Chester Homes with Monroe-Woodbury School district

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

$650,000

3 Beds ⋅ 4 Baths ⋅ 1027353 MLS

Welcome to a contemporary retreat where refined design, exceptional craftsmanship, and a seamless connection to nature come together in one of Chester’s most desirable settings. Thoughtfully designed for both everyday living and effortless entertaining, this light-filled residence offers three bedrooms, two full bathrooms, and two half baths with an open, flowing floor plan that balances sophistication with comfort. The main level is defined by soaring ceilings, expansive windows, and an abundance of natural light that fills every corner of the home. The dramatic living room serves as the heart of the residence, centered around a wood-burning fireplace and overlooking a beautifully landscaped backyard complete with a custom-built pond and tranquil gardens that create a truly peaceful backdrop. The custom-designed white kitchen is a true showpiece, crafted for those who love to entertain. A large center island with an integrated cooktop allows the chef to remain part of every conversation, while generous workspace, custom cabinetry, and views of the surrounding landscape make the space as functional as it is beautiful. Sliding doors extend the living space to a private patio, creating a natural indoor-outdoor flow for dining and gatherings. Upstairs, the spacious primary suite and additional bedrooms are thoughtfully appointed with custom-built closet systems that maximize both style and organization. Three generously sized bedrooms and two beautifully finished full bathrooms provide comfortable accommodations designed for modern living. The finished lower level offers exceptional flexibility, featuring a spacious recreation or living area, a convenient half bath, and a dedicated storage room—ideal for a media room, home office, gym, guest retreat, or extended living space. Perfectly positioned just minutes from Walton Lake, Goosepond Mountain State Park, and the world-class shopping and dining of Woodbury Common Premium Outlets, this home offers the best of Hudson Valley living with convenient access to New York City in approximately 90 minutes. Combining contemporary architecture, designer finishes, and an idyllic natural setting, this exceptional residence delivers a lifestyle defined by comfort, elegance, and effortless luxury.

29 Murray Drive, Chester

$389,000

3 Beds ⋅ 1 Baths ⋅ 1019170 MLS

Welcome to 185 Oxford Road, Chester! •••••This charming 3-bedroom Ranch home is now available for $389,000. Offering 1,062 sqft of comfortable one-level living on a generous 0.95-acre lot in the Monroe-Woodbury School District, this 1952-built home has been freshly painted and is move-in ready. •••••The interior features an open floorplan with beautiful knotted hardwood flooring, cathedral ceiling, natural woodwork, recessed lighting, and a welcoming breakfast bar in the open kitchen. The kitchen is equipped with a cooktop, oven, refrigerator, washer, and dryer (with both electric and gas dryer hookups right in the kitchen). You'll also appreciate the bow window, casement and double-pane windows that fill the home with loads of natural light. •••••The unfinished basement provides plenty of storage, conveniently accessed using Bilco doors. Outside, the level, landscaped lot offers front and backyard space and is partly wooded for privacy. •••••Highlights include: • Brand New Boiler • Brand New Gravel Driveway • Entire House Painted and Refreshed • Central Air plus Ductless Cooling in the Living Room • Propane hot water baseboard heating system • 2 Drilled Wells • Septic system (pumped every 4 years) • 100-amp electric service •••••Located in the highly rated Monroe-Woodbury School District, this home has annual taxes of $6,831 (after STAR discount for primary home-owners). •••••This affordable, single-level Ranch home combines classic appeal with modern improvements and a spacious lot — ideal for comfortable living with room to enjoy the outdoors. •••••Discover the Perfect Blend of Peaceful Country Living and Modern Convenience •••••Escape to this serene rural retreat that offers the best of both worlds: a tranquil, private country setting paired with unmatched accessibility. Nestled in a quiet, picturesque location, this home provides a true sense of peace and privacy while placing everyday essentials and major transportation routes just minutes away. •••••A Paradise for Outdoor Enthusiasts This property is an outdoor lover’s dream. Step outside and immerse yourself in abundant recreational opportunities, with excellent hiking, cycling, and rollerblading right at your doorstep. World-class natural destinations surround you, including Goosepond Mountain State Park, Harriman State Park, and Bear Mountain State Park — all offering miles of scenic trails, stunning lakes, and breathtaking vistas. •••••Just minutes away, the renowned Heritage Trail awaits — a beautifully paved 19.5-mile multi-use path along the historic Erie Railroad corridor, stretching from Middletown to Harriman. Whether you enjoy walking, running, cycling, or rollerblading, this scenic trail delivers peaceful countryside views and year-round enjoyment. •••••Effortless Commuting & Everyday Convenience Commuters will love the easy access to major routes: • Less than 3 miles to Route 17 (The Quickway) • Just 4 miles to the Monroe Park & Ride at Twin Lakes • Approximately 8 miles to the New York State Thruway (I-87) • About 10 miles to the Harriman Metro-North train station •••••Whether heading into the Hudson Valley or New York City, commuting is seamless and efficient. Shopping, dining, top-rated schools, healthcare, and all modern amenities are conveniently close, allowing you to enjoy a relaxed rural lifestyle without ever feeling isolated. •••••This rare combination of peaceful country charm, endless outdoor adventures, and superior location makes this home an exceptional opportunity for those seeking tranquility without compromise. Welcome home to your perfect sanctuary. •••••Reach out for a private showing today and discover all that 185 Oxford Road, Chester has to offer !!

