Monroe-Woodbury Homes with Colonial Style

Welcome to the enchanting Monroe-Woodbury School District, nestled in the heart of Orange County, New York. Renowned for its commitment to educational excellence, this district serves a vibrant community that values quality learning environments for its children. With a diverse array of programs and extracurricular activities, Monroe-Woodbury empowers students to discover their passions and develop their talents in a supportive atmosphere. The district boasts highly qualified educators who are dedicated to fostering a love for learning, ensuring that students are well-prepared for their future endeavors.

As you explore the charming neighborhoods within this district, you will find an array of stunning Colonial-style homes that beautifully reflect the rich history and architectural elegance of the region. These timeless residences feature classic elements such as symmetrical facades, grand entrances, and inviting front porches, making them a popular choice for families seeking both style and comfort. With spacious layouts and well-manicured yards, Colonial homes provide the perfect backdrop for creating lasting memories with loved ones.

Living in the Monroe-Woodbury area not only offers access to exceptional educational opportunities but also a close-knit community that celebrates its residents. Enjoy the convenience of nearby parks, shopping, and dining, all while being surrounded by the natural beauty of Orange County. Whether you’re raising a family or looking for a serene place to call home, the Monroe-Woodbury School District and its Colonial-style houses create an ideal setting for a life well-lived. Come discover your dream home in this vibrant community today!

Newest Monroe-Woodbury Homes with Colonial Style

$879,900

4 Beds ⋅ 4 Baths ⋅ 1033613 MLS

Magnificent Colonial Residence COMING SOON in the Greens of Woodbury! Immaculate and move in ready, this 4 Bedroom 3.5 bath home is distinctly positioned on 0.77 acres of beautiful property purposely set back from the road and elevated to offer stunning views of the lush landscape and beautiful mountains as the backdrop. Experience luxury living in the sought after "Greens", a prestigious collection of upscale homes situated in arguably one of the best southern Orange County locations. Offered by the original owners (2002), pride of ownership shows throughout! There are gorgeous hardwood floors (this home is MINT!) along with both formal and informal spaces making the layout incredible for multi purpose areas. The Great room has soaring ceilings with the oversized windows and fireplace as the focal point. Outside, the grounds are beautifully landscaped offering a mix of perennial plantings, mature privacy trees and the backyard also includes an expansive deck perfect for outdoor entertaining with access off the Kitchen. There is a stunning Koi Pond with waterfall offering such a peaceful setting nearby the pergola and hot tub for added enjoyment. The two car garage is spacious and near it is a private side entry that makes it easy to bring in groceries right into the main level. This home is convenient to major routes including 32, the thruway, Palisades Parkway and more. Within minutes you'll reach popular shopping including the Woodbury Common Outlets, major transit lines include the train and express bus to NYC. This home is located in the Monroe-Woodbury school district. The lower Hudson Valley has so much to offer with beautiful state parks, nearby wineries & wonderful restaurants all just 1 hour outside of NYC with easy access to Westchester & NJ. An added perk is that Woodbury residents enjoy exclusive access to "The Rez" pond and newly redesigned pool with amenities galore! ***MORE information, special features sheet, floorplans and more will be available*** The town has just repaved Greenwich Ave and it looks spectacular! 58 Greenwich Ave is a very special property for the lucky buyer, will it be you?

58 Greenwich Avenue, Central Valley

$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

$440,000

3 Beds ⋅ 2 Baths ⋅ 1031034 MLS

Welcome to this charming single-family retreat set on a breathtaking, park-like lot surrounded by mature trees and lush, vibrant greenery. Inside, the home is bright, neutral, and move-in ready. Hardwood floors flow throughout, catching the natural light that pours in from generous windows in every room. The formal dining room is a true standout — featuring elegant crown molding and a graceful curved bay window it's the perfect setting for everything from weeknight dinners to holiday gatherings. Three large windows frame gorgeous views of the lush backyard, bringing the outdoors in. The kitchen is both functional and full of character, offering granite countertops, natural oak cabinetry, stainless steel appliances, and a large picture window overlooking the serene, tree-lined yard. Spacious bedrooms continue the home's warm, comfortable feel — hardwood floors, abundant natural light, generous closet space, and a versatile layout. Outside, the expansive grassy lot is truly the crown jewel. Mature trees provide shade, privacy, and a peaceful, retreat-like atmosphere that's rare to find. A charming wooden arbor, additional outbuilding for storage or a workshop, and a paved driveway round out this exceptional property. Homes this special don't stay on the market long. Schedule your private tour today — you'll fall in love the moment you pull up.

