21,591

Middletown, NY Homes

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  • /19

    $159,900

    $12K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    509 5th Ave, Middletown, NY 10941

    Want to buy an almost new home for $169900? That’s right, ONLY THREE YEARS OLD!! This home needs to be seen to be believed. Two large bedrooms with large closets. Huge open floorplan living room and dining room with lots of windows for natural light. Large deck for relaxing and entertaining. So many cabinets and a ton of counter space with stainless steel appliances. Full main bathroom with a tub

    John Nahass Century 21 Full Service Realty

    509 5th Ave, Middletown, NY 10941
  • /15

    $2,400 Per Month

    • 2 Beds
    • 2 Baths
    • 1,142 Sq Ft
    • Apartment for Rent

    206 Golf Links Rd Unit 621, Middletown, NY 10940

    This new 2 bedroom 2 bath apartment features a modern and stylish design, with high-quality finishes and attention to detail throughout. The living room is adorned with a large window that allows plenty of natural light to illuminate the space, creating an inviting and airy atmosphere. The kitchen is equipped with stainless steel appliances, sleek quartz countertops, ample cabinet storage, and a

    John Chirico Curasi Realty, Inc.

    206 Golf Links Rd Unit 621, Middletown, NY 10940
  • 104 Monhagen Ave, Middletown, NY 10940

    $410,000

    Sold Oct 16, 2025

    104 Monhagen Ave, Middletown, NY 10940

    • 3 Beds
    • 2.5 Baths
    • 2,223 Sq Ft
    • Built 1875

    Last Sold Summary

    • 4% Below List Price
    • $184/SF
    • 19 Days On Market

    Current Estimated Value $406,307

    Last Listing Agent Jeffrey Hozias Howard Hanna Rand Realty

    104 Monhagen Ave, Middletown, NY 10940
  • /2

    $345,000

    Open Sun 11:30AM - 2PM Coming Soon
    • 2 Beds
    • 2.5 Baths
    • 1,241 Sq Ft

    45 Kensington Way, Middletown, NY 10940

    Welcome Home to Lake Front living at it's best! Quiet and peaceful this end unit offers the best of both worlds. The feel of a vacation home without the hassle of maintaining it. Nestled in the sleepy Water's Edge Condo Community, this unit offers 2 large bedrooms, and 2 &1/2 baths. Featuring engineered flooring, granite counter tops and a nice open living-dining lower level. Wake up each morning

    Dien Le Duc Hudson Premium Realty

    45 Kensington Way, Middletown, NY 10940
  • /12

    $2,000 Per Month

    • Property for Rent

    28 Pilgrim Corners Rd Unit 30, Middletown, NY 10940

    Rare barn lease opportunity on an iconic Hudson Valley farm property. Situated on a scenic acreage setting, this impressive barn offers substantial space with excellent accessibility and room for equipment, storage, agricultural operations, artisan trades, or approved business activities. Enjoy a private country environment while remaining just minutes from Middletown's shopping, dining, and

    Anthony Rivas KW Hudson Valley Untied

    28 Pilgrim Corners Rd Unit 30, Middletown, NY 10940
  • 125 Whipple Rd, Middletown, NY 10940

    $615,000

    Sold Jan 23, 2026

    125 Whipple Rd, Middletown, NY 10940

    • 4 Beds
    • 3 Baths
    • 2,552 Sq Ft
    • Built 2002

    Last Sold Summary

    • 4% Below List Price
    • $241/SF
    • 118 Days On Market

    Current Estimated Value $609,380

    Last Listing Agent Eboni Navas Julia B Fee Sothebys Int. Rlty

    125 Whipple Rd, Middletown, NY 10940
  • /33

    $259,000

    • 2 Beds
    • 1.5 Baths
    • 1,230 Sq Ft

    129 Concord Ln Unit 129, Middletown, NY 10940

    An exceptional opportunity for homeowners and savvy investors, this sun-drenched, southeast-facing condo is located in one of Middletown’s rare communities with NO rental restrictions. Experience the comfort of two-level living with a thoughtful layout featuring a spacious living room on the main floor and private bedrooms upstairs. This home offers ultimate peace of mind with a Boiler and Water

