39

Middletown, NY Homes for Sale under $800,000

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  • /46

    $574,900

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,432 Sq Ft

    180 Mt Orange Rd, Middletown, NY 10940

    The primary suite alone tells you what kind of home this is. A vaulted cathedral ceiling overhead, a spa-style bath built around a deep soaking tub, and proportions that hold a quiet hour at the end of a long day the way a private retreat is supposed to. It is the kind of room that quietly redefines what you expect a ranch to feel like. By the time the water is running, the day has already

    Agent Photo

    Brian Caplicki

    KW Hudson Valley United

    180 Mt Orange Rd, Middletown, NY 10940
  • /50

    $599,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 3,080 Sq Ft

    179 Reservoir Rd, Middletown, NY 10940

    Warmth, comfort & space in the Hudson Valley. Welcome home to this spacious Colonial on 2.8 acres offering 3–4 bedrooms, 2 full baths, and a detached 2-car garage with oversized loft. The heart of the home is the large family room — cathedral ceilings, a stunning stone fireplace, and beautiful hardwood floors — the perfect place to gather. The private second-floor primary suite has its own full

    Agent Photo

    Dulce M Ferrera

    KW Hudson Valley United

    179 Reservoir Rd, Middletown, NY 10940
  • /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
  • /24

    $587,000

    $12K 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
  • /13

    $550,000

    $10K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 1,911 Sq Ft

    35 Dogwood Dr, Middletown, NY 10940

    Just pack your bags and move in. Spacious, Comfortable and Cozy 5 bedroom 1 family house for sale. This house features 4 Bedrooms and 2 bathrooms on the upper level with a walk in closet and a bathroom in the master bedroom. The first features a 1/2 bath, renovated kitchen, separate living and dinning rooms and a walkout deck. The ground floor features a 2 car garage, finished basement with 1

    Lenworth Brisco Keller Williams Realty NYC Grp

    35 Dogwood Dr, Middletown, NY 10940
  • /38

    $539,900

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,694 Sq Ft

    181 Stony Ford Rd, Middletown, NY 10941

    Set on 6.7 private acres in Middletown, this 3-bedroom, 2-bath, 1,694 sq ft home offers the perfect blend of comfort and outdoor living. Enjoy your own private retreat featuring quad trails, river access ideal for fishing, and abundant wildlife for hunting or nature watching. The outdoor space is designed for entertaining and relaxation with a fire pit area and a spacious two-tier deck complete

    Rana Ali eXp Realty

    181 Stony Ford Rd, Middletown, NY 10941
  • /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
  • /37

    $535,000

    • 4 Beds
    • 4 Baths
    • 2,088 Sq Ft

    19 Randall Terrace, Middletown, NY 10940

    STUNNING Colonial located in a quiet neighborhood of Middletown minutes from OCC. This home is in mint condition with the upgrades it offers. Enter into an oversized living room with a fireplace that leads to a formal dining room & gorgeous new kitchen. This modern eat in kitchen features self closing cabinets, granite countertops, backsplash & beautiful fresh out the box stainless steel

    Sandra Arnez KW Hudson Valley United

    19 Randall Terrace, 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
  • /32

    $599,000

    • 3 Beds
    • 2.5 Baths
    • 2,929 Sq Ft

    1 Parkview Dr, Middletown, NY 10940

    Welcome to 1 Parkview Dr. in beautiful Presidential Park in Middletown, NY. Located on a corner lot, this expanded raised ranch shines. Gleaming hardwood floors and spacious room size are only some if it's great features. Eat in kitchen boasts an atrium that looks out to its lovely landscaped backyard. Spend time in this space and you'll feel like you're on vacation. Beautiful inground pool is

    Marie Altieri Howard Hanna Rand Realty

    1 Parkview Dr, Middletown, NY 10940
  • /36

    $599,900

    • 6 Beds
    • 3.5 Baths
    • 2,948 Sq Ft

    669 Mountain Rd, Middletown, NY 10940

    Country Escape of 6 spacious bedrooms offers space, privacy, and a serene setting on 3.38 acres. Just about 75 miles from New York City, it’s close enough for convenient weekend escapes yet far enough to feel like a true retreat feels like a private estate—perfect for those seeking a refined escape from city life A grand foyer opens to a bright, airy layout with high ceilings, large windows, and

    Michelle Gruberger Real Estate Circuit Inc

    669 Mountain 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
  • /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
  • /46

    $550,000

    • 4 Beds
    • 2.5 Baths
    • 2,069 Sq Ft

    16 Houston Ext Ave, Middletown, NY 10940

    Welcome to this beautiful, young Colonial, built in 2016 and ideally situated on a quiet street of newer homes in Middletown. Offering 4 spacious bedrooms and 2.5 bathrooms, this move-in-ready property seamlessly combines modern convenience with timeless style. The main level features gleaming hardwood floors, complemented by durable tile in the kitchen, half bath, and garage entry. Designed for

