21,198

Middletown, NY Homes

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  • /3

    $285,000

    • 2 Beds
    • 1 Bath
    • 1,019 Sq Ft

    16 Earle St Unit 14 1/2, Middletown, NY 10940

    Prime opportunity for investors, renovators, or savvy buyers looking to build instant sweat equity. With some TLC and modern updates, you can bring your vision to life and transform this house into a standout primary residence or high-yield rental investment.Unbeatable Location & Convenience:Walkable: Walking distance to SUNY Orange campus, downtown amenities, and local

    Agent Photo

    Joao Rodrigues

    Preferred Properties Real Esta

    16 Earle St Unit 14 1/2, Middletown, NY 10940
  • /8

    $1,650 Per Month

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    49 Broad St, Middletown, NY 10940

    Bright, private first-floor one-bedroom in a well-maintained two-family home on a quiet residential block in Middletown. The unit has its own entrance and its own private outdoor space, with no stairs to climb — everything on one level. Inside: a full eat-in kitchen with refrigerator included, a generous living room, a comfortable bedroom with good closet space, and a full bathroom. Gas

    49 Broad St, Middletown, NY 10940
  • 17 Woodrose Ct, Middletown, NY 10940

    $515,000

    Sold Jul 16, 2026

    17 Woodrose Ct, Middletown, NY 10940

    • 3 Beds
    • 2.5 Baths
    • 2,763 Sq Ft
    • Built 2020

    Last Sold Summary

    • $186/SF
    • 71 Days On Market

    Current Estimated Value $508,664

    Last Listing Agent Ermelinda Mclaughlin eXp Realty

    17 Woodrose Ct, Middletown, NY 10940
    • 19 Woodrose Ct, Middletown, NY 10940

      Est $506,534

      Not Listed For Sale

      19 Woodrose Ct, Middletown, NY 10940

      • 3 Beds
      • 2.5 Baths
      • 2,890 Sq Ft
      • Built 2020
      19 Woodrose Ct, Middletown, NY 10940

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Debbie Goldstein Howard Hanna Rand Realty

  • /50

    $525,000

    Pending
    • 3 Beds
    • 2 Baths
    • 2,065 Sq Ft

    225 Upper Rd, Middletown, NY 10940

    Completely renovated ranch situated on 1.44 acres in the Minisink Valley School District. This beautifully updated home features a bright open-concept layout combining the living room, dining area, and kitchen—perfect for modern living and entertaining. Large windows throughout the home allow for an abundance of natural light, creating a warm and airy atmosphere in every room.The main

    Agent Photo

    Dulce M Ferrera

    KW Hudson Valley United

    225 Upper Rd, Middletown, NY 10940
  • /9

    $2,795 Per Month

    • 2 Beds
    • 1 Bath
    • 811 Sq Ft
    • Apartment for Rent

    48 North St Unit 407, Middletown, NY 10940

    Experience the pinnacle of luxury living at North Court Apartments, located in the heart of Middletown, NY. This beautifully restored building offers spacious and thoughtfully designed unit with 2 bedrooms and 1 full bathroom , where modern elegance meets timeless charm. Each unit features premium finishes, high ceilings, and open layouts that seamlessly blend comfort with style. Enjoy the

    Tehillah Deslandes Howard Hanna Rand Realty

    48 North St Unit 407, Middletown, NY 10940
  • 36 Bert Crawford Rd, Middletown, NY 10940

    $335,000

    Sold May 20, 2026

    36 Bert Crawford Rd, Middletown, NY 10940

    • 2 Beds
    • 1 Bath
    • 836 Sq Ft
    • Built 1947

    Last Sold Summary

    • 2% Above List Price
    • $401/SF
    • 5 Days On Market

    Current Estimated Value $325,432

    Last Listing Agent Jin Pang Panorama Realty

    36 Bert Crawford Rd, Middletown, NY 10940
    • 15 Cobblestone Ln, Middletown, NY 10940

      Est $502,603

      Not Listed For Sale

      15 Cobblestone Ln, Middletown, NY 10940

      • 3 Beds
      • 2.5 Baths
      • 1,790 Sq Ft
      • Built 2010
      15 Cobblestone Ln, Middletown, NY 10940