10 Park Avenue, Highland Mills

$799,000

4 Beds ⋅ 3 Baths ⋅ 1012284 MLS

Welcome to this beautifully charming Center Hall Colonial, privately set back from the road on a picturesque property with a tranquil man-made pond, fountain, and inviting wrap-around front porch. This spacious home offers the perfect balance of classic elegance and comfortable everyday living. The thoughtfully designed floor plan features a formal living room that flows seamlessly into the warm and inviting family room with a fireplace, creating an ideal space for entertaining. The spacious kitchen is appointed with granite countertops, a center island, abundant cabinetry, and sliders leading to an expansive deck overlooking the peaceful backyard. A formal dining room, powder room, and first-floor laundry complete the main level. Upstairs, the generous primary suite features a private ensuite bath, while three additional bedrooms share a full hall bath. A walk-up staircase leads to a full-house unfinished attic, offering outstanding potential for future living space. The finished walk-out basement provides even more room to relax or entertain, with sliders opening to a covered patio. An oversized two-car garage and a huge storage shed provide exceptional storage and convenience. Ideally located in the highly sought-after Monroe-Woodbury School District, this exceptional home combines timeless Colonial charm, abundant living space, beautiful outdoor amenities, and endless possibilities in a peaceful Chester setting.

197 Oxford Road, Chester

$599,900

4 Beds ⋅ 4 Baths ⋅ 1028003 MLS

Welcome to 27 Walton Terrace, where timeless Colonial architecture, thoughtful design, and an exceptional Hudson Valley lifestyle come together in one beautifully maintained residence. Featuring four bedrooms, three and a half bathrooms, and an incredibly versatile floor plan, this move in ready home offers the perfect blend of elegance, comfort, and everyday functionality. A charming covered front porch accented by beautiful stonework creates an inviting first impression, while the welcoming foyer opens to hardwood floors that flow throughout the main level. Designed for both everyday living and effortless entertaining, the spacious family room is anchored by a warm gas fireplace and seamlessly connects to the formal dining room before opening into the expansive kitchen, complete with stainless steel appliances, abundant cabinetry, and generous counter space. One of this home's most unique and desirable features is its two primary suites, offering exceptional flexibility for multigenerational living, or guests. The first-floor primary suite provides privacy and convenience with its own en suite bath, while an additional home office/den that could serve as a fifth bedroom and beautifully appointed full bathroom with dual vanities complete the main level. Upstairs, you'll find three generously sized bedrooms, including a spectacular second primary retreat featuring soaring cathedral ceilings, dual walk-in closets, and a spa inspired en suite bath with separate vanities and a relaxing whirlpool tub. Adding even more convenience, the home offers dual laundry hookups, with laundry areas on both the second floor and in the expansive walkout basement. The lower level provides endless possibilities, whether you envision a future recreation room, home gym, media room, office, or additional living space, while still offering abundant storage. Walk directly out to the concrete patio, creating a seamless transition to the backyard. Outside, you'll discover your own private retreat. A spacious rear deck overlooks the peaceful, fully fenced yard, while the patio below provides the perfect setting for outdoor entertaining. Adding to the home's appeal are optional lake rights for just $50 per year, providing access to a beautiful sandy beach and a private lake where residents can enjoy kayaking, canoeing, paddle boarding, and other non-motorized boating activities, offering a peaceful escape just moments from your front door. Perfectly positioned for commuters, the home is conveniently located near Route 17/I-86, Interstate 87 (New York State Thruway), and Route 6, with nearby park-and-ride bus service to Manhattan and regional rail options within a short drive. Enjoy all the beauty, recreation, and charm of the Hudson Valley while remaining well connected to New York City. 27 Walton Terrace offers the rare combination of generous living space, timeless style, modern convenience, and an outstanding lifestyle in one exceptional property.

27 Walton Terrace, Monroe

$879,900

4 Beds ⋅ 3 Baths ⋅ 1027864 MLS

Welcome to 48 Greenwich Ave in the coveted Greens of Woodbury, an in demand location surrounded by Hudson Valley's beautiful scenery as the backdrop. Coming in at over 3,200 sq.ft. this 4 Bedroom center hall colonial beautifully positioned on 0.76 acres will be sure to impress! The layout is incredible, as it caters to both formal and informal spaces. The great room is the heart of the home with a gorgeous fireplace as the focal point and easy flowing open concept with the spacious Kitchen and access to the large deck overlooking the private backyard. There is a dedicated first floor office with double doors and a nearby half bath. Enjoy refinished stunning hardwood floors throughout most of the main level. Upstairs all bedrooms are spacious and the primary bedroom spans the whole right side of the home. This well designed space has a private full bathroom and huge added sitting room or bonus space. In addition to the two levels, the lower level is the unfinished walkout basement with so many possibilities to finish for added recreational space or more! The double wide driveway leads to the 2 car garage for easy parking options and access to the main floor of the home, making it a breeze to bring in groceries. This home is located in the Monroe Woodbury school district. An added perk is that Woodbury residents enjoy exclusive access to the Rez pond and parks, along with the gorgeous newly renovated pool for total outdoor enjoyment. You'll love the convenience of this strategic location close to shopping including Woodbury Commons, restaurants, palisades parkway, interstate and several other main routes. Harriman state park is moments away with endless hiking trails and lakes. Special features sheet and more information including floor plans will be available. Coming soon, don't miss out!.

