Monroe-Woodbury Homes with Driveway Parking features

Welcome to the beautiful Monroe-Woodbury School District, nestled in the heart of Orange County, New York. This vibrant community is renowned for its commitment to educational excellence, making it a prime choice for families seeking a nurturing environment for their children. The district boasts a diverse range of academic programs, dedicated teachers, and a wealth of extracurricular activities that foster both personal and intellectual growth. With a strong emphasis on student achievement, Monroe-Woodbury consistently ranks among the top school districts in the state, providing students with the tools they need to succeed in their future endeavors.

In addition to its outstanding educational offerings, the Monroe-Woodbury area is characterized by its charming neighborhoods and family-friendly atmosphere. Homes in this region often feature the convenience of driveway parking, a sought-after amenity for busy families and professionals alike. Imagine the ease of coming home to your own private space, where you can park your vehicle with ease and enjoy the comfort of your surroundings.

Whether you are looking for a cozy single-family home or a spacious property that accommodates your growing family, the Monroe-Woodbury area has something for everyone. With its picturesque landscapes, welcoming community, and proximity to major commuting routes, this area is not only a great place to live but also a fantastic investment for your future. Explore the homes available in this charming region and discover why so many families are proud to call Monroe-Woodbury home!

Newest Monroe-Woodbury Homes with Driveway Parking features

$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

$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

$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

$389,000

4 Beds ⋅ 1 Baths ⋅ 1046180 MLS

Welcome to 4 Grove St, a charming and private residence nestled in the heart of Harriman, NY. This inviting home offers 4 spacious bedrooms and a total of 7 bright, versatile rooms—perfect for living, entertaining guests, or creating your ideal home office or playroom. Set on a generous 0.7-acre lot, the property provides ample outdoor space for relaxing, gardening, or enjoying gatherings in your own secluded oasis. Enjoy the peace and privacy of a standalone house while being conveniently located near local amenities and major routes. Discover comfort, space, and tranquility at 4 Grove St—your next place to call home. 3 Minute drive to major to Woodbury Common Mall! Rare opportunity to find, less than 400k!

4 Grove Street, Harriman

$459,000

4 Beds ⋅ 2 Baths ⋅ 1047996 MLS

Welcome to this charming 4-bedroom, 2-bath bilevel, ideally situated on a quiet dead-end street. The inviting open floor plan offers a seamless flow for everyday living and entertaining, with beautiful hardwood floors throughout the main level and a spacious kitchen featuring stainless steel appliances. Enjoy year-round comfort with central air and take advantage of the large deck overlooking a flat, fully fenced backyard, providing the perfect space for outdoor entertaining, relaxing and play. With Monroe-Woodbury Schools, low taxes, and an excellent commuter location, this home offers the ideal combination of comfort, convenience, and value. Don’t miss the opportunity to make this wonderful home your own!

8 Townsend Place, Chester

$412,000

3 Beds ⋅ 1 Baths ⋅ 1044454 MLS

Built for easy, manageable living. Set on a corner lot, this 3-bed, 1-bath ranch has a welcoming presence from the moment you approach, complemented by an oversized driveway and front deck. Inside, the main living spaces feel open and connected while maintaining a sense of distinction, offering a comfortable layout with functionality in mind. A nicely-sized entrance foyer invites you in before giving way to the living, dining, and kitchen areas, while the bedrooms and bathroom are positioned on the opposite side. Laundry is tucked away and conveniently located between the bedrooms, and the utility room can be accessed through the bathroom or outside around the back. Adding another layer to the home, the front deck, back patio, and spacious side yard create multiple spaces for everyday life to extend outdoors. As an added bonus, the property includes deeded lake rights to Walton Lake, further extending the enjoyment of home beyond the property itself. Take advantage of access for fishing, non-motor boating, swimming, and lounging lakeside. This is a place that simply makes sense for everyday living, with added recreation that brings even more to the experience of calling it home.

