Middletown, NY Homes

• 

  Est $474,239 Not Listed For Sale

  11 Maplewood Dr, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 2,432 Sq Ft
  • Built 1988

  11 Maplewood Dr, Middletown, NY 10940

  Last Sold Summary

  • 3% Above List Price
  • $189/SF
  • 13 Days On Market

  • Last Sold Price $460,000
  • Nov 02, 2024

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
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  /43

  $594,900

  • 3 Beds
  • 2.5 Baths
  • 2,008 Sq Ft

  180 Ridge Dr, Middletown, NY 10940

  180 Ridge Drive is a beautifully maintained 3 bedroom, 2 1/2 bath pool house located in the Town of Mt. Hope. This outstanding property is situated on a quiet country road in the Minisink School District and just a short drive to shopping, fine restaurants and public transportation. This home has everything one could wish for in their forever home; Bamboo hardwood floors, tile in the kitchen and

  Tom Pahucki Keller Williams Realty

  180 Ridge Dr, Middletown, NY 10940
• 

  $400,000 Sold May 30, 2025

  80 Maple Dr, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,852 Sq Ft
  • Built 1965

  Last Sold Summary

  • 23% Above List Price
  • $216/SF
  • 10 Days On Market

  Current Estimated Value $427,166

  Last Listing Agent Richard Baxter Keller Williams Realty

  80 Maple Dr, Middletown, NY 10941
• 

  Est $457,230 Not Listed For Sale

  8 Maureen Dr, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1985

  8 Maureen Dr, Middletown, NY 10940

  Last Sold Summary

  • 4% Above List Price
  • $278/SF
  • 12 Days On Market

  • Last Sold Price $440,000
  • Mar 19, 2024

  Last Listing Agent Sharon Pehush HomeSmart Homes & Estates
• 

  

  

  /50

  $939,000 Coming Soon

  • 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
• 

  $620,000 Sold Oct 27, 2025

  58 White Bridge Rd, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 3,328 Sq Ft
  • Built 1992

  Last Sold Summary

  • 2% Below List Price
  • $186/SF
  • 21 Days On Market

  Current Estimated Value $635,282

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  58 White Bridge Rd, Middletown, NY 10940
• 

  Est $424,612 Not Listed For Sale

  35 Roger Ave, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,132 Sq Ft
  • Built 1983

  35 Roger Ave, Middletown, NY 10940

  Last Sold Summary

  • 15% Above List Price
  • $327/SF
  • 33 Days On Market

  • Last Sold Price $370,000
  • Jun 08, 2023

  Last Listing Agent John Biasi Howard Hanna Rand Realty
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  /37

  $199,990 Pending

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  238 Concord Ln, Middletown, NY 10940

  Welcome to 238 Concord Lane, a beautifully refreshed home in the heart of Middletown that is truly move-in ready, featuring fresh paint throughout, brand new flooring, and modern lighting that creates a bright, clean, and inviting atmosphere from the moment you step inside; ideally located just minutes from Middletown’s shops, restaurants, and everyday conveniences, this home offers the perfect

  Andi Berisha BHHS Hudson Valley Properties

  238 Concord Ln, Middletown, NY 10940
• 

  $605,000 Sold Sep 19, 2025

  344 Ingrassia Rd, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,410 Sq Ft
  • Built 2006

  Last Sold Summary

  • 3% Below List Price
  • $251/SF
  • 71 Days On Market

  Current Estimated Value $613,316

  Last Listing Agent Travis Thompson Keller Williams Hudson Valley

  344 Ingrassia Rd, Middletown, NY 10940
• 

  Est $471,986 Not Listed For Sale

  80 Maureen Dr, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1988

  80 Maureen Dr, Middletown, NY 10940

  Last Sold Summary

  • 11% Above List Price
  • $270/SF
  • 26 Days On Market

  • Last Sold Price $427,000
  • Dec 13, 2023

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  

  /46

  $564,900

  • 4 Beds
  • 2.5 Baths
  • 2,344 Sq Ft

  1 Hulse St, Middletown, NY 10940

  "NEW CONSTRUCTION!" Stunning corner-lot home in a calm suburban setting with beautiful mountain views — offering space, upgrades, and thoughtful design throughout. This impressive property offers approximately 2,344 sq ft of living space and features 9-ft ceilings on the main level and 8-ft ceilings upstairs, enhancing the open and airy layout. The upgraded 400+ sq ft kitchen is a true highlight,

  Chaim Friedman MS Realty Group USA, Inc

  1 Hulse St, Middletown, NY 10940
• 

  $425,000 Sold Aug 11, 2025

  44 Karen Joy Dr, Middletown, NY 10940

  • 4 Beds
  • 1.5 Baths
  • 2,706 Sq Ft
  • Built 1977

  Last Sold Summary

  • $157/SF
  • 97 Days On Market

  Current Estimated Value $449,166

  Last Listing Agent Frank Muccari Cronin & Company Real Estate

  44 Karen Joy Dr, Middletown, NY 10940
• 

  Est $422,328 Not Listed For Sale

  16 Roger Ave, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,132 Sq Ft
  • Built 1983

  16 Roger Ave, Middletown, NY 10940

  Last Sold Summary

  • 8% Above List Price
  • $345/SF
  • 21 Days On Market

  • Last Sold Price $390,000
  • Sep 08, 2023

  Last Listing Agent Alyssa Scancarello Howard Hanna Rand Realty
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  /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 Keller Williams Hudson Valley

