Middletown, VA Homes

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  /93

  $749,900

  $25K PRICE DROP Under Contract

  • 6 Beds
  • 5 Baths
  • 3,908 Sq Ft

  80 Little Sorrel Dr, Middletown, VA 22645

  Sprawling Versatility & Ultimate Entertainment Estate in a Premier Community! Welcome to this expansive 6-bedroom, 5-full-bathroom estate offering an incredible 3,908 finished square feet of highly adaptable living space on a premium 1-acre lot. Nestled within a highly desirable golf course neighborhood in Warren County minutes from I-66 and I-81 for easy commutes, this home seamlessly balances

  

  Catherine DeMay

  Real Broker, LLC

  80 Little Sorrel Dr, Middletown, VA 22645
• Explore Middletown

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  /47

  $3,100 Per Month

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

  7919 Church St, Middletown, VA 22645

  Welcome to historic Church Street in the heart of Middletown! This beautifully updated Victorian offers over 3,000 square feet of living space, 3 bedrooms, 2.5 baths, a dedicated office, a fully fenced backyard, and plenty of indoor and outdoor space—all within walking distance of local restaurants, parks, and shopping. Inside, you'll find beautiful hardwood floors throughout, soaring ceilings,

  Liz Owings Samson Properties

  7919 Church St, Middletown, VA 22645
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  /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 $259,916

  Last Listing Agent Howard Kronthal Exit Success Realty

  7752 Pleasant View Ave, Middletown, VA 22645
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  /58

  Est $684,012

  Not Listed For Sale

  7040 Valley Pike, Middletown, VA 22645

  • 4 Beds
  • 2.5 Baths
  • 2,671 Sq Ft
  • Built 2022

  7040 Valley Pike, Middletown, VA 22645

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Daryl Stout Realty One Group Key Properties
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  /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
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  /36

  $2,150 Per Month

  • 3 Beds
  • 2 Baths
  • 1,525 Sq Ft
  • House for Rent

  7984 Main St, Middletown, VA 22645

  Beautiful Rancher that has been meticulously maintained, living room with pellet stove opens to dining area, very functional kitchen with large pantry, separate laundry room. Huge detached oversized 2 car garage with stairs to fully floored upper level, alley access to rear parking and garage, level rear/front yard, covered front porch. Easy access to I81 and 66. Note: W/D shown in pictures are

  Roxane Morrison NextHome Realty Select

  7984 Main St, 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 $487,653

  Richmond American Middletown Place - Seasons

  121 Midsummer Ln, Middletown, VA 22645
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  /34

  Est $402,374

  Not Listed For Sale

  310 Coville St, Middletown, VA 22645

  • 3 Beds
  • 2.5 Baths
  • 1,352 Sq Ft
  • Built 2020

  310 Coville St, Middletown, VA 22645

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Doug Rapport Berkshire Hathaway HomeServices PenFed Realty
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  /45

  $585,000

  Open Sat 1PM - 3PM

  • 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

  

  Lori Bales

  Keller Williams Realty

  2239 Sixth 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 $404,929

  Last Listing Agent Dinora Chacon Real Broker, LLC

  201 Coville St, Middletown, VA 22645
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  /12

  Not Listed For Sale

  3 Huttle Rd, Middletown, VA 22645

  3 Huttle Rd, Middletown, VA 22645

  Last Sold Summary

  • 147 Days On Market

  Last Listing Agent Colleen Flynn Property Collective
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  /52

  $649,000

  • 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

  

  Lori Bales

  Keller Williams Realty

  7760 Main St, Middletown, VA 22645
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  /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 $446,036

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

  163 Emmet St, Middletown, VA 22645
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  /88

  Est $905,508

  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

  Last Listing Agent RoxAnn Grimes RE/MAX Roots
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  /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
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  /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 $690,008

  Last Listing Agent Traci Shoberg Samson Properties

  111 Jackson Place, Middletown, VA 22645
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  /49

  Est $958,788

  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

  Last Listing Agent Cathy Strittmater Keller Williams Realty/Lee Beaver & Assoc.
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  /69

  $415,000

  $5K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft

  2105 Shawn Dr, Middletown, VA 22645

  Price Reduced!! 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

  Peter Van Cleave Real Broker, LLC

  2105 Shawn Dr, Middletown, VA 22645
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  /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 $441,368

  Last Listing Agent Kimberlee Wergland Realty ONE Group Old Towne

  2137 Reliance Rd, Middletown, VA 22645
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  /62

  Est $1,181,770

  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

  Last Listing Agent LESLIE WEBB Long & Foster Real Estate, Inc.
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  /77

