21,401

Middletown, NY Homes

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  • 42 Inwood Rd, Middletown, NY 10941

    $175,000 Sold Aug 26, 2025

    • 750 Sq Ft
    • $233/SF
    • 24 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1975

    42 Inwood Rd, Middletown, NY 10941

    This well-maintained ground-floor condo offers a blend of comfort & style with updates completed in 2017. Featuring modern flooring, updated doors & a renovated bathroom. The kitchen boasts granite counters, a tiled backsplash and stainless steel appliances-all installed during the renovation. The spacious bedroom includes a large walk-in closet, and the open living/dining area offers flexible

    Gloria Rivera Keller Williams Hudson Valley

    42 Inwood Rd, Middletown, NY 10941
  • 21-23 Highland Ave, Middletown, NY 10940
    21-23 Highland Ave, Middletown, NY 10940
    21-23 Highland Ave, Middletown, NY 10940
    /18

    $595,000

    • 8 Beds
    • 3 Baths
    • 3,000 Sq Ft

    21-23 Highland Ave, Middletown, NY 10940

    Kathleen Christopherson EXCLUSIVE SALES AND RENTALS

    21-23 Highland Ave, Middletown, NY 10940
  • 34 Pine Ct, Middletown, NY 10941

    $370,000 Sold Aug 26, 2025

    • 2,358 Sq Ft
    • $157/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1971

    34 Pine Ct, Middletown, NY 10941

    This commuter friendly home is located in a rural setting outside of the City of Middletown, but is close to NY Route 17, Interstate 84, the NYS Thruway, Middletown railway station and Stewart International Airport. There are major shopping centers & grocery stores nearby.This home is set in a quiet established residential neighborhood with beautiful mature trees. Features include a large

    Frank Tangredi Frank Tangredi Realty Company

    34 Pine Ct, Middletown, NY 10941
  • 273 Pine Grove Rd, Middletown, NY 10940
    273 Pine Grove Rd, Middletown, NY 10940
    273 Pine Grove Rd, Middletown, NY 10940
    /39

    $789,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 3,129 Sq Ft

    273 Pine Grove Rd, Middletown, NY 10940

    **** HAS ACCEPTED OFFER ***** ---------COMPLETELY TURN KEY !!!!! -----------RETIRED CUSTOM BUILDERS (husband and wife) - poured their hearts into their family home.--------------GENTLY USED and IMPECCABLY maintained, ----------- It is a WHOLE LOTTA HOUSE and has MANY UPGRADES INCLUDING : ---------- BRAND NEW 30 year ROOF ------------ NEWLY REFINISHED OAK HARDWOOD floors throughout

    Douglas McVicker Suburban Investment Realty

    273 Pine Grove Rd, Middletown, NY 10940
  • 594 County Route 22, Middletown, NY 10940

    $599,999 Sold Aug 26, 2025

    • 3,283 Sq Ft
    • $183/SF
    • 74 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2016

    594 County Route 22, Middletown, NY 10940

    MINISINK SCHOOLS - WORK FROM HOME AND HAVE ROOM FOR EXTENDED FAMILY - Nestled at the end of a long driveway is this spacious four-bedroom, five-bathroom home situated on just under four spacious acres. It is absolutely perfect for multi-generational living, offering a separate in-law suite with a kitchenette and bathroom. This home features not one, but TWO primary suites, one located on the

    Courtney Popowick Rita Levine Real Estate

    594 County Route 22, Middletown, NY 10940
  • 7 Manhattan Ave, Middletown, NY 10940
    7 Manhattan Ave, Middletown, NY 10940
    7 Manhattan Ave, Middletown, NY 10940
    /32

    $369,999 Pending

    • 3 Beds
    • 1 Bath
    • 1,550 Sq Ft

    7 Manhattan Ave, Middletown, NY 10940

    Discover the perfect blend of comfort and convenience in this delightful 3-bedroom, 1-bathroom ranch-style home located at 7 Manhattan Ave .This charming residence nestled on a quiet tree lined street offers a welcoming atmosphere and is ideal for both first-time buyers and those looking for an amazing value .The home has been maintained well by the owner and has many recent upgrades and updates

    Darnell Williams R New York

    7 Manhattan Ave, Middletown, NY 10940
  • 1 Lindentree Ln, Middletown, NY 10940

    $465,000 Sold Aug 25, 2025

    • 1,781 Sq Ft
    • $261/SF
    • 35 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2017

    1 Lindentree Ln, Middletown, NY 10940

    Welcome to easy living in the popular Maple Fields community! This spacious 3-bedroom, 3.5-bath end-unit condo offers 2,484 square feet of comfort and convenience, including a finished basement. Step inside to find high ceilings, granite countertops, and a bright, open feel throughout. The primary bedroom features vaulted ceilings, and the basement is perfect for a home office, gym, or hangout

