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Middletown, VA Homes for Sale

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  • /45

    $585,000

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

    2239 Sixth St, Middletown, VA 22645

    THE FINANCING MAY BE AS IMPRESSIVE AS THE HOME! Offered at $585,000 with the potential opportunity for a qualified purchaser to assume the seller's existing VA loan. A VA assumption could offer a tremendous financing advantage compared with obtaining an entirely new mortgage, depending upon the existing loan terms and the buyer's financing structure. Veteran status is not necessarily required to

    Agent Photo

    Lori Bales

    Keller Williams Realty

    2239 Sixth St, Middletown, VA 22645
  • /52

    $649,000

    • Studio
    • 4,200 Sq Ft

    7760 Main St, Middletown, VA 22645

    THE FINANCING MAY BE AS IMPRESSIVE AS THE HOME! Offered at $649,000 with the potential opportunity for a qualified purchaser to assume the seller's existing VA loan. A VA assumption could offer a tremendous financing advantage compared with obtaining an entirely new mortgage, depending upon the existing loan terms and the buyer's financing structure. Veteran status is not necessarily required to

    Agent Photo

    Lori Bales

    Keller Williams Realty

    7760 Main St, Middletown, VA 22645
  • /14

    $645,000

    $46K PRICE INCREASE
    • Land
    • 1.38 Acres
    • $467,391 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

    Agent Photo

    Kevin Smith

    Sager Real Estate

    0 Reliance Rd Unit VAFV2013246, Middletown, VA 22645
  • /16

    $474,900

    Coming Soon Sep 22
    • 4 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    122 Birmingham Dr, Middletown, VA 22645

    "Beautiful On Birmingham" This 4-bedroom, 2 1/2 bath colonial style home is ready for you to move right in! As you enter, you'll be welcomed by the open floor plan! With a large island and plenty of cabinet space the kitchen was built for everyday life and entertainment. Spacious family room, eating area and first floor flex room perfect for a home office! Upstairs you'll find a large primary

    Matt Kilmer Samson Properties

    122 Birmingham Dr, Middletown, VA 22645
  • /56

    $374,900

    $15K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,587 Sq Ft

    1810 Chapel Rd, Middletown, VA 22645

    This charming ranch-style home, beautifully renovated in 2018, offers a perfect blend of comfort and modern living. Nestled on a serene half-acre lot, the property features a welcoming interior with four spacious bedrooms and a thoughtfully designed layout. Enjoy the warmth of hardwood floors throughout, complemented by upgraded countertops in the eat-in kitchen, which seamlessly connects to the

    Lilly Triplett Colony Realty

    1810 Chapel Rd, Middletown, VA 22645
  • /54

    $3,100,000

    • 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
  • /62

    $699,999

    $30K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,642 Sq Ft

    289 Reliance Woods Dr, Middletown, VA 22645

    Welcome to 289 Reliance Woods Dr – a thoughtfully designed, all-brick rancher on 3 peaceful acres in the heart of Reliance Woods.Built with long-term comfort in mind, this one-level home offers a spacious, accessible layout ideal for everyday living and aging in place. Wide doorways, minimal steps, and generous room sizes make the home functional without sacrificing warmth or

    Christine Binnix Samson Properties

    289 Reliance Woods Dr, 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
  • /50

    $369,000

    $10K PRICE DROP
    • 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
  • /20

    $379,999

    • 3 Beds
    • 3 Baths
    • 1,566 Sq Ft

    6666 Valley Pike, Middletown, VA 22645

    NEW ROOF INSTALLED AUGUST 2026! Set along Historic Route 11 between Middletown and Stephens City, this single-level 4-bedroom, 3-bathroom home sits on a 0.43-acre lot and has received steady updates over the past four years. Inside, two bedrooms plus the living and dining rooms feature updated flooring, and one bathroom has been fully remodeled. New carpet was recently added in the mudroom and

    Jonathan Minerick Homecoin.com

    6666 Valley Pike, Middletown, VA 22645
  • /27

    $464,999

    $1K PRICE DROP
    • 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
  • /40

    $409,900

    • 3 Beds
    • 2 Baths
    • 1,333 Sq Ft

    131 Emmet St, Middletown, VA 22645

    Adorable 5-year-young rancher backing to common area in quaint Middletown! This beautifully maintained home feels practically brand new with luxury vinyl plank flooring throughout the main living areas, brand-new carpet in the bedrooms, and fresh paint throughout. Enjoy easy one-level living with a desirable split-bedroom floor plan. The spacious kitchen opens to the dining and living areas and

    Lisa Cox Colony Realty

    131 Emmet St, Middletown, VA 22645
  • /52

    $535,000

    $15K PRICE DROP
    • 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
  • /101

