Chester NY Real Estate & Homes for Sale

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Beds:
5
Baths:
3.00
Sq.Ft.:
3,200
Status:
NEW LISTING
MLS#:
1020076
Type:
Single Family
Subdivision:
Greens At Chester
Lot size:
0.08 Acres
Year built:
2022
A broker reciprocity listing Courtesy: MK Realty Inc 845-782-0205
View additional info

ADDITIONAL INFORMATION

Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new colonial-style residence invites you in with 12 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail is thoughtfully upgraded for comfort and style. Enjoy the privacy of a modern retreat in a warm, vibrant community—the perfect setting to make new memories.

Beds:
5
Baths:
3.00
Sq.Ft.:
27,000
Status:
NEW LISTING
MLS#:
1020128
Type:
Single Family
Subdivision:
Greens At Chester
Lot size:
0.08 Acres
Year built:
2022
A broker reciprocity listing Courtesy: MK Realty Inc 845-782-0205
View additional info

ADDITIONAL INFORMATION

Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 9 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail is thoughtfully upgraded for comfort and style. Enjoy the privacy of a modern retreat in a warm, vibrant community—the perfect setting to make new memories.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,100
Status:
NEW LISTING
MLS#:
1020165
Type:
Single Family
Lot size:
3 Acres
Year built:
1987
A broker reciprocity listing Courtesy: Serhant LLC 646-480-7665
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ADDITIONAL INFORMATION

Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgettable place to call home. Inside, the heart of the home is anchored by a stunning double sided fireplace that effortlessly connects the main living areas, creating warmth, character, and an inviting atmosphere for both everyday living and entertaining. Sunlight pours into the beautiful sunroom, offering the perfect place to enjoy your morning coffee, unwind with a good book, or simply take in the tranquil views of the property throughout every season. Step outside and discover the true highlight of this remarkable property. Designed with entertaining in mind, the backyard is a private oasis featuring a sparkling inground pool, beautifully integrated outdoor living spaces, a custom built fire pit, and built in seating that invites family and friends to gather long after the sun goes down. Whether you're hosting summer pool parties, enjoying crisp fall evenings by the fire, or simply relaxing in your own backyard retreat, this outdoor space delivers an exceptional lifestyle year round. Set on over three private acres, the property offers the perfect balance of open space and privacy. There is plenty of room to explore, play, garden, or simply enjoy the serenity of nature, all while being just minutes from the conveniences of the Hudson Valley. Offering 4 bedrooms, inviting living spaces, and an outdoor setting that feels like your own private resort, this is more than just a home. It is a place where memories are made, weekends are enjoyed, and every season brings something special.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,086
Status:
NEW LISTING
MLS#:
1019548
Type:
Condo
Year built:
1984
A broker reciprocity listing Courtesy: Howard Hanna Rand Realty 845-928-9691
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ADDITIONAL INFORMATION

Step into this gorgeous Townhouse.Upon entering you’ll be welcomed by a perfect floor plan. The inviting living room features wooden floors, a cozy fireplace, and windows. The stylish kitchen has a functional layout and is outfitted with stainless steel appliances and granite countertops. The master-bedroom offers a modern feel and a walk in closet. Enjoy the amenity centers. Stop dreaming and start living, come and take a look today! The Condo charges $475 , HOA $250

Beds:
3
Baths:
1.00
Sq.Ft.:
2,016
Status:
Active
MLS#:
1016060
Type:
Single Family
Lot size:
0.69 Acres
Year built:
1800
A broker reciprocity listing Courtesy: Ellis Sotheby's Intl Realty 845-353-4250
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ADDITIONAL INFORMATION

We are proud to introduce this cornerstone property, located within what was once a thriving enclave of artists. The same owner since 1946, this home and studio are part of a small collection of historic properties that helped define the character of the area. Now, an extraordinary opportunity awaits for the next steward to write the next chapter of this remarkable property. Originally built circa 1800, the home sits quietly within the landscape, its history unfolding through generations of thoughtful additions. Among them was a former general store, where horse-drawn carriages once stopped for dry goods and daily provisions, while the village blacksmith worked just across the way. From the road, passersby may never suspect what lies beyond. Behind its unassuming facade is a private and enchanting oasis, complete with expansive studio space that inspires creativity and retreat. The home itself is rich with period details that have been lovingly preserved through time. Wide-plank floors, beautifully patinated doors, burnished staircase railings, classic fireplaces, and a hidden back staircase all contribute to its authentic historic charm. An elevator was added for convenience to the 2nd floor. The studio still features the original general store counter and shelving, offering a rare connection to the property's past. The generous space lends itself to a wide range of creative pursuits, with a private retreat area tucked behind. Stone walls frame an intimate cottage garden, while the existing potting shed offers potential for expansion into a garage or workshop. This is more than a home—it's a piece of local history waiting to be reimagined. This weekend destination is set amid the rolling hills of Orange County, this property offers easy access to the Hudson Valley's most sought-after destinations, including Storm King Art Center, the artisan community of Sugar Loaf Arts and Crafts Village, wineries, orchards, hiking trails, and the outdoor recreation that has made the region a favored escape for New York City residents seeking space, creativity, and a connection to nature.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,236
Status:
Active
MLS#:
1015381
Type:
Single Family
Lot size:
3.7 Acres
Year built:
2019
A broker reciprocity listing Courtesy: KW Hudson Valley United 845-610-6065
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ADDITIONAL INFORMATION

