2,690

Middletown, VA Homes

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  • /31

    $325,000

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,425 Sq Ft

    7786 Carolyn Ave, Middletown, VA 22645

    Pics Coming Soon. Home needs a little TLC. With 1,425 square feet of thoughtfully designed living space, this residence features three inviting bedrooms and a full bathroom, ideal for both relaxation and entertaining. Step inside to discover a welcoming atmosphere that needs some TLC, highlighted by a cozy family room that flows seamlessly into the living room. The traditional floor plan is

    Agent Photo

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    Berkshire Hathaway HomeServices PenFed Realty

    (540) 530-3871

    7786 Carolyn Ave, Middletown, VA 22645
  • /48

    $3,250 Per Month

    • 4 Beds
    • 2.5 Baths
    • 3,168 Sq Ft
    • House for Rent

    7919 Church St, Middletown, VA 22645

    Welcome to historic Church Street! Nestled in the heart of charming Middletown, this stunning Victorian offers over 3,000 square feet of finished living space on a beautifully landscaped half-acre lot—just steps from shopping, parks, and local restaurants. Meticulously updated with today’s conveniences while preserving its rich character, this home is full of charm at every turn. Step through the

    Liz Owings Samson Properties

    7919 Church St, Middletown, VA 22645
  • /27

    $237,000

    Sold Nov 17, 2025

    7752 Pleasant View Ave, Middletown, VA 22645

    • 3 Beds
    • 1 Bath
    • 1,273 Sq Ft
    • Built 1978

    Last Sold Summary

    • $186/SF
    • 16 Days On Market

    Current Estimated Value $262,144

    Last Listing Agent Howard Kronthal Exit Success Realty

    7752 Pleasant View Ave, Middletown, VA 22645
    • /43

      Est $552,033

      Not Listed For Sale

      109 Dursley Cir, Middletown, VA 22645

      • 5 Beds
      • 3 Baths
      • 2,471 Sq Ft
      • Built 2024
      109 Dursley Cir, Middletown, VA 22645

      Last Sold Summary

      • 14 Days On Market

  • /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
  • /12

    $3,600

    Total Monthly Price

    • 4 Beds
    • 3 Baths
    • 3,120 Sq Ft
    • House for Rent

    115 Reliance Woods Dr, Middletown, VA 22645

    Knock! Knock! Spring weather is finally at the door and it's time to let it in! Welcome to 115 Reliance Woods Drive in Middletown, VA! This gorgeous four bedroom single family home with a large two car garage will fit the doctor's orders! The country setting will take your breath away. The home is a refreshing example of private, peaceful living with modern conveniences like proximity to

    115 Reliance Woods Dr, Middletown, VA 22645
  • /31

    $489,999

    Sold Oct 31, 2025

    121 Midsummer Ln, Middletown, VA 22645

    • 4 Beds
    • 2.5 Baths
    • 1,840 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $266/SF
    • 14 Days On Market

    Current Estimated Value $501,283

    Richmond American Homes Middletown Place - Seasons

    121 Midsummer Ln, Middletown, VA 22645
    • /34

      Est $358,004

      Not Listed For Sale

      153 Kensington Cir, Middletown, VA 22645

      • 3 Beds
      • 2.5 Baths
      • 1,307 Sq Ft
      • Built 2024
      153 Kensington Cir, Middletown, VA 22645

      Last Sold Summary

      • 14 Days On Market

  • /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
  • /10

    $2,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,796 Sq Ft
    • House for Rent

    7957 Main St, Middletown, VA 22645

    Step into the charm and character of this beautifully restored historic home, where timeless architecture meets modern convenience. Recently renovated throughout, this unique property offers updated finishes while preserving the craftsmanship and appeal that make historic homes so special. The property is zoned to allow for both residential and business use, creating a rare opportunity for