    Katheryn DeClerck Howard Hanna Rand Realty

    1 Lindentree Ln, Middletown, NY 10940
  • 26 Kyleigh Way, Middletown, NY 10940
    26 Kyleigh Way, Middletown, NY 10940
    26 Kyleigh Way, Middletown, NY 10940
    /34

    $599,999 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,188 Sq Ft

    26 Kyleigh Way, Middletown, NY 10940

    Welcome to this stunning, 5-year-young home located in the desirable Sunrise Hills development.This beautifully maintained residence offers 4 spacious bedrooms, 3 full bathrooms, and 1 half bathroom. The grand cathedral entryway features an elegant chandelier that can be admired from both inside and out, highlighting the top landing of the staircase. The large fourth bedroom is currently set

    Delroy Smith List 4 Less Realty

    26 Kyleigh Way, Middletown, NY 10940
  • 6 Whitman Ct, Middletown, NY 10941

    $295,000 Sold Aug 25, 2025

    • 1,512 Sq Ft
    • $195/SF
    • 28 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1975

    6 Whitman Ct, Middletown, NY 10941

    Come to see this spacious townhouse in the Town of Wallkill, featuring 3 bedrooms, 1.5 baths, oak floor, eat-in kitchen, stainless appliances, walk-in closet, and private backyard. NO hoa, commuter friendly, Pine Bush School, minutes to school, shopping, restaurant, highways. Tax included the star savings.

    Gen Cheung River Realty Services, Inc.

    6 Whitman Ct, Middletown, NY 10941
  • 8 Ebury Mews, Middletown, NY 10940
    8 Ebury Mews, Middletown, NY 10940
    8 Ebury Mews, 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
  • 25 Euclid Ave, Middletown, NY 10940

    $325,000 Sold Aug 25, 2025

    • 1,680 Sq Ft
    • $193/SF
    • 36 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1958

    25 Euclid Ave, Middletown, NY 10940

    Welcome home to 25 Euclid Ave located in the heart of Middletown, NY! This charming 3-bedroom, 1.5-bath ranch offers a welcoming and comfortable living space. The main level features gleaming hardwood floors that enhance the natural light flowing throughout. The eat-in kitchen provides ample cabinet space, perfect for all your culinary needs. The full basement is a versatile area, waiting for

    Maria Sairrino Cronin & Company Real Estate

    25 Euclid Ave, Middletown, NY 10940
  • 580 van Burenville Rd, Middletown, NY 10940
    580 van Burenville Rd, Middletown, NY 10940
    /2

    $299,900 Pending

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    580 van Burenville Rd, Middletown, NY 10940

    Welcome to 580 Van Burenville Rd.

    Valerie Jewis Keller Williams Hudson Valley

    580 van Burenville Rd, Middletown, NY 10940
  • 23 Woodlake Dr, Middletown, NY 10940

    $325,000 Sold Aug 24, 2025

    • 1,460 Sq Ft
    • $223/SF
    • 32 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1989

    23 Woodlake Dr, Middletown, NY 10940

    Welcome to the Spring Hollow Community. One of the few complexes that checks off all the boxes! This community offers a private pool, clubhouse and a pond and YES, it's an end unit! The location is centrally located to all shopping and major commuter highways. This home offers laminate flooring and updated kitchen with tiled back splash, eat in kitchen area as well as a formal dining area with

    Pedro Garcia Curasi Realty, Inc.

    23 Woodlake Dr, Middletown, NY 10940
  • 111 Apple Lane Dr, Middletown, NY 10940
    111 Apple Lane Dr, Middletown, NY 10940
    111 Apple Lane Dr, Middletown, NY 10940
    /28

    $305,000 Pending

    • 2 Beds
    • 1.5 Baths
    • 1,150 Sq Ft

    111 Apple Lane Dr, Middletown, NY 10940

    Picked just for you is this adorable home on Apple Lane! From the moment you walk in, you’ll be greeted by a delightful blast from the past — knotty pine paneling, hardwood floors and an original kitchen complete with metal cabinets and whimsical upper metal cupboards with sliding glass doors that scream mid-century character. Whether you’re a fan of retro style or ready to put your modern touch

    Patricia Sassi RE/MAX Benchmark Realty Group

    111 Apple Lane Dr, Middletown, NY 10940
  • 374 Concord Ln, Middletown, NY 10940

    $218,700 Sold Aug 22, 2025

    • 924 Sq Ft
    • $237/SF
    • 111 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1989

