21

Middletown, NY Homes for Sale under $900,000

Section Image Section Image
  • /50

    $895,000

    Open Sun 1PM - 3PM
    • 4 Beds
    • 2.5 Baths
    • 3,296 Sq Ft

    411 Mt Joy Rd, Middletown, NY 10941

    Space, privacy, and thoughtful design come together at this well-maintained 4-bedroom, 2.5-bath Colonial, built in 2005, offers 3,296 sq ft of living space on 11.7 private acres—giving you room to breathe while staying conveniently close to everything Middletown has to offer.Step inside and you'll immediately notice the 9-foot ceilings that elevate every room with an airy, open feel. The main

    Agent Photo

    Donna Reese

    KW Hudson Valley United

    411 Mt Joy Rd, Middletown, NY 10941
  • /44

    $669,000

    • 3 Beds
    • 3 Baths
    • 3,225 Sq Ft

    23 Orange Terrace, Middletown, NY 10940

    Experience a one-of-a-kind custom-built A-Frame that blends rustic charm with modern luxury. Nestled on a quiet street in the city, this stunning home commands attention with its reflective tinted windows, dramatic architecture, and incredible curb appeal. Seller is offering a $20,000 concession to the buyer with an acceptable offer. Designed for both entertaining and everyday living, the

    Agent Photo

    Joao Rodrigues

    Preferred Properties Real Esta

    23 Orange Terrace, Middletown, NY 10940
  • /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
  • /49

    $799,000

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

    3 Truman Ct, Middletown, NY 10940

    Step into 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 inviting focal points across multiple living

    Dominick Tufano RE/MAX Benchmark Realty Group

    3 Truman Ct, Middletown, NY 10940
  • /42

    $639,000

    $40K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,680 Sq Ft

    481 Dosen Rd, Middletown, NY 10940

    ABSOLUTELY GORGEOUS!!! MUST SEE!! QUALITY BUILT WITH BRAND NEW ADDITION AND BRAND NEW DETACHED POLE BARN!!! OVER 7 ACRES !!! 481 Dosen Road offers a rare combination of quality construction, privacy, and usable space, set on 7.4 peaceful acres. This custom-built Lok-N-Logs log home was thoughtfully designed to blend the character of a true log cabin with the comforts needed for everyday living.

    Frank Muccari Cronin & Company Real Estate

    481 Dosen Rd, Middletown, NY 10940
  • /30

    $844,000

    $5K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 3,764 Sq Ft

    238 S Centerville Rd, Middletown, NY 10940

    Spacious Country Retreat on 22.6 Acres in Minisink Valley School District This exceptional property offers privacy, comfort, and extensive amenities set on 22.6 picturesque acres. The master bedroom and bathroom were updated in 2016, complemented by a wet bar in the family room—perfect for entertaining. The home features three fireplaces and a wood stove, creating warmth and character throughout.

    Linda VanDeWeert BHG Real Estate Green Team

    238 S Centerville Rd, Middletown, NY 10940
  • /38

    $899,000

    • 5 Beds
    • 4.5 Baths
    • 4,200 Sq Ft

    255 Howells Rd, Middletown, NY 10940

    Enter the gates of this remarkable 36.8-acre estate to discover a distinguished 5-bedroom, 5-bathroom residence offering 4,200 square feet of living space. The property includes a substantial two-story post-and-beam barn with horse stalls, multiple wells, and an additional hay barn—ideal for equestrian or agricultural use. A serene natural pond and a mix of rolling pastures and wooded areas

    Jonathon Lee KW Hudson Valley United

    255 Howells Rd, Middletown, NY 10940
  • /33

    $635,000

    $40K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,481 Sq Ft

    5 Decker Dr, Middletown, NY 10940

    Charming Farmhouse Retreat on 2.9 Acres! Nestled on a quiet country road in the Town of Greenville and located within the desirable Minisink Valley Central School District. This beautiful farmhouse-style home offers the perfect blend of comfort, charm, and country living. Inviting home features 3 bedrooms and 2.5 baths with attractive Pergo wood flooring throughout the downstairs, while upstairs