Welcome to 24 Boville Court, a beautifully situated home tucked away on a quiet cul-de-sac in the desirable Town of Chester. Offering a wonderful blend of comfort, privacy, and convenience, this property is the perfect place to call home. Step inside to discover bright and inviting living spaces, generously sized rooms, and a functional floor plan designed for both everyday living and entertaining. Natural light fills the home, creating a warm and welcoming atmosphere throughout. Outside, enjoy a peaceful setting with ample space for relaxing, gardening, or hosting gatherings. The property's location on a cul-de-sac provides added privacy while maintaining easy access to local amenities and major commuter routes. Conveniently located near shopping, dining, parks, schools, and the charming Village of Chester, this home also offers proximity to hiking trails, wineries, breweries and farm markets, and all the recreational opportunities the Hudson Valley has to offer. Whether you're searching for a primary residence, weekend retreat, or investment opportunity, 24 Boville Court presents a fantastic chance to enjoy life in one of Orange County's most sought-after communities. Schedule your private showing today and discover everything this wonderful property has to offer. All the the light fixtures will also be staying with the home along with a Lorex Hard wired 6 camera Outdoor Security System. Custom shades in all the windows and a Reverse Osmosis Water System in the kitchen & a soft water system for the house. The lot is the end corner lot that goes all the way up to RT 94

Beds:
3
Baths:
3.00
Sq.Ft.:
1,331
Status:
Active
MLS#:
1016415
Type:
Condo
Subdivision:
Whispering Hills
Year built:
1984
A broker reciprocity listing Courtesy: Keller Williams Realty 845-928-8000
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ADDITIONAL INFORMATION

Welcome to 2703 Whispering Hills in Chester, NY — a beautifully updated home that stands out from the rest. This well-maintained unit features numerous recent improvements, including new windows, a new garage door, and a new hot water heater, providing peace of mind for years to come. The central air conditioning system is approximately five years old and keeps the home comfortable throughout the seasons. Inside, you'll immediately appreciate the stylish luxury vinyl plank flooring throughout the main level, offering both durability and modern appeal. The home is further enhanced by elegant wainscoting and custom trim work that adds character, sophistication, and a level of craftsmanship rarely found in comparable units. These thoughtful upgrades create a warm, inviting atmosphere that truly sets this property apart. Step outside to your private patio and enjoy the amazing views, creating the perfect setting for morning coffee, outdoor dining, or simply relaxing and taking in the scenery. The combination of indoor upgrades and exceptional outdoor space makes this home truly special. Located in the desirable Whispering Hills community, this move-in-ready home combines comfort, style, and value in one exceptional package.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,697
Status:
Active
MLS#:
1012919
Type:
Single Family
Lot size:
0.42 Acres
Year built:
2004
A broker reciprocity listing Courtesy: eXp Realty 888-276-0630
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ADDITIONAL INFORMATION

Welcome to 19 Grand View Terrace in Chester, NY, an impressive Colonial offering approximately 4,697 square feet, five bedrooms, and four full bathrooms. Set on approximately 0.42 acres, this expansive Orange County residence provides the space, comfort, and flexibility needed for everyday living, entertaining, working from home, and hosting guests. The generous interior features multiple living areas, well-proportioned bedrooms, central air conditioning, and a versatile floor plan designed to accommodate a variety of lifestyle needs. At the heart of the home is a chef’s kitchen equipped with professional-grade appliances, offering an exceptional setting for preparing meals, entertaining guests, and gathering with family and friends. The finished lower level provides additional flexible space for a recreation room, media area, home gym, private office, or guest accommodations. An attached garage adds convenient parking and storage. Step outside and enjoy an inviting outdoor setting highlighted by an outdoor fireplace, creating the perfect atmosphere for relaxing evenings, seasonal gatherings, and memorable moments under the Hudson Valley sky. Located within the Chester School District, the property offers convenient access to local shopping, dining, recreation, commuter routes, and the many attractions of Orange County and the Hudson Valley. Buyers searching for a spacious five-bedroom home in Chester, NY, with a chef’s kitchen, professional-grade appliances, flexible living space, a finished lower level, and exceptional indoor-outdoor entertaining features will appreciate everything this property has to offer. 19 Grand View Terrace combines generous living space, elevated amenities, and a desirable Chester location—an exceptional opportunity to create the home and lifestyle you have been searching for.

