Middletown Homes with Tennis Court(s) Amenities

Welcome to Middletown, New York – a vibrant city nestled in the heart of Orange County. Known for its rich history and picturesque landscapes, Middletown offers a delightful blend of suburban charm and urban conveniences. With its close-knit community, diverse dining options, and an array of recreational activities, it’s no wonder that families and individuals alike are drawn to this enchanting locale.

For those who cherish an active lifestyle, Middletown stands out with its unique selection of homes featuring tennis court amenities. Imagine stepping outside your door to find your very own private court, where you can enjoy a friendly match or hone your skills in the comfort of your backyard. These properties not only cater to tennis enthusiasts but also provide a perfect setting for entertaining guests or enjoying family gatherings.

The homes in Middletown are as diverse as its residents, ranging from charming single-family houses to modern estates, each offering unique architectural styles and spacious layouts. Many of these homes with tennis courts are located in serene neighborhoods, surrounded by lush greenery and stunning views, creating a peaceful retreat from the hustle and bustle of city life.

Living in Middletown means you’re never far from outdoor adventures, with nearby parks, hiking trails, and recreational facilities. Plus, with excellent schools and convenient access to shopping and dining, you’ll find everything you need just a stone’s throw away.

Discover the perfect blend of luxury and leisure in Middletown, NY, where your dream home with a tennis court awaits!

Newest Middletown Homes with Tennis Court(s) 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

$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

$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.