    Karleen Jedziniak Howard Hanna Rand Realty

    16 Houston Ext Ave, Middletown, NY 10940
  • /58

    $575,000

    • 12 Beds
    • 10 Baths
    • 5,004 Sq Ft

    5 Wawayanda Place, Middletown, NY 10940

    CASH ONLY - Totally renovated large home with 12 bedrooms, 8 of them being suites with their own full bathroom. 10 full bathrooms total. Home also features game room, large dining area, living room, spacious eat in kitchen with stainless appliances & island, laundry off the kitchen, large fenced patio & inground pool. Conveniently located around Orange County Community College, tennis & skate and

    Jamie Sittner Find Advisors

    5 Wawayanda Place, Middletown, NY 10940
  • /29

    $550,000

    • 4 Beds
    • 3 Baths
    • 2,018 Sq Ft

    13 Avenue B, Middletown, NY 10940

    THIS BI LEVEL FEATURES 2018 SQUARE FEET, WITH AN OPEN CONCEPT, VAULTED CEILINGS, MASTER SUITE, THREE ADDITIONAL BEDROOMS WITH TWO MORE FULL BATHS, HARD WOOD FLOORING ON THE SECOND LEVEL, KITCHEN WITH ISLAND, GRANITE COUNTER TOP, STAINLESS STEEL APPLIANCES, TWO CAR ATTACHED GARAGE WITH AN EXTENDED DRIVEWAY TO ACCOMODATE MANY MORE CARS

    Christopher Hosten Charles Rutenberg Realty, Inc.

    13 Avenue B, Middletown, NY 10940
  • /46

    $515,000

    Open Fri 4PM - 6PM
    • 4 Beds
    • 1.5 Baths
    • 1,732 Sq Ft

    23 Marcy Ln, Middletown, NY 10941

    Welcome to this beautifully renovated raised ranch in the desirable Scotchtown neighborhood. Offering over 1,700 square feet of living space, this move-in-ready home features 4 spacious bedrooms and 2 updated bathrooms. The bright main level offers a spacious L-shaped living and dining room filled with natural light, along with a beautifully renovated kitchen featuring brand-new stainless steel

    Dennis Aboagye Keller Williams Realty Group

    23 Marcy Ln, Middletown, NY 10941
  • /19

    $575,000

    • 3 Beds
    • 3 Baths
    • 5,157 Sq Ft

    20 John St, Middletown, NY 10940

    For Sale: Income-Producing Mixed-Use Building in Prime Downtown Middletown Take advantage of this exceptional opportunity to own a versatile, income-generating property in the heart of Downtown Middletown—an up-and-coming city with a pro-business government and strong growth potential. Property Overview: First Floor:Spacious 2,000 sq. ft. commercial space, currently used as a retail store,

    Jonathon Lee KW Hudson Valley United

    20 John St, 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
  • /6

    $599,000

    $31K PRICE DROP
    • 10 Beds
    • 4 Baths

    309-317 E Main St Unit 309, Middletown, NY 10940

    Welcome to this beautiful two-family home located on E Main Street! Perfect for owner-occupants, investors, or extended family living, this spacious property offers incredible flexibility and charm. One unit features 6 bedrooms, while the second unit offers 4 bedrooms, providing plenty of spac. Both units have separate front and side entrances for added privacy and convenience. The property sits

    Betzaida Vericain Q Home Sales

    309-317 E Main St Unit 309, 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
  • /49

    $529,900

    • 3 Beds
    • 2.5 Baths
    • 2,504 Sq Ft

    37-39 Wisner Ave, Middletown, NY 10940

    Welcome to this beautifully remodeled 3-4 bedroom, 3-bath Colonial situated on a rare double lot at 37-39 Wisner Avenue in Middletown. Move-in ready and thoughtfully updated, this spacious home offers modern comforts, flexible living space, and exceptional outdoor parking and yard areas rarely found within the city. The main level features a generously sized living room, formal dining room, and a

    Jonathon Lee KW Hudson Valley United

    37-39 Wisner Ave, 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
  • /37

    $549,000

    • 4 Beds
    • 2.5 Baths
    • 2,680 Sq Ft

    25 Georges Rd, Middletown, NY 10941

    Looking for a spacious Colonial in Middletown, NY, with room to grow and an easy NYC commute? Welcome to 25 Georges Road, a 4-bedroom, 2 full baths, and a half bath home offering 2,680 square feet of living space on a quiet residential street. Built in 1985, this home features a classic center hall layout, generous living areas, a brick fireplace, a large eat-in kitchen with abundant cabinetry, a

