Monroe-Woodbury Homes with Pool

Monroe-Woodbury Homes with Pool

Welcome to the Monroe-Woodbury School District, a gem nestled in the heart of Orange County, NY. This vibrant community is not only known for its picturesque landscapes and charming neighborhoods but also for its commitment to providing an exceptional educational experience. The district is home to highly-rated schools that prioritize academic excellence, innovative teaching methods, and a strong focus on student well-being. With a diverse range of programs, from advanced placement courses to arts and athletics, Monroe-Woodbury cultivates an environment where every student can thrive and reach their full potential.

As you explore the real estate options in this desirable area, you’ll find an array of stunning homes, many of which boast inviting pools that make for the perfect summer retreat. Imagine hosting family gatherings or weekend barbecues in your own backyard oasis, where the kids can splash around while you relax poolside. These homes not only offer luxurious amenities but also provide a sense of community, with friendly neighbors and nearby parks that encourage outdoor activities.

Living in Monroe-Woodbury means you can enjoy the best of both worlds—access to top-notch education and the comfort of a serene suburban lifestyle. With its blend of quality schools, beautiful homes with pools, and a welcoming community spirit, it’s no wonder that Monroe-Woodbury is a sought-after destination for families looking to settle down in Orange County. Come discover your dream home in this enchanting area, where education and leisure come together seamlessly!

Newest Monroe-Woodbury Homes with Pool

$845,000
3 Beds ⋅ 3 Baths ⋅ 1030419 MLS
Walls of Glass. Morning Light. Forest. At the end of a quiet cul-de-sac in the Town of Tuxedo, New York, this thoughtfully updated mid-century contemporary borders Sterling Forest State Park on two sides, creating an extraordinary sense of privacy and connection to nature. Expansive walls of glass fill the home with natural light, framing mountain views and creating interiors that change beautifully with the seasons. The main living spaces are open, warm, and inviting, and anchored by vaulted ceilings, a wood-burning fireplace, and hardwood floors throughout the main level. The kitchen has been thoughtfully updated with custom cherry cabinetry, granite countertops, brand-new appliances installed within the past year, and offers exceptional storage for kitchenware and pantry items. Just beyond, an oversized deck extends the living space outdoors for dining, entertaining, or simply enjoying the peaceful setting. The primary suite features a beautifully renovated spa-inspired bath with radiant heated floors. Two additional bedrooms are finished with custom Hunter Douglas shutters, while major mechanical improvements, including new heating and air conditioning systems and a water heater installed in 2024, provide peace of mind for many years to come. The lower level adds exceptional flexibility to the home. A spacious mudroom with laundry is located directly off the driveway, offering abundant storage for four-season gear and everyday essentials. A full bathroom and three additional rooms provide endless possibilities for home offices, guest accommodations, a fitness studio, media room, or additional living space. The home is about 2,939 sq ft with all spaces factored in. Outside, the lifestyle is every bit as compelling as the home itself. A low-maintenance saltwater pool is surrounded by perennial gardens, ornamental trees, and a pergola that offers welcome shade on warm summer afternoons. Landscape lighting transforms the grounds after sunset, while an outdoor shower, oversized storage shed with covered firewood storage, and a whole-house generator add comfort and practicality. Meandering pathways lead to quiet corners tucked within the property, creating natural spaces for a fire pit, play, or simply enjoying the tranquility of the setting. Open lawn, mature landscaping, and direct access to thousands of acres of Sterling Forest State Park make this property feel worlds away, while remaining just minutes from NJ Transit rail service, commuter bus service to New York City, Valley Rock Inn, local coffee shops, restaurants, Mt. Peter Ski Area and everyday conveniences. Located within the Monroe-Woodbury School District in New York's Lower Hudson Valley, this home offers a beautiful balance of contemporary design, thoughtful updates, and an outdoor lifestyle that is increasingly difficult to find. A place where architecture, landscape, and everyday living exist in remarkable harmony.

