Orange Homes with Tennis Court(s) Amenities

Welcome to Orange County, New York—a picturesque region that beautifully blends natural beauty with vibrant community life. Nestled in the heart of the Hudson Valley, Orange County is renowned for its stunning landscapes, rich history, and a wealth of recreational activities. From the rolling hills and lush forests to the charming towns of Warwick, Goshen, and Newburgh, residents enjoy a serene lifestyle just a short drive from the bustling energy of New York City.

One of the unique features of Orange County is its array of luxurious homes equipped with tennis court amenities. Imagine waking up to the gentle sounds of nature and stepping outside to your private tennis court, where you can enjoy a friendly match or practice your serve in the comfort of your own backyard. These homes cater not only to avid tennis players but also to those who appreciate the lifestyle that comes with such amenities.

Properties with tennis courts often feature expansive outdoor spaces, perfect for entertaining guests or enjoying family gatherings. Whether you're an experienced player or just looking to stay active, having a tennis court at your doorstep adds an unparalleled convenience to your daily routine.

Moreover, Orange County offers a wealth of cultural and recreational opportunities, from hiking and biking trails to local wineries and farmers' markets. With its combination of luxurious living and a vibrant community, Orange County is the perfect place to call home for those seeking both relaxation and an active lifestyle. Discover your dream home with tennis court amenities today and embrace the best of what Orange County has to offer!

Newest Orange Homes with Tennis Court(s) Amenities

$549,900

2 Beds ⋅ 3 Baths ⋅ 1049692 MLS

Enjoy the ease of main-level living with the bonus of a beautifully designed second floor in Wildflower at Wallkill, a gated 55+ active-adult community. Offering approximately 2,400 square feet, this spacious two-bedroom, two-and-a-half-bath home features an open, comfortable floor plan designed for both everyday living and entertaining. The main level welcomes you with generous living and dining areas filled with natural light and custom trim. At the heart of the home, the kitchen features granite countertops, custom backsplash, abundant cabinetry and an impressive nine-foot island with plenty of room for seating. Just beyond, a comfortable family room with a natural gas fireplace creates a warm gathering space and flows easily into the kitchen. Also located on the main level is the primary bedroom suite, offering the convenience of true one-level living. Upstairs, guests can enjoy their own private area with a second bedroom, full bath and a versatile flex space—perfect for a sitting area, home office, hobby space or quiet retreat. The private rear patio provides a lovely spot for morning coffee, gardening or relaxing outdoors. An attached two-car garage adds everyday convenience. Life at Wildflower at Wallkill extends well beyond the front door. Residents enjoy a gated community with indoor and outdoor pools, clubhouse, tennis and pickleball courts, exercise classes, organized trips and an active calendar of social activities. Shopping, restaurants, medical offices and everyday conveniences are all just minutes away.

6 Cyprus Drive, Middletown

$699,999

2 Beds ⋅ 4 Baths ⋅ 1046891 MLS

"Cambridge on the Course". Inviting, immaculate end-unit townhome in the sought after Woodlands at Tuxedo, where privacy, convenience and elegant living come together. This one-owner from new “Cambridge” design home is spacious and has rare and unique features; it is southeast facing and sun-soaked, flanked by open space lawn in front and seasonal golf course views to the rear. It boasts the rare combination of 1st floor luxury primary bedroom suite and a finished lower level for extended entertaining. The Cambridge offers an expansive open concept entry w/ 2-story soaring dining room with palladian capped windows. Adjacent is the living room with wood burning fireplace, and on the other flank, the beautiful eat in kitchen. The first floor primary owner’s suite is a haven of comfort and privacy; with a vaulted ceiling, a generous walk-in closet and tub/shower combo make it a relaxation retreat. The upstairs offers an additional bedroom and a flex room for office, a hall bath and a sitting room overlooking the gorgeous lower level. There's even a generous cedar closet on this level. Outside is a lovely back patio seasonally overlooking the famed, 4th hole of the R. Trent Jones designed Tuxedo Club Golf Course. Great privacy is also afforded when leaves are on the forested back view. The patio is perfect for entertaining, barbecuing and fresh air in all seasons. The lower-level basement is finished to a high standard and boasts efficiencies, counters, storage/cabinetry, and a half bath; it's cozy yet luxurious all at once. The 2-car garage maintains a gleaming, epoxy sealed floor, and 2-car, level driveway parking rounds out this special home. 3 zones heat and a/c, one for each level! Newer flooring in many areas. Turnkey luxury with approximately 3,000 sf over the 3 levels. The Woodlands at Tuxedo is approximately 1 hr to Manhattan, and inside 15 minutes to Bergen County, NJ, and yet you feel a world away. This well-established HOA community boasts outdoor tennis and swimming pool as well as a charming community clubhouse with exercise room and common areas. The community is adjacent to a town park for recreation, and nearby to Sterling Forest, with over 20,000 acres of forever preserved state forest and miles of nature trails.