Beds:
4
Baths:
4.00
Sq.Ft.:
4,281
Status:
Active
MLS#:
1010585
Type:
Single Family
Lot size:
2.3 Acres
Year built:
2003
A broker reciprocity listing Courtesy: Howard Hanna Rand Realty 845-294-3100
View additional info

ADDITIONAL INFORMATION

Welcome to an unparalleled expression of luxury living in the Town of Chester. Built in 2003, this custom-built Cape May/Colonial estate designed by award winning architect Larry Belk estate spans 4,281 square feet of meticulously designed living space, masterfully balancing grand entertaining spaces with intimate everyday comfort. From the moment you arrive, exceptional craftsmanship is on display—from the solid wood doors and dual staircases to the premium radiant-heated floors sweeping across the entire main level. The inviting foyer seamlessly transitions into the formal living and dining rooms, both framed by dramatic floor-to-ceiling windows, intricate crown molding, and striking red oak flooring with Mahogany inlays. Both formal spaces open directly to an expansive bluestone patio, offering an effortless indoor-outdoor lifestyle. At the heart of the home is a true culinary enthusiast’s kitchen, outfitted with oversized granite countertops, custom cabinetry, and a table-height center island. Immediately adjacent, a sunken family room anchored by a rustic wood-burning fireplace serves as the perfect gathering hub, featuring French doors that lead to a covered bluestone patio and a private fire pit area. Retreat to the main-level primary suite—a serene sanctuary complete with gas fireplace and French doors opening to a private, wrap around covered Trex deck. The spa-like primary bath boasts a vintage-inspired cast iron clawfoot tub, a walk-in shower, and dual vanities, all complemented by a massive walk-in closet. A dedicated laundry room completes the main level. Upstairs, discover a versatile bonus loft accessed via a spiral staircase, a full walk-up attic, and three generously sized bedrooms—two of which feature private en-suite baths and walk-in closets. The lower level is an enthusiast’s dream. Beyond vast storage capabilities, this floor houses a dedicated wine-making room and provides direct access to an extraordinary, pristine multi-car garage featuring professional epoxy flooring. A true masterpiece of design, utility, and sophistication. Enjoy effortless travel with immediate access to Route 17 (I-86) and the NYS Thruway, while mass transit options like the Chester Park & Ride and the Harriman Train Station make commuting a breeze. Located just 60 miles from NYC, you can enjoy the peace of the suburbs and be in the city in just over an hour. Unbeatable location for entertainment, dining, and shopping! You are 10 miles from the world-famous Woodbury Common Premium Outlets. Explore Chester’s vibrant local food scene, steps from local restaurants, craft breweries, and renowned local wineries. Outdoor enthusiasts will love the proximity to the scenic Orange Heritage Trail. Exceptional location, maximum convenience, and a perfect place to call home!

Beds:
3
Baths:
1.00
Sq.Ft.:
1,561
Status:
Active
MLS#:
1011551
Type:
Single Family
Lot size:
0.37 Acres
Year built:
1952
A broker reciprocity listing Courtesy: River Realty Services, Inc. 845-564-2800
View additional info

ADDITIONAL INFORMATION

One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space. Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk to the village!

Beds:
4
Baths:
3.00
Sq.Ft.:
3,100
Status:
Active
MLS#:
1010959
Type:
Single Family
Subdivision:
Sugar Loaf Commons
Lot size:
0.33 Acres
Year built:
1997
A broker reciprocity listing Courtesy: Howard Hanna Rand Realty 845-928-9691
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ADDITIONAL INFORMATION

Welcome to this elegant colonial in the highly regarded Warwick School District, where timeless charm meets modern comfort. Relax on the inviting front porch while enjoying your morning coffee and breathtaking mountain views. Inside, spacious sun-filled rooms and hardwood flooring throughout the formal living and dining areas create a warm, welcoming atmosphere. A dramatic two-story foyer sets the tone for the home's open and airy feel. The generously sized living room with fireplace and dining room provide the perfect setting for entertaining and special gatherings. The chef’s kitchen features quartz countertops, a large center island, stainless steel appliances, a pantry and a bright breakfast nook. French door leads to an expansive composite deck, making indoor-outdoor entertaining effortless during the warmer months. The adjacent family room, with abundant natural light, offers the perfect space for relaxing and everyday living. Upstairs, the luxurious primary suite serves as a private retreat, featuring a spa-inspired bath with a whirlpool tub, separate shower and walk-in closet. Three additional bedrooms and a shared hall bath complete the upper level. The finished lower level provides versatile living space ideal for a recreation room, playroom, home gym or media room. Ideally located within walking distance to the charming village of Sugar Loaf's shops and restaurants, and just minutes from major highways and NYC bus service. This exceptional home offers easy access to the area's best amenities, including wineries, breweries, hiking trails, skiing, and more.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,656
Status:
Active
MLS#:
1011165
Type:
Single Family
Lot size:
7.1 Acres
Year built:
1993
A broker reciprocity listing Courtesy: eRealty Advisors, Inc 914-712-6330
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ADDITIONAL INFORMATION

