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

$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

$245,000

2 Beds ⋅ 2 Baths ⋅ 1010150 MLS

Prime Location in Sought-After Hillside Village – Goshen School District! Welcome to this first-floor, end-unit 2-bedroom, 2-full bath condo in the desirable gated community of Hillside Village. Offering the convenience of one-level living, this home features a galley kitchen with an abundance of cabinetry, and a spacious living room with sliding glass doors leading to a private patio—perfect for relaxing or enjoying your morning coffee. The original dining area has been thoughtfully converted into a versatile home office or den, creating flexible living space to suit today's lifestyle. The primary suite offers a walk-in closet and a private ensuite full bath, while the second bedroom is ideal for guests or additional workspace. A large-capacity stackable washer and dryer are conveniently located in the hallway, along with additional storage. Three wall air-conditioning units and ceiling fans help keep the home comfortable throughout the warmer months. The low HOA fee includes lawn care, snow removal, water, sewer, and garbage service, allowing for low-maintenance living. One assigned parking space and ample guest parking add to the home's convenience. This property presents an excellent opportunity for buyers looking to personalize a home to their own taste. While it does require updating and TLC, it offers tremendous potential and is being sold As Is, including all appliances. Ideally situated in an excellent commuter location, you'll be just minutes from Metro-North, Garnet Health Medical Center, medical offices, shopping, the Galleria at Crystal Run, restaurants, and grocery stores. Whether you're a first-time buyer, downsizing, or seeking an investment opportunity, this condo offers outstanding value in a highly desirable location. The low HOA fee covers lawn care, snow removal, water/sewer, and garbage services. The home does need updating and TLC—perfect for buyers ready to bring their vision and create the home of their dreams. Home and appliances are being sold “As Is.” Enjoy a peaceful setting with one reserved parking space and ample guest parking. This excellent commuter location is close to the Metro-North train station, Garnet Health Medical Center, medical offices, shopping, the Galleria Mall, restaurants, and grocery stores.

100 Hillside Drive Unit #C6, 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

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