Colonial Homes for Sale in Chester, NY

Beautiful and spacious 4 Bedroom, 2.5 Bath Colonial set on park-like property in a lovely neighborhood with a serene backdrop of mature trees, offering both privacy and a peaceful setting. This home features a large eat-in kitchen with abundant cabinetry, tremendous counter space, and a sliding glass door leading to a newer rear deck—perfect for relaxing or entertaining outdoors.The oversized

Mary Ann Mitchell eXp Realty

Secluded Trout Brook Estate: Expansive 5,700+ Sq Ft, 6-Car Garage, Ready for Multi-Gen Living and Entertaining. Nestled on nearly six private acres in the exclusive Trout Brook Estates, this expansive Colonial-style estate blends classic elegance with modern comfort. Built in 1993 and thoughtfully designed for multi-generational living and refined entertainment, the home offers generous space,

Carmela Lopez Borrazas Serhant LLC

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

Moshe Kaufman MK Realty Inc

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.

Artan Kukaj SPIRAL NY Real Estate LLC

Welcome to 24 Boville Court that sits on 3.7 acres a beautifully maintained home perfectly positioned on a quiet cul-de-sac in the highly desirable Town of Chester. Nestled on a premium end corner lot that extends all the way to Route 94, this exceptional property offers the perfect blend of privacy, comfort, and convenience.Step inside to discover bright, inviting living spaces, generously

Jennifer Acevedo KW Hudson Valley United

Rare opportunity to purchase this gorgeous property that consists of 3 homes nestled on 3.5 beautiful acres. The main Colonial residence has been gutted and will need to be renovated/rebuilt, however, you can live in one of the additional two residences while you renovate! The 2nd residence called the “stone cottage” has 2 fieldstone fireplaces, a full kitchen, a vaulted ceiling in the bedroom, a

Frank Golio Howard Hanna Rand Realty

Set gracefully on 3.8 private acres within the highly coveted Warwick School District, this exceptional custom home offers a rare blend of architectural elegance and refined living. Surrounded by a collection of equally distinguished residences, the property provides an expansive, park-like sanctuary while remaining nestled in the heart of one of the region’s most sought-after communities.

Courtney Tablante Keller Williams Realty

Own a true piece of history with the iconic Hambletonian House, a one-of-a-kind Victorian estate built in the 19th century by William Rysdyk, original owner of Hambletonian 10—the legendary sire that shaped nearly all modern Standardbred racehorses. Perfectly positioned on nearly three private acres atop a knoll in the heart of Chester, New York, this meticulously maintained property offers a

Beth Palma Keller Williams Realty

Set on over 10 private acres in the rolling hills of Orange County, this exceptional custom colonial offers the rare combination of luxury, privacy, and convenience AND just minutes from the heart of Chester and major commuter routes. Built in 2017 and thoughtfully designed with over 2,700 square feet of living space, 45 Whitetail Run delivers the kind of lifestyle buyers dream about but rarely

Melissa Forsyth Hudson Valley Home Connection

Imagine ending everyday watching the sun set from your front porch, experiencing views that change with every season. Sunset views, fenced yard, brand new Trex deck, pool, home office and room for four sleeping spaces make this the perfect property. Perched at the top of the highly sought-after Fieldcrest subdivision, this stunning Colonial captures breathtaking panoramic views and unforgettable

Gina Dudgeon Howard Hanna Rand Realty

Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combination of municipal water and sewer, thoughtfully designed floor plans, and stunning lots in a highly desirable location in the Warwick school district. Homes will start at $780,000, with multiple design options available to suit a variety of lifestyles. Lots 1 and 2 will feature custom Bilonial designs with

Carla Terranova Keller Williams Realty

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

Asha Keegan Howard Hanna Rand Realty

Welcome to the highly sought-after Creamery Estate, located in the award-winning Warwick school district!. This inviting waterfront Colonial-style home offers the perfect blend of comfort, charm, and scenic beauty, set on an acre of beautifully maintained grounds with peaceful views of Creamery Pond. This 3-bedroom, 3 full bath home features hardwood floors throughout and a spacious, easy-flow

Carla Terranova Keller Williams Realty

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

Dovid Hoffman MK Realty Inc

Set at the end of a quiet executive cul-de-sac, this refined modern colonial offers a rare blend of quality, scale, and effortless livability on over two acres of level, park-like grounds framed by mature trees. Designed for both everyday comfort and elevated entertaining, the home unfolds with a sense of openness and intention, where natural light and thoughtful craftsmanship define every

