Monroe-Woodbury Homes with Park Amenities

Welcome to the Monroe-Woodbury School District, an exceptional educational hub nestled in the picturesque Orange County of New York. Renowned for its commitment to academic excellence and holistic student development, this district serves a vibrant community that values education as a cornerstone for future success. With a diverse array of programs, dedicated educators, and a strong emphasis on extracurricular activities, Monroe-Woodbury offers an enriching environment for students of all ages.

Families residing in this area can take pride in knowing that their children are part of a school district that consistently ranks among the top in the state. The district encompasses several elementary, middle, and high schools, each equipped with modern facilities and resources designed to foster creativity and critical thinking. With a focus on preparing students for college and careers, Monroe-Woodbury encourages a culture of innovation and collaboration, ensuring that every child has the opportunity to thrive.

In addition to its outstanding educational offerings, the Monroe-Woodbury area boasts beautiful homes that come with park amenities, perfect for families who cherish outdoor activities. Imagine living in a charming neighborhood where your children can play in well-maintained parks, enjoy walking trails, and participate in community events. These homes provide not just a place to live, but a lifestyle enriched by nature and community spirit.

Whether you’re looking for a cozy single-family home or a spacious residence with ample outdoor space, Monroe-Woodbury has something for everyone. Discover the perfect blend of top-notch education and vibrant living in this delightful corner of New York!

Newest Monroe-Woodbury Homes with Park Amenities

$498,000

3 Beds ⋅ 3 Baths ⋅ 1027087 MLS

Nestled on a quiet cul-de-sac, this beautifully maintained townhome offers spacious rooms, thoughtful details, and a wonderful townhome community setting. The open plan living and dining room combination features a marble gas fireplace, wood floors and walls of windows. The eat-in kitchen provides abundant counter space; sliding glass doors leading out to the enormous Trex deck make three seasons entertaining easy. Upstairs, the primary bedroom suite features 9-foot ceilings, a lovely palladian window, en suite private bath, and walk-in closet. Two additional bedrooms offer generous double closets, and the hall bath serves both. A finished lower level family room adds great additional space and is currently used as a music studio. The two car garage has added built in storage plus a custom closet was added under the stairs. Over $80k of improvements in the past few years include renovated kitchen with granite/stainless/new backsplash, water softener, new roof, new widened driveway (2025) with Belgian block and parking for 2+ additional cars. Enjoy a community filled with activities for family and friends, including scenic walking trails, lake access with a sandy beach, and a peaceful country feel, all while remaining close to shopping, dining, and conveniences, including the destination mecca Woodbury Common. Commuting to NYC is easy by train or bus. Taxes with STAR approximately $9,919.

