Monroe-Woodbury Homes with Raised Ranch Style

Welcome to the enchanting Monroe-Woodbury School District, nestled in the heart of Orange County, New York. This vibrant community is celebrated for its commitment to academic excellence and holistic development, making it an ideal environment for families. With a strong emphasis on education, Monroe-Woodbury offers a range of programs designed to cater to diverse learning styles and interests. From innovative STEM initiatives to a rich array of arts and athletics, students are encouraged to explore their passions while receiving a top-notch education. The district’s dedicated educators and supportive community work together to ensure that each child thrives, creating a nurturing atmosphere that extends beyond the classroom.

In addition to its educational offerings, Monroe-Woodbury is known for its charming neighborhoods, particularly those featuring raised ranch-style homes. These distinctive residences are characterized by their split-level designs, offering a unique blend of functionality and style. Raised ranch homes typically feature spacious living areas, inviting kitchens, and ample outdoor space, making them perfect for family gatherings and entertaining. The elevated layout not only maximizes natural light but also provides stunning views of the surrounding landscape, allowing residents to fully appreciate the beauty of Orange County.

Living in Monroe-Woodbury means enjoying a perfect balance of suburban tranquility and easy access to urban amenities. With its top-rated schools, beautiful homes, and a welcoming community, it’s no wonder that this area is a sought-after destination for families looking to plant their roots. Discover the charm of Monroe-Woodbury, where education and home come together in perfect harmony.

Newest Monroe-Woodbury Homes with Raised Ranch Style

$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

$550,000

3 Beds ⋅ 2 Baths ⋅ 1028087 MLS

BiLevel/Raised Ranch on Quiet Street with Room to Grow! Come home and relax on the upper level deck overlooking state land that offers additional privacy. This well-maintained home clearly shows the pride of ownership. Open concept living room and dining room features many windows that fill the home with natural sunlight. Enjoy the convenience of the updated full bathroom and three comfortable bedrooms. The full basement provides endless possibilities for additional finished living space, home office, gym, or recreation area. Major upgrades include the new main bathroom, new roof. Step outside to a fenced-in yard and upper level deck, ideal for relaxing, pets, or gatherings, all set on a quiet, low-traffic street. Backyard also accessible from basement sliders. Perfect commuter location — close to all the Hudson Valley has to offer: lakes, hiking trails, shopping, major highways, trains, and buses. Opportunity knocks. Don’t miss it!

56 Poplar Drive, Monroe

$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

$529,900

4 Beds ⋅ 3 Baths ⋅ 1023187 MLS

Tucked away at the end of a long private driveway on 3.4 acres, this beautifully updated home offers the perfect blend of privacy, nature, and everyday convenience. Surrounded by mature trees, scenic mountain views, and a picturesque pond shared with one neighboring property, this one-of-a-kind retreat feels like your own private oasis, yet is just minutes from shopping, restaurants, schools, and major commuter routes in the highly sought-after Monroe-Woodbury School District. Freshly painted inside and out, this spacious home offers 2,233 square feet of living space, plus a spectacular 224-square-foot enclosed cathedral-ceiling porch surrounded by walls of windows that bring the outdoors in. Whether you're enjoying your morning coffee, watching the changing seasons, or simply taking in the peaceful views, this remarkable space is sure to become your favorite room in the house. Natural light pours through oversized picture windows, highlighting the warm and inviting living spaces. The living room and expansive family room are anchored by a dramatic floor-to-ceiling two-sided brick fireplace, while a second fireplace with a wood-burning stove adds warmth and character, creating inviting spaces for relaxing and entertaining. The spacious eat-in kitchen offers abundant cabinetry and generous workspace, flowing effortlessly into the dining area for everyday living and special occasions. The home features four generously sized bedrooms, including a primary suite with a walk-in closet, along with two beautifully updated full bathrooms and a convenient half bath. The lower level offers an expansive family room with a separate entrance, providing outstanding flexibility for a home office, guest quarters, multigenerational living, or a home-based business. Step outside onto the newly refreshed oversized deck overlooking your backyard, where nature becomes part of everyday life. The expansive cleared lawn offers endless space for soccer games, baseball, gatherings, and entertaining, while wooded walking paths lead to the pond. Spend peaceful evenings by the water, enjoy fishing, watch deer and birds from your deck, or simply relax and take in the serenity that makes this property so special. Additional highlights include a two-car garage, central vacuum, generous storage throughout, two beautifully updated full bathrooms, a recently refreshed oversized deck, and the peace of mind of a recently removed underground oil tank with proper documentation. Properties offering this rare combination of acreage, mountain views, a picturesque pond, and an established neighborhood setting seldom become available. Completing this exceptional offering are deeded lake rights to Balder Lake (just down the street, if you choose to join)—a private freshwater lake ideal for swimming, kayaking, non-motor boating, fishing, and peaceful winter days spent skating. This is more than a house—it's a property and lifestyle that's hard to duplicate.