  $700,000

  $65K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  155 Turkey Ln, Middletown, VA 22645

  CURRENT CONTRACT HAS A HOME SALE CONTINGENCY. SELLERS WILL CONSIDER BACK-UP OFFERS. ANOTHER HUGE PRICE REDUCTION OF $25,000. APPRAISED VALUE IS $764,000. HOME LISTED $64,000 BELOW APPRAISAL. SELLERS WILL CONSIDER ALL OFFERS. 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

  Thomas Campbell Fathom Realty

  155 Turkey Ln, 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
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  /14

  Est $3,079,037

  Not Listed For Sale

  7165 Valley Pike, Middletown, VA 22645

  7165 Valley Pike, Middletown, VA 22645

  Last Sold Summary

  • 2,029 Days On Market

  Last Listing Agent Jim Guisewhite Commercial Specialists
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  /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
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  /96

  $815,000

  Sold Jul 30, 2026

  356 Chimney Cir, Middletown, VA 22645

  • 6 Beds
  • 5.5 Baths
  • 5,633 Sq Ft
  • Built 2005

  Last Sold Summary

  • 1% Below List Price
  • $145/SF
  • 10 Days On Market

  Current Estimated Value $726,818

  Last Listing Agent Julie Teets ERA Oakcrest Realty, Inc.

  356 Chimney Cir, Middletown, VA 22645
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  /14

  Not Listed For Sale

  0 S Buckton Rd, Middletown, VA 22645

  0 S Buckton Rd, Middletown, VA 22645

  Last Sold Summary

  • 137 Days On Market

  Last Listing Agent Chad Pangle Whitetail Properties Real Estate, LLC
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  /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

  Christine Binnix Samson Properties

  289 Reliance Woods Dr, 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 $1,189,965

  Last Listing Agent Bradley Boland Keller Williams Realty Dulles

  112 Woods Way, Middletown, VA 22645
• 

  

  /43

  Est $553,643

  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

  Last Listing Agent HERSHEY LLANES Samson Properties
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  /77

  $700,000

  Coming Soon

  • 3 Beds
  • 3.5 Baths
  • 2,242 Sq Ft

  440 Chimney Cir, Middletown, VA 22645

  FIRST TIME ON THE MARKET!Discover the exceptional charm of this custom-built, one-owner home, gracefully positioned on a picturesque 2.33-acre knoll in desirable Chimney Hills Estates. Beautifully maintained and thoughtfully designed, this 2017 custom home built by Donald Adams, offers a wonderful blend of elegance, comfort, and easy living. The home is heated and cooled with a heatpump and

  Darcy Amburn Colony Realty

  440 Chimney Cir, Middletown, VA 22645
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  /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 $490,528

  Richmond American Middletown Place - Seasons

  120 Midsummer Ln, Middletown, VA 22645
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  /7

  Not Listed For Sale

  114 Midsummer Ln, Middletown, VA 22645

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

  114 Midsummer Ln, Middletown, VA 22645

  Last Sold Summary

  • 183 Days On Market

  Last Listing Agent Jay Day LPT Realty, LLC
• 

  

  /55

  $634,900

  $15K PRICE DROP Under Contract

  • 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
• 

  

  /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 $297,464

  Last Listing Agent Jacquelyn Rizzari MarketPlace REALTY

  7189 Middle Rd, Middletown, VA 22645
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  /6

  Not Listed For Sale

  119 Midsummer Ln, Middletown, VA 22645

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft
  • Built 2025

  119 Midsummer Ln, Middletown, VA 22645

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Jay Day LPT Realty, LLC
• 

  

  /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
• 

  

  /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 $303,127

  Last Listing Agent Joseph Doyle RE/MAX Real Estate Connections

  2155 Massanutten Dr, Middletown, VA 22645
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  /7

  Not Listed For Sale

  118 Midsummer Ln, Middletown, VA 22645

  • 3 Beds
  • 2.5 Baths
  • 1,850 Sq Ft
  • Built 2025

  118 Midsummer Ln, Middletown, VA 22645

  Last Sold Summary

  • 145 Days On Market

  Last Listing Agent Jay Day LPT Realty, LLC
• 

  

  /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
• 

  

  /19

  $214,900

  Sold Jan 30, 2026

  2085 Chapel Rd, Middletown, VA 22645

  • 3 Beds
  • 2.5 Baths
  • 1,053 Sq Ft
  • Built 1960

  Last Sold Summary

  • 8% Above List Price
  • $204/SF
  • 3 Days On Market

  Current Estimated Value $220,192

  Last Listing Agent Abby Walters Preslee Real Estate

  2085 Chapel Rd, Middletown, VA 22645

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