Courtesy: Century 21 Full Service Realty
845-782-2221
Welcome to your private, wooded oasis! This charming home perfectly blends convenience with comfort, featuring an ideal layout for multi-generational living or guests with two bedrooms and a full bathroom on the main floor. A cozy wood insert is the heart of the main living space, creating both warmth and a wonderful ambiance on chilly evenings. Beyond the existing bedrooms, there is additional flexible space on the main floor that could serve as a dedicated office, den, or playroom. The current owners are maximizing the space by utilizing it as a third main-floor bedroom. Unbeatable Outdoor Entertainment Step outside to your incredible backyard retreat. This true oasis features a heated pool, a charming fire pit for evening gatherings, and a spacious back patio with awnings that offers plenty of room for outdoor dining and cooking. An added outdoor shower is perfect after a swim. For the culinary enthusiast, the sellers have built three outdoor ovens! Expansive Acreage and Versatility The property spans a generous five acres, offering incredible space and flexibility. Two acres are fully fenced, creating a secure area, while the remaining three acres are perfect for recreational vehicles, ATVs, or other outdoor pursuits. A unique feature is the additional sunroom, currently serving as a dedicated space for a home-based business, offering even more versatility. Spacious Second Floor Sanctuary The second floor is dedicated to relaxation and space, featuring a total of three bedrooms. The primary suite is a spacious haven complete with a private ensuite bath. The primary bedroom boasts a huge closet and there's a huge hall closet that offers exceptional storage for the second floor. The second upstairs bedroom also offers great comfort and has access from the bedroom to the second full bathroom. The third bedroom on the second floor provides extra space for family or guests. This home is a perfect blend of indoor comfort, dedicated main-floor living, outdoor entertaining, and acreage for all your hobbies!
Courtesy: Howard Hanna Rand Realty
845-986-4848
Thoughtfully repositioned with a nearly $15,000 price adjustment makes this Country Woods colonial an unbeatable value! Now priced to allow for updates while securing a prime location, generous living space, a beautiful setting, and room to add your personal style. Country Woods is one of Chester’s most sought-after neighborhoods. This handsome Colonial sits on 1.7 landscaped acres and offers over 3,100 square feet of comfortable living space. A wrap-around front porch invites you inside, where a two-story foyer and 9-foot ceilings create a bright and spacious feel. The formal living and dining rooms flow seamlessly into the kitchen, complete with Corian counters and everything you need to prepare your favorite meals. The casual dining area opens to a warm and inviting family room featuring a vaulted ceiling, fireplace, and a wall of windows framing peaceful views — the perfect spot to gather for movie or game night as you watch the snow falls outside. A first-floor bedroom offers flexible space for a home office, guest suite, or quiet meditation room. A conveniently located laundry room and half bath complete the main level. Upstairs, unwind in the primary bedroom suite, plus three additional bedrooms and a full hall bath. Need more space? The full walk-out basement provides endless possibilities — a home gym, game room, or recreation area — the choice is yours. Step outside to enjoy your own private retreat, ideal for entertaining, gardening, or simply relaxing on the oversized deck overlooking a tranquil Koi pond with waterfall and wooded backdrop. Conveniently located near major commuter routes, shopping, Woodbury Common Premium Outlets, schools, cafes, and restaurants — this home truly has it all.
Courtesy: Four Seasons Sothebys Intl
518-822-0800
Set on 10 private acres with sweeping mountain views from nearly every room, 69 Cedar Pond is a five-bedroom, eight-bath estate that exemplifies expansive design and contemporary style. The striking A-frame architecture, double-height windows, and soaring ceilings create dramatic, light-filled interiors where every angle frames the surrounding landscape and sunsets. A three-story entry sets the tone, leading into an open great room anchored by a statement fireplace. Walls of glass blur the line between indoors and out, opening to an 1,800 sq ft deck that wraps the home with extraordinary vistas and flows seamlessly to an outdoor bar, dining, and lounge area with fire pit—perfect for entertaining on a grand scale. Expansive spaces continue throughout the main level, which offers two bedrooms with luxurious en suite baths, a powder room, a chef's kitchen, a dining area, and a breakfast nook. Upstairs, the primary suite is generously scaled, with sweeping views and a spa-like bath featuring a soaking tub, private water closet, and double vanity. This level also includes an additional bedroom and a fully renovated guest wing with its own kitchen, great room, bedroom, bathroom, private balcony, and separate exterior entrance for added privacy. The versatile lower level includes a family room, gym, two bedrooms, a wet bar, and walk-out access to the property's outdoor amenities. Every major element has been thoughtfully upgraded—new roof (2020), mechanicals and electrical (2019), furnace (2019), luxury baths (2021), and kitchen appliances. Despite its impressive scale, energy-efficient systems keep the home comfortable and remarkably cost-effective. The 10-acre property is as versatile as the home itself: enjoy private hiking trails, host open-air gatherings, or create a resort-style retreat with a pool, tennis court, or gardens. Nearby vineyards, ski slopes, and Hudson Valley attractions complete the lifestyle.
Courtesy: Keller Williams Hudson Valley
845-610-6065
Discover the perfect blend of versatility and charm with this exceptional property. The main house offers three levels of comfortable living, including four bedrooms, three baths, and a spacious kitchen ideal for gathering and entertaining. The thoughtfully renovated barn extends your options with beautifully finished space that carries rustic character alongside modern updates. Whether you envision a studio, home office, entertainment area, or creative retreat, the barn provides a unique extension to the main home. This property opens the door to endless possibilities make it yours today!
