21,457

Middletown, NY Homes

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  • /41

    $699,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,174 Sq Ft

    TBD Kirbytown Rd, Middletown, NY 10940

    Welcome to your brand-new home, located on a 2.4 acre wooded lot in the Minisink Valley school district. The Reese model colonial was thoughtfully designed, offering 4 bedrooms and 2.5 baths with plenty of space to grow and make memories. On the first floor, you’ll find a bright and inviting living room with beautiful hardwood floors and a cozy fireplace—perfect for movie nights or gathering with

    Agent Photo

    Chris Ogden

    Realty Promotions Inc

    TBD Kirbytown Rd, Middletown, NY 10940
  • /8

    $4,000

    Total Monthly Price

    • 4 Beds
    • 3.5 Baths
    • 2,150 Sq Ft
    • House for Rent

    14 Avenue B, Middletown, NY 10940

    4 bedroom home perfectly set up for multi generation living property features an I bedroom in-law suite on the lower levelgranite counters, stainless steel appliances, central ac

    14 Avenue B, 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
    • 1425 New York 302, Middletown, NY 10941

      Est $244,653

      Not Listed For Sale

      1425 New York 302, Middletown, NY 10941

      • 3 Beds
      • 1.5 Baths
      • 1,008 Sq Ft
      • Built 1930
      1425 New York 302, Middletown, NY 10941

      Last Sold Summary

      • 136 Days On Market

      Last Listing Agent Desiree Beecham River Realty Services, Inc.

  • /35

    $980,000

    New Construction
    • 6 Beds
    • 6 Baths
    • 4,480 Sq Ft

    5-7 Blanchard St, Middletown, NY 10940

    Brand new construction duplex in heart of Middletown. Each spacious unit features 3 bedrooms, 2.5 baths, garage, central A/C and a bright, sun-filled open floor plan thoughtfully designed for today's lifestyle. Beautiful kitchens with expansive windows create an abundance of natural light, with one unit showcasing elegant dove white cabinetry while the other offers rich espresso cabinetry, both

    Agent Photo

    JoAnn Maxwell

    Howard Hanna Rand Realty

    5-7 Blanchard St, Middletown, NY 10940
  • /28

    $1,700

    Total Monthly Price

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

    13 Benton Ave, Middletown, NY 10940

    Touro Students OnlyNo Broker Fee – Rent Directly from the OwnerThis property is ideal for a student seeking a quiet, comfortable place to live and study. Conveniently located within walking distance of the school.Property Features:Smoke-free buildingNo petsOn-site laundry facilitiesParking includedHeat includedLaundry included in the

    13 Benton Ave, 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
    • 2 Stonerose Ct, Middletown, NY 10940

      Est $527,329

      Not Listed For Sale

      2 Stonerose Ct, Middletown, NY 10940

      • 4 Beds
      • 3.5 Baths
      • 2,966 Sq Ft
      • Built 2015
      2 Stonerose Ct, Middletown, NY 10940

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Sandra Arnez KW Hudson Valley United

  • /45

    $589,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft

    121 Quail Ridge Rd, Middletown, NY 12421

    Welcome to your private mountain retreat on 5.3 acres, with breathtaking panoramic views. Situated in the Quail Ridge development, on a dead end Town Maintained Road, properties like this rarely become available. This charming chalet blends classic mountain warmth with everyday comfort and features a southeast-to-west wraparound deck—perfect for morning coffee, soaking in the scenery, sunset

    Robert Dillon Listing by Coldwell Banker Timberland Properties

    121 Quail Ridge Rd, Middletown, NY 12421
  • /28

    $1,700

    Total Monthly Price

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

    13 Benton Ave, Middletown, NY 10940

    Touro Students OnlyNo Broker Fee – Rent Directly from the OwnerThis property is ideal for a student seeking a quiet, comfortable place to live and study. Conveniently located within walking distance of the school.Property Features:Smoke-free buildingNo petsOn-site laundry facilitiesParking includedHeat includedLaundry included in the

    13 Benton Ave, Middletown, NY 10940
  • 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
    • /33

      Not Listed For Sale

      28 Roosevelt Ave, Middletown, NY 10940

      • 5 Beds
      • 1.5 Baths
      • 1,760 Sq Ft
      • Built 1900
      28 Roosevelt Ave, Middletown, NY 10940

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Christina Lake Davis R. Chant - Milford

  • /33

    $499,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,211 Sq Ft

    60 Magnolia Park Rd, Middletown, NY 10940

    Beautifully cared-for 3 bedroom, 2.5-bath townhouse in the heart of Middletown! Spanning three levels, this home offers comfortable, versatile living with hardwood floors throughout both the main and second levels. The bright main floor features an open-concept living area featuring a fireplace, a dining area, along with a modern kitchen complete with granite countertops and ample cabinet space.