27 Jean Drive, Monroe

$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

$649,000

4 Beds ⋅ 3 Baths ⋅ 1005912 MLS

4 Sequoia Trail is a beautifully renovated 2,004 sq ft residence that seamlessly blends comfort, style, and convenience. Set on landscaped grounds with plenty of outdoor space, it offers a peaceful retreat while being near local attractions. The bright living room, featuring oversized windows and an elegant fireplace, flows into a delightful dinette area. The kitchen boasts contemporary cabinetry and a spacious deck for entertaining. The home includes four bedrooms with great storage, two modernized bathrooms, and a finished basement providing extra living space. A two-car garage and a well-kept yard round out this move-in-ready property, ideal for modern living.

4 Sequoia Trail, 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

$950,000

4 Beds ⋅ 3 Baths ⋅ 1011686 MLS

Well-maintained and updated 4-bedroom home situated on a quiet cul-de-sac. Features spacious living area, an oversized deck, in-ground pool, large backyard, and 2-car attached garage. Framed by mature trees, offering privacy and convenience in equal measure. Ideally located near Kiryas Joel, South Blooming Grove, shopping, and everyday amenities. An exceptional blend of space, comfort, and location. Experience all this property has to offer—schedule your private showing today.

11 Cliff Court, Monroe

$599,999

4 Beds ⋅ 2 Baths ⋅ 1006054 MLS

Welcome to 5 Columbia Circle, a turn-key raised ranch tucked inside the gated Highland Lake Estates community in Highland Mills. From the moment you arrive, this home delivers what most listings only promise: modern updates, real peace of mind, and a backyard that earns its keep. Four bedrooms plus an office/den give you room to live and work without compromise. Two full bathrooms, California Closets in every upstairs bedroom, Pella doors, and Andersen 400 Series windows reflect a home maintained with discipline, not shortcuts. The mechanicals back it up: hot water heater (2021), whole-house water softener and filtration system (2023), and an upgraded back deck (2019) built for those gorgeous Hudson Valley sunsets. Comfort and security are handled. A heated garage with its own thermostat means projects don't stop in January. A central-station monitoring system covers fire, burglary, low-temperature, and carbon monoxide, plus camera coverage for complete confidence. The fenced backyard and lawn sprinkler system round out a property that's genuinely move-in ready. Location is the quiet advantage here. The Metro-North Harriman station sits under 10 minutes away, with NYC roughly 50 miles and about an hour out via I-87 and Route 17. Woodbury Common Premium Outlets, grocery, and everyday essentials are a short drive down Route 32. Weekends open up fast: Harriman State Park and Bear Mountain for hiking, nearby golf, and local wineries and farms that make Orange County living what it is. This is the rare home where the big ticket items are already done and done right. All that's left is to move in, relax and watch the sun go down right off your back deck.

