Chester NY Real Estate & Homes for Sale

Welcome to 1311 Whispering Hills! This 3-bedroom, 2-bathroom condo was tastefully updated in 2020, leaving nothing to do but move in. The open floor plan features cathedral ceilings and abundant natural light, with all rooms conveniently located on one level. The formal dining area seamlessly flows into the spacious living room, complete with an electric fireplace. Step out onto the balcony through sliding doors from the living room, offering a great spot to enjoy the upcoming spring and summer days. The kitchen features newer appliances, perfect for all your meal preparation needs. Convenience is key with the LG washer and dryer setup in the laundry room. The primary bedroom includes a spacious walk-in closet and an updated en-suite bathroom. On the lower level you will find a 1-car garage with extra storage space. This location is ideal for commuters, as it is near bus stops to NYC, with easy access to major highways and shopping. Whispering Hills amenities include a clubhouse, pools, basketball and tennis courts, and playgrounds. Schedule a showing today to view this modern unit!

Welcome to your dream home nestled in the serene beauty of the Hudson Valley! This custom built 5 bedroom, 3 1/2 -bathroom colonial offers a perfect blend of privacy & convenience. Situated on a private road, you'll enjoy peaceful surroundings just a short drive to shopping, schools & transportation. Step inside to discover spacious rooms adorned with hardwood floors and abundant natural light throughout. The heart of the home is the spacious kitchen, complete with an island and eat -in nook. Entertain guests in the expansive indoor living areas, or retreat to the finished basement for movie nights or fitness fun. Outside, your own private oasis awaits, with an oversized pool and breathtaking views of surrounding nature. There is even a convenient hookup fit for an electric car. With brand new HVAC ensuring year-round comfort, this home is a true haven for relaxation and enjoyment. Seize this opportunity to make this exceptional property yours today! MW schools/Town of Chester

WOW! ~~Lovingly Maintained to the Hilt" ~~ One level living with Contemporary drama! PERFECT FOR GUESTS! Accessory suite set-up w/separate entrance; **Side by Side** SITS PICTURE PERFECT ON 2.8 Acres with views to live for & backing up to State Parklands consisting of approximately 900 acres with benefits of hiking & horse trails! CUSTOM BUILT to perfection by "ORIGINAL & ONLY OWNERS!! Centrally located to Chester shopping, restaurants + movie theater & just minutes to Sugar Loaf & near Garnet Health, Crysal Run Med Centers. ~MAIN Level 1~ LR w/stone fireplace, formal DR, Eik, 4 seasons room, Sunken Mstr BR, Mstr Bth, BR #2, BR #3 + Apt w/1 BR, LR & full Bath.. LOWER LEVEL of house; Full finished walk-out bsmt / entertainment room w/brick frpl, laundry room, office, wine cellar, full bath, 2 car garage. **Handicap Assessable**... Approx 3/4's of the house is solid brick & stone...220 Elec in shed...

Move in ready. This pristine 2 bedrooms, 1.5 bathrooms with fireplace and washer and dryer in the unit. Large walk in closet in the bedroom. Walk out garage with storage and a private outside patio for relaxation. Includes, Pools, playgrounds, tennis courts, dog parks and close to biking trails. Public transportation and shops are only minutes away. Pet friendly.

Nestled within an exclusive, top-tier development, this luxurious custom-built home spans across 2.4 expansive acres, offering awe-inspiring views of the serene Vista Valley. The residence boasts a plethora of custom upgrades and distinctive design features. Each of the four bedrooms is a private sanctuary with its own ensuite bathroom. The heart of the home is a magnificent two-story great room, bathed in natural light and presided over by an elegant second-floor balcony. Practicality meets style in the fully integrated mudroom, complete with built-in storage.The home is graced with 9-foot ceilings, rich hardwood floors, and spacious custom closets throughout. Culinary dreams come true in the stunning kitchen, equipped with top-of-the-line appliances, a vast walk-in pantry, and an island adorned with a cascading quartz countertop. The master bedroom is a true retreat, featuring vaulted ceilings, two expansive walk-in closets, an oversized shower, a double vanity, and a sumptuous soaking tub.Designed for both comfortable living and sophisticated entertaining, the home includes expansive living spaces and oversized windows that flood the space with natural light. The first-floor guest accommodations are ideal for extended family or a nanny, complemented by a convenient second-floor laundry. Additional features include a large walk-in attic and an enormous walk-out basement, offering ample storage and potential living space. The home is prepared for any contingency with an emergency transfer switch for a backup generator. This brand new residence, complete with the latest mechanical systems, requires nothing more than to be moved into and cherished as a dream home come true.