    Hai Li KW Hudson Valley Untied

    129 Concord Ln Unit 129, Middletown, NY 10940
  • /13

    $2,400 Per Month

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

    238 Concord Ln, Middletown, NY 10940

    Freshly updated 2-bedroom, 1.5-bath end-unit condominium located in the desirable Buttonwood Hills community. This move-in ready home offers convenient one-level living with a bright and functional layout filled with natural light. The kitchen overlooks the spacious living and dining areas, creating an open and welcoming atmosphere for everyday living and entertaining.Additional features

    Maria Sairrino Cronin & Company Real Estate

    238 Concord Ln, Middletown, NY 10940
  • 42 Inwood Rd, Middletown, NY 10941

    $175,000

    Sold Aug 26, 2025

    42 Inwood Rd, Middletown, NY 10941

    • 1 Bed
    • 1 Bath
    • 750 Sq Ft
    • Built 1975

    Last Sold Summary

    • $233/SF
    • 24 Days On Market

    Last Listing Agent Gloria Rivera KW Hudson Valley Untied

    42 Inwood Rd, Middletown, NY 10941
  • /50

    $2,250,000

    $445K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 20,730 Sq Ft

    285 Hill Rd, Middletown, NY 10940

    For your consideration is 285 Hill Road, a premier equine boarding, training and showing facility formerly known as Hilltop Equestrian Center and Seven Meadows Farm. Designed for function and beauty, it's a welcoming destination for both clients and guests. Numerous shows and clinics have been successfully hosted here over the years. The property includes a professional indoor arena complex, 2

    Michelle Genatempo Howard Hanna Rand Realty

    285 Hill Rd, Middletown, NY 10940
  • /7

    $2,600 Per Month

    • 3 Beds
    • 1 Bath
    • 1,088 Sq Ft
    • House for Rent

    63 Broad St, Middletown, NY 10940

    3-bedroom, 1-bath colonial rental in Middletown featuring a spacious layout, front porch, and detached one-car garage. Conveniently located near shopping, dining, and major roadways.

    Doreen Crowther Howard Hanna Rand Realty

    63 Broad St, Middletown, NY 10940
  • /31

    $410,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,513 Sq Ft

    366 van Burenville Rd, Middletown, NY 10940

    Welcome to Beautiful 366 Van Burenville Rd. Enjoy this inviting home that is situated on almost 1 Acre of private, level property in the Town of Wallkill. Featuring Hardwood Floors, Large open Living Room, Formal Dining room with a Bay window, Wanes Coating with custom trim. Spacious Eat in Kitchen with Stainless Steel Appliances, Lots of Kitchen Cabinetry, and Countertop Space. New Bathroom with

    John Biasi Howard Hanna Rand Realty

    366 van Burenville Rd, Middletown, NY 10940
  • /10

    $3,500 Per Month

    • 4 Beds
    • 2 Baths
    • 1,466 Sq Ft
    • House for Rent

    225 Monhagen Ave, Middletown, NY 10940

    Great Location on Route 211 – Spacious 3-Bedroom Upstairs Unit with Large Backyard. The well-maintained upstairs unit located on Route 211 in Middletown offers both convenience and comfortable living. This rental features 3 bedrooms, a bright and spacious living room, and a functional kitchen—perfect for everyday living. Enjoy access to a large backyard, ideal for kids’ activities, outdoor

    Jin Pang Panorama Realty

    225 Monhagen Ave, Middletown, NY 10940
  • 11 Cobblestone Ln, Middletown, NY 10940

    $460,000

    Sold Mar 18, 2026

    11 Cobblestone Ln, Middletown, NY 10940

    • 3 Beds
    • 2.5 Baths
    • 1,899 Sq Ft
    • Built 2011

    Last Sold Summary

    • 6% Below List Price
    • $242/SF
    • 114 Days On Market

    Current Estimated Value $465,127

    Last Listing Agent Antoinette Gundersen HomeSmart Homes & Estates

    11 Cobblestone Ln, Middletown, NY 10940
    • Unlisted Address

      Est $558,612

      Not Listed For Sale

      Unlisted Address

      • 4 Beds
      • 3 Baths
      • 2,091 Sq Ft
      • Built 2009
      Unlisted Address