    Stacey Rowe Real Broker LLC

    7957 Main St, Middletown, VA 22645
  • /29

    $405,000

    Sold May 11, 2026

    201 Coville St, Middletown, VA 22645

    • 3 Beds
    • 2 Baths
    • 1,243 Sq Ft
    • Built 2019

    Last Sold Summary

    • $326/SF
    • 13 Days On Market

    Current Estimated Value $403,512

    Last Listing Agent Dinora Chacon Real Broker, LLC

    201 Coville St, Middletown, VA 22645
    • /54

      Est $390,715

      Not Listed For Sale

      1314 Reliance Rd, Middletown, VA 22645

      • 3 Beds
      • 2 Baths
      • 1,390 Sq Ft
      • Built 1918
      1314 Reliance Rd, Middletown, VA 22645

      Last Sold Summary

      • 4 Days On Market

  • /2

    $2,300,000

    Under Contract
    • Land
    • 183.19 Acres
    • $12,555 per Acre

    0 Reliance Rd Unit VAWR139520, Middletown, VA 22645

    Large tract of land bordering the Sly Fox Golf Club. 183 wooded acres suitable for subdivision. The seller has created a sketch showing 36 lots for this subdivision that is BY RIGHT SO it cannot be denied! there are 24 1-acre lots; 9 ten-acre lots; 2 - 22 acre lots; and 1 - 20 acre lot & innternal streets that would stem from Reliance Rd. Tax Map #11 13 (55.2704 ac), TM#11 12 (103.00 ac), TM# 11

    Tana Hoffman Sager Real Estate

    0 Reliance Rd Unit VAWR139520, Middletown, VA 22645
  • /27

    $1,995 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,307 Sq Ft
    • Townhouse for Rent

    141 Grand St, Middletown, VA 22645

    Looking for tenants with 650 + credit score with clean background and earning 3x times the annual rent amount.This Juniper model ! Brand new end unit 3-Bedroom, 2-Bath Townhomes with a 1-car garage in historic Middletown, Convenient and close access to I-81, I-66 and Route 11 minutes from Front Royal and Winchester. Move in Ready . Any questions regarding the property please contact Listing

    Agnes Francis Century 21 Redwood Realty

    141 Grand St, Middletown, VA 22645
  • /45

    $439,000

    Sold Mar 09, 2026

    163 Emmet St, Middletown, VA 22645

    • 4 Beds
    • 2.5 Baths
    • 1,930 Sq Ft
    • Built 2021

    Last Sold Summary

    • $227/SF
    • 63 Days On Market

    Current Estimated Value $442,072

    Last Listing Agent Richard Kozlowski Long & Foster Real Estate, Inc.

    163 Emmet St, Middletown, VA 22645
    • /29

      Est $329,140

      Not Listed For Sale

      7783 Church St, Middletown, VA 22645

      • 2 Beds
      • 1 Bath
      • 1,007 Sq Ft
      • Built 1964
      7783 Church St, Middletown, VA 22645

      Last Sold Summary

      • 43 Days On Market

  • /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
  • /60

    $645,000

    Sold Aug 29, 2025

    111 Jackson Place, Middletown, VA 22645

    • 3 Beds
    • 2 Baths
    • 2,401 Sq Ft
    • Built 2004

    Last Sold Summary

    • $269/SF
    • 34 Days On Market

    Current Estimated Value $681,895

    Last Listing Agent Traci Shoberg Samson Properties

    111 Jackson Place, Middletown, VA 22645
    • /31

      Est $299,616

      Not Listed For Sale

      1282 Hites Rd, Middletown, VA 22645

      • 3 Beds
      • 1 Bath
      • 1,344 Sq Ft
      • Built 1945
      1282 Hites Rd, Middletown, VA 22645