    Dominick Tufano RE/MAX Benchmark Realty Group

    5 Decker Dr, Middletown, NY 10940
  • /50

    $899,000

    $40K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,894 Sq Ft

    114 Last Rd, Middletown, NY 10941

    Distinctive 11-Acre Country Retreat - More than a home, this property delivers a lifestyle defined by space, privacy, and ease. Set across two parcels totaling 11.1 acres, this distinctive Cape Cod combines thoughtful design and easy, everyday living. From the expansive covered front porch to the farmhouse-style entry, the home immediately feels airy and inviting. Inside, the home balances warmth

    Michelle Genatempo Howard Hanna Rand Realty

    114 Last Rd, Middletown, NY 10941
  • /17

    $629,000

    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft

    744 Mt Hope Rd, Middletown, NY 10940

    Welcome to this stunning new Colonial home, currently under construction and set on approximately 3 beautiful acres in the desirable Town of Wallkill. Offering approximately 2,600 square feet of finished living space, including a finished basement, this spacious home features 4 bedrooms, 3 full bathrooms, and a one-car garage. The inviting open-concept design showcases gleaming hardwood floors

    Anita S. Cristiano HomeSmart Homes & Estates

    744 Mt Hope Rd, Middletown, NY 10940
  • /38

    $699,000

    $30K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,284 Sq Ft

    168 Pine Grove Rd, Middletown, NY 10940

    Update - priced to sell! Imagine waking up surrounded by three private acres while still being just minutes from shopping and major commuter routes. This newly built colonial offers the peace of country living without sacrificing convenience. The open-concept kitchen, oversized island, fireplace, spacious primary suite and unfinished basement provide room to grow while giving buyers the

    Leeshai Lemish Panorama Realty

    168 Pine Grove Rd, Middletown, NY 10940
  • /8

    $660,000

    $40K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 2,040 Sq Ft

    2467 Route 302, Middletown, NY 10941

    Excellent location and property seeking a savvy investor. Pine Bush schools, fully leased near Highway and less than 5 miles to train. Close to shopping too. Hurry to see before it is gone.

    Myrna Lattore eRealty Advisors, Inc

    2467 Route 302, Middletown, NY 10941
  • /44

    $799,999

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    TBD Brook Rd, Middletown, NY 10941

    New Construction LUXURY HOME in Valley Central Schools outside of SCOTCHTOWN! "Choose Your Finishes" on this Stunning 3,000 sq. ft. modern Colonial privately set atop a scenic 5-acre wooded lot offering privacy and natural beauty. Conveniently located 5-10 minutes to Middletown, Pine Bush, and Montgomery. The main level features a spacious open-concept floor plan with 9-foot ceilings, hardwood

    Philip Barnao eXp Realty

    TBD Brook Rd, Middletown, NY 10941
  • /43

    $745,000

    $670K PRICE INCREASE
    • 4 Beds
    • 2 Baths
    • 1,395 Sq Ft

    903 Rd, Middletown, NY 12421

    Rare Catskills Investment Retreat — Pool, Views & Proven Short-Term Rental Income. One of the few properties in the Catskills with a private pool and the income to match, this turnkey 4-bedroom, 2-bath mountain retreat on 5+ acres offers a competitive edge that most area listings simply cannot. The private pool extends peak demand well beyond the winter ski season, attracting premium summer

    Ashley O'Malley Listing by Jewett and Jewett LLC

    903 Rd, Middletown, NY 12421
  • /41

    $749,900

    • 4 Beds
    • 2.5 Baths
    • 2,906 Sq Ft

    512 County Route 49, Middletown, NY 10940

    Welcome to this stunning, meticulously maintained Chesterfield Colonial offering breathtaking views, exceptional updates, and true move-in-ready condition. From the moment you enter the impressive two-story foyer, you'll appreciate the bright, open-concept design and abundance of natural light streaming through every window. The spacious main living areas are perfect for both everyday living and