48 Greenwich Avenue, Central Valley

$949,999

3 Beds ⋅ 3 Baths ⋅ 1025597 MLS

Looking for resort style living in Monroe? Considering joining Mansion Ridge Golf Club or already a member, this house is ideal! Sitting on the 11th hole of the only NY state Jack Nicholas designed Mansion Ridge Golf Course in a gated community, is a 3 bedroom, 3 bath exceptional colonial style home offering privacy, security, and amenities with convenient access to NYC. Check out mansionridgehomes.com and mansionridgegc.com for more information on the community and golf club membership options. The chef style kitchen features high end appliances, including Sub Zero refrigerator/freezer, Viking gas range and double ovens, Miele dishwasher, and granite topped counters and island. For the homeowners comfort and assurance, there is a 14kW Kohler whole house generator, Grundfos water pressure pump, Kinetico water softener, and Centric whole house ventilation fan, and Rachio 15 zone sprinkler system. The 2 story great room with its Mendota linear gas fireplace leads to a Trex deck overlooking the golf course and majestic scenery beyond. The first floor primary bed and bath feature a walk-in closet with built-ins, stall shower, jetted tub, toilet closet, and double sinks. Oak hardwood floors featured throughout. Upstairs are two guest bedrooms joined by a full bath. The partially finished full daylight basement is large enough for gym, work space, theater area, or whatever you imagine. This special home is move-in ready and awaiting its next owner to enjoy the lifestyle. A home warranty offered with sale.

46 Mansion Ridge Boulevard, Monroe

$599,000

4 Beds ⋅ 3 Baths ⋅ 1020769 MLS

Welcome to this spacious Colonial nestled on over half an acre in one of Monroe's established neighborhoods. Offering over 2,300 square feet of living space, this 4 bedroom, 2.5 bathroom home features a functional layout designed for everyday living and entertaining. The main level includes a bright living room, formal dining room, eat in kitchen, and an inviting family room with a fireplace. Upstairs, you'll find four generously sized bedrooms, including a primary suite with a private bath. Hardwood floors add warmth throughout much of the home, while the full basement provides excellent storage or future finishing potential. Outside, enjoy the large backyard with plenty of room to relax, entertain, or play, along with an expansive deck overlooking the property.

4 Ironworks Road, Monroe

$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

$795,000

4 Beds ⋅ 3 Baths ⋅ 1023481 MLS

Welcome to this Custom Colonial offering almost 3,100 finished SQFT of beautifully designed living space perched up on a hill in Timber Crest Estates, an enclave of 15 homes in the heart of Highland Mills, town of Woodbury. This 4-bedroom, 3-full bath home features an open and inviting layout with 9-foot ceilings, freshly painted throughout, hardwood floors, and an abundance of natural light from oversized windows throughout. The main level offers a spacious eat-in kitchen with stainless steel appliances, a formal dining room, a dedicated office/den, and a full bath, providing flexibility for guests or multigenerational living. The dramatic two-story great room is the heart of the home, centered around a cozy gas fireplace, while sliding doors off the kitchen lead to a deck overlooking the backyard—perfect for outdoor dining and entertaining. Upstairs, the expansive primary suite serves as a private retreat with tray ceilings, a large walk-in closet and an ensuite bath featuring a Jacuzzi tub. Three additional generously sized bedrooms and a full hall bath complete the second level. The full unfinished walk-out basement offers endless possibilities for future finished living space, a home gym, or recreation area. Additional highlights include municipal water, sewer, and natural gas, as well as owned solar panels for increased energy efficiency and cost free electric! This exceptional home combines space, comfort, and convenience in one outstanding total package. This will not last, PRICED TO SELL!

5 Sherwood Court, Highland Mills

$958,900

4 Beds ⋅ 4 Baths ⋅ 1022832 MLS

This stately Colonial residence in Briarcliff Estates blends timeless architecture with modern comfort, offering an exceptional lifestyle in one of Monroe’s most desirable enclaves. Set on a beautifully landscaped property, the home presents a commanding brick facade, classic gabled rooflines, and manicured greenery that enhances its curb appeal. Inside, the layout is designed for both everyday living and effortless entertaining. The main level features sun-filled formal spaces, warm hardwood floors, and refined millwork that underscores the home’s traditional character. A gracious living room and elegant dining room flow seamlessly toward the heart of the home—an inviting family room anchored by a handsome fireplace and framed by large windows overlooking the grounds. The kitchen provides generous workspace, with granite countertops, abundant cabinetry, and a comfortable eat-in area perfect for casual meals. Upstairs, the home offers four well-appointed bedrooms, including a serene primary suite with a extra sitting area and private bath. The upstairs also offers another Master bedroom with it's own en suite. The additional two and a half bathrooms are tastefully finished, providing convenience and comfort for family and guests alike. Basement is unfinished but has rough-in for full bathroom, if the buyer wants to redesign the basement. Outdoors, the property continues to impress with lush lawns, mature plantings, and a peaceful setting that reflects the charm of Briarcliff Estates. The backyard also offers an outdoor kitchen for entertainment and relaxing with family and friends. Whether enjoying quiet mornings on the deck or hosting gatherings on the expansive grounds, this home delivers a refined lifestyle in a prime Monroe location.

3 Stahl Way, Monroe

$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 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

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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.