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Katherine Burgos-Llewellyn Call it Closed Intl. Realty

  • /33

    $599,000

    • 3 Beds
    • 2.5 Baths
    • 2,086 Sq Ft

    189 School House Rd, Middletown, NY 10940

    Home sweet home! This beautiful custom built three bedroom, two and a half bathroom 2086sqft ranch is located on a gorgeous landscaped 5 acres in the Minisink Valley School District. You'll feel right at home from the moment you enter this park-like property. You have many choices of places to enjoy this home, both inside and outside. The 1900sqft main floor is open and spacious. The central

    Agent Photo

    Joseph Paoli

    Howard Hanna Rand Realty

    189 School House Rd, Middletown, NY 10940
  • /2

    $3,100 Per Month

    • 4 Beds
    • 3 Baths
    • 1,684 Sq Ft
    • House for Rent

    135 W Main St, Middletown, NY 10940

    Spacious 4-Bedroom, 3-Bath Home for Rent in Middletown – $3,100/Month Welcome to 135 West Main Street, Middletown, NY 10940, a spacious and well-located home offering approximately 1,700 square feet of comfortable living space with 3 bedrooms and 3 bathrooms. The home features generously sized rooms, plenty of living space, and a flexible layout that provides room for families,

    135 W Main St, Middletown, NY 10940
  • 9 Michele Ct, Middletown, NY 10941

    $450,000

    Sold Mar 27, 2026

    9 Michele Ct, Middletown, NY 10941

    • 4 Beds
    • 1.5 Baths
    • 2,132 Sq Ft
    • Built 1970

    Last Sold Summary

    • 13% Above List Price
    • $211/SF
    • 34 Days On Market

    Current Estimated Value $461,509

    Last Listing Agent Brian Caplicki KW Hudson Valley United

    9 Michele Ct, Middletown, NY 10941
    • 1 Lindentree Ln, Middletown, NY 10940

      Est $487,070

      Not Listed For Sale

      1 Lindentree Ln, Middletown, NY 10940

      • 3 Beds
      • 3.5 Baths
      • 1,781 Sq Ft
      • Built 2017
      1 Lindentree Ln, Middletown, NY 10940

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Katheryn DeClerck Howard Hanna Rand Realty

  • /13

    $239,000

    $10K PRICE DROP Pending
    • 3 Beds
    • 1 Bath
    • 1,250 Sq Ft

    16 Woodland Rd, Middletown, NY 10940

    Welcome home to this very nice three bedroom seasonal ranch located in the Minisink Valley School District in a quiet neighborhood! This private property is surrounded by nature with a large open yard to play and have fun in the sun. The large deck overlooks the private back yard and surrounding woods. The roof has been recently replaced. Sale includes an additional lot of 0.11 acres to bring the

    Agent Photo

    Joseph Paoli

    Howard Hanna Rand Realty

    16 Woodland Rd, Middletown, NY 10940
  • /18

    $2,100 Per Month

    • 3 Beds
    • 1 Bath
    • 1,127 Sq Ft
    • Apartment for Rent

    1 Dewitt St, Middletown, NY 10940

    MIDDLETOWN RENTAL!! Enter into a living room with plenty of window light, followed by an updated eat-in kitchen with newer counters, newer cabinets and a spacious pantry. 3 bedrooms with hardwood floors throughout and a full bath all located in one level living. Storage space available in the basemant. Plenty of parking space in rear. Minutes from schools, stores & restaurants. Commuter friendly

    Frances Levin KW Hudson Valley United

    1 Dewitt St, Middletown, NY 10940
  • 551 5th, Middletown, NY 10941

    $150,000

    Sold Mar 22, 2026

    551 5th, Middletown, NY 10941

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1997

    Last Sold Summary

    • $112/SF
    • 253 Days On Market

    Last Listing Agent Dulce M Ferrera KW Hudson Valley United

    551 5th, Middletown, NY 10941
    • 15 Sage Ct, Middletown, NY 10940

      Est $596,491

      Not Listed For Sale

      15 Sage Ct, Middletown, NY 10940

      • 2 Beds
      • 2 Baths
      • 2,153 Sq Ft
      • Built 2016
      15 Sage Ct, Middletown, NY 10940

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Linda Clark Hudson Valley Griffith