Renovated end unit Condo nestled in the Village of Chester, Chester Union Free School District, and within close distance of Route 17 and Route 6. A location great for commuters to NYC and close distance to local shopping centers, eateries, and entertainment activities such as The Castle Fun Center and Legoland. Highlights this home has to offer starts with all hardwood floors, a skylight ceiling on the second-floor hallway, wooden fireplace, built-in closet in master bedroom, and patio furniture. This condo also features a 2-car attached garage with storage space. The association amenities: clubhouse, two pools, gym, basketball and tennis courts, and tot playground!

Bright and Spacious 3 bedrooms, 2.5 bathroom townhouse in Whispering Hills, Chester. The first floor features a living, dining, half bath, kitchen, and laundry. The open layout creates a seamless flow. Upstairs has master with it's own bathroom and walk-in closest. Two addition bedrooms share a bathroom. Two car attached garage with additional storage space for snowy winters. HOA fees cover water, trash collection, grass cutting and snow removal. Also, two pools, basketball courts, tennis courts, gym, playgrounds. Schedule your appointment today, this one won't last.

Discover the Dogwood model in Whispering Hills, offering a two-car garage, a living room with a cozy fireplace, and a kitchen with stainless steel appliances, granite countertops, and a breakfast nook leading to an expandable outdoor deck for enhanced enjoyment. The dining area is perfect for cozy gatherings, complemented by a spacious living room with a guest bathroom. Upstairs, the master suite boasts high ceilings, alongside two additional bedrooms and ample storage, ensuring comfort and convenience. Enjoy the clubhouse, park, gym, and pool amenities, embracing a low-maintenance lifestyle near shopping centers, major highways, and schools. Just a 45-minute commute to NYC, this home offers a perfect balance of comfort and convenience in a sought-after community. A rare opportunity to experience the best of suburban living with urban accessibility.

This single-family house is a rare find with gorgeous landscaping and an on-ground pool. The ground level features a hallway, living room, and dining area with beautiful hardwood floors, creating a warm and inviting atmosphere. The kitchen is nice and spacious, leading into a cozy and comfortable family room. With 3 bedrooms on the upper level, one in the basement and potentially another one on the ground level, This house is the perfect space for anyone who wants an affordable and spacious house in a peaceful and relaxed area.

Prepare to be charmed by this meticulously maintained custom-built RANCH home, crafted with love and attention to detail by its original owners. As you step inside, you'll be enveloped in a seamless blend of mid-century design and modern comfort, creating an inviting atmosphere that feels like home. Every aspect of this custom residence has been carefully considered, offering an effortless flow that epitomizes one-level living at its finest. Whether you're unwinding in the cozy living room with mountain views, hosting gatherings in the welcoming dining room, or preparing meals in the well-appointed kitchen, you'll feel a sense of belonging from the moment you arrive. This home boasts three spacious bedrooms and two immaculate full bathrooms, complemented by an additional office on the main level and a convenient laundry/mudroom, enhancing its functionality and flow. Outside, the property exudes tranquility, with well-tended grounds featuring an inviting paver walkway leading to dual entrances. The back sliders open to a covered patio that offers a serene retreat for outdoor relaxation and entertainment. An impressive full unfinished basement will simply blow you away with its endless potential, while the heated two-car garage adds practicality to this charming abode. Nestled in a neighborly neighborhood, this village gem offers easy access to nearby amenities and is a commuter's dream, located just one hour from NYC. Don't let this opportunity slip away schedule a showing today and experience the timeless allure of this must-see home in the Cherry Heights neighborhood. It truly embodies the perfect blend of comfort, convenience, and charm that defines village living at it's best in the heart of the Hudson Valley.

