Courtesy: Curasi Realty, Inc.
845-457-9174
Welcome to 70 Main Street, a village gem situated right in the heart of historic Chester! This versatile 4-bedroom, 2.5-bathroom home combines classic architectural character with generous living spaces and modern convenience. The main residence features an inviting floor plan with bright, sunlit rooms and comfortable living areas throughout. A standout highlight of this property is the separate detached barn/garage, featuring a private loft perfect for an artist studio, or a dedicated work-from-home space. Enjoy classic Village of Chester living with walkable access to schools, local dining, boutique shopping, parks, and effortless commuter routes. A rare find offering space and charm.
Courtesy: Keller Williams Hudson Valley
845-639-0300
Welcome to this luxurious 4 bedroom duplex condo, perfectly situated in a prime location. Featuring fabulous high-end finishes, a stunning designer kitchen, beautiful views, and immaculate landscaping, this home is unlike anything you’ll see on the market today. A true dream home you’ll fall in love with the moment you walk in. P.s. There are floor plans by the images. Please be aware that this is approximate, might not be this exact unit.
Courtesy: Owner Entry.com
617-542-9300
Motivated Seller. Highly sought-after Warwick Schools, this Colonial offers curb appeal with custom stone entrance pillars featuring illuminated house numbers, an inlaid driveway address, professionally landscaped grounds accented by natural stone and in-ground lighting, and an insulated two-car carriage-style garage with glass doors. A grand two-story foyer with soaring ceilings, elegant wainscoting, and abundant natural light. The dramatic two-story living room showcases vaulted ceilings, a fireplace, and expansive windows with Sugar Loaf Mountain views. The spacious kitchen features stainless steel appliances, a center island, built-in wine cooler, and a bright eat-in dining area with access to the rear deck. Generously sized family, formal, and dining rooms provide the perfect setting for everyday living and entertaining. The primary suite offers a walk-in closet, dressing area, whirlpool soaking tub, and separate walk-in shower. Three additional spacious bedrooms, a finished basement with a bonus room ideal for a pantry, or additional storage. Minutes from wineries, farms, Woodbury Outlets, Metro-North, major highways, and more.
Seasonal Adirondack Cottage with DOCK & BEACH on LOON LAKE! Beautiful 4-bedroom, 2-bath home on picturesque Loon Lake, located in the well-established Vista View Association with just eight other homeowners. This inviting Adirondack retreat features a spacious three-season porch with panoramic lake views-perfect for morning coffee, evening cocktails, or simply taking in the peaceful surroundings. Inside, you'll find two comfortable living areas, providing plenty of space to gather with family and friends. An attic offers excellent storage along with a bonus room for additional flexibility/storage. Each cottage includes 20 feet of lake frontage with dedicated dock space, making it easy to enjoy boating, swimming, fishing, and all that Loon Lake has to offer. A great sandy beach to enjoy as well! A wonderful opportunity to own a low-maintenance seasonal getaway in the heart of the Adirondacks.
Courtesy: River Realty Services, Inc.
845-564-2800
One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space. Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk to the village!
Courtesy: MK Realty Inc
845-782-0205
Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail is thoughtfully upgraded for comfort and style. Enjoy the privacy of a modern retreat in a warm, vibrant community—the perfect setting to make new memories.
Courtesy: MK Realty Inc
845-782-0205
Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail is thoughtfully upgraded for comfort and style. Enjoy the privacy of a modern retreat in a warm, vibrant community—the perfect setting to make new memories.
