Middletown Homes under $400,000

Welcome to Middletown, NY, where quality education meets charming suburban living! Nestled in the heart of Orange County, this vibrant city is not only known for its picturesque landscapes but also for its highly regarded school district. Middletown City School District prides itself on fostering a nurturing environment that promotes academic excellence and personal growth. With a variety of educational programs and extracurricular activities, students are encouraged to explore their interests and develop their talents, preparing them for a bright future.

Families seeking a home in this welcoming community will be delighted to discover that Middletown offers a variety of properties under $400,000. This affordability makes it an attractive option for first-time homebuyers, growing families, and those looking to downsize. Whether you’re in search of a charming single-family home, a cozy townhouse, or a spacious condo, you’ll find plenty of options that cater to your needs and budget.

Living in Middletown means enjoying the perfect blend of suburban tranquility and urban convenience. With easy access to local parks, shopping centers, and dining options, residents can relish the best of both worlds. The community is also well connected to major transportation routes, making commuting to nearby cities a breeze.

In Middletown, you’ll find not just a place to live, but a place to thrive. Discover your dream home in this wonderful city, where exceptional schools and affordable housing come together to create a vibrant community for all. Welcome to your new beginning in Middletown!

Newest Middletown Homes under $400,000

$299,000

2 Beds ⋅ 2 Baths ⋅ 1058387 MLS

NO HOA FEES! LOW TAXES!! Welcome to easy, effortless living in this turnkey, move-in ready 2-bedroom home, thoughtfully updated with modern finishes and designed for today’s lifestyle. From the moment you step inside, you’re greeted by a bright and inviting interior that feels both stylish and comfortable. The updated kitchen shines with sleek countertops, crisp cabinetry, and modern appliances, making it as functional as it is beautiful. The living and dining spaces flow seamlessly together, creating the perfect setting for both everyday living and entertaining. The bedrooms are generously sized, offering comfort, versatility, and ample closet space, while the updated bath adds a fresh, contemporary touch. Every detail has been carefully considered to create a home that is truly move-in ready, allowing you to settle in and start enjoying it right away. With its stylish upgrades, low taxes, and low-maintenance lifestyle, this home is the perfect blend of function, comfort, and charm. Whether you’re a first-time buyer, looking to downsize, or searching for a smart investment opportunity, this beautifully updated home offers the perfect blend of style, convenience, and low-maintenance living. With its turnkey condition and modern appeal, this is a home that truly stands out. Ideally located near I-84, Route 17/I-86, shopping, dining, medical facilities, and everything Middletown has to offer, this home combines everyday convenience with Hudson Valley appeal. Whether you’re a first-time buyer, downsizing, or searching for a smart investment, this turnkey property checks all the boxes. Homes like this don’t last long, schedule your private showing today!

15 N Aspen Road, Middletown

$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

$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

4 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

$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

$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

$284,900

2 Beds ⋅ 2 Baths ⋅ 1053223 MLS

WHAT A WONDERFUL OPPORTUNIY: This condo is located in the prestigious Clemson Park.___________________________________________________________________________________________________________________________ This 2 bedroom, 2 bathroom unit is close to major highways and shopping malls. DO NOT LET THIS OPPORTUNITY PASS YOU BY!

132 Sycamore Drive, Middletown

$325,000

3 Beds ⋅ 1 Baths ⋅ 1052724 MLS

This 3-bedroom, 1 bath raised ranch in Middletown offers 1,092 square feet of living space on a 0.22-acre lot, with a practical layout, hardwood floors, an attached two-car garage, just needs a little cosmetic refreshing to make it shine. The main level features a spacious living and dining area with hardwood flooring and a large picture window, creating an open, comfortable setting for everyday living and entertaining. The kitchen includes extensive warm wood cabinetry, light-colored countertops, a tiled backsplash, a gas range, built-in microwave, dishwasher, refrigerator, and a ceiling fan, with a convenient layout that connects naturally to the dining area. The home offers three bedrooms and a full bathroom with a tub/shower combination and wood cabinetry for storage. The lower level offers excellent potential for additional living space and an attached two-car garage. Outside, the property offers a beautiful back yard with a broad lawn, established landscaping, a paved rear patio, and attractive hardscaping with retaining walls that help define the sloped lot. Located in Middletown within the Middletown School District, the property is convenient to local shopping, dining, recreation, and transportation. The nearby Metro-North station provides service to NYC on the Port Jervis Line, while the Galleria at Crystal Run offers more than 100 shopping, dining, and entertainment options. The city also maintains numerous parks and recreational facilities. Major road connections including NY-17/I-86, NY-211, and I-84 provide access throughout Orange County and the surrounding Hudson Valley.

55 Orange Terrace, Middletown

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