The median home value in Chester, NY is $525,500.
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 $525,500.
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: Keller Williams Valley Realty
201-391-2500
Monroe's magnificent mini mansion awaits its newest owner! This home has everything you have been waiting for in the perfect place. Walk into this 5-bedroom, 3-bath home with a gorgeous double-height entrance and palladium window and be greeted by your double-sided luxury stairs. Before going up, you will be amazed by the large cook's kitchen with all top-of-the-line stainless appliances, a huge formal dining room, a family room with a fireplace, and plenty of closets and storage. All of this leads to a huge deck and breathtaking heated inground saltwater pool! Upstairs, you will find plenty of places to sleep as well as enjoy guests, a yoga studio equipt with heated hot panels throughout, or even a home office! So many possibilities await you! In addition, this home has an amazing barn and garage for your auto, mechanic, or handyman enthusiast! It includes an auto lift, a kitchen, AC, and all updated electrical. The home has gorgeous and plentiful landscaping full of beautiful pear trees, gardening, and so much to sit back and enjoy for four seasons long! Monroe-Woodbury at its best, and the time is NOW!
Courtesy: Keller Williams Hudson Valley
845-610-6065
Nestled on 2.8 acres of lush, mature landscaping that borders the serene Goosepond Mountain State Park, this custom-designed contemporary ranch showcases a timeless blend of materials, with stone and brick construction lending both character and durability. Crafted by its original owners with meticulous attention to detail, the home offers a harmonious connection to its natural surroundings. A fenced yard, a shed with electric, and a spacious deck invite you to embrace outdoor living in this private haven. Step inside to an open-concept living and dining area where soaring windows flood the space with natural light and frame breathtaking views. At the heart of the main level is a striking double-sided, floor-to-ceiling stone fireplace, creating a warm and inviting centerpiece. On the lower level, a custom brick fireplace adds character and charm to the finished walk-out basement. Just off the main living area is a unique space with tongue-and-groove vaulted ceilings and skylights—perfectly suited for a larger dining area, a workspace, or a creative studio. The main home features four generously sized bedrooms, a finished basement, and a two-car garage, offering both comfort and functionality. A legal one-bedroom apartment with its own kitchen, living area, and laundry hookups adds exceptional flexibility, whether for generating additional income or hosting guests. Located just 60 miles from NYC and close to major highways, mass transit, shops, and restaurants, this home is as convenient as it is serene. With every detail carefully considered, every view perfectly framed, and every space thoughtfully designed, it offers a lifestyle that is both inspiring and tranquil.
Courtesy: Keller Williams Realty
845-928-8000
WELCOME TO WHISPERING HILLS CONDOMINIMUM COMMUNITY!!! Check out this 3 Bedroom, 2.5 Bathroom Condominium nestled in the Village of Chester and in the Chester School District. This Condo is located a mile from the Village of Chester featuring a variety of Village amenities including local restaurants, shopping centers, medical offices, banking services, home improvement stores, close to attractions including The Castle Fun Center, LEGOland Theme Park and close to most major highways including Interstate 17, Route 6 and Route 17M. The location is just the start, checkout the amenities this home has to offer starting with the kitchen with a plethora of cabinetry, stainless steel appliances, granite counter tops, ceramic tile flooring, sliding glass doors leading to the patio area, dining area, laminate hardwood flooring throughout the home, half bathroom and laundry room/utility room. 2nd floor features the primary bedroom with en-suite full bathroom w/shower stall and two additional bedrooms w/shared full bathroom. Exterior features two car attached garage. Community features tennis courts, club house with an inground pool, playground area and guest parking is available. Don't pass this opportunity by, call now for your showing!!!