10 Willow Court, Tuxedo Park

$269,900

2 Beds ⋅ 2 Baths ⋅ 1049236 MLS

Welcome home to this beautifully updated 2-bedroom end-unit townhouse offering the perfect blend of comfort, style, privacy, and convenience. This move-in ready home presents a rare opportunity to own a residence that has been lovingly maintained and thoughtfully updated throughout the years. Featuring gorgeous new flooring, a stunning new kitchen with modern finishes, beautifully renovated bathrooms, gas heat, and gas cooking, central air, every detail has been carefully curated for today's lifestyle. Now let's discuss LOCATION! Step outside to your own private outdoor retreat featuring an exceptional custom paver patio with brilliant hardscaping, creating the perfect setting for entertaining, dining al fresco, or simply relaxing while enjoying peaceful wooded views and added privacy. As an end unit backing to the woods, you'll appreciate the added sense of space and tranquility rarely found. You will also love your own carport. An exclusive space w/ added storage area. Additional parking is also available. Located in a highly desirable community with amenities galore, residents enjoy access to Woodbury Recreation, swimming pools, the reservoir, beach areas, playgrounds, sports courts, walking trails, and a variety of year-round activities and events. New York City commuter-friendly and ideally situated just minutes from Woodbury Common Premium Outlets, West Point Military Academy, Bear Mountain State Park, Harriman State Park, major highways, dining, shopping, and recreation. Whether you're searching for a full-time residence or a weekend retreat, this exceptional townhouse offers low-maintenance living and an unbeatable Hudson Valley lifestyle in a picturesque setting. Opportunities to purchase a one-owner home with this level of care, updates, privacy, and location are truly rare.

13 Redwood Drive, Highland Mills

$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

$675,000

3 Beds ⋅ 3 Baths ⋅ 1048171 MLS

Enjoy panoramic Hudson River views, including the historic Bannerman Island, from two private decks in the sought-after Plum Point community. This beautiful 3-bedroom, 2 1/2 bath condo has been extensively updated inside and out. Recent improvements include new roof (2025), renovated kitchen with added peninsula, bathrooms, newer windows and doors, updated flooring, newer hot water heater, and in-unit washer (brand new)and dryer. Skylights add natural light throughout. The spacious primary suite features its own river-facing deck, creating the perfect setting for morning coffee or unwinding at the end of the day. The remodeled primary bathroom features a tiled shower, double vanity, and whirlpool spa tub overlooking the river, plus a large walk-in closet with custom shelving and organizers. Enjoy the convenience of a one-car garage and private driveway parking, offering added ease for coming and going. Community amenities include pickleball, tennis, a large outdoor pool, clubhouse, playground, and basketball court. The location is ideally situated approximately 8.5 miles from Metro-North's NYC train service and just 55 miles from the George Washington Bridge, offering a wonderful balance of peaceful Hudson River living and accessibility to New York City. Whether you're looking for a full-time residence, weekend getaway, or a place to enjoy the beauty of the Hudson Valley, this exceptional condo delivers views, space, updates, amenities, and convenience, all in one remarkable setting.

272 Tamerisk Lane, New Windsor

$349,000

3 Beds ⋅ 2 Baths ⋅ 1047470 MLS

Welcome home to this inviting 3-bedroom, 2-full-bath condominium in the Town of Monroe! Featuring a comfortable layout with a cozy fireplace and a kitchen that opens directly to the deck, creating the perfect space for morning coffee, outdoor dining, or relaxing after a long day. The full basement offers excellent potential to create additional living space, a home office, recreation room, gym, or whatever best suits your needs. Enjoy all that this wonderful community has to offer, including a swimming pool, tennis court, and park. Ideally located close to shopping, restaurants, parks, and lakes, with the popular Woodbury Common Premium Outlets just minutes away. Whether you’re looking for a place to call home or a convenient Hudson Valley lifestyle, this condominium offers space, amenities, and a location you’ll love! H&B due 9/14 5pm!!

