24

Middletown, VA Homes for Sale

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  • /11

    $479,999 New Construction

    • 3 - 4 Beds
    • 2.5 Baths
    • 1,980 Sq Ft

    Citrine Plan at Middletown Place - Seasons, Middletown, VA 22645

    Imagine your life in the two-story Citrine plan. Breakfast at the spacious kitchen island or in the nearby dining room. Host a movie night in the inviting great room. At the end of the day, retreat upstairs to the primary suite, complete with a roomy walk-in closet and private bath. The second floor also boasts two additional bedrooms, a convenient laundry and another full bath. This home will be

    Richmond American Homes Builder
    107 Seventh St Unit 36396616, Middletown, VA 22645
  • /10

    $424,999 New Construction

    • 3 Beds
    • 2 Baths
    • 1,610 Sq Ft

    Onyx Plan at Middletown Place - Seasons, Middletown, VA 22645

    Enjoy single-floor living in this inspired ranch floor plan! At the front of the home, you'll find two bedrooms flanking a full bath. Toward the back, there's a well-appointed kitchen nestled between an elegant dining room and generous great room. A tech center provides added convenience! The laundry is located near the primary bedroom, which has a large walk-in closet and a private bath. A

    Richmond American Homes Builder
    107 Seventh St Unit 36396566, Middletown, VA 22645
  • /115

    $1,250,000

    • 5 Beds
    • 5.5 Baths
    • 6,239 Sq Ft

    180 Newell Dr, Middletown, VA 22645

    Stunning Executive Home Perfect for Entertaining!!Welcome to this luxurious 5-bedroom, 5.5-bathroom haven located at 180 Newell Dr, Middletown, VA. This sprawling estate spans over 6239 square feet, offering a perfect blend of comfort and sophistication.Key Features:**Ensuite Bedrooms** 4 out of the 5 bedrooms come with their own private ensuites, ensuring privacy and

    Melinda Ball Coldwell Banker Premier

    180 Newell Dr, Middletown, VA 22645
  • /29

    $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
  • /62

    $635,000

    • 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
  • /67

    $699,900 Open Sun 2PM - 4PM

    • 6 Beds
    • 4 Baths
    • 4,164 Sq Ft

    43 Little Sorrel Dr, Middletown, VA 22645

    Motivated Seller!! Welcome to the sought-after Jackson’s Meadow subdivision with no HOA! This spacious Quaker-built home was completely remodeled down to the studs in 2021, with everything new inside and out. Offering over 4,000 finished square feet across three levels and backing to the Sly Fox Golf Course, this property has room for everyone. On the upper level, you’ll find 4 bedrooms,

    Camryn Jeremiah NextHome Realty Select

    43 Little Sorrel Dr, Middletown, VA 22645
  • /60

    $769,900

    • 4 Beds
    • 3 Baths
    • 3,120 Sq Ft

    115 Reliance Woods Dr, Middletown, VA 22645

    This exceptional home offers the perfect blend of privacy and convenience, nestled on a beautifully treed lot with serene views from every window—including breathtaking vistas of Skyline Drive from the two rear patios and the upper-level deck off the master bedroom. Despite its tranquil, sanctuary-like setting, the property is less than five minutes from Target, Walmart, Starbucks, and Lowe’s,

    Bruce Crabill Preslee Real Estate

    115 Reliance Woods Dr, Middletown, VA 22645
  • /58

    $1,099,900 Coming Soon

    • 5 Beds
    • 6 Baths
    • 5,335 Sq Ft

    190 Newell Dr, Middletown, VA 22645

    Experience peace and tranquility of life in one of Middletown's most desirable & beautifully maintained communities, "Sheridan Estates"—an intimate enclave of just 8 custom homes, offering an upscale yet welcoming atmosphere, perfect for those who value comfort, style, and serenity with NO HOA! A brief 5 miles to I-81 to Rt 66 makes it an easy commuting distance to downtown Washington DC. Only 1

