Middletown Homes under $500,000

Welcome to the vibrant community of Middletown, New York, nestled in the heart of Orange County! Known for its rich history and picturesque landscapes, Middletown offers a unique blend of suburban charm and urban convenience. One of the standout features of this area is the highly regarded Middletown School District, which is dedicated to nurturing the minds of its students through innovative programs and a supportive learning environment.

The Middletown School District boasts a variety of educational institutions, including elementary, middle, and high schools that cater to diverse learning needs. With a team of dedicated educators and a commitment to academic excellence, the district consistently ranks among the top in the region. Families can take comfort in knowing their children will receive a quality education, along with access to extracurricular activities that promote personal growth and community involvement.

For those looking to settle down in this charming city, there are numerous homes available under $500,000. Whether you're a first-time homebuyer or looking to downsize, Middletown offers an array of options, from cozy single-family homes to modern townhouses. The real estate market here is thriving, making it an ideal time to find your dream home without breaking the bank.

With its strong sense of community, excellent schools, and affordable housing options, Middletown is a wonderful place to call home. Discover the perfect balance of comfort and convenience in this delightful corner of New York!

Newest Middletown Homes under $500,000

$295,000

3 Beds ⋅ 2 Baths ⋅ 1056833 MLS

SPACIOUS FIRST-FLOOR RANCH-STYLE CONDO offering easy one-level living with 3 bedrooms and 2 full baths and no interior steps. Convenient parking is located just a few steps from the front door, making this a great option for anyone looking for easy accessibility and the convenience of first-floor living. The home features central air, laminate flooring and carpeting, a spacious eat-in kitchen with plenty of room for everyday dining, and a large living area with sliding glass doors leading to your own private patio. There is plenty of natural light throughout the home, creating a bright and comfortable living space. The primary bedroom offers its own private full bath and walk-in closet. Two additional generously sized bedrooms provide flexibility for family, guests, or a home office, along with a second full bath. A convenient stackable washer and dryer completes the one-level layout. This condo has been enjoyed for many years and offers a wonderful opportunity for the next owner to make it their own with some fresh paint and personal touches. Conveniently located close to shopping, major highways, bus transportation, and the train. With three bedrooms, two full baths, first-floor living, a private patio, and an easy-to-navigate layout, this home offers a lot of potential in a convenient location.

18 Revere Drive, Middletown

$374,999

2 Beds ⋅ 1 Baths ⋅ 1053196 MLS

Welcome home to 138 Prospect Avenue! This beautifully renovated, truly turn-key home is ready for its new owner. With thoughtful updates throughout, everything feels fresh, modern, and move-in ready. Step inside to find newly finished hardwood floors, recessed lighting, and an inviting open-concept layout. The updated kitchen features brand-new sparkling granite countertops, stainless steel appliances (all under three years old), recessed lighting, and new hardwood flooring. Just off the kitchen, a charming 4' x 8' deck provides the perfect spot for grilling, enjoying your morning coffee, or conveniently bringing groceries up from the driveway. The living room flows seamlessly into the kitchen and features a wood stove that helps heat the entire home while keeping fuel costs down. A beautiful bay window fills the space with morning sunlight and highlights the gleaming hardwood floors. Two nicely sized first-floor bedrooms offer abundant natural light and hardwood flooring, providing comfortable and versatile living space. The fully finished lower level adds even more room to spread out, with a spacious family room, bonus room that could make a great home office, and a large storage/workshop area. The laundry area includes a brand-new washer and dryer, along with a utility sink to make household chores a breeze. The family room (25’11” x 14’8”) features brand-new flooring, a built-in bookcase with a clever secret door leading to the storage area, and a decorative fireplace that adds character and charm. Sliding glass doors open directly to the partially fenced, expansive backyard, creating an easy indoor-outdoor connection. Outside, you'll find a shed and plenty of space to create your ideal outdoor living area. With extensive updates, flexible living space, and a generous backyard, 138 Prospect Avenue is a wonderful place to call home!

138 Prospect Avenue, Middletown

$315,000

4 Beds ⋅ 2 Baths ⋅ 1058232 MLS

The property offers two separate units, in need of some TLC this classic two-story design features a covered front porch, a private driveway, yard space, and plenty of character throughout. Whether you are expanding an investment portfolio or looking for a multi-family property with long-term rental potential, this home offers flexibility and upside. Conveniently located near shopping, restaurants, schools, and everyday services, with the Galleria at Crystal Run just a short drive away. Outdoor recreation is also nearby at Fancher-Davidge Park and along the Orange Heritage Trail. Easy access to major roadways, including Route 17 and I-84, makes commuting throughout the Hudson Valley convenient. Bring your ideas and take advantage of the potential this Middletown two-family property has to offer. Tenants pay for their own electric, heat & hot water.

