Middletown Homes with Playground Amenities

Welcome to Middletown, New York—a charming city nestled in the heart of Orange County, where suburban tranquility meets vibrant community life. Known for its rich history and scenic landscapes, Middletown offers a unique blend of urban conveniences and rural charm, making it an ideal place for families, professionals, and retirees alike.

One of the standout features of Middletown is its commitment to family-friendly living, particularly evident in the availability of homes with playground amenities. Imagine stepping outside your front door and finding a safe, well-maintained playground just a stone's throw away. These homes not only provide spacious interiors and modern comforts but also foster a sense of community among neighbors who share a commitment to outdoor play and healthy living.

Middletown's parks and recreational facilities are designed to enhance the quality of life for residents. With playgrounds, sports fields, and walking trails, families can enjoy year-round outdoor activities. The city hosts numerous community events, from farmers' markets to seasonal festivals, ensuring there’s always something to do.

In addition to its recreational offerings, Middletown boasts excellent schools, shopping options, and dining experiences that cater to diverse tastes. With easy access to major highways and public transportation, commuting to nearby cities is a breeze, making Middletown a perfect blend of convenience and comfort.

Discover your dream home in Middletown, where playgrounds are just a heartbeat away, and every day feels like a new adventure. Embrace the charm of this vibrant city and enjoy a lifestyle that celebrates both community and nature!

Newest Middletown Homes with Playground Amenities

$380,000

3 Beds ⋅ 3 Baths ⋅ 1048889 MLS

Welcome to 13 Old Anvil Lane, a conveniently located Middletown home offering comfort, flexibility, and easy access to everything the area has to offer. With several updates already completed, the home feels fresh and move-in ready while still leaving room to add your own personal touch. Inside, you’ll find a comfortable and functional layout designed for everyday living. Plenty of bedrooms and bathrooms for the whole family. One of the home’s standout features is the full walk-out basement, offering excellent potential for additional living space, a recreation room, home office, gym, workshop, or extra storage. A private fenced-in yard is easy to maintain but offers additional gathering space for friends, family, and pets. Located just minutes from shopping like the Galleria Mall and Route 211, dining, Garnet Hospital, schools, major highways (I-84, 17/ I-86), gyms, and train transportation, this property makes commuting and daily errands exceptionally convenient. Whether you're looking for your first home, additional space, or a property in a highly accessible location, 13 Old Anvil Lane offers a great combination of value, versatility, and convenience in the heart of the Middletown area.

13 Old Anvil Lane, Middletown

$545,000

3 Beds ⋅ 3 Baths ⋅ 1037842 MLS

A rare opportunity in The Meadows! This expanded three-bedroom, 2 ½-bath raised ranch offers approximately 2,508 sq. ft. on more than half an acre. A 12-foot addition spanning both levels provides substantially more living space than many homes in the development. Set on a desirable corner lot facing woods, it offers a peaceful, secluded feel while remaining just five minutes from major shopping, Galleria Mall, dining, highways, and Garnet Medical Center. The open-concept main level features a chef-inspired kitchen with abundant wood cabinetry, hardwood flooring, a generous 8' x 3' peninsula, a newer induction convection range, and a second convection wall oven. Recessed lighting throughout creates a bright, modern environment. The fully finished walk-out lower level offers 1 ½ baths, multiple living areas, baseboard heat, luxury vinyl plank flooring, laundry alcove, and generous storage. A mirrored home gym is ideal for fitness, yoga, dance, or an art studio. The finished addition offers space for a playroom or family room, plus two flex rooms with exterior access-perfect for office, guest room, and/or mudroom. The fully fenced, level backyard is a private retreat with dramatic natural boulders, impressive multilevel stone patios, an electrified 6-foot granite outdoor island, and an included 8-foot Master Spa hot tub. Additional highlights include owned solar panels, two EV chargers, premium cedar-shake-style vinyl siding, updated windows and doors, and a roof with 50-year shingles. Enjoy The Meadows pool, clubhouse, tennis/pickleball, and playgrounds. This distinctive home must be seen to be fully appreciated.

2 Harvest Hill Lane, Middletown

$485,000

3 Beds ⋅ 3 Baths ⋅ 1043873 MLS

Wow! Move right into this beautiful corner unit in Maple Fields offering plenty of living space, 3 bedrooms, 2.5 baths, a finished basement, and a 2-car garage. Features hardwood floors on the main level, a spacious kitchen with granite counters and ample cabinetry, and comfortable bedrooms with large closets and carpeted floors. The laundry is conveniently located upstairs. The finished basement offers a large family room with plenty of additional space. Enjoy all the amenities Maple Fields has to offer, including a pool, clubhouse, playground, tennis, and more! Conveniently located near shopping and transportation with easy access to major highways.