  • /48

    $425,000

    $50K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,074 Sq Ft

    57 Boorman Rd, Middletown, NY 10940

    Seller is willing to contribute towards closing costs. Welcome home to this fully renovated Dutch Colonial set on 5+ private acres in the desirable Minisink Valley Central School District, located just minutes from Middletown!Step inside to a beautifully updated kitchen featuring sleek quartz countertops, ceramic tile flooring, a subway tile backsplash, new cabinetry, and stainless steel

    Agent Photo

    Lynelle Alessi

    KW Hudson Valley United

    57 Boorman Rd, Middletown, NY 10940
  • /16

    $1,750 Per Month

    • 1 Bed
    • 1 Bath
    • 739 Sq Ft
    • Apartment for Rent

    25 Ruth Ct, Middletown, NY 10940

    GORGEOUS 1 bedroom Townhouse at Eastview Apartments!! This is a 1st floor turn key unit!! Enter into an oversized living room/dining room combo with tiled floors and plenty of natural window light. A renovated kitchen with new countertops, new cabinetry & new stainless steel appliances. 1 large bedroom with spacious closet space and vinyl floors. A beautiful full updated tiled bath with a tub,

    Sandra Arnez KW Hudson Valley United

    25 Ruth Ct, Middletown, NY 10940
  • 6 Perrins Mews, Middletown, NY 10940

    $354,000

    Sold Oct 31, 2025

    6 Perrins Mews, Middletown, NY 10940

    • 3 Beds
    • 2.5 Baths
    • 1,608 Sq Ft
    • Built 2000

    Last Sold Summary

    • 1% Above List Price
    • $220/SF
    • 12 Days On Market

    Current Estimated Value $373,824

    Last Listing Agent Maureen Cronin Cronin & Company Real Estate

    6 Perrins Mews, Middletown, NY 10940
    • /16

      Est $374,523

      Not Listed For Sale

      31-33 Linden Ave, Middletown, NY 10940

      • 7 Beds
      • 2.5 Baths
      • 2,026 Sq Ft
      • Built 1880
      31-33 Linden Ave, Middletown, NY 10940

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Karen Smith Anderson 1st Kander Realty Inc

  • /18

    $235,000

    $20K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,140 Sq Ft

    100 Hillside Dr Unit C6, Middletown, NY 10941

    Prime Location in located in Goshen School District!Welcome to this first-floor, 2-bedroom end unit condo offering 2-full baths in the desirable gated community of Hillside Village. This home offers the convenience of one-level living featuring a galley kitchen with an abundance of cabinetry. The spacious living room has sliding glass doors leading to a private patio—perfect for relaxing or

    Agent Photo

    Kathy White

    Exit Realty Connections

    100 Hillside Dr Unit C6, Middletown, NY 10941
  • /29

    $2,700 Per Month

    • 3 Beds
    • 1.5 Baths
    • 2,547 Sq Ft
    • House for Rent

    241 White Bridge Rd, Middletown, NY 10940

    Beautiful 3 Bedrooms,1.5 Bathrooms, Non-Smoking, No Pets, Minisink School DistrictWelcome to this charming and spacious 3-bedroom home nestled on nearly 3 acres in the heart of Middletown. With over 2,500 sq ft of living space, this historic property offers a peaceful country setting just minutes from local shops, schools, and commuter routes. Inside, you'll find a bright and inviting layout

    Michelle Gruberger Real Estate Circuit Inc

    241 White Bridge Rd, Middletown, NY 10940
  • 5 Mills Ave, Middletown, NY 10940

    $327,000

    Sold May 26, 2026

    5 Mills Ave, Middletown, NY 10940

    • 3 Beds
    • 1.5 Baths
    • 1,160 Sq Ft
    • Built 1883

    Last Sold Summary

    • 18% Below List Price
    • $282/SF
    • 243 Days On Market

    Current Estimated Value $320,114

    Last Listing Agent Richard Baxter Keller Williams Realty

    5 Mills Ave, Middletown, NY 10940
  • /9

    $499,000

    Pending
    • Land
    • 39.9 Acres
    • $12,506 per Acre

    700 van Burenville Rd, Middletown, NY 10940

    Discover your own 40-acre sanctuary in the Hudson Valley, a landscape of rolling meadows, a peaceful pond that set the stage for a truly picturesque retreat. Perfectly suited for equestrian pursuits, cattle, or recreational hunting.

