Middletown, NY Homes

• 

  $525,000

  Sold Apr 10, 2026

  3 Ben Lomond Dr, Middletown, NY 10941

  • 5 Beds
  • 2 Baths
  • 2,515 Sq Ft
  • Built 1975

  Last Sold Summary

  • $209/SF
  • 19 Days On Market

  Current Estimated Value $517,669

  Last Listing Agent Joseph Rubeo KW Hudson Valley Untied

  3 Ben Lomond Dr, Middletown, NY 10941
• 

  Est $805,625

  Not Listed For Sale

  427 Kirbytown Rd, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 3,350 Sq Ft
  • Built 1999

  427 Kirbytown Rd, Middletown, NY 10940

  Last Sold Summary

  • 110 Days On Market
• 

  

  

  /13

  $275,000

  • 2 Beds
  • 2.5 Baths
  • 1,348 Sq Ft

  11 Jordan Ln, Middletown, NY 10940

  Welcome to 11 Jordan Lane, Middletown, NY. This 2-bedroom, 2-bathroom condo offers a practical floor plan and a convenient location close to shopping, dining, schools, healthcare facilities, and major commuter routes.With strong potential and a desirable location, the property presents an excellent opportunity for investors seeking immediate rental income or buyers looking to add value

  Richu Saj Kerala Realty, LLC

  11 Jordan Ln, Middletown, NY 10940
• 

  $440,000

  Sold Apr 14, 2026

  35 East Ave, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,939 Sq Ft
  • Built 1900

  Last Sold Summary

  • 2% Above List Price
  • $227/SF
  • 26 Days On Market

  Current Estimated Value $397,687

  Last Listing Agent Gail Rachlin KW Hudson Valley Untied

  35 East Ave, Middletown, NY 10940
• 

  Est $601,572

  Not Listed For Sale

  1053 Kirby Place, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 2,912 Sq Ft
  • Built 1986

  1053 Kirby Place, Middletown, NY 10940

  Last Sold Summary

  • 75 Days On Market
• 

  

  /50

  $899,000

  $40K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,894 Sq Ft

  114 Last Rd, Middletown, NY 10941

  Distinctive 11-Acre Country Retreat - More than a home, this property delivers a lifestyle defined by space, privacy, and ease. Set across two parcels totaling 11.1 acres, this distinctive Cape Cod combines thoughtful design and easy, everyday living. From the expansive covered front porch to the farmhouse-style entry, the home immediately feels airy and inviting. Inside, the home balances warmth

  Michelle Genatempo Howard Hanna Rand Realty

  114 Last Rd, Middletown, NY 10941
• 

  $328,000

  Sold Feb 03, 2026

  24 Kent Ct, Middletown, NY 10940

  • 2 Beds
  • 2.5 Baths
  • 1,241 Sq Ft
  • Built 1992

  Last Sold Summary

  • 1% Above List Price
  • $264/SF
  • 30 Days On Market

  Current Estimated Value $323,690

  Last Listing Agent Jonathon Lee KW Hudson Valley Untied

  24 Kent Ct, Middletown, NY 10940
• 

  Est $458,482

  Not Listed For Sale

  148 Camp Stadie Rd, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,720 Sq Ft
  • Built 1959

  148 Camp Stadie Rd, Middletown, NY 10940

  Last Sold Summary

  • 26 Days On Market
• 

  

  /47

  $575,000

  Pending

  • 3 Beds
  • 3 Baths
  • 2,133 Sq Ft

  153 Ridge Dr, Middletown, NY 10940

  Searching for a 3-bed raised ranch in Middletown with land, modern finishes, and room to enjoy the outdoors? 3-bedroom, 3-bath home offering over 2,100 sq ft of living space on 11.4 private acres in the Minisink Valley School District. Built in 2022, this property combines contemporary comfort with the privacy and flexibility many Hudson Valley buyers are looking for. Inside, vaulted ceilings and