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: Our House Real Estate Group
845-705-8093
A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This will truly be a lovely property with land, privacy and wonderful mountain views! This modern farm house cape features over 2,600 sq ft. and is completely CUSTOM and DELIVERED TURN-KEY ... build this home, or bring your own dream plans/ideas! This ONE LEVEL living floor-plan features a primary bedroom suite with full bath and walk-in closets plus a second first floor bedroom or office; a wonderful kitchen/great-room open floor plan and walk-in pantry; formal dining room; fabulous front and rear covered porches and more! Optional finished bonus room on the second level can add an additional 410 sq ft. .... Buyer-Financed CONSTRUCTION TO PERM FINANCING OR CASH ONLY.... Very commutable plus minutes from the vibrant town of Sugar Loaf and Chester, NY!... TO BE BUILT, may have additions/subtractions to price for customization, the taxes are not known at this time, and the attached photos may be computer-generated images and are depictions of what the property may look like.
Courtesy: Century 21 Realty Center
845-781-8100
Motivated Seller!! Welcome home to this storybook setting, where a majestic weeping cherry blossom greets you with it's graceful cascade of blossoms each spring. This beautifully preserved historical farmhouse set on 1.7 acres along a scenic country road just down the lane from a local farm where the soft "mooing" adds to the peaceful rural charm. Sitting pretty on a corner lot with a circular driveway, this home offers privacy, character, and modern updates. Step onto not one, but two front porches, perfect for morning coffee or unwinding at the end of the day. Enjoy summer gatherings on the large patio with propane-connected grill and a metal canopy for shade ideal for entertaining. Make a wish at your very own fully functioning wishing well, a whimsical touch that makes this property feel like home. Nature lovers will appreciate the grapevine, blueberry bush, and pear tree, as well as the proximity Goose Pond Mountain State Park making this a fantastic retreat for hikers and outdoor enthusiasts. Inside, you'll find the warmth of hardwood floors throughout and a cozy, rustic feel highlighted by original wooden peg support beams and stunning stone fireplace with a wood-burning stove insert, recently cleaned and inspected. The eat-in kitchen with bar seating is perfect for casual meals and conversations. Upstairs the prime bedroom features an ensuite, with two additional generously sized bedrooms offer ample space. The main bathroom includes a charming clawfoot tub and direct access to the backyard, adding convenience and vintage character. Additional highlights include: Detached garage with attached workshop, recently updated shed and barn, woodshed included, septic system pumped and cleaned June 2025 and furnace serviced and maintained annually. This farm house truly combines timeless charm with everyday functionality. Whether you're enjoying sled rides in the yard or summer evenings on the porch, this home offers the best of country living - just minutes from trails, nature, and small-town comfort. The area is rich in local attractions, including West Point Military Academy, Woodbury Commons premium outlets, Harriman state park, Bear Mountain State Park, Lego Land, Vinyards and Farms and so much more... Great location for commuters with plenty of Public transportation and minutes away from major highways.
Courtesy: Howard Hanna Rand Realty
845-294-3100
Welcome to an extraordinary 4,400+ square foot residence in the coveted Warwick School district, where luxury and lifestyle converge to create the ultimate entertainer’s dream. This meticulously maintained and thoughtfully updated home offers breathtaking panoramic views, inviting you to unwind in the serene front atrium or the sun-drenched sunroom at the rear. Step inside to discover a harmonious main floor, where an open-flow layout seamlessly blends with versatile spaces tailored for a home office, music room, or study. Freshly painted in a neutral palette, the living room, complete with a TV and Bose surround sound system (included), sets the stage for memorable gatherings. The adjacent kitchen flows effortlessly into a convenient laundry and pantry room, strategically positioned off the garage for easy grocery unloading and discreet meal prep, keeping your entertaining space pristine. Ascend to the upper level, where the master suite serves as a tranquil retreat, boasting brand-new flooring, fresh paint, a modern ceiling fan, and a luxurious 2024-renovated bathroom featuring new fixtures, elegant tiles, and a rejuvenating steam shower. Three additional bedrooms share a fully renovated, contemporary bathroom with sleek fixtures and a walk-in shower, ensuring comfort for family or guests. The walk-out basement, currently a stylish home office, offers boundless potential as a guest suite or multi-generational living space, complete with a private bathroom and dining area for extended stays. The festivities continue outdoors on a private deck and patio, where you can luxuriate in the BRAND NEW hot tub, take a refreshing dip in the pool, or gather around the firepit for s’mores under the stars. Host unforgettable gatherings with the poolside TV, outdoor kitchen, and gazebo bar area, perfect for grilling favorites or crafting cocktails. Nestled just minutes from Harriman, Legoland, Woodbury Commons, and major shopping, with easy access to train and bus lines, this home offers both seclusion and convenience. A scenic drive to the charming Village of Warwick and approximately 50 miles to the George Washington Bridge make this an ideal retreat for those seeking a blend of rural serenity and urban accessibility. This is more than a home—it’s a lifestyle.
Courtesy: eXp Realty
888-276-0630
Discover a rare opportunity to own a one-of-a-kind estate set on 53 sprawling acres in the heart of Chester, NY—perfectly suited for luxury living, farming, or future development with subdivision potential. This impressive property features a 3-car garage with 10-foot doors, outdoor wood-burning furnace, and two 250-gallon oil tanks for efficient heating. Nature lovers and hobby farmers will appreciate the large chicken coop housing up to 200 chickens, an 8x12 shed formerly used for hunting dogs, and over 40 mature fruit trees, including pear, cherry, apple, and peach. Enjoy miles of well-maintained horse trails and approximately $30,000 in marketable timber. Whether you’re envisioning a private retreat, equestrian estate, or long-term investment, this exceptional property delivers endless possibilities.
Chester is located in New York. Chester, New York 10918has a population of 12,477. Chester 10918 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 10918 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 10918 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.