68 Spice Bush Lane, Tuxedo Park
$879,999
5 Beds ⋅ 4 Baths ⋅ 1030228 MLS
INCREDIBLE VALUE IN THE GREENS OF WOODBURY! This is your opportunity to own a spacious Colonial in one of the Hudson Valley's most sought-after neighborhoods at an exceptional new price. Offering over 3,400 square feet of living space, this 5-bedroom, 4-full-bath home is ideal for buyers looking to build equity while creating their dream home. Situated in the highly desirable town of Woodbury, this home features a dramatic two-story foyer, soaring ceilings, hardwood floors, skylights, and an open floor plan designed for comfortable everyday living and entertaining. The eat-in kitchen offers granite countertops, stainless steel appliances, abundant cabinetry, and overlooks the inviting family room with a cozy wood-burning fireplace. The spacious primary suite includes a walk-in closet and private en-suite bath, while four additional bedrooms provide flexibility for guests, home offices, multigenerational living, or room to grow and adapt over time. The real showstopper is the backyard, featuring an in-ground pool, expansive paver patio, and a private full-size basketball court—an ideal setting for entertaining, recreation, and making lasting memories. A full walkout basement offers tremendous potential for additional finished living space, a recreation room, home gym, media room, or possible extended living area with the proper approvals. This home has been priced to reflect the cosmetic updates and TLC a new owner may wish to make, presenting an outstanding opportunity to personalize a home in an established neighborhood where values continue to remain strong. Conveniently located just minutes from Woodbury Common Premium Outlets, parks, hiking trails, golf courses, restaurants, shopping, and major commuter routes including I-87, Route 17, and public transportation to New York City. Residents also enjoy access to Woodbury Parks & Recreation, offering year-round activities and amenities. If you've been searching for space, location, and unlimited potential, this is the opportunity you've been waiting for. Bring your vision and make this exceptional property your forever home. Schedule your private showing today!

43 Greenwich Avenue, Central Valley
$999,998
5 Beds ⋅ 4 Baths ⋅ 1029095 MLS
Welcome to 190 Ridge Road in the heart of Highland Mills! Nestled on a beautiful 1-acre lot in the highly sought-after Monroe-Woodbury School District, this spacious 4-bedroom, 3.5-bath split-level home offers over 2,500 square feet of comfortable living space designed for both everyday living and entertaining. Step inside to discover an inviting open floor plan featuring cathedral and high ceilings, a stunning kitchen with a center island, granite countertops, stainless steel appliances, pantry, and eat-in dining area. The formal dining room and bright living spaces provide the perfect setting for gatherings with family and friends. The primary suite offers a private retreat with a walk-in closet and en-suite bath featuring a double vanity and soaking tub. A versatile office can easily serve as a fifth bedroom, guest room, or sitting room. The entry level features a formal living room with a masonry fireplace and pellet stove, ideal for relaxing on cool evenings. There is a huge family room on the lower level - great for entertaining or hanging with the family and friends! Additional features include central air, recessed lighting, ceiling fans, skylights, abundant storage, and a spacious laundry room. Enjoy the community town pool located in Central Valley or the "Rez" located within walking distance. Outside, your backyard oasis awaits! Spend summers enjoying the in-ground pool, while the expansive yard provides plenty of room for entertaining, gardening, or simply enjoying the peaceful surroundings. Watch the fireworks from your deck when the "Rez" Celebrates 4th of July! An oversized garage and private driveway offer ample parking and storage. Conveniently located just minutes from major highways, shopping, parks, and schools, this home combines privacy with everyday convenience. Don’t miss the opportunity to make this exceptional Highland Mills property your forever home!

