Middletown, NY Homes

• 

  $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

  Last Listing Agent Naomi Streicher Q Home Sales

  38 Woodside Knolls Dr, Middletown, NY 10940
• 

  Not Listed For Sale

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

  100 Hillside Dr Unit C1, Middletown, NY 10941

  100 Hillside Dr Unit C1, Middletown, NY 10941
• 

  

  /2

  $60,000 Pending

  • Land
  • 0.11 Acre
  • $522,648 per Acre

  14 W Conkling Ave, Middletown, NY 10940

  Welcome to 14 W Conklin Ave! This rare opportunity allows you to build your dream home on a vacant lot in the heart of Middletown. Nestled on a quiet street, the lot offers a serene atmosphere while being within walking distance to Orange County Community College. The surrounding area boasts numerous parks and playgrounds, providing a great outdoor experience. The property is conveniently located

  Travis Thompson Keller Williams Hudson Valley

  14 W Conkling Ave, Middletown, NY 10940
• 

  $629,900 Sold Feb 07, 2025

  44 Pine Grove Rd, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,378 Sq Ft
  • Built 2025

  Last Sold Summary

  • 13% Above List Price
  • $265/SF
  • 140 Days On Market

  Last Listing Agent Chris Ogden Realty Promotions Inc

  44 Pine Grove Rd, Middletown, NY 10940
• 

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 917 Sq Ft

  100 Hillside Dr Unit B9, Middletown, NY 10941

  100 Hillside Dr Unit B9, Middletown, NY 10941
• 

  

  /33

  $429,999

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

  13 Forest Ave, Middletown, NY 10940

  Welcome to 13 Forest Ave, a spacious and versatile home located in the heart of Middletown, just minutes from the Touro College of Osteopathic Medicine campus and medical facilities. This charming property offers approximately 1,748 sq ft of living space, featuring 3–4 bedrooms and 2 full bathrooms, making it an excellent fit for households seeking flexibility or additional private living areas.

  Pete Wolven Hudson Valley Home Connection

  13 Forest Ave, Middletown, NY 10940
• 

  $265,000 Sold Apr 03, 2025

  43 Woodlake Dr Unit 43, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,460 Sq Ft
  • Built 1999

  Last Sold Summary

  • $182/SF
  • 25 Days On Market

  Current Estimated Value $291,588

  Last Listing Agent Gary Myers eXp Realty

  43 Woodlake Dr Unit 43, Middletown, NY 10940
• 

  Not Listed For Sale

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

  100 Hillside Dr Unit G16, Middletown, NY 10941

  100 Hillside Dr Unit G16, Middletown, NY 10941
• 

  

  /6

  $75,000 Pending

  • 2 Beds
  • 1 Bath
  • 624 Sq Ft

  3 Birch St, Middletown, NY 10940

  Single Family Seasonal Cottage in Middletown! Here's the opportunity to create your perfect getaway at this cozy 2 story cabin set on a 50 x 100 ft lot in the heart of Middletown. The attic portion was being converted into living space, designed to accommodate three bedrooms and one bathroom. This cabin holds endless potential and offers buyers a chance to design a custom retreat. Property

  Thomas Horodecki Capri Jet Realty Corp

  3 Birch St, Middletown, NY 10940
• 

  $507,000 Sold Mar 25, 2025

  7 Dogwood Dr, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft
  • Built 2002

  Last Sold Summary

  • 4% Above List Price
  • $240/SF
  • 26 Days On Market

  Current Estimated Value $517,609

  Last Listing Agent Naomi Streicher Q Home Sales

  7 Dogwood Dr, Middletown, NY 10940
• 

  Est $491,197 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,034 Sq Ft

  21 Shagbark St, Middletown, NY 10941

  21 Shagbark St, Middletown, NY 10941
• 

  

  /23

  $185,000 Pending

  • 1 Bed
  • 1 Bath
  • 830 Sq Ft

  59 Sycamore Dr, Middletown, NY 10940

  NEW TO THE MARKET! -- DISCOVER EXCEPTIONAL VALUE at 59 Sycamore Dr, Middletown, NY. This 1-br condo in Clemson Park offers the perfect opportunity for anyone seeking ownership and an elevated living experience without the high price tag. We're priced to move quickly and don't expect this one to last long! Step inside and be greeted by an open, light-filled layout and living area that flows

