Middletown Homes for Sale

Welcome to Middletown, New York – a hidden gem nestled in the heart of Orange County! With its rich history, vibrant community, and picturesque landscapes, Middletown offers the perfect blend of small-town charm and modern convenience. Situated just 70 miles northwest of New York City, this city is an ideal haven for those seeking a peaceful lifestyle without sacrificing access to urban amenities.

Middletown boasts a diverse array of homes for sale, catering to various tastes and budgets. Whether you're searching for a cozy starter home, a spacious family residence, or a charming historic property, you’ll find it all here. The real estate market in Middletown is thriving, with options that include contemporary townhouses, elegant single-family homes, and even sprawling estates nestled in serene surroundings. Each neighborhood has its unique character, providing a welcoming atmosphere that encourages community engagement.

For outdoor enthusiasts, Middletown is surrounded by stunning natural beauty, featuring parks, hiking trails, and recreational opportunities. The nearby Hudson Valley offers breathtaking views and outdoor adventures, making it a perfect playground for nature lovers. Additionally, the city is home to a variety of shops, restaurants, and cultural attractions, ensuring that there’s always something to explore.

If you’re considering making Middletown your home, now is the perfect time to dive into the local real estate market. With a range of homes for sale, you can find the ideal property that suits your lifestyle and budget. Embrace the charm of Middletown and discover the perfect place to call home!

Newest Middletown Homes for Sale

$245,000

4 Beds ⋅ 2 Baths ⋅ 1050322 MLS

Calling All Investors & Visionaries! If you’ve been searching for an investment opportunity in a great location, look no further than 191 Wickham Ave. in Middletown! This property offers tons of potential for the right buyer and is ready for someone with the vision and creativity to bring it back to life. Featuring 4 bedrooms, 1.5 bathrooms, a full basement, a detached garage, and a spacious backyard, this home offers plenty of room to create something truly special. The property does require TLC and renovations, but that’s exactly where the opportunity lies. Bring your equipment, your ideas, and your contractor, and transform this house into a beautiful residence or a potentially profitable investment. Centrally located in Middletown, this property provides convenient access to local shopping, dining, schools, transportation, and everything the area has to offer. Low taxes add even more appeal for investors and buyers looking to maximize the potential of their purchase. Whether your goal is to flip the property, renovate it as a rental, or create your own ideal home, the possibilities are worth exploring. With a detached garage, backyard space, and full basement, there’s plenty of opportunity to add value and make this property your own. And let’s talk about the price! Opportunities like this don’t come around every day. If you’re looking for a property where your investment and vision can truly make a difference, this one deserves a closer look. Bring your tools. Bring your ideas. Bring your vision. Don’t miss this opportunity—submit your offer today and bring 191 Wickham Ave. back to life!

191 Wickham Avenue, Middletown

$375,000

4 Beds ⋅ 2 Baths ⋅ 1049994 MLS

Welcome to this beautifully presented 4 bedroom, 2 full bath home offering 1,520 square feet of thoughtfully designed living space on a level 0.50-acre property in the Town of Wallkill with Middletown schools. Freshly painted and filled with natural light, the home offers an amazing open layout complemented by stylish finishes and an exceptionally convenient location. At the heart of the home is a beautiful kitchen featuring granite countertops, generous workspace, and an inviting open floor plan that makes everyday living and entertaining effortless. The main level offers the added versatility of two bedrooms and a full bathroom, providing valuable options for guest accommodations, home office space, or additional living needs. Upstairs two additional bedrooms and a second full bathroom complete the home's four bedroom, two fullbath layout. Outside, enjoy the sunshine from your amazing back deck while the large, level backyard provides an impressive amount of usable outdoor space with plenty of room for recreation, gardening, entertaining, or simply enjoying the property. The location brings another major advantage. Positioned just minutes from Route 17 east and west, the home offers convenient access to major commuting routes while remaining close to the shopping, dining, services, and amenities found throughout the Town of Wallkill and Middletown area. Freshly painted, nicely appointed, and offering a versatile floor plan, generous property, and outstanding accessibility, this property combines comfortable living with the convenience of an excellent Hudson Valley location. Call today!

512 Bloomingburg Road, Middletown

$265,000

3 Beds ⋅ 2 Baths ⋅ 1045317 MLS

Bring your toolbox and your imagination. With some work and creativity, this property offers an exciting opportunity to make it your own. Offering plenty of character and charm, some updates will go a long way in making this beloved home truly shine. Endless potential awaits with this centrally located two story home in Middletown. Highlights include an inviting wraparound front porch, a spacious double lot, an updated kitchen, and a large walk up attic offering excellent additional storage and possibilities. Conveniently located close to shopping, dining, schools, major roadways, and everything Middletown has to offer. Whether you're looking for your first home or your next investment, this is an opportunity you won't want to miss. Come see the potential for yourself!