190 Ridge Road, Highland Mills
$925,000
4 Beds ⋅ 3 Baths ⋅ 1023811 MLS
Luxury, comfort, and exceptional craftsmanship define this stunning four-bedroom Center Hall Colonial. Thoughtfully designed with superior craftsmanship and premium finishes throughout, this impressive residence offers the perfect blend of sophistication, comfort, and functionality for the discerning buyer. At the heart of the home is a spectacular custom chef's kitchen featuring Travertine marble flooring, handcrafted cabinetry, a center island, Wolf built-in oven with warming drawer, Wolf microwave/convection oven, Sub-Zero refrigerator, Thermador induction cooktop, and Miele dishwasher—an extraordinary space designed for everyday living and effortless entertaining. The sun-filled living and dining rooms offer an elegant setting for both formal gatherings and everyday enjoyment. The inviting great room features soaring cathedral ceilings, a custom cherry built-in entertainment wall with surround sound, and seamless access to the backyard, where the outdoor amenities are second to none. Step outside to your own private backyard oasis featuring a stunning Cypress pergola, elegant stone patio, heated saltwater in-ground pool with exposed aggregate decking, and a separate hot tub. Weather entertaining guests or enjoying a peaceful evening under the stars, this exceptional outdoor living space is designed for year-round enjoyment. Additional highlights include a distinctive stucco front exterior with a covered front porch, an oversized three-car garage, two large storage sheds, and generously sized secondary bedrooms, each with dedicated study or play areas. The finished basement provides substantial additional living and entertaining space and is not included in the home's reported square footage, adding exceptional value and versatility. Also close to West Point, Woodbury Commons, Wineries, Hiking Trails, NYC transportation and with Woodbury Recreation access. From its exceptional craftsmanship to its resort-style outdoor amenities, every detail of this remarkable home reflects quality, elegance, and pride of ownership. A rare opportunity to own a residence of this caliber—one you won't want to miss.

10 Sutherland Drive, Highland Mills
$575,000
3 Beds ⋅ 3 Baths ⋅ 1018371 MLS
Welcome to this beautifully maintained raised ranch, perfectly situated on a desirable corner lot in Chester. This inviting 3-bedroom, 2 full and 1 half bath home blends comfort, style, and modern convenience in a location you'll love. Filled with natural light, the home features spacious living areas and a well-appointed kitchen with stainless steel appliances. The finished basement offers flexible space for a family room, home office, gym, or guest retreat. Thoughtful upgrades, including a Nest thermostat, Ring security camera with window sensors, and a reverse osmosis water filtration system, enhance both comfort and convenience. In addition to the home's primary boiler heating system, the central HVAC system provides air conditioning and electric auxiliary heat, offering added comfort and flexibility throughout the seasons. Step outside to your own private backyard oasis featuring a spacious deck, above-ground pool, and newly installed white vinyl privacy fence—perfect for relaxing or entertaining. Conveniently located just 12 minutes from Woodbury Common Premium Outlets with easy access to major highways, this home offers the perfect blend of peaceful suburban living and everyday convenience. Don't miss the opportunity to make it yours!

11 Chandler Drive, Chester
$800,000
4 Beds ⋅ 4 Baths ⋅ 1020165 MLS
Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgettable place to call home. Inside, the heart of the home is anchored by a stunning double sided fireplace that effortlessly connects the main living areas, creating warmth, character, and an inviting atmosphere for both everyday living and entertaining. Sunlight pours into the beautiful sunroom, offering the perfect place to enjoy your morning coffee, unwind with a good book, or simply take in the tranquil views of the property throughout every season. Step outside and discover the true highlight of this remarkable property. Designed with entertaining in mind, the backyard is a private oasis featuring a sparkling inground pool, beautifully integrated outdoor living spaces, a custom built fire pit, and built in seating that invites family and friends to gather long after the sun goes down. Whether you're hosting summer pool parties, enjoying crisp fall evenings by the fire, or simply relaxing in your own backyard retreat, this outdoor space delivers an exceptional lifestyle year round. Set on over three private acres, the property offers the perfect balance of open space and privacy. There is plenty of room to explore, play, garden, or simply enjoy the serenity of nature, all while being just minutes from the conveniences of the Hudson Valley. Offering 4 bedrooms, inviting living spaces, and an outdoor setting that feels like your own private resort, this is more than just a home. It is a place where memories are made, weekends are enjoyed, and every season brings something special.

