Chester Homes for Sale

Welcome to Chester, New York, a charming town nestled in the heart of Orange County, where community spirit and educational excellence thrive. This picturesque area is not only known for its stunning landscapes and outdoor recreational opportunities but also for its highly regarded school district, making it an ideal place for families seeking a nurturing environment for their children.

Chester School District prides itself on providing a well-rounded education that emphasizes academic achievement, creativity, and character development. With a strong commitment to fostering a love for learning, the district offers a variety of programs designed to cater to diverse student needs. From advanced placement courses to extracurricular activities, Chester schools equip students with the tools they need to succeed both in and out of the classroom. Parents can rest easy knowing their children are receiving a top-notch education in a supportive and engaged community.

As you explore Chester, you'll discover a range of beautiful homes for sale that cater to various lifestyles and budgets. From charming historic houses to modern family homes, Chester’s real estate market offers something for everyone. Picture yourself enjoying cozy evenings in a spacious backyard or taking leisurely strolls through the serene streets of this lovely town. With its close-knit community, excellent schools, and scenic surroundings, Chester is not just a place to live—it's a place to thrive.

If you’re ready to make Chester your home, let us guide you through the exciting journey of finding your dream property in this idyllic setting. Welcome to Chester, where home and heart unite!

Newest Chester Homes for Sale

$750,000

5 Beds ⋅ 3 Baths ⋅ 1031147 MLS

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 10 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.

3 Hilltop Lane, Chester

$350,000

4 Beds ⋅ 1 Baths ⋅ 1031155 MLS

A Diamond in the Rough! Calling all handymen to bring this Village Charmer back to its' original glory. This home has a large Living Room with a cozy alcove, spacious Dining Room and large Kitchen with sliders to a rear deck and yard. It also features 4 nice sized bedrooms. With a "little love and vision" this home could be a lovely family home! Could be a wonderful opportunity for investors! Close to shops and restaurants! Great commuter location! Come preview today!

151 Main Street, Chester

$750,000

5 Beds ⋅ 3 Baths ⋅ 1031045 MLS

1 Hilltop Lane, Chester

$629,000

4 Beds ⋅ 2 Baths ⋅ 1030227 MLS

Gorgeous corner fully fenced in Bi-Level house for sale in Town of Goshen. State of the art heating system, central air, beautiful sunroom, modern kitchen and bathrooms. House was fully remodeled in 2014. The main level features three bedrooms, master bathroom has walk in closet with access to the bathroom, spacious living room, dinning room, kitchen and sunroom. The lower level offers additional living space with a fully finished basement, 4th bedroom, modern bathroom, additional storage space and laundry room. Extra large deck, above ground pool with paver patio. House is conveniently located to major highways, shopping, dinning and bus stations. Move in ready! Must come and see!

14 Larchwood Drive, Goshen

$599,900

3 Beds ⋅ 2 Baths ⋅ 1029645 MLS

Located in the heart of the Village of Chester, this beautifully updated home offers the rare combination of modern comfort, privacy, and convenience. Just steps from Chester Academy and the Heritage Trail, this property provides easy access to walking, biking, running, local events, and community amenities while offering the peaceful retreat of your own private acreage. Set on 4 private acres, this home is a nature lover’s dream. The expansive property offers the perfect balance of open space and natural beauty, providing endless opportunities for outdoor enjoyment, family adventures, gardening, recreation, and creating your own private oasis. The large yard gives children plenty of room to play, explore, and connect with nature, while offering the space and flexibility for a hobby farm, gardens, chickens, outdoor activities, or other homesteading dreams. The entire home has been thoughtfully renovated within recent years, offering a fresh, updated feel throughout. A new HVAC system provides added comfort, efficiency, and peace of mind. The home also offers excellent future expansion potential with a full walk-out basement ready to be finished—perfect for a recreation room, guest suite, home gym, office, playroom, or media area. A standout feature is the oversized garage, providing exceptional space for vehicles, storage, hobbies, a workshop, or additional workspace. Step outside and enjoy the wrap-around back porch, the perfect place to relax, entertain, and take in the peaceful surroundings of your expansive yard. Whether enjoying morning coffee, hosting friends and family, or watching kids explore the outdoors, this space truly embraces the best of country-style living with village convenience. Property Highlights • Beautifully renovated home with modern updates • Just steps from Chester Academy and the Heritage Trail • Prime Village of Chester location close to schools, shops, and amenities • 4 private acres with beautiful natural surroundings • Perfect property for nature lovers and outdoor enthusiasts • Large yard ideal for kids to play, explore, and create memories • Endless possibilities for gardens, recreation, and hobby farming • New HVAC system • New roof • Full walk-out basement with finishing potential • Oversized garage with ample storage and workspace • Wrap-around back porch overlooking the property A rare opportunity to own a move-in ready home with land, updates, and endless possibilities—all in one of Chester’s most convenient locations. Whether you’re looking for space to grow, room for your family to explore, or the opportunity to create your own private retreat, 50 Hambletonian Ave offers the lifestyle you’ve been searching for.