Courtesy: Howard Hanna Rand Realty
845-928-9691
Move in ready townhome with a NYC bus stop within the community!! Whispering Hills in Chester is perfectly positioned for commuters being 2 miles to Route 17. Enjoy a prefect blend of comfort and convenience with a maintenance free lifestyle in this two bedroom townhome. The main floor has brand new flooring, a living room with a wood burning fireplace,and a separate dining area ideal for entertaining.The kitchen has a tile backsplash, and a natural gas range. A convenient half bath and laundry area complete the first floor. Upstairs,the primary bedroom offers vaulted ceilings,a generous walk in closet and a full bath with private access to the hallway. The second bedroom is of ample size with a double door closet. A skylight in the hallways brightens the home. Additional features and highlights include central air, natural gas heating, an attached one car garage with extra storage, building roof replaced in 2022, HVAC 2013, skylight 2013, municipal water and sewer,reasonable hoa fees, snow removal and beautifully maintained grounds. Community amenities feature a dog park, playground, two pools, a gym and more. Just 5 minutes from the heart of Chester where you'll find local shopping,dining and entertainment all while remaining 70 miles from NYC, 10 minutes to LegoLand and close to Woodbury Common, Resorts Casino and Bethel Woods Concert Venue. Visit our nearby breweries, cafes,farmer market and historic Sugarloaf Village. Come see why everyone wants to live here!
Rich in Adirondack history and surrounded by nature, Calamity Cove is a one-of-a-kind year-round retreat offering over 3 acres across two separately deeded parcels with direct boating access to beautiful Loon Lake. Originally home to a campground and later a popular local gathering place, the property has evolved into the peaceful waterfront escape it is today while preserving pieces of its remarkable past. The heart of the home--the spacious great room--features reclaimed architectural elements from the historic Watch Rock Hotel in Schroon Lake, creating an atmosphere that simply can't be replicated. Hand-hewn beams, rustic wood accents, and Adirondack craftsmanship complement this inviting 3-bedroom, 1-bath home. Two wood stoves, open living and dining areas, and a screened porch provide the perfect setting for gathering with family and friends after a day on the lake. A picturesque horseshoe driveway framed by stone pillars welcomes you to the property, where mature pines and hardwoods create a peaceful, private setting. Enjoy level access to your private Loon Lake frontage, making it easy to launch a kayak, hop on the boat, fish, or simply relax while taking in the sights and sounds of the Adirondacks. A large detached storage building offers plenty of room for boats, kayaks, snowmobiles, ATVs, tools, and all your outdoor gear. The second parcel provides exceptional flexibility--maintain it as a wooded privacy buffer or explore the opportunity to build a second home or guest cottage (subject to APA and municipal approvals). Whether you're searching for a year-round residence, a four-season getaway, or a property with future potential, Calamity Cove offers a rare combination of Adirondack history, privacy, recreation, and opportunity in one unforgettable setting.
Courtesy: Howard Hanna Rand Realty
845-928-9691
This charming updated 4-bedroom beauty in the Warwick School district offers a private and quiet setting featuring an above ground pool surrounded by a freshly painted deck just 3 minutes from Sugar Loaf Arts and Crafts Village. Its' kitchen has been upgraded boasting stainless steel appliances, granite countertops, and cherrywood cabinetry with undermount lighting and a wine/ beverage cooler. Hardwood floors can be found throughout with the open living room and family room each graced with woodburning fireplaces. The primary on-suite bathroom has also been freshly renovated. Additional highlights in the lower level include an extra-large bedroom with New flush mount lighting, New tiled floors and an expanded laundry room. Other updates include a New Leach field System 2022, Septic system serviced in 2024, New Roof on both the home and shed 2023 and a new pool filter 2023. Best commuter location with only 52 miles to GW Bridge and an easy access to RT17. Low Taxes! Additional Information: Heating Fuel: Oil Above Ground, Parking Features:1 Car Attached. Schedule your showing today!