185 Oxford Road, Chester

$575,000

3 Beds ⋅ 3 Baths ⋅ 1018371 MLS

Welcome to this beautifully maintained raised ranch, perfectly situated on a desirable corner lot in Chester. This inviting 3-bedroom, 2 full and 1 half bath home blends comfort, style, and modern convenience in a location you'll love. Filled with natural light, the home features spacious living areas and a well-appointed kitchen with stainless steel appliances. The finished basement offers flexible space for a family room, home office, gym, or guest retreat. Thoughtful upgrades, including a Nest thermostat, Ring security camera with window sensors, and a reverse osmosis water filtration system, enhance both comfort and convenience. In addition to the home's primary boiler heating system, the central HVAC system provides air conditioning and electric auxiliary heat, offering added comfort and flexibility throughout the seasons. Step outside to your own private backyard oasis featuring a spacious deck, above-ground pool, and newly installed white vinyl privacy fence—perfect for relaxing or entertaining. Conveniently located just 12 minutes from Woodbury Common Premium Outlets with easy access to major highways, 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

$800,000

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

$1,200,000

4 Beds ⋅ 3 Baths ⋅ 1010784 MLS

This stunning 4 bedroom, 3 bathroom home with a beautifully updated kitchen is the perfect place to call home. With plenty of space to entertain and relax, you'll love the open layout and modern amenities that this home has to offer. Whether you're enjoying a meal in the spacious kitchen or unwinding in the cozy living room, you'll feel right at home in this charming and inviting space.

63 Whitetail Run, Chester

$949,000

4 Beds ⋅ 3 Baths ⋅ 1007687 MLS

Set on 2.3 acres in Chester, this impressive property offers space, versatility, and scenic surroundings. The residence features approximately 3,332 square feet of living space with 4 bedrooms, 2 full baths and 1 half bath, thoughtfully designed for comfortable everyday living and entertaining. Interior highlights include generously sized living areas, a fireplace, abundant natural light, and flexible spaces suited for a variety of needs. Outside, the property offers exceptional utility and open space with garage/workshop space, fenced areas, and room for equipment, hobbies, recreation, or agricultural use (buyer to verify permitted uses). Enjoy peaceful views, outdoor living areas, and the privacy of a substantial parcel while remaining within convenient reach of local shops, commuter routes, and area amenities. A rare opportunity to own a property with space, functionality, and endless potential

19 Bull Mine Road, Chester

$675,000

4 Beds ⋅ 3 Baths ⋅ 1009848 MLS

Set on 3.2 acres within the Monroe-Woodbury School District, 335 Laroe Road offers a rare combination of space, functionality, and a convenient Chester location. Step inside to the welcoming two-story foyer featuring an open staircase and you'll immediately appreciate the size of the home. The main level offers a functional layout with multiple living spaces, including a living room, formal dining room, and family room anchored by a floor-to-ceiling stone fireplace. Large windows throughout the main level bring in an abundance of natural light, creating a bright and open feel throughout the home. The eat-in kitchen is designed for both everyday use and entertaining, offering generous cabinet and counter space, a center island, and an open layout that connects well with the rest of the home. French doors lead directly from the kitchen to the rear deck, which was updated within the last two years and provides plenty of room to enjoy the outdoor setting. The first floor also features a large pantry and laundry area with an impressive amount of cabinetry and storage, along with a full bathroom for added convenience. Upstairs, you'll find four bedrooms and two full bathrooms, including a spacious primary suite. The basement offers an incredible amount of additional space and storage that truly needs to be seen in person to be appreciated. Throughout the home, there is no shortage of storage or usable living space. Outside, the property provides a mix of open yard and mature trees across 3.2 acres, offering plenty of room to enjoy the outdoors. An existing in-ground pool is also located on the property and is being sold as-is. Located right next door, the Orange County Recreation Area at Laroe Road features walking and hiking trails, picnic areas, fishing ponds, and additional green space for all to enjoy. Call today to schedule your private showing. **Home is being sold AS-IS**

