Middletown Homes for Sale

Welcome to the vibrant community of Middletown, NY, nestled in the picturesque Orange County. Known for its rich history and diverse culture, Middletown offers residents a delightful blend of suburban charm and urban convenience. One of the standout features of this thriving city is its exceptional school district, which is dedicated to providing a high-quality education for all students.

The Middletown City School District is renowned for its commitment to academic excellence and holistic development. With a variety of educational programs, dedicated staff, and a focus on student engagement, the district aims to prepare young minds for future success. Families can take pride in the array of extracurricular activities, advanced placement courses, and special education services that cater to the diverse needs of its student population. The schools are equipped with modern facilities and technology, fostering an environment conducive to learning and growth.

As you explore the real estate opportunities in Middletown, you'll find a range of homes for sale that cater to various lifestyles and budgets. From charming single-family residences to modern townhomes, the housing market in Middletown is vibrant and diverse. Whether you're a first-time buyer or looking to upgrade, you’ll discover properties that not only meet your needs but also offer proximity to top-rated schools, parks, and community amenities.

Living in Middletown means embracing a community where education, family, and quality of life are prioritized. Explore the homes for sale today and take the first step towards making this wonderful city your new home!

Newest Middletown Homes for Sale

$339,000

2 Beds ⋅ 2 Baths ⋅ 1033088 MLS

Welcome to your new ranch home situated on a quiet dead end street yet still close to all major amenities. Arriving you will notice the peaceful surroundings, well manicured and level yard space, convenient garage and ample parking. Step inside your new home to find sun drenched living spaces, gleaming hardwood floors and the ease of one level living. The main level provides you with a cozy living room, two bedrooms, renovated full bath, updated kitchen and a formal dining room which provides flexibility for a potential den/office. Your eat-in kitchen provides ample storage space, gas cooktop, wall oven, Bosch dishwasher and easy access to the rear deck. The lower level of the home allows for additional expansion with it's own entrance, large family room, full bath with stall shower, laundry area and garage space. Enjoy relaxing out back on the mult-tiered deck space or find it the perfect place for entertaining and summer gatherings. All of this in a serene location yet minutes to shops, restaurants, schools, gyms, nature trails and much more.

11 5th Street, Middletown

$333,000

3 Beds ⋅ 1 Baths ⋅ 1032936 MLS

Come see this well maintained 2 story colonial style home. Centrally located in the City of Middletown which allows you to be minutes away to all the great eateries and to all major shopping and public transportation. The home has taken a few updates over the years. Home has a spacious living room that leads into a formal dining room. Kitchen has plenty of cabinet space as well. The central a.c has been updated. Basement allows for storage and large laundry area. Don't miss out on this!

23 Harrison Street, Middletown

$419,900

4 Beds ⋅ 1 Baths ⋅ 1031475 MLS

Welcome to this charming and well-maintained 4-bedroom home offering a practical layout and timeless character. The main level features a bright living room, formal dining room, eat-in kitchen, two bedrooms, and a full bath, while the upper level provides two additional bedrooms with flexible living space. Recent improvements include a new roof (2024), vinyl double-pane windows installed in 2018, and a resurfaced driveway completed in 2023. A bright enclosed front porch adds additional living space and a welcoming place to relax. Outside, enjoy a generous backyard, a detached two-car garage, and ample off-street parking. Conveniently located near schools, shopping, restaurants, parks, and major highways, this home offers comfort, convenience, and everyday functionality in an established neighborhood. Some photos have been enhanced for presentation purposes. Some interior photos have been virtually staged for illustrative purposes only to demonstrate potential furniture placement. The property is being sold in its actual unfurnished/as-is condition.

