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

$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

$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

$559,999

3 Beds ⋅ 3 Baths ⋅ 1042301 MLS

Welcome to 7 Gillian Court, a beautifully maintained townhouse on a cul-de-sac, nestled in the sought-after gated community of Meadow Glen in Monroe. Offering the perfect blend of comfort, convenience, and community amenities, this spacious 3-bedroom, 2.5-bath home is ready to welcome its next owner to enjoy a low-maintenance lifestyle in a vibrant community. Drive up and park in your single car garage or leave your car in the driveway. Then step inside to a warm and inviting interior, featuring beautiful hardwood flooring, recessed lighting, crown molding, and an abundance of natural light. The generously sized and remodeled kitchen offers plenty of cabinetry and counter space, with new quartz countertop and backsplash, new kitchen sink, faucet and soap dispenser. The large pantry for additional storage makes everyday cooking and entertaining a breeze. The open and thoughtfully designed layout of the home provides plenty of room for both comfortable living and hosting guests. Step outside to your private patio, the perfect spot to enjoy summer grilling, morning coffee, or relaxing outdoors at the end of the day. Upstairs, the private primary suite offers a relaxing retreat complete with a luxurious jetted bath tub, double vanity, and walk-in closet. Two additional generously sized bedrooms provide flexibility for family, guests, a home office, or additional living space. Additional highlights include a lower level recreation room, central air, natural gas heating, natural gas fireplace, laundry room and ample storage. Recent improvements include updated flooring, newer appliances, a newer furnace, hot water heater, water softener, and A/C, offering peace of mind and easy living. Enjoy everything Meadow Glen has to offer, including a gated setting, community pool, clubhouse, fitness center, tennis court, playground, and beautifully maintained common areas. The location is equally appealing, with shopping, restaurants, public transportation, major roadways, and everyday conveniences close by. The Woodbury Commons, Route 17, the NYS Thruway, and transportation options toward NYC are all within easy reach.

7 Gillian Court, Monroe

$369,999

2 Beds ⋅ 3 Baths ⋅ 1036720 MLS

Welcome to Timber Hills in Monroe, NY! This spacious 2-bedroom, 2.5-bath condo offers a great opportunity to create a home that reflects your personal style in a desirable community within the Monroe-Woodbury School District. The main level features a comfortable living room, eat-in kitchen, separate dining room, convenient half bath, and access to a private deck—perfect for enjoying your morning coffee or relaxing outdoors. Upstairs, you'll find two generously sized bedrooms, including a primary suite with its own private bathroom and walk-in closet. The unfinished basement provides valuable additional space with a dedicated laundry area and plenty of room for storage, a workshop, home gym, or future finishing possibilities. The unit also includes two assigned parking spaces for added convenience. Residents of Timber Hills enjoy access to community amenities including a swimming pool, playground, basketball and tennis courts. Ideally located in Monroe with easy access to stores, major roadways and transportation for commuters to the NYC area, while still offering the benefits of suburban living. Don't miss the opportunity to make this Timber Hills condo your own!

41 Aldo Court, Monroe

$780,000

4 Beds ⋅ 3 Baths ⋅ 1034143 MLS

Check out the 3D walk through from the entire house on zillow you can find it by FACTS & FEATUES Virtual tour! 17 Oldwyck Cres - Original Owner Estate, Meticulously Maintained This is the one you’ve been waiting for. Loved since day one by its original owner, 17 Oldwyck Cres offers timeless quality, generous space, and thoughtful updates at every turn. Step Inside You are greeted by a grand two-story foyer with dramatic double-height ceilings that set an elegant tone from the moment you arrive. Gleaming hardwood floors lead you into the main living areas and carry warmth throughout the first floor. Main Level Living To your Left, a quiet home office provides the perfect work-from-home retreat with privacy and natural light. Flowing forward, the formal dining room impresses with space for large gatherings and holiday hosting. The heart of the home is the oversized living room, anchored by a classic wood-burning fireplace that invites cozy evenings and conversation. This opens to the true showstopper: an expansive extended great room. With soaring cathedral ceilings and walls of windows on three sides, the space is bathed in light all day and feels like a private sunlit sanctuary. Chef’s Kitchen & Outdoor Living The large kitchen is designed for entertaining. Stainless steel appliances, ample cabinetry, and two dedicated buffet stations make serving effortless. Step through to the oversized rear deck complete with built-in speakers. It’s ready for summer barbecues, morning coffee, or evening unwinds. A convenient main-floor laundry room keeps daily life easy. Upstairs Retreat Upstairs you will find four generous bedrooms. The primary suite is a true escape with room for a sitting area, walk-in Custom closets, and a spa-inspired bath featuring a deep soaking tub for relaxing after long days. The additional bedrooms are bright, spacious, and share a well-appointed full bath. Lower Level & Bonuses The fully finished walk-out basement extends your living space. A built-in Dry bar makes it ideal for movie nights, game days, or a guest suite. Build in Speakers in basement, With one side at ground level, it feels open and bright, not like a basement at all. Quality & Updates You Can Trust This home has been proactively maintained. Features include a whole-home central vacuum system and water filtration for clean living. Major systems are done: new roof 2025, water heater 2021, and upstairs AC 2021. A 2-car garage completes the package. This is more than a house. It’s a home where memories were made and where your next chapter begins. Key Systems Updated: Roof 2025 | Water Heater 2021 | Upstairs AC 2021- big shed in back of the house

17 Oldwyck Crescent, Highland Mills

$585,000

3 Beds ⋅ 3 Baths ⋅ 1030324 MLS

Check out this Home! 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

$299,999

3 Beds ⋅ 3 Baths ⋅ 1025157 MLS

Waterfront living at its finest! HEAT and HOT WATER Included. 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 VACATION!!!

402 Mountain Laurel Drive, Monroe

$249,900

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, brand new bathroom, new flooring, new windows and a new sliding glass door that opens to a nice size patio—perfect for relaxing or enjoying your morning coffee. Kitchen features granite countertops and tile backsplash. Lots of closet space. Also there are two new a/c units, washer and dryer in unit and large storage room in basement area of building. 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.

8 Heritage Drive Unit #E, Harriman

$260,000

2 Beds ⋅ 1 Baths ⋅ 1006554 MLS

Welcome Home! Well maintained two bedroom unit with lake and mountain views. Spacious living room with access to a private balcony. Eat in kitchen has updated counter tops and new appliances. Both bedrooms have ample closet space. Windridge is a quiet community conveniently located minutes from town. Great commuter location. Amenities include pool, playground, tennis and basketball courts, clubhouse. Heat and Hot Water included in the HOA & Low Taxes

804 Swan Hollow Road, Monroe

$865,000

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

$245,000

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

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