    Michele Gibson Samson Properties

    190 Newell Dr, Middletown, VA 22645
  • /2

    $685,000 Coming Soon

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

    76 Katie Ln, Middletown, VA 22645

    Beautiful Stone Front Colonial in Sought-After Pineland Park3,887 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 Front Royal.The Jefferson III model by H & H Builders features a stone

    Ken Evans RE/MAX Real Estate Connections

    76 Katie Ln, Middletown, VA 22645
  • /39

    $337,000

    • 3 Beds
    • 2.5 Baths
    • 1,307 Sq Ft

    119 Kensington Cir, Middletown, VA 22645

    Beautiful three-level townhome in the Enfield Knolls community of charming Middletown, VA. The open floor plan is filled with natural light and features a modern kitchen with stainless steel appliances and a moveable island that conveys. Enjoy durable luxury vinyl plank flooring, a composite deck for outdoor relaxation, and the convenience of bedroom-level laundry. With 3 bedrooms, 2.5 baths, and

    Natalie Langford ERA Oakcrest Realty, Inc.

    119 Kensington Cir, Middletown, VA 22645
  • /55

    $1,250,000

    • 4 Beds
    • 3.5 Baths
    • 3,696 Sq Ft

    112 Woods Way, Middletown, VA 22645

    Privacy and Relaxation! Sited well off the road at the high point of a secluded 35 acre site with 400 feet of Shenandoah River frontage this home features expansive windows; solid log construction; a stunning, centrally located, wood-burning fireplace and chimney; gourmet kitchen with stainless steel appliances; and a wrap-around deck above the undisturbed woodlands and North Fork of the

    Bradley Boland Keller Williams Realty Dulles

    112 Woods Way, Middletown, VA 22645
  • /75

    $375,000

    • 4 Beds
    • 2 Baths
    • 1,484 Sq Ft

    2425 Third St, Middletown, VA 22645

    Welcome home to Third St!!! This lovely and well maintained split foyer is on one acre of unrestricted property and also boasts quite a number of upgrades! There is lots of space for entertaining, particularly outside with a fairly level landscape, and in the home there are ample rooms to work with. This home has lots of opportunity for a number of uses; office spaces, guest rooms, hobby

    Nicole Lewis Coldwell Banker Premier

    2425 Third St, Middletown, VA 22645
  • /31

    $440,000

    • 4 Beds
    • 2.5 Baths
    • 1,930 Sq Ft

    163 Emmet St, Middletown, VA 22645

    This 2021-built home is situated on a corner lot with views of I-81. The property features a 20 ft by 10 ft rear deck for outdoor enjoyment. Interior upgrades include luxury vinyl plank flooring in the kitchen, dining area, and all bathrooms, plus white premium kitchen cabinetry. Six ceiling fans with lights are installed throughout (all bedrooms and living room). The home features an

    Alexandre Ardon Corcoran McEnearney

    163 Emmet St, Middletown, VA 22645
  • /30

    $180,000

    • 1 Bed
    • 1 Bath
    • 1,905 Sq Ft

    7189 Middle Rd, Middletown, VA 22645

    ARE YOU LOOKING FOR A FLIP, RENTAL OR AIRBNB? HERE IS YOUR PLACE! 2 DWELLINGS AND GARAGE ON 1.41 ACRES. FORMERLY HAWKINS GROCERY BUILT IN 1946. FUEL TANKS HAVE BEEN REMOVED AND SELLERS HAVE SOIL REPORTS AND THEY ARE CLEAN. NO WELL ON PROPERTY. THERE ARE 3 CISTERNS. HOUSES SHARE CONVENTIONAL SEPTIC.

    Jacquelyn Rizzari MarketPlace REALTY

    7189 Middle Rd, Middletown, VA 22645
  • /19

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,104 Sq Ft

    2432 Laurel Ln, Middletown, VA 22645

    This recently updated three-bedroom, two-bath home is available in the charming town of Middletown, VA. Conveniently located near Main Street, you will quickly appreciate the vibrant community, which features locally owned restaurants, shops, and various community events. The home boasts modern finishes and is filled with an abundance of natural light. The semi-open concept kitchen and living

    Jen Moore ERA Oakcrest Realty, Inc.