  Lady Castro eXp Realty

  153 Ridge Dr, Middletown, NY 10940
• 

  $270,000

  Sold Oct 29, 2025

  63 Pierson Hill Rd, Middletown, NY 10940

  • 2 Beds
  • 1.5 Baths
  • 896 Sq Ft
  • Built 1979

  Last Sold Summary

  • $301/SF
  • 11 Days On Market

  Current Estimated Value $289,141

  Last Listing Agent Jackie Siracuse Absolute Real Estate of NY Inc

  63 Pierson Hill Rd, Middletown, NY 10940
• 

  Est $464,959

  Not Listed For Sale

  634 Pocatello Rd, Middletown, NY 10940

  • 4 Beds
  • Built 1880

  634 Pocatello Rd, Middletown, NY 10940

  Last Sold Summary

  • 185 Days On Market
• 

  

  /29

  $439,990

  Pending

  • 5 Beds
  • 2 Baths
  • 2,586 Sq Ft

  14 Bonnell St, Middletown, NY 10940

  Spacious Two-Family Home in the City of Middletown – Excellent Investment Opportunity Large, solid two-family home located in the City of Middletown, offering strong rental income and outstanding value. This well-maintained property features: Second Floor: 1,338 sq ft – 3 bedrooms, 1 full bath First Floor: 1,248 sq ft – 2 bedrooms, 1 full bath Current rents are $2,100 and $1,800 per month,

  Jonathon Lee KW Hudson Valley Untied

  14 Bonnell St, Middletown, NY 10940
• 

  $285,000

  Sold Nov 24, 2025

  19 Randall Terrace, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,088 Sq Ft
  • Built 1953

  Last Sold Summary

  • 24% Below List Price
  • $136/SF
  • 55 Days On Market

  Current Estimated Value $328,750

  Last Listing Agent Lynelle Alessi KW Hudson Valley Untied

  19 Randall Terrace, Middletown, NY 10940
• 

  Est $501,773

  Not Listed For Sale

  661 Pocatello Rd, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,304 Sq Ft
  • Built 1986

  661 Pocatello Rd, Middletown, NY 10940

  Last Sold Summary

  • 49 Days On Market
• 

  /2

  $299,900

  $20K PRICE DROP Pending

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  580 van Burenville Rd, Middletown, NY 10940

  Welcome to 580 Van Burenville Rd.

  Valerie Jewis Keller Williams Realty

  580 van Burenville Rd, Middletown, NY 10940
• 

  $465,000

  Sold Aug 25, 2025

  1 Lindentree Ln, Middletown, NY 10940

  • 3 Beds
  • 3.5 Baths
  • 1,781 Sq Ft
  • Built 2017

  Last Sold Summary

  • 7% Above List Price
  • $261/SF
  • 35 Days On Market

  Current Estimated Value $480,358

  Last Listing Agent Katheryn DeClerck Howard Hanna Rand Realty

  1 Lindentree Ln, Middletown, NY 10940
• 

  Est $299,275

  Not Listed For Sale

  168 Camp Stadie Rd, Middletown, NY 10940

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1961

  168 Camp Stadie Rd, Middletown, NY 10940

  Last Sold Summary

  • 201 Days On Market
• 

  

  /45

  $400,000

  Pending

  • 8 Beds
  • 3 Baths
  • 2,121 Sq Ft

  29 Columbia Ave, Middletown, NY 10940

  Charming 1923 Traditional – Spacious 8-Bedroom Single Family Home with Timeless Character Step into a rare opportunity to own a beautifully expansive 3-story traditional home built in 1923, offering over 2,100 square feet of versatile living space. Brimming with classic charm and endless potential, this 8-bedroom, 3-bathroom residence is perfect for those seeking room to grow, host, or simply

  Sharon Pehush HomeSmart Homes & Estates

  29 Columbia Ave, Middletown, NY 10940
• 

  $580,000

  Sold Mar 09, 2026

  126 W Main St, Middletown, NY 10940

  • 6 Beds
  • 4 Baths
  • 2,074 Sq Ft
  • Built 1870

  Last Sold Summary

  • 1% Above List Price
  • $280/SF
  • 52 Days On Market

  Current Estimated Value $485,104

  Last Listing Agent Sandra Arnez KW Hudson Valley Untied

  126 W Main St, Middletown, NY 10940
• 

  Est $451,390

  Not Listed For Sale

  15 Milo Dr, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 2,152 Sq Ft
  • Built 1992

  15 Milo Dr, Middletown, NY 10941

  Last Sold Summary

  • 24 Days On Market
• 

  