39 California Avenue, Middletown

$449,900

3 Beds ⋅ 1 Baths ⋅ 1028580 MLS

STOP THE SEARCH!!!! THIS ONE IS A SHOWSTOPPER!!! Welcome home to 30 Murray Road in the Town of Walkill, an immaculately maintained, completely turn key ranch! Spotless from top to bottom and lovingly cared for, this exceptional home offers the perfect combination of comfort, style, and convenience. Simply unpack and start enjoying everything this beautiful property has to offer. Step inside to discover gorgeous hardwood floors flowing throughout the main living areas, complemented by beautiful tile flooring in the kitchen. The heart of the home features a stunning eat in kitchen with upgraded cabinetry, beautiful appliances, and ample workspace, making it as functional as it is beautiful. The thoughtfully designed layout includes a spacious family room, 3 generously sized bedrooms and a beautiful full bathroom! The immaculate full basement offers endless possibilities, whether you envision additional living space, a home gym, workshop, or simply appreciate the incredible amount of clean storage. A large two car garage provides even more room for vehicles, tools, and recreational equipment. Outside, you'll find your own private retreat. The incredible ground-level patio creates the perfect setting for relaxing, dining outdoors, or entertaining guests while overlooking the peaceful backyard surrounded by nature for exceptional privacy. A large turnaround driveway makes coming and going effortless, while the home's custom landscaping, enhances the curb appeal. Ideally situated in an outstanding Middletown location, you'll enjoy the tranquility of a quiet setting without sacrificing convenience. Shopping, restaurants, parks, schools, and major commuter routes are all just minutes away, making this the perfect place to call home. With its impeccable condition, tasteful updates, and unbeatable location, this move in ready ranch is a rare opportunity you won't want to miss. Call today to schedule your private showing. This immaculate home is an absolute must-see!

30 Murray Road, Middletown

$539,900

4 Beds ⋅ 3 Baths ⋅ 1031777 MLS

Welcome to this beautifully maintained Center Hall Colonial offering the perfect blend of classic design and comfortable everyday living. The heart of the home is the spacious kitchen, which opens seamlessly to the inviting family room, creating an ideal space for gathering with family and friends. The family room is highlighted by custom built-in shelving and a cozy wood-burning fireplace, adding warmth and character. This home features four generously sized bedrooms and three bathrooms, providing plenty of space for family, guests, or a home office. The basement offers additional flexible living space perfect for a recreation room, fitness area, media room, or playroom. Outside, the newly paved walkway creates an attractive first impression and welcomes you home. Situated across from the Shawangunk Fish & Game Association, the property enjoys a unique setting with convenient access to outdoor recreation and open space. Combining timeless Colonial charm with functional living spaces and thoughtful updates, this home is ready to welcome its next owners.

31 Denman Road, Middletown

$498,000

4 Beds ⋅ 3 Baths ⋅ 1030876 MLS

Welcome to this well-maintained 4-bedroom, 3-full-bath home offering a functional layout and comfortable living spaces. The welcoming entry features an elegant chandelier and a large arched window that fills the home with natural light. The main level offers hardwood floors, vaulted ceilings, recessed lighting, a comfortable living room, and a separate dining area overlooking the backyard. The kitchen features stainless steel appliances, well-maintained wood cabinetry, and a tile backsplash. The primary bedroom includes a private en-suite bathroom, while two additional bedrooms and another full bathroom complete the main level. The finished walkout lower level provides additional living space with a family room, a fourth bedroom, a full bathroom, a dedicated home office with built-in shelving, and a laundry area. Enjoy the fully fenced backyard featuring a multi-level Trex deck, gazebo, and open green views, creating a comfortable space for relaxing or entertaining. Outdoor patio furniture is available to the buyer at no additional cost if desired. Additional features include an attached one-car garage, electronic keyless entry, and an existing solar panel system. Conveniently located near shopping, restaurants, schools, parks, and major commuter routes.

9 Ashland Avenue, Middletown

$495,500

3 Beds ⋅ 3 Baths ⋅ 1028819 MLS

Beautiful and well maintained , single family , townhouse located in the desirable community of Woodside Knolls This modern and spacious residence offers comfortable and spacious living across three floors & 2500 sq.ft! The 3 Bedroom, 3.5 Baths floor plan includes a luxurious primary bedroom with oversized walk in closets , en suite bathroom with full stand up shower and soaker tub. An additional two bedrooms , laundry room and full bath completes the upper floor. Downstairs you will discover a well equipped kitchen complete with stainless steel appliances, bonus office space , dining area and living room with a gas fireplace. A walkout door leads to your paved patio where you can enjoy outdoor entertaining. The finished basement with rough in for an additional bathroom is the icing on the cake and adds to endless configurations and possibilities to fit your lifestyle. All of this in a private community that includes a clubhouse, pool , basketball and tennis courts. This location is a commuters dream. Only minutes from major highways, trains and busses to NYC and the Galleria at Crystal Run, tons of shopping, wineries , historic trails and access to the heart of everything the Hudson Valley has to offer!