Escape to your own private retreat at 49 Stone Mountain Trail. Tucked away on more than 7 acres with mountain views, this contemporary home delivers the perfect balance of comfort, space, and outdoor enjoyment. Imagine mornings filled with sunlight streaming through oversized windows, evenings gathered around the stone fireplace, and summers spent relaxing by the in-ground pool surrounded by nature. The soaring great room creates a dramatic first impression, while the beautifully updated kitchen serves as the heart of the home with its oversized island and bright, modern finishes. Outside, the expansive grounds provide endless possibilities—from entertaining and recreation to simply enjoying the peaceful surroundings. With 4 bedrooms, 2.5 baths, and over 3,600 square feet of living space, this property offers room to spread out while enjoying the privacy and beauty of its remarkable setting.

Open House:

Sunday, 7/5 2:00-4:00PM

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
1,718
Status:
Active
MLS#:
1011224
Type:
Single Family
Lot size:
0.39 Acres
Year built:
1970
A broker reciprocity listing Courtesy: Owner Entry.com 617-542-9300
View additional info

ADDITIONAL INFORMATION

From the moment you arrive, it's clear this is a home whose character and setting are best experienced firsthand. The bright, open-concept living area features vaulted ceilings and abundant natural light, creating an inviting space for everyday living and entertaining. A beautiful den with two walls of windows and a gas fireplace overlooks the pool and surrounding landscape. The thoughtfully designed floor plan includes two private primary suites. The main-level suite offers direct access to the backyard deck, while the lower-level suite opens directly to the outdoor kitchen through glass doors. Nestled beside a picturesque hay field and surrounded by mature landscaping, the property feels remarkably private while remaining part of a safe, quiet,friendly neighborhood. The backyard is designed for relaxation and entertaining, featuring a heated saltwater pool with waterslide, new liner (2025), and new heater (2026). The custom outdoor kitchen includes a Big Green Egg, built-in gas grill with direct gas line, sink, mini fridge, & stone countertops. Additional highlights include a two-car garage with two NEMA 14-50 EV charging outlets, a separate single-car garage, on-demand hot water and heating system (2026), updated bedroom flooring, remodeled shower, high-capacity washer (2025), and dishwasher (2025). A rare combination of privacy, upgrades, and indoor-outdoor living.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,955
Status:
Active
MLS#:
1006113
Type:
Single Family
Lot size:
6.8 Acres
Year built:
1851
A broker reciprocity listing Courtesy: Howard Hanna Rand Realty 845-294-3100
View additional info