  /16

  $629,000

  • 4 Beds
  • 3 Baths
  • 2,444 Sq Ft

  744 Mt Hope Rd, Middletown, NY 10940

  Welcome to this stunning new Colonial home, currently under construction and set on approximately 3 beautiful acres in the desirable Town of Wallkill. Offering approximately 2,400 square feet of finished living space, including a finished basement, this spacious home features 4 bedrooms, 3 full bathrooms, and a one-car garage. The inviting open-concept design showcases gleaming hardwood floors

  Anita S. Cristiano HomeSmart Homes & Estates

  744 Mt Hope Rd, Middletown, NY 10940
• 

  $363,500

  Sold Jul 16, 2025

  101 Edinburgh Rd, Middletown, NY 10941

  • 3 Beds
  • 1 Bath
  • 1,236 Sq Ft
  • Built 1971

  Last Sold Summary

  • 2% Below List Price
  • $294/SF
  • 33 Days On Market

  Current Estimated Value $366,307

  Last Listing Agent Maria Sairrino Cronin & Company Real Estate

  101 Edinburgh Rd, Middletown, NY 10941
• 

  Not Listed For Sale

  100 Hillside Dr Unit G2, Middletown, NY 10941

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1987

  100 Hillside Dr Unit G2, Middletown, NY 10941

  Last Sold Summary

  • 25 Days On Market
• 

  

  /37

  $159,000

  Pending

  • Land
  • 14.61 Acres
  • $10,883 per Acre

  Lots 2 / 3 Quail Ridge Rd, Middletown, NY 12455

  Two scenic parcels totaling 14.61 acres with sweeping mountain views offer the perfect canvas for an inspiring Catskills retreat. Ideally situated between the charming towns of Margaretville and Roxbury, this location provides convenient access to grocery stores, art galleries, cafés, and quaint local shops—while still feeling worlds away from the hectic life of more developed areas. An excellent

  James Karpowicz Coldwell Banker Timberland Pro

  Lots 2 / 3 Quail Ridge Rd, Middletown, NY 12455
• 

  $679,000

  Sold Apr 30, 2026

  864 Route 17m, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 2025

  Last Sold Summary

  • $283/SF
  • 32 Days On Market

  Current Estimated Value $672,235

  Last Listing Agent Anita S. Cristiano HomeSmart Homes & Estates

  864 Route 17m, Middletown, NY 10940
• 

  Not Listed For Sale

  100 Hillside Dr Unit A6, Middletown, NY 10941

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1987

  100 Hillside Dr Unit A6, Middletown, NY 10941

  Last Sold Summary

  • 18 Days On Market
• 

  

  /35

  $415,000

  • 3 Beds
  • 1 Bath
  • 1,032 Sq Ft

  80 Beattie Ave, Middletown, NY 10940

  Welcome Home to Comfort, Style & Convenience in the Heart of Middletown! This beautifully renovated two-story Colonial blends timeless charm with modern updates, offering the perfect place to call home. Featuring 3 bedrooms, 1 full bathroom, and thoughtfully designed living spaces throughout, this move-in-ready property has been updated to maximize both functionality and style. From the moment

  Sheyla Falesto Howard Hanna Rand Realty

  80 Beattie Ave, Middletown, NY 10940
• 

  $390,000

  Sold May 18, 2026

  32 Dudley Ln, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,984 Sq Ft
  • Built 1900

  Last Sold Summary

  • 7% Below List Price
  • $197/SF
  • 78 Days On Market

  Current Estimated Value $367,865

  Last Listing Agent Naomi Streicher Q Home Sales

  32 Dudley Ln, Middletown, NY 10940
• 

  Not Listed For Sale

  100 Hillside Dr Unit C1, Middletown, NY 10941

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1987

  100 Hillside Dr Unit C1, Middletown, NY 10941

  Last Sold Summary

  • 19 Days On Market
• 

  

  /17

  $515,000

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

  86 Maples Rd, Middletown, NY 10940

  Beautiful Raised Ranch in Middletown, NY This stunning home features 4 spacious bedrooms and 3 full bathrooms, offering comfort, style, and plenty of space for living and entertaining. The kitchen showcases gorgeous marble countertops and detailed custom cabinetry that truly stand out. The living room boasts vaulted ceilings and a large picture window that fills the space with natural light and