Courtesy: Greene Realty Group
888-278-5840
Located in the heart of the Village of Chester, this beautifully updated home offers the rare combination of modern comfort, privacy, and convenience. Just steps from Chester Academy and the Heritage Trail, this property provides easy access to walking, biking, running, local events, and community amenities while offering the peaceful retreat of your own private acreage. Set on 4 private acres, this home is a nature lover’s dream. The expansive property offers the perfect balance of open space and natural beauty, providing endless opportunities for outdoor enjoyment, family adventures, gardening, recreation, and creating your own private oasis. The large yard gives children plenty of room to play, explore, and connect with nature, while offering the space and flexibility for a hobby farm, gardens, chickens, outdoor activities, or other homesteading dreams. The entire home has been thoughtfully renovated within recent years, offering a fresh, updated feel throughout. A new HVAC system provides added comfort, efficiency, and peace of mind. The home also offers excellent future expansion potential with a full walk-out basement ready to be finished—perfect for a recreation room, guest suite, home gym, office, playroom, or media area. A standout feature is the oversized garage, providing exceptional space for vehicles, storage, hobbies, a workshop, or additional workspace. Step outside and enjoy the wrap-around back porch, the perfect place to relax, entertain, and take in the peaceful surroundings of your expansive yard. Whether enjoying morning coffee, hosting friends and family, or watching kids explore the outdoors, this space truly embraces the best of country-style living with village convenience. Property Highlights • Beautifully renovated home with modern updates • Just steps from Chester Academy and the Heritage Trail • Prime Village of Chester location close to schools, shops, and amenities • 4 private acres with beautiful natural surroundings • Perfect property for nature lovers and outdoor enthusiasts • Large yard ideal for kids to play, explore, and create memories • Endless possibilities for gardens, recreation, and hobby farming • New HVAC system • New roof • Full walk-out basement with finishing potential • Oversized garage with ample storage and workspace • Wrap-around back porch overlooking the property A rare opportunity to own a move-in ready home with land, updates, and endless possibilities—all in one of Chester’s most convenient locations. Whether you’re looking for space to grow, room for your family to explore, or the opportunity to create your own private retreat, 50 Hambletonian Ave offers the lifestyle you’ve been searching for.
Courtesy: Howard Hanna Rand Realty
845-634-4202
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.
Courtesy: eXp Realty
888-276-0630
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.
Courtesy: Coldwell Banker Realty
914-997-0097
WOW! Move right into this 3 Bedroom 2 Full bath "all on one level" (almost 1400 sq.ft.) beautifully maintained and updated END UNIT condo style home! You'll love the bright and open concept layout featuring the living room with vaulted ceilings and a gorgeous floor to ceiling fireplace as the focal point of the space. Within this area is easy access to the private deck (with new slider door) perfect for outdoor enjoyment and relaxation overlooking the pretty landscape. The kitchen has been thoughtfully renovated with new modern cabinetry, quartz countertops, updated backsplash, newer appliances (dishwasher, gas range and microwave), dedicated pantry with roll outs and ample shelving, new sink and pull out garbage drawer. Through the main entry level you have immediate access to the 1 car garage, which also has a dedicated storage space. This home has its own private entrance and the two story foyer offers a warm welcome to the unit. Notice how well maintained this home is as you tour. The primary bedroom is spectacular. This room is spacious and it has a large walk in closet and a gorgeous newly designed on suite full bathroom that feels like a "spa". Throughout the home, new flooring and window blinds have been installed, along with recessed lighting and a modern dining room chandelier. An added perk is that the entire condo was freshly painted in 2023. Further, additional significant updates offering peace of mind for years to come include: New furnace (2022) and new air conditioning unit (2023). There is also a smart thermostat system. This property is located in the Chester school district. Whispering Hills is an in-demand location - just minutes from shopping, restaurants, parks and more. Also, you'll love the easy access to main routes while enjoying the peaceful setting this development has to offer! Within Whispering Hills is the community pool for Summer fun, tennis court and sidewalks. Call for your private tour. Welcome home! *Special features sheet with more details and a floor-plan are available*
Courtesy: HomeSmart Homes & Estates
845-547-0005
Welcome to 2604 Whispering Hills! This beautifully maintained, move-in-ready 3-bedroom, 2.5-bath townhome offers comfort, style, and numerous recent updates. Major improvements completed within the last five years include new windows, furnace, water heater, washer, and dryer, providing peace of mind for the new owner. The bright, spacious floor plan is perfect for everyday living and entertaining. Enjoy your own private patio with exceptional privacy—ideal for relaxing or hosting guests. A two-car garage provides ample parking and storage. Located in the highly desirable Whispering Hills community with access to outstanding amenities, and just minutes from shopping, restaurants, parks, commuter transportation, and Routes 17 and 94. This turnkey home combines convenience, low-maintenance living, and an unbeatable location. Don't miss this opportunity—schedule your showing today!
