Middletown Homes with Pool Amenities

Welcome to Middletown, NY—a vibrant city nestled in the heart of Orange County, where community spirit meets exceptional educational opportunities. The Middletown School District is renowned for its commitment to academic excellence, offering a diverse array of programs designed to cater to the unique needs and talents of each student. With a blend of dedicated educators and innovative curricula, students are encouraged to thrive in a supportive environment that fosters both personal and academic growth.

Families relocating to Middletown will appreciate the district’s strong emphasis on community involvement and extracurricular activities, which play a crucial role in shaping well-rounded individuals. From sports teams to arts programs, students have ample opportunities to explore their interests and develop lifelong skills.

In addition to its outstanding educational offerings, Middletown boasts a variety of beautiful homes, many of which feature sought-after pool amenities. Imagine coming home to a stunning property where you can unwind and entertain friends and family by your own private pool. These homes not only provide a perfect retreat during the warm summer months but also enhance the overall quality of life for residents.

Whether you’re a growing family looking for a nurturing environment or a professional seeking a serene oasis, Middletown’s combination of excellent schools and beautiful homes with pool amenities makes it an ideal place to call home. Discover the charm of Middletown, where education and leisure come together to create a fulfilling lifestyle for everyone.

Newest Middletown Homes with Pool Amenities

$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

$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

$625,000

3 Beds ⋅ 3 Baths ⋅ 1025794 MLS

Welcome to this well-maintained 3-level townhome in The Fairways, a gated community conveniently located next to a golf course and just minutes from major highways, Garnet Health Medical Center, shopping, restaurants, and everyday conveniences. This home offers a 2-car garage, a finished lower level with direct garage access, and a functional floor plan designed for comfortable everyday living. The main level features hardwood floors throughout, an open-concept living and dining area with a gas fireplace, and a kitchen with granite countertops, a breakfast bar, pantry, gas range, dishwasher, refrigerator, and microwave. The adjoining breakfast area is surrounded by windows, filling the space with natural light. Sliding glass doors open to a private patio overlooking open green space, providing a peaceful setting for outdoor relaxation. The second level features two bright, generously sized bedrooms, a full hallway bath, and a conveniently located laundry area with a washer and dryer. The primary suite offers abundant natural light, a vaulted ceiling, a ceiling fan, a custom walk-in closet with built-in shelving and drawers, and a private en-suite bath with double vanities, a soaking tub, and a separate walk-in shower. The third-floor loft offers a versatile bonus area with a spacious walk-in storage room, providing flexible space for a home office, media room, gym, hobby space, or additional storage. Residents enjoy a variety of community amenities, including an outdoor pool, fitness center, clubhouse with a kitchen and lounge, billiards room, library, and beautifully maintained grounds. This home offers a functional layout, desirable community amenities, and a convenient location.

8 Green Court, Middletown

$499,900

3 Beds ⋅ 3 Baths ⋅ 1021212 MLS

Welcome to this beautifully updated end-unit townhouse with numerous upgrades completed in 2023! The bright and open main level features hardwood flooring, a spacious kitchen with granite countertops, a complementary tile backsplash, stainless steel appliances, abundant cabinetry, a large center island, pendant lighting, and recessed lighting. The kitchen flows seamlessly into the dining area and living room, creating a comfortable space for everyday living and entertaining. Sliding glass doors lead to a private deck overlooking a peaceful wooded backdrop, perfect for outdoor dining, grilling, or relaxing. A powder room and direct access to the attached two-car garage complete the main level. Upstairs, the primary suite features a vaulted ceiling, a walk-in closet, and an en-suite bathroom with a double-sink vanity featuring a new countertop installed in 2023, a soaking tub, and a separate glass-enclosed shower. Two additional bedrooms share a Jack-and-Jill bathroom with separate vanity and toilet/shower areas. A second-floor laundry room with washer and dryer adds everyday convenience. Updates completed in 2023 include fresh interior paint, hardwood flooring on the main level, new carpeting throughout the second floor and finished walk-out lower level, a new stove, a new primary bathroom vanity countertop, and smart home features including a Ring Video Doorbell and a Ring Floodlight Cam above the garage. Both Ring devices, along with all window blinds and curtains, will remain with the property. The finished walk-out lower level provides additional living space and direct access to a covered patio. Community amenities include a swimming pool, basketball court, and playground. Conveniently located near shopping, restaurants, schools, and major commuter routes. Most furniture may be included at no additional cost if desired by the buyer. The piano located in the basement is excluded from the sale and will be removed prior to closing. Schedule your private showing today!

