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Middletown, VA Homes for Sale

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  • /12

    $624,900 Coming Soon

    • 3 Beds
    • 3.5 Baths
    • 3,440 Sq Ft

    2064 Sulphur Springs Rd, Middletown, VA 22645

    Set on almost 8 unrestricted acres, this property offers a rare combination of open farmland, wooded privacy, and functional outbuildings. Most of the acreage is already fenced, perfect for animals, hobby farming, or continue to hay the fields. A pole barn and woodworking barn add even more utility, making this an ideal property for those seeking both space and versatility.At the heart of

    Agent Photo

    Bradley Comstock

    ERA Oakcrest Realty, Inc.

    (540) 501-7073

    2064 Sulphur Springs Rd, 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

    Builder Photo

    Richmond American Homes

    Builder

    107 Seventh St Unit 36396779, Middletown, VA 22645
  • /11

    $469,999 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

    Builder Photo

    Richmond American Homes

    Builder

    107 Seventh St Unit 36396616, Middletown, VA 22645
  • /10

    $449,999 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

    Builder Photo

    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 convenience.**Panoramic

    Melinda Ball Coldwell Banker Premier

    180 Newell Dr, Middletown, VA 22645
  • /62

    $650,000

    • 3 Beds
    • 2 Baths
    • 2,338 Sq Ft

    374 Boyers Mill Ln, Middletown, VA 22645

    Nestled on a sprawling 5-acre lot, this exquisite log home embodies the perfect blend of rustic charm and modern luxury. Built in 2002, the property showcases exceptional craftsmanship with its stunning log and wood siding, creating a warm and inviting exterior that harmonizes beautifully with the surrounding natural landscape. Soak in the tranquil views of the lush landscape and trees along with

    Bridget Aikens Colony Realty

    374 Boyers Mill Ln, Middletown, VA 22645
  • /67

    $779,000

    • 5 Beds
    • 3.5 Baths
    • 4,161 Sq Ft

    170 Darterjo Dr, Middletown, VA 22645

    Welcome to 170 Darterjo Drive — where commuter convenience meets private country living in style.Included Buyer Perk: Purchase at full price and receive a two-year, fully transferable home warranty at no cost — premium coverage that protects your investment and provides peace of mind well beyond closing.Located just minutes from I-81 and I-66, this meticulously maintained

    Traci Shoberg RE/MAX Roots

    170 Darterjo 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
  • /59

    $699,999

    • 4 Beds
    • 2.5 Baths
    • 4,115 Sq Ft

    627 Chimney Cir, Middletown, VA 22645

    Enjoy the perfect blend of privacy and convenience with this beautiful 3+ acre property in Middletown! This 3-level home offers an open floor plan with a formal living room (currently used as a home office), a spacious kitchen with granite counters, a large island, and newer appliances. The kitchen flows into the family room with a cozy fireplace and a stunning sunroom overlooking the fenced

    Deborah Matthews ERA Oakcrest Realty, Inc.

    627 Chimney Cir, Middletown, VA 22645
  • /61

    $699,900

    • 4 Beds
    • 2.5 Baths
    • 3,255 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
  • /31

    $489,999 New Construction

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

    121 Midsummer Ln, Middletown, VA 22645

    Explore this thoughtfully designed Coral home, ready for quick move-in. Included features: a welcoming porch, an expansive great room boasting an electric fireplace, a well-appointed kitchen offering a roomy pantry and a center island, an open dining area, a stunning primary suite showcasing a large walk-in closet and a private bath, a convenient laundry, an unfinished walkout basement and a

    Builder Photo

    Richmond American Homes

    Builder

    121 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

    Builder Photo

    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

    Builder Photo

    Richmond American Homes

    Builder

    100 Midsummer Ln, Middletown, VA 22645
  • /32

    $479,999 New Construction

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

    120 Midsummer Ln, Middletown, VA 22645

    Discover this exceptional Citrine home. Included features: a charming covered entry, a large great room with an electric fireplace, an open dining area, an inviting kitchen offering a roomy pantry and a center island, a stunning primary suite showcasing a spacious walk-in closet and a private bath, a convenient laundry, an unfinished basement, a composite deck and a 2-car garage. This could be

