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

$679,900

3 Beds ⋅ 3 Baths ⋅ 1050106 MLS

Come fall in love with this stunning 3-bedroom plus office Contemporary Colonial, beautifully set on just under an acre in one of Monroe’s most sought-after neighborhoods. Originally a ranch, the home was thoughtfully expanded approximately 20 years ago and transformed into a spacious, light-filled home with dramatic architectural details and a wonderful open layout. The heart of the home is the impressive two-story great room with soaring vaulted ceilings, a dramatic wall of windows, a fireplace and plenty of recessed lighting. The kitchen offers abundant cabinetry, granite countertops, stainless steel appliances and a glass mosaic tile backsplash, and opens beautifully to the main living spaces. Two bedrooms are conveniently located on the main level, offering flexibility for family, guests or one-level living. Upstairs, the primary suite feels like a true retreat. Double doors lead into the spacious bedroom, complete with gorgeous mountain views and a large walk-in closet. The oversized primary bath features a Jacuzzi tub, double sinks, a makeup area and a beautiful bay of windows. Just outside the primary suite is a separate office, perfect for working from home; the owners have also used this space as a fourth bedroom. The finished lower level adds tremendous additional living space with dimmable recessed lighting, built-in bookshelves and plenty of room to make the space your own. Use it as a family room, home bar, playroom, study, library or a combination of spaces. There is also an additional home gym. There truly is plenty of room for everyone. Additional features include central air on all three levels, two-zone central air with the upstairs system replaced, gorgeous hardwood flooring, a new hot water heater installed in August 2024, Pella windows, newer carpeting on the main level, upgraded electric, a one-car attached garage, and a second refrigerator and freezer that will remain. All COs are in place. Outside, the property is just as special. The park-like grounds surround a gorgeous in-ground pool, creating a spectacular private backyard retreat perfect for relaxing, entertaining and enjoying the warmer months. This is the kind of backyard everyone will want to gather in—an entertainer’s dream and your own private summer oasis. Located just moments from Berry Road Park, formerly Faber Farm, with access to hiking trails leading to Mombasha Lake, and offering deeded lake rights to Balder Lake, a private freshwater lake ideal for swimming, kayaking, non-motor boating and peaceful winter days of skating, this is more than a house—it is a property and lifestyle that are hard to duplicate. All of this is just minutes from shopping, dining, entertainment, schools, major roadways and the Harriman train station, while still feeling tucked away in a beautiful country setting. Located within the highly sought-after Monroe-Woodbury School District, with Pine Tree and Sapphire Elementary Schools nearby, this truly is one of those special Monroe properties that offers space, character, recreation, convenience and an incredible setting all in one.

27 Margaret Road, Monroe

$645,000

3 Beds ⋅ 3 Baths ⋅ 1039204 MLS

Elegance, Comfort and Quality Upgrades welcome you to this mint condition house. This extraordinary property offers a lifestyle that is both luxurious and inviting. From the moment you enter, soaring ceilings and oversized windows create an impressive sense of space while filling the home with an abundance of natural light. Radiant heat throughout provides year-round comfort, warming the beautiful travertine tile in the kitchen and complementing the rich hardwood floors throughout the home. At the heart of the house is an expansive, beautifully appointed kitchen featuring granite countertops, solid ashwood cabinetry, high-end appliances and a reverse osmosis water system. The main level continues with two bedrooms, a versatile guest room, a full bath, and an elegant living room highlighted by a striking stone fireplace. The living room opens to a charming enclosed front porch w/radiant heat, offering an additional space to relax and enjoy the peaceful surroundings. Upstairs, the luxurious primary suite provides a private retreat with soaring ceilings, a walk-in closet, Juliet balcony and a spacious spa-like bath featuring beautiful tile, a stone shower and a classic clawfoot tub. Outside, the home is embraced by beautifully landscaped grounds and the tranquility of nature. A new back deck provides the perfect setting for outdoor dining, entertaining, or simply enjoying the peaceful setting. LAKE RIGHTS adds another wonderful dimension to the lifestyle this property offers. Additional features include a whole-house security system, central vacuum, generator, new roof, gutters with leaf guards plus new hot water heater, furnace, and oil tank all updated in 2024. Impeccably maintained and thoughtfully enhanced, this magnificent property is more than a home; it is a rare opportunity to enjoy elegance, comfort, privacy, and nature in one exceptional setting. A Must See!