37 Meadow View Drive, Middletown

$280,000

3 Beds ⋅ 2 Baths ⋅ 1020456 MLS

Welcome home! This inviting 3-bedroom, 1.5-bath townhome offers comfort, space and a welcoming layout. Owned by the same family for over 50 years, this home is now ready for its next chapter. Inside, you’ll find a large, comfortable living room that’s perfect for gathering and relaxing. The eat-in kitchen has been updated with new flooring and appliances, making it both functional and stylish. New carpeting throughout adds a fresh, updated feel, while improvements have already been completed, leaving room for the next owner to add their own finishing touches. New Roof was installed 3 years ago! Residents enjoy fantastic community amenities, including a swimming pool, basketball court, tennis court, playground, and clubhouse. The clubhouse is available for private parties and special events, making it easy to host gatherings close to home. Whether you’re looking for your first home, more space, or a place with great potential, this townhome offers comfort, convenience, and opportunity. Come see all that it has to offer!

18 Black Stallion Court, Middletown

$151,900

1 Beds ⋅ 1 Baths ⋅ 1015893 MLS

A fantastic opportunity for first time home buyers, downsizers or investors. Step into this freshly painted, well maintained 1 bedroom condo and experience easy living, low maintenance and community perks including pool and clubhouse. Stainless steel stove and dishwasher are only 3 years old, heating unit 7-8 years old. This complex is conveniently located near major highways and shopping. Enjoy parking only a few steps from your front door.This condo is ready for its new owner. Why rent? Don't miss the chance to secure a living space that's truly your own.

394 Concord Lane, Middletown

$479,000

3 Beds ⋅ 3 Baths ⋅ 1014031 MLS

Welcome to refined, low maintenance living in one of Middletown’s most sought after gated communities. This beautifully maintained end unit townhouse offers the perfect balance of space, comfort, and convenience, with over 2,000 square feet of living space designed for today’s lifestyle. Step inside to find a bright and inviting layout featuring spacious bedrooms each with generous closet space, along with 2.5 well appointed bathrooms. The flow of the home is both functional and comfortable, ideal for everyday living and entertaining alike. The finished basement expands your living space even further, offering incredible flexibility for a home gym, media room, office, or guest accommodations. A large attached two car garage adds convenience along with additional storage, making organization effortless. Enjoy peaceful mornings and relaxing evenings on your private patio, the perfect setting for coffee, unwinding, or hosting friends. As an end unit, you benefit from added privacy and natural light throughout the home. Located just minutes from I 84 and Route 17, this home offers easy access for commuting while being close to Garnet Health Medical Center, shopping, dining, and local amenities. For those who enjoy an active lifestyle, a beautiful golf course is just a short walk away. Residents of this community enjoy resort style amenities including a swimming pool, fitness center, clubhouse, and playground, creating an elevated living experience without the maintenance. Even better, the HOA covers common area maintenance, exterior maintenance, sewer, and snow removal, allowing for truly effortless living year round. This is more than just a home, it is a lifestyle of ease, comfort, and convenience all in one. Schedule your private showing today and experience it for yourself.