985 Craigville Road, Chester
$569,000
3 Beds ⋅ 2 Baths ⋅ 1018026 MLS
Pride of ownership is evident throughout this beautifully updated 3-4 bedroom Colonial, where timeless character blends seamlessly with modern comfort. Original architectural details include elegant 9 ' coffered ceilings in the living room, and large windows create a bright and inviting atmosphere. The home features a spacious living room with an electric fireplace, a charming covered front porch and a backyard with a large, updated patio that is perfect for relaxing or entertaining. Recently updated bathrooms; w/u attic and basement allow for ample storage; new heating system, whole house water filtration system, Radon mitigation system, solar panels are owned for substantial savings on electric cost. Conveniently located just minutes from Interstate 87 and approximately 55 minutes to New York City. This property offers accessibility and a desired lifestyle. Residents enjoy access to local amenities, including the REZ, and the town pool. A short drive to Woodbury Commons Premium Outlets, restaurants, Bear Mountain, West Point.....in short, all the fantastic destinations the Hudson Valley has to offer.

20 Shuit Place, Central Valley
$599,000
4 Beds ⋅ 3 Baths ⋅ 1016143 MLS
Welcome to this classic 4-bedroom, 2.5-bath Colonial nestled in the heart of the Village of Monroe. Offering a fantastic layout, generous living spaces, and endless potential, this home is ready for its next owners to make it their own. A welcoming foyer greets you upon entry and leads to a spacious living room, currently being utilized as a first-floor bedroom, offering flexibility to fit your needs. There is also a formal dining room, perfect for holiday gatherings and entertaining guests. The bright, spacious kitchen features granite countertops, abundant cabinetry, and a separate breakfast area overlooking the beautifully landscaped backyard. There is also a cozy family room/den with a pellet stove that helps cut down heating costs in the winter. Off the family room you'll find a screened-in porch and adjoining deck—an ideal setting for grilling, outdoor dining, or simply relaxing while overlooking the backyard and heated in-ground pool. A convenient first-floor powder room and laundry room add to the home’s everyday functionality and round out the first floor. Upstairs, you’ll find three generously sized secondary bedrooms, a full hallway bath, and a spacious primary suite complete with its own private bath. Ample closet space can be found throughout the home. The walkout basement offers outstanding potential to create additional finished living space, a home office, gym, or recreation room. The pull down attic and an attached two-car garage provide added convenience and storage. Situated on a sidewalk-lined street with mature landscaping, this home is conveniently located near shops, restaurants, schools, parks, and major highways, making commuting and everyday errands a breeze. Lovingly maintained by its current owners, this home is ready for its next chapter. With a wonderful floor plan, spacious indoor and outdoor living areas, and endless potential to add your own personal touches, this is an opportunity you won’t want to miss. Schedule a showing today. Monroe Woodbury Schools. Connected perfectly for commuters with bus and train options close by.

33 Winchester Drive, Monroe
$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
$899,000
4 Beds ⋅ 3 Baths ⋅ 996875 MLS
Beautifully maintained and thoughtfully updated, this exceptional home is set on professionally landscaped grounds with outstanding curb appeal and a resort-style backyard designed for both relaxation and entertaining. The inviting interior features a grand entry foyer, a stunning chef's kitchen with custom cabinetry, granite countertops, and stainless steel appliances, along with spacious living and dining areas ideal for everyday living and gatherings alike. Generously sized bedrooms and versatile living spaces provide comfort and flexibility throughout. Step outside to your own private retreat, complete with a sparkling in-ground pool, cascading waterfall, expansive deck, hot tub, and beautifully manicured grounds surrounded by mature trees. Meticulously cared for inside and out, this move-in-ready property offers the perfect balance of elegance, comfort, privacy, and outdoor living. A truly special home that must be seen to be fully appreciated.