      Last Sold Summary

      • 68 Days On Market

  • /49

    $799,000

    • 5 Beds
    • 4.5 Baths
    • 4,085 Sq Ft

    3 Truman Ct, Middletown, NY 10940

    Step into refined living with this beautifully maintained 5-bedroom Colonial-style home, where classic charm meets upscale upgrades. From the moment you enter, you’re welcomed by exquisite craftsmanship, including detailed crown molding and rich hardwood floors that flow seamlessly throughout the main living spaces.This spacious residence features three elegant fireplaces, creating warm and

    Dominick Tufano RE/MAX Benchmark Realty Group

    3 Truman Ct, Middletown, NY 10940
  • /22

    $2,400 Per Month

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

    90 Montgomery St Unit Upper, Middletown, NY 10940

    Fully renovated apartment in the center of downtown Middletown close to shopping and restaurants. Two bedrooms with large open eat-in kitchen, living room, bathroom, and backyard access with all new floors, paint, fixtures, and appliances. The Railroad Avenue Bus Terminal is a few short blocks away. Shared driveway and house located on a dead-end road with little city traffic. Ready for new

    Hilary Ryan Goldman Howard Hanna Rand Realty

    90 Montgomery St Unit Upper, Middletown, NY 10940
  • 20 Avoncroft Ln, Middletown, NY 10940

    $485,000

    Sold Jul 01, 2025

    20 Avoncroft Ln, Middletown, NY 10940

    • 3 Beds
    • 2.5 Baths
    • 2,521 Sq Ft
    • Built 2009

    Last Sold Summary

    • 1% Below List Price
    • $192/SF
    • 157 Days On Market

    Current Estimated Value $490,027

    Last Listing Agent D'Wana Haynesworth YourHomeSold Guaranteed Realty

    20 Avoncroft Ln, Middletown, NY 10940
  • /28

    $434,999

    • 3 Beds
    • 2 Baths
    • 1,614 Sq Ft

    9 Chestnut St, Middletown, NY 10940

    Move in ready Colonial that perfectly balances classic charm with tasteful updates. This home has been meticulously maintained and features a bright, inviting interior. The kitchen serves as the heart of the home, updated with white shaker cabinets, granite countertops, an oversized island, and a full suite of stainless steel appliances. For added convenience, the first floor includes a dedicated

    Christian Lugo Howard Hanna Rand Realty

    9 Chestnut St, Middletown, NY 10940
  • /32

    $4,900 Per Month

    • 4 Beds
    • 3.5 Baths
    • 4,133 Sq Ft
    • House for Rent

    201 County Route 50, Middletown, NY 10940

    GORGEOUS 4 bedroom/3 bath now available in the town of Wallkill. Discover your family's oasis on 4.1 acres next to West Hills Country Club! This stunning 4-bedroom home, complete with a grand master suite, will exceed your expectations. Enjoy the above-ground pool with smart monitoring, heated outdoor tub, and spacious deck with grill. Kids will love the playground, while adults appreciate the

    Sandra Arnez KW Hudson Valley Untied

    201 County Route 50, Middletown, NY 10940
  • /2

    $472,000

    Sold Feb 13, 2026

    7001 James Francis Dr, Lockport-Town, NY 14094

    • 3 Beds
    • 2 Baths
    • 1,756 Sq Ft
    • Built 2026

    Last Sold Summary

    • 5% Above List Price
    • $269/SF
    • 0 Days On Market

    Last Listing Agent Kathleen Dimillo Listing by HUNT Real Estate Corporation

    7001 James Francis Dr, Lockport-Town, NY 14094
  • /34

    $640,000

    $10K PRICE DROP Pending Pre-Foreclosure
    • 4 Beds
    • 2.5 Baths
    • 2,424 Sq Ft

    235 Maples Rd, Middletown, NY 10940

    This well-maintained spacious Colonial Home is ideally situated on a 2 Acre Lot in the Town of Wallkill Countryside. Lovely Kitchen W/Breakfast nook overlooks a Large Level Backyard & Private Rear Entertainment Deck. An entry foyer greets you when you arrive at this home, that features a Formal Dining Room, Living Room, Family Room, Powder Room, & mud Room/Laundry to complete the 1st Floor. The

    Shernette Hall VYLLA Home

    235 Maples Rd, Middletown, NY 10940
  • /27

    $2,600 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,126 Sq Ft
    • House for Rent

    27 Oliver Ave, Middletown, NY 10940

    House is just updated. Mover right in. All large rooms. Level fenced backyard. Great location close to park, transportation and shopping.