Courtesy: Howard Hanna Rand Realty
845-294-3100
Welcome to this beautiful raised ranch that has been lovingly maintained and is ready for its new owners! This home offers 3 bedrooms and 1.5 bathrooms. The living room/dining room offers lots of natural light with vaulted exposed beam ceilings that lead out to a two-tier deck! Nestled in the highly desirable Warwick School District, this home has not been on the market in decades, offering a rare opportunity for you to make it your own. Newly finished hardwood floors throughout the upper level offers a warm and inviting atmosphere. Freshly updated vinyl floors on the lower level are perfect for a variety of uses such as a family room, home office, or entertaining space. A huge bonus mudroom for all your storage needs is also on the lower level! Enjoy privacy and space for pets, play, and outdoor entertaining with a large, fenced-in yard. Easy access to local amenities in Sugar Loaf, Chester and Warwick, shopping, and parks. From here you can easily head over to Route 17 and get to Woodbury Commons, Legoland and park and ride to NYC. This home has been cherished by its owners for decades and is ready for a new chapter. Don't miss your chance to see this fantastic property!
Courtesy: Point Realty USA
845-604-9400
Unique Opportunity BRAND NEW WAREHOUSE in CHESTER INDUSTRIAL PARK!!! This state-of-the-art warehouse offers an expansive space perfect for a variety of industrial or commercial uses. With its towering 32-foot ceilings and over 31,000 square feet of space, the possibilities are endless. The construction is almost complete, providing a unique opportunity for the buyer to tailor the final touches to their specific needs. Don’t miss out on this rare chance to own a customizable, brand-new facility in a thriving industrial hub. Contact us today to learn more or schedule a viewing!
Courtesy: Howard Hanna Rand Realty
845-294-3100
Lovely three-bedroom, two-bath, townhouse with attached one car garage in the sought-after Whispering Hills Community of Chester. This second floor end unit has an inviting woodburning fireplace & vaulted ceiling. The sliding door off the living rm leads to a private deck. The pretty navy & light blue kitchen is adjacent to the dining area & includes granite countertops, black appliances & pantry. The spacious primary bedrm has a walk-in closet organizer & tastefully updated bathrm with dual sinks & tiled shower area. The two additional bedrooms are well proportioned & the main hall bath has been updated. Private laundry with washer & dryer included. Newer vinyl windows, Trane central air, gas heating system & public services. Bonus - inquire about the Community Solar Array option! Amenities include: outdoor pool, fitness center, tennis & basketball courts, playground, & rec center. Commuter bus stops in the complex to NYC, plus easy access to shops, dining & all major highways.
Courtesy: Keller Williams Realty
845-928-8000
Discover your sanctuary in the highly coveted Warwick Valley School District! Nestled on nearly 2 breathtaking acres, this charming home offers the perfect blend of privacy and modern comfort. With stunning views of Sugar Loaf Mountain, you’ll feel surrounded by nature while enjoying the convenience of one-level living. Step inside to an inviting open floor plan, ideal for entertaining family and friends. The spacious living and dining areas bathe in natural light, seamlessly connecting to a delightful three-season screened sunroom—your personal retreat for morning coffee or evening gatherings. This lovely residence features 2 generously sized bedrooms and 2 full baths, along with a large laundry room to make daily life a breeze. With recent updates including new flooring, fresh paint, and modern appliances throughout, you can move in with ease and enjoy all the contemporary amenities you desire. Outside, the beautifully landscaped grounds are adorned with mature oak trees, creating a serene backdrop for your everyday life. Situated well off the road, you’ll relish the tranquility and privacy this home offers. Plus, you're just a short drive from the charming Village of Warwick and major highways such as 17, I87, and Palisades Parkway, making commuting and enjoying local amenities a breeze. Don’t miss this rare opportunity to own a piece of paradise in a sought-after community. Schedule your private tour today and make this dream home your reality!
Courtesy: HomeSmart Homes & Estates
914-236-5500
Welcome to a stunning retreat at 142 Laroe Rd, Chester, NY 10918—, offering a harmonious blend of elegance, space, and functionality. Covering a generous floor size of 3,385 square feet on an expansive lot of 69,696 square feet, this magnificent property promises spacious living, comfort, and captivating beauty both indoors and outdoors. This five-bedroom, three-bathroom masterpiece is designed to impress, featuring a myriad of rooms perfect for every aspect of modern living. The open-plan kitchen flows seamlessly into the inviting breakfast nook and the spacious dining room, offering the perfect backdrop for both intimate family meals and grand entertaining. The kitchen is equipped with all the essentials and more, providing a practical yet stylish space for culinary adventures. As you explore this luxurious home, discover the many dedicated spaces that accommodate varied lifestyles: a family room, den, and entertainment room provide ample relaxation and recreation options, while the loft, home office, and utility room ensure functionality and convenience. For quieter moments, the cozy attic and kid's playroom are delightful havens. A master suite with an indulgent master bathroom exudes tranquility and privacy, promising restful nights and rejuvenating mornings. The home's allure continues outdoors, where an expansive yard beckons with its lush landscape. Dive into the refreshing pool, entertain guests in the barbecue area, or unwind in the hot tub located on the serene patio. The dedicated shed adds storage solutions, while the two-car garage and ample driveway accommodate vehicles with ease. This home is more than just a dwelling—it's an opportunity to create cherished memories in a place where elegance meets practicality.