ADDITIONAL INFORMATION

Welcome to Brook Farm - Village of Chester, New York - Circa 1851 - 6.8 Acres. There's a moment, just after you turn onto Main Street and the house comes into view above the lawn, when you understand that this is not an ordinary property. The covered porch stretches wide across the front, the slate roof catches the afternoon light, and the whole thing sits there with the quiet confidence of something that has absolutely nothing to prove. Brook Farm has been here since 1851. It will be here long after you. This is the kind of home that changes the way you think about time. Originally the crown jewel of financier Richard Delafield's 128-acre Brook Farm estate — named after his Tuxedo Park retreat — the manor was designed from the very beginning for a life lived generously. For gathering people. For long dinners that drift into evening. For the kind of entertaining that doesn't need a theme, because the house is the occasion. Step through the front door and the ceilings rise to greet you — twelve feet of plaster and molding, the proportions of a home that was never meant to feel small. The formal rooms flow one into the next: parlor, drawing room, dining room, each anchored by original fireplaces, each telling you without a word that whoever built this place understood how a house should feel. The hardwood oak floors, the walnut trim, the two grand staircases with their original woodwork — these aren't period details. They're the bones of the place, still standing, still beautiful, still doing exactly what they were put here to do. Upstairs, four bedrooms carry the same unhurried character — rooms with depth and soul, served by two full baths and a dressing room. A walk-up third floor adds two finished bonus rooms: a studio, a library, a playroom, a quiet office above the treetops. The house keeps offering more. And then there's the basement. Name it what you want — a tavern, a speakeasy, a rumpus room — but nothing quite prepares you for it. A massive brick fireplace. A built-in bar. Full-size windows flooding the space with light. And a door that opens directly onto a sunken pebbled courtyard, walled and private, where summer evenings could easily become a habit. Beyond the main house, the estate unfolds across 6.8 acres of lawn, mature trees, and open land. A charming 882-square-foot guest cottage — two bedrooms, one bath, fully independent utilities — sits privately apart from the manor. It's the kind of setup that solves problems you haven't had to solve yet: visiting loved ones, aging parents, a long-term guest, a rental income stream, a caretaker's quarters. The dairy barn and outbuildings hint at the property's agricultural past and offer a footprint ready for whatever comes next — a workshop, a studio, a small farm, a vision that hasn't quite taken shape yet but will the moment you walk the land. There's even a tennis court. Fifty-five minutes from Midtown Manhattan, charming village setting, close to the Rail Trail, highways, the Goshen Historic Track, Legoland, the Shawangunk Wine Trail, and some of the best farm-to-table dining in the Hudson Valley — Brook Farm is private without being remote, historic without being frozen in time. Properties like this — with this much land, this much character, this much history — don't come back on the market. This one hasn't been available in over seventy years. The people who have lived here understood what they had. Now it's your turn. A special property steeped in character, with a story already written… and a bold new one waiting to begin. Full of soul and raw possibility, it’s ready for reinvention, for reimagination, for a whole new energy. Awaken its potential, elevate its spirit, and make it entirely your own. The next chapter is yours to craft. Your vision. Your legacy.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,711
Status:
Active
MLS#:
1010784
Type:
Single Family
Lot size:
6 Acres
Year built:
1988
A broker reciprocity listing Courtesy: SPIRAL NY Real Estate LLC 212-381-0596
View additional info

ADDITIONAL INFORMATION

This stunning 4 bedroom, 3 bathroom home with a beautifully updated kitchen is the perfect place to call home. With plenty of space to entertain and relax, you'll love the open layout and modern amenities that this home has to offer. Whether you're enjoying a meal in the spacious kitchen or unwinding in the cozy living room, you'll feel right at home in this charming and inviting space.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,138
Status:
Active
MLS#:
1008703
Type:
Single Family
Lot size:
0.45 Acres
Year built:
1962
A broker reciprocity listing Courtesy: Howard Hanna Rand Realty 845-294-3100
View additional info

ADDITIONAL INFORMATION

This beautifully updated homes features wood floors throughout, three spacious bedrooms, two den/office spaces, formal dining room, and two full baths. The expansive primary suite has an additional 10 X 10-ft. sitting room, generous walk-in closet, an en-suite with linen closet, walk-in shower and Venetian soaking tub. The main floor bathroom is equally large with a jetted bathtub. Both the living room ams the Primary have soaring cathedral ceilings and the dining room has a 10-ft. tray ceiling. Light pours into this homemaking the oversized living area bright and cherry. The inviting eat in kitchen features stainless appliances, and for extra storage a basement pantry features floor to ceiling shelves. There is also a basement laundry with included, oversized washer and dryer. An Additional laundry hook up is also available right outside the Primary suite. The living room has a fireplace clad in beautiful cultured stone with a wood burning insert for extra heat. Outside, mature landscaping frames this beautiful house. Enjoy relaxing on a two-tiered ,massive, low maintenance Trex deck surrounded by colorful perennial flowers that bloom every spring and summer. A stone fire pit sits center stage on the lower deck, and a large shed will hold all your gardening tool. In front a quaint porch provides more outside seating. There ia a garage and plenty of additional outdoor parking. The house has upgraded Hardie plank siding and stone. Enjoy country living and pace while still only being minutes from shopping, dining and the highway.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,784
Status:
Active
MLS#:
1009848
Type:
Single Family
Lot size:
3.2 Acres
Year built:
1986
A broker reciprocity listing Courtesy: Coldwell Banker Choice Prop. 833-882-4642
View additional info

ADDITIONAL INFORMATION

Set on 3.2 acres within the Monroe-Woodbury School District, 335 Laroe Road offers a rare combination of space, functionality, and a convenient Chester location. Step inside to the welcoming two-story foyer featuring an open staircase and you'll immediately appreciate the size of the home. The main level offers a functional layout with multiple living spaces, including a living room, formal dining room, and family room anchored by a floor-to-ceiling stone fireplace. Large windows throughout the main level bring in an abundance of natural light, creating a bright and open feel throughout the home. The eat-in kitchen is designed for both everyday use and entertaining, offering generous cabinet and counter space, a center island, and an open layout that connects well with the rest of the home. French doors lead directly from the kitchen to the rear deck, which was updated within the last two years and provides plenty of room to enjoy the outdoor setting. The first floor also features a large pantry and laundry area with an impressive amount of cabinetry and storage, along with a full bathroom for added convenience. Upstairs, you'll find four bedrooms and two full bathrooms, including a spacious primary suite. The basement offers an incredible amount of additional space and storage that truly needs to be seen in person to be appreciated. Throughout the home, there is no shortage of storage or usable living space. Outside, the property provides a mix of open yard and mature trees across 3.2 acres, offering plenty of room to enjoy the outdoors. An existing in-ground pool is also located on the property and is being sold as-is. Located right next door, the Orange County Recreation Area at Laroe Road features walking and hiking trails, picnic areas, fishing ponds, and additional green space for all to enjoy. Call today to schedule your private showing. **Home is being sold AS-IS**