  Alexander Panet Real Broker NY LLC

  59 Sycamore Dr, Middletown, NY 10940
• 

  $575,000 Sold Jul 03, 2025

  5 Robert Burns Ct, Middletown, NY 10941

  • 6 Beds
  • 2 Baths
  • 2,448 Sq Ft
  • Built 1966

  Last Sold Summary

  • 4% Below List Price
  • $235/SF
  • 71 Days On Market

  Current Estimated Value $579,774

  Last Listing Agent Maria Sairrino Cronin & Company Real Estate

  5 Robert Burns Ct, Middletown, NY 10941
• 

  Est $440,812 Not Listed For Sale

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

  12 Acorn Ave, Middletown, NY 10941

  12 Acorn Ave, Middletown, NY 10941
• 

  

  /15

  $264,999

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

  11 Jordan Ln, Middletown, NY 10940

  Great opportunity for investors for fix and flip.Minimal work needed to make it presentable.Town house located in a beautiful neighborhood.

  Siju John Kerala Realty, LLC

  11 Jordan Ln, Middletown, NY 10940
• 

  $218,000 Sold Feb 13, 2025

  12 Jimal Dr, Middletown, NY 10940

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

  Last Sold Summary

  • 1% Below List Price
  • $244/SF
  • 28 Days On Market

  Current Estimated Value $226,664

  Last Listing Agent Jonathon Lee Keller Williams Hudson Valley

  12 Jimal Dr, Middletown, NY 10940
• 

  Est $506,834 Not Listed For Sale

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

  28 Shagbark St, Middletown, NY 10941

  28 Shagbark St, Middletown, NY 10941
• 

  

  /16

  $599,900 Pending

  • 4 Beds
  • 3 Baths
  • 2,445 Sq Ft

  718 Mount Hope Rd, Middletown, NY 10940

  Let's welcome the Fall of 2025 with this beautiful and spacious contemporary home sitting on 4 acres lot. The upper level is featuring an open layout with gleaming oak hardwood floors throughout a massive living room with a very high ceiling & built in electric fireplace to a formal dining area and a very wide and spacious gorgeous kitchen with a great size island, quartz countertops & stainless

  Anita S. Cristiano HomeSmart Homes & Estates

  718 Mount Hope Rd, Middletown, NY 10940
• 

  $402,000 Sold Jul 02, 2025

  34 Walnut Ln, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1991

  Last Sold Summary

  • 1% Above List Price
  • $349/SF
  • 26 Days On Market

  Current Estimated Value $402,266

  Last Listing Agent Laurel Lustgarten Howard Hanna Rand Realty

  34 Walnut Ln, Middletown, NY 10940
• 

  Est $643,948 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,955 Sq Ft

  29 Placid Ave, Middletown, NY 10941

  29 Placid Ave, Middletown, NY 10941
• 

  

  /23

  $135,000

  • Land
  • 6.5 Acres
  • $20,769 per Acre

  437 Union School Rd, Middletown, NY 10941

  Nice 6.5 acre level lot with 370' of frontage in a desirable location and in VC schools. Seller has made the following improvements to the property; 200' of 6 inch ditch pipe with fabric. Trench filled with 3/4 inch stone. 10 tri-axle loads of compactable fill (rca) in front and rear of dwelling, 80 tri-axle loads of fill to regrade rear of property to shed water, Engineers have told the seller

  Ian Pinckney Curasi Realty, Inc.

  437 Union School 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

  Last Listing Agent Andi Berisha BHHS Hudson Valley Properties

  55 Prince St, Middletown, NY 10940
• 

  Est $333,780 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft

  6 Buckingham Mews, Middletown, NY 10940

  6 Buckingham Mews, Middletown, NY 10940
• 

  

  /30

  $729,900

  • 4 Beds
  • 2.5 Baths
  • 2,561 Sq Ft

  195 Mulford Rd, Middletown, NY 10940

  Stunning New Construction colonial on a dead end street. Welcome to your dream home set on 3 picturesque acres in the Town of Greenville, within the highly sought-after Minisink Valley School District. The Oakwood model is nestled on a private, partially wooded lot at the end of a quiet cul-de-sac, offering the perfect blend of style, comfort, and functionality. Step inside to find 4 spacious

  Chris Ogden Realty Promotions Inc

  195 Mulford Rd, 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 $157,103

  Last Listing Agent Chris Cardinal Keller Williams Realty

  268 Concord Ln, Middletown, NY 10940
• 

  Est $353,127 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,262 Sq Ft

  8 Buckingham Mews, Middletown, NY 10940

  8 Buckingham Mews, Middletown, NY 10940
• 

  