55 Interlochen Parkway, Monroe

$618,450

3 Beds ⋅ 2 Baths ⋅ 1037999 MLS

Set on a beautiful, private and quiet street in Woodbury, this unique 3-bedroom, 2-bath home offers 2,144 sq. ft. of living space with plenty of character inside and out and warm cedar cathedral ceilings extending through the main level and bedrooms. The main level features a spacious living room with a built-in bar, brick fireplace and loft above. A few steps up are all three bedrooms and a full bath, while the lower level offers the kitchen and dinette, another full bath, a large family room with fireplace, and an enclosed glass sunroom overlooking the wooded property. Multiple walkouts lead to expansive wraparound decks, with seasonal mountain views from the hilltop setting. The property also includes a detached car garage, separate car carport and front patio. Recent improvements include a new -heat and hot water- boiler, new oil tank, fresh paint throughout, some new flooring, some new lighting, a new refrigerator, and numerous interior and exterior updates. Located in the Monroe-Woodbury School District, this is a home that stands out for its privacy, setting and unique character.

15 Overlook Drive, Highland Mills

$449,000

3 Beds ⋅ 2 Baths ⋅ 1033721 MLS

Welcome to 66 Whitetail Run – Chester, NY. Tucked back from the road on an ample, tree-lined lot, this charming contemporary colonial offers the perfect blend of privacy and convenience in the Monroe-Woodbury school district. Surrounded by nature and filled with birdsong, this peaceful setting feels like a retreat while still being close to all local amenities. Step inside to a bright, open living room featuring soaring ceilings, a wood-burning fireplace, and oversized windows that flood the space with natural light. Hard floors flow throughout the main level, leading to a spacious eat-in kitchen with granite countertops, plus a formal dining room perfect for hosting gatherings and special occasions. This 3-bedroom, 1.5-bath home also offers both bathrooms newly renovated, along with the convenience of a main-floor laundry room with a new washer and dryer. An attached one-car garage adds everyday practicality, while the back patio invites you to unwind and enjoy the tranquil, wooded surroundings. Don't miss your opportunity to make this move-in ready home yours!

66 Whitetail Run, Chester

$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

$1,149,000

5 Beds ⋅ 3 Baths ⋅ 1020835 MLS

FINAL OPPORTUNITY — BEFORE IT BECOMES A RENTAL! The builder is giving buyers one final opportunity to own this exceptional new-construction with YEAR ROUND LAKE VIEWS before committing it to a rental. HOUSE AND PROPERTY OF THIS QUALITY, DRAMA AND CUSTOM FINISHES OVERLOOKING A LAKE IS A RARE FIND in this area! Just 60 minutes from New York City just beyond 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. AMENITIES LIST IN DOCUMENTS!

133 W Mombasha Road, Monroe

$750,000

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

$634,999

4 Beds ⋅ 3 Baths ⋅ 1013375 MLS

Rare opportunity in Chester! This 4-bedroom, 3-bath raised ranch sits on a private 2.5-acre lot and features a true 6-car garage — an uncommon and highly desirable feature that sets this home apart. The oversized garage offers exceptional flexibility: perfect for the car enthusiast, contractor, large family, or anyone who needs serious storage, a workshop, or space for boats, RVs, or equipment. Inside, the home offers 2,316 sq ft of comfortable living space with a practical raised-ranch layout, full basement, and room to expand or personalize. The private 2.5-acre setting provides privacy, outdoor space, and room to enjoy the Hudson Valley lifestyle while remaining convenient to major routes and amenities. Whether you’re looking for extra vehicle capacity, a home-based business space, or simply room to breathe, the 6-car garage combined with the acreage makes this a standout property in the area. Monroe-Woodbury schools. Schedule your showing today. Located in Orange County with easy access to major routes, this property delivers the space and privacy so many buyers are searching for — without sacrificing convenience. Whether you’re looking for a primary residence with room to grow or a peaceful retreat, 424 Laroe Road offers a strong foundation and exceptional land value. Key Features: 4 bedrooms | 3 bathrooms 2,316 sq ft 2.5 private acres Expansive deck for outdoor living Built 1974 – solid bones with modern potential Convenient Chester location Schedule your private showing today and experience the space, privacy, and potential for yourself.

424 Laroe Road, Chester

$649,900

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

$769,000

4 Beds ⋅ 4 Baths ⋅ 1013284 MLS

Truly one of a kind, fully renovated home. Offers privacy, yet close to everything, set on a hilltop overlooking a bubbling brook and Little Dam Lake! Commuters dream with just a short ride to Route 17 and the Thruway. Home features an oversized master bedroom with its own private bath and a wood sauna, library and decks on every floor.

1199 Mombasha Road, Monroe

$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

$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

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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.