Monroe-Woodbury Homes with Tennis Court(s) Amenities

Welcome to the enchanting Monroe-Woodbury School District, nestled in the picturesque Orange County, New York. Renowned for its commitment to educational excellence, this district is a shining gem within the Hudson Valley region. Families are drawn here not only for the top-notch academic programs but also for the vibrant community spirit that fosters growth and creativity among students. The Monroe-Woodbury School District prides itself on a diverse array of extracurricular activities, state-of-the-art facilities, and dedicated educators who inspire students to reach their fullest potential. With a strong emphasis on both academics and personal development, it’s no wonder that parents choose to call this area home.

For those who appreciate an active lifestyle, the real estate offerings in Monroe-Woodbury include stunning homes with tennis court amenities. Imagine waking up in a beautiful residence that boasts its own private tennis court, where you can enjoy morning matches with friends or family, or simply unwind in the serene surroundings. These homes are perfect for tennis enthusiasts and those who value outdoor recreation, providing a unique blend of luxury and leisure right in your backyard.

Living in Monroe-Woodbury means more than just having a beautiful home; it’s about becoming part of a community that values education, sports, and family. Whether you’re drawn to the excellent schools or the inviting homes with tennis courts, this area offers a lifestyle that combines comfort, convenience, and a sense of belonging. Come explore the possibilities and discover your dream home in this vibrant community!

Newest Monroe-Woodbury Homes with Tennis Court(s) Amenities

$585,000

3 Beds ⋅ 3 Baths ⋅ 1030324 MLS

Welcome to Meadow Glen, Monroe's premier gated community, where luxury, comfort, and convenience come together in one exceptional home. This beautifully maintained and extensively upgraded largest-model end unit offers an abundance of natural light through 24 oversized windows, each enhanced with elegant Hunter Douglas Country Wood blinds, creating a bright and inviting atmosphere throughout. Designed for both everyday living and effortless entertaining, the spacious open floor plan features a dramatic two-story family room, formal living room, elegant dining room, and a gourmet kitchen equipped with Corian countertops, a breakfast bar, GE Profile stainless steel appliances, 42-inch cabinetry with convenient pull-out drawers, and a classic subway tile backsplash. Upstairs, the luxurious primary suite provides a peaceful retreat with a soaring cathedral ceiling, dual walk-in closets, and a spa-inspired ensuite bath featuring a frameless glass shower, large soaking tub and duel sinks. Two additional generously sized bedrooms, each with double closets, a full hallway bath, and the convenience of a second-floor laundry room complete the upper level. Rich hardwood flooring extends throughout both the first and second floors, adding warmth and timeless elegance. The fully finished walk-out basement significantly expands the living space with full-size windows, a sliding glass door leading to a private patio, a large recreation or media area, and additional storage—perfect for entertaining, working from home, or creating the ultimate family gathering space. Additional highlights include an attached garage with direct first-floor entry (no stairs), a double-wide driveway for ample parking, and a private outdoor setting rarely found in townhouse living. Residents of Meadow Glen enjoy resort-style amenities, beautifully maintained grounds, and a secure gated entrance, all while being conveniently located near shopping, restaurants, parks, major highways, and commuter transportation. This is a rare opportunity to own one of the most desirable homes in one of Monroe's most sought-after communities. Schedule your private showing today and experience the lifestyle you've been waiting for.

116 Barr Lane, Monroe

$250,000

2 Beds ⋅ 2 Baths ⋅ 1027933 MLS

Move right into this condo. This two bedroom unit features newer window and slider, Stainless Appliances, Two full renovated bathrooms and washer/dryer in unit. Mountain views. Complex has a inground pool and brand new tennis/pickleball courts. Close to Woodbury Commons, West Point Military Academy, Bear Mountain state park, wineries, hiking trails and close to Bus & Train transportation to New York City.

