Monroe-Woodbury Homes with Playground Amenities

Welcome to the enchanting Monroe-Woodbury School District, nestled in the heart of Orange County, New York. Renowned for its commitment to academic excellence and a well-rounded education, this district serves a vibrant community with a diverse population. With a strong focus on fostering creativity and critical thinking, Monroe-Woodbury boasts a range of educational programs that cater to students from kindergarten through high school. The district's dedicated teachers and staff work tirelessly to create a nurturing environment where every child can thrive, making it an ideal choice for families seeking quality education.

In addition to its stellar academic reputation, the Monroe-Woodbury area is perfect for families who value outdoor play and recreation. Many homes in the region come equipped with delightful playground amenities, ensuring that children have safe and engaging spaces to explore and play right at their doorstep. Imagine your little ones enjoying sunny afternoons on swings, slides, and climbing structures, fostering friendships and creating cherished memories.

Living in Monroe-Woodbury means you’re not just investing in a home; you’re embracing a community that prioritizes family and education. With nearby parks, recreational facilities, and a host of extracurricular activities, there’s no shortage of opportunities for children to grow, learn, and have fun.

Whether you’re looking for a cozy single-family home or a spacious property with ample outdoor space, Monroe-Woodbury offers a variety of options that cater to every family’s needs. Discover the charm of this exceptional school district and the joy of living in a community that truly values family and education. Your dream home awaits!

Newest Monroe-Woodbury Homes with Playground Amenities

$499,900

2 Beds ⋅ 3 Baths ⋅ 1008937 MLS

The home you have been waiting for! A perfect offering in the highly sought after Hidden Creek community, this spectacular, sun-filled Harriman Model END unit—clean as a whistle—is the epitome of upscale townhouse living. Impeccably maintained and beautifully appointed from top to bottom, this move-in-ready residence is perfectly positioned to capture tranquil views of mature trees, while offering the privacy and natural light only an end unit can provide. Spanning three levels of effortless living, this exceptional 2-bedroom, 2.5-bath home exudes warmth, sophistication, and a level of care rarely found. Every space has been thoughtfully enhanced with quality finishes, creating an inviting atmosphere that is both refined and functional. The beautifully renovated eat-in kitchen is designed to impress, featuring granite countertops, stainless steel appliances, a breakfast bar, abundant cabinetry, and sliders leading to a private deck overlooking a serene, bucolic landscape, an idyllic setting for morning coffee or evening sunsets. Walls of oversized picturesque windows bathe the home in natural light, highlighting gleaming hardwood floors and the open, airy floor plan. The spacious dining room flows seamlessly into the chic living room, creating an ideal setting for both elegant entertaining and everyday living. A beautifully updated powder room completes the main level. Upstairs, an expansive landing offers endless possibilities as a home office, reading nook, media area, or additional lounge space. Retreat to the impressive primary suite, where a grand bedroom is bathed in natural light from a wall of windows. A dream walk-in closet customized with an Elfa storage system provides exceptional storage, while the spa-inspired ensuite bath features oversized tile flooring, a soaking tub, and a double vanity. The spacious second bedroom features a large closet customized with an Elfa storage system and offers easy access to an updated hall bathroom. The finished lower level expands the home's versatility with additional living space, a laundry room, sliders leading to the backyard, and direct access to the attached two-car garage with additional storage. Premium upgrades throughout include: central vacuum, central air conditioning, temperature-controlled heating and cooling, recessed lighting, dimmer switches, natural gas, vinyl siding, a full attic, a newly installed front walkway, and an impressive list of additional improvements (see feature sheet). Hidden Creek is one of the area's most sought-after communities, distinguished by impeccably manicured grounds, and an unmatched lifestyle. Residents enjoy resort-caliber amenities including a sparkling inground pool, an elegant clubhouse with fireplace, gathering spaces, kitchen, fitness center, billiards room, basketball court and playground. Ideally located near the scenic Heritage Trail, Orange County’s beloved walking and biking path, minutes to Woodbury Common Premium Outlets, local wineries, LEGOLAND New York Resort, Resorts World Catskills, The Kartrite Resort & Indoor Waterpark, Museum Village of Old Smith's Clove, Sugar Loaf Arts & Crafts Village, Stewart International Airport, fine dining, shopping, and major commuter highways. Showcasing true pride of ownership, 20 Peter Turner Road offers timeless style and thoughtful updates throughout, all in an unbeatable location. A wonderful place to call home. We look forward to your visit.

20 Peter Turner Road, Monroe

$459,000

3 Beds ⋅ 3 Baths ⋅ 1018634 MLS

Welcome to this beautifully maintained end-unit townhome in the desirable Timber Ridge community. Featuring 3 bedrooms, 3 full baths and a finished basement. The gorgeous, updated stairs is the first thing you notice as you walk up to this great home and you will be WOWed from there! **Thoughtfully designed layout, eat-in kitchen with SS appliances and charming banquette seating, dedicated dining room, beautiful hardwood floors, custom doors, living room with vaulted ceilings and skylights as well as a cozy fireplace and a private patio**are just some features that impress as soon as you enter. Upstairs you will fall in love with the bright landing, extra deep closet, a bonus room as well as a very large bedroom with full bath. The finished basement offers lots of storage, an additional room that lends itself perfectly for a media room and a 2 car garage. Owning this home gives you access to the community pool and newly renovated playground as well as town amenities that include "The Rez" lake and the J.Burk town pool. Great commuter location near bus stops, major highways, Woodbury Commons, dining and Monroe Woodbury schools. ** Improvements: Roof replaced in March 2022; Water Heater Jan 2026; Kitchen Appliances Jan 2023**

