Chester NY Real Estate & Homes for Sale

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.

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.

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.

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!

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.

Lovely ranch on 2 acres of land, wood fired fireplace, Central air, hardwood floors and lots of room to spread out! Beautiful Granite + oak spacious kitchen with new Stainless appliances! It's open to an eating area with sliders to the deck to enjoy the peace and quiet of the private rear! Also off the kitchen is a bedroom with closet + hardwood floors or it could be a formal dining room with French doors! Living room has a fireplace to enjoy. Master BR with 1/2 bath has an exit out to the rear! In front of the house is a unique balcony where you can keep your BBQ & comfy chairs~enjoy the view! Basement can be your office, workshop or whatever you need! Inground pool being sold as is (needs liner). Nearby is the Capelli Sports Complex! & the Glenmere Mansion! Also, close to Legoland, Castle Fun Center, Historic Goshen Trotters Track & museum, wineries, breweries and so much more! Perfect for commuters, just a couple minutes to Rt 17! House next door will be available soon~complete reno!

A/O with multiple back ups. This one is ready to go and is a nice house on a nice property. Perfect for a rehaber. Lots of possibilities in this oversized raised ranch built for an extended family. House close to beautiful stream behind the house. All cash buyers for this "AS IS" sale. Third party short sale negotiator gets additional fees from buyer.

Large four bedroom two and half bath center hall colonial built in 2000 on a beautiful cul-de-sac. The home boasts high ceilings, hardwood floors, a fireplace, open concept kitchen to family room along with a screened-in porch. The basement is full and a walkout. Attached two car garage and a lovely front porch view.enjoy the beautiful

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 mini-estate with near full privacy plus wonderful mountain views! This modern farm house features over 2,720 sq ft. and is completely CUSTOM ... build this home, or bring your own dream plans/ideas! This ONE LEVEL living floor-plan features 2 primary bedroom suites with full baths and walk-in closets; wonderful Kitchen/Great-Room open floor plan and walk-in pantry; formal dining room with a tray ceiling; THREE CAR GARAGE; Fabulous front and real front porches and more! 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.

Welcome to 40 Deer Trail Road, an exquisite and unique country retreat. This custom Colonial-style home is nestled on 9.9 acres of meticulously maintained and sub-dividable property. As you enter through the two-story entranceway, you'll immediately appreciate the attention to detail and tasteful design, including crown molding throughout the home. The main level of the house exudes elegance and functionality. A formal dining room sets the stage for memorable gatherings, while French doors open to a private den. The chef's kitchen features stainless steel appliances, granite countertops, and an expansive center island. It seamlessly flows into a spacious family room adorned with a custom stone fireplace. One of the highlights of this property is the three-season room, a true sanctuary. Complete with a custom-built bar and a wall of windows, this room overlooks a private oasis, offering breathtaking views of the surrounding beauty. Just a few steps off the main level a bonus room awaits, boasting vaulted ceilings, plenty of natural light, a full bathroom, and a private entrance with a porch. On the second floor, you'll find three well-appointed bedrooms, a full bathroom, and a generously sized primary bedroom. The primary bedroom features a walk-in closet and a stunning ensuite bathroom, adorned with granite countertops and detailed custom cabinetry. On the lower level you'll find a full bathroom, an office/den, radiant heat and a walkout to a private patio with picturesque views. The outdoor amenities of this property are truly exceptional, evoking a resort-like lifestyle. Step outside to discover a 20x40 in-ground heated pool with a natural stone waterfall, surrounded by an expansive paver patio. A wood burning fireplace and a hot tub add to the ambiance, while lush gardens enhance the tranquil atmosphere. A natural spring-fed Koi Pond, a driving range, and a nine-stall horse barn with a tack room and loft cater to the horse enthusiast, providing ample space for equestrian pursuits. Completing the outdoor amenities are an outdoor riding ring, a round pen, two paddocks and a wide-open field perfect for an afternoon gallop. Practical features of the property include a new roof, a new well, a new pool liner, and a 6-zone heating. An in-ground sprinkler system ensures the lush landscaping remains vibrant and well-maintained. This property offers an extraordinary lifestyle, combining luxury, comfort, and natural beauty. Whether you seek a private retreat, an entertainer's paradise, or a haven for equestrian pursuits, this property is sure to exceed your expectations and is located just 60 miles from Manhattan.

Beautiful TURN-KEY Arts & Crafts-style FARMHOUSE TO BE BUILT! CUSTOMIZE this 4-bdrm, 3 1/2 bath, 2,500 sq. ft home with plenty of main level living to enjoy! TWO LARGE MAIN FLOOR BEDROOMS with ENSUITE BATHS & WALK-IN CLOSETS! Upstairs offers 2 additional large bdrms (or office space) both with walk-in closets & a large full bath. GREAT ROOM with large fireplace, loads of windows with VIEWS & sliders out to the covered porch & patio! Two-car garage with storage & entrance to the mud-room & laundry/utility. Lovely front porch! OPEN FLOOR PLAN kitchen, dining and great room with a large walk-in pantry! Paved driveway, concrete walkway, landscape package, cultured stone veneer allowance, & more..ALL INCLUDED! CASH OR CONSTRUCTION-TO-PERMANENT LOAN ONLY. Come tour the lot & meet the builder in the Warwick Showroom! This will be a fantastic home with all high end finishes, standard! Lovely 1-Acre level lot w/MOUNTAIN VIEWS ... VERY COMMUTABLE!

Magnificent custom-built colonial estate situated on a 2.5-acre premium corner lot in a private subdivision with mountain views. Perfectly professional manicured landscaping surrounds the front and side of the country style porch that leads into a spacious foyer with a full dining room with custom wall panels to the right, formal living room with french doors to the left with a center hallway that leads to an open concept eat-in kitchen with fine cabinetry, granite counter tops, large island, cast iron sinks with high-end stainless steel appliances. Just off the kitchen is the family room with a 7.1 Dolby surround sound system and propane fireplace. Off the foyer in the center hall is a beautiful staircase trimmed with custom wood panels that leads to the second floor master-suite, with a master bath elegantly tiled with a whirlpool tub, and a full walk-in closet, three guest bedrooms, additional walk-in closet space, full bathroom, finished bonus room and walkup attic. The basement is professionally finished with a home office trimmed with custom wall panels, a home theater with 7.1 Dolby surround sound system, a fitness room, recreation area with additional closet space. This palatial estate also has a state-of-the-art geothermal heating/cooling system, fresh air vent unit, and spray foam insulation. With a two-car garage, Tesla wall charger, and long private driveway, it also has an amazing heated and lighted in-ground pool with waterfalls and full adult water slide, two storage sheds, a gazebo, fruit trees and so much more. No HOA fees.