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Middletown, VA Homes for Sale

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  • /41

    $399,900

    • 3 Beds
    • 2 Baths
    • 1,378 Sq Ft

    151 Cougill Rd, Middletown, VA 22645

    One-level living in the sought-after Village at Middletown! This move-in-ready home welcomes new owners with an open floor plan designed for comfortable living and easy entertaining. The living room flows seamlessly into the kitchen, creating a bright and inviting main living space. The spacious kitchen features a breakfast bar, ample table space, and access to a large, low-maintenance Trex

    Agent Photo

    Ken Evans

    RE/MAX Real Estate Connections

    (540) 515-4291

    151 Cougill Rd, Middletown, VA 22645
  • /95

    $635,000

    • 6 Beds
    • 3.5 Baths
    • 3,888 Sq Ft

    76 Katie Ln, Middletown, VA 22645

    Freshly Painted Interior & Refinished Hardwood Floors-Upper-Level Hallway & Stairs! Beautiful Stone Front Colonial in Sought-After Pineland Park 3,887 total finished square feet offering 6 bedrooms and 3.5 baths on a 1-acre lot. Located in the desirable Pineland Park neighborhood of Warren County, ideal for commuting via I-66 and I-81. Minutes to golf, wineries, hiking, shopping, and downtown

    Agent Photo

    Ken Evans

    RE/MAX Real Estate Connections

    (540) 701-4995

    76 Katie Ln, 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
  • /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
  • /62

    $599,900

    • 5 Beds
    • 4 Baths
    • 4,006 Sq Ft

    2140 Sixth St, Middletown, VA 22645

    This ranch home located in a quiet Middletown neighborhood is a gem hidden in plain sight and full of surprises. First, it has 4,000 resplendent finished square feet, and second, it offers two levels of independent living. The floorplan flows seamlessly, providing the kind of breathing room you’ll appreciate, enhanced with an elegant color palette, natural light, and stunning hardwood floors that

    Dan Whitacre Colony Realty

    2140 Sixth St, Middletown, VA 22645
  • /2

    $549,900 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 2,768 Sq Ft

    646 Guard Hill Rd, Middletown, VA 22645

    Classic charm meets modern living in this beautifully maintained Colonial set on 3 peaceful acres. Step inside to find gleaming hardwood floors, a spacious living room perfect for gathering with a propane fireplace complete with a fan, a large kitchen with plenty of room to cook and entertain, and a separate dining room ideal for hosting. With 4 generously sized bedrooms, there’s plenty of room

    Donna Anderson Samson Properties

    646 Guard Hill Rd, Middletown, VA 22645
  • /36

    $699,900 Coming Soon

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

    201 Liberty Ln, Middletown, VA 22645

    Coming Soon in Middletown on 5.21 acres — custom home with finished lower-level apartment ideal for multi-generational living. This one-level home with a fully finished lower level offers space, flexibility, and a peaceful setting along a private lane in the Shenandoah Valley. The main level features high ceilings, quality finishes, and a spacious layout including a living room, dining room,

    Abby Walters Preslee Real Estate

    201 Liberty Ln, Middletown, VA 22645
  • /54

    $695,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    220 Lakeland Cir, Middletown, VA 22645

    Welcome to the perfect blend of modern style and peaceful country living. This brand-new modern farmhouse with craftsman influence is privately nestled on 6.6 wooded acres, offering the seclusion you crave while remaining just minutes from Routes 66 and 81 for an easy commute. Thoughtfully designed with meticulous attention to detail, this 3-bedroom home offers 2,000 square feet of beautifully

    Sharon Farinholt Realty ONE Group Old Towne

    220 Lakeland Cir, 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
  • /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
  • /54

    $2,999,900

    • 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
  • /48

    $449,900

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    471 Coville St, Middletown, VA 22645

    Built in 2020, this well-maintained 4-bedroom, 2.5-bath home in Middletown, VA offers modern comfort with thoughtful design and room to grow. The main level with open plan flows from entry, to living room, to kitchen, to dining area, and also features a dedicated office with beautiful custom built-ins—perfect for working from home or creating an organized study space. The spacious primary suite

    Justin Mistretta Berkshire Hathaway HomeServices PenFed Realty

    471 Coville St, Middletown, VA 22645
  • /61

    $424,900

    • 3 Beds
    • 2 Baths
    • 2,630 Sq Ft

    6731 Middle Rd, Middletown, VA 22645

    Fully Renovated Rancher!! Beautiful Country Setting! Come check out this Incredibly SPACIOUS Home on just over an Acre. Over 2600+ finished sq feet, 3 bedrooms & 2 full baths. Extra bonus rooms could be bedrooms as well or however you choose. ALL BRAND NEW Flooring, Painting, Lighting, 3 Mini Splits, Architectural Roof, Septic System, Well pressure tank, Windows, and Kitchen! HVAC in Great Shape!

    Jodi Costello ERA Oakcrest Realty, Inc.

    6731 Middle Rd, 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
  • /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
  • /48

    $484,900

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

    135 Birmingham Dr, Middletown, VA 22645

    Backing to trees with a fully fenced backyard, Trex deck, hot tub, built-in fire pit, and storage shed, this beautiful craftsman-style home offers the outdoor setting buyers are looking for along with a warm, functional interior designed for everyday living. Inside, you will find 4 spacious upper-level bedrooms, a main-level office, and a bright layout that blends comfort and flexibility. The

    Robin Gebhardt EXP Realty, LLC

    135 Birmingham Dr, 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
  • /147

    $2,000,000

    • 4 Beds
    • 3.5 Baths
    • 4,888 Sq Ft

    690 Comforter Ln, Middletown, VA 22645

    Panoramic mountain views stretching for miles define this custom-built estate, priced UNDER recent appraised value. Designed to capture views from nearly every window, the home pairs refined craftsmanship with the natural beauty of the Shenandoah Valley, framed by the Blue Ridge Mountains, Signal Knob, and the Appalachian Mountains. The property consists of two separately recorded 10-acre

    Kristina Towns Weichert Realtors - Blue Ribbon

    690 Comforter Ln, 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 $533,261.
How many homes have sold over the last 12 months in Middletown, VA?
101 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 6.38%, your estimated principal and interest payment would be $2,400 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $103K 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

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
$212
Number of Homes for Sale
13
Last 12 months Home Sales
101
Months of Supply
1.50
Median List Price
$479,999
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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