335 Laroe Road, Chester

$999,900

1003998 MLS

INCREDIBLE PROPERTY!!! MUNICIPAL WATER!!! MONROE WOODBURY SCHOOL DISTRICT!!! Welcome to 206 Greycourt Road, Chester, NY A truly rare and remarkable offering in the heart of Orange County, Presenting an extraordinary opportunity to acquire a standout property with exceptional visibility, flexible “ OP” zoning, multiple structures, and limitless potential. Positioned on one of Chester's most highly visible corridors with easy access to Route 17, this distinctive property combines historic character, income potential, and future development possibilities in one compelling package. Situated within the Town of Chester's “OP” Zoning District, the property offers a level of flexibility seldom found in today's market. Whether your vision includes professional offices, hospitality related uses, boutique commercial ventures, residential income production, event oriented concepts, or a mixed-use redevelopment, the foundation is already in place for something truly special. At the heart of the property stands a magnificent Victorian residence, thoughtfully expanded in 1850 from the original home dating back to 1790, which now serves as the garage. Rich in history, architectural character, and timeless craftsmanship, this remarkable structure offers a rare glimpse into the region's past while providing an inspiring setting for the future. A classic rocking chair front porch sets a welcoming tone, inviting guests to slow down and appreciate the property's timeless charm. Beyond the front door, a grand foyer unfolds into an elegant formal living room that transitions effortlessly into a spacious family room, where soaring ceilings, original hardwood floors, and beautifully preserved period details create an atmosphere of warmth, character, and enduring sophistication. A formal dining room, beautiful kitchen, and convenient first-floor powder room complete the main level. Ascending the impressive staircase, the second floor offers four spacious bedrooms, an additional sitting room that could easily function as a fifth bedroom or office, a large full bathroom, and a dedicated laundry room. Above, a substantial walk-up attic provides exceptional storage or future expansion opportunities. Complementing the main residence is a second detached home featuring two bedrooms and one full bathroom, ideal for rental income (currently rented), caretaker accommodations, employee housing, or additional business flexibility. Two substantial barn structures further elevate the property's possibilities. One stands proudly as a striking architectural centerpiece ready for adaptive reuse, while the second offers the opportunity to restore and reimagine a piece of the property's rich history. Together, these structures provide endless potential for creative redevelopment, storage, workshops, event space, or specialty commercial applications. Infrastructure is equally impressive, with public water service and three separate water meters already in place, providing flexibility for multiple users or future configurations. Location remains one of the property's strongest assets. With unparalleled visibility, easy access to Route 17, and close proximity to the Villages of Chester, Goshen, and Monroe, this property is positioned at the crossroads of commerce, convenience, and growth. Nearby amenities include The Heritage Trail, award winning shopping, renowned local restaurants, farm markets, recreational destinations, and the highly sought after Monroe Woodbury School District. Properties of this caliber, character, and versatility are rarely available. Whether you're seeking a trophy investment, a headquarters location, an income producing asset, or the canvas for your next transformative project, 206 Greycourt Road offers an opportunity limited only by imagination. Additional property across the street also be available for the right buyer. Schedule your private tour today and discover the extraordinary potential of one of Chester's most captivating properties.