One of a kind custom built Country Contemporary Home. A Private Paradise this Unique Open Floor plan welcomes bright warm sunlight in each room. Top of the line hardwood floors and trim throughout the house. 5 Bedrooms, 4 Bathrooms. Master bedroom with fireplace and walk out balcony. 13x25 dining room with french doors. 26 Ft. Ceilings in Living Room with stone accented wood stove. Enjoy the back deck with privacy. New furnace heating system. This is a very special private property minutes to NYS Thruway,State Parks. 45 min to NYC. Two story 1,000 square foot detached cottage holds a world of possibilities on the property just need's to finishing touches on the interior.

Looking for a great opportunity? Look no more! This property has tons of potential and is average in living space size for the neighborhood. It is located close to main roads with easy access to local amenities, such as shopping, banking, schools, and various eateries. Per our Appraisal describe the subject property is a SFR (colonial) built in 1992. It has approx. 2768 sq ft. and has 4 bedrooms and 2.5 bath with full/unfinished Basement and 2-Att garage. The property is on 1.60acre. *** Seller makes no guarantees about property's condition, room count or other physical characteristics nor does seller guarantee accuracy whether property is on public sewer or private septic. ***

Welcome to Whispering Hills, where this inviting 2-bedroom condominium awaits to envelop you in comfort and convenience. Step in to the freshly painted living area, equipped with a wood burning fire place. Upstairs you'll find 2 large bedrooms with brand new carpeting, filled with natural light. Impeccably maintained interiors with contemporary finishes create a cozy ambiance, while community amenities including a swimming pool, fitness center, and playground enhance your lifestyle. Situated just minutes from major highways, shopping center and public transportation this condo provides the ideal blend of serenity and convenience. Don't miss the chance to make this your new home sweet home in Whispering Hills. Schedule your private viewing today and experience the beauty of condo living at its finest. HVAC system is 1 year old.

Welcome to a unique opportunity to own an exceptional property in the charming artisan Hamlet of Sugar Loaf, New York. Sugar Loaf is nestled in the picturesque Hudson Valley and just one hour of NYC. Become a part of the close-knit Sugar Loaf community, where local artisans, eclectic shops, and a vibrant cultural scene await. Engage in community events, markets, and festivals that celebrate the lively artist of this hamlet. Whether you're seeking a personal haven or considering an investment opportunity, this property offers the potential for financial growth in a region that continues to attract attention and investment. Step back in time as you enter this impeccably maintained 1850's farmhouse, where original details such as hardwood flooring, molding, trim, and bespoke built-ins with woodworking accents designed by the owner create a tale of dedication to artistry and authenticity. The main residence boasts of three spacious bedrooms, an office, formal living, parlor, and dining rooms. The spacious kitchen provides the perfect canvas for modern living infused with historic character. As a bonus, the property features a one-bedroom auxiliary apartment adjacent to the main house, offering flexibility for guests or in-laws. Explore the endless possibilities with two additional outbuildings on the property. Previously served as an art gallery, this ideal space can showcase your artistic endeavors, host community events or be utilized as your own personal office. The two-story barn, currently used as a woodworking shop, provides ample room for creative pursuits, storage, car hobbyists or conversion to suit your vision.

Majestic turn-key Georgian estate lovingly restored to perfection by current owners. Long sweeping driveway brings you to the formal entrance of this brick beauty sited between Sugar Loaf Mountain and Glenmere Lake with panoramic views. Formal in its grandeur yet lending comfort in perfectly proportioned rooms. Grand center hall foyer leads to a formal dining room, expansive sitting room with doors leading out to veranda enclosed by sparkling white railing with balusters. The den is a showpiece with a priceless series of original murals painted by John Ferguson Weir, the former director of fine arts at Yale. In the late 1800s, he was a frequent visitor to the estate. These one-of-a-kind paintings depict scenes of the natural surrounding land, the essence of beauty found in the Hudson Valley. This house has amazing flow for entertaining on a small scale or large gatherings. Outside walk up the hill to an outbuilding and large enclosed garden for cutting flower beds or a victory garden. Expansive slate patio and separate fireplace beckons for evenings spent under the stars.

