Middletown New York homes for sale starting at Fifty Thousand Dollars

$369,900 - Middletown, NY

9 Fairview Avenue Middletown, NY - A must see home! This beautiful colonial home will have everything brand new - from the exterior: roof, sidings, windows, porch, deck to the interior: kitchen, all walls with plumbing and electrical lines, kitchen with brand new cabinets, countertops and appliances: refrigerator, oven/range, microwave and dishwasher, beautiful bathrooms with tiles, hardwood floorings - all NEW. Featuring 3 bedrooms and 1.5 bathroom with an open layout from the living room, gorgeous kitchen, a dining area leading to the sliding door to the great size deck. It is located in the center of Middletown - near NYC Transportations, hospitals and major highways.

$369,900 - Middletown, NY

21 Creeden Drive Middletown, NY - Welcome Home to 21 Creeden Drive! This inviting 3-bedroom, 1.5 Bath home offers the perfect blend of privacy and convenience, located just minutes from town on a peaceful, cul-de-sac road. Featuring a spacious main floor, a walk-out lower level and serene backyard, it is a must-see! While this well-kept home is move-in ready, it also presents an exciting opportunity to add your own touch and bring out its full potential. The original hardwood floors remain throughout the first floor, and the homes exterior is a blank canvass waiting to be brought to life! With a welcoming neighborhood and endless potential, this property is ready to become your next home!

$369,000 - Middletown, NY

38 Wilson Street Middletown, NY - Welcome to 38 Wilson where charm, space, and potential come together. This 3-bedroom, 1.5-bath split-level home offers a fresh start with newly painted interiors and a layout full of possibility. Step inside to soaring cathedral ceilings and a bright open-concept kitchen, perfect for both everyday living and entertaining. Upstairs features three generously sized bedrooms and a full bathroom. Beautiful hardwood floors lie beneath the carpeting, offering an opportunity to enhance the space with timeless character and charm. The walk-out basement provides additional living space, while a versatile bonus room is ideal for a home office, art studio, or sitting area. Outside, an 816 sq ft pole barn offers incredible potential — with a little TLC, it could be transformed into a car enthusiast’s dream garage, or creative space. Whether you’re just starting out or looking to downsize, this home is nestled in a sought-after neighborhood that combines comfort, convenience, and community. Lovingly maintained by the same family since 1996, conventionally located by highways, train and bus to NYC, shopping, dining, hospital, and Orange County Fairgrounds. The keys to your dream home are within reach, come see it before it's too late.

$365,000 - Middletown, NY

8 Ebury Middletown, NY - Spacious 4-Bedroom Home in Desirable Canterbury Knolls – Town of Wallkill Welcome to easy, carefree living in the sought-after Canterbury Knolls community! This beautifully maintained and rare 4-bedroom, 3-bathroom single-family detached home is one of the largest in the neighborhood and offers both space and privacy—perfectly situated at the end of a quiet cul-de-sac, adjacent to peaceful woodlands. Inside, you'll find a bright and functional layout featuring a modern kitchen with stainless steel appliances, a dedicated dining room, a comfortable living room, and a versatile family/bonus room with glass sliders that open to a private backyard patio with serene views of grass and trees. The home also includes a 1-car garage. Canterbury Knolls offers an impressive list of amenities, including a clubhouse (ideal for meetings, events, and workouts), tot lot, tennis, racquetball, and basketball courts, all included in a low HOA fee that also covers lawn care, snow removal, trash service, and common area upkeep. Perfectly located near shopping, schools, public transportation, Orange Regional Medical Center, Touro College, major highways, and the Metro-North Railroad, this home combines convenience with comfort in a quiet, community-focused setting. Don’t miss your chance to own one of the most spacious homes in Canterbury Knolls—schedule your showing today!

$355,000 - Middletown, NY

184 Highland Avenue Middletown, NY - Here you have a beautiful Victorian style home, centrally located in Middletown NY. This home features a beautiful wrap around porch that presents a charming appeal to all visitors of the property. The property has been upgraded by the current owner, they have put in $55k of upgrades which include an updated kitchen, new central air system, new doors, and new windows! The home encompasses 4 bedrooms (3 of which are listed on the 2nd floor, and 4th bedroom is on the 3rd floor), and 2 bathrooms. The second floor also features a charming patio that allows you to look overlook Highland Avenue! Experience great natural lighting throughout the home that provides a relaxing and peaceful environment! This home is a great opportunity for homebuyers looking for a good price value property in the Middletown area. The current owner is relocating, so there is motivation to sale for the right offer! Interior pictures don't do the property justice. Come make this your home today!

