21,379

Middletown, NY Homes

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  • 36 Karen Dr, Middletown, NY 10940

    $360,000 Sold Sep 19, 2025

    36 Karen Dr, Middletown, NY 10940

    • 3 Beds
    • 1 Bath
    • 1,436 Sq Ft
    • Built 1965

    Last Sold Summary

    • 5% Below List Price
    • $251/SF
    • 122 Days On Market

    Current Estimated Value $367,581

    Last Listing Agent Jason Madison eXp Realty

    36 Karen Dr, Middletown, NY 10940
  • /35

    $359,000 Pending

    • 3 Beds
    • 1.5 Baths
    • 1,344 Sq Ft

    14 Knox Ave, Middletown, NY 10940

    Move Right In! Your Perfect Home Awaits! Welcome to this beautifully maintained home where comfort, space, and convenience come together. Step inside and immediately notice the fresh and clean sun drenched rooms that flow throughout, setting the tone for a home that’s been lovingly cared for. The spacious kitchen offers plenty of counter space and ample cabinets for all your cooking needs—ideal

    Chris Carbone HomeSmart Homes & Estates

    14 Knox Ave, Middletown, NY 10940
  • 51 Watkins Ave, Middletown, NY 10940

    $269,000 Sold Apr 09, 2025

    51 Watkins Ave, Middletown, NY 10940

    • 3 Beds
    • 1 Bath
    • 1,360 Sq Ft
    • Built 1908

    Last Sold Summary

    • 13% Below List Price
    • $198/SF
    • 133 Days On Market

    Current Estimated Value $281,789

    Last Listing Agent Pedro Garcia Curasi Realty, Inc.

    51 Watkins Ave, Middletown, NY 10940
  • /24

    $368,800 Pending

    • 4 Beds
    • 3 Baths
    • 1,505 Sq Ft

    8 Ebury Mews, Middletown, NY 10940

    Beautiful 4-Bedroom Home in Canterbury Knolls – Town of Wallkill Welcome to this spacious and beautifully maintained 4-bedroom, 3-bath detached home in the highly sought-after Canterbury Knolls community.This rare property is one of the largest models in the neighborhood, offering the perfect blend of comfort, privacy, and convenience. Tucked away at the end of a quiet cul-de-sac and bordered

    Jonathon Lee Keller Williams Hudson Valley

    8 Ebury Mews, Middletown, NY 10940
  • 19 Woodrose Ct, Middletown, NY 10940

    $475,000 Sold Aug 21, 2025

    19 Woodrose Ct, Middletown, NY 10940

    • 3 Beds
    • 2.5 Baths
    • 2,890 Sq Ft
    • Built 2020

    Last Sold Summary

    • 6% Above List Price
    • $164/SF
    • 31 Days On Market

    Current Estimated Value $466,952

    Last Listing Agent Debbie Goldstein Howard Hanna Rand Realty

    19 Woodrose Ct, Middletown, NY 10940
  • /22

    $220,000

    • 2 Beds
    • 1 Bath
    • 820 Sq Ft

    58 Wawayanda Ave, Middletown, NY 10940

    A Great Place to Call Home or perfect for those looking to expand your real estate investment portfolio, this charming Middletown home offers the perfect blend of comfort, convenience, and value. Cozy yet spacious, this home has been thoughtfully updated and is truly move-in ready! With 2 bedrooms, a full bath and a home office/ den you will have all the space you need. Enjoy peace of mind with

    Frank Muccari Cronin & Company Real Estate

    58 Wawayanda Ave, Middletown, NY 10940
  • 47 Liberty St, Middletown, NY 10940

    $261,000 Sold Jun 27, 2025

    47 Liberty St, Middletown, NY 10940

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1890

    Last Sold Summary

    • 4% Above List Price
    • $212/SF
    • 26 Days On Market

    Current Estimated Value $270,487

    Last Listing Agent Lynelle Alessi Keller Williams Hudson Valley

    47 Liberty St, Middletown, NY 10940
  • /41

    $440,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,848 Sq Ft

    4 Thistle Ln, Middletown, NY 10940

    Spacious & Versatile Raised Ranch in Prime Middletown Location! Not your average bi-level! This move-in-ready, raised-ranch-style home in Middletown, within the Minisink Valley School District, offers the perfect blend of convenience and comfort. Located near Garnet Medical Center, Crystal Run, shopping centers, supermarkets, and with easy access to Metro-North and major highways, it’s an ideal

    Soleil Jackman Howard Hanna Rand Realty

    4 Thistle Ln, Middletown, NY 10940
  • 1538 Route 211 W, Middletown, NY 10940

    $270,000 Sold Jan 05, 2026

    1538 Route 211 W, Middletown, NY 10940

    • 2 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 1920

    Last Sold Summary

    • 10% Below List Price
    • $176/SF
    • 68 Days On Market

    Last Listing Agent John Olivero Keller Williams Realty

    1538 Route 211 W, Middletown, NY 10940
  • /26

    $329,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    136 & 140 Gillen Rd, Middletown, NY 10940