34 Houston Avenue, Middletown

$499,500

3 Beds ⋅ 3 Baths ⋅ 1057215 MLS

Welcome to 15 Randall Heights, a well-kept 3-bedroom ranch offering comfortable single-level living in the Middletown area. Built in 1957 and set on a generous 0.459-acre lot, with a nice level backyard this home provides 1,376 square feet on the main level and 1,976 total building square feet with 600 useable space in the basement. Inside, the functional layout includes three bedrooms, one full bath, and two half baths, with a wood burning fireplace anchoring the living space. Hardwood floors through out with renovated galley kitchen featuring newer cabinets, new formica counters, fridge and dishwasher approximately 1 yr old, washer and dryer about one yr old, and baths. Central air conditioning and hot-air heat keep the home comfortable year-round along with a humidifier. The full basement adds valuable flexibility, with 600 square feet already finished and plenty of room to make it your own. An attached garage connects to the home by a covered breezeway, offering protected, weather-friendly access between your car and the door. Out back, the large, level yard provides open space for gardening, entertaining, or simply relaxing outdoors. Whether you're a first-time buyer, looking to downsize, or ready to simplify to one-level living, this is a smart, solid value in a great location. Schedule your private tour today.

15 Randall Heights, Middletown

$309,900

2 Beds ⋅ 1 Baths ⋅ 1053243 MLS

Welcome to this cozy and comfortable 2-bedroom, 1-bath home in Middletown! Offering practical living space and plenty of storage, this home features a full finished walkout basement with a finished recreation room, laundry area with washer and dryer, and a new water heater. The full walk-up attic provides excellent additional storage and offers plenty of standing room. The home sits on approximately 0.19 acre with municipal water and sewer and low taxes. Bonus opportunity: the sale includes the adjacent 0.18-acre parcel at 100 Sprout Street, providing additional land and flexibility for the new owner. A comfortable home with useful finished space, great storage, and the added value of an additional adjoining parcel. Close to NJ Transit to NYC, restaurants, shopping, wineries and everything the beautiful Hudson Valley has to offer. Don't miss this opportunity to home ownership!

102 Sproat Street, Middletown

$365,000

3 Beds ⋅ 1 Baths ⋅ 1058181 MLS

Beautifully renovated Middletown home with an updated, move-in-ready interior. The property offers a long driveway with plenty of parking and is one of the few homes in the area with such generous outdoor space. Enjoy an exceptionally large, deep, fully fenced backyard with plenty of room to relax, entertain, and enjoy the outdoors. Conveniently located near shopping, dining, transportation, and major roadways.

74 Genung Street, Middletown

$499,900

2 Beds ⋅ 2 Baths ⋅ 1052305 MLS

Welcome to 24 Lilac at Wildflowers at Wallkill, a desirable sought after 55 and older community where comfort, style, and easy living come together in one beautiful home. This 2-bedroom, 2 full bath residence offers the convenience of single-level living with an open-concept designed for both everyday living and effortless entertaining. Lots of sunlight pours through oversized windows, filling the space with warmth and highlighting the modern feel. Step outside to your backyard oasis, perfect for morning coffee, outdoor dining, or simply unwinding on the patio in a peaceful setting. Life at Wildflowers at Wallkill is about a lifestyle. Enjoy access to a beautiful clubhouse featuring both indoor and outdoor pools, a fully equipped fitness center, locker rooms with private saunas, and dedicated spaces for yoga, games, and relaxation. Gather with neighbors in the spacious community rooms, host events with ease using two catering kitchens, or enjoy quiet time in the library. A full calendar of social activities offers something for everyone. Located near major highways, train stations, hospitals, shopping, dining, this home places you right in the heart of it all—while still offering a peaceful, community-focused setting. Don’t miss your opportunity to enjoy low-maintenance living in one of the area’s most sought-after active communities.

24 Lilac Street, Middletown

$199,000

1 Beds ⋅ 1 Baths ⋅ 1054352 MLS

This well-maintained 1-bedroom, 1-bathroom condo offers comfortable, convenient living with the added benefit of desirable ground-floor access. The functional layout features a spacious living area with direct access to your own private patio. An awning provides welcome shade and makes the patio an inviting extension of the living space. The generously sized bedroom offers plenty of room to create a comfortable retreat, while the convenient one-level layout makes everyday living easy. Whether you're looking for a low-maintenance residence opportunity, this Middletown condo is ready for its next owner!