    Agent Photo

    Joao Rodrigues

    Preferred Properties Real Esta

    700 van Burenville Rd, Middletown, NY 10940
  • /12

    $2,265 Per Month

    • 1 Bed
    • 1 Bath
    • 750 Sq Ft
    • Apartment for Rent

    48 North St Unit 201, Middletown, NY 10940

    Experience the pinnacle of luxury living at North Court Apartments, located in the heart of Middletown, NY. This beautifully restored building offers spacious and thoughtfully designed one- and two-bedroom apartments, where modern elegance meets timeless charm. Each unit features premium finishes, high ceilings, and open layouts that seamlessly blend comfort with style. Enjoy the convenience of

    Tehillah Deslandes Howard Hanna Rand Realty

    48 North St Unit 201, Middletown, NY 10940
  • /27

    $340,000

    Sold Jun 01, 2026

    164 Brookline Ave, Middletown, NY 10940

    • 2 Beds
    • 1 Bath
    • 1,050 Sq Ft
    • Built 1920

    Last Sold Summary

    • 3% Below List Price
    • $324/SF
    • 14 Days On Market

    Current Estimated Value $332,772

    Last Listing Agent Scott Alvarez Coldwell Banker Prime Properties

    164 Brookline Ave, Middletown, NY 10940
    • 3 Fortune Rd W Unit H, Middletown, NY 10941

      Not Listed For Sale

      3 Fortune Rd W Unit H, Middletown, NY 10941

      • 1 Bed
      • 1 Bath
      • 775 Sq Ft
      • Built 1972
      3 Fortune Rd W Unit H, Middletown, NY 10941

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent James LaTempa Compass Greater NY, LLC

  • /14

    $69,000

    $76K PRICE DROP Pending
    • 2 Beds
    • 1 Bath
    • 1,016 Sq Ft

    27 Lake Claire Dr, Middletown, NY 10940

    Lake Retreat! Perched high above Claire Lake with breathtaking mountain views, endless vistas, and exceptional privacy, this unique property offers a rare opportunity to create your own Hudson Valley getaway. Located in a quiet area and ready to bring your vision to life, this hidden gem combines natural beauty, character, and potential.The distinctive floor plan features 2 bedrooms, 1

    Agent Photo

    Barbara Pagella

    Coldwell Banker Realty

    27 Lake Claire Dr, Middletown, NY 10940
  • /17

    $1,450 Per Month

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Apartment for Rent

    358 North St Unit 3, Middletown, NY 10940

    Second floor one bedroom apartment located on North St right across the street from the fire department. It offers a living room, dining room, & screened in porch area. Off street parking. Tenant's income must be at least 2.5x's the rent a month, provide their own ac units, & pay gas & electric. Full application is required. No on site laundry.

    Angela Kadian Stonewall Realty Group LLC

    358 North St Unit 3, Middletown, NY 10940
  • 162 Deer Ct Dr, Middletown, NY 10940

    $265,000

    Sold Sep 29, 2025

    162 Deer Ct Dr, Middletown, NY 10940

    • 2 Beds
    • 2 Baths
    • 1,146 Sq Ft
    • Built 1991

    Last Sold Summary

    • $231/SF
    • 52 Days On Market

    Current Estimated Value $270,932

    Last Listing Agent Beverly Huaman Howard Hanna Rand Realty

    162 Deer Ct Dr, Middletown, NY 10940
    • 100 Hillside Dr Unit F10, Middletown, NY 10941

      Not Listed For Sale

      100 Hillside Dr Unit F10, Middletown, NY 10941

      • 2 Beds
      • 2.5 Baths
      • 1,216 Sq Ft
      • Built 1986
      100 Hillside Dr Unit F10, Middletown, NY 10941

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Frank Muccari Cronin & Company Real Estate

  • /41

    $375,000

    $20K PRICE INCREASE Pending
    • 3 Beds
    • 1.5 Baths
    • 1,470 Sq Ft

    4 Eaton Ct, Middletown, NY 10940

    Welcome to Canterbury Knolls! This beautifully maintained 3-bedroom, 1.5-bathroom home is move-in ready and filled with charm. Updates include a brand new roof. Some rooms and garage have been freshly painted. Step inside to find gleaming hardwood floors throughout, complemented by porcelain tiles in the entryway and kitchen. The Homeowner's Association makes life easier by handling all exterior