    Jonathon Lee KW Hudson Valley United

    512 County Route 49, Middletown, NY 10940
  • /18

    $695,000

    $55K PRICE DROP
    • 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
  • /50

    $625,000

    • 3 Beds
    • 2.5 Baths
    • 2,548 Sq Ft

    8 Green Ct, Middletown, NY 10940

    Welcome to this well-maintained 3-level townhome in The Fairways, a gated community conveniently located next to a golf course and just minutes from major highways, Garnet Health Medical Center, shopping, restaurants, and everyday conveniences. This home offers a 2-car garage, a finished lower level with direct garage access, and a functional floor plan designed for comfortable everyday living.

    Jie Liu KW Hudson Valley United

    8 Green Ct, Middletown, NY 10940
  • /41

    $699,000

    $130K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,340 Sq Ft

    571 Route 17m, Middletown, NY 10940

    Steeped in character and timeless appeal, this 1930 Colonial invites you in with its striking stone facade and a graceful partial wrap-around porch—an ideal spot to enjoy quiet mornings or unwind at the end of the day. Inside, the home blends classic craftsmanship with modern comfort, featuring rich wooden floors that flow seamlessly throughout the main level.The first floor offers a warm and

    Angela Murphy BHG Real Estate Green Team

    571 Route 17m, Middletown, NY 10940
  • /6

    $799,000

    • 4 Beds
    • 3.5 Baths
    • 2,696 Sq Ft

    1 Winters Ln, Middletown, NY 10940

    Welcome to your dream home! This stunning new construction craftsman-style home is now being built on Lot 1 of the coveted Lane Meadow Farm subdivision, located in the Town of Mamakating, Sullivan County, NY. Enjoy the serenity and natural beauty of one of Sullivan County's newest and most sought-after neighborhoods, where peaceful country living meets exceptional craftsmanship. Featuring

    Jacob Silberstein Parcel Realty LLC

    1 Winters Ln, Middletown, NY 10940
  • /49

    $850,000

    $50K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 4,090 Sq Ft

    464 Union School Rd, Middletown, NY 10941

    Nestled on a private 5.1-acre property, this custom contemporary Cape-style home offers the perfect balance of luxury, comfort, and natural beauty. Thoughtfully designed with refined finishes and exceptional living spaces, this residence creates an inviting retreat while still being close to the many attractions of the Hudson Valley. Step inside to discover a bright and spacious main level

    Colin Seitz RE/MAX Benchmark Realty Group

    464 Union School Rd, Middletown, NY 10941
  • /45

    $825,000

    Open Wed 6PM - 7:30PM
    • 4 Beds
    • 2.5 Baths
    • 3,276 Sq Ft

    34 Stapleton Ct, Middletown, NY 10940

    This stunning four-bedroom Colonial is nestled on 1.3 acres at the end of a peaceful cul-de-sac, backing up to the scenic Hunter Nature Preserve. Enjoy relaxing evenings on the spacious rocking chair front porch. The updated kitchen features beautiful granite countertops and a custom backsplash, perfect for culinary enthusiasts. The expansive Great Room is ideal for celebrations, entertaining

    Annie Hansen Howard Hanna Rand Realty

    34 Stapleton Ct, Middletown, NY 10940

Home Price Trends

Median Sale Price
$401,500
Median Single Family Sale Price
$425,000
Median Townhouse Sale Price
$437,500
Median 2 Bedroom Sale Price
$302,500
Median 1 Bedroom Sale Price
$170,000
Average Price Per Sq Ft
$250
Number of Homes for Sale
132
Last 12 months Home Sales
456
Months of Supply
3.50
Median List Price
$399,999
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
How to Buy a Home How to Finance a Home How to Sell a Home