1 High Ridge Lane, Middletown

$369,900

3 Beds ⋅ 3 Baths ⋅ 1012400 MLS

Welcome to Buttonwood Hills! This spacious 3-bedroom, 2.5-bath townhouse offers comfortable, low-maintenance living in one of Middletown's most convenient locations. Featuring a bright and functional layout, the main level includes a generous living room, dining area, updated kitchen, convenient half bath, and in-unit laundry. Upstairs, you'll find a spacious primary bedroom along with two additional bedrooms and full baths, providing plenty of room and versatility. With renovated kitchen and updated bathrooms, this home is truly move in ready. Community amenities include an unground outdoor pool, clubhouse and recreational areas. Ideally situated just minutes from shopping, restaurants, schools, parks, Garnet Health Medical Center, Touro College, SUNY Orange and all major commuter routes including I-84 and Route 17, this home combines convenience, affordability, and easy condominium living. Whether you're a first-time buyer, downsizing, or looking for an investment opportunity, this Buttonwood Hills townhouse is ready to welcome you home.

202 Concord Lane, Middletown

$399,900

3 Beds ⋅ 3 Baths ⋅ 994032 MLS

Beautifully renovated 3-bedroom, 2.5-bathroom, 1-car garage, two-story townhouse located in the highly desirable Deer Run complex. This move-in-ready home features laminate flooring throughout, with tile flooring in the kitchen and bathrooms. The kitchen was tastefully updated in 2020, along with the heating and cooling system, which is electronically controlled and offers a high-efficiency SEER 16 rating. The living room boasts a fireplace with a high-end pellet stove insert, creating a warm and inviting atmosphere while helping to reduce heating costs. Deer Run offers great amenities, including a clubhouse available for special events, an inground pool, tennis courts, and more. Conveniently located just minutes from supermarkets, shops, and restaurants, with only a 5-minute drive to I-84 connecting to I-86. Close to Garnet Health Medical Center and the Galleria Mall. Approximately 10 minutes to LEGOLAND and under 20 minutes to Resorts World Catskills Casino Hotel. The HOA covers landscaping, snow removal, trash, and additional amenities for easy, low-maintenance living. This townhouse won’t last—schedule your showing today! Sale is subject to sellers securing suitable housing; they are actively looking.

83 Deer Ct Drive, Middletown

$285,000

2 Beds ⋅ 2 Baths ⋅ 990896 MLS

Well-maintained 2-bedroom, 2-bath condo in the Deer Run Community with an open layout and good natural light. Building entry with controlled access and interior access to the second-floor unit. The living and dining areas are combined and connect to a galley kitchen with a pass-through opening. The primary bedroom features a walk-in closet and a private full bathroom. New carpet was installed in 2025. In-unit washer and dryer. Community amenities include a clubhouse, swimming pool, and tennis court. Lawn care and snow removal are included. Additional highlights include assigned parking and a designated 12' x 11' locked storage unit. Conveniently located near shopping, dining, parks, and with easy access to highways.

66 Deer Ct Drive, Middletown

$490,000

3 Beds ⋅ 3 Baths ⋅ 974551 MLS

BACK ON MARKET: Welcome to this beautifully maintained newer-construction home in the sought-after Magnolia Park section of the Maple Fields community in Middletown. Built in 2019–2020, this spacious residence offers approximately 2,100 square feet of modern living with an open-concept layout designed for today’s lifestyle. The main level features a bright and airy living space, a stylish kitchen with granite countertops, stainless steel appliances, and a large center island, perfect for entertaining. Upstairs, you’ll find generously sized 3 bedrooms, including a primary suite with ample closet space and a private bath. Additional highlights include hardwood floors, a finished basement, and attached 2 car garage. Enjoy low-maintenance living with HOA $253 per month that include snow removal, landscaping, and access to community amenities such as a clubhouse, fitness center, swimming pool, playground, and sports courts. Conveniently located near major highways, shopping, dining, and within the Enlarged City School District of Middletown, this home offers the perfect blend of comfort, convenience, and community living. Don’t miss this move-in ready opportunity in one of Middletown’s most desirable neighborhoods!

19 Magnolia Park Road, Middletown

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.