kitchen is the heart of the home, with plenty of storage and counterspace. A charming breakfast nook and laundry closet add convenience to

    Heloisa Amar Samson Properties

    107 Smith Dr, Winchester, VA 22603
  • /12

    $80,000

    • Land
    • 0.13 Acre
    • $615,385 per Acre

    520 Highland Ave, Winchester, VA 22601

    Empty lot ready to build a home one. The lot is fully fenced with front and rear gates. The front of the lot meets the sidewalks and road of Highland Ave. The rear of the lot meets a gravel alley way that could give access to off street parking on this lot. Homes in the city are in demand, so don't miss this opportunity. Zoned HR-1Can only be used for single family dwellingsFront setback:

    Michael Sprague Samson Properties

    520 Highland Ave, Winchester, VA 22601
  • /11

    $80,000

    • Land
    • 0.08 Acre
    • $1,000,000 per Acre

    24 N Pleasant Valley Rd, Winchester, VA 22601

    Ready for building! Clear open lot that is ready for a home to be built. Winchester City is the fastest growing city in the state and homes are in high demand. Don't miss your opportunity. Property has road front access as well as a gravel alley in the rear that could be used for access to off street parking.Zoned MR - medium density residential districtCan only be used for single family

    Michael Sprague Samson Properties

    24 N Pleasant Valley Rd, Winchester, VA 22601
  • /12

    $16,000

    • Land
    • 0.26 Acre
    • $61,538 per Acre

    Lot 23 Panther Dr, Winchester, VA 22602

    Nestled in the tranquil community of Wilde Acres, this partially cleared, .26 acre lot offers endless potential for your dream home. Enjoy the serenity of nature while still being just a short drive from local amenities, the perfect balance of peace and convenience. Whether you’re looking for a weekend retreat or a full-time residence, this property provides the ideal setting to make your vision

    Amanda Toothman Dandridge Realty Group, LLC

    Lot 23 Panther Dr, Winchester, VA 22602
  • /2

    $12,800

    • Land
    • 0.4 Acre
    • $32,000 per Acre

    0 Budwood Trail Unit 11620368, Winchester, VA 22602

    Nice level corner wooded lot. Corner of Budwood and Rockwood Follow your GPS to the corner point. All measurements are taken from government sources. Such as the actual .4. acres is actually .398 acres rounded up.

    John Holsinger JOHN S HOLSINGER REAL ESTATE BROKER LLC

    0 Budwood Trail Unit 11620368, Winchester, VA 22602
  • /24

    $25,000

    • Land
    • 1.43 Acres
    • $17,483 per Acre

    LOT 5A Fox Trail, Winchester, VA 22602

    Beautiful building lot located in Mountain Falls Park – Wilde Acres. This is the last lot on the right on Fox Trail, offering excellent privacy and seclusion. The property backs to permanent open space, providing a peaceful setting with mountain views and abundant wildlife. Approved for a 3-bedroom septic system with a certification letter on file. A current survey is also available. This is an

    Nadeem Helfer Samson Properties

    LOT 5A Fox Trail, Winchester, VA 22602
  • /12

    $28,000

    • Land
    • 0.71 Acre
    • $39,437 per Acre

    0 Inca Lot 209 Trail, Winchester, VA 22602

    Lot 209 on Inca Trail is a rare find at nearly 3⁄4 of an acre, a gently sloping, treed lot on the northeastern side of Great North Mountain in the quiet community of Shawneeland. Build your weekend getaway or your full-time residence. It’s a quick trip to Winchester, VA, a vibrant community with a walking mall, multiple shopping areas, a regional medical center, Shenandoah University, and

    Rebecca McTavish Long & Foster Real Estate, Inc.

    0 Inca Lot 209 Trail, Winchester, VA 22602
  • /21

    $99,900

    • Land
    • 0.65 Acre
    • $153,692 per Acre

    222 Siler Ln, Winchester, VA 22603

    UPDATE--NEW PRICE. Seller says SELL...UNRESTRICTED LAND and a BRAND NEW WELL installed by SHIRLEY WELL DRILLING - 11 GPM. SELLING AT ASSESSED VALUE for 2025 ($83,000.00) plus cost of well ($ 16,900) Engineering report complete for drain field and all conveys $1,450.00 value- conveys. New Survey done -$800,00 Value-The lot has been leveled for a beautiful home site (cost $ 16,000.,00).

    Erick Erdal Long & Foster Real Estate, Inc.

    222 Siler Ln, Winchester, VA 22603
  • /12

    $12,500

    • Land
    • 0.29 Acre
    • $43,103 per Acre

    155 Hawk Trail, Winchester, VA 22602

    Lot 155 on Hawk Trail , is located in the mountainous residential community of Shawneeland, just 12 miles from Winchester, VA. Enjoy the fresh mountain air, hiking, fishing and swimming in Lake Cherokee in this idyllic setting. Know, however, that you are close to Winchester Medical Center, the Museum of the Shenandoah Valley, and an abundance of restaurants and shopping opportunities. Build a

    Rebecca McTavish Long & Foster Real Estate, Inc.