    374 Concord Ln, Middletown, NY 10940

    Experience the perfect blend of style and comfort in this newly renovated 2-bedroom, 2-bathroom condo. Freshly painted and thoughtfully upgraded, this stunning unit features newly upgraded bathrooms, kitchen with modern appliances and a private balcony overlooking a serene, peaceful view—ideal for relaxation. Situated in the most sought-after location within the community, this home offers

    Heather Martin United RE Hudson Valley Edge

    374 Concord Ln, Middletown, NY 10940
  • 143 N Beacon St, Middletown, NY 10940
    143 N Beacon St, Middletown, NY 10940
    143 N Beacon St, Middletown, NY 10940
    /26

    $295,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,264 Sq Ft

    143 N Beacon St, Middletown, NY 10940

    This well built and move-in ready home is ready for your updates and fine touches. The first floor includes an eat-in kitchen, formal dining room and living room. A finished room off the kitchen with access to the landscaped rear yard can be improved to include a kitchen pantry, laundry room and bathroom. Upstairs off the spacious landing you'll find three rooms and a full bath. Both the attic

    Michael Stasi Corcoran Country Living

    143 N Beacon St, Middletown, NY 10940
  • 29 Lafayette Ave, Middletown, NY 10940

    $310,000 Sold Aug 22, 2025

    • 1,132 Sq Ft
    • $274/SF
    • 27 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1928

    29 Lafayette Ave, Middletown, NY 10940

    Perfect Starter Home or Investment Opportunity!Welcome to this charming 3-bedroom, 1-bath home—ideal for first-time homebuyers, savvy investors, or anyone looking for a fixer-upper with great potential. Step inside to find a spacious living room perfect for relaxing or entertaining, a dedicated dining room for family meals, and a bright kitchen ready for your personal

    Waldina Almazan RE/MAX Benchmark Realty Group

    29 Lafayette Ave, Middletown, NY 10940
  • 841 Howells Turnpike, Middletown, NY 10940
    841 Howells Turnpike, Middletown, NY 10940
    841 Howells Turnpike, Middletown, NY 10940
    /43

    $535,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    841 Howells Turnpike, Middletown, NY 10940

    Welcome to 841 Howells Turnpike – Your Private Retreat in the Pine Bush School District Set on 1.3 park-like acres, 3-bedroom, 2.5-bath contemporary colonial offers a blend of timeless charm, spacious living, and total privacy all nestled in the heart of the Hudson Valley and just 5 miles from the train station to NYC. As you arrive, a long paved driveway winds through a wooded approach, passing

    Alyse Toffel Keller Williams Hudson Valley

    841 Howells Turnpike, Middletown, NY 10940
  • 19 Woodrose Ct, Middletown, NY 10940

    $475,000 Sold Aug 21, 2025

    • 2,890 Sq Ft
    • $164/SF
    • 31 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2020

    19 Woodrose Ct, Middletown, NY 10940

    Welcome to Highrose Ridge! This home offers 2890 sq ft of efficient space. Barely broken in at five years young, the home is Turn-key & Move-In Ready. This end unit is inviting from the moment you walk through the entrance, where you are greeted with an open floor plan with Formal Living Rm, Dining Area, Powder Rm, Oak Hardwood Floors and steps out to a semi private rear yard. The EIK is open

    Debbie Goldstein Howard Hanna Rand Realty

    19 Woodrose Ct, Middletown, NY 10940
  • 34 Feiertag Rd, Middletown, NY 10941
    34 Feiertag Rd, Middletown, NY 10941
    34 Feiertag Rd, Middletown, NY 10941
    /28

    $598,000 Pending

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

    34 Feiertag Rd, Middletown, NY 10941

    PRICE REDUCTION.........Let your dreams begin with large colonial home located on a Cul-de-Sac in the Pine Bush School District. Step inside to a large and open foyer with high ceilings which creates a welcoming atmosphere. The main level features a formal dining room, den/office, cozy family room with woodburning fireplace, open eat in kitchen with breakfast area, full bath and enclosed screened

    Julianna Cotthaus 1st Independent Realty Grp

    34 Feiertag Rd, Middletown, NY 10941
  • 3 Mulberry Run, Middletown, NY 10941

    $737,500 Sold Aug 21, 2025

    • 2,929 Sq Ft
    • $252/SF
    • 169 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2020

    3 Mulberry Run, Middletown, NY 10941

    Proved to sell!! Allow us to reintroduce this stunning 5-year-young home, now refreshed with beautiful new spring photos and video! Waiting for its new owners, the Princeton Model in Heritage Hills features a sun-filled open layout with hardwood floors, granite countertops, and a chef’s kitchen with island, walk-in pantry, and eat-in space. Your main level offers a private study, formal dining,

    Michelle Getty HVG Realty, Inc.