1 Ledger View Court, Highland Mills

$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

$275,000

2 Beds ⋅ 1 Baths ⋅ 1022387 MLS

"ELEVATED ESCAPE" - There is a particular kind of life that unfolds in the Hudson Valley foothills - unhurried mornings, the smell of woodsmoke, a sky uninterrupted by steel and glass - and yet never more than an hour from the pulse of New York City. This renovated two-bedroom, one-bath condominium in the Tuxedo Heights community of Southfields, New York, sits precisely at that intersection, where the Ramapo Mountains meet the reality of modern commuter life. With direct access to Route 17 and train service into Penn Station, Manhattan is a remarkably easy reach, making this an ideal retreat for those who want to leave the city behind without ever truly leaving it. The residence itself has been thoughtfully updated, with a renovated eat-in kitchen that invites leisurely weekend breakfasts and easy entertaining alike. A wood-burning fireplace anchors the living space, lending warmth and character that newer construction rarely achieves. What sets this unit apart from others in the building is something deceptively practical and genuinely rare: fully interior access to a private garage and storage room, a luxury in any climate, and one that speaks to the care with which this home was considered. An additional parking space in front of the building rounds out the convenience. Two private outdoor spaces - a front balcony ideal for morning coffee and a generously sized rear deck suited to summer grilling - frame sweeping views of the surrounding mountains, the kind of views that remind you, each time, why you chose to live here. Tuxedo and the wider Orange County landscape offer an extraordinary range of outdoor pursuits that the region's devotees return to year after year. Harriman State Park, practically at the doorstep, offers more than 200 miles of hiking and biking trails winding through hardwood forest and over exposed ridgelines. Tuxedo Lake itself is a fixture of the local calendar, while nearby Sterling Forest State Park draws naturalists and casual walkers in equal measure. Come autumn, the orchards of Orange County - from Warwick to Pine Island - become destinations in their own right, with apple picking, farm stands, and cideries that draw visitors from across the tristate area. Conveniently located minutes from the Tuxedo train station, NYC bus stop and major highways making commuting a breeze. Located in Monroe-Woodbury School District. The Black Dirt region, a short drive west, is one of the most productive agricultural corridors in the Northeast, and its farm-to-table culture has quietly made this corner of New York a serious food destination. For those who prefer their outdoor recreation with a side of retail, Woodbury Common Premium Outlets is minutes away - a point of convenience that never seems to grow old. The full-service HOA handles the maintenance and management that often accompany homeownership, allowing residents to inhabit the space rather than tend to it. HOA has plans to re-do community pool. In a market where true turnkey rarely means what it implies, this is a home that earns the designation - a mountain sanctuary, a commuter's asset, and a place that simply feels like somewhere worth coming home to.

205 Old Mill Road, Southfields

$900,000

4 Beds ⋅ 2 Baths ⋅ 997767 MLS

Rare opportunity to purchase this gorgeous property that consists of 3 homes nestled on 3.5 beautiful acres. The main Colonial residence has been gutted and will need to be renovated/rebuilt, however, you can live in one of the additional two residences while you renovate! The 2nd residence called the “stone cottage” has 2 fieldstone fireplaces, a full kitchen, a vaulted ceiling in the bedroom, a washer/dryer, and a full bath. The 3rd residence is called the “white cottage” and sits atop the highest point on the property. This charming cottage has 2/3 bedrooms, a large kitchen, a full bath, and a new 400 sq ft Trex deck with custom railings that is totally private to enjoy the 3.5 acres of trees and woods. Perfect opportunity to rent out the additional homes and have the property pay for itself. The property has all this to offer, stone walls surrounding the compound, 50,000-gallon custom built gunite in-ground pool with glass tile, patios overlooking the gorgeous park-like grounds, and a tennis/pickleball/basketball sports court. All this and you also have lake rights and the property is located in the sought after Village of Monroe near Mill Pond with Monroe-Woodbury Schools. Fantastic commuter location, close to restaurants, quaint boutiques, farmers markets, wineries, shopping, state parks, 50 miles to NYC, near 84, 87, 17, Metro North/ NJ Transit & buses to NYC, Stewart & West Point. Schedule to see it now, this one will not last. Owner open to creative offers and/or partnering on renovation and sale!

651 Lakes Road, Monroe

$579,000

3 Beds ⋅ 3 Baths ⋅ 1002251 MLS

Beautifully maintained and thoughtfully designed, this warm and inviting home is nestled within a sought-after gated community on a quiet, private cul-de-sac. From the moment you step inside, you’ll feel the light, and positive energy that fills this inviting home. Sunlight pours through the windows, creating a bright and airy atmosphere that feels both uplifting and comfortable. The main level features a cozy gas fireplace in the living room, a formal dining room ideal for entertaining, and a spacious well-appointed kitchen with a center island. Hardwood floors throughout add warmth and timeless elegance. Flexible spaces throughout the home provide options for a home office, playroom, guest space, or gym, allowing the home to adapt to your needs. The upper level includes spacious bedrooms and a comfortable primary suite with ample storage. Additional highlights include central air, an ADT security system, a large basement offering excellent storage space, a newer hot water tank (2019), and an attached one-car garage for everyday convenience. Enjoy low-maintenance living with resort-style amenities including a pool, tennis courts, clubhouse, gym, and tot lot. The HOA covers water, snow removal, lawn maintenance, and garbage pickup, allowing you to spend more time enjoying everything this community has to offer. Conveniently located just minutes from public transportation and the shopping and dining at Woodbury Commons, this exceptional home combines comfort, convenience, and effortless living. Don’t miss the opportunity to make it yours.