6 Avoncroft Lane, Middletown

$299,900

3 Beds ⋅ 2 Baths ⋅ 1030626 MLS

Step inside this classic 3-bedroom, 2-bath Colonial and imagine the possibilities. Offering approximately 1,610 square feet, the home features a traditional layout with a living room, formal dining room, spacious kitchen, and a flexible first-floor bonus room that can serve as a den, home office, or recreation space. A dedicated laundry area adds everyday convenience, while the covered front porch overlooks an open view with no homes directly across the street. Upstairs are three bedrooms, including a primary bedroom with a walk-in closet, along with a second full bath. The flat 37' x 150' lot includes a usable backyard, shared driveway, and rear parking for approximately three vehicles. Public water, public sewer, natural gas heat, and a partial unfinished basement provide a functional starting point. The home is ready for its next owner to bring their vision and update it to their taste. Located just one block from Sproat Street Park and Pool, with convenient access to I-84, Route 17, shopping, medical facilities, and nearby parks

158 Cottage Street, Middletown

$370,000

3 Beds ⋅ 3 Baths ⋅ 1029917 MLS

Welcome to 15 Old Anvil Ln, Middletown, a lovingly cared for end unit townhouse in the sought after "The Meadows" community. This unit has been lived in and cared for by the same owners for approximately 40 years. The owner is a builder so he has not skipped on his own improvements and care. The unit offers 3 bedrooms and 2.5 bathrooms, a kitchen and formal dining room with a slider to a beautiful deck which overlooks the backyard and a beautiful koi-pond. There is also a covered screened in side deck and a patio. The living room has a propane fireplace. The primary suite offers 2 closets, bathroom with marble flooring and an electric fireplace. The main bathroom is also lovely and has a whirlpool tub. The walk out lower level features a family room or den plus the laundry room and access to the 1 car garage. Save on utility bills with the solar panels and enjoy the community pool, clubhouse and the tennis, basketball and handball courts. Short drive to all amenities and highways including Galleria Mall, Garnet Health Center, and Metro North Train Station. These units are hard to come on the market, so don't delay and schedule your appointment for a showing!

15 Old Anvil Lane, Middletown

$495,000

3 Beds ⋅ 3 Baths ⋅ 1027934 MLS

Welcome to this beautifully maintained 2,500 sq. ft. townhouse in the desirable Woodside Knolls community. This spacious home offers 3 bedrooms, each featuring a walk-in closet, and 2.5 bathrooms. The open-concept floor plan seamlessly connects the living area and modern kitchen, creating an inviting space for everyday living and entertaining. Additional features include a two-car attached garage and access to community amenities, including a clubhouse, swimming pool, basketball court, and tennis courts. Conveniently located near schools, parks, shopping, dining, and major commuter routes, this home offers a comfortable lifestyle in a well-established community.

58 Cobblestone Lane, Middletown

$339,000

2 Beds ⋅ 1 Baths ⋅ 1027980 MLS

Welcome to 17 State St, a fully updated, energy-efficient detached home offering modern smart-home features and exceptional flexibility. The bright main level features central air, smart climate control, a beautifully tiled bathroom, custom window blinds with a transferable lifetime warranty, and an updated kitchen with premium stainless-steel appliances, including a brand-new smart refrigerator. The finished lower level provides expansive heated-and-cooled bonus space with dual mini-split systems and baseboard heat, making it ideal for a recreation room, home office, gym, guest space, or other flexible uses. Additional upgrades include solar panels, a built-in security system hookup, and an upgraded 240V electrical panel that's EV-ready. Outside, enjoy an extended driveway with ample off-street parking and a fully fenced backyard featuring a concrete patio, fire pit, and a brand-new storage shed. Completely move-in ready, this home combines modern efficiency with versatile living spaces in a convenient Middletown location.

17 State Street, Middletown

$239,000

3 Beds ⋅ 2 Baths ⋅ 1029110 MLS

Calling all contractors, investors, and homeowners with a vision! Bring your ideas and your toolbox to this 3-bedroom, 1.5-bath split-level home situated on a desirable corner lot within the Enlarged City School District of Middletown. Offering great bones and endless potential, this property is ready for its next owner to restore, renovate, and make it their own. Inside, you'll find a functional split-level layout that's ready for your personal touches and updates. Whether you're looking for your next investment project or the opportunity to create your dream home, this property is full of possibilities. Conveniently located in a peaceful neighborhood just minutes from Orange County Community College (SUNY Orange), Touro College of Osteopathic Medicine, Garnet Health Medical Center, shopping, dining, and major commuter routes. With New York City approximately 70 miles away, you'll enjoy the perfect balance of suburban living with easy access to the city. Don't miss this opportunity to unlock the potential of this hidden gem—schedule your showing today!

26 Willow Place, Middletown

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