34 Field Stone Drive, Middletown

$475,000

3 Beds ⋅ 3 Baths ⋅ 1042482 MLS

Welcome to 4 Woodrose Court, located in the peaceful Highrose Ridge community! Built in 2019, this modern townhome offers a bright, open layout with high ceilings, oversized windows and plenty of natural light. Step inside to hardwood floors throughout the main level and an open-concept kitchen featuring granite countertops, stainless steel appliances, a center island and plenty of space for everyday dining. Convenient access to the one-car garage is located just off the kitchen, along with a main-level half bath. The kitchen opens to the living room, where floor-to-ceiling windows create a bright, airy feel and access to the back deck extends the living space outdoors. Upstairs, the primary suite features a private bathroom and walk-in closet. Two additional bedrooms and another full bathroom complete this level. Second-floor laundry adds everyday convenience, keeping the washer and dryer right where you need them. Luxury vinyl plank flooring, installed in 2025, throughout the second level provides a clean, updated finish. The full finished walkout lower level adds even more flexible living space and is currently set up as a guest suite. Use it as a second living room, home office, playroom, gym or whatever best fits your needs. Sliding glass doors provide direct access to the backyard, while rough-in plumbing for an additional full bathroom offers the opportunity to add even more functionality in the future. Luxury vinyl plank flooring was also installed throughout the lower level. There is little left to do but move in and enjoy everything Highrose Ridge has to offer. Just down the street, community amenities include a clubhouse with fitness center, swimming pool and playground. Enjoy a peaceful setting surrounded by trees while remaining conveniently located near shopping, dining and the heart of Middletown. Schedule your private appointment today!

4 Woodrose Court, Middletown

$489,999

3 Beds ⋅ 4 Baths ⋅ 1009337 MLS

This beautiful 3 bed 3 1/2 bath townhome is nestled in the heart of Middletown with so much to offer and just minutes to transportation to and from NYC. Upon entering you'll find beautiful hardwood floors throughout the first floor. An open floor plan including a sun drenched living room with a fireplace, full glass door leading to a very spacious deck for outdoor grilling or relaxation. Just opposite the living room is an amazing kitchen with granite countertops, an island and stainless steel appliances. Upstairs you'll find a large primary bedroom equipped with a custom California closet setup and a gorgeous en-suite. The second floor is finished off by two large bedrooms, a full bathroom and a laundry room. The lower level is fully finished to be used however you desire and it walks out to a large patio and a beautifully manicured lawn leading to an area of undeveloped land that makes it quite peaceful and relaxing. Maple Fields is located 5-7 min near shops, parks, restaurants, and major highways 84/17! Offering tranquility and privacy and so much more, don't miss out on the opportunity to own this beauty. Additional Information: Amenities:Soaking Tub,Storage,ParkingFeatures:2 Car Attached,

93 Meadow View Drive, Middletown

$359,000

3 Beds ⋅ 2 Baths ⋅ 1037400 MLS

Welcome to inviting, freshly painted, updated 3-bedroom, 1.5-bathroom home in The Meadows community~Main floor offers kitchen-with brand new cabinets, new stainless steel appliances, granite countertops, roomy dining area, bright and expansive living room with large bay window and half bathroom~Door from the kitchen leads to the large deck perfect for relaxing and entertaining your guests outside~The second floor features 3 good size bedrooms-all freshly painted with brand new carpet and recently updated 1 full bathroom~The finished walk out basement has large extra space that could be an office, arts & crafts room or additional living space~There are sliders leading to the spacious fenced in backyard with endless possibilities, laundry and utility room with extra storage space~This home is truly commuters dream located just minutes from shopping, schools, dining, parks, major highways, transportation, Garnet Health Medical Center and other medical facilities~Low HOA fee with plenty amenities to offer-tennis, basketball, pool, clubhouse, playground~Call today to see this beautiful home~

21 Black Stallion Court, Middletown

$485,000

3 Beds ⋅ 3 Baths ⋅ 974551 MLS

BACK ON THE MARKET—VACANT AND MOVE-IN READY! Welcome to this beautifully maintained, newer-construction home in the sought-after Magnolia Park community of Middletown. Built in 2019–2020, this spacious residence offers approximately 2,100 square feet of modern living space with an open-concept layout designed for today’s lifestyle. The bright and inviting main level features hardwood floors and a stylish kitchen with granite countertops, stainless-steel appliances, and a large center island—perfect for entertaining and everyday living. Upstairs are three generously sized bedrooms, including a spacious primary suite with a walk-in closet and a private bathroom with jacuzzi tub. Additional highlights include a finished lower level, convenient laundry area, private deck, and attached two-car garage. Enjoy low-maintenance community living with an HOA fee of $253 per month, which includes landscaping, snow removal, and access to desirable amenities, including 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. The seller is offering up to a $5,000 concession toward the buyer’s eligible closing costs** The property is completely vacant and ready for its next owner. Schedule your private showing today and take advantage of this immediate move-in opportunity!

19 Magnolia Park Road, Middletown

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