    3 Mulberry Run, Middletown, NY 10941
  • 1 Chancery Mews, Middletown, NY 10940
    1 Chancery Mews, Middletown, NY 10940
    1 Chancery Mews, Middletown, NY 10940
    /14

    $349,000 Pending

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

    1 Chancery Mews, Middletown, NY 10940

    Welcome to this spacious and well-maintained contemporary-style home located in the sought-after Canterbury Knolls community. Featuring 3 bedrooms, 2 bathrooms, this home offers comfortable and functional living for today’s modern lifestyle. The inviting living room includes a cozy fireplace, while sliding glass doors lead to a private patio—perfect for entertaining or enjoying peaceful evenings

    Sean Walker Keller Williams Realty

    1 Chancery Mews, Middletown, NY 10940
  • 22 Restorative Ln, Middletown, NY 10940

    $750,000 Sold Aug 21, 2025

    • 2,629 Sq Ft
    • $285/SF
    • 33 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2010

    22 Restorative Ln, Middletown, NY 10940

    Welcome to 22 Restorative Lane – A Private Retreat on 2.9 Acres in Minisink School District. Tucked away on a quiet, half-mile cul-de-sac with beautiful views and complete privacy, this meticulously maintained 4-bedroom, 2.5-bath home offers 3179 sq ft of spacious living—which includes 550 sq ft of finished basement space perfect for a gym and/or media room. Gorgeous full kitchen, with stainless

    Susanne Dermigny Howard Hanna Rand Realty

    22 Restorative Ln, Middletown, NY 10940
  • 77 Prince St, Middletown, NY 10940
    77 Prince St, Middletown, NY 10940
    77 Prince St, Middletown, NY 10940
    /30

    $399,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,245 Sq Ft

    77 Prince St, Middletown, NY 10940

    Welcome to this beautiful well maintained contemporary two story home nestled in the heart of Middletown. Offering you a bright and spacious living room to a formal dining room, a beautiful kitchen, 3 great size bedrooms, 2.5 bathrooms with a full size basement and a car garage. Plus plenty of closets with its laundry room. With its level backyard and great size deck, you will enjoy your time

    Anita S. Cristiano HomeSmart Homes & Estates

    77 Prince St, Middletown, NY 10940
  • 87 Sycamore Dr, Middletown, NY 10940

    $295,000 Sold Aug 21, 2025

    • 1,342 Sq Ft
    • $220/SF
    • 64 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1977

    87 Sycamore Dr, Middletown, NY 10940

    Welcome to this lovely 2-bedroom, 2 full bathrooms, well-kept condo located in the sought-after Clemson Park complex! This 2nd floor unit, one-level floor plan is beautifully maintained and boasts 1342 sq. ft of living space with a master suite with its own full bathroom, an additional bedroom and full bath, laundry room, eat-in kitchen, formal dining area, living room, built-in cabinets in the

    Jacqueline Henry-Thompson Jackie Henry Realty LLC

    87 Sycamore Dr, Middletown, NY 10940
  • 947 Scotchtown Collabar Rd Unit 947-8, Middletown, NY 10941
    947 Scotchtown Collabar Rd Unit 947-8, Middletown, NY 10941
    947 Scotchtown Collabar Rd Unit 947-8, Middletown, NY 10941
    /42

    $499,000 Pending

    • 6 Beds
    • 3.5 Baths
    • 3,714 Sq Ft

    947 Scotchtown Collabar Rd Unit 947-8, Middletown, NY 10941

    Investor Special! This unique opportunity includes multiple dwellings across three parcels — 947 Scotchtown Collabar Road, 427 Union School Road, and a deeded vacant lot on County Route 47 (SWIS 332600 SBL 27-1-8.11, Town of Crawford, 1.60 acres). With expansive potential and flexible use options, this compound offers the chance to restore, rebuild, or re-imagine the entire property portfolio.

    Stephen Zondorak Astor Lane Realty

    947 Scotchtown Collabar Rd Unit 947-8, Middletown, NY 10941
  • 20 Columbia Ave, Middletown, NY 10940

    $290,000 Sold Aug 20, 2025

    • 1,232 Sq Ft
    • $235/SF
    • 3 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1920

    20 Columbia Ave, Middletown, NY 10940

    Step across the sun-warmed front walk, swing open the original door, and feel possibility bloom.Beneath time-worn rugs, early-century hardwood floors wait for their first gleam of daylight. Sunshine pours through tall windows, skimming vintage trim and setting off the solid brass door hardware that clicks shut with reassuring certainty. A welcoming living room flows into a private dining

    Brian Caplicki Keller Williams Hudson Valley

    20 Columbia Ave, Middletown, NY 10940

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