50 Hambletonian Avenue, Chester

$750,000

5 Beds ⋅ 3 Baths ⋅ 1025992 MLS

2 Hemlock Court, Chester

$399,999

4 Beds ⋅ 2 Baths ⋅ 1024779 MLS

Discover the timeless charm and endless potential of this classic Colonial farmhouse, ideally situated on just under one level acre in the heart of Chester, NY. Offering approximately 1,560 square feet of living space, this 4 bedroom, 2 bath home is filled with character and craftsmanship. Step inside to find original hardwood floors, a cozy wood-burning stove, and an artistic, welcoming atmosphere that highlights the home's authentic farmhouse appeal. Rich with historic charm and original details, this property is ready for its next owner to restore and make it their own. Enjoy peaceful, scenic views of the surrounding greenery while benefiting from a highly convenient commuter friendly location. Just minutes from the highway, downtown Chester, Goshen, Monroe, and Warwick, you'll have easy access to local shops, restaurants, parks, wineries, farmers markets, and everything the Hudson Valley has to offer. Priced with the home's restoration needs in mind, this is a rare opportunity to invest in a property with incredible potential, generous outdoor space, and an unbeatable location. Whether you're searching for a primary residence, weekend retreat, or renovation project, this farmhouse is ready to be brought back to life. Schedule your private tour today and imagine the possibilities!

241 Meadow Avenue, Chester

$540,000

4 Beds ⋅ 2 Baths ⋅ 963560 MLS

Lovely raised ranch on a cul de sac. Updated kitchen and bathrooms. Open floor plan with a deck off the kitchen/dining area. The deck is fabulous and large, perfect for entertaining, dining al fresco, enjoying a beverage of your choice or lounging with a good read. Beautiful, large backyard. Don't miss the opportunity to own a home that gives you a lot for your money. Come explore the lay out see if it works for you.

5 Walnut Court, Goshen

$850,000

5 Beds ⋅ 3 Baths ⋅ 1020076 MLS

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.

5 Hilltop Lane, Chester

$750,000

5 Beds ⋅ 3 Baths ⋅ 1020128 MLS

3 Hemlock Court, Chester

$649,999

4 Beds ⋅ 3 Baths ⋅ 1013375 MLS

Private 2.5-Acre Contemporary Retreat with Expansive Deck – Chester, NY Welcome to 424 Laroe Road — a rare opportunity to own 2.5 private acres in sought-after Chester. This solid 1974 contemporary home offers 2,316 square feet of flexible living space with 4 bedrooms and 3 bathrooms, perfectly positioned to take full advantage of its peaceful, tree-lined setting. Step outside onto the expansive multi-level deck and immediately feel the difference that true privacy and land can make. Ideal for entertaining, morning coffee, or simply enjoying the quiet, the outdoor living space is a standout feature rarely found at this price point. The generous lot offers room to expand, garden, play, or create your own outdoor oasis. Inside, the home provides a comfortable layout with bright living areas, multiple bedrooms, and the potential to personalize to your style. Ample garage and parking space add everyday convenience. Located in Orange County with easy access to major routes, this property delivers the space and privacy so many buyers are searching for — without sacrificing convenience. Whether you’re looking for a primary residence with room to grow or a peaceful retreat, 424 Laroe Road offers a strong foundation and exceptional land value. Key Features: 4 bedrooms | 3 bathrooms 2,316 sq ft 2.5 private acres Expansive deck for outdoor living Built 1974 – solid bones with modern potential Convenient Chester location Schedule your private showing today and experience the space, privacy, and potential for yourself.

424 Laroe Road, Chester

$789,900

5 Beds ⋅ 4 Baths ⋅ 1012919 MLS

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.

19 Grand View Terrace, Chester

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . 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.