Monroe-Woodbury Homes for Sale

Welcome to the Monroe-Woodbury School District, a vibrant educational community nestled in the heart of Orange County, New York. Renowned for its commitment to academic excellence and holistic student development, this district serves the charming towns of Monroe and Woodbury, providing a nurturing environment where students can thrive both academically and socially.

The Monroe-Woodbury School District boasts a diverse array of educational programs tailored to meet the unique needs of its students, from early childhood education to advanced placement courses in high school. With a strong emphasis on innovation, the district integrates technology into the classroom, preparing students for the challenges of the modern world. Extracurricular activities abound, offering students opportunities to explore their interests in sports, arts, and community service, fostering a well-rounded educational experience.

For families looking to settle in this exceptional district, the real estate market offers a variety of homes for sale that cater to diverse lifestyles and budgets. Whether you’re seeking a cozy single-family home with a backyard for the kids to play in, or a spacious modern abode with stunning views of the Hudson Valley, Monroe-Woodbury has something for everyone. The community is characterized by its friendly neighborhoods, excellent amenities, and proximity to outdoor recreational activities, making it an ideal place to call home.

Embrace the opportunity to be part of a thriving community that values education and quality living. Explore the available homes for sale in Monroe-Woodbury today and discover your perfect family haven!

Newest Monroe-Woodbury Homes for Sale

$824,900

4 Beds ⋅ 4 Baths ⋅ 1050809 MLS

Welcome to your “Private Country Club”! THE POOL and pool house are now open, but only for two more weeks! This gorgeous home is priced to sell! There is attention to detail and decorator touches throughout! First, you’ll enter the large, two-story foyer, which welcomes your guests with its soaring, vaulted ceiling, Palladium window, inlaid wood floor, and custom picture moldings! The lovely dining room is enhanced by inlaid wood floors,modern wall sconces, chair rails, and moldings. The bright, and inviting Family Room, features a stunning, white marble-front, wood-burning fireplace, inlaid wood floors, and large, sliding doors that showcase the breathtaking view of the garden and open to the deck. You’ll love creating new dishes, in the TRULY "PROFESSIONALLY OUTFITTED" kitchen, with 6-burner Viking range, PLUS BOSCH DOUBLE OVENS (w/ many options for baking, & roasting). There are THREE ovens total! The Bosch ovens are less than 5 years old! There is a large, EXTRA-THICK iSLAND with beveled edge & PREP SINK (perfect for 2 chefs working side-by-side),a top-of-the-line refrigerator, 4 yr.old dishwasher, pantry, & desk.There is a large ROUND GRANITE TABLE THAT SEATS 5-6, with beveled edge (matches the granite throughout the kitchen), IN THE SUNNY, BAY-WINDOWED BREAKFAST AREA with view of yard. Upstairs, the stunning Primary Ensuite has a vaulted ceiling, wood floors, dressing alcove, recessed lighting, AND a windowed sitting room, which overlooks the gardens below. The elegant Ensuite Bath features a tray ceiling, beautiful Jacuzzi tub, Travertine marble tiles, a tumbled- marble shower with wall jets and bench, a bidet, Toto toilet, new granite counters & sinks, new faucets, new light fixtures & extra towel rods. One of the best features is an extra walk-in closet in the Primary bathroom (with shelving).The other bedrooms are oversized and sunny, with wood floors, and big windows (One bedroom features lovely wainscoting) The LAUNDRY IS UPSTAIRS with new storage cabinets. There is a fabulous, heated 20 x 40’ pool with fiberglass coating (no vinyl liner),custom steps, and "Sunshelf", surrounded by extended paver decking… plus a SPACIOUS POOL HOUSE (kitchenette, 1/2 bath,and lovely lounge)! After you’ve finished swimming, you can relax in the shade of the POOL HOUSE, with a glass of iced tea, prepared right there! Tall, stately trees line the the property. There are beautiful black gates, and a stunning paver staircase leading from the side-load driveway to the backyard. Tall grasses are another beautiful source of privacy in the summer. There are “Specimen trees” in both the front and back of the home (over $100k in exterior upgrades), TWO pergolas (one perfect for a BBQ grill, AND one for a table & chairs),a flagstone patio,and a huge deck for several furniture groupings! There are numerous places to entertain friends and family! Among the numerous recent upgrades are another new central a/c compressor (the home has two), and a GORGEOUS NEW PAVER PATH (framed by a beautiful border)that leads visitors to the front door! The solar panels (owned, not rented), AND extra, blown-in insulation in the attic, provide SAVINGS on the heating & electric bills year-round.The versatility of the finished basement is perfect for working out, gaming, & watching movies. PLUS there is an extra room, and a BEAUTIFUL, full bathroom. *Monroe-Woodbury Schools. COMMUTING IS EASY…Close to Palisades Pkwy, & NYS Thruway. Spend the day @ Woodbury Park, or John Burke pool- exclusive to Woodbury Residents offering a beach, parks, ball fields, picnic pavilions,life-guard pool, & DAY CAMP. It is less than 3 miles to I87, Route 6, & Route 17. It is 60 miles to NYC, 15 minutes to West Pt. and minutes to Stewart International Airport. World class shopping is only 1 1/2 miles away @Woodbury Commons Factory Outlets. Enjoy the local farmers markets, & hiking trails with breathtaking views!