    Agent Photo

    Dulce M Ferrera

    KW Hudson Valley United

    4 Eaton Ct, Middletown, NY 10940
  • /12

    $2,795 Per Month

    • 2 Beds
    • 1.5 Baths
    • 854 Sq Ft
    • Apartment for Rent

    48 North St Unit 302, Middletown, NY 10940

    Experience the pinnacle of luxury living at North Court Apartments, located in the heart of Middletown, NY. This beautifully restored building offers spacious and thoughtfully designed one- and two-bedroom apartments, where modern elegance meets timeless charm. Each unit features premium finishes, high ceilings, and open layouts that seamlessly blend comfort with style. Enjoy the convenience of

    Tehillah Deslandes Howard Hanna Rand Realty

    48 North St Unit 302, Middletown, NY 10940
  • 8 Red Oak Ct, Middletown, NY 10941

    $575,000

    Sold Sep 26, 2025

    8 Red Oak Ct, Middletown, NY 10941

    • 4 Beds
    • 3 Baths
    • 2,916 Sq Ft
    • Built 1988

    Last Sold Summary

    • 3% Below List Price
    • $197/SF
    • 45 Days On Market

    Current Estimated Value $591,724

    Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

    8 Red Oak Ct, Middletown, NY 10941
    • 20 Magnolia Park Rd, Middletown, NY 10940

      Est $507,665

      Not Listed For Sale

      20 Magnolia Park Rd, Middletown, NY 10940

      • 3 Beds
      • 3.5 Baths
      • 2,000 Sq Ft
      • Built 2019
      20 Magnolia Park Rd, Middletown, NY 10940

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Eileen Ploschke BHHS Hudson Valley Properties

  • /21

    $119,000

    • Land
    • 4.27 Acres
    • $27,869 per Acre

    0 Hog Mountain Cir, Middletown, NY 12430

    This is the property with a view you have been looking for. 4.27 acres of cleared, ready to build land in the Catskill Mountains just two hours from the George Washington Bridge. Whether it is a weekend retreat you have in mind or a forever home, the view is unmatched and will bring you the peace and serenity the Catskills have to offer. This property is only 10 minutes from Belleayre Ski

    Agent Photo

    Terence Lynch

    Century 21 New West Properties

    0 Hog Mountain Cir, Middletown, NY 12430
  • /6

    $950 Per Month

    • 4,000 Sq Ft
    • Apartment for Rent

    202 Midland Lake Rd Unit BARN, Middletown, NY 10941

    Large barn (3600sf aprox) available for storage in Middletown. This is a good central location in Middletown and close to the highway for easy access from the yard to your jobs. Would make an incredible artist studio, personal storage space, or good location for a contractor or landscaper. Additional Information: ParkingFeatures:3 Car Detached,Storage: Garage,See Remarks,LeaseTerm: Over 12

    Hilary Ryan Goldman Howard Hanna Rand Realty

    202 Midland Lake Rd Unit BARN, Middletown, NY 10941
  • 214 Phillips St, Middletown, NY 10940

    $605,000

    Sold Feb 26, 2026

    214 Phillips St, Middletown, NY 10940

    • 4 Beds
    • 3.5 Baths
    • 2,760 Sq Ft
    • Built 2022

    Last Sold Summary

    • 3% Below List Price
    • $219/SF
    • 222 Days On Market

    Current Estimated Value $611,456

    Last Listing Agent Donna Gray Redfin Real Estate

    214 Phillips St, Middletown, NY 10940
    • 161 Deer Court Dr Unit 10, Middletown, NY 10940

      Est $359,253

      Not Listed For Sale

      161 Deer Court Dr Unit 10, Middletown, NY 10940

      • 3 Beds
      • 2 Baths
      • 1,508 Sq Ft
      • Built 1991
      161 Deer Court Dr Unit 10, Middletown, NY 10940

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Aylin Ippolito Cronin & Company Real Estate

Showing Results 81 - 120, Page 3 of 18

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