  14 Bonnell St, Middletown, NY 10940
• 

  $157,200 Sold Dec 05, 2025

  10 Hoffman St, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1920

  Last Sold Summary

  • 17% Below List Price
  • $131/SF
  • 70 Days On Market

  Current Estimated Value $164,199

  Last Listing Agent Jamarr Zellner REALHome Services & Solutions

  10 Hoffman St, Middletown, NY 10940
• 

  Est $455,254 Not Listed For Sale

  26 Robinn Dr, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,532 Sq Ft
  • Built 1978

  26 Robinn Dr, Middletown, NY 10940

  Last Sold Summary

  • 10% Above List Price
  • $271/SF
  • 12 Days On Market

  • Last Sold Price $415,001
  • Oct 12, 2023

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  /2

  $299,900 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
• 

  $550,000 Sold Mar 02, 2026

  21 Cyprus Dr, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,868 Sq Ft
  • Built 2016

  Last Sold Summary

  • $294/SF
  • 38 Days On Market

  Current Estimated Value $548,144

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  21 Cyprus Dr, Middletown, NY 10940
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  Est $440,659 Not Listed For Sale

  686 Pocatello Rd, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,684 Sq Ft
  • Built 1980

  686 Pocatello Rd, Middletown, NY 10940

  Last Sold Summary

  • 19% Above List Price
  • $220/SF
  • 14 Days On Market

  • Last Sold Price $370,800
  • Jun 02, 2023

  Last Listing Agent Annie Hansen Howard Hanna Rand Realty
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  /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
• 

  $430,000 Sold May 31, 2025

  49 Bedford Ave, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,636 Sq Ft
  • Built 1950

  Last Sold Summary

  • $263/SF
  • 23 Days On Market

  Current Estimated Value $439,353

  Last Listing Agent John Biasi Howard Hanna Rand Realty

  49 Bedford Ave, Middletown, NY 10940
• 

  Est $357,844 Not Listed For Sale

  50 Millsburg Rd, Middletown, NY 10940

  • 4 Beds
  • 1.5 Baths
  • 1,388 Sq Ft
  • Built 1920

  50 Millsburg Rd, Middletown, NY 10940

  Last Sold Summary

  • 30% Above List Price
  • $198/SF
  • 32 Days On Market

  • Last Sold Price $275,000
  • Dec 21, 2023

  Last Listing Agent Amanda Brehm Keller Williams Hudson Valley
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  /37

  $159,000 Under Contract

  • 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
• 

  $450,000 Sold Dec 19, 2025

  6 Tice Ln, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 2,070 Sq Ft
  • Built 1986

  Last Sold Summary

  • $217/SF
  • 43 Days On Market

  Current Estimated Value $461,683

  Last Listing Agent John Olivero Keller Williams Realty

  6 Tice Ln, Middletown, NY 10941
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  Est $377,860 Not Listed For Sale

  14 S Centerville Rd, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft
  • Built 1824

  14 S Centerville Rd, Middletown, NY 10940

  Last Sold Summary

  • 16% Above List Price
  • $227/SF
  • 77 Days On Market

  • Last Sold Price $325,000
  • Sep 25, 2023

  Last Listing Agent Ronald Garafalo John J Lease REALTORS Inc
• 

  

  /34

  $399,999

  • 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
• 

  $402,000 Sold Sep 12, 2025

  19 Morningside Dr, Middletown, NY 10941

  • 4 Beds
  • 1.5 Baths
  • 1,984 Sq Ft
  • Built 1971

  Last Sold Summary

  • 9% Above List Price
  • $203/SF
  • 15 Days On Market

  Current Estimated Value $413,730

  Last Listing Agent Paul Halpern Hudson Valley Griffith

  19 Morningside Dr, Middletown, NY 10941
• 

  Est $432,491 Not Listed For Sale

  2041 Route 6, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft
  • Built 1997

  2041 Route 6, Middletown, NY 10940

  Last Sold Summary

  • 6% Above List Price
  • $313/SF
  • 76 Days On Market

  • Last Sold Price $407,000
  • Sep 20, 2024

  Last Listing Agent Dean Diltz Keller Williams Realty
• 

  

  /22

  $409,500

  • 2 Beds
  • 2.5 Baths
  • 1,337 Sq Ft

  19 Putters Way Unit 9, Middletown, NY 10940

  Welcome to this fully updated, move-ready condo in the desirable Walkill community. This splendid duplex has been luxuriously upgraded with modern paint tones and the latest finishes. Bright and sunny rooms with updated lighting throughout. The kitchen boasts sleek, brand-new appliances and classic wood cabinetry. The bathrooms have been meticulously maintained. Cathedral ceilings in both

