Middletown, NY Homes

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  /50

  $899,000

  $40K PRICE DROP Pending

  • 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

  Michelle Genatempo Howard Hanna Rand Realty

  114 Last Rd, Middletown, NY 10941
• 

  $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 $515,877

  Last Listing Agent Joseph Rubeo KW Hudson Valley United

  3 Ben Lomond Dr, Middletown, NY 10941
• 

  Est $476,292

  Not Listed For Sale

  34 Roger Ave, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1983

  34 Roger Ave, Middletown, NY 10940

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  

  

  /31

  $849,900

  • 4 Beds
  • 2.5 Baths
  • 3,217 Sq Ft

  112 Elise Dr, Middletown, NY 10941

  Welcome to Scotchtown Estates, where this stunning, three -year-young Center Hall Colonial combines the pristine feel of new construction with thoughtful upgrades, beautiful landscaping, and premium amenities already in place. Originally showcased as one of the neighborhood’s model homes, this exceptional residence offers approximately 3,200 square feet of beautifully designed living space, with

  Tammy Scotto Keller Williams Realty

  112 Elise Dr, Middletown, NY 10941
• 

  $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 $440,330

  Last Listing Agent Gail Rachlin KW Hudson Valley United

  35 East Ave, Middletown, NY 10940
• 

  Est $453,398

  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

  • 12 Days On Market

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
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  /12

  $239,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,316 Sq Ft

  26 Willow Place, Middletown, NY 10940

  Calling all contractors, investors, and homeowners with a vision! Bring your ideas and your toolbox to this 3-bedroom, 1.5-bath split-level home situated on a desirable corner lot within the Enlarged City School District of Middletown. Offering great bones and endless potential, this property is ready for its next owner to restore, renovate, and make it their own.Inside, you'll find a

  Maria Sairrino Cronin & Company Real Estate

  26 Willow Place, Middletown, NY 10940
• 

  $347,000

  Sold Jul 20, 2026

  42 Mayer Dr, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,730 Sq Ft
  • Built 1996

  Last Sold Summary

  • 5% Above List Price
  • $201/SF
  • 85 Days On Market

  Current Estimated Value $401,431

  Last Listing Agent Dominick Tufano RE/MAX Benchmark Realty Group

  42 Mayer Dr, Middletown, NY 10940
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  Est $348,089

  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

  • 32 Days On Market

  Last Listing Agent Amanda Brehm KW Hudson Valley United
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  /32

  $714,000

  $26K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,733 Sq Ft

  210 Howells Turnpike, Middletown, NY 10940

  Nestled on 2.5 peaceful acres, this colonial-style home has been lovingly cared for by the same owner since it was built in 2006. The dramatic cathedral ceiling foyer welcomes you with a sense of grandeur, opening to a spacious interior filled with natural light. Hardwood floors flow throughout, enhanced by a refreshed staircase with updated balusters and designer lighting.The custom kitchen

  Cecilia Lewis Century 21 Elite Realty

  210 Howells Turnpike, Middletown, NY 10940
• 

  $515,000

  Sold Aug 07, 2026

  29 Beth Dr, Middletown, NY 10941

  • 4 Beds
  • 2 Baths
  • 1,716 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Below List Price
  • $300/SF
  • 18 Days On Market

  Current Estimated Value $511,917

  Last Listing Agent Derek Greene Greene Realty Group

  29 Beth Dr, Middletown, NY 10941
• 

  Est $388,420

  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

  • 77 Days On Market

  Last Listing Agent Ronald Garafalo Hudson Premium Realty
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  /17

  $609,000

  $20K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,400 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 2,600 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
• 

  $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 $326,051

  Last Listing Agent Jonathon Lee KW Hudson Valley United

  24 Kent Ct, Middletown, NY 10940
• 

  Est $451,783

  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

  • 76 Days On Market

  Last Listing Agent Dean Diltz Keller Williams Realty
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  /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
• 

  $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 $292,409

  Last Listing Agent Jackie Siracuse Absolute Real Estate of NY Inc

  63 Pierson Hill Rd, Middletown, NY 10940
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  Est $360,046

  Not Listed For Sale

  2027 Route 6, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,047 Sq Ft
  • Built 1957

  2027 Route 6, Middletown, NY 10940

  Last Sold Summary

  • 50 Days On Market

  Last Listing Agent Bente Brown Hudson Premium Realty
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  /49

  $489,999

  Open Sat 12PM - 2PM $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  58 Cobblestone Ln, Middletown, NY 10940

  Welcome to this beautifully maintained 2,500 sq. ft. townhouse in the desirable Woodside Knolls community. This spacious home offers 3 bedrooms, each featuring a walk-in closet, and 2.5 bathrooms. The open-concept floor plan seamlessly connects the living area and modern kitchen, creating an inviting space for everyday living and entertaining.Additional features include a two-car attached

  Doreen Crowther Howard Hanna Rand Realty

  58 Cobblestone Ln, 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 $434,462

  Last Listing Agent Sandra Arnez KW Hudson Valley United

  126 W Main St, Middletown, NY 10940
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  Est $593,513

  Not Listed For Sale

  293 S Centerville Rd, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,284 Sq Ft
  • Built 1998

  293 S Centerville Rd, Middletown, NY 10940

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Rachel Hunt Realty Promotions Inc
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  /35