Courtesy: Keller Williams Realty
845-928-8000
Welcome to 76 Restdale Road, an exquisitely updated 4-bedroom, 2.5-bath home nestled on 1.4 private acres in the highly desirable town of Chester, NY. Located within the award-winning Warwick Valley Central School District, this property offers an ideal combination of modern amenities and serene country living. As you approach the home, you're greeted by a charming wrap-around front porch, perfect for relaxing and enjoying the peaceful surroundings. A beautiful koi pond at the front entrance adds a touch of tranquility and elegance, setting the tone for the rest of the home. Step inside to find gleaming hardwood floors that flow throughout the main living areas. The spacious living room, centered around a cozy fireplace, provides an inviting space for relaxation and warmth on chilly evenings. The heart of the home is the stunning renovated kitchen, featuring top-of-the-line Wolf appliances, a Sub-Zero fridge, custom cabinetry, and elegant soapstone countertops—ideal for both everyday cooking and entertaining. The kitchen seamlessly flows into the dining area, offering the perfect space for family meals and gatherings. A wet bar enhances the entertaining options, offering a stylish spot to mix drinks or serve guests. Upstairs, both full bathrooms were beautifully renovated in 2022, combining modern finishes and luxurious details. The four spacious bedrooms provide ample closet space and plenty of natural light, creating a comfortable retreat for the entire family. Step outside to discover your own private oasis. The inground pool—recently updated with a new liner and pump in 2022—is the perfect spot to unwind and enjoy the warmer months. The expansive backyard offers room for outdoor activities, gardening, or simply enjoying the natural beauty that surrounds you. A large back deck provides additional space for al fresco dining, entertaining, or simply relaxing and taking in the views of the picturesque grounds. The property is an entertainer’s dream, with multiple areas designed for enjoying both quiet moments and lively gatherings. Additional highlights include a two-car garage, a generator transfer switch , and a large unfinished basement that offers ample storage space with future potential. With 1.4 acres of land, this home offers the perfect balance of privacy and convenience. Enjoy the peacefulness of country living while being just a short distance from local amenities, schools, and parks. Don’t miss out on the opportunity to make this extraordinary property your own—schedule a showing today and see all that 76 Restdale Road has to offer!
Courtesy: RE/MAX Benchmark Realty Group
845-341-0004
Welcome to 16 Kerner Drive nestled in the village of Chester! This single-level living space spans just over 1,200 square feet and features three bedrooms and a full bath, perfect for those seeking a comfortable and convenient lifestyle. The heart of this home is the formal living room that features a large bay window, filling the space with tons of natural light. Adjacent to the living room is the dinning room, ideal for hosting gatherings! Off the dinning room, you will find sliding doors leading to the enclosed screened porch, the perfect spot for relaxing and enjoying the outdoors! This property boast of a walk-out basement offering endless potential for customization to suit your needs! The attached garage provides easy access to the home, while the detached two-car heated garage is a fantastic bonus for any car enthusiast or those needing extra workspace. This home offers a wonderful canvas for your personal touch, allowing you to enhance its character and make it truly your own. With its solid foundation and inviting layout, the possibilities are endless! Don't miss out on the opportunity to make this lovely ranch-style home yours!!