11 Country Hollow, Highland Mills
$649,000
5 Beds ⋅ 3 Baths ⋅ 1014145 MLS
Large & Spacious expanded 5-bedroom, 3 bath raised ranch sits on a private level acre in Monroe, offering exceptional potential for its next owner. The home features a generous floorplan with 4 bedrooms on the main level, a bright kitchen, formal livingroom, central air, fireplace, hardwood-floors in the living room, roof (2019) Furnace (2018) and newer Hot Water Heater (2021). The primary ensuite includes a standup shower, jacuzzi tub, walkin closet and striking black marble fireplace. A fifth bedroom on the lower level with a full bath could provide a private area for guests visiting or in-law suite possibilities. Step outside to a large deck off the kitchen, overlooking a 20 x 40 in-ground pool surrounded by a peaceful, wooded backdrop, perfect for summer relaxation and entertaining. An added lower level with stairs off the main floor adds even more versatility with a spacious recreation room and wet bar, ideal for gatherings or extended living space. Conveniently located near shopping, major commuter routes, local amenities, lakes, hiking trails, and Monroe Woodbury Schools, this home offers space, privacy and a great potential for its next owner. While the home offers great space and desirable features, updating and repairs are needed giving buyers the opportunity to customize and add value over time. With vision and improvements, this property can truly shine! A must see!

67 Carol Drive, Monroe
$699,000
3 Beds ⋅ 2 Baths ⋅ 952720 MLS
Welcome to 205 High Street in the heart of Monroe, where timeless craftsmanship meets modern comfort in this truly one-of-a-kind Colonial located within the highly sought-after Monroe-Woodbury School District. Situated on a beautiful corner lot, this exceptional property offers a rare opportunity to purchase separately or together with the neighboring custom-built home at 23 Sweezy Place, originally designed to complement the home while providing additional living space and an impressive four-car garage. From the moment you arrive, the slate roof, covered rocking-chair front porch, side porch, and stunning woodwork and quarter-sawn tiger oak flooring set the tone for the home's warm, old-world charm. Inside, the custom gourmet kitchen is a chef's dream, featuring handcrafted pantry cabinetry, wood beams, a farmhouse sink, oversized island with storage, subway tile backsplash, wide plank aged flooring, spice racks, refuse drawer, custom-paneled refrigerator, breakfast nook, and a Viking dual-fuel range with four burners, grill, and double ovens. Entertain with ease in the formal dining room, inviting living room with a slate wood-burning fireplace, and the spectacular sunroom/mudroom showcasing custom stained glass and built-in cabinetry. The luxurious primary suite offers his-and-her closets, a private sitting sunroom filled with natural light. The bathroom has a spa-inspired marble bath complete with a soaking tub, oversized shower with five shower heads, porcelain vanity, and a custom six-foot medicine cabinet. Two additional bedrooms and beautiful oak doors throughout complete the second floor. Step outside to your own private resort featuring a heated gunite pool with hot tub, paver patio, outdoor kitchen with a Viking natural gas BBQ with 2 burners, outdoor shower with tankless water heater, fully fenced yard, and multiple patios spaces offer space for everyone. A wood-burning fireplace creates the perfect setting for relaxing poolside on cool evenings. The full basement provides endless possibilities, recreation space, or storage. Walk to the Village, located just moments from Mill Pond, charming village shops, restaurants, farmers markets, wineries, parks, and recreational amenities, this commuter-friendly location is approximately 50 miles from NYC and offers easy access to Routes 17, 84, and 87, Metro-North, NJ Transit, bus service, Stewart International Airport, and West Point. A truly rare offering combining character, luxury, and versatility—schedule your private showing today and don't forget to inquire about the neighboring property at 23 Sweezy Place.

205 High Street, Monroe
Start Your Search

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.