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Middletown Homes for Sale

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  • /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
  • /36

    $585,000

    Open Sat 1PM - 3PM
    • 4 Beds
    • 2.5 Baths
    • 2,944 Sq Ft

    2239 Sixth St, Middletown, VA 22645

    Welcome to this stunning Circa 1872 farmhouse nestled in the heart of Middletown with a stunning view! Situated on a gorgeous 1-acre lot on a quiet one-way street just off Main Street, this spacious property offers the perfect blend of peaceful living and everyday convenience, with easy access to I-81. Zoned B1, it offers many possibilities for either residential or commercial use, including a

    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

    Exceptional investment opportunity in the heart of Middletown, directly across from the famous Wayside Theater, and conveniently located just minutes from I-81. This unique property features two attached living units, offering outstanding income potential, multigenerational living, or the flexibility to occupy one unit while generating rental income from the other.The main residence

    Agent Photo

    Lori Bales

    Keller Williams Realty

    7760 Main St, Middletown, VA 22645
  • /6

    $110,000

    • Land
    • 2 Acres
    • $55,000 per Acre

    LOT 31 Comforter Ln, North River, VA 22645

    If you are in search of the perfect building lot that provides seclusion, yet has easy access to state maintained roads nearby. You've found it! Tremendous views of the Signal Knob Mountain from various lots! Perfect Dream Home Lot for the commuter looking to escape from the hustle of the city! Whether you want a House-on-the-Hillside Lot surrounded by seclusion, or a lot located close to the

    Robin Gochenour Skyline Team Real Estate

    LOT 31 Comforter Ln, North River, 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

    $730,000

    • 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
  • /2

    $700,000

    Coming Soon
    • 3 Beds
    • 3.5 Baths
    • 2,242 Sq Ft

    440 Chimney Cir, Middletown, VA 22645

    FIRST TIME ON THE MARKET!Discover the exceptional charm of this custom-built, one-owner home, gracefully positioned on a picturesque 2.33-acre knoll in desirable Chimney Hills Estates. Beautifully maintained and thoughtfully designed, this 2017 custom home built by Donald Adams, offers a wonderful blend of elegance, comfort, and easy living. The home is heated and cooled with a heatpump and

    Darcy Amburn Colony Realty

    440 Chimney Cir, 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

    $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
  • /33

    $385,000

    • Land
    • 20 Acres
    • $19,250 per Acre

    0 River Ridge Dr Unit VAWR2011208, North River, VA 22645

    RARE opportunity to own 20 private acres with approximately 400 feet of Shenandoah River frontage in the heart of the Shenandoah Valley. Recently reduced and now aggressively priced, this extraordinary property offers the perfect setting to build a luxury riverfront estate, private retreat, vacation getaway, or investment property.Tucked away in the scenic River Ridge community, this wooded

    Vicky Mashaw Samson Properties

    0 River Ridge Dr Unit VAWR2011208, North River, 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
  • /101

    $825,000

    • 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

    $349,000

    • 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

    $729,900

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

    461 Veterans Rd, Middletown, VA 22645

    Back on the market at no fault of the seller - contract was contingent on a home sale contingency.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

    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
  • /81

    $859,900

    $40K 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 100K 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

    Jennifer Cook CENTURY 21 New Millennium

    4 Jackson Place, Middletown, VA 22645
  • /65

    $540,000

    Open Sun 1PM - 3PM
    • 4 Beds
    • 3 Baths
    • 2,472 Sq Ft

    102 Curtain Fall Dr, Middletown, VA 22645

    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 I-81 and Route 66, this home offers an easy commute while

    Rebecca Sims Century 21 Redwood Realty

    102 Curtain Fall Dr, Middletown, VA 22645
  • /17

    $1,350,000

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

    0 Gruver Grade Unit VAWR2014918, Middletown, VA 22645

    Luxury Farmhouse **To Be Built **on 8.75 Private Acres Experience the perfect blend of refined craftsmanship and modern farmhouse elegance in this exceptional to-be-built custom residence, gracefully positioned on 8.75 picturesque acres. Designed with sophisticated living in mind, this stunning home offers 4 bedrooms, 3 full baths, and 1 half bath. where timeless architecture meets thoughtfully

    Sarah Roop Key Move Properties, LLC.

    0 Gruver Grade Unit VAWR2014918, Middletown, VA 22645
  • /13

    $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

Middletown Home Prices vs. Nearby VA, VA Neighborhoods

Middletown Stephens City Strasburg
Median Home Price
$479,999
$440,000
$357,500
Median Sale Price
$460,000
-4% YoY
$425,000
-3% YoY
$335,000
+1% YoY
Median Single Family Price
$479,999
$448,500
$354,000
Median Townhouse Price
$325,000
$371,839
$357,615
Median Condo Price
--
$215,000
$208,500
Total Active Listings
14 listings
120 listings
60 listings
Market Conditions
3 Months of Supply
Seller's Market
3 Months of Supply
Seller's Market
4 Months of Supply
Balanced Market

Frequently Asked Questions Why Live in Middletown

Is Middletown a good place to live?
Middletown is a good place to live. Middletown is considered very car-dependent and somewhat bikeable. Middletown is a neighborhood with a crime score of 2, making it safer than the average neighborhood in the U.S. Middletown has 2 parks for recreational activities. It has a median age of 43. The average household income is $103,749 which is below the national average. College graduates make up 25.1% of residents. A majority of residents in Middletown are home owners, with 23% of residents renting and 77% of residents owning their home. A local real estate agent serving Middletown can help you decide if this neighborhood is the right one for you. Learn more on our Middletown neighborhood guide.
Is Middletown, VA a safe neighborhood?
Middletown, VA is safer than the average neighborhood in the United States. It received a crime score of 2 out of 10.
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 6.65%, your estimated principal and interest payment would be $2,470 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $106K 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 $104K.
What are the best public schools in Middletown?
The best public schools that serve Middletown are:
What are the most popular zip codes in Middletown, Middletown, VA?
The most popular zip codes in Middletown, Middletown, VA include 22645, 22655, 22657, 22630 and 22641.
What are the most popular neighborhoods near Middletown, Middletown, VA?
The most popular neighborhoods near Middletown, Middletown, VA are Fort Valley, Star Tannery, Bentonville and Stephenson.
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