Chester Homes with Monroe-Woodbury School district

Welcome to Chester, New York – a charming town nestled in the heart of Orange County, where scenic landscapes meet a vibrant community spirit. Known for its picturesque views and friendly atmosphere, Chester offers a unique blend of rural charm and modern conveniences. With the majestic backdrop of the nearby mountains and serene lakes, residents enjoy a lifestyle that is both tranquil and invigorating.

Chester is not just a feast for the eyes; it is also a hub for families seeking quality education. The town is served by the highly regarded Monroe-Woodbury School District, which is renowned for its commitment to academic excellence and comprehensive extracurricular programs. Parents can take pride in knowing that their children are receiving an education that prepares them for future success, all within a supportive and nurturing environment.

Real estate in Chester is diverse, featuring everything from cozy cottages to spacious family homes, many of which boast stunning views and ample outdoor space. Whether you’re looking for a serene retreat or a family-friendly abode, Chester has something to offer everyone. The town’s close-knit community hosts various events throughout the year, fostering connections among residents and creating a sense of belonging.

With its idyllic setting, excellent schools, and welcoming atmosphere, Chester, NY, is an ideal place to call home. Come explore the charm of Chester and discover the perfect home for you and your family in this delightful corner of Orange County!

Newest Chester Homes with Monroe-Woodbury School district

$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

$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

$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

$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

$799,000

4 Beds ⋅ 3 Baths ⋅ 1034771 MLS

This well-maintained 4-bedroom, 2.5-bath home on 3 private acres is anchored by an expansive 3-tier Trex deck system and an on ground pool with 8-foot deep end, complemented by a sun deck and pool-surround walkway. The 2,516 square-foot home features 9-foot ceilings with wood molding, with hardwood floors and tile throughout the main floor. The main floor flows from a welcoming foyer through the kitchen and family room, with a separate living room and formal dining room, plus laundry and a half bath. Upstairs, four bedrooms and two full baths provide ample space. The basement offers generous storage, and the 2-car garage completes the layout with a spacious driveway for multiple vehicles. The property is move-in ready with significant recent upgrades: oil furnace replaced October 2020, central air replaced June 2022, and a whole-house filter and water softener system installed April 2024. Propane gas serves the kitchen and dryer, while the fireplace has been converted to propane for convenience but retains the option to revert to wood burning. The home features a sub-panel electric system with manual transfer switch for seamless generator backup in the event of power outages. Located in a quiet Chester cul-de-sac with mountain and woodland views, the home is perfectly positioned for both primary residence and weekend getaway living. Just steps from the Heritage Trail system for outdoor recreation, and only minutes from Legoland, shopping, dining, and all area conveniences.

3 Garnett Hill Road, Chester

$289,000

2 Beds ⋅ 1 Baths ⋅ 1030923 MLS

Looking for the perfect weekend stay, peaceful getaway, or a one-of-a-kind place to call home? Step into the timeless charm of this historic 1800s farmhouse, where character, history, and a warm, inviting setting come together. Whether you envision weekends away from the hustle and bustle, a charming country retreat, or year-round living, this unique property offers an opportunity to own a true piece of history. Original details, classic craftsmanship, and the distinctive character of a bygone era create a home unlike today’s new construction. Adding to its rich history, the original deed to the property is included and will be conveyed to the new owner—a rare keepsake that reflects the home’s remarkable past. As is typical of homes built during this period, some ceilings, doorways, and stairwells are lower than modern standards, adding to the home’s authentic historic character and charm. If you’ve been searching for a weekend escape, a peaceful retreat, or a home filled with personality and a story to tell, this special farmhouse is ready for its next chapter.

166 Bull Mill Road, Chester

$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

$449,000

3 Beds ⋅ 2 Baths ⋅ 1033721 MLS

Welcome to 66 Whitetail Run – Chester, NY. Tucked back from the road on an ample, tree-lined lot, this charming contemporary colonial offers the perfect blend of privacy and convenience in the Monroe-Woodbury school district. Surrounded by nature and filled with birdsong, this peaceful setting feels like a retreat while still being close to all local amenities. Step inside to a bright, open living room featuring soaring ceilings, a wood-burning fireplace, and oversized windows that flood the space with natural light. Hard floors flow throughout the main level, leading to a spacious eat-in kitchen with granite countertops, plus a formal dining room perfect for hosting gatherings and special occasions. This 3-bedroom, 1.5-bath home also offers both bathrooms newly renovated, along with the convenience of a main-floor laundry room with a new washer and dryer. An attached one-car garage adds everyday practicality, while the back patio invites you to unwind and enjoy the tranquil, wooded surroundings. Don't miss your opportunity to make this move-in ready home yours!