On almost 1 acre, this corner lot, 2700 sq foot bilevel has a lot to offer! The main part of the house has hardwood floors throughout and plenty of space and bright light. The deck off the dining room faces the in-ground pool and the expansive backyard. Not only is there a wood burning stove on the lower level, there is an additional bedroom and newly updated full bath. The in-law suite features a galley kitchen, walk-in closet and full bathroom. In addition to its own front entrance, it also has a back door with access to the pool and backyard along with separate electric and gas meters. Don't miss this gem!

Welcome to the charm of this delightful, raised ranch situated on almost a half-acre, backing up to a stream and Goosepond Mtn State Park. This home boasts crown molding, a new updated bathroom with tile, newer appliances, granite countertops with wooden kitchen cabinetry, fireplace, central air, large back porch for entertaining, shed and 6 heating zones are just a few of the amenities that make this home truly special. The full finished basement has radiant heat throughout plus a jacuzzi tub, pellet stove and open space for entertainment / storage. With its prime location close to shopping, a great commuter location and Monroe Woodbury Schools, this residence offers an exceptional opportunity to embrace a comfortable and fulfilling lifestyle. A must see!

In the heart of Hambletonian country, Chester, NY is "Brook Manor" the former horse training estate of financier and Tuxedo Park resident, Richard Delafield. The estate, now an assemblage of 3 parcels of just under 10 acres, has a rich history and was home to Delafield's farm Superintendent. Perched on a sweeping lawn above Main Street, this stately brick, slate, and carpenter's lace adorned manor offers compound-level privacy and amenities - including a separate cottage - yet is accessible to the village. Circa 1851, the approx. 4,000 sq. ft. manor home was originally part of the 128-acre "Brook Farm", named after Delafield's Tuxedo Park property. It was designed by owners prior to Delafield for grand entertaining. Out front, a covered porch greets you with views over Chester Village. Inside are the formal center hall, parlor, dining and drawing room w/ fireplaces, some areas here boasting 10' ceiling heights and gorgeous hardwood floors. A working-kitchen with dinette, butler's pantry and powder room round out the main level's openness and flow. Upstairs, by both front and rear staircases, the 4 bedrooms have character and period architectural details and are served by 2 full bathrooms. The 3rd floor walk-up offers 2 finished bonus rooms. A walk-out basement is reminiscent of a colonial tavern with its rustic bar, fireplace and an exterior door that leads to a pebbled courtyard. The home's distinct warmth and flow are perfect for both entertaining and daily living. The expansive land is well-suited for recreation, gardening, and outdoor entertaining. The original 128-acre property was once replete with a state-of-the-art horse training track, stables, barns, tenant houses, an icehouse, chicken coops and more. Currently the property is just under 10 acres combined; the modest accessory cottage, tennis court and barn remain, some needing work. Included in the sale is the 4-bedroom main home and the 2-bedroom cottage on a 6.8-acre parcel, and two additional adjoining land parcels which are separate tax lots of 2.1-acres, and .78-acre. With hundreds of feet of road frontage on the front parcel, there may be the possibility of future subdivision. Conveniently located in the heart of Orange County, this unique property bundle is near major highways and area attractions including Orange County's "Rail Trail", Goshen Historic Track, Legoland NY, black-dirt farm-to-table restaurants/breweries/distilleries, Shawangunk wine trail and more. It's just ~75 minutes from NYC. A one-of-a-kind lower Hudson Valley village estate, not to be missed.