9 Roselawn Road, Highland Mills

$675,000

4 Beds ⋅ 4 Baths ⋅ 1050748 MLS

Nestled along a tranquil cul-de-sac within a premier neighborhood, this resplendent home sits on a private, corner lot, surrounded by lush, verdant grounds. Inside, the house boasts a thoughtful and seamless floor plan. The gourmet kitchen features a generous layout with bespoke finishes. An architectural fireplace anchors the spacious living area, creating a cozy, soothing atmosphere. The luxurious master suite serves as a serene sanctuary. A versatile, fully finished lower level provides endless convenience. This home truly represents the absolute pinnacle of sophisticated urban living.

129 Linden Lane, Monroe

$550,000

4 Beds ⋅ 3 Baths ⋅ 1041577 MLS

From the covered front porch to the spacious backyard, this four-bedroom, two-and-a-half-bath home offers plenty of room to live, gather and enjoy. Inside, hardwood floors flow through the bright living and dining rooms, while the kitchen features ample cabinetry, generous counter space and a center island. The vaulted family room with fireplace is the heart of the home, creating a warm and inviting space to relax or entertain. Upstairs, the spacious primary suite includes a private bath with a soaking tub and separate shower, along with three additional bedrooms and another full bath. Sliding doors lead to an expansive rear deck overlooking the fully fenced backyard. Solar panels with battery backup provide energy efficiency and added peace of mind. A dedicated laundry room, unfinished basement and attached two-car garage add the storage and everyday functionality every home needs, all in a convenient location.

16 Cambridge Circle, Monroe

$779,900

4 Beds ⋅ 3 Baths ⋅ 1050193 MLS

PRIVATE WOODED COLONIAL!! 4 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat In Kitchen with Granite Counter Tops, Stainless Steel Appliances & Pantry! Master Bedroom Suite with Walk In Closet! Living Room with Wood Burning Fireplace & Built-Ins! Large Formal Dining Room with French Doors! Crown Molding! Gleaming Hard Wood Floors! Recessive Lighting! Walk Up Attic & Full Basement for Endless Possibilities! Two Story Entry/Foyer! Deck with Beautiful Awning! Over Sized Driveway for Plenty of Parking! Perfect Commuter Location! Close to Major Highways, Buses & Shopping!

1168 Craigville Road, Chester

$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

$419,900

3 Beds ⋅ 2 Baths ⋅ 1050001 MLS

Welcome to this charming 3-bedroom, 1.5-bath home located in the heart of the Village of Monroe. Featuring durable vinyl siding and beautiful curb appeal, this property beautifully combines comfortable indoor living with outdoor enjoyment. Key Interior Highlights • Spacious Living & Dining: Large, inviting main-level rooms perfect for entertaining and everyday living. Bay window in dining room adds additional light. • Comfort Features: Ceiling fans throughout most rooms ensure year-round airflow. Downstairs offers large window air conditioning unit. • Bedrooms: Staircase with wide wooden bannister leads upstairs to the bedrooms. The spacious primary suite features a double closet, while the second bedroom comfortably fits a queen-size bed. The flexible third bedroom is ideal for a single bed or a private home office. • Ample Storage: Includes functional under-eave storage, an upstairs bathroom with dedicated linen cubbies, pull-down stairs to an attic, and a full, unfinished basement handling laundry, utilities, and extra storage. Exterior & Property Features • Outdoors: Relax on the private deck under a covered porch overlooking a level, manicured yard filled with mature landscaping and flowering trees. • Extra Space: A generous side yard provides the perfect layout for recreation, paired with a private driveway and a 1-car garage. • Modern Conveniences: Fully connected to municipal water, sewer, and natural gas. Location & Commuter Perks • Top-Tier Schools: Located in the highly sought-after Monroe-Woodbury School District, with a local elementary school just a short distance away. • Unbeatable Convenience: Minutes from major shopping centers like Woodbury Common Premium Outlets, Walmart, Target, Home Depot, BJs, and local grocery stores. • Recreation Nearby: Close to Airplane Park, the scenic Mill Ponds, and the Heritage Trail. Great view of annual fireworks without leaving home. Nearby attractions include Mansion Ridge Golf Course, LEGOLAND, West Point, and the Castle Fun Center. • A Commuter’s Dream: Located just 1 hour from NYC with seamless highway access to Route 17, Route 6, the Palisades Parkway, and the NYS Thruway (I-87). Public transit is a breeze with an NYC bus stop just 1/3 of a mile away and the train station only 10 minutes from your door. Come see this delightful village home today and make it yours!