5 Columbia Circle, Highland Mills

$599,000

3 Beds ⋅ 2 Baths ⋅ 1006128 MLS

Welcome to this spacious raised ranch in the heart of Monroe, offering comfort, flexibility, and great outdoor living on a generous .72-acre lot. This well-maintained home features 3 bedrooms and 1.5 baths with approximately 1,748 sq ft of living space. The main level offers a bright and inviting layout with an eat-in kitchen complete with stainless steel appliances, a brick backsplash, double sink, ceiling fan, and charming beamed ceiling. Sliding glass doors lead right out to the deck—perfect for morning coffee or quiet evenings. The kitchen flows seamlessly into the dining room, creating an ideal space for gatherings. You’ll find a full bathroom, a primary bedroom, and two additional nicely sized bedrooms on the main level, along with a convenient laundry area. The lower level expands your living space with a second family room, an additional bathroom, and two bonus rooms currently being used as bedrooms. This level also includes a second laundry area, tiled flooring, extra cabinetry for storage, and a second refrigerator. Walk-out access leads directly to the backyard. Step outside to your private outdoor retreat featuring a large backyard with a heated in-ground pool, patio, and deck—ideal for summer entertaining. A storage shed adds even more convenience. Close to shopping, Woodbury Commons, walking distance to local golf courses, public transportation and less than 60 miles New York City. Making this home a commuters dream! A versatile home with plenty of space both inside and out—don’t miss this opportunity!

70 Bayberry Drive, Monroe

$549,900

3 Beds ⋅ 3 Baths ⋅ 999789 MLS

Bright. Immaculate. Effortlessly Elegant. Nestled in one of Monroe's most desirable executive neighborhoods, this immaculate 3-bedroom, 2.5-bath bi-level offers 1,932 square feet of beautifully maintained living space and is truly move-in ready. Filled with natural sunlight throughout, this stunning home exudes warmth and pride of ownership from the moment you enter. The spacious upper level features an inviting living room, dining area, and well-appointed kitchen, while the open lower level provides exceptional additional living space perfect for entertaining, relaxing, or hosting gatherings. A dramatic floor-to-ceiling fireplace creates a striking focal point and adds character and charm to the home's inviting atmosphere. The primary suite offers a private retreat with its own full bath, while two additional generously sized bedrooms and spacious bathrooms provide comfort and flexibility. Step outside onto the deck and enjoy your morning coffee, summer barbecues, or peaceful evenings overlooking the beautifully maintained property. Every detail of this home has been thoughtfully cared for, creating a seamless blend of comfort, style, and functionality. Located within the highly sought-after Monroe-Woodbury School District and surrounded by executive-style homes, this exceptional residence offers the perfect combination of location, space, and turnkey condition. A rare opportunity to own a meticulously maintained home in one of Monroe's most established and sought-after neighborhoods.

31 Laura Road, Monroe

$529,000

3 Beds ⋅ 3 Baths ⋅ 898870 MLS

Some lots just have good bones. This one has it's own private nature trail, stocked pond rights, and a cul-de-sac that dead-ends into miles of nature trails anchored by a solid, spacious raised ranch on 1.8 acres. Inside, the home has been partially updated and offers solid bones with room to add your own touch over time. The house delivers where it counts. Three bedrooms, two and a half baths, large kitchen, a two-car garage, and a three-season room and deck that make the most of a property this beautiful. The woodburning stove in the basement helps the winter months stay cozy while saving on fuel oil bills. Multiple outbuildings including a shed and a playhouse that will get more use than you'd expect. The lawn and mature landscaping are genuinely impressive — the kind that takes years to establish and shows the moment you pull in the driveway. Then there's everything else. When not playing on the impeccable lawn, the kids could be kids catching frogs and fish, climbing trees and building forts in the woods.. All without leaving the property. When they do, the trail into Goosepond Mountain State Park is just a few doors down, at the end of the Cul de Sac.. The street itself is unhurried and unpretentious — picture dads teaching kids to ride bikes in the road, strollers, joggers, dogs on leashes and kids swarming ice cream trucks. With easy access to amenities and a realistic commute to NYC, Booth Rd means you don't have to choose between the life you want and the job that funds it. Come feel it. The land speaks for itself.

94 Booth 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.