    2432 Laurel Ln, 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
  • /12

    $799,000

    • Land
    • 3.84 Acres
    • $208,073 per Acre

    0 Reliance Rd Unit VAFV2024656, 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 VAFV2024656, Middletown, VA 22645
  • /2

    $5,750,000

    • Land
    • 41.57 Acres
    • $138,321 per Acre

    226 Reliance Rd, Middletown, VA 22645

    41.5 acres of prime interstate land perfect for a commercial or industrial development. Zoned acres B2 and remaining RA.

    Jason Aikens RE/MAX Roots

    226 Reliance Rd, Middletown, VA 22645
  • /2

    $525,000

    • Land
    • 2 Acres
    • $262,500 per Acre

    7783 Main St, Middletown, VA 22645

    Prime Development Opportunity in Middletown, VA – 2 +/- Acres behind the Wayside Inn, Backing to Parkland. Access can be from 1st street, or with the right deal from Main streetUnlock the potential of this 2-acre parcel of raw land, a developer’s dream located in the charming town of Middletown, VA. This property offers a rare combination of versatility and scenic tranquility, as it

    Robert Hotaling RE/MAX Allegiance

    7783 Main St, 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
  • /33

    $424,999 New Construction

    • 3 Beds
    • 2 Baths
    • 1,610 Sq Ft

    104 Midsummer Ln, Middletown, VA 22645

    Enjoy single-floor living in this inspired ranch home! At the front of the home, you'll find two bedrooms flanking a full bath. Toward the back, there's a well-appointed kitchen nestled between an elegant dining room and generous great room. A tech center provides added convenience! The laundry is located near the primary bedroom, which has a large walk-in closet and a private bath. A covered

    Richmond American Homes Builder
    104 Midsummer Ln, Middletown, VA 22645
  • /36

    $469,999 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,840 Sq Ft

    102 Midsummer Ln, Middletown, VA 22645

    The main floor of this Coral home 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 home is built a loft.To round out this

    Richmond American Homes Builder
    102 Midsummer Ln, Middletown, VA 22645
  • /35

    $484,999 New Construction

    • 3 Beds
    • 2 Baths
    • 1,610 Sq Ft

    100 Midsummer Ln, Middletown, VA 22645

    Discover this thoughtfully designed Onyx home. Included features: an inviting covered entry; an expansive great room with an electric fireplace; a well-appointed kitchen offering a roomy pantry, a center island and an adjacent dining area; a tech center; a lavish primary suite showcasing a generous walk-in closet and a private bath; a convenient laundry; a deck and an unfinished basement. This

    Richmond American Homes Builder
    100 Midsummer Ln, Middletown, VA 22645
  • /6

    $199,900 Coming Soon

    • 2 Beds
    • 1.5 Baths
    • 1,053 Sq Ft

    2085 Chapel Rd, Middletown, VA 22645

    Welcome home to this charming 2-bedroom, 1-bath Cape Cod just outside the town limits of Middletown, VA! Offering comfort and convenience in a peaceful setting, this home is full of character and potential. Don’t miss the opportunity to make it yours—more photos coming soon!

    Abby Walters Preslee Real Estate

    2085 Chapel Rd, 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 $516,733.
Are home prices dropping in Middletown?
Yes, home prices in Middletown are down 3% in the last 12 months.
How many homes have sold over the last 12 months in Middletown, VA?
118 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, 22641 and 22630.
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 6.19%, your estimated principal and interest payment would be $2,350 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $101K a year to afford the median home price in Middletown.
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, Middletown Elementary School and Robert E. Aylor Middle 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
$320,000
Average Price Per Sq Ft
$211
Number of Homes for Sale
20
Last 12 months Home Sales
118
Months of Supply
2.00
Median List Price
$479,999
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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