Discover luxury and comfort in this contemporary ranch home, offering 4 bedrooms, 3 full bathrooms, and 1 half bath, two of which are newly updated. The spacious eat-in kitchen, family room, dining room, and separate lounge area provide ample space for living and entertaining. Upstairs, a large attic boasts a bedroom and full bathroom, perfect for guests or a private retreat. Additional features include a two-car attached garage, large unfinished basement, and a new 8ft storage shed. Practical amenities such as a water softener and a newly installed 12ft Gutter Helmet with a triple lifetime warranty ensure convenience. Situated on 6.3 acres of land with zoning for two additional buildable lots, this property offers both privacy and potential for expansion. Don't miss out on the opportunity to make this exceptional home yours!

Experience Unparalleled Luxury Living in Every Detail. Sitting on an expansive 2.6-acre estate in the Warwick Valley School District, this high-end custom-built home epitomizes luxury living at its finest. Every detail of this exquisite residence has been meticulously crafted using the finest quality materials, creating a masterpiece of architectural design and opulence. As you enter the home, you are greeted by 8-foot mahogany doors that lead into a foyer adorned with mahogany moldings and window sills. The attention to detail continues throughout the home, with all closet and bedroom doors also crafted from 8-foot mahogany, adding a touch of elegance and sophistication to every room. The heart of the home, the gourmet kitchen, where culinary dreams come to life. Adorned with Cherry Cabinets, granite countertops, and backsplash, this kitchen is a chef's paradise. Equipped with top-of-the-line appliances, including a double Wolf range with griddle, Wolf range back guard, Wolf hood and blower, Liebherr refrigerator and freezer with bio fresh vents, and Miele dishwasher, no expense has been spared in creating a culinary oasis with radiant heated floors that provide warmth and comfort throughout the entire upper level. Step outside and be enveloped by the beauty. The patio and walkways are lined with double blue stone, providing a luxurious setting for outdoor entertaining or simply relaxing in the serenity of nature. The brand new wrap-around Trex deck and rails offer the perfect spot to soak in the picturesque views of the surrounding landscape and enjoy a swim in the large above ground pool. Indulge in the ultimate relaxation experience in the main bath, featuring a luxurious lion claw soaking tub. Every element of this space has been carefully curated to create a spa-like atmosphere, where you can unwind and rejuvenate in style.

Welcome home to this TURN KEY 4 bedroom 2 and a half bath colonial with newly finished hardwood floors, updated eat-in island kitchen with stainless steel appliances and quartz counter-tops. The master bedroom features a walk-in closet and master bathroom. This home's lovely family room and dining room are perfect for gatherings with plenty of space to spare. Enjoy the GREAT views from the beautiful 3 season room or deck overlooking the 5.7 acre property. Walk-out basement for easy access to the above ground pool. This home is both a private location but also provides easy access to highways. Don't miss your opportunity to make 322 Black Meadow Road your next Home Sweet Home!

Discover the modern marvel you've been dreaming of! This unique, custom-built stone and stucco residence is nestled on a serene 5-acre lot, offering pristine conditions and readiness for immediate occupancy. Designed for a luxurious lifestyle, its welcoming two-story foyer with a striking central staircase sets a tone of contemporary elegance. The home is bathed in natural light, highlighting sleek hardwood floors and refined modern millwork, including sophisticated crown, base, and window moldings. The living room, with its high ceilings and a cozy fireplace, features expansive windows that frame stunning mountain views and open onto a private deck, perfect for relaxation. The state-of-the-art kitchen is a chef's paradise, boasting granite countertops, stylish cabinetry, high-end appliances, and dual islands for culinary exploration. Adjacent is a spacious dining area, ready for festive gatherings. The main floor also hosts a luxurious owner's suite with a sitting area, fireplace, and an en-suite bathroom equipped with a jetted tub and steam shower, ensuring a private retreat. With a three-car garage and a dedicated laundry room, convenience is key. The upper level presents a loft-like ambiance, leading to the primary suite, two additional bedrooms, a full bathroom, and a versatile bonus room. The expansive walk-out basement opens to a secluded patio, ideal for hosting summer events. This exceptional home, set within the prestigious Warwick School District, represents a rare chance to embrace a bespoke, modern lifestyle.