66 Whitetail Run, Chester

$799,000

4 Beds ⋅ 3 Baths ⋅ 1012284 MLS

Welcome to this beautifully charming Center Hall Colonial, privately set back from the road on a picturesque property with a tranquil man-made pond, fountain, and inviting wrap-around front porch. This spacious home offers the perfect balance of classic elegance and comfortable everyday living. The thoughtfully designed floor plan features a formal living room that flows seamlessly into the warm and inviting family room with a fireplace, creating an ideal space for entertaining. The spacious kitchen is appointed with granite countertops, a center island, abundant cabinetry, and sliders leading to an expansive deck overlooking the peaceful backyard. A formal dining room, powder room, and first-floor laundry complete the main level. Upstairs, the generous primary suite features a private ensuite bath, while three additional bedrooms share a full hall bath. A walk-up staircase leads to a full-house unfinished attic, offering outstanding potential for future living space. The finished walk-out basement provides even more room to relax or entertain, with sliders opening to a covered patio. An oversized two-car garage and a huge storage shed provide exceptional storage and convenience. Ideally located in the highly sought-after Monroe-Woodbury School District, this exceptional home combines timeless Colonial charm, abundant living space, beautiful outdoor amenities, and endless possibilities in a peaceful Chester setting.

197 Oxford Road, Chester

$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

$750,000

4 Beds ⋅ 4 Baths ⋅ 1020165 MLS

Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgettable place to call home. Inside, the heart of the home is anchored by a stunning double sided fireplace that effortlessly connects the main living areas, creating warmth, character, and an inviting atmosphere for both everyday living and entertaining. Sunlight pours into the beautiful sunroom, offering the perfect place to enjoy your morning coffee, unwind with a good book, or simply take in the tranquil views of the property throughout every season. Step outside and discover the true highlight of this remarkable property. Designed with entertaining in mind, the backyard is a private oasis featuring a sparkling inground pool, beautifully integrated outdoor living spaces, a custom built fire pit, and built in seating that invites family and friends to gather long after the sun goes down. Whether you're hosting summer pool parties, enjoying crisp fall evenings by the fire, or simply relaxing in your own backyard retreat, this outdoor space delivers an exceptional lifestyle year round. Set on over three private acres, the property offers the perfect balance of open space and privacy. There is plenty of room to explore, play, garden, or simply enjoy the serenity of nature, all while being just minutes from the conveniences of the Hudson Valley. Offering 4 bedrooms, inviting living spaces, and an outdoor setting that feels like your own private resort, this is more than just a home. It is a place where memories are made, weekends are enjoyed, and every season brings something special.

985 Craigville Road, Chester

$634,999

4 Beds ⋅ 3 Baths ⋅ 1013375 MLS

Rare opportunity in Chester! This 4-bedroom, 3-bath raised ranch sits on a private 2.5-acre lot and features a true 6-car garage — an uncommon and highly desirable feature that sets this home apart. The oversized garage offers exceptional flexibility: perfect for the car enthusiast, contractor, large family, or anyone who needs serious storage, a workshop, or space for boats, RVs, or equipment. Inside, the home offers 2,316 sq ft of comfortable living space with a practical raised-ranch layout, full basement, and room to expand or personalize. The private 2.5-acre setting provides privacy, outdoor space, and room to enjoy the Hudson Valley lifestyle while remaining convenient to major routes and amenities. Whether you’re looking for extra vehicle capacity, a home-based business space, or simply room to breathe, the 6-car garage combined with the acreage makes this a standout property in the area. Monroe-Woodbury schools. Schedule your showing today. Located in Orange County with easy access to major routes, this property delivers the space and privacy so many buyers are searching for — without sacrificing convenience. Whether you’re looking for a primary residence with room to grow or a peaceful retreat, 424 Laroe Road offers a strong foundation and exceptional land value. Key Features: 4 bedrooms | 3 bathrooms 2,316 sq ft 2.5 private acres Expansive deck for outdoor living Built 1974 – solid bones with modern potential Convenient Chester location Schedule your private showing today and experience the space, privacy, and potential for yourself.

424 Laroe Road, Chester

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