206 Greycourt Road, Chester

$999,900

1004000 MLS

INCREDIBLE PROPERTY!!! MUNICIPAL WATER!!! MONROE WOODBURY SCHOOL DISTRICT!!! Welcome to 206 Greycourt Road, Chester, NY A truly rare and remarkable offering in the heart of Orange County, Presenting an extraordinary opportunity to acquire a standout property with exceptional visibility, flexible “ OP” zoning, multiple structures, and limitless potential. Positioned on one of Chester's most highly visible corridors with easy access to Route 17, this distinctive property combines historic character, income potential, and future development possibilities in one compelling package. Situated within the Town of Chester's “OP” Zoning District, the property offers a level of flexibility seldom found in today's market. Whether your vision includes professional offices, hospitality related uses, boutique commercial ventures, residential income production, event oriented concepts, or a mixed-use redevelopment, the foundation is already in place for something truly special. At the heart of the property stands a magnificent Victorian residence, thoughtfully expanded in 1850 from the original home dating back to 1790, which now serves as the garage. Rich in history, architectural character, and timeless craftsmanship, this remarkable structure offers a rare glimpse into the region's past while providing an inspiring setting for the future. A classic rocking chair front porch sets a welcoming tone, inviting guests to slow down and appreciate the property's timeless charm. Beyond the front door, a grand foyer unfolds into an elegant formal living room that transitions effortlessly into a spacious family room, where soaring ceilings, original hardwood floors, and beautifully preserved period details create an atmosphere of warmth, character, and enduring sophistication. A formal dining room, beautiful kitchen, and convenient first-floor powder room complete the main level. Ascending the impressive staircase, the second floor offers four spacious bedrooms, an additional sitting room that could easily function as a fifth bedroom or office, a large full bathroom, and a dedicated laundry room. Above, a substantial walk-up attic provides exceptional storage or future expansion opportunities. Complementing the main residence is a second detached home featuring two bedrooms and one full bathroom, ideal for rental income (currently rented), caretaker accommodations, employee housing, or additional business flexibility. Two substantial barn structures further elevate the property's possibilities. One stands proudly as a striking architectural centerpiece ready for adaptive reuse, while the second offers the opportunity to restore and reimagine a piece of the property's rich history. Together, these structures provide endless potential for creative redevelopment, storage, workshops, event space, or specialty commercial applications. Infrastructure is equally impressive, with public water service and three separate water meters already in place, providing flexibility for multiple users or future configurations. Location remains one of the property's strongest assets. With unparalleled visibility, easy access to Route 17, and close proximity to the Villages of Chester, Goshen, and Monroe, this property is positioned at the crossroads of commerce, convenience, and growth. Nearby amenities include The Heritage Trail, award winning shopping, renowned local restaurants, farm markets, recreational destinations, and the highly sought after Monroe Woodbury School District. Properties of this caliber, character, and versatility are rarely available. Whether you're seeking a trophy investment, a headquarters location, an income producing asset, or the canvas for your next transformative project, 206 Greycourt Road offers an opportunity limited only by imagination. Additional property across the street also be available for the right buyer. Schedule your private tour today and discover the extraordinary potential of one of Chester's most captivating properties.

206 Greycourt Road, Chester

$529,000

3 Beds ⋅ 3 Baths ⋅ 898870 MLS

Some lots just have good bones. This one has it's own private nature trail, stocked pond rights, and a cul-de-sac that dead-ends into miles of nature trails anchored by a solid, spacious raised ranch on 1.8 acres. Inside, the home has been partially updated and offers solid bones with room to add your own touch over time. The house delivers where it counts. Three bedrooms, two and a half baths, large kitchen, a two-car garage, and a three-season room and deck that make the most of a property this beautiful. The woodburning stove in the basement helps the winter months stay cozy while saving on fuel oil bills. Multiple outbuildings including a shed and a playhouse that will get more use than you'd expect. The lawn and mature landscaping are genuinely impressive — the kind that takes years to establish and shows the moment you pull in the driveway. Then there's everything else. When not playing on the impeccable lawn, the kids could be kids catching frogs and fish, climbing trees and building forts in the woods.. All without leaving the property. When they do, the trail into Goosepond Mountain State Park is just a few doors down, at the end of the Cul de Sac.. The street itself is unhurried and unpretentious — picture dads teaching kids to ride bikes in the road, strollers, joggers, dogs on leashes and kids swarming ice cream trucks. With easy access to amenities and a realistic commute to NYC, Booth Rd means you don't have to choose between the life you want and the job that funds it. Come feel it. The land speaks for itself.

94 Booth Road, Chester

$900,000

4 Beds ⋅ 3 Baths ⋅ 1002536 MLS

Beautifully maintained Colonial set on a picturesque and private property offering the perfect blend of comfort, space, This spacious home features an inviting layout with generously sized rooms, hardwood flooring, elegant moldings, and abundant natural light throughout. The heart of the home is the oversized eat-in kitchen with granite countertops, extensive cabinetry, pantry space, and excellent flow into the warm and welcoming family room with fireplace — ideal for both entertaining and everyday living. Formal living and dining areas provide additional space for gatherings and special occasions. The second level offers a large primary suite with vaulted ceilings, walk-in closet, and spa-style bath, along with spacious additional bedrooms and ample storage throughout the home. Step outside and enjoy the beauty and privacy of the expansive property surrounded by mature trees and peaceful natural scenery. Whether relaxing on the front porch, entertaining on the deck, or simply enjoying the open outdoor space, this property offers a true retreat-like setting. A rare opportunity to own a move-in-ready Colonial offering privacy, charm, and exceptional living space.

60 Whitetail Run, Chester

Chester Homes with Monroe-Woodbury School district

Newest Chester Homes with Monroe-Woodbury School district