21 Lexington Hill Unit #3, Harriman

$374,000

3 Beds ⋅ 3 Baths ⋅ 1025157 MLS

Waterfront living at its finest! Welcome to this beautifully maintained center-unit townhome in one of Monroe's most sought-after communities. Offering over 1,800 square feet of living space, this home features 3 bedrooms, 2 full bathrooms, 1 half bath, and breathtaking lake views right from your backyard. The updated eat-in kitchen is the heart of the home, showcasing a center island, newer appliances, stylish backsplash, and a large picture window overlooking the tranquil lake. The open-concept layout flows seamlessly into the dining and living areas, making it ideal for everyday living and entertaining. The spacious primary suite easily accommodates a king sized bedroom set and includes a private ensuite bath. Two additional generously sized bedrooms and another full bath complete the upper level. The finished lower level provides exceptional flexibility with multiple finished rooms perfect for a family room, home office, fitness area, playroom, or guest space. Step outside and enjoy peaceful mornings or relaxing evenings overlooking the lake from your own backyard. Residents enjoy outstanding community amenities, including two swimming pools, two playgrounds, tennis courts, basketball courts, and a lake for fishing, paddle boarding, kayaking and a dedicated dog park—all included through the homeowners association. The monthly HOA fee includes heating, hot water, trash, lawn maintenance, sewer, roof, and siding. Conveniently located near shopping, restaurants, parks, schools, major highways, and public transportation, this home offers the perfect combination of scenic waterfront living and everyday convenience. Don't miss the opportunity to own this exceptional waterfront home in beautiful Monroe! Live where you want to VACTION!!!

402 Mountain Laurel Drive, Monroe

$279,900

1 Beds ⋅ 1 Baths ⋅ 1018246 MLS

Welcome to this beautifully maintained 1-bedroom, 1-bath condominium in excellent condition. This bright and inviting home features, new flooring, brand-new windows and a new sliding glass door that opens to a nice size patio—perfect for relaxing or enjoying your morning coffee. Conveniently located near major highways, public bus routes, the train station, and a variety of shopping, dining, and everyday conveniences, this condo offers the ideal combination of comfort, quality, and accessibility. Whether you're a first-time buyer, downsizing, or looking for a low-maintenance lifestyle, this move-in-ready home is a wonderful opportunity. There is a temporary special assessment of $150 a month for roofs and siding in addition to the HOA.

8 Heritage Drive Unit #E, Harriman

$255,000

2 Beds ⋅ 2 Baths ⋅ 1021526 MLS

Welcome to this beautifully maintained first-floor end-unit condominium in the highly desirable Lexington Hills community. Offering the ease and convenience of one-level living, this bright and spacious home welcomes you with an inviting foyer that leads to an open-concept living room featuring a cozy fireplace and sliding glass doors opening to a patio—perfect for relaxing or enjoying the outdoors. The kitchen offers wood cabinetry, granite countertops, a refrigerator approximately two years old, and includes a dishwasher that has never been used and is ready to be connected.. A kitchen window fills the space with natural light, enhancing the bright and airy feel throughout the home. Adjacent to the living room is a versatile bonus room that can serve as a home office, den, dining room, or hobby space. A hallway leads to the primary bedroom, complete with a walk-in closet and private en-suite bath. A second bedroom and an additional full bathroom, which conveniently includes a washer and dryer (approximately two years old), provide comfort and functionality for family or guests. Beautiful hardwood floors, installed in June 2026, add warmth and elegance throughout much of the home. The hot water heater was replaced approximately two years ago, providing added peace of mind. Parking is assigned in-front of the building with ample additional unmarked spaces for guests and family. Residents of Lexington Hills enjoy exceptional community amenities, including a swimming pool and tennis courts. Ideally located just minutes from the Harriman train station, major commuter routes, and the renowned Woodbury Common Premium Outlets, this home offers outstanding convenience for commuters and shoppers alike. Outdoor enthusiasts will appreciate the close proximity to Bear Mountain State Park, offering year-round recreational activities. Located within the highly regarded Monroe-Woodbury School District, known for its academic excellence, this move-in-ready home offers the perfect combination of comfort, convenience, and location.

