The median home value in Chester, NY is $490,000.
This is
higher than
the county median home value of $389,200.
The national median home value is $338,100.
The average price of homes sold in Chester, NY is $490,000.
Approximately 73.53% of Chester homes are owned,
compared to 18.18% rented, while
8.3% are vacant.
Chester real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you see a property you’re interested in, contact a Chester real estate agent to arrange a tour today!
Courtesy: eXp Realty
888-276-0630
Welcome to 18 Academy Ave., a rare gem in the heart of the village, offered for sale for the first time in over 40 years. Built in 1900, this historic two-family home exudes character and charm, offering a unique opportunity for both homeowners and investors. The upstairs unit features a thoughtfully renovated open kitchen with stunning quartz countertops and a cozy fireplace that beautifully preserves the home's original character. With two bedrooms and a den, this unit is perfect for modern living with a touch of timeless elegance. The downstairs unit offers one bedroom with recent upgrades, providing a versatile space for rental income or personal use. Home is equipped with a new tankless water heater/boiler combo. Ideally located near public transportation, major highways, shopping, schools, hospitals, Stewart Airport, Stewart Air Force Base, wineries, and more, this property boasts unmatched convenience. Situated less than 60 miles from Midtown Manhattan, it's an ideal commuter location with incredible potential for growth. Don't miss this rare chance to own a piece of history with endless possibilities. Schedule your showing today! LotFeatures: Back Yard,
Courtesy: Howard Hanna Rand Realty
845-294-3100
Welcome to this inviting 2-bedroom, 1-bath condo nestled in the sought-after Whispering Hills community! Perfectly situated for commuters, this home combines comfort and convenience, with easy access to public transportation and proximity to major highways. Step inside to discover a well-maintained interior with an open-concept living and dining area featuring a wood burning fireplace, providing a welcoming space to relax or entertain. The kitchen boasts modern stainless steel appliances, ample cabinetry, and a functional layout, making it a delight for cooking and meal prep. Living in Whispering Hills comes with a wealth of amenities. Enjoy sunny days by the community pool, handball courts, or play a match on the tennis courts, or hit the gym for your daily workout. With a prime location, you're never far from shopping, dining, and recreation options. Appliances: Gas Range Amenities: Landscaping, Parking, Pool, HoaFeeIncludes: Pool Maintenance, Amenities: Playground, ConstructionDescription: Aluminum Siding, InteriorFeatures: Open Floorplan, ParkingFeatures: On Street,
Courtesy: Keller Williams Realty
845-928-8000
Located in the sought after Warwick Valley School District, here is your opportunity to develop pristine land on the corner of Kings Highway and Ridge Rd. in Chester, just outside the hamlet of Sugarloaf and minutes to the Village of Warwick, both offering restaurants, shops, live entertainment and more! With rolling hills and views of Sugarloaf Mountain, this untouched property offers many opportunities. Great, convenient commuter location! CurrentUses: Single Family, LotFeatures: Subdivided,
Courtesy: Keller Williams Realty
845-928-8000
OWN A PIECE OF HISTORY IN HISTORIC DOWNTOWN CHESTER. The "American House" building (this was once a hotel -- Babe Ruth was a regular guest) sits at the downtown triangle, walking distance to the Heritage Trail, as well as many businesses in this up and coming historic downtown area. TERRIFIC MIXED-USE INCOME PRODUCER (potential rent roll of close to $10,000 monthly!) with 7 units over 7,493 SF -- 3 residential apartments, and 4 office/retail units. FIRST FLOOR (all retail) -- corner unit (currently an ice cream shop), middle unit (retail space currently not in use) & end unit (large workshop area & office). SECOND FLOOR (with first floor entrances from Railroad Avenue on backside of building) -- two room office, 2 bedroom apartment, PLUS a separate 483 SF storage space, a 13x10 closet, and a 12x12 boiler room. THIRD FLOOR -- 2 bedroom apartment (with another room that could be a 3rd bedroom) and 1 bedroom apartment. All apartments are spacious and include lots of storage. SEE FLOOR PLANS IN PHOTOS FOR BREAKDOWN OF EACH FLOOR & UNITS. Beautiful detailing throughout, and incredibly functional building -- must see in person to truly appreciate! Current owners bought this property in 1998 and took it down to the studs, renovating EVERYTHING, including electric & plumbing. Lots of blood, sweat & tears have gone into getting this property in the pristine condition you'll see upon viewing. Incredibly solid & well-maintained building. New exterior paint, 1st floor hot water heater, plus lots of other recent improvements. Off-street parking for 4 cars, and plenty of street parking always available. Convenient location just off Route 17, and just 10 miles off NY State Thruway.