Beds:
4
Baths:
3.00
Sq.Ft.:
3,332
Status:
Active
MLS#:
1007687
Type:
Single Family
Lot size:
2.3 Acres
Year built:
2002
A broker reciprocity listing Courtesy: BHG Real Estate Green Team 845-208-9928
View additional info

ADDITIONAL INFORMATION

Set on 2.3 acres in Chester, this impressive property offers space, versatility, and scenic surroundings. The residence features approximately 3,332 square feet of living space with 4 bedrooms, 2 full baths and 1 half bath, thoughtfully designed for comfortable everyday living and entertaining. Interior highlights include generously sized living areas, a fireplace, abundant natural light, and flexible spaces suited for a variety of needs. Outside, the property offers exceptional utility and open space with garage/workshop space, fenced areas, and room for equipment, hobbies, recreation, or agricultural use (buyer to verify permitted uses). Enjoy peaceful views, outdoor living areas, and the privacy of a substantial parcel while remaining within convenient reach of local shops, commuter routes, and area amenities. A rare opportunity to own a property with space, functionality, and endless potential

Beds:
4
Baths:
4.00
Sq.Ft.:
4,130
Status:
Active
MLS#:
1005710
Type:
Single Family
Lot size:
2.3 Acres
Year built:
1996
A broker reciprocity listing Courtesy: Keller Williams Realty 845-928-8000
View additional info

ADDITIONAL INFORMATION

Located in the Warwick School district on a coveted street sits this larger than life home with impressive presence. The curved driveway welcomes you to the wide porch, perfect for rocking chairs and relaxing. The impressive entrance with custom stairway and window seat is just the first of impressive touches in this home. Large kitchen overlooks the yard and is well appointed with Thor oven/range, in cabinet microwave and large kitchen island. Attached is the living room/den with fireplace and access to massive walk in pantry. Step into the family room with soaring ceilings, skylights, cozy fireplace and access to second deck. The second floor master suite looks over both the front and rear yards. Built in dressers in the dressing room and a large walk in closet are just before the entrance to the 5 piece master ensuite. The space continues in the full, finished, daylight, walk out lower level. Large additional family room is flanked by two additional rooms that offer many possibilities, including home office, craft room, play room, all made more accessible by the french doors that lead to the paver patio. The backyard oasis awaits with multi-tiered decks and patios with access from the living room, kitchen, family room, and lower level. All of this welcomes you to the free form pool and spa with newly installed smart technology. All of this is located in a prime commuter location, close to major highways.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,730
Status:
Active
MLS#:
1003546
Type:
Single Family
Lot size:
1.1 Acres
Year built:
1948
A broker reciprocity listing Courtesy: Hudson Valley Griffith 845-294-9333
View additional info

ADDITIONAL INFORMATION

Something Special! See It and Fall in Love! A pavered walkway welcomes you to this curb appealing 3 BR, 2 1/2 bath Stucco Cape that is privately set on 1.1 acres! Open and sun filled with lots of windows! So many updates! Large primary BR and luxurious bath are on the 1 st floor! Open LR and DR have sliders to private deck to enjoy pastoral views and views of Sugar Loaf Mountain! 2 large BRs with large closets and full bath are on 2nd floor. Updated kitchen has granite countertops and stainless steel appliances! Close to shops and eateries in Sugar Loaf village! Warwick Schools!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,698
Status:
Active
MLS#:
1004369
Type:
Single Family
Lot size:
0.56 Acres
Year built:
1953
A broker reciprocity listing Courtesy: Keller Williams Village Sq Rlt 201-445-4300
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ADDITIONAL INFORMATION