  /37

  $674,999

  • 5 Beds
  • 4.5 Baths
  • 3,642 Sq Ft

  14 Lincoln Terrace, Middletown, NY 10940

  MUST SEE!!! IMPRESSIVE PRESIDENTIAL HEIGHTS RANCH HOME!!! IN GROUND POOL!!! PRICED TO SELL!!!Discover an incredible blend of space, style, and quality construction at 14 Lincoln Terrace, Middletown NY. This truly special five bedroom, five bath home offers an impressive 3,642 square feet of refined single level living. Set in the highly desirable Presidential Heights neighborhood, known for

  Frank Muccari Cronin & Company Real Estate

  14 Lincoln Terrace, 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 $393,527

  Last Listing Agent Frank Tangredi Frank Tangredi Realty Company

  34 Pine Ct, Middletown, NY 10941
• 

  Est $350,586 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,480 Sq Ft

  9 Grosvenor Mews Unit 5, Middletown, NY 10940

  9 Grosvenor Mews Unit 5, Middletown, NY 10940
• 

  

  /44

  $505,000

  • 3 Beds
  • 2.5 Baths
  • 2,996 Sq Ft

  22 Rosecrest Ct, Middletown, NY 10940

  Discover refined living at 22 Rosecrest Court, a nearly 3,000 sq ft designer-inspired townhome blending modern comfort, thoughtful upgrades, and a lifestyle of ease within one of Middletown’s most desirable communities. Crafted in 2015 and meticulously enhanced since, this residence reflects the kind of pride and attention that only comes from true Max Effort living. From the moment you enter,

  Pete Wolven Hudson Valley Home Connection

  22 Rosecrest Ct, Middletown, NY 10940
• 

  $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

  Last Listing Agent Kevin Grier Keller Williams Hudson Valley

  95 Rolling Meadows Rd, Middletown, NY 10940
• 

  Est $347,146 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,480 Sq Ft

  3 Magdalene Close, Middletown, NY 10940

  3 Magdalene Close, Middletown, NY 10940
• 

  

  /25

  $329,900 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  114 Sarah Ln, Middletown, NY 10941

  WOW! Please check this beautiful end unit townhouse in the town of Wallkill with Goshen school district! This 3 bedrooms and 1.5 bathrooms house has almost everything brand new! New Roof, new flooring in the living room and dining are, new bathrooms, new carpet on the staircase through the hallway and the 3 bedrooms plus new hot water heater and new paved driveway for at least 6 cars! You will be

  Anita S. Cristiano HomeSmart Homes & Estates

  114 Sarah Ln, Middletown, NY 10941
• 

  $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

  Last Listing Agent Christina Gilligan HomeSmart Homes & Estates

  12 Columbine Ct, Middletown, NY 10940
• 

  Est $385,910 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,138 Sq Ft

  5 Russell Mews Unit 3, Middletown, NY 10940

  5 Russell Mews Unit 3, Middletown, NY 10940
• 

  

  /28

  $310,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,473 Sq Ft

  146 Deer Ct Dr Unit 146, Middletown, NY 10940

  Don't miss out on this this 2-bedroom, 2.5-bath townhouse in the highly desirable Deer Run Condo community in Middletown, NY. This well-kept, two-floor unit features spacious bedrooms, large windows, a master bath, central air, and second floor laundry room. From the living door, you have a sliding glass door out to your Patio, perfect for comfortable living and easy entertaining. Enjoy access to

  Chris Cardinal Keller Williams Realty

  146 Deer Ct Dr Unit 146, Middletown, NY 10940
• 

  $265,000 Sold Jun 17, 2025

  86 Brookline Ave, Middletown, NY 10940

  • 2 Beds
  • 1 Bath
  • 852 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Below List Price
  • $311/SF
  • 34 Days On Market

  Current Estimated Value $262,317

  Last Listing Agent Jonathon Lee Keller Williams Hudson Valley

  86 Brookline Ave, Middletown, NY 10940
• 

  Est $346,406 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,405 Sq Ft

  3 Agin Court Square, Middletown, NY 10940

  3 Agin Court Square, Middletown, NY 10940
• 

  

  /14

  $489,000 Pending

  • 6 Beds
  • 2 Baths
  • 2,584 Sq Ft

  96-96.5 Beattie Ave Unit 2, Middletown, NY 10940

  Well maintained side by side vinyl sided duplex. Tenant pays gas and electric, cuts grass and does the snow removal. Shared drivewayLocated minutes from schools, shopping, medical facilities and highways. Each apartment features 3 spacious bedrooms and very large dining room

  Gloria Allan John J Lease REALTORS Inc

  96-96.5 Beattie Ave Unit 2, 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

  Last Listing Agent Jackie Siracuse Absolute Real Estate of NY Inc

  63 Pierson Hill Rd, Middletown, NY 10940

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