Courtesy: RE/MAX Benchmark Realty Group
845-341-0004
Discover your perfect commuter condo in the Whispering Hills Neighborhood of Chester! This beautiful end unit features three spacious bedrooms and two and a half baths. As you step inside, you'll find a bright and airy open living space that showcases the well maintained hardwood floors and charming fireplace, which provides a cozy atmosphere for gatherings during the cooler months. Off the side of the updated kitchen you'll discover a generously sized patio. Being an end unit, this patio offers an exceptional level of privacy creating an ideal outdoor space for summer gatherings. This unit has a roomy two-car garage attached, you'll have plenty of space for parking and storage. Enjoy the fantastic amenities within the Whispering Hills community, including a refreshing swimming pool, welcoming clubhouse and recreational facilities such as basketball/tennis courts and a playground. This condo is located in a prime location, with easy access to shops, dinning and all major highways- making it a perfect choice for commuters! Whether you're looking for a peaceful retreat or an active community atmosphere this condo has it all, don't miss your chance to make this your home. Call today for a private tour! Additional Information: ParkingFeatures:2 Car Attached, Appliances: Electric Water Heater HoaFeeIncludes: Pool Maintenance, ConstructionDescription: Vinyl Siding,
Courtesy: Keller Williams Realty
845-928-8000
Amazing opportunity to own this 6.3 Acre Lot in Monroe School District, Drilled Well and Electric on site, survey available, Level lot with panoramic views surrounded by exclusive homes. Come build your dream home only 60 Miles to NYC/Minutes to RT17/17M/I87
Courtesy: eXp Realty
888-276-0630
OPEN HOUSE - SUNDAY - NOV. 17th - 12PM-1:30PM. (Due to system issues, open houses are not going to the public websites). Spacious End Unit Duplex Townhouse featuring 3 Bedrooms, 2.5 Bathrooms and oversized 2 car garage. The 1st floor layout includes a large living room with fireplace and dining area, adjacent to the kitchen and a half bathroom. The kitchen, complete with sliding door, opens to a private patio, perfect for outdoor dining. Hardwood floors were seen. A skylight on the upper level fills the home with natural light. There are 3 well proportioned bedrooms on the upper level and a full bathroom. The Master Bedroom has an ensuite Master Bathroom. There is a tenant in place until the end of March. Additional Information: ParkingFeatures:2 Car Attached,
Courtesy: Century 21 Realty Center
845-781-8100
Gorgeous setting! One owner since the beginning! Well cared-for in a wonderful location. This peaceful and serine home has been lived-in, loved and maintained by the same family since the year it was built. The house is solid and well-built with a traditional, modest colonial floor plan. Beautiful hardwood floors throughout, fireplace, large windows, spacious rooms and more. 4 bedrooms and one bathroom upstairs and one half bathroom downstairs. Spacious closets, lots of light and a beautiful, well-established neighborhood with low-trafficked streets and friendly neighbors all add to the wonderful lifestyle this home has to offer. Some basic updates will make a world of difference. You will love the detached, spacious 2-car garage with additional area for workshop or storage. Located just a short distance to major shopping and restaurants and approx. 1hr drive to NYC. Easy NYC commute by bus or train. Don't miss. Won't last! Additional Information: HeatingFuel:Oil Above Ground Appliances: Electric Water Heater ConstructionDescription: Vinyl Siding,
Courtesy: Keller Williams Realty Group
914-713-3270
This stunning 5-bedroom, 4-bath colonial offers 3,400 square feet of living space that blends comfort with elegance. The moment you step inside, you'll be greeted by spacious rooms filled with natural light, perfect for relaxing or entertaining. The heart of the home is the large, open kitchen with modern appliances and plenty of counter space for all your cooking adventures. The living areas flow seamlessly, offering both cozy nooks and open spaces. And with five generously sized bedrooms, there's room for everyone to spread out and enjoy their own space. A second building of approx. 800 sqft could be used as a art studio, workshop, Office or anything else your imagination offers. Additional Information: HeatingFuel:Oil Above Ground, Appliances: Wine Refrigerator, FoundationDetails: Slab,
Courtesy: Keller Williams Hudson Valley
845-639-0300
Located just outside the quaint village of Sugar Loaf sits this 1835 farm house. Situated on 2.3 acres with a creek, this warm and inviting center hall colonial style house offers plenty of authentic character of yesterday, including a covered porch, mud room, 2 fireplaces and wide plank floors. There are 4 bedrooms and 2 full and 1 half baths. Yet modern day upgrades include renovated baths and kitchen granite, Whole house cellulose and foam sealing, updated 220V electric, and UV water system. Come see for yourself Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Detached, ConstructionDescription: Wood Siding,
