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Middletown, VA Homes for Sale

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  • /60

    $649,900

    • 4 Beds
    • 2.5 Baths
    • 2,944 Sq Ft

    2239 Sixth St, Middletown, VA 22645

    Have you been looking for the perfect sophisticated and elegant historic home? Do you want everything; a gracious home, amazing space, acreage, a place for chickens, but also walkable and close to town? It sounds impossible, but you've found it! Welcome to historic Maplewood, circa 1872, know colloquially as The Tower. With no HOA and business B-1 zoning, this property presents endless

    Amanda White Nova Home Hunters Realty

    2239 Sixth St, Middletown, VA 22645
  • /14

    $595,000

    $4K PRICE DROP
    • Land
    • 1.38 Acres
    • $431,159 per Acre

    0 Reliance Rd Unit VAFV2013246, Middletown, VA 22645

    Prime commercial site. This 1.54-acre property boasts a coveted B-2 zoning, making it an ideal location for business ventures. Conveniently positioned just off Interstate 81 and a short drive from Interstate 66, this site offers excellent visibility, ensuring maximum exposure for any enterprise. Situated between two well-known establishments, McDonald's and Econo Lodge, it benefits from high

    Kevin Smith Sager Real Estate

    0 Reliance Rd Unit VAFV2013246, Middletown, VA 22645
  • /13

    $725,000

    $74K PRICE DROP
    • Land
    • 3.84 Acres
    • $188,802 per Acre

    0 Reliance Rd Unit VAFV2039508, Middletown, VA 22645

    Options galore! Purchase or ground lease with potential seller financing for a qualified purchaser. I-81 Exit #302 is the Gateway entrance into the Historic Town of Middletown, Virginia. This is the last remaining lot at the corner of Reliance Road and Valley Ave (Rt #11). We have 3.84 acres zoned B2 highway commercial. You are surrounded by The Village at Middletown by Ryan Homes. Richmond

    Jim Guisewhite Commercial Specialists

    0 Reliance Rd Unit VAFV2039508, Middletown, VA 22645
  • /54

    $2,999,000

    • 3 Beds
    • 2.5 Baths
    • 2,969 Sq Ft

    1115 Chapel Rd, Middletown, VA 22645

    Introducing FOXLEA FARM, A Stately Plantation Style Estate, where Southern Charm Meets Mountain Majesty – 58+/- Acres of Endless Potential! Welcome to your dream property—58+/- acres of scenic, cross-fenced pastureland nestled among breathtaking mountain views. This Southern gem is tailor-made for equestrian lovers, hobby farmers, or anyone seeking wide-open spaces with the comforts of modern

    Lisa Blansett Mountains Edge Realty LLC

    1115 Chapel Rd, Middletown, VA 22645
  • /58

    $359,900

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    6717 Middle Rd, Middletown, VA 22645

    Nestled in a serene setting, this charming ranch-style home offers a perfect blend of comfort and functionality. Built in 1965, this well-maintained residence spans 1,560 square feet and features three inviting bedrooms and two full bathrooms, making it an ideal retreat for those seeking a cozy yet spacious living environment. Step inside to discover a warm and welcoming atmosphere, accentuated

    Kimberly Holzer Ross Real Estate

    6717 Middle Rd, Middletown, VA 22645
  • /77

    $725,000

    Open House 6/28 $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,748 Sq Ft

    155 Turkey Ln, Middletown, VA 22645

    HUGE PRICE REDUCTION OF $39,000. APPRAISED VALUE IS $764,000. MOTIVATED SELLERS MOVING DUE TO NEW JOB. Nestled within the serene enclave of River Ridge on the Shenandoah, this exquisite ranch-style home built in 2022, offers a harmonious blend of modern luxury and natural beauty. Spanning an impressive 20 acres, the property is enveloped by a lush, wooded landscape. This home provides a tranquil

    Thomas Campbell Fathom Realty

    155 Turkey Ln, Middletown, VA 22645
  • /15

    $549,000

    • Land
    • 8 Acres
    • $68,625 per Acre

    0 Rd Unit VAFV2039608, Middletown, VA 22645

    Rare opportunity in the heart of Middletown! Discover the perfect blend of small-town charm, open space, and future potential on this beautiful 8-acre property surrounded by scenic pastureland and mountain views. Currently used for cattle and hay production, the land is partially fenced and includes a shed, making it ready for agricultural use or the ideal setting for your own private