Welcome to this immaculate, custom built colonial within the Monroe Woodbury School District. This stunning home boasts 4 bedrooms, 3.5 bathrooms, and an impressive 4,600+ square feet of living space. Step inside and be greeted by the welcoming 2 story entry with gleaming hardwood floors and custom mouldings throughout. Spacious open floor plan with oversized kitchen with breakfast area, living room featuring a fabulous two sided stone fireplace with a woodburning stove on the kitchen side, formal dining room and 1st floor bedroom w/ full bath. 3 additional bedrooms in the upper level including the primary suite plus a fabulous family room with so much potential. One of the highlights of this home is the beautiful in-ground Gunite pool with built-in hot tub and spacious outside entertainment area. Located in the desirable town of Chester, you'll enjoy a peaceful and private setting while still being convienently close to shopping, dining, and entertainment options. Don't miss out on the opportunity to make this impeccable colonial your new home.

"WOODSIDE" - a legacy property for the ages. This expansive colonial farmhouse sits on 10 acres of sweeping emerald lawns backed up to forested lands. This cherished offering is a recently created parcel carved from one of the largest land preservation projects executed in the region, the intended preservation of iconic Sugar Loaf Mountain and some of its surrounding acreage. The home features many 19thc. & 20thc. period details including hardwood floors in the gorgeous front parlor rooms. Across its approx. 6,600 sq. ft. are 6 bedrooms and 3.2 bathrooms, including the spacious, contemporary c.1960's addition that creates a desirable, open twist on this antique beauty. Here, vaulted, beamed wood ceilings, walls of windows, and fireplaces punctuate two large living / recreation rooms on the 1st and 2nd level. The in-ground swimming pool, just off the back is complemented by a pool shed, and in the house - a locker/dressing room area. Across the large, paved driveway is "Woodside 1871", the prominent red barn of approximately 8,000 sf with 5 bay garage; imagine the possibilities! Up a gentle rolling drive on the lawn is structure #3, the "lodge", a fine post and steel shed building with an insulated room previously used as a hunting lodge. This building sits high where one can capture medium-distance scenic views over central Orange County as well as Woodside's breathtaking expanse. Prior to its current acquisition Woodside was lovingly cared for by one owner for many decades. Woodside is perhaps one of the most inspiring real estate offerings to come available in recent times and is well-suited for connecting with nature, entertaining, pursuing hobbies and many imaginative uses with its abundant indoor / outdoor space and amenities. The property is highly centralized to the hamlets/villages of Sugar Loaf, Chester, Monroe and Warwick and major Orange County attractions/destinations such as orchards/vineyards, Sugar Loaf PAC, LegoLand, Woodbury Common, West Point, Goshen Historic Track and more! All just about 75 minutes to NYC in NY's coveted Lower Hudson Valley.

Welcome to your dream home, where modern luxury and comfort meet in this stunning 5-bedroom, 3-bathroom oasis. This property has been thoughtfully designed and upgraded to create a truly exceptional living experience. The heart of this home is the newly customized kitchen, an absolute masterpiece. It boasts granite countertops, stainless steel appliances, and under-cabinet lighting, creating an inviting atmosphere for culinary enthusiasts and social gatherings. Bamboo ceiling fans, recessed lighting, and crown molding above the cabinets enhance the kitchen's elegance and functionality. The upper level features a bright living room, a spacious master bedroom with its own master bath, and two additional bedrooms, all filled with natural light. On the lower level, discover versatility with two additional bedrooms, perfect for extended family or a home office. The family room offers a cozy retreat with a wood-burning fireplace, setting the stage for memorable moments and a renovated expensive bathroom. Step outside to your private oasis, complete with an above-ground pool and a leveled backyard that's ideal for outdoor entertaining and activities. A generous driveway with tasteful paver accents provides ample parking space. Recent updates include a 17kw generator, a one-year-old pool deck, a brand new water softener, baseboard heat, boiler, and central AC, ensuring your peace of mind. This is your opportunity to live in luxury and convenience, all in a tranquil and private setting. Don't let this chance slip away schedule your viewing today!