    Sandra Laramore Redfin Real Estate

    60 Magnolia Park Rd, Middletown, NY 10940
  • /12

    $2,525 Per Month

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

    48 North St Unit 406, 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 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 the

    Tehillah Deslandes Howard Hanna Rand Realty

    48 North St Unit 406, Middletown, NY 10940
  • 553 Route 17m, Middletown, NY 10940

    $317,000

    Sold Aug 08, 2025

    553 Route 17m, Middletown, NY 10940

    • 2 Beds
    • 1 Bath
    • 1,225 Sq Ft
    • Built 1920

    Last Sold Summary

    • 1% Below List Price
    • $259/SF
    • 98 Days On Market

    Current Estimated Value $335,799

    Last Listing Agent Derek Greene Greene Realty Group

    553 Route 17m, Middletown, NY 10940
    • 20 State St, Middletown, NY 10940

      Not Listed For Sale

      20 State St, Middletown, NY 10940

      • 3 Beds
      • 1.5 Baths
      • 1,225 Sq Ft
      • Built 1971
      20 State St, Middletown, NY 10940

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Carol Cruz KW Hudson Valley United

  • /49

    $585,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,253 Sq Ft

    1652 Thompson Hollow Rd, Middletown, NY 12459

    Set in the heart of the picturesque New Kingston Valley, this enchanting two-bedroom, two-bath cottage is privately situated on 20 remarkable acres, offering an increasingly rare combination of complete seclusion, stunning natural beauty, and endless potential. Surrounded by forest and breathtaking mountain views, the property is a sanctuary where the sounds of a year-round stream and the beauty

    Jeffrey Ashton Listing by Coldwell Banker Timberland Properties

    1652 Thompson Hollow Rd, Middletown, NY 12459
  • /9

    $2,000 Per Month

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

    4 Fortune Rd W Unit 4G, Scotchtown, NY 10941

    Welcome to your new home in Middletown, NY! This charming one-bedroom townhouse offers a comfortable living space of 775 square feet that is perfect for those seeking a cozy retreat. With large windows in the spacious living area, natural light floods the home creating a warm and inviting atmosphere. The kitchen features white cabinetry and essential appliances, making meal preparation a joy.

    4 Fortune Rd W Unit 4G, Scotchtown, NY 10941
  • 145 Academy Ave, Middletown, NY 10940

    $455,000

    Sold Apr 12, 2026

    145 Academy Ave, Middletown, NY 10940

    • 4 Beds
    • 2 Baths
    • 2,545 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Above List Price
    • $179/SF
    • 41 Days On Market

    Current Estimated Value $442,290

    Last Listing Agent Sandra Arnez KW Hudson Valley United

    145 Academy Ave, Middletown, NY 10940
    • 3 Fortune Rd W Unit K, Middletown, NY 10941

      Not Listed For Sale

      3 Fortune Rd W Unit K, Middletown, NY 10941

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

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Marie Altieri Howard Hanna Rand Realty

  • /50

    $799,999

    Pending
    • 4 Beds
    • 3.5 Baths
    • 2,462 Sq Ft

    48 Lone Indian Trail, Middletown, NY 10940

    SPECTACULAR 180 PANORAMIC MOUNTAIN VIEWS AS FAR AS THE EYES CAN SEE w/ THIS IMMACULATE 4 BR / 3.5 BATH CUSTOM, TWO-STORY, CONTEMPORARY HOME ON FULLY FINISHED DAYLIGHT WALKOUT BASEMENT w/ LARGE WRAPAROUND BACK DECK & 2ND STORY PRIMARY SUITE BALCONY OVERLOOKING THE BREATHTAKING VIEWS OF THE HUDSON VALLEY LANDSCAPE, AND A 2-CAR GARAGE, PRIVATELY SET ON 17.8 ACRES w/ SPRAWLING & WELL-MAINTAINED LAWN

    Olivia Cappelli Donna Ruffino Realty Corp

    48 Lone Indian Trail, Middletown, NY 10940
  • /11

    $3,145 Per Month

    • 2 Beds
    • 2 Baths
    • 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 2 full bathrooms , 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
  • 406 4th Ave, Middletown, NY 10941