15 Ash Court, Highland Mills

$360,000

3 Beds ⋅ 3 Baths ⋅ 1026625 MLS

New Pics! Welcome to easy, low-maintenance living in this beautifully maintained 3-bedroom, 2.5-bath condo townhouse offering 1,585 square feet of comfortable living space in a peaceful community. Wake up to tranquil views overlooking a picturesque lake and enjoy the perfect blend of privacy, convenience, and amenities. The bright and spacious layout features central air conditioning, generous living areas, and an ideal floor plan for both everyday living and entertaining. Outside, enjoy a quiet neighborhood with ample parking and exceptional community amenities, including a clubhouse, sparkling in-ground pool, and playground. With low monthly maintenance fees and low taxes, this home offers outstanding value. Conveniently located just minutes from Woodbury Common Premium Outlets, Greenwood Lake, restaurants, shopping, major highways, and everything the Hudson Valley has to offer, this is the perfect place to call home. Whether you're looking for your first home, downsizing, or seeking a weekend retreat, this move-in-ready townhouse checks all the boxes. Schedule your private showing today!

154 Eagleton Drive, Monroe

$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 dedicated dog park—all included through the homeowners association. The monthly HOA fee includes heating for added convenience and value. 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!

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

$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

$675,000

3 Beds ⋅ 3 Baths ⋅ 1011652 MLS

Welcome to the Prestigious Brigadoon Community in Highland Mills. Discover the perfect blend of style, space, and serenity in this contemporary gem, ideally situated at the end of a quiet cul-de-sac in the highly sought-after Brigadoon community. Located within the Monroe-Woodbury School District, this bright and beautiful home offers comfort and breathtaking mountain views throughout. The main level features a spacious primary suite with his-and-her closets and vaulted ceilings that flood the space with natural light. A large bonus room adds valuable flexibility, perfect as a home office, playroom, or media space. The airy, open floor plan includes a dramatic two-story living room with a modern flair and a cozy fireplace, creating a warm and inviting atmosphere. The open floor plan kitchen is outfitted with granite countertops and stainless-steel appliances, ideal for both everyday living and entertaining. Upstairs, generously sized guest bedrooms feature ample closet space, with a walk-up attic offering even more storage potential. There's also a walk-out basement—complete with windows and a door—ready to be finished to suit your needs. Enjoy outdoor living at its finest with a picture-perfect covered front porch, mature landscaping on your .34 acres, and a spacious back deck with sweeping mountain views. Additional highlights include a two-car garage, and the central air condenser was replaced just two years ago. Priced to sell quickly, this home is a rare opportunity in one of Highland Mills' most desirable neighborhoods. Besides having your own community Pool and playground, the Town of Woodbury offers a Lake/Res for summer camp, swimming, boating, fishing, a Gorgeous Town Pool Facility where you can enjoy Residents of Woodbury Only Summer Fun!!! Playground etc. Take a ride to see what Woodbury has to offer its residents.

7 Paisley Court, Highland Mills

$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

$819,000

5 Beds ⋅ 3 Baths ⋅ 1004118 MLS

On Zillow the virtual 3D tour you can find it by facts and features, 8 Allaway Crescent - 4,231 SQ FT + Full Unfinished Basement 4,231 SQ FT + Full Unfinished Basement | 5 Bedrooms Upstairs | Upstairs Laundry | Main Floor Bedroom + Full Bath | Mountain Views, Welcome to 8 Alloway Crescent. This 4,231 square foot home offers functional layout and impressive scale, plus a full unfinished basement ready for your vision. Main Level You enter through a big, wide foyer with hardwood flooring extending throughout the main level. Dining Room: To the right of the foyer is a big dining room with ample space for entertaining. Living Room: To the left of the foyer is a nice, big living room, well suited for formal seating or quiet conversation. Family Room: The beautiful big family room is open to the kitchen and open to the dinette area, accommodating large furniture arrangements and everyday living. Dinette: Adjacent to the kitchen, there is beautiful space for a dinette with room to put a table. This area has a walkout to the deck and access to the beautiful views. Kitchen: The big kitchen features a large center island, marble countertops, two sinks, abundant cabinetry, and stainless steel appliances. The layout flows directly into the family room and dinette for ease of daily use and hosting. Main Floor Bedroom & Full Bath: The main level includes a den or bedroom plus a full bathroom. This provides flexibility for guests, a home office, or multi-generational living. Garage & Views: A two-car garage is accessed from the main level. Beautiful scenery and views are visible from multiple rooms. Second Level Primary Suite: The master bedroom features a cathedral ceiling and beautiful mountain views. The en-suite bathroom includes a combined soaking tub with jetted jacuzzi, dual vanities, and a stall shower. A walk-in closet is included. The second bedroom is connected to the master with open doors. This layout works well as a baby room, office, or additional bedroom. The third bedroom is a nice size bedroom with closet space. The fourth bedroom is a nice size bedroom with closet space. Fifth Bedroom / Bonus Room: functions as a bonus room and provides additional flexibility for use as a bedroom, playroom, or media room. Laundry is located upstairs for convenience, near the bedrooms. Hall Bathroom: A full hall bathroom serves the additional bedrooms. Additional Levels Walk-Up Attic: A finished walk-up attic is accessed from the second floor and includes a window. The space is suitable for storage, studio, or playroom use. The home includes a full unfinished basement ready for future build-out. Key Specifications: 4,231 Sq Ft Above Grade | Full Unfinished Basement | 6 Total Bedrooms, 5 Upstairs | Upstairs Laundry | Main Floor Bedroom + Full Bath |2-Car Garage | Cathedral Ceiling in Primary | Walk-Up Attic with Window | Mountain Views

8 Alloway Crescent, Highland Mills

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