Courtesy: Keller Williams Hudson Valley
845-639-0300
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 !!
Courtesy: MK Realty Inc
845-782-0205
Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 9 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail is thoughtfully upgraded for comfort and style. Enjoy the privacy of a modern retreat in a warm, vibrant community—the perfect setting to make new memories.
Courtesy: Coldwell Banker Realty
914-967-0059
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!
Courtesy: Serhant LLC
646-480-7665
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.
Courtesy: Ellis Sotheby's Intl Realty
845-353-4250
We are proud to introduce this cornerstone property, located within what was once a thriving enclave of artists. The same owner since 1946, this home and studio are part of a small collection of historic properties that helped define the character of the area. Now, an extraordinary opportunity awaits for the next steward to write the next chapter of this remarkable property. Originally built circa 1800, the home sits quietly within the landscape, its history unfolding through generations of thoughtful additions. Among them was a former general store, where horse-drawn carriages once stopped for dry goods and daily provisions, while the village blacksmith worked just across the way. From the road, passersby may never suspect what lies beyond. Behind its unassuming facade is a private and enchanting oasis, complete with expansive studio space that inspires creativity and retreat. The home itself is rich with period details that have been lovingly preserved through time. Wide-plank floors, beautifully patinated doors, burnished staircase railings, classic fireplaces, and a hidden back staircase all contribute to its authentic historic charm. An elevator was added for convenience to the 2nd floor. The studio still features the original general store counter and shelving, offering a rare connection to the property's past. The generous space lends itself to a wide range of creative pursuits, with a private retreat area tucked behind. Stone walls frame an intimate cottage garden, while the existing potting shed offers potential for expansion into a garage or workshop. This is more than a home—it's a piece of local history waiting to be reimagined. This weekend destination is set amid the rolling hills of Orange County, this property offers easy access to the Hudson Valley's most sought-after destinations, including Storm King Art Center, the artisan community of Sugar Loaf Arts and Crafts Village, wineries, orchards, hiking trails, and the outdoor recreation that has made the region a favored escape for New York City residents seeking space, creativity, and a connection to nature.
Courtesy: Serhant LLC
646-480-7665
New updates just completed: Fresh paint throughout and new pavers enhance the home’s curb appeal. HVAC upgrade prior to sale: The seller will professionally install a cooling HVAC system before closing. Secluded Trout Brook Estate: Expansive 5,700+ Sq Ft, 6-Car Garage, Ready for Multi-Gen Living and Entertaining. Nestled on nearly six private acres in the exclusive Trout Brook Estates, this expansive Colonial-style estate blends classic elegance with modern comfort. Built in 1993 and thoughtfully designed for multi-generational living and refined entertainment, the home offers generous space, lush privacy, and resort-style amenities. The property features a fully finished basement with a secondary kitchen, expanding living and entertaining options. This residence spans approximately 5,712 square feet and includes four bedrooms and four bathrooms. The traditional Colonial design is complemented by multi-level living areas, formal dining, a dedicated home office, and a flexible exercise/rec room. The addition of a fully finished basement with a secondary kitchen enhances hosting capabilities and provides a versatile space for guests, or recreation. Inside, cathedral ceilings, and three fireplaces add warmth and ambiance. The eat-in kitchen with granite counters remains ideal for daily meals and casual gatherings, while the spacious primary suite is complemented by well-appointed secondary bedrooms, all designed for comfort and convenience. Outdoor entertainment is highlighted by a private in-ground pool, expansive patio and porch, and a 6-car attached garage for ample storage and parking. The finished basement expands living or recreational space, offering additional options for fitness, entertainment, or quiet retreat. In total, the property combines substantial size with exceptional privacy, and it holds strong potential for future customization to suit evolving lifestyle needs. Located close to Monroe amenities, with easy access to major roadways for commuting, this home is less than an hour from New York City and near parks, nature trails, and outdoor recreation opportunities. See it, love it, own it—arrange your private showing and begin the next chapter.