    Welcome to your affordable new home just off Route 17M! This charming 3-bedroom ranch offers incredible value that beats the recent appraisal. Enjoy the comfort of central A/C and peace of mind with a durable metal roof. The best part? The assumable lease on the solar panels delivers dramatically low electric bills, putting more money back in your pocket every month! The sale includes two

    Karie Boniface Cronin & Company Real Estate

    136 & 140 Gillen Rd, Middletown, NY 10940
  • 25 Cyprus Dr, Middletown, NY 10940

    $531,500 Sold May 01, 2025

    25 Cyprus Dr, Middletown, NY 10940

    • 2 Beds
    • 2 Baths
    • 1,868 Sq Ft
    • Built 2016

    Last Sold Summary

    • $285/SF
    • 50 Days On Market

    Current Estimated Value $561,872

    Last Listing Agent Mary Rice Israelski Howard Hanna Rand Realty

    25 Cyprus Dr, Middletown, NY 10940
  • /33

    $375,000

    • 4 Beds
    • 2.5 Baths
    • 1,668 Sq Ft

    29 Little Ave, Middletown, NY 10940

    Discover this renovated colonial home nestled in the charming city of Middletown. This spacious single-family residence offers a perfect blend of classic charm and tasteful updates. The main level features a dedicated home office, an inviting living room, and an open-concept kitchen with stunning granite countertops and a center island. A formal dining room and a convenient half bath complete

    Michael LaMorte Christie's Int. Real Estate

    29 Little Ave, Middletown, NY 10940
  • 335 Shawangunk Rd, Middletown, NY 10940

    $465,000 Sold Jul 14, 2025

    335 Shawangunk Rd, Middletown, NY 10940

    • 5 Beds
    • 3 Baths
    • 2,660 Sq Ft
    • Built 1954

    Last Sold Summary

    • 3% Above List Price
    • $175/SF
    • 53 Days On Market

    Current Estimated Value $481,370

    Last Listing Agent Marion Bruhns Howard Hanna Rand Realty

    335 Shawangunk Rd, Middletown, NY 10940
  • /32

    $375,000 Pending

    • 3 Beds
    • 1.5 Baths
    • 1,608 Sq Ft

    5 Raleigh Close Unit 3, Middletown, NY 10940

    CANTERBURY KNOLLS of Wallkill now offers this GORGEOUS TURN-KEY Contemporary style home just waiting for the right owner to call it HOME. Freshly painted walls welcomes into an open floor concept living room followed by a dining area and a spacious kitchen with granite counters, beautiful backsplash and plenty of cabinet space. Brand new stainless steel kitchen appliances fresh out of the box.

    Sandra Arnez Keller Williams Hudson Valley

    5 Raleigh Close Unit 3, Middletown, NY 10940
  • 7 Randall Terrace, Middletown, NY 10940

    $395,000 Sold Aug 28, 2025

    7 Randall Terrace, Middletown, NY 10940

    • 3 Beds
    • 1.5 Baths
    • 1,164 Sq Ft
    • Built 1953

    Last Sold Summary

    • 4% Below List Price
    • $339/SF
    • 53 Days On Market

    Current Estimated Value $393,282

    Last Listing Agent Desiree Beecham River Realty Services, Inc.

    7 Randall Terrace, Middletown, NY 10940
  • /13

    $45,000

    • Land
    • 1.4 Acres
    • $32,143 per Acre

    Pocatello Road Pocatello Rd, Middletown, NY 10940

    Country Living. yet just ten minutes to Middletown NY. area of nice homes. over 249 feet county road frontage. no close neighbors private. Rt 17 Rt 24 Rt 35 all close by. for easy commute to work. Orange County is a leader in population and company relocating more jobs Avalible. five minutes to Maple Hill Elementary School zoned R2 with no water and no sewer one would need 3 Acres so this

    John Melchior Howard Hanna Rand Realty

    Pocatello Road Pocatello Rd, Middletown, NY 10940
  • 2607 State Route 17k, Middletown, NY 10941

    $125,500 Sold Feb 14, 2025

    2607 State Route 17k, Middletown, NY 10941

    • 3 Beds
    • 2 Baths
    • 1,311 Sq Ft
    • Built 2009

    Last Sold Summary

    • 16% Below List Price
    • $96/SF
    • 79 Days On Market

    Last Listing Agent Carol Cruz Keller Williams Hudson Valley

    2607 State Route 17k, Middletown, NY 10941
  • /11

    $150,000 Pending

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    55 Glen Ave, Middletown, NY 10940

    Single faming home in the wonderful Middletown, NY up for grabs. Needs renovation. This is a fixer-upper on a large .34 acre lot. Don't miss out.