Courtesy: eXp Realty
888-276-0630
***Welcome Home to this great commuter location in the desirable Valley View subdivision*** The open floor plan seamlessly connects the living, dining, and kitchen areas, providing the ideal setting for gatherings and entertaining. Every room exudes charm and sophistication. Just moments from home you'll find easy access to transportation, ensuring a smooth commute to work or outings. Additionally, Chester's vibrant community offers a variety of entertainment options, including dining, shopping, and recreational activities. This Colonial home in Chester, New York, is more than just a residence; it's a lifestyle. This property embodies luxury living at its finest.This magnificent colonial has gorgeous sunset views from the Primary Bedroom and Living Room. The entrance opens up to a two-story foyer, an The first floor which also provides a private office, spacious living room, formal dining room and a open concept kitchen with stainless steel appliances that leads to your large family room with a wood burning fireplace. Upstairs boasts 4 bedrooms including an over size primary bedroom suite, skylights in the Master bath and a large walk-in close with 2 additional closets. ***Contact us today to arrange a private viewing and experience the elegance and comfort this property offers. Your new chapter begins here!***Contact us for more information.
Courtesy: HomeSmart Homes & Estates
845-547-0005
Welcome to this beautiful and cozy 2 bedrooms condo with 1.5 bathrooms and 2 car garages in a beautiful neighborhood of Whispering Hills. The 1st level is wonderfully laid out with a great size living room and its fireplace to a dining room with new engineer wood floor throughout the first floor. Fully renovated kitchen with new cabinets, granite countertops & backsplash and great stainless appliances. The 2nd floor is offering a vaulted ceiling and spacious mast bedroom with Jack and Jill bathroom and another great size bedroom. It is a very well maintained home with newer roof done by the HOA and new hot water heater. The complex has club houses, 2 inground pools, play ground and lots of parking for visitors. It is located in the center of Orange County NY in the Hudson Valley with so much outdoor activities for the entire year. It's near Lego Land, Woodbury Outlets, Mt Peter Ski in Warwick, apple orchards, wineries and much more summer and winter attractions. It is minutes to shopping, restaurants and it is great to NYC commuters since the buses is going thru the complex.
Courtesy: ARC Realty 1 in Sales
845-783-5145
WHISPERING HILLS! LOW TAXES! Cul-de-sac Location! 2 Bedrooms! 1 1 /2 Bathrooms! 2 Car Garage! Master Bedroom with Large Walk in Closet & Cathedral Ceiling! Kitchen with Granite Counter Tops! Living Room with Fireplace! Dining Room! Freshly Painted! Central Air! Patio! Perfect Commuter Location! Walk to NYC Bus & Shopping! Close to Major Highways! Country Club Living! Pools! Clubhouses! Tennis! Basketball! Tot Lot! Dog Walk! This is a Must See!!
Courtesy: Sage Realty Center LLC
845-299-7243
Welcome to this stunning home located in the heart of Chester NY. Completely renovated, Spacious bedrooms, full baths, plenty of closets, Living/Dining room, Office room, bright kitchen, granite countertops, dishwasher oven and refrigerator, Situated on a relaxing property, while enjoying the peaceful views throughout, in addition to benefiting from a healthy living environment, Close to major roadways, shopping, bus and train access to NYC as well. Come take a look at it and you will certainly fall in love!
Courtesy: Keller Williams Hudson Valley
845-610-6065
Discover the perfect blend of versatility and charm with this exceptional property featuring two beautifully maintained units. The main house offers three levels of comfortable living, including four bedrooms, three baths, and a spacious kitchen ideal for gathering and entertaining. The thoughtfully renovated barn boasts a cozy one-bedroom, one-bath layout with modern touches that make it an inviting retreat. Whether you choose to live in one unit while renting out the other or maximize your investment potential by renting both, this property opens the door to endless opportunities. Make it yours today!
Courtesy: Keller Williams Realty
845-928-8000
This stunning 4-bedroom, 2.5-bathroom home in Sugar Loaf, NY, offers 2822 sq. ft. of spacious living, nestled within the highly sought-after Warwick School District. The home features a grand fireplace in the great room, a chef’s kitchen, and a walk-out basement with office space. Enjoy breathtaking views of Creamery Pond from the property, creating a tranquil setting for both indoor and outdoor living. Perfectly situated for commuters, with easy access to major highways and transportation, this home offers the ideal blend of luxury, comfort, and convenience, all while being close to local shops and outdoor activities.
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!
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,
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: 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,
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,
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