21 Midway Drive, Monroe

$449,555

3 Beds ⋅ 2 Baths ⋅ 1046409 MLS

Welcome to this beautiful and inviting Colonial! This charming 3-bedroom, 1.5-bath home offers the perfect blend of comfort, style, and modern updates in a highly desirable area. Step inside to find brand-new, high-quality vinyl flooring and recessed lighting throughout the home, creating a fresh, modern, and welcoming atmosphere. The spacious eat-in kitchen features brand-new cabinetry, while the oversized living room and separate dining room offer plenty of space for entertaining and everyday living. Numerous windows throughout the home provide an abundance of natural light, and ample closet space offers plenty of storage. The second-floor full bathroom includes a convenient laundry hookup located in the closet, adding functionality and ease to your daily routine. Enjoy peace of mind with several major recent upgrades, including a brand-new roof and newly paved driveway, both completed just one month ago, along with a brand-new hot water tank and boiler. It’s ready to be made your own. Outside, enjoy a great front porch where you can relax and take in peaceful views, along with plenty of front, back, and side yard space for entertaining, relaxing, and outdoor activities. A convenient shed provides additional storage. The location is ideal for both convenience and entertainment. Just 8 minutes from Woodbury Common Premium Outlets, with major shopping, restaurants, and everyday conveniences close by. Enjoy easy travel with Stewart International Airport approximately 22 minutes away and plenty of entertainment for all ages, including LEGOLAND New York approximately 25 minutes away. Outdoor enthusiasts will love being approximately 20 minutes from Bear Mountain State Park, where you can enjoy hiking, biking, boat paddling, barbecuing, carousel , basketball courts, playground, the community pool, zoo, and seasonal ice skating. The home is also conveniently located near public transportation and schools, making it an excellent choice for commuters and people looking to enjoy outdoor activities. Highly desirable location, beautifully updated, competitively priced, and ready for you to move right in! Don’t miss the opportunity to make this wonderful Colonial your new home. Hurry, home wont last.

132 Ridge Road, Highland Mills

$679,000

4 Beds ⋅ 4 Baths ⋅ 1046418 MLS

Custom-built by renowned builder Lou Tedaldi, this one-owner Center Hall Colonial offers nearly 3,000 sq. ft. of exceptionally crafted living space nestled on 6.2 pristine, park-like acres. Set on an exclusive private road shared by only 9 homes, this sanctuary delivers total privacy and tranquility while remaining in the highly sought after Monroe-Woodbury School District and close to all local amenities, major routes, and shopping. Inside, beautiful hardwood floors, custom crown and chair rail moldings, and oversized windows with screens bring continuous natural light throughout. The main level features a welcoming foyer with two coat closets, a formal living room with a cozy brick fireplace, and a family room also featuring its own brick fireplace. The gourmet eat-in kitchen boasts granite countertops, a double electric oven, abundant cabinet space, surplus counters, and Tiffany-style lighting, opening via sliders directly onto the back deck. Enjoy formal meals in the dining room, which features sliders out to a spacious, light-filled screened back porch with ceiling fan, perfect for effortless outdoor entertaining. A major highlight of the main level is a versatile 16x24 bonus addition featuring custom woodworking, a beamed ceiling, a bay window, and an ADA-accessible level including a full bathroom, ideal for a luxurious main floor primary suite, guest wing, or private office. Main floor laundry and a half bath add extra convenience. Upstairs, discover four generously sized bedrooms, including an expansive primary suite with hardwood flooring, a spacious walk-in closet, and an en-suite full bath with double vanity. The second bedroom is exceptionally large, easily serving as an alternate primary, while the remaining bedrooms offer ample closet space and bright, oversized windows.The property continues to impress with incredible functional spaces: Two Basements: Main walk-out basement with shelving, a dedicated workshop area, and a sound-proof room (perfect for a media room or studio). Plus a second insulated basement under the addition with separate exterior access. Property Grounds: Stone-faced concrete foundation, iconic Hudson Valley stone walls, manicured lawn, mature landscaping, storage shed, and surrounding private woods. Modern Comforts & Accessibility: ADA-accessible 2-car garage with ramp entry, full-house propane automatic generator, whole-house alarm system, 4-zone oil heating, attic fan, and 30-year shingle roof. An extraordinary property combining top-tier craftsmanship, flexible living spaces, and unmatched outdoor beauty!

5 Red Fox Run, Chester

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