    Builder Photo

    Richmond American Homes

    Builder

    120 Midsummer Ln, Middletown, VA 22645
  • /33

    $549,999 New Construction

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

    107 Seventh St, Middletown, VA 22645

    MODEL HOME FOR SALE! You'll love the Onyx ranch floor plan! Just off the entry, you'll find two secondary bedrooms flanking a full bath. Toward the back of the home, there's a spacious open great room with an electric fireplace set in a tiled wall, a dining area with built-in cabinetry, a convenient tech center and a covered patio. The kitchen offers a wide center island, a built-in pantry,

    Jay Day LPT Realty, LLC

    107 Seventh St, Middletown, VA 22645
  • /49

    $469,999 New Construction

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

    106 Midsummer Ln, Middletown, VA 22645

    Discover this exceptional Citrine home. Included features: a charming, covered entry, a large great room with an electric fireplace, an open dining area, an inviting kitchen offering a roomy pantry and a center island, a stunning primary suite showcasing a spacious walk-in closet and a private bath, a convenient laundry, an unfinished basement, a deck landing and a 2-car garage. This could be

    Jay Day LPT Realty, LLC

    106 Midsummer Ln, Middletown, VA 22645
  • /30

    $200,000

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

    7189 Middle Rd, Middletown, VA 22645

    INVESTORS BRING YOUR CASH! 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
  • /27

    $275,000

    • 3 Beds
    • 1 Bath
    • 1,273 Sq Ft

    7752 Pleasant View Ave, Middletown, VA 22645

    Well maintained rancher with a fully fenced backyard perfect for outdoor entertainment with a covered bar area and composite decking. Kitchen is outfitted with stainless steel appliances, a propane heater and flue for a wood stove, pass-through to the family room that is equipped with a propane corner fireplace and LVP flooring. Updated bath with 12x12 tile flooring, soaking tub/shower, update

    Howard Kronthal Exit Success Realty

    7752 Pleasant View Ave, Middletown, VA 22645
  • /8

    $575,000

    • Land
    • 2 Acres
    • $287,500 per Acre

    7632 Main St, Middletown, VA 22645

    Prime 2-Acre Commercial Opportunity in the Heart of Middletown, VA – Zoned B1Seize this rare chance to own 2 acres of prime road-front property on Main Street in charming Middletown, Virginia — where small-town charm meets big potential. This parcel is part of a 3-lot package totaling approximately 2.00 acres, being sold together for $575,000 (includes 7656 and 7672 Main Street). With B1

    Cathy Ghattas EXP Realty, LLC

    7632 Main St, Middletown, VA 22645
  • /11

    $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

    $449,999 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

    Builder Photo

    Richmond American Homes

    Builder

    104 Midsummer Ln, Middletown, VA 22645
  • /30

    $449,999 New Construction

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

    107 Midsummer Ln, Middletown, VA 22645

    Explore this eye-catching Coral home, ready for quick move-in. Included features: a welcoming porch, a large great room boasting an electric fireplace, a thoughtfully designed kitchen offering a roomy pantry and a center island, an open dining area, a stunning primary suite showcasing an immense walk-in closet and a private bath, an airy loft, a laundry and an unfinished walkout basement. This

    Builder Photo

    Richmond American Homes

    Builder

    107 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
  • /12

    $424,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,779 Sq Ft

    6776 Valley Pike, Middletown, VA 22645

    "Upgrades On Valley Pike" This 3-bedroom, 2 full bath, extremely well-maintained ranch style home is one you won't want to miss! Beautiful kitchen with stainless steel appliances that was updated in 2019! Great sized living room and den style room with wood burning fireplace (has an electric fireplace insert in it currently that conveys). Primary bedroom with private bathroom that was updated in

    Matt Kilmer Samson Properties

    6776 Valley Pike, Middletown, VA 22645
  • /23

    $399,000

    • 3 Beds
    • 2 Baths
    • 2,704 Sq Ft

    1449 Reliance Rd, Middletown, VA 22645

    Circa 1885 home from yesteryear needs some TLC to shine again. This property will likely be a cash or rehab loan property only. Traditional financing will not qualify due to condition and safety issues in home and on property.

    Jamie Cook Treck Realty LLC

    1449 Reliance 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 $508,243.
Are home prices dropping in Middletown?
Yes, home prices in Middletown are down 5% in the last 12 months.
How many homes have sold over the last 12 months in Middletown, VA?
126 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 6.35%, your estimated principal and interest payment would be $2,390 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $102K 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
24
Last 12 months Home Sales
126
Months of Supply
2.30
Median List Price
$479,999
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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