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Middletown, VA Homes for Sale

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  • 107 Seventh St Unit 36396779, Middletown, VA 22645
    107 Seventh St Unit 36396779, Middletown, VA 22645
    107 Seventh St Unit 36396779, Middletown, VA 22645
    /42

    $428,990 New Construction

    • 3 - 4 Beds
    • 2.5 Baths
    • 1,840 Sq Ft

    Coral Plan at Middletown Place - Seasons, Middletown, VA 22645

    The main floor of the Coral plan offers a large, uninterrupted space for relaxing and entertaining. The kitchen features a spacious center island and opens to the dining and great rooms. Upstairs, you'll find a convenient laundry, a full bath tucked between two generous bedrooms, and an inviting primary suite with a walk-in closet and private bath. This plan will be built with either a loft or an

    Richmond American Homes Builder
    107 Seventh St Unit 36396779, Middletown, VA 22645
  • 2239 Sixth St, Middletown, VA 22645
    2239 Sixth St, Middletown, VA 22645
    2239 Sixth St, Middletown, VA 22645
    /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
  • 0 Reliance Rd Unit VAFV2013246, Middletown, VA 22645
    0 Reliance Rd Unit VAFV2013246, Middletown, VA 22645
    0 Reliance Rd Unit VAFV2013246, Middletown, VA 22645
    /14

    $595,000

    • 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
  • 0 Reliance Rd Unit VAFV2039508, Middletown, VA 22645
    0 Reliance Rd Unit VAFV2039508, Middletown, VA 22645
    0 Reliance Rd Unit VAFV2039508, Middletown, VA 22645
    /13

    $725,000

    • 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
  • 1115 Chapel Rd, Middletown, VA 22645
    1115 Chapel Rd, Middletown, VA 22645
    1115 Chapel Rd, 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
  • 155 Turkey Ln, Middletown, VA 22645
    155 Turkey Ln, Middletown, VA 22645
    155 Turkey Ln, Middletown, VA 22645
    /77

    $765,000

    • 3 Beds
    • 2 Baths
    • 1,748 Sq Ft

    155 Turkey Ln, Middletown, VA 22645

    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 retreat with breathtaking sunsets and mountain views that inspire relaxation and rejuvenation from your

    Thomas Campbell Fathom Realty

    155 Turkey Ln, Middletown, VA 22645
  • 0 Rd Unit VAFV2039608, Middletown, VA 22645
    0 Rd Unit VAFV2039608, Middletown, VA 22645
    0 Rd Unit VAFV2039608, 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
  • 0 Huttle Rd Unit VAFV2038332, Middletown, VA 22645
    0 Huttle Rd Unit VAFV2038332, Middletown, VA 22645
    0 Huttle Rd Unit VAFV2038332, 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
  • 145 Dursley Cir, Middletown, VA 22645
    145 Dursley Cir, Middletown, VA 22645
    145 Dursley Cir, Middletown, VA 22645
    /27

    $465,999

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

    145 Dursley Cir, Middletown, VA 22645

    This move-in ready Cedar home in the Villages at Middletown combines the benefits of new construction with a thoughtfully designed, open-concept layout. Featuring 4 bedrooms, 2.5 bathrooms, and 1,900 sq ft of living space, the main level is anchored by a modern kitchen with upgraded mocha cabinetry and stainless steel appliances. The interior features a comfortable mix of vinyl plank flooring and

    Atul Sharma Long & Foster Real Estate, Inc.

    145 Dursley Cir, Middletown, VA 22645
  • 201 Liberty Ln, Middletown, VA 22645
    201 Liberty Ln, Middletown, VA 22645
    201 Liberty Ln, Middletown, VA 22645
    /52

    $699,900

    • 4 Beds
    • 3.5 Baths
    • 3,540 Sq Ft

    201 Liberty Ln, Middletown, VA 22645

    Seller offering a $15,000 credit, providing buyers an opportunity to make interior updates that suit their style! For Sale in Middletown on 5.21 Gorgeous Acres! Spacious Custom home with a fully finished lower-level apartment, perfect for multi-generational living. Tucked along a private gravel lane in the Shenandoah Valley, this property offers a peaceful, semi-secluded setting with a blend of

    Abby Walters Preslee Real Estate

    201 Liberty Ln, Middletown, VA 22645
  • 2339 Third St, Middletown, VA 22645
    2339 Third St, Middletown, VA 22645
    2339 Third St, Middletown, VA 22645
    /25

    $219,900

    • 4 Beds
    • 1.5 Baths
    • 1,439 Sq Ft

    2339 Third St, Middletown, VA 22645

    4 -bedroom, 1.5-bath single-story home with 1,439 sq ft on a 0.14-acre lot. Features living room, second living space, dining area, kitchen, and two storage shops. Roof functional; siding and gutters may need updates. Appliances included: fridge, freezer, stove. Window AC units and wood stove. Public water & sewer, electricity by REC. Conveniently located near Frederick County schools.

    Derek Greene The Greene Realty Group

    2339 Third St, Middletown, VA 22645
  • 0 Tbd Veterans Rd, Middletown, VA 22645
    0 Tbd Veterans Rd, Middletown, VA 22645
    0 Tbd Veterans Rd, 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
  • 4 Jackson Place, Middletown, VA 22645
    4 Jackson Place, Middletown, VA 22645
    4 Jackson Place, Middletown, VA 22645
    /9

    $899,900 Coming Soon

    • 6 Beds
    • 5.5 Baths
    • 5,785 Sq Ft

    4 Jackson Place, Middletown, VA 22645

    **Professional photos coming soon.** 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, and 3-car garage. The gourmet kitchen features plenty of counter space, upgraded

    Jennifer Cook CENTURY 21 New Millennium

    4 Jackson Place, Middletown, VA 22645
  • 139 Kensington Cir, Middletown, VA 22645
    139 Kensington Cir, Middletown, VA 22645
    139 Kensington Cir, Middletown, VA 22645
    /38

    $341,990

    • 3 Beds
    • 2.5 Baths
    • 1,220 Sq Ft

    139 Kensington Cir, Middletown, VA 22645

    Why Rent when you can own your own home! Welcome to this beautifully maintained 3 bed, 2.5 bath townhome with some upgrades including granite counters, offering the perfect blend of comfort, convenience, and lifestyle. In excellent condition, this home features an open floor plan with spacious living areas, abundant natural light, and modern finishes throughout. Located just minutes from I81 and

    Pamela Baber Coldwell Banker Premier

    139 Kensington Cir, Middletown, VA 22645
Virginia Frederick County Middletown

Real Estate & Homes for Sale in Middletown, VA

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.

Learn more about living in Middletown

Frequently Asked Questions

What is the average home price in Middletown, VA?
Homes for sale in Middletown, VA have an average home price of $539,519.
How many homes have sold over the last 12 months in Middletown, VA?
96 homes have sold in Middletown, VA over the last 12 months.
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 6.3%, your estimated principal and interest payment would be $2,380 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $102K a year to afford the median home price in Middletown. Learn how much home you can afford with our Home Affordability Calculator.
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 Trends in Middletown, VA

On average, homes in Middletown, VA sell after 65 days on the market compared to the national average of 57 days. The median sale price for homes in Middletown, VA over the last 12 months is $479,999, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$479,999
Median Single Family Sale Price
$479,999
Median Townhouse Sale Price
$325,000
Average Price Per Sq Ft
$217
Number of Homes for Sale
9
Last 12 months Home Sales
96
Months of Supply
1.10
Median List Price
$479,999
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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