Custom Adirondack-style home currently under construction on 3.54 acres in Chestertown, with completion anticipated by October 2026 or sooner, including Certificate of Occupancy. This weather-tight home is well underway with the completed shell, log siding, drilled well, septic system, 200-amp electric service, and much of the mechanical work already in place. Designed with a warm ADK cabin feel, the home features attractive log siding, black window/trim accents, a covered entry porch, and a wooded Adirondack setting. Inside, the planned finishes include a mix of wood and drywall, radiant heat in the floors, a dramatic great room, gas fireplace with stone facade, and rustic details throughout. The foundation is constructed with insulated concrete forms, adding efficiency, durability, and comfort to the lower level. The floor plan offers approximately 2,016 sq. ft. of living area, including a first-floor primary bedroom suite, open kitchen/dining/living area, entry porch, laundry, and second-floor bedrooms with open-to-below loft-style volume. The basement includes flexible future-use space, utility area, and an egress scapewell, offering potential for a future bedroom, recreation space, or additional storage. The kitchen is planned with dark cabinetry, warm wood-tone countertops, and select appliances included. No furnishings are included. Ideally located in Chestertown, this property would make an excellent Adirondack getaway, year-round residence, or ski house, with convenient access to the region's outdoor recreation, lakes, hiking, snowmobiling, and nearby ski destinations. A great opportunity to secure a custom new-construction home before completion and enjoy a brand-new residence with rustic character, modern systems, and room to personalize final touches.
Courtesy: Howard Hanna Rand Realty
845-294-3100
Welcome to an unparalleled expression of luxury living in the Town of Chester. Built in 2003, this custom-built Cape May/Colonial estate designed by award winning architect Larry Belk estate spans 4,281 square feet of meticulously designed living space, masterfully balancing grand entertaining spaces with intimate everyday comfort. From the moment you arrive, exceptional craftsmanship is on display—from the solid wood doors and dual staircases to the premium radiant-heated floors sweeping across the entire main level. The inviting foyer seamlessly transitions into the formal living and dining rooms, both framed by dramatic floor-to-ceiling windows, intricate crown molding, and striking red oak flooring with Mahogany inlays. Both formal spaces open directly to an expansive bluestone patio, offering an effortless indoor-outdoor lifestyle. At the heart of the home is a true culinary enthusiast’s kitchen, outfitted with oversized granite countertops, custom cabinetry, and a table-height center island. Immediately adjacent, a sunken family room anchored by a rustic wood-burning fireplace serves as the perfect gathering hub, featuring French doors that lead to a covered bluestone patio and a private fire pit area. Retreat to the main-level primary suite—a serene sanctuary complete with gas fireplace and French doors opening to a private, wrap around covered Trex deck. The spa-like primary bath boasts a vintage-inspired cast iron clawfoot tub, a walk-in shower, and dual vanities, all complemented by a massive walk-in closet. A dedicated laundry room completes the main level. Upstairs, discover a versatile bonus loft accessed via a spiral staircase, a full walk-up attic, and three generously sized bedrooms—two of which feature private en-suite baths and walk-in closets. The lower level is an enthusiast’s dream. Beyond vast storage capabilities, this floor houses a dedicated wine-making room and provides direct access to an extraordinary, pristine multi-car garage featuring professional epoxy flooring. A true masterpiece of design, utility, and sophistication. Enjoy effortless travel with immediate access to Route 17 (I-86) and the NYS Thruway, while mass transit options like the Chester Park & Ride and the Harriman Train Station make commuting a breeze. Located just 60 miles from NYC, you can enjoy the peace of the suburbs and be in the city in just over an hour. Unbeatable location for entertainment, dining, and shopping! You are 10 miles from the world-famous Woodbury Common Premium Outlets. Explore Chester’s vibrant local food scene, steps from local restaurants, craft breweries, and renowned local wineries. Outdoor enthusiasts will love the proximity to the scenic Orange Heritage Trail. Exceptional location, maximum convenience, and a perfect place to call home!