Welcome to 24 Walnut Street, Flexibility, Space & Endless Possibility in the Heart of Chester, NY Tucked on a generous half-acre lot in the charming Village of Chester, this versatile 4-bedroom, 2.5-bath home offers a rare mother-daughter layout that delivers the best of both worlds, income potential, or simply more space to grow. Set on a quiet, tree-lined street just minutes from the Orange Heritage Trail, local dining, and easy commuter access, this property is as practical as it is inviting. The main residence spans three spacious bedrooms and 1.5 baths, offering comfortable everyday living with room for the whole family. The private secondary suite features a bright one-bedroom, one-bath layout, ideal for in-laws, extended family, an au pair, or a long-term rental opportunity. Whether you're seeking to offset your mortgage or keep loved ones close while preserving everyone's privacy, this thoughtful configuration checks every box. With a 2,698 sq ft footprint, a full basement, attached garage, hardwood floors, central air, and a sweeping 0.56-acre lot with park views, this home combines classic charm with everyday function. Located in the Chester Union Free School District and just a short drive to Legoland, the Capelli Sports Complex, and Coach USA transit to NYC — 24 Walnut Street isn't just a home. It's a lifestyle. Opportunity like this doesn't last. Schedule your private showing today.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,764
Status:
Active
MLS#:
1003760
Type:
Single Family
Lot size:
5.2 Acres
Year built:
1997
A broker reciprocity listing Courtesy: RE/MAX Town & Country 845-986-4592
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ADDITIONAL INFORMATION

Some properties are simply worth talking about... this one has all the bells & whistles you're seeking! Privately set on 5.2 scenic acres within the Warwick School District and just one hour from NYC, this distinguished Colonial pairs timeless elegance with resort-style outdoor living, mountain views, and exceptional multi-generational flexibility. A gracious front porch sets the tone, welcoming you into a home designed with both refinement and comfort in mind. Outside, the property unfolds like a private retreat, framed by mature trees, lush lawn space, an oversized deck, a pergola-covered dining area, and a heated saltwater gunite inground pool that creates an unforgettable outdoor oasis. Inside, the kitchen is a true showpiece, featuring high-end cabinetry with custom detailing, quality craftsmanship, marble countertops, an impressive center island, top-of-the-line appliances, and spectacular views. Expansive sliders open directly to the deck, creating an effortless connection between indoor living and outdoor entertaining, all set against a breathtaking natural backdrop. The main level offers beautifully appointed living spaces, including a sunken living room with a wood-burning fireplace and a private office enhanced by distinguished built-in shelving and refined detail. The primary suite feels like its own serene retreat, complete with tray ceilings and a luxurious ensuite bath designed to evoke calm and tranquility. The fully finished lower level delivers a prime multi-generational setup, complete with a second kitchen, bedroom, full bath, home gym, and generous recreation space. Ideal for extended living, guest accommodations, entertaining, fitness, or flexible day-to-day use, this level adds remarkable versatility to the home. Additional highlights include owning energy-efficient solar panels for meaningful savings and peace of mind, a two-car garage, beautiful hardwood flooring, and a quiet setting that offers privacy without sacrificing convenience. A rare offering where acreage, views, poolside living, elevated design, and commuter accessibility come together in one extraordinary property within the Wawrick School District.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,083
Status:
Active
MLS#:
898870
Type:
Single Family
Lot size:
1.84 Acres
Year built:
1984
A broker reciprocity listing Courtesy: Compass Greater NY, LLC 914-238-0676
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ADDITIONAL INFORMATION

Some lots just have good bones. This one has it's own private nature trail, stocked pond rights, and a cul-de-sac that dead-ends into miles of nature trails anchored by a solid, spacious raised ranch on 1.8 acres. Inside, the home has been partially updated and offers solid bones with room to add your own touch over time. The house delivers where it counts. Three bedrooms, two and a half baths, large kitchen, a two-car garage, and a three-season room and deck that make the most of a property this beautiful. The woodburning stove in the basement helps the winter months stay cozy while saving on fuel oil bills. Multiple outbuildings including a shed and a playhouse that will get more use than you'd expect. The lawn and mature landscaping are genuinely impressive — the kind that takes years to establish and shows the moment you pull in the driveway. Then there's everything else. When not playing on the impeccable lawn, the kids could be kids catching frogs and fish, climbing trees and building forts in the woods.. All without leaving the property. When they do, the trail into Goosepond Mountain State Park is just a few doors down, at the end of the Cul de Sac.. The street itself is unhurried and unpretentious — picture dads teaching kids to ride bikes in the road, strollers, joggers, dogs on leashes and kids swarming ice cream trucks. With easy access to amenities and a realistic commute to NYC, Booth Rd means you don't have to choose between the life you want and the job that funds it. Come feel it. The land speaks for itself.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,588
Status:
Active
MLS#:
1002536
Type:
Single Family
Lot size:
10.4 Acres
Year built:
2007
A broker reciprocity listing Courtesy: Realty Blue Corp 845-395-0746
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ADDITIONAL INFORMATION