    Matthew Gibbs KW Hudson Valley United

    25 Georges Rd, Middletown, NY 10941
  • /21

    $560,000

    • 4 Beds
    • 3 Baths
    • 2,162 Sq Ft

    77 Upper Rd, Middletown, NY 10940

    This beautiful ranch-style property is ready to move in. Amazing upgrades were made to this home with beautiful hardwood floors, 4 bedrooms, 3 bathrooms, a huge finished basement with 3 additional rooms for storage or home office, and it also has space for a personal gym with access to an amazing backyard that features a beautiful above-ground pool, a tennis court, volleyball court, or basketball

    Yajaira Silva Madison Allied LLC

    77 Upper Rd, Middletown, NY 10940
  • /42

    $575,000

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,053 Sq Ft

    45 Randall Heights, Middletown, NY 10940

    PRESIDENTIAL HEIGHTS welcomes you to make this LUXURY CONTEMPORARY home yours today! Set in the highly desirable Presidential Heights neighborhood, known for its beautiful homes, peaceful atmosphere, and close proximity to everyday essentials. A large wrap around blacktopped driveway along with paver stone walkway leads you inside this newly remodeled gem. Discover an incredible blend of space,

    Sandra Arnez KW Hudson Valley United

    45 Randall Heights, 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
  • /24

    $555,000

    $24K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,202 Sq Ft

    29 Murray Rd, Middletown, NY 10940

    3 PRIVATE ACRES + ULTIMATE VERSATILITY + POSSIBLE INCOME POTENTIAL = A RARE MIDDLETOWN OPPORTUNITY Set on 3 serene, wooded acres, this beautifully maintained raised ranch offers an expansive 2,202 sq. ft. of living space designed with a unique, highly adaptable layout that can help with your financial goals or adapt to your lifestyle. The main level features a bright open-concept main floor with

    Regina Lombardo KW Hudson Valley United

    29 Murray Rd, Middletown, NY 10940
  • /22

    $560,000

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,332 Sq Ft

    2078 Route 6, Middletown, NY 10940

    Welcome to this beautifully maintained contemporary bi-level home set on 2.2 private acres in the scenic countryside of Orange County. Built in 2015, this exceptional residence combines modern comfort with peaceful surroundings, offering the perfect balance of privacy and convenience. The impressive entryway welcomes you with soaring cathedral ceilings, abundant natural light, and an open, airy

    Shiva Kalipersad Anthony Napolitano Homes

    2078 Route 6, Middletown, NY 10940
  • /50

    $599,900

    • 4 Beds
    • 1.5 Baths
    • 3,280 Sq Ft

    22 Camp Orange Rd, Middletown, NY 10941

    Cherished through generations and lovingly maintained by its owners, this remarkable circa home is ready for its next chapter. Set on 3.6 beautifully level acres in the Valley Central School District, the property offers the perfect blend of historic character, functional space, and country charm. As you approach, the care and pride of ownership are immediately evident. A welcoming front porch

    Rosalie Cook Weichert Realtors

    22 Camp Orange Rd, Middletown, NY 10941
  • /50

    $520,000

    • 3 Beds
    • 2.5 Baths
    • 2,567 Sq Ft

    29 Avoncroft Ln, Middletown, NY 10940

    Welcome to 29 Avon Croft Lane, a beautifully maintained home offering privacy, comfort, and convenience in a desirable Middletown location. Nestled among mature trees and natural surroundings, this property provides a peaceful and secluded setting while remaining close to shopping, dining, schools, and major commuter routes. Step inside to discover spacious rooms, hardwood floors, elegant crown

    Gail Rachlin KW Hudson Valley United

    29 Avoncroft Ln, Middletown, NY 10940
  • /49

    $599,900

    • 4 Beds
    • 4 Baths
    • 3,208 Sq Ft

    24 Mud Mills Rd, Middletown, NY 10940

    NOT EVERY HOME IS DESIGNED WITH TOMORROW IN MIND. THIS ONE WAS. Fully designed with intention and foresight, this unique 4-bedroom colonial offers a rare level of flexibility, functionality and comfort that can adapt as life needs evolve. From the moment you arrive, you'll appreciate this home's flexible floor plan and the endless possibilities it provides. Generous living spaces and a

    Patricia Sassi RE/MAX Benchmark Realty Group

    24 Mud Mills Rd, Middletown, NY 10940
  • /45

    $525,000

    Open Sun 4PM - 6PM $25K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,344 Sq Ft

    1 Hulse St, Middletown, NY 10940

    "NEW CONSTRUCTION!" Stunning corner-lot home in a calm suburban setting with beautiful mountain views — offering space, upgrades, and thoughtful design throughout. This impressive property offers approximately 2,344 sq ft of living space and features 9-ft ceilings on the main level and 8-ft ceilings upstairs, enhancing the open and airy layout. The upgraded 400+ sq ft kitchen is a true highlight,

    Chaim Friedman KW Hudson Valley United

    1 Hulse St, 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%
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