    155 Hawk Trail, Winchester, VA 22602
  • /15

    $39,000

    • Land
    • 1.53 Acres
    • $25,490 per Acre

    Lot 10,11,12-13 A 60 Fox Trail, Winchester, VA 22602

    Attention Builders! 4 Pack of contiguous building lots in Wilde Acres -Mountain Falls Park, you have the opportunity to construct your very own mountain top retreat. Mountain Falls Park is conveniently located, just a short drive away from Stephens City or downtown Winchester, VA, providing an easy commute while still offering the seclusion and serenity of the mountains. Immerse yourself in

    Nadeem Helfer Samson Properties

    Lot 10,11,12-13 A 60 Fox Trail, Winchester, VA 22602
  • /12

    $17,000

    • Land
    • 0.38 Acre
    • $44,737 per Acre

    Lot 231 Timber Ridge, Winchester, VA 22602

    This lot is located in the Shawneeland community of northwestern Frederick County, Virginia on the western-facing slope of Great North Mountain. Level and partially treed, it's a spectacular place to build your weekend getaway cabin or year-round home. Swim in Shawneeland's spring-fed lake, fish, hike, and picnic, or simply enjoy the quiet beauty of nature. Located just 12 miles from

    Rebecca McTavish Long & Foster Real Estate, Inc.

    Lot 231 Timber Ridge, Winchester, VA 22602
  • /9

    $17,000

    • Land
    • 0.5 Acre
    • $34,000 per Acre

    Lot 111 Cub Trail, Winchester, VA 22602

    Tired of the bustle of city life? Visit Shawneeland in northwestern Frederick County, Virginia. Visit for a day and stay for a lifetime. This mountaintop lot on the western slope is just the place to build a home. Enjoy Shawneeland's amenities: a spring-fed lake perfect for swimming and fishing, a playground for the children, and hiking trails for the entire family.Love the country but want

    Rebecca McTavish Long & Foster Real Estate, Inc.

    Lot 111 Cub Trail, Winchester, VA 22602
  • /9

    $17,000

    • Land
    • 0.42 Acre
    • $40,476 per Acre

    Lot 76 Bear Trail, Winchester, VA 22602

    Looking for a lot in a quiet, rural development where you can enjoy the beauty of nature, listen to the birds, and view an occasional wild turkey or deer? This undeveloped lot in Shawneeland may be just the place for you. With its spring-fed lake, great for fishing or swimming, and mountain trails, Shawneeland is the perfect place to build a getaway retreat or a full-time residence. Located

    Rebecca McTavish Long & Foster Real Estate, Inc.

    Lot 76 Bear Trail, Winchester, VA 22602
  • /6

    $40,000

    • Land
    • 1.38 Acres
    • $28,986 per Acre

    105 Arum Trail, Winchester, VA 22602

    Welcome to your buildable, oversized 1.38 acre lot in Duck Run. Ready for your forever home? Come check this property out! No utilities on property. Blank slate ready for all your design ideas.

    Cat Haines Cedar Creek Real Estate

    105 Arum Trail, Winchester, VA 22602
  • /6

    $20,000

    • Land
    • 0.46 Acre
    • $43,478 per Acre

    Lot 102 Bow Wood Trail, Winchester, VA 22602

    A Hidden Gem Waiting for YouNestled in the serene countryside of Winchester, Virginia, lies a great treed building lot on the lower side of Shawneeland. This picturesque piece of land offers the perfect blend of seclusion and convenience, making it an ideal location for building your dream home.Enjoy the tranquility and natural beauty of Shawneeland's private parks, perfect for relaxing

    Rick Guthrie Keller Williams Realty

    Lot 102 Bow Wood Trail, Winchester, VA 22602
  • /6

    $12,900

    • Land
    • 0.25 Acre
    • $51,600 per Acre

    Lot 17 Fox Trail, Winchester, VA 22602

    Are you looking for an affordable approved building lot under 20 minutes to Winchester Medical Center I 81 or I 66 and an overwhelming sense of nature with unparalleled mountain views? Look no further! Mountain Falls Park is known for its close proximity to town, waterfalls, views for miles and a quiet community. This lot is very buildable it is level, has a current survey, recorded plat and a

    Nadeem Helfer Samson Properties

    Lot 17 Fox Trail, Winchester, VA 22602
  • /2

    $69,900

    • Land
    • 0.19 Acre
    • $367,895 per Acre

    Lot 84 Purcell Ln, Winchester, VA 22603

    Build Your Vision Near Winchester City LimitsPrime buildable lot offering the perfect balance of convenience and freedom. Located just minutes from Winchester City but still in county, shopping, the hospital, and Route 37, this property is ready for your project with public water and sewer hookups available. Freedom to Build: No HOA or restrictive covenants—ideal for a custom small home or a

    Jim Thomson Realty ONE Group Old Towne

    Lot 84 Purcell Ln, Winchester, VA 22603
  • /2

    $39,900

    • Land
    • 0.45 Acre
    • $88,667 per Acre

    Lot 205 Rockwood Trail, Winchester, VA 22602

    Offers the best views of the valley. Beautiful lot (almost 1/2 acre) with valley views of Shenandoah waiting for your clients to build your new home on or buy and hold. Perfect for those who want privacy and view. Great for primary home or weekend retreat. Cert Letter 3 bedroom perk..

    Jim Thomson Realty ONE Group Old Towne

    Lot 205 Rockwood Trail, Winchester, VA 22602
  • /2

    $3,500

    • Land
    • 0.25 Acre
    • $14,000 per Acre

    107 Fox Trail, Winchester, VA 22602

    Babak Taghavi Venture Realty

    107 Fox Trail, Winchester, VA 22602
  • /2

    $8,500

    • Land
    • 0 Acre

    0 0 Unit VAFV2036674, Winchester, VA 22602

    Kelly Hayes Samson Properties

    0 0 Unit VAFV2036674, Winchester, VA 22602

Home Trends in Winchester, VA

Housing Trends

Median Sale Price
$415,000
Median Single Family Sale Price
$449,990
Median Townhouse Sale Price
$399,990
Median 2 Bedroom Sale Price
$265,000
Average Price Per Sq Ft
$209
Number of Homes for Sale
268
Last 12 months Home Sales
1,183
Months of Supply
2.70
Median List Price
$430,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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