    Tana Hoffman Sager Real Estate

    0 Rd Unit VAFV2039608, Middletown, VA 22645
  • /47

    $800,000

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft

    906 Cauthorn Mill Rd, Middletown, VA 22645

    Tucked into the woods along the banks of Dry Run, this 21.78-acre property delivers the kind of privacy, usable land, and outdoor lifestyle that delivers complete comfort. The driveway follows the rocky streambed and natural beauty of Dry Run before proceeding through mature hardwoods that surround this secluded all-brick ranch, rich with wildlife, trails, and recreational opportunity. The land

    Karen Smith Pearson Smith Realty, LLC

    906 Cauthorn Mill Rd, Middletown, VA 22645
  • /74

    $725,000

    • 5 Beds
    • 2.5 Baths
    • 3,306 Sq Ft

    132 Chase Ct, Middletown, VA 22645

    Elegant Colonial on 3.47 Acres. Situated on a cul-de-sac in the lovely Chimney Hill Estates in Middletown. 4 bedrooms on 2nd level with 2 full bathrooms. Main floor offers a bedroom or office and half bath. Spacious family room off of the kitchen has a gorgeous stone hearth from floor to ceiling with a pellet stove. Paved neighborhood and driveway. Black board fencing in rear of property. Mature

    Cara Wilkins MarketPlace REALTY

    132 Chase Ct, Middletown, VA 22645
  • /48

    $419,999

    New Construction $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,630 Sq Ft

    104 Midsummer Ln, Middletown, VA 22645

    FINAL HOUSE FOR SALE! This new construction ranch home by Richmond American is move in ready! Three bedrooms and 2 full baths. The primary suite has a large walk-in closet and a private bath. Laundry is situation near the master suite offering ultimate convenience. Large kitchen island, fireplace, deck off the great room and an unfinished basement with a 3-piece plumbing rough-in for future

    Jay Day LPT Realty, LLC

    104 Midsummer Ln, Middletown, VA 22645
  • /4

    $74,000

    • Land
    • 2.83 Acres
    • $26,148 per Acre

    0 Huttle Rd Unit VAFV2038332, Middletown, VA 22645

    3 bedroom perk

    Janet Broyles CENTURY 21 New Millennium

    0 Huttle Rd Unit VAFV2038332, Middletown, VA 22645
  • /27

    $465,999

    • 4 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    145 Dursley Cir, Middletown, VA 22645

    Welcome to this move-in ready Cedar model in the Villages at Middletown—where modern design meets everyday convenience. Offering 4 bedrooms, 2.5 bathrooms, and approximately 1,900 square feet, this home delivers stylish living with an open-concept layout ideal for today’s lifestyle.The main level impresses with a sleek kitchen featuring upgraded mocha cabinetry, stainless steel appliances,

    Atul Sharma Long & Foster Real Estate, Inc.

    145 Dursley Cir, Middletown, VA 22645
  • /52

    $549,900

    • 3 Beds
    • 2 Baths
    • 2,240 Sq Ft

    3586 Reliance Rd, Middletown, VA 22645

    Tucked away in a peaceful setting, this 3-bedroom, 2-bath home offers the perfect blend of comfort, functionality, and space both inside and out. The spacious kitchen features abundant cabinet and counter space, providing plenty of storage for everyday living, along with a brand-new dishwasher. The inviting living room is centered around a cozy gas fireplace and flows directly into a beautiful

    Carolyn Young Samson Properties

    3586 Reliance Rd, Middletown, VA 22645
  • /30

    $445,000

    • 4 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    154 Dursley Cir, Middletown, VA 22645

    154 Dursley Cir, Middletown, VA 22645 is a single-family home that contains 1,680 sq ft and was built in 2023 by Ryan Homes. It contains 4 bedrooms and 2.5 bathrooms. It is housed in a very nice neighborhood. House has vinyl flooring on first floor, ceiling fan fittings in all bedrooms and living room, bathroom fitted for completion of basement. Makes a great first-time buyer home. Owner willing

    Jason Saphire HomeZu.com of Virginia

    154 Dursley Cir, Middletown, VA 22645
  • /19

    $1,900,000

    • Land
    • 7.97 Acres
    • $238,394 per Acre

    0 Tbd Veterans Rd, Middletown, VA 22645

    An exceptional opportunity in Middletown Virginia! This rare offering includes two parcels totaling nearly 20 acres: 7.97 +- zoned R1 with its adjoining 12.36+- zoned RA . Bring your creativity and fresh ideas, R1 zoning offers an immediate canvas, while the RA parcel invites future potential *subject to proper municipal approval* Conveniently located within town limits, coupled with mountain