$350,000 - Middletown, NY

2 Rivervale Road Middletown, NY - Charming Corner Townhouse in Middletown – No HOA Fees! Welcome to 2 Riverdale Road, a delightful 3-bedroom, 1.5-bathroom townhouse nestled in the heart of Middletown, NY. This spacious 1,484 sq ft home offers a perfect blend of comfort and convenience, making it an ideal choice for families and first-time homebuyers. Key Features: Spacious Living: Enjoy the warmth of hardwood floors throughout and freshly painted interiors that create a bright and inviting atmosphere. Functional Layout: The main floor boasts a cozy living room, a formal dining area, and a well-appointed kitchen, perfect for entertaining guests or enjoying family meals. Comfortable Bedrooms: Upstairs, you’ll find three generously sized bedrooms with ample closet space, providing plenty of room for rest and relaxation. Outdoor Space: Situated on a beautifully flat, fenced-in corner lot of 0.08 acres, this property offers a private outdoor area for gardening, play, or leisure. Modern Amenities: Equipped with central air conditioning and natural gas forced air heating, ensuring year-round comfort. Convenient Parking: Includes a private driveway, offering hassle-free parking for residents and guests. Community Highlights: Located in a friendly neighborhood with no HOA fees, this home is just minutes away from shopping centers, restaurants, and public transportation. Families will appreciate the proximity to quality schools, including Truman Elementary School, Monhagen Middle School, and Middletown High School. Don’t miss the opportunity to own this charming townhouse in a prime location. Schedule a viewing today and envision your future at 2 Rivervale Road!

$350,000 - Middletown, NY

86 Linden Avenue Middletown, NY - INVESTOR ALERT! This two-story home in Middletown presents a fantastic opportunity for savvy investors. Located in a commuter area, this property offers 4 bedrooms and 1 bathroom within 1,316 sq ft of living space. While this home requires some TLC, it's brimming with potential. Bring your vision and renovation ideas to transform this property into a profitable investment. Don't miss out on this chance to add value and reap the rewards! Contact us today for more information and to schedule a showing.

$349,000 - Middletown, NY

111 Walnut Street Middletown, NY - Fully Occupied 4-Unit Multifamily Property in the Heart of Margaretville A rare Village investment opportunity, well-maintained apartment building offers dependable income and long-term potential. Located in the Town of Middletown, Delaware County—where quality housing options remain limited—this property is ideally positioned to benefit from sustained rental demand. Location Highlights: • Prime in-village location, walking distance to school, shopping, restaurants, and other amenities • On-site parking for all tenants, with additional municipal parking just half a block away • Coin-operated laundry on site provides supplemental income • Garbage removal included, water included Property Features & Improvements: • Longstanding ownership since 2009, with major upgrades completed by both current and prior owners • Updates include: roof replacement, new windows, and upgraded electric systems (all apartments equipped with 100-amp electric meters) • High-speed internet, cable TV, and phone service available to all units Apartment Breakdown: Unit #1 – Studio (First Floor) • Private entry via shared covered front porch • 1 bathroom with shower stall • Electric heat, electric hot water, and electric cooking stove • Tenant pays all utilities Unit #2 – 2 Bedroom (Second Floor) • Entry via central staircase from shared covered front porch • Living room, full bath with tub/shower combination, and kitchen with electric stove • Heat (oil hot water baseboard) included in rent; tenant pays electric • Access to high-speed internet and cable Unit #3 – 1 Bedroom (First Floor) • Kitchen/living room combo with electric stove • 1 bathroom with shower stall • Electric baseboard heat; tenant pays all utilities • Entry from shared covered front porch Unit #4 – 2 Bedroom / 1.5 Bath (Two Story Layout) • Private covered side entry with enclosed porch and patio area • Eat-in kitchen, living room, half bath on the first floor • Two bedrooms and full bath upstairs • Heat (oil hot water baseboard) included in rent; tenant pays electric This property reflects pride of ownership, with consistent occupancy throughout the years. Looking to add to your portfolio?

$347,000 - Middletown, NY

203 Watkins Avenue Middletown, NY - Welcome Home! As you enter this nicely maintained capecod you'll notice the curved archway entry. To the left is a bonus room that could be used as an office/bedroom. The living room/ dining area combo has beautiful refinished hardwood floors. In addition to a full bathroom, kitchen with granite countertops, stainless steel appliances, white subway tile backsplash, and luxury vinyl plank flooring with a nice sized pantry closet and a 1st floor bedroom. Upstairs 2nd bedroom (finished attic) large enough to split into 2 rooms. Enjoy your summer days in the fenced in private backyard with a paver patio, large sized deck, garden beds and a fire pit. Great commuter location not far from the highway in addition to shops, restaurants, Galleria Mall, etc. A must see!!!

$339,900 - Middletown, NY

5 N Aspen Road Middletown, NY - Welcome to this updated 3-bedroom, 2-full-bathroom townhouse with luxurious upgrades throughout. As you step inside, you'll be greeted by an inviting living space filled with abundant natural light that leads seamlessly into the upgraded kitchen. The renovated kitchen is equipped with stainless steel appliances, ample storage, and functional counter space. The dining room, located next to the kitchen, features a slider leading to the fenced-in backyard. A laundry area with a washer/dryer and a full bathroom are also located on the first floor. Upstairs, the spacious primary bedroom features two closets. You'll also find two more generously sized bedrooms and a full bathroom on the second floor. Natural hardwood floors flow throughout the entire house. The home was fully updated in 2022, and the roof was replaced in 2023. Located in a lively neighborhood, this move-in-ready townhouse has NO HOA fees and is conveniently close to restaurants, shops, parks, a hospital, and all major commuting routes. Schedule an appointment to see this home—this could be your sweet spot!

Middletown, New York listings for sale

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