      Last Sold Summary

      • 32 Days On Market

  • /54

    $2,999,000

    • 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
  • /56

    $420,000

    Sold Dec 12, 2025

    2137 Reliance Rd, Middletown, VA 22645

    • 3 Beds
    • 1.5 Baths
    • 1,776 Sq Ft
    • Built 1962

    Last Sold Summary

    • $236/SF
    • 3 Days On Market

    Current Estimated Value $437,624

    Last Listing Agent Kimberlee Wergland Realty ONE Group Old Towne

    2137 Reliance Rd, Middletown, VA 22645
    • /52

      Est $894,327

      Not Listed For Sale

      424 Riley Mill Ln, Middletown, VA 22645

      • 4 Beds
      • 2.5 Baths
      • 3,224 Sq Ft
      • Built 2011
      424 Riley Mill Ln, Middletown, VA 22645

      Last Sold Summary

      • 177 Days On Market

  • /58

    $359,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    6717 Middle Rd, Middletown, VA 22645

    Nestled in a serene setting, this charming ranch-style home offers a perfect blend of comfort and functionality. Built in 1965, this well-maintained residence spans 1,560 square feet and features three inviting bedrooms and two full bathrooms, making it an ideal retreat for those seeking a cozy yet spacious living environment. Step inside to discover a warm and welcoming atmosphere, accentuated

    Kimberly Holzer Ross Real Estate

    6717 Middle Rd, Middletown, VA 22645
  • /27

    $372,000

    Sold Jul 02, 2025

    2414 Laurel Ln, Middletown, VA 22645

    • 3 Beds
    • 2 Baths
    • 1,508 Sq Ft
    • Built 2000

    Last Sold Summary

    • $247/SF
    • 79 Days On Market

    Current Estimated Value $384,339

    Last Listing Agent Jami Castillo CENTURY 21 New Millennium

    2414 Laurel Ln, Middletown, VA 22645
    • /29

      Est $477,982

      Not Listed For Sale

      300 Coville St, Middletown, VA 22645

      • 5 Beds
      • 2.5 Baths
      • 2,210 Sq Ft
      • Built 2020
      300 Coville St, Middletown, VA 22645

      Last Sold Summary

      • 0 Days On Market

  • /38

    $430,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 1,810 Sq Ft

    7760 Church St, Middletown, VA 22645

    Comfortable one-level living in the heart of Middletown! This well-maintained 4-bedroom, 3-bath ranch home offers a functional layout, spacious backyard, and additional potential in the unfinished basement. Recent updates include a brand-new rear deck completed in 2026, perfect for relaxing or entertaining outdoors. Conveniently located near I-81, shopping, dining, schools, and historic downtown

    Abby Walters Preslee Real Estate

    7760 Church St, Middletown, VA 22645
  • /11

    $82,000

    Sold Apr 10, 2026

    0 St, Middletown, VA 22645

    • Land
    • 18,295 Sq Ft
    • $195,238 per Acre

    Last Sold Summary

    • 18% Below List Price
    • 28 Days On Market

    Last Listing Agent Chris Roszko Colony Realty

    0 St, Middletown, VA 22645
    • /62

      Est $1,665,811

      Not Listed For Sale

      106 Crest River Dr, Middletown, VA 22645

      • 9 Beds
      • 10 Baths
      • 10,065 Sq Ft
      • Built 2000
      106 Crest River Dr, Middletown, VA 22645

      Last Sold Summary

      • 338 Days On Market

  • /77

    $725,000

    Open Sun 1PM - 4PM $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,748 Sq Ft

    155 Turkey Ln, Middletown, VA 22645

    HUGE PRICE REDUCTION OF $39,000. APPRAISED VALUE IS $764,000. MOTIVATED SELLERS MOVING DUE TO NEW JOB. PLEASE MAKE AN APPOINTMENT TO SEE. NO DRIVE BYS PLEASE. Nestled within the serene enclave of River Ridge on the Shenandoah, this exquisite ranch-style home built in 2022, offers a harmonious blend of modern luxury and natural beauty. Spanning an impressive 20 acres, the property is enveloped by

