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$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
$599,000
4 Beds ⋅ 3 Baths ⋅ 1043948 MLS
Welcome to 20 Amy Todt Drive, a spacious and beautifully maintained raised ranch-style home offering an ideal blend of comfort, functionality, and community living. With approximately 2,100 square feet of living space, this home features the convenience 4 bedrooms including a spacious primary suite with a private full bath and walk in closet with custom shelving The main level offers an inviting flow with hardwood floors, a large living room, formal dining room, and an updated kitchen featuring granite countertops and stainless steel appliances. Step outside to the screened-in rear deck — the perfect spot to enjoy your morning coffee, relax, or entertain while taking in the peaceful surroundings. The lower level adds even more flexible living space, including a comfortable family room/den, half bath, laundry room and storage spaces with convenient walk-out access. Flexible bonus room can be used as a workshop or hobby room. A two-car garage provides ample parking and storage. Located in a desirable lake community, residents enjoy access to the lake, beach, and playground, creating a wonderful setting for recreation and everyday enjoyment. Conveniently located near commuter routes, shopping, dining, and local amenities, this home offers both the tranquility of a residential community and easy access to everything Monroe has to offer. A spacious home, a desirable location, and a lake-community lifestyle — welcome home!

20 Amy Todt Drive, Monroe
$625,000
4 Beds ⋅ 2 Baths ⋅ 1028745 MLS
Welcome to 132 Hilltop Rd, a captivating 4-bedroom, 2-bathroom home that blends comfort, character, and everyday convenience into one inviting package. The kitchen will "wow" you with oak cabinets, granite tops, a Sub-Zero refrigerator, wine refrigerator, and two sinks, all set within an open floorplan anchored by a peninsula bar area. It flows naturally into the dining room, where stylish spotlights set an elegant tone for everyday meals or special occasions. Step outside and discover a backyard built for making memories. The sparkling pool takes center stage, offering the perfect escape on warm summer afternoons, and it's fully fenced off from the rest of the yard for added peace of mind. There's also a separate play area for the kids, tucked away from the pool so everyone can enjoy the outdoors safely. Beyond that, the surrounding space invites lively gatherings, quiet morning coffees, and everything in between. Inside, four generously sized bedrooms provide restful havens for family and guests alike, each fitted with ceiling lighting for everyday comfort. The master bedroom goes a step further with custom-built shelving, adding style along with smart, built-in storage. Two well-appointed bathrooms complete the interior comforts. Homes that offer this rare combination of indoor comfort, outdoor enjoyment, and prime location don't stay on the market long. With its standout pool, versatile basement complete with a patio door walkout, and welcoming atmosphere, 132 Hilltop Rd is more than a house—it's the place you'll be proud to call home. Schedule your private showing today!

132 Hilltop Road, Monroe
$515,000
3 Beds ⋅ 2 Baths ⋅ 1037241 MLS
Welcome to the town of Chester New York! Step inside to hardwood floors and a welcoming eat-in kitchen featuring stainless steel appliances, ceramic tile flooring and soft-close cabinetry and drawers. Both full bathrooms have been beautifully updated with newer showers, tile and fixtures, plus the everyday luxury of HEATED FLOORS. Includes the rights to use Walton Lake Park. The major improvements are already done: 200-amp electrical service (2025), rear property-line fencing (2025), LG front-load washer & dryer (2025), central air (2023), roof (2022), deck (2022) and generator with updated motherboard (2021). All that, plus the home has municipal water and sewer. Outside, enjoy a property made for relaxing and entertaining. Unwind on the deck or spend a quiet afternoon surrounded by greenery and ornamental plantings, including Rose of Sharon, doublefile viburnum, arborvitae . When the seasons change, come inside and cozy up by the fireplace with its Jotul insert—the perfect spot for a chilly Hudson Valley evening. And then there’s the location! Walton Lake is just down the road, offering fishing, boating and swimming close to home. Enjoy convenient access to shopping and popular outlets, local wineries, and bus transportation to NYC. Move in, unpack and start enjoying everything this home and the Hudson Valley have to offer. The updates are done—the only thing missing is you.

