Monroe-Woodbury Homes with Contemporary Style

Welcome to the vibrant community of Monroe-Woodbury, nestled in the picturesque Orange County of New York. This charming area is renowned for its exceptional school district, which consistently ranks among the top in the state. The Monroe-Woodbury Central School District prides itself on providing a well-rounded education that fosters academic excellence, creativity, and critical thinking. With a variety of educational programs and extracurricular activities, students are encouraged to explore their interests and develop their talents in a supportive environment. Families are drawn to this district not only for its strong academic performance but also for its commitment to creating a safe and nurturing atmosphere for all students.

As you explore the real estate options in Monroe-Woodbury, you’ll discover an array of contemporary-style homes that perfectly blend modern aesthetics with functional living. These homes are designed with open floor plans, large windows that flood spaces with natural light, and sleek finishes that appeal to today’s discerning buyers. Whether you’re looking for a cozy retreat or a spacious family home, the contemporary properties in this area offer the perfect backdrop for your lifestyle.

Living in Monroe-Woodbury means enjoying the best of both worlds: a serene suburban environment with easy access to urban amenities. With beautiful parks, shopping centers, and recreational facilities nearby, residents can relish a balanced lifestyle that prioritizes both leisure and community engagement. Discover your dream home in Monroe-Woodbury, where contemporary living meets an exceptional education. Come experience the charm and convenience of this remarkable area!

Newest Monroe-Woodbury Homes with Contemporary Style

$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

$759,900

4 Beds ⋅ 4 Baths ⋅ 1031701 MLS

Looking for a modern, move-in ready home that perfectly blends space, storage, and style? Welcome home! This exceptional 4-bedroom, 4 full-bath residence offers timeless elegance, thoughtful design, and incredible value. Designed for both everyday living and effortless entertaining, the home features two spacious primary suites, gleaming hardwood floors throughout, soaring vaulted ceilings, elegant light fixtures, and a stunning fireplace that creates a warm, inviting atmosphere. The beautifully appointed kitchen showcases quartz countertops, abundant cabinetry, and the perfect layout for gathering with family and friends. The finished walk-up attic provides a versatile bonus space complete with a full bathroom—ideal as a recreation room, home office, guest suite, or media room. The dining room is filled with warmth and character, featuring a fireplace and sliding glass doors that seamlessly connect the indoor living space to the outdoors. Step onto the generously sized deck, perfect for hosting large gatherings or simply relaxing while overlooking the patio and expansive level backyard. With plenty of room to add a pool, play area, garden, or outdoor kitchen, the possibilities are endless. Every detail of this home has been thoughtfully designed to maximize comfort, functionality, and the enjoyment of both indoor and outdoor living. Whether you're creating everyday memories or celebrating life's biggest moments, this remarkable home provides the perfect setting for years to come.

26 Seals Drive, Monroe

$650,000

3 Beds ⋅ 4 Baths ⋅ 1027353 MLS

Welcome to a contemporary retreat where refined design, exceptional craftsmanship, and a seamless connection to nature come together in one of Chester’s most desirable settings. Thoughtfully designed for both everyday living and effortless entertaining, this light-filled residence offers three bedrooms, two full bathrooms, and two half baths with an open, flowing floor plan that balances sophistication with comfort. The main level is defined by soaring ceilings, expansive windows, and an abundance of natural light that fills every corner of the home. The dramatic living room serves as the heart of the residence, centered around a wood-burning fireplace and overlooking a beautifully landscaped backyard complete with a custom-built pond and tranquil gardens that create a truly peaceful backdrop. The custom-designed white kitchen is a true showpiece, crafted for those who love to entertain. A large center island with an integrated cooktop allows the chef to remain part of every conversation, while generous workspace, custom cabinetry, and views of the surrounding landscape make the space as functional as it is beautiful. Sliding doors extend the living space to a private patio, creating a natural indoor-outdoor flow for dining and gatherings. Upstairs, the spacious primary suite and additional bedrooms are thoughtfully appointed with custom-built closet systems that maximize both style and organization. Three generously sized bedrooms and two beautifully finished full bathrooms provide comfortable accommodations designed for modern living. The finished lower level offers exceptional flexibility, featuring a spacious recreation or living area, a convenient half bath, and a dedicated storage room—ideal for a media room, home office, gym, guest retreat, or extended living space. Perfectly positioned just minutes from Walton Lake, Goosepond Mountain State Park, and the world-class shopping and dining of Woodbury Common Premium Outlets, this home offers the best of Hudson Valley living with convenient access to New York City in approximately 90 minutes. Combining contemporary architecture, designer finishes, and an idyllic natural setting, this exceptional residence delivers a lifestyle defined by comfort, elegance, and effortless luxury.