Frank Muccari Cronin & Company Real Estate

Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home features 4 spacious bedrooms and 3 full bathrooms, creating an inviting layout ideal for everyday living and entertaining.Step inside to a grand, sun-filled foyer with soaring ceilings that set the tone for the home’s warm and

Janet Rendle Weichert Realtors

Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second

Elimelech Kremer MS Realty Group USA, Inc

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

James Cosenza BHG Real Estate Green Team

Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combination of municipal water and sewer, thoughtfully designed floor plans, and stunning lots in a highly desirable location in the Warwick school district. Homes will start at $780,000, with multiple design options available to suit a variety of lifestyles. Lots 1 and 2 will feature custom Bilonial designs with

Carla Terranova Keller Williams Realty

THE ULTIMATE HUDSON VALLEY LEGACY ESTATE | 53 ACRES OF UNMATCHED POTENTIAL Rarely does a property emerge that perfectly balances refined luxury living with raw, untapped opportunity. Nestled in the heart of scenic Chester, New York, 20 Goshen Road offers an expansive 53-acre canvas designed for the visionary. Whether you envision a world-class equestrian facility, a high-potential residential

Ramanjit Dhanoa eXp Realty

A Private Suburban Retreat on Prestigious Garnet Hill. This Center Hall Colonial offers an exceptional residence- refined suburban living with the space, privacy, and sophistication sought by discerning buyers—just about an hour from Manhattan. Positioned on a beautifully landscaped 3+ acre property, the home features approximately over 4,700 square feet of elegant living space, offering 5

Rachel Baruchov Platinum Realty Associates

A Landmark Farmhouse with a Story to Tell.Standing proudly since 1872, this historic Colonial farmhouse is one of the very first homes built on Black Meadow Road and remains a meaningful piece of Chester’s agricultural past. Once surrounded by hundreds of acres of open farmland and dairy cows, the home still carries the soul of a working farm while offering the comforts of modern living. With

Dominic Santagato Joseph Baratta Company Realty

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

Moshe Kaufman MK Realty Inc

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

Kimberly Corkum Keller Williams Realty

Historic Colonial Era Home in the Heart of Sugar Loaf, NYLocated just 60 minutes from NYCZoned Residential/CommercialStep into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Original building was built in 1770, this unique property features:• One

Mark Karten Karten Real Estate Svcs LLC

Welcome to this exceptional private retreat nestled on beautifully landscaped grounds in desirable Chester. Offering the perfect blend of space, comfort, privacy, and lifestyle, this impressive property is surrounded by natural beauty while remaining conveniently close to shopping, dining, major highways, and the scenic Stewart State Forest. From the moment you arrive, you’ll appreciate the

Joseph Rosenfeld Flag Realty Group

Beautifully spacious Colonial set on 1.8 private acres on Pine Hill Road, offering 3,120 square feet of rustic, updated charm behind a gated entry and surrounded by magnificent grounds. The main level welcomes you with a spacious eat-in kitchen that flows seamlessly into the dining area, creating an ideal setting for everyday living and effortless entertaining. The massively large living room

Charnie Guttmann eRealty Advisors, Inc

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

Christina D'Altiiio Coldwell Banker Choice Prop.

Beautiful Colonial set on just under an acre of meticulously landscaped property, offering breathtaking sunset views from a very private backyard. The taxes may be reduced by up to 20%; however, a tax appeal cannot be filed until 2027. Great spacious front porch! On a quiet cul-de-sac, this home features a stunning in-ground pool with a new heater, cover & pump. Pool filter, and liner are about 4

Sharon Kushner eXp Realty

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 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

Dovid Hoffman MK Realty Inc

Nestled on a quiet road off the beaten path, this serene 4-bedroom, 2.5-bathroom Colonial offers the perfect blend of secluded tranquility and commuter convenience. The main level features a traditional layout with a spacious living room, formal dining room, and a cozy recreation room perfect for relaxing. The functional eat-in kitchen serves as the heart of the home, while all four bedrooms are

Charles Moore Keller Williams Realty

Welcome to 176 Beverly Road, Colonial-style nestled on 2.5 beautifully landscaped acres in the highly sought-after Warwick Valley School District. From the moment you arrive, you'll appreciate the home's curb appeal featuring custom stone entrance pillars with illuminated house numbers, a beautifully inlaid driveway address, professionally landscaped grounds accented by natural stone and

Jocelyn Rivera

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

Martha Randazzo Howard Hanna Rand Realty