27 Lexington Hill Unit #8, Harriman

$699,000

4 Beds ⋅ 3 Baths ⋅ 1015588 MLS

Welcome home to this bright, beautifully maintained colonial tucked into a quiet corner of Brigadoon. A welcoming foyer leads into an open, airy main floor with gleaming hardwood floors throughout. The formal dining room connects to the kitchen via a convenient butler's pantry, perfect for entertaining, while the living room centers around a cozy fireplace for those cooler months. A flexible main floor room offers space for a home office or whatever suits your needs, and the main floor laundry connects directly to the 2-car garage for everyday convenience. Upstairs, the spacious primary suite impresses with two walk-in closets and a beautifully renovated master shower, joined by three additional well-sized bedrooms and a full bath. The walk-out basement adds valuable extra living area, and the private yard backs up to a peaceful, wooded view, all on a low-traffic circular street that's ideal for kids and quiet evenings alike. Residents enjoy community amenities including a pool, tennis courts, and playground, plus easy access to Woodbury's parks, beaches, and reservoir. With NYC transportation, Woodbury Common, and West Point all just minutes away, this home offers the perfect balance of comfort, space, and convenience.

5 Oldwyck Crescent, Highland Mills

$289,000

2 Beds ⋅ 2 Baths ⋅ 1014150 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

$379,900

3 Beds ⋅ 2 Baths ⋅ 1002400 MLS

Welcome to this spacious 3-bedroom, 2-bath townhouse in the desirable Timber Ridge Community of Highland Mills, located within the Monroe-Woodbury School District. This home combines comfortable interior living, valuable updates, and access to an impressive collection of community amenities. Buyers searching for a townhouse with a finished basement, home with a walk-in closet, property with a deck, or townhome near commuter transportation will appreciate everything this home has to offer. The main level features an open-concept living and dining area with updated flooring, recessed lighting, and a functional layout designed for everyday living and entertaining. Sliding glass doors lead to a private deck surrounded by mature trees, creating an inviting outdoor space to relax, dine outdoors, or enjoy the natural wooded setting. The spacious primary suite offers a walk-in closet and direct access to a full bath, while two additional bedrooms provide flexibility for guests, a home office, or other household needs. The finished lower level expands the living space with the third bedroom, a large recreation room that can serve as a media room, fitness area, playroom, home office, or multi-purpose gathering space, and laundry room. An expansive unfinished storage area offers excellent room for seasonal items, hobbies, workshop space, or future customization. Residents enjoy Timber Ridge's private community amenities, including a pool, tennis and basketball courts, playground, and recreational areas, as well as access to the Town of Woodbury's resident-only recreation facilities featuring beach and lake access at Earl Reservoir, the John P. Burke Memorial Pool, sports fields, walking trails, and more. Conveniently located near shopping, parks, schools, train service, and major commuter routes, this property offers an exceptional opportunity to enjoy the Highland Mills lifestyle.

2 Acorn Court, Highland Mills

$895,000

4 Beds ⋅ 4 Baths ⋅ 997814 MLS

Welcome to this beautifully maintained Colonial located in the highly desirable Brigadoon neighborhood, perfectly situated on a quiet cul-de-sac and set on 1.9 private acres. This spacious and move-in-ready home offers 4 bedrooms, 3.5 bathrooms, and an ideal layout for both everyday living and entertaining. The main level features a stunning great room, formal living room, cozy family room, private office, and an expansive eat-in kitchen complete with granite countertops, cherry wood cabinets and flooring, stainless steel appliances, center island, and a convenient butler’s service area. Step outside to your own backyard retreat featuring two decks and a beautiful paver patio — perfect for entertaining or enjoying peaceful outdoor living. Additional highlights include crown molding throughout, a newly renovated finished basement ideal for gatherings or recreation, security system, sprinkler system, two-car garage, and ample street parking. Combining space, comfort, and an unbeatable location, this exceptional home is truly a must-see.

