Middletown New York homes for sale starting at Fifty Thousand Dollars

$259,900 - Middletown, NY

80 Beattie Avenue Middletown, NY - Here on freshly paved Beattie Ave in Middletown, you'll find this 1920 two story style. The home has three bedrooms, a full bath, kitchen, living room- dining room combo, as well as a walk-up attic and full unfinished basement. Outside there is a covered front porch, small fenced yard and a detached two car garage. The home is in overall sound condition, but will need enough repairs that it may preclude the use of some types of financing.

$259,000 - Middletown, NY

1375 Dimmick Mountain Road Middletown, NY - Versatile Mixed-Use Property with Panoramic views and a Trout Stream as well as a Reliable Long Term Income Seize the opportunity to own a well-maintained mixed-use property featuring a stable, long-term tenant located on 5 bucolic acres in the heart of the Catskills. Built in 1998, this 1,200 sq ft building is currently leasing the first floor (600 sq ft) to the U.S. Postal Service through July 1, 2028, with two additional 5-year renewal options, each including a 10% rent escalation clause—offering a reliable income stream for years to come. A separate entrance leads to a 600 sq ft unfinished second floor, presenting a blank canvas for conversion into a studio apartment, office, or additional rental unit. The property boasts a newly installed roof (2024) and a 4,000 sq ft paved parking area dedicated to tenant use. Nestled alongside the serene Bataviakill trout stream, the land features a level grassed meadow, offering panoramic mountain views. The spacious lot provides ample room to park an RV, place a tiny home, or construct another structure—subject to zoning regulations. Located conveniently between Margaretville and Roxbury, this property offers easy access to outdoor recreation, including fishing in your own trout stream, skiing at Belleayre and Plattekill ski areas, hiking on nearby state trails, and paddling on the Pepacton Reservoir. Whether you're seeking a solid investment with existing income or envisioning further development to maximize the property's potential, this offering combines financial stability with the allure of Catskills living.

$250,000 - Middletown, NY

13 Smith Street Middletown, NY - Looking to add a rental property to your porfolio? This 3 bedroom, 1 bathroom home might be the one. Long term tenant looking to stay. Located in the heart of the city of Middletown. Walking distance to local shops, restaurants, supermarket, park and much more. Located on a one way street with low local traffic. Call today for appoiintment.

$249,999 - Middletown, NY

21 Lake Claire Drive Middletown, NY - Charming Lake Cottage Retreat – 21 Lake Claire Drive, Middletown, NY Nestled among the trees on a quiet hillside, this bright and rustic 2-bedroom, 2-bath lake cottage offers a peaceful retreat with vintage character and natural charm. The vibrant red wood siding, expansive outdoor decking, and tree-lined setting create an inviting atmosphere perfect for weekend getaways or full-time living. Step inside to discover an open and sun-filled layout, highlighted by large windows, exposed beams, and cozy gathering spaces. The home features a wood-burning stove, original wood finishes, and a functional kitchen ready for your personal touch. Outdoor living is a dream here with multiple decks, stone terracing, and garden. Located in a private lake community, you’re just steps from water access, hiking trails, and nature escapes—yet still convenient to town amenities and major roadways. Whether you’re looking for a vacation home, Airbnb potential, or a full-time escape from the ordinary, this hidden gem offers affordable tranquility in the heart of the Hudson Valley. Highlights: 2 Bedrooms / 2 Bath Wood-burning stove and rustic charm Large multi-level deck and hillside stonework Private wooded lot in a lake community Multiple decks and outdoor living areas Close to highways, shopping, and outdoor recreation Investors and cash buyers welcomed.

$249,000 - Middletown, NY

1603 Goshen Turnpike Middletown, NY - This 1850-built home at 1603 Goshen Turnpike is full of potential for investors and flippers. It features wide plank oak floors, a fireplace, and a country kitchen, offering a solid foundation for renovations. With 1,636 sq ft of living space, 2 bedrooms, and 2 bathrooms, this home sits on a 6,991 sq ft lot, providing room for updates and improvements. Central cooling and forced air heating are already in place, making it a great candidate for a profitable flip or rental. Located minutes from schools, shopping, and commuter routes, this home is in a high-demand area. Whether restoring its historic charm or modernizing it, there is plenty of value to unlock. Bring your vision and turn this property into a great investment.

$239,888 - Middletown, NY

218 Concord Lane Middletown, NY - Welcome to this charming first-floor condo located in Buttonwood Hills community! With 2 bedrooms, 2 baths, and a patio, this well-maintained unit offers a galley kitchen, dining area, and living room. Enjoy access to clubhouse amenities and a community poolhouse. Ideal for those seeking convenience and community living.

$239,000 - Middletown, NY

25 Jimal Drive Middletown, NY - This end-unit property, featuring a ground-level setup overlooking the woods, provides a charming, tranquil view an abundance of natural light. The well-designed kitchen area, complemented by a cozy eat-in space with two opposing windows, is ideal for enjoying meals while admiring the scenery. With a compact secondary and a generously sized primary bedroom, condo strikes a harmonious balance between functionality and comfort. It presents an excellent for those seeking a serene retreat with thoughtful design elements.

$235,000 - Middletown, NY

38 Brittany Drive Middletown, NY - Welcome to 38 Brittany Drive, located in a desirable ground-level condo nestled in a quiet, well-maintained community! This two-bedroom, one-bath unit features a functional galley kitchen with generous cabinetry, a spacious living area, and an in-unit washer/dryer for added convenience. Additionally, a 6x8 storage unit is located in the lower level (common area) of the basement. The monthly HOA fee of $394 covers heat, hot water, and all exterior maintenance, providing worry-free living with one assigned parking space conveniently located near the front door and ample visitor parking. Ideally situated near Highways 84/17 and NJ Transit, enjoy easy access to Garnett Medical Center, Orange County Community College, as well as the growing list of amenities in and around Middletown, NY, all just 75 minutes from NYC. Call today to schedule your private showing!

$234,900 - Middletown, NY

143 Ruth Court Middletown, NY - A great Investment opportunity - - Low Taxes & Low Condo Fees. Currently leased. Tenant on a month to month lease @ $1,760 a month. Very quiet and well maintained condo complex. This first floor 2 bedroom, 2 bathroom condo offers a first floor King Sized master suite with walk in closet & full bathroom, a spacious living area with plenty of bright, natural light & a patio. The kitchen has almost new cabinets and appliances. Down the hall from the main living area are the bedrooms and 2 bathrooms. Great commuter location and close to Touro College, Routes 17 and 84 , NYC commuter trains , hospitals , shopping, and much more . This is worth a look ! Please note: this community is NOT FHA, FNMA or VA approved.

$210,000 - Middletown, NY

181 Ruth Court Middletown, NY - Welcome to Eastview Condominium, offering a two-bed, two full bath ground-level condo! Conveniently located near the front door, with ample visitor parking. Ideally situated near Highways 84/17 and NJ Transit, enjoy easy access to Garnett Medical Center, Orange County Community College, as well as the growing list of amenities in and around Middletown, NY, all just 75 minutes from NYC. Call today to schedule your private showing!

Middletown, New York listings for sale

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