42 Natale Court Unit #42, Monroe

$370,000

3 Beds ⋅ 2 Baths ⋅ 1046996 MLS

Move right in! This beautifully maintained and thoughtfully updated 3-bedroom, 2-full-bath END-UNIT condo offers almost 1,400 square feet of comfortable, easy one-level living in the desirable Whispering Hills community. As soon as you enter the welcoming two-story foyer, you’ll appreciate how bright, open, and impeccably maintained this home is. The spacious open-concept living area features vaulted ceilings and a beautiful Marble & Wood fireplace, creating a warm, inviting atmosphere. Sliding doors lead to your private deck provides easy access to enjoy the peaceful, beautifully landscaped surroundings. The renovated kitchen is both stylish and functional, featuring modern cabinetry, granite countertops, updated backsplash, Stainless appliances and a pantry with plenty of shelving, The spacious primary suite is truly a standout! Enjoy a large walk-in closet with California shelving and a renovated full bath frameless shower. Two additional bedrooms provide plenty of flexibility for guests, a home office, or other needs. Additional updates include sparkling new flooring throughout, new water heater & Washer/Dryer. The attached one-car garage provides convenient direct access to the home along with dedicated storage space. Enjoy all that Whispering Hills has to offer, including a two community pools, tennis court, kids park, dog park, sidewalks, and a peaceful setting—while being just minutes from shopping, restaurants, parks, and major commuter routes. Located in the Chester School District. All this with New York City bus that picks up and drops off right in the complex. Don't miss your opportunity to make it yours. Call today for your private tour. *****Professional Photos Coming Soon****

3211 Whispering Hills, Chester

$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

$719,990

3 Beds ⋅ 4 Baths ⋅ 1043485 MLS

The Perfect Home. The Perfect Time. LOWER YOUR RATE, LOWER YOUR PAYMENT! Ask about special financing! The Countdown Is On! Don't miss this rare opportunity to own the highly sought-after Pershing at Tuxedo Reserve with a September move-in. Offering 2,383 square feet of beautifully designed living space, this townhome features 3 bedrooms, 3 full baths, 1 half bath, and a 2-car garage. The open-concept layout is perfect for both entertaining and everyday living, highlighted by hardwood flooring, a private home office, and a designer kitchen with quartz countertops, soft-close cabinetry, and ample storage. Upstairs, the spacious primary suite boasts a large walk-in closet and private bath, complemented by two additional bedrooms and a convenient laundry room. The entry-level bonus room with a full bath provides endless flexibility for guests, a fitness space, media room, or home office. Enjoy resort-style amenities including a clubhouse, outdoor pool, fitness center, tennis and pickleball courts, dog park, soccer field, playground, and more. Limited quick move-in opportunities remain in this desirable community. Secure your new home today before it's gone!

142 Pine Ridge Road, Tuxedo Park

$299,000

2 Beds ⋅ 1 Baths ⋅ 1042658 MLS

Welcome to Whispering Hills! This inviting end-unit home offers a comfortable blend of everyday living, privacy, and convenience. Enjoy easy access to major commuter routes and highways, making this an ideal choice for commuters seeking the comfort of home without sacrificing convenience. Come home to a welcoming community and enjoy all that this convenient location has to offer.

2124 Whispering Hills, Chester

$485,000

3 Beds ⋅ 3 Baths ⋅ 1042554 MLS

Welcome to your new home in The Grove — a highly sought-after Condo Community in New Windsor, NY. This beautifully updated and maintained Townhouse provides an expansive floorplan covering 3 levels with 1,910 sq ft of living space including a Finished Basement. The Entryway opens right up to the open concept living area in the level above and down to the finished Basement below . Take in the gorgeous main floor with high ceilings and oversized windows that brightens the entire living room with natural lighting. The gorgeous hardwood floors continue into the formal Dining Area just off both the Living Room and the Kitchen creating a natural flow. The Kitchen features a waterfall Quartz corner island with stools, stainless steel appliances, an eat-in dining nook and glass sliding doors that lead out to a small deck in the backyard. Upstairs are three generous sized bedrooms including the spacious Primary Bedroom Suite that has a large walk-in closet and a spa-like ensuite bathroom with a jetted tub, glass door shower, and double sink vanity. On the other side of the landing are the 2 remaining Bedrooms with big windows, great closet space and share the hallway Full Bathroom with a bathtub. On the lower level is the Laundry Room and Finished Basement that adds valuable flexible living space — perfect for a rec room, home office, or gym. The Basement also conveniently provides access to the 2 Car Garage with additional space for storage. Bonus of being a Resident at The Grove is access to the Clubhouse, a Fitness center, an In-Ground Pool, and a Tennis court, plus ample guest parking throughout the community. Commuters will love being just 10 minutes from the train station and only 5 minutes to Stewart International Airport — making travel for work or pleasure effortless. New Windsor's central location also means easy access to Washingtonville, Middletown, Newburgh, Goshen, and Beacon, putting shopping, dining, and everyday errands in every direction in under 25 minutes. Beyond the convenience, you're perfectly positioned to enjoy everything the Hudson Valley has to offer: scenic state parks and hiking trails, charming small towns full of local shops and restaurants, and some of the region's best breweries and wineries just a short drive away. Hop over the Beacon Bridge and you've got the entire east side of the Hudson Valley open to you as well — including the shops, galleries, and eateries of Beacon itself. Commuter-friendly, centrally located, and surrounded by everything that makes the Hudson Valley special — this location truly has it all!

806 Hawthorn Way, New Windsor

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