Monroe-Woodbury Homes with Pool Amenities

Welcome to the Monroe-Woodbury School District, a vibrant and nurturing educational community nestled in the heart of Orange County, New York. Renowned for its commitment to academic excellence, Monroe-Woodbury serves students from pre-kindergarten through grade 12, providing a comprehensive curriculum that fosters both intellectual growth and personal development. With a dedicated team of educators and a plethora of extracurricular activities, students are encouraged to explore their interests and talents, ensuring a well-rounded educational experience.

Families residing in this picturesque area enjoy the benefits of a supportive school district, which is complemented by a welcoming community atmosphere. The Monroe-Woodbury School District prides itself on its strong parental involvement and community partnerships, making it a desirable location for families seeking a nurturing environment for their children.

In addition to exceptional educational opportunities, the Monroe-Woodbury area offers an array of stunning homes, many of which feature luxurious pool amenities. Imagine coming home to a serene oasis where you can unwind and entertain friends and family by your very own pool. These homes not only provide a private retreat but also enhance the overall lifestyle of residents, making summer days a delight and outdoor gatherings a breeze.

Whether you are drawn to the exceptional schools, the charming neighborhood, or the allure of a home with a pool, Monroe-Woodbury is a perfect choice for families looking to settle in a thriving community. Experience the beauty and convenience of life in this remarkable area, where education and leisure come together seamlessly.

Newest Monroe-Woodbury Homes with Pool 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

$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

$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

$699,000

4 Beds ⋅ 4 Baths ⋅ 1012887 MLS

Welcome to an unparalleled lifestyle of luxury and leisure in Mansion Ridge, Orange County’s premier gated community. Nestled alongside a pristine Jack Nicklaus Signature Golf Course, this spectacular, completely renovated (2021) three-level townhouse offers the perfect blend of sophisticated design and resort-style amenities. Step inside to an airy, light-filled main level with hardwood floors and a cozy gas fireplace. The heart of the home is the chef-inspired gourmet kitchen, featuring: quartz countertops including an extra-large center island, a dedicated coffee nook and a chic wet bar for hosting. Seamless flow to the outdoor deck, complete with a retractable awning—ideal for evening cocktails overlooking the manicured fairways. Head to the upper level, where eco-elegant bamboo flooring guides you to the expansive primary suite. Wake up to sweeping, serene golf course views and indulge in a spa-like ensuite bathroom that rivals the world’s finest resorts. It boasts: cozy radiant heated floors, an extra-large shower equipped with dual regular showerheads plus a rainfall head and a deep Japanese soaking tub for ultimate relaxation. The fully finished walk-out lower level is a dedicated sanctuary for health and entertainment. It features a spacious gathering room, a private fourth bedroom, and your very own wellness center equipped with an Endless Pool and a Clearlight Infrared Sauna. No detail has been overlooked, right down to the garage, which features a Level 2 EV charger and stylish, durable perforated utility tile flooring. Situated in one of the region's most highly desirable enclaves, you are just minutes from the world-class shopping at Woodbury Common Premium Outlets. Best of all, this tranquil retreat is located just 50 miles from midtown Manhattan, offering an effortless commute to NYC via nearby train, bus, or highway. Experience the pinnacle of sophisticated suburban living. A definite must see!

38 Pinehurst Circle, Monroe

$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

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