29 Murray Drive, Chester

$620,000

3 Beds ⋅ 2 Baths ⋅ 1026296 MLS

Welcome to this Frank Lloyd Wright-inspired contemporary ranch, where timeless architecture, natural beauty, and modern updates come together in perfect harmony. Bordering acres of protected parkland, this one-of-a-kind home offers exceptional privacy and a peaceful retreat surrounded by nature. Listen to birdsong, unwind beside the tranquil koi pond and cascading water features, or simply enjoy the serenity from the expansive wraparound cedar deck. A dramatic bridge entrance leads to this custom-designed 3-bedroom, 2 full bath residence, showcasing striking redwood siding and distinctive architectural details. Inside, a bright, open floor plan is filled with natural light through walls of glass that blur the line between indoors and out. The main living area features stunning walnut hardwood floors, 9-foot ceilings, and a dramatic wood-burning fireplace that anchors the living and dining spaces. The chef's kitchen is designed for both everyday living and entertaining, featuring granite countertops, custom wood cabinetry, stainless steel appliances, generous workspace, and an abundance of windows overlooking the picturesque landscape. Recent improvements provide added value and peace of mind, including a brand-new roof, new soffits with built-in lighting, new fascia boards and gutters, a beautifully updated bathroom with new countertops, tile flooring, and shower tile, as well as a new water heater. The finished lower level offers a spacious family room or den with a second wood-burning fireplace and sliding glass doors leading to a massive outdoor deck, creating the perfect space for gatherings or quiet relaxation. A dedicated workshop and expansive unfinished storage area provide endless possibilities for hobbies, projects, and organization. Conveniently located near shopping, parks, community tennis courts, public transportation, and major commuter routes with easy access to New York City, this exceptional home is a rare opportunity to own a truly distinctive property where architecture and nature exist in perfect balance.

66 High Hill Road, Tuxedo Park

$1,149,000

5 Beds ⋅ 3 Baths ⋅ 1020835 MLS

MOTIVATED BUILDER SAYS SELL! NEW CONSTRUCTION WITH YEAR ROUND LAKE VIEWS!! HOUSE AND PROPERTY OF THIS QUALITY, DRAMA AND CUSTOM FINISHES OVERLOOKING LOOKING A LAKE IN THIS AREA IS A RARE FIND! Just 60 minutes from New York City and very close to the northern Tuxedo border, this custom Colonial offers an exceptional blend of luxury, privacy, and natural beauty. The home is set on a peaceful property with YEAR ROUND VIEWS of Mombasha Lake and CLOSELY bordering protected state land—ensuring natural surroundings, and relaxing landscape. Designed for elevated living and entertaining, this residence features 4/5 bedrooms, 3 full baths, and a rare SIX-CAR GARAGE with dramatic 18-foot ceiling and a gas line installed--ideal for car collectors, creativity, or luxury storage. Walls with OVERSIZED WINDOWS bring the outdoors in, bathing the home in natural light and stunning lake views. The extensive covered porch offers the addition of more entertaining space or quiet enjoyment. The MAIN LEVEL offers 10-FOOT CEILINGS and an artfully designed GREAT ROOOM has a soaring 20-FOOT CEILING, massive STONE WOOD-BURNING FIREPLACE and seamless indoor-outdoor flow. Anchoring the home is a CUSTOM WHITE OAK AND SATIN IRON STAIRCASE SPANNING FOUR LEVELS, a dramatic architectural statement that rises gracefully through the space and sets the tone for the home’s refined design and craftsmanship. The chef-caliber kitchen is a statement piece, featuring a 5x10-FOOT QUARTZ ISLAND, custom cabinetry, 48-INCH PROFESSIONAL EIGHT BURNER DOUBLE-OVEN RANGE, STAINLESS STEEL APPLIANCES, and a built-in wine cooler—perfect for both intimate dinners and large-scale entertaining. The formal dining room, elegant living room, full bath, and a flexible den or private office (optional fifth bedroom) offer versatility for guests, work, or multigenerational living. A full bath completes the main level. UPSTAIRS 9-FOOT CEILINGS frame four spacious bedrooms, and additional full bath. A BONUS ROOM EXCEEDING 1,300 SQUARE FEET can be finished presenting endless possibilities—media lounge, fitness studio, guest suite, or work-from-home refuge. The primary suite is a true haven, offering a luxurious bath with RADIANT HEATED FLOORS, OVERSIZED SHOWER WITH BODY JETS AND CEILING MOUNTED RAIN SHOWER WITH INTEGRATED BLUETOOTH SPEAKERS AND LED LIGHTS, therapeutic whirlpool tub, heated towel bar, a SEPARATE STEAM/DRY SAUNA, and sliding doors that open to a JULIET BALCONY. There is a fourth level with an abundance of storage and a TREMENDOUS ROOF TOP TERRACE. Here, lake and mountain views stretch endlessly—an extraordinary setting for sunrise reflections or sunset cocktails. The EXPANSIVE BASEMENT ADDS ANOTHER 2,000 SQUARE FEET, with endless possibilities for a creative retreat, home theater, wellness studio, or space where imagination can run free. More than a home, this is a place to create lasting memories and moments of joy—a sanctuary where every day feels like a retreat. Located within the Monroe-Woodbury School District, this home offers the rare opportunity to experience resort-level living, complete relaxation, and architectural distinction—all within easy reach of New York City. LARGE DECK OR PAVER PATIO WILL REPLACE THE TEMPORARY STEPS TO BACKYARD.