27 Ash Street, Monroe

$750,900

4 Beds ⋅ 3 Baths ⋅ 1045931 MLS

Welcome home to this impressive 3,400-square-foot custom L-shaped Colonial, privately situated in the Village of Monroe, offering the perfect combination of privacy, space, and convenience. Drive up the beautiful circular driveway surrounded by perennial gardens and arrive at the inviting covered front porch. Step inside to beautiful hardwood floors and spacious living areas. The family room features a cozy fireplace, while the additional living room offers a charming wood-burning stove. At the heart of the home is an exceptionally spacious kitchen with an oversized center island, providing ample room for meal preparation, casual dining, and gatherings. The kitchen overlooks a comfortable sitting area and the peaceful, private backyard. Just off the kitchen is a spacious dining room, providing the perfect setting for entertaining and hosting holiday gatherings, and creating lasting memories. Upstairs, you’ll find four generously sized bedrooms, Plenty of closets, including a spacious primary suite with a private full bath, whirlpool tub, and a huge walk-in closet. A newer roof with solar panels adds an energy-efficient feature to this wonderful home. The full, unfinished basement provides ample storage and excellent potential for additional living or recreational space. Step outside and enjoy your own private retreat surrounded by peace, quiet, perennial gardens, and tranquility, yet you’re conveniently located close to schools and within walking distance to shopping, parks, restaurants, the Heritage Trail, and public transportation. Woodbury Common Premium Outlets and many other Hudson Valley attractions are just minutes away, with New York City approximately one hour away. A rare opportunity to enjoy privacy and tranquility without sacrificing the conveniences of Village living.

87 Summit Street, Monroe

$499,000

3 Beds ⋅ 3 Baths ⋅ 1049026 MLS

This beautifully updated Chester home in the Monroe-Woodbury School District sits on 1.5 acres with a level open yard, a creek, and a wooded backdrop. From the moment you arrive, the paver walkway, landscaping, and inviting curb appeal set the tone. Inside, the main level boasts hardwood floors and an open layout with a brand-new kitchen featuring white cabinets, granite counters, and stainless steel appliances, plus a living and dining area with sliding glass doors to the deck and backyard. The first floor also has a full hallway bath and three bedrooms, including a bright primary suite with custom windows, crown molding, and an updated ensuite bath with custom tile and glass shower doors. The lower level offers a large den with a stone fireplace and wood-burning stove insert, a half bath, laundry room, and access to the attached two-car garage. Outdoor spaces include a deck off the kitchen and a covered deck from the den, perfect for relaxing or entertaining. The expansive yard is ideal for recreation, gardening, or gatherings, with the creek and woods adding privacy. Just 57 miles to NYC, this home offers both tranquility and easy access to amenities, including nearby parks with 1,500 acres of trails, playgrounds, and more. Additional perks include central air, newer siding, roof, oversized energy-efficient windows, shed, oil burner, hot water heater, and several updated appliances. Conveniently located near shopping, major highways and public transportation.

264 Bull Mill Road, Chester

$625,000

4 Beds ⋅ 3 Baths ⋅ 1049487 MLS

Unique in layout and filled with modern flair, 10 Karen Drive in Monroe NY is a perfect home for multigenerational lifestyle. This sun-filled 4 bedroom , 3 full bath raised ranch is in pristine condition and offers an impressive array of thoughtful updates and improvements. Beautifully renovated European-style custom kitchen is truly a standout in design and space. The oversized primary en-suite offers a private full bathroom. Newer hardwood floors flow through-out the living and dining areas and hallway, while nearly all windows have been replaced for added comfort and efficiency. Perfect for those seeking a distinctive home on two and half acres, low taxes, solar system and on a private road.