Courtesy: eXp Realty
888-276-0630
Welcome to 11 Saddle River Rd, a beautifully updated home situated on a tranquil private road in Chester. This residence features an inviting open floor plan that seamlessly connects the modern kitchen, eat-in kitchen area, and living room, perfect for entertaining and family gatherings. With four spacious bedrooms, including an oversized master suite with a luxurious en-suite bath, this home offers comfort and relaxation. The four full baths provide ample convenience, complemented by generous closet space throughout. The kitchen boasts high-end appliances, elegant countertops, and ample storage, making it a culinary enthusiast's dream. Stunning hardwood floors flow throughout, enhancing the warm ambiance. The finished walk-out basement with an additional 1,000 sq ft space, provides versatile space ideal for a home theater, gym, or playroom, with direct access to the expansive backyard. Enjoy summer days lounging by the above-ground pool or entertaining on the newly finished deck, all within a lush, private setting. Additional highlights include a central vacuum system for effortless cleaning and a spacious property that invites outdoor activities and relaxation. This home combines comfort, style, and functionality schedule your viewing today and experience all it has to offer! Additional Information: Amenities:Soaking Tub,HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached,
Courtesy: Howard Hanna Rand Realty
845-928-9691
Ambiance surrounds you wherever you are in this wonderful home designed for living and entertaining. The two story center entry hall provides access to the entire home without undue traffic through other rooms. There are formal and informal areas throughout the first floor and tons of windows flooding the space with natural light. Serenity is the mood in the formal dining room. The large living room is set apart for formal entertainment. The efficiently designed kitchen has ample storage and counter space offering granite counter tops, tile back splash, pantry and stainless-steel appliances. The sliding glass doors bring the beauty of the outside to your chairside with access to a large deck, patio, in-ground pool and fenced in yard. The family room with fireplace flows nicely from the kitchen. For the work at home individual, there is a 1st floor professional office or can be used as a bedroom. The primary bedroom has a vaulted ceiling, two walk-in closets & primary bath with oversized soaking tub. All other bedrooms have plenty of space for sleep, storage & play. The lowest level of the home has a large recreational room with bar, full bath and an additional space. Enjoy your own private resort an in-ground pool, paver patio and surrounded with lush professional landscaping. Just minutes to major highways and public transportation. Additional Information: Amenities:Pedestal Sink,Soaking Tub,Stall Shower,HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached, ConstructionDescription: Vinyl Siding, Flooring: Carpet,
Courtesy: ESTMAX REALTY
845-980-1110
Discover a local opportunity - a spacious flat house situated on top of a large 23-acre property offering a serene and picturesque country living experience. This property presents an exciting chance for a lucrative investment, with the potential for future subdivision development. Conveniently located on Durland Road, just behind the main section of Route 17M in the Monroe Chester neighborhood, this property boasts a prime location. The house itself is in excellent condition, although the interior is currently filled with the owner's belongings, which may require some decluttering. Don't pass up the chance to own this property. There's so much to savor, from living with privacy on wooded land to enjoying a slice of heaven in this peaceful neighborhood
Courtesy: Keller Williams Realty
845-928-8000
OPPORTUNITIES ARE ENDLESS!!! Situated on 2.3 Acres is this two story commercial building boasting with expansion opportunities. This is located in the historical district of the Hamlet of Sugar Loaf / Town of Chester and situated on 500 feet of lake frontage! Not only is this property located on the direct path of ever popular Sugar Loaf Artisan Hamlet Walking Path but it is surrounded by a variety of well established businesses including the Sugar Loaf Performing Arts Center, a variety of local boutiques/shops, near several local breweries & wineries, near the Goosepond Mountain & Warwick State Park, the Castle Fun Center, LEGOLand, Mount Peter Ski Area, and just a short 15 minutes drive to major interstate highways including Interstate 84, Route 6 and Route 17. The location is key when considering to purchase this property. This property has had prior preliminary approvals for a 7,800 sqft structure which can be easily utilized for a farm-to-table restaurant, tasting room, brewery and/or wedding venue. Given this property is located in the LB-SL Zoning district, your opportunities are simply expansive. Don't delay, call now for your showing!!!