13 Gillian Court, Monroe

$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

$349,900

3 Beds ⋅ 2 Baths ⋅ 997661 MLS

Welcome to this charming corner-lot townhome in the desirable Town of Woodbury! This spacious 3-bedroom, 2-full-bath home offers the perfect blend of comfort, convenience, and style. The bright and inviting living area features a semi-open layout ideal for both everyday living and entertaining. The kitchen offers plenty of counter space and cabinetry, while the dining area flows seamlessly to the outdoors—perfect for summer gatherings or relaxing evenings. The primary bedroom suite provides a peaceful retreat with its own full bath, and two additional bedrooms offer flexibility for guests, a home office, or hobby space. Situated on a corner lot, the home enjoys extra yard space and added privacy. Located in a prime area of Woodbury, you’ll have access to the Woodbury Recreation facilities, Monroe-Woodbury schools, and an easy commute via major highways, shopping, and restaurants just minutes away. Don’t miss this opportunity to own a beautiful, well-maintained townhome in one of Orange County’s most sought-after communities!

30 Sycamore Court, Highland Mills

$150,000

997053 MLS

Discover the perfect opportunity to build your dream home on Walton Terrace in Monroe! Nestled in a quiet, already-developed residential area, this beautiful property sits on approximately 1/4 acre and offers exclusive lake rights. Located within the highly desirable Monroe-Woodbury Central School District, this rare find perfectly combines tranquility, natural beauty, and everyday convenience. This commuter-friendly location provides easy access to major highways and nearby transportation, making it ideal for those traveling throughout the Hudson Valley or into NYC. Monroe’s charming downtown offers quaint shops, restaurants, a beautiful lake setting, and fun, friendly community events throughout the year that truly make this town special. This property is a rare opportunity to create the custom home you’ve always envisioned while enjoying lake living in one of the area’s most sought-after communities. Act now and make your dream a reality!

Walton Terr/Lakes Terrace, Monroe

$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

$849,000

6 Beds ⋅ 5 Baths ⋅ 976525 MLS

This high-impact, move-in-ready luxury home delivers instant appeal on 1.5 private, park-like acres. Designed to impress, it features vaulted ceilings, rich Brazilian wood floors, a granite kitchen, and a fireplace that anchors the space with warmth and style. The flexible layout offers 2 bedrooms plus an office on the main level—perfect for guests or extended living—while upstairs includes a spacious primary suite and 3 additional bedrooms. Step outside to a large patio, covered porch, and beautifully landscaped grounds with a scenic brook—ideal for relaxing or entertaining. A rare combination of luxury, space, and setting—don’t miss this one. *Appliances shown are included. If the buyer is interested in purchasing any furnishings, we’re happy to discuss available options.

155 Roselawn Road, 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

$1,139,900

4 Beds ⋅ 5 Baths ⋅ 982679 MLS

Welcome to Chester, NY, a resort-style luxury colonial set on a private 1.1-acre cul-de-sac lot in the Monroe-Woodbury area of Orange County. This custom residence delivers the space, craftsmanship, and lifestyle today's relocation and move-up buyers are searching for, with approximately 4,624 square feet, refined architectural detail, mountain views, and seamless indoor-outdoor living. From the bluestone entry and custom foyer to the arched windows, detailed millwork, and stone fireplace, every major room has been designed to make a statement. The chef's granite kitchen, expansive family room, and finished lower level with theater, gym, and additional recreation space create flexibility for entertaining, working from home, and everyday luxury. Outside, the backyard becomes the headline feature: saltwater in-ground pool, firepit, koi pond, extensive pavers, and a 3-season outdoor kitchen that gives this home true vacation-at-home appeal. For buyers looking for a luxury home in Chester NY, a Hudson Valley estate near NYC, or a Monroe-Woodbury area home with pool, privacy, and commuter convenience, This is the kind of property that sells both a residence and a lifestyle.

16 Lori Lane, Chester

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