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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
$799,000
5 Beds ⋅ 4 Baths ⋅ 1045151 MLS
Welcome to this beautiful and spacious 5-bedroom, 4-bathroom home, offering 2,700+ square feet of living space and plenty of room to live, work, and entertain. Set in a desirable Monroe location, this home combines generous living spaces with the comfort and functionality today's buyers are looking for. Step inside to a warm and inviting interior featuring spacious rooms, abundant natural light, and a layout designed for both everyday living and entertaining. The generously sized bedrooms provide flexibility for a growing household, guests, a home office, or additional living space. The home's multiple bathrooms add convenience, while the expansive living areas provide plenty of opportunity to create spaces tailored to your lifestyle. Whether you're hosting family gatherings or enjoying a quiet evening at home, there is room for everyone. The outdoor space is equally impressive, featuring a breathtaking views of bear mount, beautiful paver fire pit area, perfect for relaxing evenings, entertaining friends and family, and enjoying the outdoors. A two-car garage provides convenient parking and additional storage, while the extended driveway offers ample space for recreational sports or entertaining. Conveniently located in Monroe, this home offers easy access to shopping, dining, parks, schools, major roadways, and everything the surrounding area has to offer.

165 Hilltop Road, Monroe
$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
$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
$599,999
3 Beds ⋅ 3 Baths ⋅ 1043705 MLS
Welcome to 23 Alden Road in Monroe! This 3-bedroom, 2.5-bath Raised Ranch offers 1,832 square feet of living space, a versatile layout, and the added bonus of an additional 50' x 125' parcel included with the sale, the taxes and the acreage on the listing reflects the total amount with the additional parcel. The main level features comfortable living spaces with hardwood flooring beneath the existing carpeting, offering an opportunity to uncover and showcase the home's original character. Downstairs, the finished lower level provides valuable additional living space complete with a fireplace and sliding doors leading directly to the patio and fenced backyard—ideal for entertaining, recreation, a home office, or flexible everyday living. A two-car garage, crawl-space attic, under-stair storage, deck, and additional shed located on the extra parcel provide plenty of options for storage and outdoor use. Enjoy convenient access to everything Monroe has to offer, with Round Lake and Walton Lake approximately one mile away for fishing, kayaking, and boating, and Harriman State Park less than 20 minutes away for hiking and outdoor recreation. Groceries, dining, shopping, and everyday amenities are also less than a mile away, while Woodbury Common Premium Outlets is approximately 20 minutes from the home. Commuters will appreciate convenient access to the Monroe Park & Ride, a nearby train station, and major highways. With its flexible living space, fenced yard, additional parcel, and convenient location, 23 Alden Road offers plenty of possibilities for its next chapter.

23 Alden Road, Monroe
$562,500
4 Beds ⋅ 3 Baths ⋅ 1041335 MLS
Welcome to 41 Forestdale Avenue, Monroe, NY, a spacious 4-bedroom, 2.5-bath Raised Ranch in the Monroe-Woodbury School District. Tucked away on a quiet cul-de-sac in the desirable Maple Knolls neighborhood, this inviting home offers approximately 1,868 sq ft of living space on a private 0.61-acre property. Sidewalk-lined streets invite you to enjoy a bike ride, walk the dog, take a jog, or simply get outside and enjoy the neighborhood. The main level features hardwood floors and a spacious living room with soaring cathedral ceilings, creating an open and airy feel. The living room flows seamlessly into the dining area and NEW eat-in kitchen '21, beautifully updated with new cabinetry, a gorgeous backsplash, and dazzling quartz countertops. Stylish and functional, the kitchen offers a fresh, modern setting for everyday meals and entertaining. One of the home's standout features is the generous 15' x 20' screened-in porch/sunroom, providing approximately 300 sq ft of additional seasonal space to enjoy the outdoors while sheltered from the elements. Step outside onto the expansive deck overlooking the peaceful, tree-lined backyard—perfect for outdoor dining, entertaining, gardening, or simply relaxing. The finished lower level adds valuable living space with a comfortable family room offering flexibility for recreation, a home office, fitness area, or movie nights. Major recent improvements add even more value, including a NEW furnace, NEW hot water heater, and NEW driveway. Additional highlights include an attached 2-car garage, natural gas heat, public water, and public sewer. New Roof October 2026. Enjoy a prime Hudson Valley location with convenient access to NYC-bound bus and rail transportation, the New York State Thruway (I-87), and the Palisades Interstate Parkway. Nearby destinations include West Point and the United States Military Academy, Woodbury Common Premium Outlets, the Appalachian Trail, Harriman State Park, as well as shopping, dining, parks, and recreation. If you've been searching for a 4-bedroom home for sale in Monroe, NY, with a beautiful new kitchen, major recent improvements, soaring cathedral ceilings, a 2-car garage, finished lower level, 15' x 20' screened-in porch/sunroom, expansive deck, private backyard, and convenient access to transportation and all that the Hudson Valley has to offer, 41 Forestdale Avenue is one you won't want to miss.

41 Forestdale Avenue, Monroe
$565,000
3 Beds ⋅ 3 Baths ⋅ 1040813 MLS
This is the one you’ve been waiting for! Tucked away on a quiet, tree-lined street, this inviting raised ranch offers the perfect blend of comfort, space, and outdoor living. Enjoy nearby lake access to Walton Lake, where you can spend summer days boating and swimming. Inside, an open floor plan creates an ideal setting for entertaining and everyday living. The spacious living and dining areas flow seamlessly into a charming three-season room, which opens to a large deck; perfect for summer barbecues and relaxing while overlooking the private backyard. The spacious great room features a cozy fireplace, creating the perfect gathering spot. And when it’s time to enjoy the outdoors, Mombasha Park is just a half-mile away, offering walking trails, pickleball courts, a playground, and soccer and baseball fields. Conveniently located just minutes from shopping and major commuter routes, this home offers the lifestyle you’ve been looking for; peaceful surroundings, recreation, and convenience all in one!