41 Wallkill Avenue, Middletown

$149,900

2 Beds ⋅ 1 Baths ⋅ PADA2064190 MLS

*PROPERTY CAN ONLY BE ACCESSED BY BOAT* Nestled along the serene banks of the Susquehanna River, this charming seasonal cottage offers a perfect blend of comfort and tranquility. With its inviting open floor plan, this residence is designed to create a warm and welcoming atmosphere, ideal for both relaxation and entertaining. Step inside to discover a cozy living space adorned with carpeting and thoughtful window treatments that allow natural light to fill the rooms. The heart of the home features a well-appointed kitchen equipped with essential appliances, including a refrigerator, stove, microwave, and icemaker, making meal preparation a delight. The open layout seamlessly connects the kitchen to the living area, fostering a sense of togetherness. The home boasts two spacious bedrooms, each designed to provide a peaceful retreat at the end of the day. The full bathroom is conveniently located, ensuring comfort and accessibility for all. A unique spiral staircase adds character and charm, leading to additional living space or storage options, perfect for personalizing to your needs. Outside, the property spans a generous 0.35 acres, offering ample space for outdoor activities or simply enjoying the picturesque views of the river. You can indulge in the beauty of nature right from your yard. A private floating dock awaits, providing easy access to the river for fishing, kayaking, or simply soaking in the serene surroundings. The location is truly a gem, offering a peaceful riverfront lifesty while still being conveniently accessible to local amenities. Whether you're looking for a weekend or summer getaway, this home provides the perfect backdrop for creating lasting memories. This property is a rare find. Embrace the opportunity to live in a cottage that not only meets your needs but also enhances your lifestyle. Experience the joy of riverfront living and make this charming home your own. Dont wait schedule your showing today the river season is not over just yet! Seller is a licensed real estate agent

18 Beech Island Isl, Middletown

$225,000

3 Beds ⋅ 2 Baths ⋅ PADA2064170 MLS

Charming three-bedroom, one-bathroom home in Middletown offering a comfortable layout and plenty of potential. One bedroom is conveniently located on the main level, while the updated kitchen features a welcoming feel and a separate dining area perfect for everyday meals or entertaining. The full basement provides ample space for storage, hobbies, or future possibilities. Outside, enjoy a partially fenced backyard, two storage sheds, and a large covered deck that offers a great spot to relax and enjoy the outdoors. This charming home has plenty to offer and is a must-see!

653 Briarcliff Rd, Middletown

$739,990

3 Beds ⋅ 4 Baths ⋅ DENC2111338 MLS

Brand New 55+ Community in Middletown, DE Welcome to the Carver, a beautifully designed home that combines an open-concept layout with plenty of natural light. Scheduled for settlement in October 2026, this home offers 3 bedrooms, 3.5 baths, and a 2.5-car garage, providing a comfortable blend of style and functionality. A welcoming front porch creates charming curb appeal, while the screened deck offers an inviting space to enjoy the outdoors. Inside, the finished basement provides additional living space, and a fireplace adds warmth and character to the main living area. The spacious kitchen features a huge island and quartz countertops, perfect for cooking, gathering, and entertaining. Laminate flooring throughout the first floor offers a cohesive and stylish finish, while the bathrooms feature a walk-in shower with tile walls. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

1620 Jaymes Cir, Middletown

$579,000

3 Beds ⋅ 3 Baths ⋅ 1050855 MLS

New Construction. This 3-bedroom, 2.5-bath colonial is situated on a 2-acre level/partially wooded lot. The first floor offers an oversized living room, dining room, a kitchen with granite countertops and stainless appliances, and sliders leading to a backyard deck. Also on the first floor, you'll find a den/study, a laundry room, and a good-sized 1/2 bath. The second floor features a large loft area and 3 bedrooms, including the master suite with an en-suite bath. Central A/C and hardwood floors throughout. A detached 2-car garage is also included. Additional Information: ParkingFeatures:2 Car Detached,

30 Daly Road, Middletown

$380,000

3 Beds ⋅ 3 Baths ⋅ 1050843 MLS

Welcome to this beautifully updated and well-maintained single-family home, featuring original hardwood floors, updated kitchen and bathrooms, and a spacious layout. The first floor offers a large living room with a fireplace, formal dining room, eat-in kitchen with access to the backyard, and a full bathroom. Upstairs, you’ll find three generously sized bedrooms and a full hallway bathroom. The finished walk-up attic provides additional flexible living space, while the finished basement includes a laundry area, half bathroom, utility room, and workshop/storage space. Enjoy a detached garage, enclosed backyard, and inviting front and back porches. Conveniently located near schools, shopping, and major highways, this home offers comfort, character, and convenience.