  Abraham Lefkowitz Access Realty Team Inc

  19 Putters Way Unit 9, Middletown, NY 10940
• 

  $195,000 Sold Jan 30, 2026

  21 Lake Claire Dr, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 990 Sq Ft
  • Built 1955

  Last Sold Summary

  • 22% Below List Price
  • $197/SF
  • 142 Days On Market

  Current Estimated Value $215,185

  Last Listing Agent Nelson Dominguez eXp Realty

  21 Lake Claire Dr, Middletown, NY 10940
• 

  Est $579,823 Not Listed For Sale

  128 Jogee Rd, Middletown, NY 10940

  • 3 Beds
  • 3 Baths
  • 1,956 Sq Ft
  • Built 1987

  128 Jogee Rd, Middletown, NY 10940

  Last Sold Summary

  • 4% Above List Price
  • $284/SF
  • 81 Days On Market

  • Last Sold Price $555,000
  • Mar 21, 2025

  Last Listing Agent April Lazier Realty Executives Exceptional
• 

  

  /12

  $210,000

  • 3 Beds
  • 1.5 Baths
  • 1,320 Sq Ft

  8 Grant St, Middletown, NY 10940

  Here's the opportunity investors have been waiting for. This two-story colonial offers the right buyer a full-renovation canvas with real upside. Generous room sizes, hardwood floors on the upper level, a covered front porch, and an oversized barn/garage outbuilding in the rear — features that support strong ARV whether you're flipping or holding for rental income. The home needs a complete

  Igor Krasnoperov Rising Star Realty

  8 Grant St, Middletown, NY 10940
• 

  $478,500 Sold Nov 12, 2025

  138 Reinhardt Rd, Middletown, NY 10940

  • 3 Beds
  • 3 Baths
  • 2,542 Sq Ft
  • Built 1969

  Last Sold Summary

  • 2% Below List Price
  • $188/SF
  • 65 Days On Market

  Current Estimated Value $633,755

  Last Listing Agent Lynelle Alessi Keller Williams Hudson Valley

  138 Reinhardt Rd, Middletown, NY 10940
• 

  Est $409,278 Not Listed For Sale

  210 S Centerville Rd, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft
  • Built 1965

  210 S Centerville Rd, Middletown, NY 10940

  Last Sold Summary

  • $363/SF
  • 14 Days On Market

  • Last Sold Price $410,000
  • Dec 11, 2024

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  

  /27

  $199,000

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  326 Concord Ln, Middletown, NY 10940

  Buttonwood Hills Condominiums now offers a 2 bedroom/2 bath unit for your purchase & to call home! A ground level end unit with open floor from living room to dining room with sliders that lead to a seating area where you can enjoy the outdoors. Beautiful kitchen with stainless steel appliances & plenty of cabinet space. Spacious bedrooms, one with a Suite with double closets and a private full

  Sandra Arnez Keller Williams Hudson Valley

  326 Concord Ln, Middletown, NY 10940
• 

  $380,000 Sold May 29, 2025

  25 Meyer Rd, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,335 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Above List Price
  • $285/SF
  • 113 Days On Market

  Current Estimated Value $390,752

  Last Listing Agent Leon Klein Keller Williams Hudson Valley

  25 Meyer Rd, Middletown, NY 10940
• 

  Est $749,784 Not Listed For Sale

  220 Mt Orange Rd, Middletown, NY 10940

  • 3 Beds
  • 3.5 Baths
  • 3,456 Sq Ft
  • Built 2002

  220 Mt Orange Rd, Middletown, NY 10940

  Last Sold Summary

  • $217/SF
  • 63 Days On Market

  • Last Sold Price $749,000
  • Oct 02, 2024

  Last Listing Agent Barbara Allen HomeSmart Homes & Estates
• 

  

  /12

  $65,000

  • Land
  • 7,875 Sq Ft
  • $359,513 per Acre

  538 E Main St, Middletown, NY 10940

  Residential land avaiable on East Main Street, close to the Crystal Medical center, close to NYS HWY 17, close to the Galleria Mall, close to the new Resorts and Casino about 30 milles away, close to the Poconos, come built you new home here.

  Frank Rivera Hudson Valley Home Connection

  538 E Main St, Middletown, NY 10940
• 

  $485,000 Sold Oct 23, 2025

  38 Woodside Knolls Dr, Middletown, NY 10940

  • 3 Beds
  • 3.5 Baths
  • 1,899 Sq Ft
  • Built 2008

  Last Sold Summary

  • 1% Above List Price
  • $255/SF
  • 42 Days On Market

  Current Estimated Value $496,077

  Last Listing Agent Naomi Streicher Q Home Sales

  38 Woodside Knolls Dr, Middletown, NY 10940
• 

  Est $576,740 Not Listed For Sale

  809 Kirbytown Rd, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,043 Sq Ft
  • Built 2001

  809 Kirbytown Rd, Middletown, NY 10940

  Last Sold Summary

  • 10% Above List Price
  • $257/SF
  • 35 Days On Market

  • Last Sold Price $525,000
  • Aug 22, 2023

  Last Listing Agent Meaghan Michella Cronin & Company Real Estate

Showing Results 361 - 400, Page 10 of 18