122 Sycamore Drive, Middletown

$425,000

3 Beds ⋅ 2 Baths ⋅ 1055220 MLS

BEAUTIFULLY RENOVATED!!! LARGE DETACHED GARAGE!!! MUST SEE HOME!! Turnkey, thoughtfully renovated, and filled with warmth, this beautifully appointed ranch offers an exceptional combination of style, space, and effortless one level living in the heart of Middletown. Set across an oversized lot with picturesque views toward the nearby shrine and waterway, this is a home where nearly every space has been carefully refreshed and curated for modern living. Step inside and the transformation immediately takes center stage. Gorgeous new hardwood floors flow through the main living areas and bedrooms, creating a seamless sense of warmth and continuity. At the heart of the home is a completely new kitchen, beautifully finished with beautiful new cabinetry, champagne-bronze hardware, granite countertops, stainless steel appliances, recessed lighting, and elegant pendant fixtures. Polished yet inviting, it is a space designed to feel equally at home during quiet mornings or evenings spent entertaining. Beyond the main living area, a spacious, sun-filled family room offers an entirely different atmosphere. Brand new carpeting adds comfort underfoot, while a wood-burning stove brings character and warmth to the space. Large windows draw your attention toward the backyard, creating an inviting connection between indoors and out. A beautifully finished full bathroom and adjacent home office/guest room add tremendous flexibility to this portion of the home. Three generously sized bedrooms feature the same beautiful hardwood flooring, complemented by a second full bathroom that has been tastefully renovated with a fresh, refined aesthetic. Outside, the yard provides an impressive amount of usable space. A large concrete patio creates the perfect setting for outdoor dining, grilling, and entertaining, while the expansive backyard offers room to simply relax and enjoy the property. Two newly paved driveways provide excellent parking, while an attached one car garage and additional large detached garage deliver an incredible amount of storage and versatility. The large basement adds yet another layer of potential, whether envisioned for future finished space, recreation, hobbies, a workshop, or simply exceptional storage. Forced hot air heating and central air conditioning complete the home's everyday comfort. Centrally positioned in Middletown, the property offers convenient access to shopping, restaurants, schools, Orange County Community College, Touro College, medical facilities, recreation, and major commuting routes, while keeping the best of the Hudson Valley within easy reach. Freshly renovated, exceptionally versatile, and truly move in ready, this is one level living with far more to offer than meets the eye. Come experience it for yourself.

159 Wawayanda Avenue, Middletown

$399,000

3 Beds ⋅ 1 Baths ⋅ 1055264 MLS

TURNKEY RANCH!!!! ONE-LEVEL LIVING!!!! BEAUTIFULLY UPDATED IN MIDDLETOWN, NY!!! Welcome to 8 Keystone Park, where effortless one level living meets a beautifully maintained home in a quiet Middletown neighborhood. Thoughtfully updated, exceptionally cared for, and completely turnkey, this inviting ranch offers the comfort, simplicity, and outdoor living that make coming home feel easy. Step inside to a warm and welcoming interior designed for everyday living. The beautiful family room features brand new flooring and provides a comfortable gathering space filled with natural light. From there, the layout flows seamlessly into the updated kitchen, where refreshed finishes create a clean, polished setting for everything from morning coffee to dinner at home. Three well proportioned bedrooms and a full bathroom are conveniently arranged on one level, creating a floor plan that is both functional and refreshingly uncomplicated. Central air conditioning adds year round comfort, while the attached one car garage and large full basement provides additional convenience, storage, and easy access to the home. Outside is where this property truly invites you to slow down and enjoy the setting. The backyard offers a private place to relax, entertain, or simply enjoy a beautiful Hudson Valley afternoon. Installed just two years ago, the impressive 20' x 20' deck creates an expansive outdoor living space with plenty of room for dining, grilling, entertaining, or soaking up the sunshine. Beautifully maintained inside and out, 8 Keystone Park offers the increasingly sought after combination of single level living, thoughtful updates, central air, garage parking, and exceptional outdoor space, all within an established Middletown neighborhood and convenient to the shopping, dining, recreation, and major commuting routes the area has to offer. Turn the key, unpack, and start enjoying it from day one. Come experience 8 Keystone Park for yourself.

8 Keystone Park, Middletown

$394,900

2 Beds ⋅ 3 Baths ⋅ 1055933 MLS

Welcome to the Fairways of Middletown, a desirable gated community offering comfort, convenience, and an impressive array of amenities. This spacious townhome-style condo features 2 bedrooms and 2.5 bathrooms with a functional layout. The main level offers generous living and dining space, while the upper level provides two well-sized bedrooms, including a primary suite with its own private bath. Residents of the Fairways enjoy access to a community pool, clubhouse, billiards room, library, and fitness center, all within the security and privacy of a gated setting. Conveniently located near shopping, dining, major roadways, and everything Middletown has to offer, this home combines low-maintenance living with resort-style amenities.

19 Putters Way Unit #9, Middletown

$299,900

4 Beds ⋅ 2 Baths ⋅ 1055722 MLS

Four Bedrooms & Low Taxes in Middletown! Looking for four bedrooms without giving up living space? This 4-bedroom, 2-bath home offers the generous room sizes and distinct living areas that make older homes so appealing. Its rooms have space to serve their intended purposes, while a large attic and full basement offer ample storage and flexibility for other uses. Total annual property taxes were approximately $3,750 in 2025—unusually low for a home this size. A new high-efficiency Navien tankless combination boiler is another valuable upgrade. Located in Downtown Middletown, the home combines space, convenience, and low carrying costs for an owner-occupant or investor. The neighboring property may also be available separately for buyers interested in acquiring both.

4 Harding Street, Middletown

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