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

$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

$305,000

2 Beds ⋅ 2 Baths ⋅ 1044653 MLS

Welcome to 18 Deer Court Dr, located in the desirable Deer Run community. This well-appointed second floor end unit offers approximately 1,291sqft, with 2 bedrooms, and 2 full bathrooms. This spacious condo combines comfort, style, and convenience in a wonderful Hudson Valley setting. Step inside to an open and inviting living and dining area featuring beautiful hardwood floors, creating a warm and seamless space for both everyday living and entertaining. The kitchen is thoughtfully designed with stainless steel appliances and a granite pass-through window, opening the space to the living and dining areas while making entertaining and conversation effortless. The bathrooms are enhanced with granite countertops, adding a touch of elegance and durability. Other updates include a new water heater (2025), new washer and dryer (2025), and a well-maintained HVAC system (2019), providing modern convenience and peace of mind. As an end unit, this condo offers an added sense of privacy, while the large, deep attached garage (53’) provides exceptional storage and parking space. Residents of Deer Run can enjoy an array of community amenities, including a clubhouse, seasonal swimming pool, tennis courts, and pickleball courts. Garbage pickup is also included. Conveniently located near Rt. 17 and I-84, this home offers easy access to shopping, dining, recreation, commuting routes, and all that Middletown and the surrounding Hudson Valley have to offer. Come see everything this Deer Run condo has to offer. Schedule your private showing today!

18 Deer Court Drive, Middletown

$579,000

4 Beds ⋅ 3 Baths ⋅ 1038040 MLS

Welcome to Wildflower at Wallkill, Orange County's premier 55+ community! Something Special! This 4 BR, 3 bath beauty is open and sun filled with vaulted ceilings and lovely detailed chair railings! 10 ft. ceilings and new wood floors throughout 1 st floor! Large LR opens to DR! Kitchen with island and undercounter lighting opens to vaulted family room with gas fireplace! Primary suite is on first floor and has 2 large walk in closets. There's another BR and full bath on first floor! 2nd floor has a loft and 2 BRs and a full bath! Water heater is 2 years old! There's a whole house surge protector!

34 Hawthorne 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

$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

$278,000

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

$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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