11 Gardner Avenue, Middletown

$680,000

5 Beds ⋅ 3 Baths ⋅ MDFR2089044 MLS

Step into a world of timeless elegance with this stunning Victorian home, a true masterpiece of craftsmanship and design. Built in 1900, this residence boasts and shows a life of owners who loved it and those who appreciated its unique architectural features. Beautiful hardwood floors throughout the entire home, including in the updated and modernized kitchen! Upgraded countertops and stainless steel appliances, including a dishwasher, 40" dual-fuel range and refrigerator. An extra refrigerator/freezer in the basement provide ample storage for all your culinary needs. The main floor laundry acts as a separator and tie between the rest of the house and the "in-law" suite which was once the summer kitchen. Retreat to one of the five generously sized bedrooms, each offering a peaceful haven for rest and relaxation. The home boasts 3 fireplaces, one fully flued for log burning, and though the other two are sealed off, the one in the kitchen has a wood-style, ventless propane stove installed. The bathrooms are thoughtfully designed, featuring walk-in showers, glass doors and electric, radiant-heat tile floors. One bathroom has even had accessibility in mind making it a "wet room" for those with mobility issues. Outside you will find no detail missed, as even the exterior shingles were hand scalloped to properly match the original victorian look and design. The front porch is inviting and relaxing to watch traffic drive by on their way through Middletown, and the sleeper porch allows you to have some peace and quiet while enjoying nature. With nearly a third acre lot, there's plenty of room for outdoor activities or gardening. This Victorian gem is not just a house; it's a place where memories are made, and stories are shared. Experience the perfect blend of classic elegance and contemporary comfort-your dream home awaits!

21 E Main St, Middletown

$935,000

3 Beds ⋅ 4 Baths ⋅ 1048303 MLS

Set on 9.4 private acres, this extraordinary custom home offers high-function living, privacy, and expansive outdoor space. Designed by the renowned architectural firm, Pendergast & Terach, and inspired by contemporary craftsman design, the open single-level layout creates a seamless flow throughout. The home features a soaring cathedral ceiling, anchored by an impressive stone fireplace and floor-to-ceiling windows that blur the boundary between the interior and exterior landscape. Wood posts and beams throughout the central living space provide warmth to the clean, modern lines and abundant natural light. The kitchen boasts high-end appliances, Premium Silestone countertops, and custom cabinets. The primary bedroom suite, complete with Japanese soaking tub, opens to a deck surrounded by nature. The finished lower level has French doors, a full bath, and ample storage space, office space, and room for future living expansion. All this and an oversized 2+ car garage. Convenient to outdoor activities such as hiking, boating, paddling, fishing and swimming, this one-of-a-kind home is located just over an hour to the George Washington Bridge, and one mile from the train to NYC.

194 White Bridge Road, Middletown

$549,900

2 Beds ⋅ 3 Baths ⋅ 1049692 MLS

Enjoy the ease of main-level living with the bonus of a beautifully designed second floor in Wildflower at Wallkill, a gated 55+ active-adult community. Offering approximately 2,400 square feet, this spacious two-bedroom, two-and-a-half-bath home features an open, comfortable floor plan designed for both everyday living and entertaining. The main level welcomes you with generous living and dining areas filled with natural light and custom trim. At the heart of the home, the kitchen features granite countertops, custom backsplash, abundant cabinetry and an impressive nine-foot island with plenty of room for seating. Just beyond, a comfortable family room with a natural gas fireplace creates a warm gathering space and flows easily into the kitchen. Also located on the main level is the primary bedroom suite, offering the convenience of true one-level living. Upstairs, guests can enjoy their own private area with a second bedroom, full bath and a versatile flex space—perfect for a sitting area, home office, hobby space or quiet retreat. The private rear patio provides a lovely spot for morning coffee, gardening or relaxing outdoors. An attached two-car garage adds everyday convenience. Life at Wildflower at Wallkill extends well beyond the front door. Residents enjoy a gated community with indoor and outdoor pools, clubhouse, tennis and pickleball courts, exercise classes, organized trips and an active calendar of social activities. Shopping, restaurants, medical offices and everyday conveniences are all just minutes away.

6 Cyprus Drive, Middletown

$300,000

3 Beds ⋅ 2 Baths ⋅ PADA2064166 MLS

Welcome to this inviting bilevel home situated on a desirable corner lot with an amazing yard and fresh landscaping! Step inside the foyer and head upstairs to the main level, where the spacious living room features plush carpeting and a cozy gas fireplace. The formal dining room offers vinyl flooring and convenient outdoor access, while the eat-in kitchen provides plenty of cabinet space, a pantry for storage, vinyl flooring and a ceiling fan. Three generous bedrooms and a full bath complete the main level. Enjoy the changing seasons from the carpeted sunroom, a wonderful additional space to relax and take in views of the outdoors. The lower level offers even more living space with two additional bedrooms and a full bath, along with a spacious family room featuring exposed wood beams, chair railing, window treatments and a wet bar—perfect for entertaining or relaxing with family and friends. Outside, the deck overlooks the cleared backyard, providing a great setting for outdoor gatherings, play or simply enjoying your own private space. An oversized two-car garage offers plenty of room for vehicles, storage and more. Conveniently located near shopping, dining and entertainment, this well-loved home offers space, versatility and a location that is hard to beat. A joy to own!

1720 Oberlin Rd, Middletown

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