74 Heaton Road, Monroe
$605,000
3 Beds ⋅ 2 Baths ⋅ 1035387 MLS
Imagine coming home to your own private retreat, nestled on over 2 beautiful acres in the heart of the Hudson Valley. This stunning home offers the perfect blend of comfort, style, and tranquility, creating an oasis both inside and out. Step inside to a sun-drenched living room featuring soaring cathedral ceilings and a dramatic wall of windows that fills the space with natural light. The spacious dining area flows seamlessly into the heart of the home, a beautifully renovated kitchen designed to impress. Showcasing crisp white cabinetry, quartz countertops, a large farmhouse sink, stainless steel appliances, behind barn doors a large pantry and a stunning center island, this kitchen is perfect for both everyday living and entertaining. Enjoy casual meals in the bright breakfast area, which opens to a generously sized deck overlooking the peaceful backyard an ideal setting for morning coffee, outdoor dining, or simply relaxing in nature. Gleaming hardwood floors and recessed lighting add warmth and elegance throughout the main level. The spacious primary suite offers cathedral ceilings, two large closets, and plenty of room for a king-sized bed. Two additional generously sized bedrooms and a full bathroom complete the main level. Downstairs, you'll find a welcoming tiled family room with direct access to the porch and backyard, making indoor-outdoor living effortless. A versatile bonus room provides endless possibilities as a home office, gym, playroom, or guest space. The lower level also features a newly renovated full bathroom and a private laundry room. Outside, the expansive property is a true sanctuary, complete with an above-ground pool, playground, and plenty of open space to enjoy recreation, gardening, or peaceful evenings under the stars. Conveniently located for commuters and just minutes from the Hudson Valley's renowned wineries, breweries, restaurants, shopping, and outdoor recreation, this exceptional home offers the lifestyle you've been searching for. Come experience all the beauty and charm the Hudson Valley has to offer you'll be ready to call this one home.

412 Laroe Road, Chester
$549,000
3 Beds ⋅ 2 Baths ⋅ 965720 MLS
43 Sunset Terrace | Highland Mills, NY. Offered for the first time in 58 years, this thoughtfully maintained 3-bedroom, 2-bath home sits atop a quiet neighborhood with beautiful mountain views. Carefully cared for through the decades, it offers a special opportunity for a new owner to bring their own style while benefiting from the stewardship and improvements already in place. Natural light fills the main living spaces, where hardwood floors run throughout the main level and expansive windows frame the surrounding landscape. Recent owner updates include the roof, windows, gutters, and generator. Just off the kitchen, a beautiful bluestone patio creates an extension of the living space, ideal for outdoor dining and entertaining. An oversized detached two-car garage is exceptional for vehicles, storage, hobbies, workshop space, or recreational equipment. The lower level expands the home's versatility with two large living rooms, one featuring a wood-burning fireplace. An additional room with a closet and a full bathroom on this level provides flexible space for guests, a home office, a fitness area, or creative pursuits. An oversized mudroom and laundry area with abundant storage adds everyday practicality and helps keep the main living areas organized. Located in the Town of Woodbury and within the Monroe-Woodbury School District, residents also enjoy access to exclusive town amenities, including the John P. Burke Memorial Pool and Earl Reservoir. The property also offers exceptional access to the best of Hudson Valley living, with nearby hiking trails, outdoor recreation, and cultural destinations, including Storm King Art Center. Conveniently located approximately five miles from rail service to New York City, about 51 miles from Midtown Manhattan, seven miles from Storm King Art Center, and six miles from Schunnemunk State Park, the home offers a wonderful balance of natural beauty and commuter accessibility. Additional features include transferable leased solar panels. With its elevated setting, mountain views, flexible living spaces, access to Woodbury's exceptional recreational amenities, and location within the Monroe-Woodbury School District, 43 Sunset Terrace offers a special opportunity to create a home that balances comfort, community, and Hudson Valley living.

43 Sunset Terrace, Highland Mills
$625,000
3 Beds ⋅ 3 Baths ⋅ 968339 MLS
Beautifully updated oversized high ranch in a cul-de-sac, with generously sized rooms, sitting on great flat almost 1/2 acre of property with an updated pool and fenced private backyard. Light and bright with new recessed lighting throughout the house, the renovated kitchen has all new appliances, cabinets, countertops and tile flooring and the primary bedroom has walk-in closet and ensuite bathroom. Pretty hardwood floors throughout the living areas on the first floor and all the big bedrooms have new laminate flooring. The backyard has a big screened in deck and a brand new deck around the pool with a new liner and pump/filter. Downstairs you will find three more rooms that can be used as a den/family room, office, playroom or whatever your heart desires and the laundry room. Plenty of parking and a one car garage. Great commuter location and walking distance to restaurants, deli and other local shops. Close to major highways, schools, Woodbury Common outlets and many other shopping areas and join the Woodbury parks and recreation and town pool!

41 Rutledge Avenue, Highland Mills

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.