Beautifully maintained Colonial set on a picturesque and private property offering the perfect blend of comfort, space, This spacious home features an inviting layout with generously sized rooms, hardwood flooring, elegant moldings, and abundant natural light throughout. The heart of the home is the oversized eat-in kitchen with granite countertops, extensive cabinetry, pantry space, and excellent flow into the warm and welcoming family room with fireplace — ideal for both entertaining and everyday living. Formal living and dining areas provide additional space for gatherings and special occasions. The second level offers a large primary suite with vaulted ceilings, walk-in closet, and spa-style bath, along with spacious additional bedrooms and ample storage throughout the home. Step outside and enjoy the beauty and privacy of the expansive property surrounded by mature trees and peaceful natural scenery. Whether relaxing on the front porch, entertaining on the deck, or simply enjoying the open outdoor space, this property offers a true retreat-like setting. A rare opportunity to own a move-in-ready Colonial offering privacy, charm, and exceptional living space.

Beds:
3
Baths:
4.00
Sq.Ft.:
3,535
Status:
Active
MLS#:
000137
Type:
Single Family
Lot size:
6.3 Acres
Year built:
1988
A broker reciprocity listing Courtesy: Blooming Realty 845-388-1900
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ADDITIONAL INFORMATION

220 Oxford Road is a Truly Impressive Property! Offering over 3,500 sq ft of beautifully maintained living space, this home features 3 bedrooms plus an additional upper-level room, 3 full baths, and 1 half bath. Spacious living room, stunning family room, and a practical, well-designed kitchen. The home showcases elegant finishes throughout along with brand new flooring that adds a fresh modern touch. Full basement provides excellent storage space. Additional features include Central AC, original Andersen custom windows, and an attached 2-car garage. Step outside to a massive deck, spacious shed, and gorgeous landscaping set on a nice-sized lot. Conveniently located close to all amenities, this property offers privacy, space, and everything you could want in a home and more!

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Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Listings courtesy of One Key MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 11/13/2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2026, OneKey MLS, Inc. All Rights Reserved.



Chester 10918 Real Estate

Chester is located in New York. Chester, New York 10918has a population of 12,477. Chester 10918 is more family-centric than the surrounding county with 37.24% of the households containing married families with children. The county average for households married with children is 36.93%.

The median household income in Chester, New York 10918 is $120,288. The median household income for the surrounding county is $85,640 compared to the national median of $69,021. The median age of people living in Chester 10918 is 39.1 years.

Chester Weather

The average high temperature in July is 83.4 degrees, with an average low temperature in January of 16.3 degrees. The average rainfall is approximately 47.1 inches per year, with 39.1 inches of snow per year.

Chester Map

Chester Real Estate Market Conditions

  • Median sales price

    $437,000
    17.6%
    change since last quarter
  • # Active listings

    60
    30-day change

Chester Schools and Demographics

Education near Chester, NY

City County
High School Graduates 95.19 89.92
College Degree - 2 year 9.51 10.52
College Degree - 4 year 37.38 31.44
Graduate Degree 12.24 10.46
Expenditures per Student 27,939 27,939
Students per Teacher 12.3 12.3

Elementary Schools near Chester, NY

Grades Students P/T Ratio ZIP
Chester Elementary School KG - 05 469 14.7 10918
Golden Hill Elementary School PK - 05 388 12.4 10921
Goshen Intermediate School 03 - 05 655 15.2 10924
Kiryas Joel Village School PK - KG 149 6 10950
North Main Street School 02 - 05 558 13.9 10950
Pine Tree Elementary School 02 - 05 833 13.5 10950
Round Hill Elementary School PK - 05 540 17.4 10992
Scotchtown Avenue School KG - 02 591 16 10924
Taft Elementary School KG - 05 785 18.3 10992

Middle Schools near Chester, NY

Grades Students P/T Ratio ZIP
C J Hooker Middle School 06 - 08 720 14.3 10924
Greenwood Lake Middle School 04 - 08 303 12.4 10950
Washingtonville Middle School 06 - 08 1,027 13.7 10992

High Schools near Chester, NY

Grades Students P/T Ratio ZIP
Chester Academy-Middle/High School 06 - 12 556 13.2 10918
Goshen Central High School 09 - 12 925 13.6 10924
Washingtonville Senior High School 09 - 12 1,411 13.5 10992

Ungraded Schools near Chester, NY

Grades Students P/T Ratio ZIP
* Goshen Secure Center 08 - 12 56 10924
Orange-Ulster Boces KG - 12 1,007 26.4 10924
S S Seward Institute 06 - 12 465 11.4 10921

Demographics near Chester, NY 10918

Zip Code City
Neighborhood Type Suburban
Population 12,477 398,277
Population Density 379 490
Median Age 39.1 37
People per Household 2.8 2.9
Median Household Income 120,288 85,640
Average Income per Capita 49,991 37,651

Real estate near Chester