  $375,000

  $40K PRICE DROP

  • 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

  Sheyla Falesto Howard Hanna Rand Realty

  80 Beattie Ave, Middletown, NY 10940
• 

  $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 $676,767

  Last Listing Agent Anita S. Cristiano HomeSmart Homes & Estates

  864 Route 17m, Middletown, NY 10940
• 

  Est $581,170

  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

  • 81 Days On Market

  Last Listing Agent April Lazier Realty Executives Exceptional
• 

  

  /50

  $419,900

  $10K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  21 Harrison St, Middletown, NY 10940

  Welcome to this well-maintained 4-bedroom, 1.5-bath Victorian home offering a functional layout with numerous updates throughout. A covered front porch welcomes you inside, where the main level features a spacious living room, formal dining room, comfortable family room, updated kitchen, and a convenient half bath. Upstairs, you'll find four bedrooms and a full bathroom, providing a practical

  Jie Liu KW Hudson Valley United

  21 Harrison St, 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 $390,875

  Last Listing Agent Naomi Streicher Q Home Sales

  32 Dudley Ln, Middletown, NY 10940
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  Est $426,375

  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

  • 14 Days On Market

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  

  /5

  $335,000

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft

  41 Clinton St, Middletown, NY 10940

  3 Bedroom 1 bath ranch in Middletown! Close to Commuter Highways, Trains & ShoppingSOLD AS-IS SIGHT UNSEEN! CASH ONLY! DO NOT DISTURB OCCUPANTS!!

  Ernie Acampora River Realty Services, Inc.

  41 Clinton St, 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 $511,891

  Last Listing Agent Ammar Iqbal eXp Realty

  22 Sharon Dr, Middletown, NY 10941
• 

  Est $653,970

  Not Listed For Sale

  223 Mt Orange Rd, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,376 Sq Ft
  • Built 1992

  223 Mt Orange Rd, Middletown, NY 10940

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  

  /22

  $399,000

  $26K PRICE DROP

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

  19 Putters Way Unit 9, Middletown, NY 10940

  Welcome to a move-ready condo in the desirable Walkill community. This splendid duplex has been 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 bedrooms lend a dramatic vibe for a

  Abraham Lefkowitz Access Realty Team Inc

  19 Putters Way Unit 9, Middletown, NY 10940
• 

  $400,000

  Sold Jul 13, 2026

  41 Monhagen Ave Unit 39, Middletown, NY 10940

  • 5 Beds
  • 4 Baths
  • Built 1910

  Last Sold Summary

  • 2% Below List Price
  • 90 Days On Market

  Last Listing Agent Zhiheng Tang KW Hudson Valley United

  41 Monhagen Ave Unit 39, Middletown, NY 10940
• 

  Est $796,029

  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

  • 63 Days On Market

  Last Listing Agent Barbara Allen HomeSmart Homes & Estates
• 

  

  /23

  $399,999

  Pending

  • 5 Beds
  • 2 Baths
  • 1,664 Sq Ft

  341 Highland Ave Extension, Middletown, NY 10940

  Welcome to 341 Highland Ave Ext, a bright and airy 4-bedroom, 2-bath split-level home conveniently situated in the heart of town. An inviting open floor plan creates effortless flow throughout the main living spaces, offering comfort, style, and plenty of natural light. Enjoy a level, fenced-in backyard—ideal for outdoor gatherings or peaceful relaxation. With local eateries, shopping, and daily

  Valerie Jewis Keller Williams Realty

  341 Highland Ave Extension, Middletown, NY 10940
• 

  $240,000

  Sold Aug 19, 2026

  34 Poplar Ln, Middletown, NY 10941

  • 2 Beds
  • 1.5 Baths
  • 1,240 Sq Ft
  • Built 1974

  Last Sold Summary

  • 4% Below List Price
  • $194/SF
  • 86 Days On Market

  Current Estimated Value $257,202

  Last Listing Agent John Olivero Keller Williams Realty

  34 Poplar Ln, Middletown, NY 10941
• 

  Est $621,619

  Not Listed For Sale

  388 Mt Orange Rd, Middletown, NY 10940

  • 4 Beds
  • 3.5 Baths
  • 2,824 Sq Ft
  • Built 1993

  388 Mt Orange Rd, Middletown, NY 10940

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  

  /12

  $210,000

  Pending Pre-Foreclosure

  • 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
• 

  $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 $548,482

  Last Listing Agent Tremaine Selby Weichert Realtors

  6 Wayne Dr, Middletown, NY 10940
• 

  Est $504,319

  Not Listed For Sale

  450 Mt Orange Rd, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 2008

  450 Mt Orange Rd, Middletown, NY 10940

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Katrina Roloson Keller Williams Realty
• 

  

  /7

  $849,999

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,862 Sq Ft

  241 Midland Lake Rd, Middletown, NY 10941

  NEW CONSTRUCTION! Set against a peaceful backdrop, this Colonial pairs timeless curb appeal with a practical, beautifully planned interior. This home offers a modern living space with four bedrooms, two and a half baths, a dedicated den, a generous kitchen with island, formal dining and living rooms, second-floor laundry, and a spacious bonus room that doubles as the fourth bedroom.A

  Hilary Ryan Goldman Howard Hanna Rand Realty

  241 Midland Lake Rd, Middletown, NY 10941

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