30 Laura Road, Monroe
$589,999
4 Beds ⋅ 2 Baths ⋅ 1037720 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. Enjoy local access to the John P. Burk Memorial Pool, Earl Resevoir and Brickley Field as well for all your athletic enjoyment. 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 ⋅ 1036585 MLS
Welcome home to this charming 3-bedroom, 1.5-bath bilevel nestled in Monroe! From the moment you walk in, you’ll appreciate the warmth and comfort this home has to offer. The beautifully upgraded kitchen, complete with granite countertops, is the perfect place to gather, cook, and make memories, with a deck just off the kitchen that’s ideal for morning coffee, outdoor dining, or entertaining. Hardwood floors add warmth and character throughout the home, while the updated bathrooms bring a fresh, modern touch. Recent improvements include brand-new central air, a new hot water heater, and recently updated siding and garage doors, offering both comfort and peace of mind. The lower level features an additional versatile room that can easily be used as a home office, gym, playroom, or whatever best fits your lifestyle. Outside, you’ll find a spacious yard with plenty of room to relax, play, garden, or enjoy time with family and friends. With three bedrooms, a functional layout, inviting outdoor space, and plenty of room to make your own, this home is ready for its next chapter. Come see for yourself, you may just fall in love!

111 Hilltop Road, Monroe
$550,000
4 Beds ⋅ 3 Baths ⋅ 1035897 MLS
Welcome to 12 Veteran Circle! This spacious home features 8 well-appointed rooms and 2.5 contemporary bathrooms, offering plenty of space and comfort for your needs. The property is in nice condition, providing a move-in-ready experience. Located in a desirable area, this home combines convenience with a great neighborhood setting—perfect for anyone seeking a quality living environment. Call today to schedule your showing!

12 Veteran Circle, Monroe
$550,000
4 Beds ⋅ 2 Baths ⋅ 1033662 MLS
Amazing opportunity in the Village of Monroe's Pine Tree neighborhood! Beautifully maintained and thoughtfully updated, this spacious bi-level feature's 4 spacious bedrooms in the Monroe-Woodbury School District, offering a wonderful combination of comfort, convenience and privacy in a great commuter location close to schools, shopping and everyday amenities. The bright main level features hardwood floors throughout, a spacious living room with a beautiful bay window, and a nicely updated kitchen with granite countertops, stainless steel appliances, laminate flooring and a center island with seating for three. Many of the kitchen updates were completed four years ago, and the newer refrigerator adds another recent improvement. The three bar stools at the island can remain with the home. The primary bedroom and two additional generously sized bedrooms feature brand new carpeting, and the main-level full bath has been updated. Central air keeps the home comfortable, and the system has been professionally serviced annually. The lower level adds even more living space with laminate flooring, a fourth spacious bedroom, a second bath, fireplace, laundry area with washer and dryer included, and access to the attached two-car garage with remote opener. The lower level also has its own heat zone for added comfort and efficiency. A second refrigerator can also remain. The interior has been freshly painted, the electrical has been updated, and the home features baseboard heat, a gas boiler installed in approximately 2010 and a hot water heater approximately five years young. Step outside and discover one of this home's greatest features—a beautiful, level backyard just shy of half an acre, surrounded by mature trees and filled with nature. The private setting creates the perfect backyard retreat, whether you're relaxing on the deck, entertaining, gardening, playing or simply enjoying the peaceful surroundings. The driveway has also been redone, and the home features an updated, energy-efficient front door. Municipal water, sewer and natural gas make the transition to a more peaceful country setting easy and convenient, while still enjoying the benefits of Village living. Enjoy the added lifestyle of a private lake community for an HOA fee of just $250 for the entire year, offering lake access, a playground and volleyball area. Bring your kayak, paddleboard or non-motorized boat and make the most of warm-weather days right in your own community. This lovingly cared-for home offers space, valuable updates, a private yard, lake amenities and an excellent Monroe neighborhood setting.

5 McGarrah Road, Monroe
$425,000
3 Beds ⋅ 2 Baths ⋅ 1031523 MLS
Welcome to 23 Pike Court. Unlock the potential of this spacious 3-bedroom, 2-bath raised ranch, which offers 2,460 square feet of living space on a generous .75 acre lot, giving you the space and flexibility to create something truly special. Perfect for an investor, contractor, or DIY enthusiast, this home is ready for someone with vision. While it needs work, it is move-in ready and offers an excellent opportunity to renovate, customize, and add value in a desirable location. With its generous footprint, versatile layout, and large lot, this home is full of possibilities. Bring your ideas and transform this property into a standout home with lasting appeal.

23 Pike Court, Monroe
$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
$545,000
3 Beds ⋅ 3 Baths ⋅ 1018371 MLS
This Chester raised ranch checks every box: bright, spacious living areas, a stainless steel kitchen, and a finished basement ready for a home office, gym, or guest space. Smart-home upgrades — Nest thermostat, Ring security with window sensors, reverse osmosis filtration — add everyday ease, while the primary boiler plus central HVAC keeps you comfortable in every season. Out back: a deck, above-ground pool, and new white vinyl privacy fence for total backyard privacy. Just 12 minutes to Woodbury Common Outlets with easy highway access. 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
$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.