3 Braemar Way, Highland Mills

$250,000

2 Beds ⋅ 2 Baths ⋅ 984536 MLS

Find your perfect home in the heart of Lexington Hills with this desirable lower-level Unit. Experience the best of community living with the added benefit of a secluded, quiet location. Ideal for simplifying life, this unit offers turn-key readiness and is situated just moments from local dining, shopping, and major commuter routes. Enjoy the ease of a lower-level residence with excellent accessibility offering unparalleled convenience and quiet living. This end unit is perfect for buyers seeking an accessible, easy-to-manage home or a smart investment opportunity. Enjoy hassle-free living in a desirable community setting.

18 Lexington Hill Unit #8, Harriman

$424,999

3 Beds ⋅ 3 Baths ⋅ 987125 MLS

Welcome to this beautifully maintained end-unit townhouse in Highland Mills, offering the perfect blend of space, privacy, and modern updates. As an end unit, the home enjoys added natural light and enhanced privacy. Thoughtfully updated and well cared for, this property is ideal for buyers seeking low-maintenance living with high-end improvements. This 3-bedroom home features two spacious en-suite bedrooms, each with its own recently renovated bathroom showcasing stylish, contemporary finishes. Common bathroom is fully gutted and currently undergoing a complete renovation, this bathroom will be delivered entirely brand new from top to bottom. Planned updates include all-new walls, a modern shower, new vanity, mirror, and toilet—offering a fresh, clean, and contemporary space for the future owner. Perfect opportunity to enjoy a fully updated bathroom with no detail overlooked. This home has already been updated throughout, this home features brand-new flooring, fresh paint, modern ceiling fans, and newly installed closet systems, offering a stylish and is move-in-ready. Located within the Monroe-Woodbury Central School District, residents also have access to Woodbury Parks and Recreation—exclusively available to Woodbury residents—offering parks, pools, sports programs, and year-round community activities. Perfect for commuters, this home is just minutes to public transportation, minutes away to the New York State Thruway (I-87), and to the Palisades Parkway, and less than 5 miles to Woodbury Common Premium Outlets. New York City is approximately 50 miles away, making this an ideal location for both convenience and lifestyle. Enjoy all that the Hudson Valley has to offer with close proximity to United States Military Academy, Legoland, World Resort Casino, and Harriman State Park. Explore countless scenic hiking and biking trails, nearby ski mountains, charming local farms, distilleries, and wineries—offering year-round recreation and a true lifestyle destination right at your doorstep.

8 Laurel Court, Highland Mills

$259,000

2 Beds ⋅ 2 Baths ⋅ 983094 MLS

PRICED TO SELL - 2 Bed | 2 Bath | Top-End Unit | Monroe-Woodbury Schools | Stunning Views condo with some of the best views in the Lexington Hills community. Prime Location - Perfect for commuters and outdoor enthusiasts alike: 45 minutes to NYC by train (train station within walking distance), 55 minutes to NYC by car 10 min to Grocery/shop's New updates in the last 2 years 1) New Deck 2) New Roof & skylights 3) New water heater 4) New piping etc in the boiler room 5) New washer/Dryer 6) New AC's 7) updated bathrooms 8) New kitchen flooring Key points 1) Top floor end unit - great natural lighting, stunning views 2) Top floor - don't hear other people's footsteps all night 3) Parking - additional open spots in the parking lot across from us. 4) close to pool 5) close to entrance - easy to get in and out with snow. The HOA provides exceptional value by covering many major services, including: 1) Water 2) Exterior maintenance and repair 3) Trash removal 4) Snow removal 5) Landscaping Enjoy exclusive access to the community pool, clubhouse, tennis courts, and playgrounds

2 Lexington Hill Unit #12, Harriman

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