10 Karen Drive, Monroe

$479,999

3 Beds ⋅ 3 Baths ⋅ 1049258 MLS

Welcome home to this beautifully custom-renovated 3-bedroom, 2.5-bath townhouse nestled on a quiet cul-de-sac in the highly sought-after Timber Ridge III community of Highland Mills. Offering approximately 1,963 square feet of living space, including the finished basement with an impressive oversized his-and-hers walk-in closet, this move-in-ready home combines modern style, comfort, and convenience. Step inside to a bright, open-concept layout featuring tasteful custom renovations and designer finishes throughout. The living, dining, and kitchen areas flow seamlessly together, creating an inviting space perfect for everyday living and entertaining. Upstairs, the spacious primary suite offers a private en-suite bath and an impressive oversized his-and-hers walk-in closet with abundant storage. Additional bedrooms provide plenty of space for family, guests, or a home office. Enjoy outdoor living on the private rear deck, perfect for morning coffee, relaxing in the sun, summer barbecues, and entertaining. Residents of Timber Ridge III also enjoy access to the community pool. Located in the Town of Woodbury, the home is approximately five minutes from Earl Reservoir Park, offering swimming, fishing, picnic areas, playgrounds, sports courts, and scenic walking paths. You'll also enjoy convenient access to Woodbury Common Premium Outlets, I-87, Route 17, commuter transportation, Harriman State Park, shopping, restaurants, and everyday conveniences. Located within the Monroe-Woodbury Central School District, 19 Helene Circle offers an exceptional combination of space, style, location, and Hudson Valley living. You will appreciate being located within the highly regarded Monroe-Woodbury Central School District, known for its strong academic programs, championship athletics, performing arts, Advanced Placement courses, and wide variety of extracurricular opportunities. Being sold As-Is. Refrigerator and chandeliers are excluded from the sale.

19 Helene Circle, Woodbury

$269,900

2 Beds ⋅ 2 Baths ⋅ 1049236 MLS

Welcome home to this beautifully updated 2-bedroom end-unit townhouse offering the perfect blend of comfort, style, privacy, and convenience. This move-in ready home presents a rare opportunity to own a residence that has been lovingly maintained and thoughtfully updated throughout the years. Featuring gorgeous new flooring, a stunning new kitchen with modern finishes, beautifully renovated bathrooms, gas heat, and gas cooking, central air, every detail has been carefully curated for today's lifestyle. Now let's discuss LOCATION! Step outside to your own private outdoor retreat featuring an exceptional custom paver patio with brilliant hardscaping, creating the perfect setting for entertaining, dining al fresco, or simply relaxing while enjoying peaceful wooded views and added privacy. As an end unit backing to the woods, you'll appreciate the added sense of space and tranquility rarely found. You will also love your own carport. An exclusive space w/ added storage area. Additional parking is also available. Located in a highly desirable community with amenities galore, residents enjoy access to Woodbury Recreation, swimming pools, the reservoir, beach areas, playgrounds, sports courts, walking trails, and a variety of year-round activities and events. New York City commuter-friendly and ideally situated just minutes from Woodbury Common Premium Outlets, West Point Military Academy, Bear Mountain State Park, Harriman State Park, major highways, dining, shopping, and recreation. Whether you're searching for a full-time residence or a weekend retreat, this exceptional townhouse offers low-maintenance living and an unbeatable Hudson Valley lifestyle in a picturesque setting. Opportunities to purchase a one-owner home with this level of care, updates, privacy, and location are truly rare.

13 Redwood Drive, Highland Mills

$419,000

3 Beds ⋅ 1 Baths ⋅ 1049008 MLS

Sun-filled from the moment you enter, this 3-bedroom home offers a warm, welcoming interior surrounded by spacious property, with Sapphire Lake access only a 3-minute walk away. The bright entryway opens into the living room, where a beautiful stone fireplace with an energy-efficient wood stove insert brings character to the heart of the home. An eat-in kitchen plus formal dining room provide space for everyday meals and gatherings. Recent improvements include a newer roof, new hot water heater, updated appliances, water softener, washer/dryer, and new leach fields. A one-car garage, multiple parking spaces, and large shed add valuable storage. Lake rights offer access to swimming, kayaking, fishing, and non-motorized boating. Conveniently located near the Village of Harriman, Woodbury shopping, dining, Metro-North, and major commuter routes, with NYC approximately one hour away. Easy commute to NYC by bus or train. Located in the Monroe-Woodbury School District.

101 Highland Road, Monroe

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