Courtesy: Keller Williams Realty
845-928-8000
Lot #2 in on the site plan in documents. Fully approved and building permit ready right in the Warwick school district! Minutes to Sugarloaf village and Warwick village. Very private! Can be sold as approved lot or a home built to suit as well.
Courtesy: Hudson Valley Realty & Busines
845-629-2223
2.5 Acres of Industrial Park zoned land. Zoning is very flexible for. variety of different uses including warehouse or office.
Courtesy: Howard Hanna Rand Realty
845-928-9691
Looking for just the right spot to build your dream home? Close to everything but also tucked away for peace and privacy. Spread out at the end of a cul de sac lies the land that can be the footprint for your new home. Make this your personal paradise or subdivide (7 lot potential) and sell as an investment. This 2.2 acre lot will be able to have municipal water and sewer. Conveniently located near to all shopping, commuting, and everything the wonderful Hudson Valley has to offer., yet tucked away for peace and privacy.
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 can truly be a mini-estate with near full privacy plus MOUNTAIN VIEWS!! FULLY ENGINEERED with NATURAL GAS, curb cuts! ... Log and Go to walk lot... Site map in photos. This is one of only two remaining lots. Some wet-lands on the property. Drive way is not shared - it will be side-by-side with the neighboring 12 acre back lot. Very commutable with easy highway access plus minutes from the vibrant towns of Sugar Loaf and Chester, NY! .. Survey Available!
Courtesy: Our House Real Estate Group
845-705-8093
Lovely 1-Acre lot w/MOUNTAIN VIEWS in a beautiful newly built SUB-DIVISION. Build out this nearly completely built lovely sub-division, curb-cuts, paved road sloping lot perfect for a WALK-OUT BASEMENT and DECKS FOR BEAUTIFUL VIEWS ... FULLY APPROVED LOT, ESTABLISHED NEIGHBORHOOD, VERY COMMUTABLE location! Close to the vibrant shopping, restaurants, nightlife, shows/events at Sugar Loaf and Chester ...... ONLY 2 LOTS REMAINING!
Courtesy: Timothy W. Kramer
845-325-3472
BACK ON MARKET! over 7000 finished square feet surroundeed by 400 acres of state owned land! Total privacy with this spectacular home sits in the middle of over 3 mature acres which includes a beautiful natural waterfall. Grand entryway with cathedral ceilings and marble floors. Spacious formal living room and dining room - Extraordinary chefs kitchen complete with double oven, gas range and griddle bound by custom stone, tile, and granite. HUGE 2 tiered kitchen island with prep sink, pantry, and beautiful butlers area. Breathtaking family room embellished with grand floor to ceiling stone fireplace. Outdoor stone kitchen & bar area. Extensive and private stamped concrete patio with hot tub surrounded by custom stonework. Enormous well manicured backyard accompanied by a swing set, and oversized shed. Master bedroom suite offers a fireplace flanked by stone, a private porch, and large master bathroom- steam shower, jacuzzi tub and vanity. Finished basement/ Recreational area includes a full gym and wet bar. This over 7,000 sq ft home includes 5 bedrooms, 4 full baths, 4 fireplaces(3 gas,1 wood burning) 3 car custom garage, and enormous attic. Gorgeous radiant hardwood floors and astounding craftsmanship throughout make this home an absolute must see! Don't miss out on this excellent opportunity! 9 heat zones including radiant heat together with spray foam make this house very efficient for such a large house. Electric has been run for a gate at the bottom of the driveway if desired. Speakers in each room provide whole house music controlled by a bluetooth receiver. Too many options to list. Must see.