  Delease Jenkins RE/MAX Town & Country

  86 Maples Rd, Middletown, NY 10940
• 

  $510,000

  Sold Jun 08, 2026

  22 Sharon Dr, Middletown, NY 10941

  • 4 Beds
  • 2.5 Baths
  • 2,132 Sq Ft
  • Built 2000

  Last Sold Summary

  • 2% Above List Price
  • $239/SF
  • 85 Days On Market

  Current Estimated Value $499,011

  Last Listing Agent Ammar Iqbal eXp Realty

  22 Sharon Dr, Middletown, NY 10941
• 

  Not Listed For Sale

  100 Hillside Dr Unit B9, Middletown, NY 10941

  • 1 Bed
  • 1 Bath
  • 917 Sq Ft
  • Built 1987

  100 Hillside Dr Unit B9, Middletown, NY 10941

  Last Sold Summary

  • 10 Days On Market
• 

  

  /34

  $399,999

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,756 Sq Ft

  16 Brewster Dr, Middletown, NY 10940

  This beautifully updated home blends modern comfort with thoughtful design, offering a move-in-ready space that feels brand new from top to bottom. Step inside to an open, bright layout featuring fresh finishes, hardwood flooring, and a seamless flow throughout. The upper loft/den area provides the perfect bonus space for a home office, media room, or cozy retreat. A full basement adds even more

  Michelle Gruberger Real Estate Circuit Inc

  16 Brewster Dr, Middletown, NY 10940
• 

  $550,000

  Sold Apr 02, 2026

  6 Wayne Dr, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • Built 1985

  Last Sold Summary

  • 5% Above List Price
  • $327/SF
  • 36 Days On Market

  Current Estimated Value $544,009

  Last Listing Agent Tremaine Selby Weichert Realtors

  6 Wayne Dr, Middletown, NY 10940
• 

  Not Listed For Sale

  100 Hillside Dr Unit G16, Middletown, NY 10941

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1987

  100 Hillside Dr Unit G16, Middletown, NY 10941

  Last Sold Summary

  • 23 Days On Market
• 

  

  /21

  $369,900

  • 4 Beds
  • 1.5 Baths
  • 1,602 Sq Ft

  15 Scotchtown Place, Middletown, NY 10941

  Welcome to this Charming, 4 bedroom 1 1/2 bath Cape style home, offering 1602 sq ft of comfortable living space. This well-laid-out residence features four bedrooms and 1 and 1/2 th bathrooms, perfect for flexible living arrangements. Hardwood floors lie beneath the carpeting in the living room, and bedrooms, ready to be restored to their original beauty. The bright living room features a cozy

  Brian Schofield DiMatteo Realty LLC

  15 Scotchtown Place, Middletown, NY 10941
• 

  $300,000

  Sold Oct 14, 2025

  7 Wilbur Ave, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,922 Sq Ft
  • Built 1892

  Last Sold Summary

  • 20% Below List Price
  • $156/SF
  • 128 Days On Market

  Current Estimated Value $360,277

  Last Listing Agent John Bilancione Nicoli Realty

  7 Wilbur Ave, Middletown, NY 10940
• 

  Est $461,035

  Not Listed For Sale

  12 Acorn Ave, Middletown, NY 10941

  • 4 Beds
  • 3 Baths
  • 1,838 Sq Ft
  • Built 1988

  12 Acorn Ave, Middletown, NY 10941

  Last Sold Summary

  • 22 Days On Market
• 

  

  /32

  $389,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,110 Sq Ft

  671 Route 211 W, Middletown, NY 10940

  Move right into this charming Cape Cod featuring a beautifully renovated kitchen and updated baths, hardwood floors throughout, and 3 bedrooms. The oversized 2-car detached garage offers unfinished loft space ideal for a home office, studio, or workshop. Enjoy the large, level yard with plenty of room for outdoor entertaining. Conveniently located near major highway highways for an easy commute

  Denise DePaola Hudson Premium Realty

  671 Route 211 W, Middletown, NY 10940
• 

  

  /50

  $595,000

  Sold Jul 21, 2025

  1 Wawayanda Place, Middletown, NY 10940

  • 5 Beds
  • 4 Baths
  • 3,890 Sq Ft
  • Built 1948

  Last Sold Summary

  • $153/SF
  • 2 Days On Market

  Current Estimated Value $561,493

  Last Listing Agent Jamie Sittner Find Advisors

  1 Wawayanda Place, Middletown, NY 10940

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