    Thomas Campbell Fathom Realty

    155 Turkey Ln, Middletown, VA 22645
  • /55

    $1,125,000

    Sold Jan 16, 2026

    112 Woods Way, Middletown, VA 22645

    • 4 Beds
    • 3.5 Baths
    • 3,696 Sq Ft
    • Built 2005

    Last Sold Summary

    • $304/SF
    • 35 Days On Market

    Current Estimated Value $1,066,165

    Last Listing Agent Bradley Boland Keller Williams Realty Dulles

    112 Woods Way, Middletown, VA 22645
    • /12

      Not Listed For Sale

      3 Huttle Rd, Middletown, VA 22645

      3 Huttle Rd, Middletown, VA 22645

      Last Sold Summary

      • 147 Days On Market

  • /66

    $690,000

    $10K PRICE DROP Under Contract
    • 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 4,100 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
  • /32

    $479,999

    Sold Oct 31, 2025

    120 Midsummer Ln, Middletown, VA 22645

    • 3 Beds
    • 2.5 Baths
    • 1,980 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $242/SF
    • 14 Days On Market

    Current Estimated Value $498,733

    Richmond American Homes Middletown Place - Seasons

    120 Midsummer Ln, Middletown, VA 22645
    • /88

      Est $917,660

      Not Listed For Sale

      122 Quincey Mill Ct, Middletown, VA 22645

      • 5 Beds
      • 3.5 Baths
      • 5,150 Sq Ft
      • Built 2018
      122 Quincey Mill Ct, Middletown, VA 22645

      Last Sold Summary

      • 27 Days On Market

  • /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
  • /30

    $150,000

    Sold Dec 22, 2025

    7189 Middle Rd, Middletown, VA 22645

    • 1 Bed
    • 1 Bath
    • 1,905 Sq Ft
    • Built 1946

    Last Sold Summary

    • $79/SF
    • 84 Days On Market

    Current Estimated Value $263,912

    Last Listing Agent Jacquelyn Rizzari MarketPlace REALTY

    7189 Middle Rd, Middletown, VA 22645
    • /49

      Est $929,479

      Not Listed For Sale

      7252 Middle Rd, Middletown, VA 22645

      • 4 Beds
      • 3.5 Baths
      • 4,632 Sq Ft
      • Built 1841
      7252 Middle Rd, Middletown, VA 22645

      Last Sold Summary

      • 2 Days On Market

  • /47

    $800,000

    Open Sat 1PM - 3PM
    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft

    906 Cauthorn Mill Rd, Middletown, VA 22645

    Tucked into the woods along the banks of Dry Run, this 21.78-acre property delivers the kind of privacy, usable land, and outdoor lifestyle that delivers complete comfort. The driveway follows the rocky streambed and natural beauty of Dry Run before proceeding through mature hardwoods that surround this secluded all-brick ranch, rich with wildlife, trails, and recreational opportunity. The land

    Karen Smith Pearson Smith Realty, LLC

    906 Cauthorn Mill Rd, Middletown, VA 22645
  • /13

    $300,000

    Sold Feb 23, 2026

    2155 Massanutten Dr, Middletown, VA 22645

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1977

    Last Sold Summary

    • $250/SF
    • 7 Days On Market

    Current Estimated Value $301,861

    Last Listing Agent Joseph Doyle RE/MAX Real Estate Connections

    2155 Massanutten Dr, Middletown, VA 22645
    • /62

      Est $1,132,594

      Not Listed For Sale

      181 Darterjo Dr, Middletown, VA 22645

      • 4 Beds
      • 6 Baths
      • 4,443 Sq Ft
      • Built 2017
      181 Darterjo Dr, Middletown, VA 22645

      Last Sold Summary

      • 5 Days On Market

Showing Results 1 - 40, Page 1 of 18

Home Prices in Middletown, VA

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
$400,000
Median 1 Bedroom Sale Price
$150,000
Average Price Per Sq Ft
$226
Number of Homes for Sale
11
Last 12 months Home Sales
79
Months of Supply
1.70
Median List Price
$482,449
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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