12

Middletown, VA Houses for Sale

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  • /98

    $774,900

    • 6 Beds
    • 5 Baths
    • 3,908 Sq Ft

    80 Little Sorrel Dr, Middletown, VA 22645

    Offering just over 3900 finished square feet, 6 bedrooms, 5 full bathrooms, a main level bedroom with access to a full bath, a 1-acre lot, no HOA, and a peaceful setting in a golf course community, this home is designed for both everyday living and entertaining. Mountain views, an 880 square foot Trex deck, a roof that's only 5 years old, and a flexible floor plan complete the package.The

    Agent Photo

    Catherine DeMay

    Real Broker, LLC

    80 Little Sorrel Dr, Middletown, VA 22645
  • /34

    $449,900

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

    154 Dursley Cir, Middletown, VA 22645

    Better than new and meticulously maintained, this beautiful 4-bedroom, 2.5-bath home offers the perfect combination of modern finishes, thoughtful upgrades, and an unbeatable location in the heart of Middletown. Built in 2023, this home is truly move-in ready, with improvements already completed for you. The main level features durable luxury vinyl plank flooring and a bright, open layout

    Agent Photo

    Bradley Comstock

    ERA Oakcrest Realty, Inc.

    154 Dursley Cir, 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
  • /69

    $420,000

    Open Sun 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft

    2105 Shawn Dr, Middletown, VA 22645

    Welcome to this beautifully maintained brick Cape Cod, tucked away on a private 0.70-acre cul-de-sac lot in Middletown! Thoughtfully updated and meticulously cared for, this home offers the perfect blend of charm, comfort, and outdoor living. Step inside to find fresh interior paint, hardwood floors, updated bathrooms, and a spacious living room featuring a new gas fireplace with thermostat and

    Peter Van Cleave Real Broker, LLC

    2105 Shawn Dr, Middletown, VA 22645
  • /55

    $649,900

    • 3 Beds
    • 2.5 Baths
    • 2,730 Sq Ft

    298 Mcdaniel Ln, Middletown, VA 22645

    Privacy, space, and convenience come together in this all-brick ranch on just over 7 acres with no HOA. Built in 1989 and offering more than 2,700 sq. ft. on the main level, this home is ready for your personal updates and style.The property features 3 spacious bedrooms, 2.5 baths, a living room with a brick fireplace and wood stove insert, a family room, and a large mudroom off the kitchen.

    Lilly Triplett Colony Realty

    298 Mcdaniel Ln, Middletown, VA 22645
  • /50

    $379,000

    • 4 Beds
    • 2 Baths
    • 2,512 Sq Ft

    7927 Main St, Middletown, VA 22645

    An exceptional opportunity to restore and reimagine a historic Main Street property in the heart of Middletown. Prominently located along one of the towns most recognized corridors, this four bedroom, two bath home offers timeless character, outstanding potential, and a location that is difficult to duplicate. Believed to date to the early 1800s, the home has been part of Middletown history for

    Sharon Daniels Coldwell Banker Premier

    7927 Main St, Middletown, VA 22645
  • /70

    $949,999

    • 5 Beds
    • 5.5 Baths
    • 5,672 Sq Ft

    228 Mercys Dr, Middletown, VA 22645

    PRICED BELOW APPRAISED VALUE!! Nestled on an expansive 6.84-acre lot just minutes from shopping, dining, and commuter routes, this stunning colonial exudes elegance and comfort. Built in 2013, the home features a harmonious blend of vinyl siding and stone, creating a timeless façade that invites you in. Step inside to discover five spacious bedrooms and six bathrooms. The heart of the home boasts

    Alicia Harris Keller Williams Realty

    228 Mercys Dr, Middletown, VA 22645
  • /27

    $465,999

    Open Sun 12PM - 2PM
    • 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
  • /147

    $729,900

    • 3 Beds
    • 3.5 Baths
    • 2,784 Sq Ft

    461 Veterans Rd, Middletown, VA 22645

    Coming Soon! Interior Photos will be uploaded July 9th. First time offered on the market, this stunning Cape Cod home is perfectly situated on 2.79 acres within the Belle Grove and Cedar Creek National Historical Park, offering a rare opportunity to enjoy the beauty and privacy of protected parkland with no future development surrounding the property. The current owners have completed numerous

    Lilly Triplett Colony Realty

    461 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 assessment! Bring your design ideas because with an acceptable offer, sellers are including a credit at closing to add your personal touch or use to assist with closing costs. This expansive 6-bedroom, 6 bath home has a lot to offer, from the grand entryway to the soaring ceilings, dual staircases, beautiful crown

    Jennifer Cook CENTURY 21 New Millennium

    4 Jackson Place, Middletown, VA 22645
  • /33

    $399,900

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,332 Sq Ft

    171 Birmingham Dr, Middletown, VA 22645

    This home was built in 2023 and well cared for from day one. Several upgrades were made for this home, such as Architectural Shingles, Granite Countertops, Stainless Steel Appliances, Fully finished garage floor, garage drywalled and painted, Recessed lighting throughout the home, Storm doors on the front a rear. Washer & Dryer convey with the sale. Basement could be finish to add a bathroom and

    Michael Sprague Samson Properties

    171 Birmingham Dr, 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.

Single Family Home Price Trends

Median Home Price
$489,999
Median 3-Bedroom Home Price
$459,999
Median 4-Bedroom Home Price
$499,999
Median 5-Bedroom Home Price
$900,000
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