    Ishwar Rameshar YourHomeSold Guaranteed Realty

    55 Glen Ave, Middletown, NY 10940
  • 228 Concord Ln Unit 228, Middletown, NY 10940

    $140,000 Sold Dec 02, 2025

    228 Concord Ln Unit 228, Middletown, NY 10940

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

    Last Sold Summary

    • 2% Below List Price
    • $189/SF
    • 95 Days On Market

    Last Listing Agent Yasmine Delgado BHG Real Estate Green Team

    228 Concord Ln Unit 228, Middletown, NY 10940
  • /24

    $329,900

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft

    9 Fairview Ave, Middletown, NY 10940

    A must see home! This beautiful colonial home will have everything brand new - from the exterior: roof, sidings, windows, porch, deck to the interior: kitchen, all walls with plumbing and electrical lines, kitchen with brand new cabinets, countertops and appliances: refrigerator, oven/range, microwave and dishwasher, beautiful bathrooms with tiles, hardwood floorings - all NEW. Featuring 3

    Anita S. Cristiano HomeSmart Homes & Estates

    9 Fairview Ave, Middletown, NY 10940
  • 57 Jimal Dr, Middletown, NY 10940

    $210,000 Sold May 08, 2025

    57 Jimal Dr, Middletown, NY 10940

    • 1 Bed
    • 1 Bath
    • 893 Sq Ft
    • Built 1990

    Last Sold Summary

    • $235/SF
    • 128 Days On Market

    Current Estimated Value $219,184

    Last Listing Agent LIENA HAMDI Exit Realty Connections

    57 Jimal Dr, Middletown, NY 10940
  • /10

    $299,999

    • Land
    • 27.2 Acres
    • $11,029 per Acre

    328 Bloomingburg Rd, Middletown, NY 10940

    Vacant Property directly across from Fair Oaks Drive in Movie theater and a gas station with plenty of road frontage!! Minutes to RT17. 27.2 ACRES!!! Electric on road at the front of the property! Possible small farm, Big enough for horses, growing crops, family compound. R2 Zoning.The owner is currently using the property to grow crops and has an Agricultural tax exemption. NO engineering

    Jeffrey Lyons Curasi Realty, Inc.

    328 Bloomingburg Rd, Middletown, NY 10940
  • 15 Rowan St Unit 13, Middletown, NY 10940

    $405,000 Sold Sep 26, 2025

    15 Rowan St Unit 13, Middletown, NY 10940

    • 5 Beds
    • 2 Baths
    • 1,920 Sq Ft
    • Built 1900

    Last Sold Summary

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

    Current Estimated Value $397,679

    Last Listing Agent Juan Bautista Keller Williams Realty

    15 Rowan St Unit 13, Middletown, NY 10940
  • /13

    $268,000

    • 3 Beds
    • 1 Bath
    • 1,250 Sq Ft

    16 Woodland Rd, Middletown, NY 10940

    Welcome home to this nice three bedroom 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 total

    Joseph Paoli Howard Hanna Rand Realty

    16 Woodland Rd, Middletown, NY 10940
  • 22 Maryland Ave, Middletown, NY 10940

    $375,000 Sold Sep 12, 2025

    22 Maryland Ave, Middletown, NY 10940

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft
    • Built 1920

    Last Sold Summary

    • 4% Below List Price
    • $260/SF
    • 80 Days On Market

    Current Estimated Value $369,980

    Last Listing Agent Patricia Lucey Picture It Sold, LLC

    22 Maryland Ave, Middletown, NY 10940
  • /2

    $348,000

    • 3 Beds
    • 1 Bath
    • 924 Sq Ft

    8 Hill Rd, Middletown, NY 10941

    Looking for a home you can make your own without breaking the bank? This 924 sq ft ranch style home on 4 private acres with direct Wallkill River access is a rare opportunity! This home needs some cleanup and finishing touches inside. You could move right in and update as you go! The Detached Garage needs a new roof and renovations. Perfect for FHA 203K buyers who want a little sweat equity and a

    Nancy LaBarbera Keller Williams Hudson Valley

    8 Hill Rd, Middletown, NY 10941
  • 11 Black Stallion Ct, Middletown, NY 10940

    $305,000 Sold Apr 08, 2025

    11 Black Stallion Ct, Middletown, NY 10940

    • 3 Beds
    • 1.5 Baths
    • 1,188 Sq Ft
    • Built 1979

    Last Sold Summary

    • 2% Below List Price
    • $257/SF
    • 132 Days On Market

    Current Estimated Value $304,314

    Last Listing Agent Bente Brown John J Lease REALTORS Inc

    11 Black Stallion Ct, Middletown, NY 10940

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