Courtesy: Howard Hanna Rand Realty
845-294-3100
Welcome to Brook Farm - Village of Chester, New York - Circa 1851 - 6.8 Acres. There's a moment, just after you turn onto Main Street and the house comes into view above the lawn, when you understand that this is not an ordinary property. The covered porch stretches wide across the front, the slate roof catches the afternoon light, and the whole thing sits there with the quiet confidence of something that has absolutely nothing to prove. Brook Farm has been here since 1851. It will be here long after you. This is the kind of home that changes the way you think about time. Originally the crown jewel of financier Richard Delafield's 128-acre Brook Farm estate — named after his Tuxedo Park retreat — the manor was designed from the very beginning for a life lived generously. For gathering people. For long dinners that drift into evening. For the kind of entertaining that doesn't need a theme, because the house is the occasion. Step through the front door and the ceilings rise to greet you — twelve feet of plaster and molding, the proportions of a home that was never meant to feel small. The formal rooms flow one into the next: parlor, drawing room, dining room, each anchored by original fireplaces, each telling you without a word that whoever built this place understood how a house should feel. The hardwood oak floors, the walnut trim, the two grand staircases with their original woodwork — these aren't period details. They're the bones of the place, still standing, still beautiful, still doing exactly what they were put here to do. Upstairs, four bedrooms carry the same unhurried character — rooms with depth and soul, served by two full baths and a dressing room. A walk-up third floor adds two finished bonus rooms: a studio, a library, a playroom, a quiet office above the treetops. The house keeps offering more. And then there's the basement. Name it what you want — a tavern, a speakeasy, a rumpus room — but nothing quite prepares you for it. A massive brick fireplace. A built-in bar. Full-size windows flooding the space with light. And a door that opens directly onto a sunken pebbled courtyard, walled and private, where summer evenings could easily become a habit. Beyond the main house, the estate unfolds across 6.8 acres of lawn, mature trees, and open land. A charming 882-square-foot guest cottage — two bedrooms, one bath, fully independent utilities — sits privately apart from the manor. It's the kind of setup that solves problems you haven't had to solve yet: visiting loved ones, aging parents, a long-term guest, a rental income stream, a caretaker's quarters. The dairy barn and outbuildings hint at the property's agricultural past and offer a footprint ready for whatever comes next — a workshop, a studio, a small farm, a vision that hasn't quite taken shape yet but will the moment you walk the land. There's even a tennis court. Fifty-five minutes from Midtown Manhattan, charming village setting, close to the Rail Trail, highways, the Goshen Historic Track, Legoland, the Shawangunk Wine Trail, and some of the best farm-to-table dining in the Hudson Valley — Brook Farm is private without being remote, historic without being frozen in time. Properties like this — with this much land, this much character, this much history — don't come back on the market. This one hasn't been available in over seventy years. The people who have lived here understood what they had. Now it's your turn. A special property steeped in character, with a story already written… and a bold new one waiting to begin. Full of soul and raw possibility, it’s ready for reinvention, for reimagination, for a whole new energy. Awaken its potential, elevate its spirit, and make it entirely your own. The next chapter is yours to craft. Your vision. Your legacy.
Courtesy: BHG Real Estate Green Team
845-208-9928
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
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Chester is located in New York. Chester, New York has a population of 12,477. Chester is more family-centric than the surrounding county with 37.24% of the households containing married families with children. The county average for households married with children is 36.93%.
The median household income in Chester, New York is $120,288. The median household income for the surrounding county is $85,640 compared to the national median of $69,021. The median age of people living in Chester is 39.1 years.
The average high temperature in July is 83.4 degrees, with an average low temperature in January of 16.3 degrees. The average rainfall is approximately 47.1 inches per year, with 39.1 inches of snow per year.