    $30,000

    Sold Aug 07, 2026

    406 4th Ave, Middletown, NY 10941

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft
    • Built 1973

    Last Sold Summary

    • 23% Below List Price
    • $33/SF
    • 103 Days On Market

    Last Listing Agent John Nahass Century 21 Full Service Realty

    406 4th Ave, Middletown, NY 10941
    • 5 Fortune Rd W Unit M, Middletown, NY 10941

      Not Listed For Sale

      5 Fortune Rd W Unit M, Middletown, NY 10941

      • 2 Beds
      • 2 Baths
      • 1,112 Sq Ft
      • Built 1972
      5 Fortune Rd W Unit M, Middletown, NY 10941

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Marie Altieri Howard Hanna Rand Realty

  • /24

    $575,000

    Open Sun 11AM - 2PM $24K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,392 Sq Ft

    5 Oak Ridge Rd, Middletown, NY 10940

    Built in 2020, this spacious 2,392 sq ft home offers 4 bedrooms, 3 full bathrooms, and a 2-car garage. The upper level boasts an open-concept layout with vaulted ceilings, a modern kitchen featuring granite countertops and stainless steel appliances, a bright living room, and three bedrooms, including the primary suite, and two full baths. The finished lower level adds even more living space with

    Sandra Laramore Redfin Real Estate

    5 Oak Ridge Rd, Middletown, NY 10940
  • /10

    $2,300 Per Month

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    90 Montgomery St Unit 2, Middletown, NY 10940

    Renovated 2-Bedroom Apartment in Middletown — Move-In Ready Situated at 90 Montgomery St in Middletown, NY, this freshly renovated 2-bedroom, 1-bath apartment offers approximately 800 sq ft of thoughtfully updated living space. Built in 1950 and recently refreshed with new paint and contemporary finishes, the unit blends mid-century character with modern convenience. Available beginning April 1,

    90 Montgomery St Unit 2, Middletown, NY 10940
  • 317 Wawayanda Ave, Middletown, NY 10940

    $335,000

    Sold Sep 30, 2025

    317 Wawayanda Ave, Middletown, NY 10940

    • 4 Beds
    • 1 Bath
    • 1,124 Sq Ft
    • Built 1950

    Last Sold Summary

    • 3% Above List Price
    • $298/SF
    • 89 Days On Market

    Current Estimated Value $332,102

    Last Listing Agent Pete Wolven Hudson Valley Home Connection

    317 Wawayanda Ave, Middletown, NY 10940
    • 100 Hillside Dr Unit C8, Middletown, NY 10941

      Not Listed For Sale

      100 Hillside Dr Unit C8, Middletown, NY 10941

      • 2 Beds
      • 2.5 Baths
      • 1,418 Sq Ft
      • Built 1987
      100 Hillside Dr Unit C8, Middletown, NY 10941

      Last Sold Summary

      • 116 Days On Market

      Last Listing Agent Xiaohui Cui KW Hudson Valley United

  • /35

    $425,000

    $5K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    25 Ferrara Dr, Middletown, NY 10941

    Step into this Beautifully renovated 3 Bedroom, 1 Bath Split Level Home. Perfectly updated with Brand New Roof, Windows, Bright and Airy Kitchen and Modern Bathroom. Brand New Stainless Steel Appliances in Kitchen. Hardwood floors throughout. Nestled on a spacious charming piece of property. Great for outdoor entertaining. It's ready for you to call Home.Great Commuter Location. Close to

    Tracy Lockhart RE/MAX Benchmark Realty Group

    25 Ferrara Dr, Middletown, NY 10941
  • /11

    $2,200 Per Month

    • 2 Beds
    • 1 Bath
    • 1,041 Sq Ft
    • House for Rent

    157 White Bridge Rd, Middletown, NY 10940

    Updated ranch-style rental on approximately 12 private acres in the Minisink Valley School District. This single-family home offers 2 bedroom, 1 full bathroom, and approximately 1,041 sq ft of living space. Features include vaulted ceilings with exposed beams, skylight, updated bathroom, open kitchen, recessed lighting, sliding glass doors, and peaceful surroundings with privacy. Conveniently

