Middletown, NY Homes

• 

  $325,000

  Sold Apr 28, 2026

  46 Silo Ln, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,452 Sq Ft
  • Built 1973

  Last Sold Summary

  • $224/SF
  • 20 Days On Market

  Current Estimated Value $325,996

  Last Listing Agent Jason Dillon eXp Realty

  46 Silo Ln, Middletown, NY 10940
• 

  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
• 

  

  

  /49

  $589,900

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,192 Sq Ft

  311 New Vernon Rd, Middletown, NY 10940

  Nestled well off the road amid mature landscaping and expansive lawn, this custom Colonial offers a rare combination of privacy, space, and pride of ownership. Built and meticulously maintained by its original owners, the home reflects years of thoughtful updates and careful stewardship. Inside, hardwood floors extend throughout the home, creating warmth and continuity from room to room. Custom

  Patricia Sassi RE/MAX Benchmark Realty Group

  311 New Vernon Rd, Middletown, NY 10940
• 

  $380,000

  Sold Feb 10, 2026

  7 Manhattan Ave, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,550 Sq Ft
  • Built 1958

  Last Sold Summary

  • 3% Above List Price
  • $245/SF
  • 46 Days On Market

  Current Estimated Value $377,980

  Last Listing Agent Darnell Williams R New York

  7 Manhattan Ave, Middletown, NY 10940
• 

  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
• 

  

  /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
• 

  $360,000

  Sold Nov 07, 2025

  55 Prince St, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,537 Sq Ft
  • Built 1893

  Last Sold Summary

  • 16% Above List Price
  • $234/SF
  • 36 Days On Market

  Current Estimated Value $357,410

  Last Listing Agent Andi Berisha BHHS Hudson Valley Properties

  55 Prince St, 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
• 

  

  /32

  $740,000

  • 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 is

  Cecilia Lewis Century 21 Elite Realty

  210 Howells Turnpike, Middletown, NY 10940
• 

  $155,000

  Sold Sep 18, 2025

  268 Concord Ln, Middletown, NY 10940

  • 1 Bed
  • 1 Bath
  • 735 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $211/SF
  • 63 Days On Market

  Current Estimated Value $158,727

  Last Listing Agent Chris Cardinal Keller Williams Realty

  268 Concord Ln, Middletown, NY 10940
• 

  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
• 

  

  /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
• 

  $370,000

  Sold Aug 26, 2025

  34 Pine Ct, Middletown, NY 10941

  • 4 Beds
  • 2.5 Baths
  • 2,358 Sq Ft
  • Built 1971

  Last Sold Summary

  • 1% Below List Price
  • $157/SF
  • 6 Days On Market

  Current Estimated Value $412,998

  Last Listing Agent Frank Tangredi Frank Tangredi Realty Company

  34 Pine Ct, Middletown, NY 10941
• 

  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
• 

  

  /17

  $629,000

  • 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
• 

  $525,000

  Sold Jun 18, 2026

  10 Cyprus Dr, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Built 2014

  Last Sold Summary

  • 7% Above List Price
  • $326/SF
  • 29 Days On Market

  Current Estimated Value $509,400

  Last Listing Agent Hilary Ryan Goldman Howard Hanna Rand Realty

  10 Cyprus Dr, 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
• 

  

  /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
• 

  $480,000

  Sold Dec 05, 2025

  95 Rolling Meadows Rd, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,055 Sq Ft
  • Built 1979

  Last Sold Summary

  • 5% Above List Price
  • $234/SF
  • 14 Days On Market

  Current Estimated Value $487,876

  Last Listing Agent Kevin Grier KW Hudson Valley United

  95 Rolling Meadows Rd, Middletown, NY 10940
• 

  Est $587,410

  Not Listed For Sale

  58 Burnt Corners Rd, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,470 Sq Ft
  • Built 1992

  58 Burnt Corners Rd, Middletown, NY 10940

  Last Sold Summary

  • 202 Days On Market

  Last Listing Agent Sandra Arnez KW Hudson Valley United
• 

  

  /49

  $495,000

  • 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 garage

  Doreen Crowther Howard Hanna Rand Realty

  58 Cobblestone Ln, Middletown, NY 10940
• 

  $338,500

  Sold Nov 26, 2025

  12 Columbine Ct, Middletown, NY 10940

  • 4 Beds
  • 1.5 Baths
  • 1,408 Sq Ft
  • Built 1979

  Last Sold Summary

  • 1% Above List Price
  • $240/SF
  • 33 Days On Market

  Current Estimated Value $336,230

  Last Listing Agent Christina Gilligan HomeSmart Homes & Estates

  12 Columbine Ct, Middletown, NY 10940
• 

  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
• 

  

  /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
• 

  $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 $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
• 

  

  /17

  $515,000

  Pending

  • 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
• 

  $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 $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
• 

  

  /21

  $369,900

  Pending

  • 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
• 

  $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
• 

  Est $597,538

  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

  • 35 Days On Market

  Last Listing Agent Meaghan Michella Cronin & Company Real Estate
• 

  

  /31

  $449,900

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,624 Sq Ft

  28 Wilson St, Middletown, NY 10940

  Tucked into one of Middletown's most well-kept and welcoming neighborhoods, this thoughtfully maintained raised ranch delivers comfort, updates, and value in equal measure — the kind of home that checks the boxes you didn't even know you had. At the heart of the home is a beautifully renovated kitchen — open concept with full sightlines into the dining area and family room, ample cabinetry, and a

  Geoffrey Green BHG Real Estate Green Team

  28 Wilson St, 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 $660,778

  Not Listed For Sale

  658 Mt Orange Rd, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,482 Sq Ft
  • Built 2005

  658 Mt Orange Rd, Middletown, NY 10940

  Last Sold Summary

  • 100 Days On Market

  Last Listing Agent Christina Biagini Weichert Realtors
• 

  

  /22

  $399,000

  Open Sun 1PM - 3PM $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
• 

  $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 $290,572

  Last Listing Agent Jackie Siracuse Absolute Real Estate of NY Inc

  63 Pierson Hill Rd, Middletown, NY 10940
• 

  Est $852,858

  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

  Last Listing Agent Kewin Garabito eXp Realty
• 

  

  /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
• 

  $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 $484,117

  Last Listing Agent Katheryn DeClerck Howard Hanna Rand Realty

  1 Lindentree Ln, Middletown, NY 10940

Showing Results 401 - 440, Page 11 of 18