23

Middletown, VA Homes for Sale

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  • /5

    $585,000

    Coming Soon
    • 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
  • /3

    $649,000

    Coming Soon
    • 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 showcases

    Agent Photo

    Lori Bales

    Keller Williams Realty

    7760 Main St, Middletown, VA 22645
  • /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
  • /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

    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
  • /69

    $420,000

    • 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
  • /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
  • /13

    $110,000

    • Land
    • 1.96 Acres
    • $56,122 per Acre

    209 Mineral St, Middletown, VA 22645

    Rare opportunity to own a 1.96-acre wooded lot in the historic Town of Middletown! This unique property offers approximately 1.5 acres of buildable land located outside the floodplain, with an additional 0.5-acre parcel across the railroad tracks within the floodplain and bordered by Meadow Creek. An expired PERC approval for a 2-bedroom home is on file. Sellers have also obtained a CSX easement

    Melissa Crider Sager Real Estate

    209 Mineral St, 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 charm. The main

    Christine Binnix Samson Properties

    289 Reliance Woods Dr, Middletown, VA 22645
  • /55

    $634,900

    $15K PRICE DROP
    • 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; land is on both sides of the driveway. All brick and offering more than 2,700 sq. ft. on the main level, this home is ready for you.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

    Lilly Triplett Colony Realty

    298 Mcdaniel 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
  • /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

    • 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
  • /36

    $825,000

    • 4 Beds
    • 3 Baths
    • 2,840 Sq Ft

    354 Guard Hill Rd, Middletown, VA 22645

    Custom builder's home on 20 flat, private acres in Middletown offering the perfect blend of quality craftsmanship, comfort, and functionality. Thoughtfully designed with an open floor plan filled with abundant natural light, this home features an oversized kitchen island, stainless steel appliances, and a convenient hot water pot filler. A main-level bedroom with an adjoining full bath, currently

    Sarah Reynolds Keller Williams Realty

    354 Guard Hill Rd, Middletown, VA 22645
  • /2

    $825,000

    Coming Soon
    • 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
  • /82

    $725,000

    • 5 Beds
    • 3.5 Baths
    • 3,588 Sq Ft

    258 Chimney Cir, Middletown, VA 22645

    Welcome to your dream home in highly sought-after Middletown! Nestled on 2.6 private acres, this stunning colonial offers the perfect blend of space, comfort, and modern upgrades, with 5 bedrooms, 3.5 bathrooms, and over 3,500 finished square feet. From the moment you arrive, the charming full front porch invites you to relax and take in the peaceful surroundings. Step inside to a welcoming foyer

    Kristi Cooper Realty ONE Group Old Towne

    258 Chimney 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
  • /81

    $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
  • /2

    $540,000

    Coming Soon
    • 4 Beds
    • 3 Baths
    • 2,472 Sq Ft

    102 Curtain Fall Dr, Middletown, VA 22645

    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 keeping you close to

    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
  • /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.

Frequently Asked Questions

What is the average home price in Middletown, VA?
Homes for sale in Middletown, VA have an average home price of $578,603.
How many homes have sold over the last 12 months in Middletown, VA?
72 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 $489,999. If you put a 20% down payment of $98,000 and had a 30-year fixed mortgage with an interest rate of 6.66%, your estimated principal and interest payment would be $2,520 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.

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
$341,500
Median 1 Bedroom Sale Price
$150,000
Average Price Per Sq Ft
$215
Number of Homes for Sale
17
Last 12 months Home Sales
72
Months of Supply
2.80
Median List Price
$489,999
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%
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