133 W Mombasha Road, Monroe

$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

$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

$1,200,000

4 Beds ⋅ 3 Baths ⋅ 1010784 MLS

This stunning 4 bedroom, 3 bathroom home with a beautifully updated kitchen is the perfect place to call home. With plenty of space to entertain and relax, you'll love the open layout and modern amenities that this home has to offer. Whether you're enjoying a meal in the spacious kitchen or unwinding in the cozy living room, you'll feel right at home in this charming and inviting space.

63 Whitetail Run, Chester

$1,200,000

5 Beds ⋅ 4 Baths ⋅ 996131 MLS

Welcome to this newly built (November 2025) lakefront residence offering 5 bedrooms and 3.5 bathrooms on a 0.98-acre property. This home features an open-concept layout with abundant natural light through Low-E Argon gas windows and doors. The first floor is finished with imported European porcelain tile flooring and radiant in-floor heating. Interior features include a custom red oak staircase with integrated LED lighting, HVAC system with radiators, Navien water heater, invisible Sonos ceiling speakers, and TV/telephone wiring in each bedroom. The kitchen includes custom cabinetry, quartz countertops, a commercial-style range, separate cooktop, pot filler, and stainless steel appliances. Smart-home and security features include a Face ID intercom system and security camera system. Laundry connections are installed and ready for use; washer and dryer are not included in the sale. This property is also available for lease at $6,500 per month. Located at 548 Lakes Road, Monroe, NY, this property offers access to major commuter routes including Route 17M, NY-17/I-86, the New York State Thruway (I-87), and Route 6, providing connectivity throughout the Hudson Valley and to surrounding areas. Monroe is located approximately 50–60 miles from New York City, with access to shopping, parks, recreation, and regional transportation options. Exterior features include two 15’ x 45’ decks, a private dock, new well, and town sewer connection. The property includes approved zoning board approvals and building permits for a proposed detached 24’ x 30’ garage. Property size and zoning may provide additional possibilities; buyers should conduct their own due diligence and consult with architects, engineers, and municipal authorities regarding future use, subdivision, or expansion potential. Garage approval documents, permits, and floor plans are available upon request.

548 Lakes Road, Monroe

$894,000

3 Beds ⋅ 4 Baths ⋅ 000137 MLS

220 Oxford Road is a Truly Impressive Property! Offering over 3,500 sq ft of beautifully maintained living space, this home features 3 bedrooms plus an additional upper-level room, 3 full baths, and 1 half bath. Spacious living room, stunning family room, and a practical, well-designed kitchen. The home showcases elegant finishes throughout along with brand new flooring that adds a fresh modern touch. Full basement provides excellent storage space. Additional features include Central AC, original Andersen custom windows, and an attached 2-car garage. Step outside to a massive deck, spacious shed, and gorgeous landscaping set on a nice-sized lot. Conveniently located close to all amenities, this property offers privacy, space, and everything you could want in a home and more!

220 Oxford Road, Chester

$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

$599,000

4 Beds ⋅ 3 Baths ⋅ 989071 MLS

Beautifully maintained and thoughtfully updated Colonial set in a prime location close to shopping, restaurants, parks, and major commuter routes. This spacious home offers bright sun-filled living areas, gleaming hardwood floors, and an inviting open layout perfect for everyday living and entertaining. The expansive kitchen features abundant cabinetry, generous counter space, and a seamless flow into the dining and living areas. Multiple oversized gathering spaces provide flexibility for entertaining, relaxing, or working from home. The stunning fireplace living room adds warmth and character, while the large upstairs landing offers additional bonus space ideal for a reading area, office, or lounge. The spacious bedrooms include a beautifully sized primary suite with soaring ceilings and ample closet space. Well-maintained bathrooms, large windows, and natural sunlight throughout create a warm and welcoming feel in every room. Outside, enjoy exceptional curb appeal with mature landscaping, manicured grounds, and a private backyard setting. The property is surrounded by lush greenery while still being conveniently located close to shopping, dining, schools, and everyday conveniences. A rare combination of space, location, and charm — this is a home you do not want to miss. Virtually staged for your imagination.

4 Mack Place, Monroe

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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.