    Feng Chang Acer Realty Inc

    27 Oliver Ave, Middletown, NY 10940
  • 122 W Main St, Middletown, NY 10940

    $620,000

    Sold Sep 18, 2025

    122 W Main St, Middletown, NY 10940

    • 6 Beds
    • 4 Baths
    • 4,491 Sq Ft
    • Built 1900

    Last Sold Summary

    • 11% Below List Price
    • $138/SF
    • 26 Days On Market

    Last Listing Agent Joao Rodrigues Preferred Properties Real Esta

    122 W Main St, Middletown, NY 10940
  • /17

    $429,000

    $30K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,097 Sq Ft

    4 Kless Ct, Middletown, NY 10940

    Welcome to this well-kept 3-bedroom home with a bonus loft, set in the Maple Fields community. The first floor offers an easy, open layout with a comfortable living area that leads out to a private patio, along with a dining space and a kitchen that includes a pantry, tile accents, and stainless steel appliances. Upstairs you’ll find the primary bedroom featuring a walk-in closet and its own

    Bryant Moran YourHomeSold Guaranteed Realty

    4 Kless Ct, Middletown, NY 10940
  • /24

    $2,200 Per Month

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

    935 Tower Ridge Cir, Middletown, NY 10941

    Welcome to Tower Ridge, where comfort and convenience come together in this beautifully maintained 1-bedroom, 1-bathroom condominium available for rent. This move-in ready home features an open-concept layout with hardwood floors, granite countertops, stainless steel appliances, central air conditioning, and an in-unit washer and dryer. The spacious bedroom offers ample closet space, while the

    Richard Guerrero KW Hudson Valley Untied

    935 Tower Ridge Cir, Middletown, NY 10941
  • 118 White Bridge Rd, Middletown, NY 10940

    $429,000

    Sold Aug 20, 2025

    118 White Bridge Rd, Middletown, NY 10940

    • 3 Beds
    • 1.5 Baths
    • 1,794 Sq Ft
    • Built 1991

    Last Sold Summary

    • 7% Below List Price
    • $239/SF
    • 57 Days On Market

    Current Estimated Value $433,682

    Last Listing Agent Feng Chang Acer Realty Inc

    118 White Bridge Rd, Middletown, NY 10940
  • /50

    $399,000

    • 3 Beds
    • 1.5 Baths
    • 1,446 Sq Ft

    4 Saint Eve Ct, Middletown, NY 10940

    Situated on a quiet cul-de-sac, this spacious and versatile home offers the perfect blend of comfort, convenience, and flexibility. Enjoy a large yard ideal for entertaining, complete with a deck and patio for outdoor gatherings and relaxation. Inside, the home features ample parking, 3-zone heating for year-round comfort, and an all-inclusive room/office perfect for working from home, guests, or

    Robin Cohen Keller Williams Realty

    4 Saint Eve Ct, Middletown, NY 10940
  • /23

    $3,500 Per Month

    • 4 Beds
    • 3 Baths
    • 1,954 Sq Ft
    • House for Rent

    54 Madison Ave, Middletown, NY 10940

    A beautiful 2 year old colonial home is now available to rent in the center of Middletown NY. Walk in distance to Orange County Community College and minutes to shopping, NYC transportation, hospital and medical centers. This stunning home is offering 4 bedrooms and 3 full bathrooms plus a walk out unfinished basement and one car garage. Landlord requires Tenants to have minimum 650 credit score,

    Anita S. Cristiano HomeSmart Homes & Estates

    54 Madison Ave, Middletown, NY 10940
  • 261 Ruth Ct, Middletown, NY 10940

    $241,000

    Sold Feb 06, 2026

    261 Ruth Ct, Middletown, NY 10940

    • 2 Beds
    • 2 Baths
    • 880 Sq Ft
    • Built 2006

    Last Sold Summary

    • 5% Above List Price
    • $274/SF
    • 27 Days On Market

    Current Estimated Value $242,881

    Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

    261 Ruth Ct, Middletown, NY 10940

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