    $815,000

    $10K PRICE DROP
    • 6 Beds
    • 3.5 Baths
    • 4,768 Sq Ft

    816 Great Lake Dr, Middletown, VA 22645

    Discover a rare opportunity to own an exceptional custom residence where timeless craftsmanship, refined comfort, and peaceful natural surroundings come together. Nestled on five picturesque wooded acres within an exclusive lake community in Middletown, this remarkable estate offers over 4,700 square feet of beautifully designed living space, creating the perfect balance of luxury, privacy, and

    Meghan Pachas Realty ONE Group Old Towne

    816 Great Lake Dr, Middletown, VA 22645
  • /43

    $324,000

    $25K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,152 Sq Ft

    2111 Shawn Dr, Middletown, VA 22645

    ROOMY RANCHER ON MORE THAN HALF AN ACRE! IN MIDDLETOWN, COMMUTER CONVENIENT TO I-81, I-66, Winchester, Stephens City, Strasburg and Front Royal. Near historic Belle Grove Plantation and Cedar Creek Battlefield, Laurel Ridge Community College, the Blue Ridge Mountains and the Shenandoah River. Don't let this one get away! So much bigger than it looks! This 3-bedroom rancher at the end of a

    Teresa Strohmeyer ERA Oakcrest Realty, Inc.

    2111 Shawn Dr, Middletown, VA 22645
  • /147

    $709,900

    $20K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,784 Sq Ft

    461 Veterans Rd, Middletown, VA 22645

    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 upgrades, including added insulation, a new pressure tank, and a new roof installed in

    Lilly Triplett Colony Realty

    461 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
  • /65

    $525,000

    $15K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,472 Sq Ft

    102 Curtain Fall Dr, Middletown, VA 22645

    AVAILABLE FOR SALE AND RENT!! Rental listing is VAFV2044396.MOVE IN READY!!! Experience the best of Shenandoah Valley living in this beautifully located home, where breathtaking sunset mountain views create the perfect backdrop to everyday life. Nestled in a quiet, dog-friendly community, you'll enjoy peaceful surroundings without sacrificing convenience.Ideally situated just minutes from

    Rebecca Sims Century 21 Redwood Realty

    102 Curtain Fall Dr, Middletown, VA 22645
  • /25

    $1,350,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,086 Sq Ft

    0 Gruver Grade Unit VAWR2014918, Middletown, VA 22645

    Upscale Modern Farmhouse To Be Built on 8.75 AcresExperience the perfect balance of refined craftsmanship and modern farmhouse elegance. This exceptional to-be-built custom residence is beautifully positioned on 8.75 primarily cleared picturesque acres with a small band of trees at the center, offering a sophisticated retreat with plenty of room to breathe. Designed for premium country

    Sarah Roop Key Move Properties, LLC.

    0 Gruver Grade Unit VAWR2014918, Middletown, VA 22645
  • /14

    $995,000

    • Land
    • 63.49 Acres
    • $15,672 per Acre

    105 Ridgemont Rd, Middletown, VA 22645

    Rare opportunity to own 63.48± acres in northern Warren County featuring a scenic mix of open fields, mature woodlands, and West Run Creek winding through the property. Whether you're seeking a private estate, recreational retreat, hunting property, or long-term land investment, this property offers exceptional privacy and natural beauty with potential for future low-density residential

    Brett Haynes Oakcrest Commercial LLC.

    105 Ridgemont Rd, Middletown, VA 22645
  • /51

    $449,900

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft

    114 Curtain Fall Dr, Middletown, VA 22645

    Welcome to 114 Curtain Fall Drive, an exceptional, practically brand-new ranch home where modern design meets total convenience! Perfectly situated in a vibrant Middletown community with quick access to major commuter routes, local dining, shopping, parks, and schools, this move-in-ready gem delivers effortless one-level living at its absolute finest. From the moment you step inside, sleek LVP

    Dan Whitacre Colony Realty

    114 Curtain Fall 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.

Middletown, VA Home Prices

Middletown, VA
Median Home Price
$477,449
Median Sale Price
$462,499
-4% YoY
Avg. Price per Square Foot
$200
Median Single Family Price
$479,999
Median Townhouse Price
$325,000
Total Active Listings
21 listings
Market Conditions
3 Months of Supply
Seller's Market

Frequently Asked Questions

What is the average home price in Middletown, VA?
Homes for sale in Middletown, VA have an average home price of $577,019.
How many homes have sold over the last 12 months in Middletown, VA?
66 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 $477,449. If you put a 20% down payment of $95,500 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $2,530 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $108K 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.
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