Middletown Real Estate

Welcome to Middletown, NY, a vibrant city nestled in the heart of Orange County, where community spirit and educational excellence come together to create a nurturing environment for families. The Middletown School District is renowned for its commitment to providing high-quality education, making it a top choice for families seeking a supportive and enriching learning atmosphere for their children.

The district encompasses several elementary, middle, and high schools, each dedicated to fostering academic achievement and personal growth. With a diverse curriculum that includes advanced placement courses, arts, athletics, and extracurricular activities, students are encouraged to explore their interests and reach their full potential. The dedicated faculty and staff prioritize individualized attention, ensuring that every student feels valued and supported.

Middletown School District also emphasizes community involvement, offering numerous opportunities for parents and guardians to engage in their children’s education. From volunteer programs to school events, the district fosters a strong partnership between families and educators, creating a collaborative approach to learning.

In addition to academic excellence, the district is committed to the overall well-being of its students, providing access to counseling services, wellness programs, and a safe, inclusive environment. The schools are equipped with modern facilities and resources, ensuring that students have everything they need to succeed.

Living in Middletown means not only enjoying the charm of a close-knit community but also benefiting from a school district that prioritizes educational excellence. Discover the perfect home for your family in Middletown, where quality education and a supportive community await!

Newest Listings in Middletown

$450,000

4 Beds ⋅ 2 Baths ⋅ 1032844 MLS

Welcome to 41 Houston Avenue—an exceptional multi-family property offering incredible potential for both seasoned investors and first-time buyers! Whether you're looking to add a high-performing property to your rental portfolio or "house-hack" by living in one unit and letting the tenant income pay down your mortgage, this property delivers. ?Each spacious apartment boasts a well-designed layout featuring 2 comfortable bedrooms plus a versatile bonus room or den—perfect for a home office, nursery, or secondary living space. Landlord management is made easy with fully separated utilities, allowing tenants to pay their own gas and electric, keeping your overhead low and maximizing your net return.?Centrally located in Middletown with easy access to local shops, dining, public transit, and major commuter routes. Opportunities like this don't last long—schedule your showing today and tap into this turnkey revenue generator and a 2-car detached garage as an added bonus for more revenue!

41 Houston Avenue, 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 current, 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

$199,900

1030055 MLS

There is something different about standing on a piece of untouched land. The noise fades. Your pace slows. Instead of seeing walls, you begin seeing possibilities. As you walk across these 6.2 acres in Middletown, every step invites another idea. Perhaps the driveway winds gently through the landscape before opening to the home you've always imagined. Maybe a wall of windows captures the changing colors of every season. Mornings begin with coffee on a porch where the only soundtrack is birdsong and the breeze moving through the trees. Evenings end beneath a sky filled with stars that feel just a little brighter when the day belongs entirely to you. The beauty of undeveloped land is that there are no compromises waiting for you. No renovations to undo. No previous owner's decisions to work around. Every room, every view, every outdoor space begins as a thought and becomes a reflection of your own vision. Whether that means creating peaceful gardens, adding outdoor entertaining spaces, designing a detached workshop or studio, or simply preserving the natural beauty around you, this property offers the freedom to build a lifestyle instead of settling for one. Life here is about enjoying the space to breathe while remaining connected to everything that matters. Located approximately 70 miles from New York City, this property offers an ideal balance of peaceful surroundings and everyday convenience. Shopping, dining, healthcare, entertainment, and daily essentials are just minutes away, while nearby Metro North rail service, Interstate 84, and Route 17 make commuting and traveling throughout the Hudson Valley and into the city remarkably convenient. When the workweek ends, the Hudson Valley becomes your playground. Spend the afternoon exploring scenic hiking trails, browsing local farm markets, discovering charming villages, enjoying seasonal festivals, or taking in the beauty of nearby parks and outdoor recreation. Visit the Newburgh waterfront for dinner overlooking the Hudson River, spend a day shopping at Woodbury Common Premium Outlets, or enjoy one of the region's many wineries, breweries, and locally owned restaurants. New York City is close enough for an exciting day trip, yet far enough away that returning home truly feels like an escape. Some people search for the perfect home. Others recognize that the greatest opportunity is creating one from the ground up. This 6.2 acre parcel offers more than land. It offers the rare chance to shape your surroundings, design every detail with intention, and build a place that reflects not where you've been, but where you're going. The foundation has already been provided by nature. Now, the next chapter is yours to write.

Keasel Road, Middletown

$129,000

1031561 MLS

Discover this scenic 3-acre vacant parcel offering privacy, mature trees, and endless possibilities for recreational use or long-term investment. Buyer to verify all permitted uses with the appropriate municipality.

114 Highland Lake 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

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