The median home value in Chester, NY is $348,000.
This is
higher than
the county median home value of $320,000.
The national median home value is $308,980.
The average price of homes sold in Chester, NY is $348,000.
Approximately 77% of Chester homes are owned,
compared to 17.5% rented, while
6% are vacant.
Chester real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you like to see a property, contact Chester real estate agent to arrange a tour today!
Learn more about Chester.
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. ***
Open House:
Saturday, 3/30 11:00-1:00PM
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.
Open House:
Saturday, 3/30 1:00-3:00PM
Welcome to this charming 3 bedroom Ranch Home! Nestled in a quiet development, this home offers convenience and comfort. As you enter, you'll be greeted by the warmth of hardwood floors that flow throughout the living space. The living room is bathed in natural light, creating a cozy ambiance perfect for relaxation or entertaining guests. The kitchen and dining area is located right off the living room, and adjacent to the kitchen is a spacious sunroom, where you can bask in the sunlight while enjoying your morning coffee or unwind with a good book in the evenings. Venture downstairs to the expansive finished basement, where endless possibilities await. A generous family room provides the ideal extra living space. Need a quiet place to work or study? You'll find a dedicated office area that offers privacy and comfort. There is also a a separate laundry room, beautiful bathroom and den with sliders to walkout to the backyard. Outside, the flat lot offers plenty of space for outdoor activities. This home has it all!
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 12' 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.
MINT! MINT! MINT CONDITION! Its a Beauty! Move right in with Nothing to Do! Open Floor Plan! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage with Driveway Parking! Eat In Kitchen with Stainless Steel Appliances, Granite Counter Tops, Island, Tiled Back Splash and Under Cabinet Lighting! Over Sized Master Bedroom Suite with Sitting Area and Two Walk In Closets! Living Room with Gas Fireplace! Dining Room with Door to Trex Deck that has Beautiful Mountain Views! Recessed Lighting! Full Unfinished Walk Out Basement with Sliders to Patio! Warwick Shcools! Close to Major Highway for Easy Commute!
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.
Wow! TWO FAMILY SIDE BY SIDE DUPLEX SITS PICTURE PERFECT ON 2.8 Acres with outstanding 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 owner!" ~MAIN HOUSE 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 main house; Full finished walk-out basement / 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...
"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!
Nestled in Chester, NY, this Mother-Daughter Cape Cod residence harmoniously blends charm and modern comfort. This home features almost 3,000 sq ft. The spacious main living area, features 4 bedrooms. The first floor boasts two bedrooms, bathed in natural light, alongside an updated kitchen. Upstairs, a master suite and a bedroom offer tranquility and stunning farm land views. Meticulous grounds, sitting on a third of an acre, connect to the Heritage Trail, providing recreation and breathtaking vistas. The lower level features two bedrooms, a bathroom, and a spacious living room, offers a private retreat for guests or potential rental income. This unique design ensures both connection and independence. This Cape Cod retreat invites you to a lifestyle where charm meets modern living. With prime location, updated features, captivating views, and expansive living space, this property is a NO BRAINER a place where tranquility and convenience seamlessly converge on a third of an acre.
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
Welcome to Sugar Loaf Estates! This lovely 4 bedroom 2 1/2 bath colonial with total square footage of 3223ft. (700 sq ft is finished rec space in the basement) on a third of an acre is now ready to welcome its new owners. IF YOU HAD A WISH LIST, what would be on your list? HOW ABOUT ... Within an hour to New York City! Located in the Warwick Valley School District! LOCATION, LOCATION, LOCATION!!! Close to a food store and quaint shops as well as walking distance to restaurants and just minutes from Route 17 (2.2 miles). On the first floor you will find a generously sized living room, dining room, family room & eat-in kitchen, half bath and laundry room as well. The gas fireplace located in the living room will keep you and your guests toasty on those cold winter evenings. The living room is also wired for a home speaker system. The second level has four nicely sized bedrooms (some with vaulted ceilings), as well as a full bathroom in the hallway and a master bathroom with shower and jetted tub. The primary bedroom also has two large walk-in closets. For even more versatility, the spacious walk out basement (entrance is next to the garage doors) is finished, heated and has rough plumbing for a third bathroom. The main room in the basement is wired for six speaker DTS surround fully equipped in the wall and in the ceiling. It's the perfect hangout space and also lends some privacy. Outside you can either sit on the wrap around porch or enjoy your back TREX deck with PVC railings. Have parties while soaking in your 6 person hot tub, swimming in the above heated ground pool or barbequing with your built-in grill with granite countertops. Please note the 700 sq ft of finished recreation space in the basement boasts a family room, office area, workroom/utility room, storage and as noted above a roughed in full bathroom. This could have the potential to be a mother/daughter or private home office. Call us to see this beauty, it won't last long! House being sold AS IS.
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!
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 3-zone heating and AC system. 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.