Courtesy: Century 21 Realty Center
845-781-8100
Welcome to this beautiful TURNKY 4 bedroom colonial home nestled by Walton Lake! This home presents a perfect balance between classic charm and modern comfort. You will find 4 generously sized bedrooms offering privacy, comfort and lots of natural light. The primary bedroom offers 2 spacious closets and a large bathroom suite featuring double vanity sinks, a walk-in shower and a soaking tub. Enjoy the large basement that has a full bathroom for family gatherings, exercise area or for additional storage. Don't miss your chance to own this wonderful colonial home! WOW! Seller is willing to leave all furniture for interested buyers! Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached,
Courtesy: eXp Realty
888-276-0630
Discover the enchanting tranquility of Rock Ridge Estates, where this magnificent Colonial home awaits, perched gracefully on a scenic knoll. From its vantage point, you're treated to awe-inspiring views of the sprawling valley and majestic Sugar Loaf Mountain a picture-perfect backdrop for serene living. Spanning over 6.1 lush acres, this property is a haven for outdoor enthusiasts. With dense, verdant woods ideal for hiking, nature walks, and ATV riding, adventure is always at your doorstep. The home itself boasts an expansive layout featuring four bedrooms and 2.5 bathrooms, blending modern amenities with timeless rustic charm. Step up to the inviting rocking chair front porch or unwind on the deck, where panoramic vistas offer a constant reminder of nature's grandeur. Inside, the home radiates warmth and comfort. The spacious family room, with direct access to the porch, and the cozy living room with its charming brick-faced fireplace, provide perfect settings for relaxation and enjoyable gatherings. Culinary delights await in the kitchen, highlighted by a cherry-toned island with an integrated wet bar, and a quaint breakfast bay with built-in bench seating, creating a warm space for morning coffee and intimate meals. A versatile multi-purpose room equipped with custom stainless steel cabinets adds flexibility to this already impressive home. Retire to the luxurious master suite, complete with double closets, offering a private retreat after a day's adventures. Additional conveniences include an "EV" Electric Vehicle Charging Station in the garage, enhancing this home's modern appeal. Located just minutes from the vibrant town of Chester, you'll enjoy easy access to shopping, dining, and entertainment, all while relishing the peace and beauty of country living. This stunning home is more than just a residence it's a gateway to a lifestyle of tranquility, comfort, and adventure. Don't let this dream escape; schedule your viewing today and step into your future. Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached, ConstructionDescription: Vinyl Siding, FoundationDetails: Slab,
Courtesy: Keller Williams Realty
845-928-8000
Welcome to 1807 Whispering Hills, Chester Your Dream Home Awaits! This 2 bedroom 1.5 bathroom townhome is located in the sought-after Whispering Hills community. Updates include: kitchen with stainless steel appliances, bathroom, hardwood floors throughout, washer/dryer, and new garage door (July 2024) with one-year warranty. Patio furniture included. HOA fee includes trash collection, lawn maintenance and snow removal. The community has two pools, basketball courts, tennis courts, gym, dog run, and playgrounds.
Courtesy: Keller Williams Hudson Valley
845-610-6065
This charming three-bedroom, two-bath townhouse is nestled in the Whispering Hills community. Featuring a cozy fireplace in the living room, this home offers a warm and inviting atmosphere perfect for comfortable living. The unit comes equipped with a washer and dryer, adding to your convenience. Dishwasher updated in 2022. A/C unit replaced in 2020. Dyer's vent chimney and Heating system serviced done in very year. The property also includes an attached one-car garage, providing additional storage space. Whispering Hills is a sought-after community known for it's amenities, including a Clubhouse, Pool. Basketball Court, Tennis Court, Play Ground. Its location offers easy access to shopping centers, major highways, and a commuter bus service to NYC, making it ideal for frequent travelers. Discover a hidden gem in this great location. Don't let this opportunity pass you by!" Please note that the photos were taken before the current tenants moved in.
Courtesy: eXp Realty
888-276-0630
Discover Easy Living at 1107 Whispering Hills! Embrace the simplicity and elegance of this updated townhouse-style condo, where modern comfort meets convenience. Featuring an updated kitchen and sleek bathrooms renovated in 2020, this 2-bed, 1.5-bath home is designed for relaxation and ease. With a spacious 2-car garage, snow removal right to your door included in the HOA, and just 55 minutes from NYC with nearby bus access, it's the perfect blend of suburban tranquility and city connectivity. Enjoy leisure at its best with community pools, tennis, and basketball courts, all while being moments away from shopping. 1107 Whispering Hills isn't just a place to live; it's your key to a carefree, vibrant lifestyle. Welcome to your dream home. Additional Information: ParkingFeatures:2 Car Attached, ConstructionDescription: Aluminum Siding,