    Jocelyn Tweedie Hunt Country Sotheby's International Realty

    0 Tbd Veterans Rd, Middletown, VA 22645
  • /80

    $874,900

    $25K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 5,785 Sq Ft

    4 Jackson Place, Middletown, VA 22645

    Welcome to this stunning house offering 6,000 square feet to enjoy and PRICED BELOW county tax assessment! This expansive 6-bedroom, 6 bath home has a lot to offer, from the grand entryway to the soaring ceilings, dual staircases, beautiful crown molding, abundant natural light, 3-car garage, in-ground pool and on an acre. The gourmet kitchen features plenty of counter space, upgraded cherry

    Jennifer Cook CENTURY 21 New Millennium

    4 Jackson Place, Middletown, VA 22645
  • /27

    $524,500

    $15K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,092 Sq Ft

    148 Dursley Cir, Middletown, VA 22645

    Find yourself at home in Middletown, in a five bedroom home with a fully finished basement!! The upper level showcases 5 bedrooms provide comfortable accommodations for family or guests. The main level you will find an open floor plan that seamlessly connects the kitchen and living room, creating a warm and welcoming atmosphere perfect for daily life and entertaining.Downstairs, the finished

    Rocio Herrador Spring Hill Real Estate, LLC.

    148 Dursley Cir, Middletown, VA 22645

Why Live in Middletown

Middletown, Virginia, located just south of Winchester, has seen significant growth since home development began in 2018, with its population nearly doubling to around 3,000. The area offers a lower cost of living compared to northern Virginia, making it attractive for commuters due to its proximity to Interstates 81 and 66. Middletown features a mix of home styles, including smaller ranch-style homes, townhouses, newer Craftsmans, Colonial Revivals, and farmhouse-style homes on larger lots. The community is known for its active involvement in local events, with the mayor often participating in festivals at Belle Grove Plantation. Sherando High School, rated highly, is a notable educational institution where community efforts recently preserved a long-standing football game tradition. Middletown Community Park hosts annual events such as Fourth of July celebrations and Christmas tree lighting ceremonies. Residents can explore the Cedar Creek and Belle Grove National Historical Park and Shenandoah National Park, which offer historical tours, hiking trails, and water activities. Dining options on Main Street include Vault and Cellar, known for its chef's cuisine and extensive bourbon selection, and Shaffer's BBQ & Market, which uses locally sourced ingredients. For shopping, residents often travel to nearby Strasburg or Fort Royal. Middletown provides a quiet atmosphere for its residents while maintaining easy access to northern Virginia and D.C.

Frequently Asked Questions

What is the average home price in Middletown, VA?
Homes for sale in Middletown, VA have an average home price of $541,100.
How many homes have sold over the last 12 months in Middletown, VA?
82 homes have sold in Middletown, VA over the last 12 months.
What is the average household income in Middletown, VA?
The average household income in Middletown, VA is $93K.
What are the most popular zip codes in Middletown, VA?
The most popular zip codes in Middletown, VA include 22645, 22655, 22657, 22630 and 22602.
How much do you need to make to afford a house in Middletown?
The median home price in Middletown is $479,999. If you put a 20% down payment of $96,000 and had a 30-year fixed mortgage with an interest rate of 6.52%, your estimated principal and interest payment would be $2,430 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $104K a year to afford the median home price in Middletown. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Middletown is $93K.
How are the schools in Middletown, VA?
Middletown, VA has highly rated public and private schools. Some of the best schools in Middletown based on Niche Grades are Sherando High School, Robert E. Aylor Middle School and Middletown Elementary School. Browse all the schools in Middletown, VA to learn more.

Home Prices in Middletown, VA

Home Price Trends

Median Sale Price
$479,999
Median Single Family Sale Price
$489,999
Median Townhouse Sale Price
$325,000
Median 2 Bedroom Sale Price
$357,500
Median 1 Bedroom Sale Price
$150,000
Average Price Per Sq Ft
$223
Number of Homes for Sale
12
Last 12 months Home Sales
82
Months of Supply
1.80
Median List Price
$479,999
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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