    Yosseline Genao KW Hudson Valley United

    157 White Bridge Rd, Middletown, NY 10940
  • 29 Beacon St, Middletown, NY 10940

    $407,500

    Sold May 04, 2026

    29 Beacon St, Middletown, NY 10940

    • 3 Beds
    • 1 Bath
    • 1,886 Sq Ft
    • Built 1910

    Last Sold Summary

    • 4% Below List Price
    • $216/SF
    • 32 Days On Market

    Current Estimated Value $401,179

    Last Listing Agent Jessica Evans KW Hudson Valley United

    29 Beacon St, Middletown, NY 10940
    • 92 Linden Ave, Middletown, NY 10940

      Est $126,018

      Not Listed For Sale

      92 Linden Ave, Middletown, NY 10940

      • Built 1918
      92 Linden Ave, Middletown, NY 10940

      Last Sold Summary

      • 83 Days On Market

      Last Listing Agent Ashley Olson Minard eXp Realty

  • /17

    $399,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,792 Sq Ft

    8 Walnut Ln, Middletown, NY 10940

    Opportunity knocks in one of Middletown's most convenient and desirable locations! This spacious 3 bedroom, 2.5-bath Colonial with a 2-car garage offers the perfect blend of size, location and potential. Featuring hardwood floors, a functional layout, and a kitchen equipped with stainless steel appliances and granite countertops, this home provides an excellent foundation for creating your own

    Bonnie Natt Realty Promotions Inc

    8 Walnut Ln, Middletown, NY 10940
  • /2

    $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 baseboard

    49 Broad St, Middletown, NY 10940
  • 34 Feiertag Rd, Middletown, NY 10941

    $550,000

    Sold Apr 18, 2026

    34 Feiertag Rd, Middletown, NY 10941

    • 3 Beds
    • 3 Baths
    • 3,021 Sq Ft
    • Built 2000

    Last Sold Summary

    • 15% Below List Price
    • $182/SF
    • 210 Days On Market

    Current Estimated Value $610,231

    Last Listing Agent Julianna Cotthaus 1st Independent Realty Grp

    34 Feiertag Rd, Middletown, NY 10941
    • 34 Linden Ave, Middletown, NY 10940

      Not Listed For Sale

      34 Linden Ave, Middletown, NY 10940

      • 5 Beds
      • 5 Baths
      • 2,538 Sq Ft
      • Built 1920
      34 Linden Ave, Middletown, NY 10940

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Moses Zwiebel MS Realty Group USA, Inc

  • /28

    $399,000

    Open Sun 1PM - 3PM
    • 2 Beds
    • 2.5 Baths
    • 1,337 Sq Ft

    19 Putters Way Unit 6, Middletown, NY 10940

    Beautiful Townhouse in Fairways at Wallkill! Enjoy maintenance-free living in this desirable Fairways community townhouse. Conveniently located near major highways, shopping, and Orange Regional Medical Center, this home features 2 bedrooms, 2.5 bathrooms, a spacious living room, and a bright private balcony overlooking the pool.Residents have access to outstanding amenities including a

    Xiaohui Cui KW Hudson Valley United

    19 Putters Way Unit 6, Middletown, NY 10940
  • /32

    $2,600 Per Month

    • 3 Beds
    • 1 Bath
    • 1,928 Sq Ft
    • House for Rent

    950 Route 17m, Middletown, NY 10940

    STUNNING 3 bedroom/1bath Capecod surrounded by acres of beautifully landscaped views located on the outskirts of Middletown is now available for immediate occupancy. Enter into an oversized living room with a fireplace followed by a Formal dining room with mint shiny hardwood floors. A spacious kitchen with plenty of custom cabinetry and counter space. Beautifully stainless steel appliances and

    Sandra Arnez KW Hudson Valley United

    950 Route 17m, Middletown, NY 10940
  • 16 Robertson Dr, Middletown, NY 10940

    $371,000

    Sold Aug 19, 2025

    16 Robertson Dr, Middletown, NY 10940

    • 2 Beds
    • 1.5 Baths
    • 1,404 Sq Ft
    • Built 1955

    Last Sold Summary

    • 24% Above List Price
    • $264/SF
    • 19 Days On Market

    Current Estimated Value $371,982

    Last Listing Agent Virginia Corbett eXp Realty

    16 Robertson Dr, Middletown, NY 10940
    • 19 Meadow View Dr, Middletown, NY 10940

      Est $510,759

      Not Listed For Sale

      19 Meadow View Dr, Middletown, NY 10940

      • 3 Beds
      • 4 Baths
      • 2,581 Sq Ft
      • Built 2014
      19 Meadow View Dr, Middletown, NY 10940

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Rebecca Kane KW Hudson Valley United

Showing Results 121 - 160, Page 4 of 18

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