Chester Homes with Warwick Valley School district

Welcome to Chester, New York – a hidden gem nestled in the heart of Orange County. This charming town is not just a picturesque retreat but also a vibrant community that offers a perfect blend of rural tranquility and modern convenience. With its rolling hills, lush landscapes, and a rich history that dates back to the 18th century, Chester is an ideal locale for families, retirees, and everyone in between.

One of the standout features of Chester is its affiliation with the esteemed Warwick Valley School District. Known for its commitment to academic excellence and holistic development, this school district provides a nurturing environment for children to thrive. Families looking to settle in Chester can take comfort in knowing that their children will receive top-notch education and ample extracurricular opportunities.

The real estate market in Chester is diverse, offering a wide range of homes that cater to various tastes and budgets. From charming historic houses to contemporary builds, there’s something for everyone. The scenic views and close-knit community atmosphere make Chester an inviting place to call home.

In addition to its educational advantages, residents of Chester enjoy an array of local amenities, including quaint shops, delightful eateries, and outdoor recreational activities. With nearby parks and hiking trails, outdoor enthusiasts will relish the chance to explore the natural beauty surrounding the area.

Whether you're looking to buy your first home or seeking a serene place to retire, Chester, NY, with its excellent schools and welcoming community, is the perfect place to create lasting memories. Come discover the charm of Chester – where your dream home awaits!

Newest Chester Homes with Warwick Valley School district

$549,999

4 Beds ⋅ 3 Baths ⋅ 1028872 MLS

This charming updated 4-bedroom beauty in the Warwick School district offers a private and quiet setting featuring an above ground pool surrounded by a freshly painted deck just 3 minutes from Sugar Loaf Arts and Crafts Village. Its' kitchen has been upgraded boasting stainless steel appliances, granite countertops, and cherrywood cabinetry with undermount lighting and a wine/ beverage cooler. Hardwood floors can be found throughout with the open living room and family room each graced with woodburning fireplaces. The primary on-suite bathroom has also been freshly renovated. Additional highlights in the lower level include an extra-large bedroom with New flush mount lighting, New tiled floors and an expanded laundry room. Other updates include a New Leach field System 2022, Septic system serviced in 2024, New Roof on both the home and shed 2023 and a new pool filter 2023. Best commuter location with only 52 miles to GW Bridge and an easy access to RT17. Low Taxes! Additional Information: Heating Fuel: Oil Above Ground, Parking Features:1 Car Attached. Schedule your showing today!

7 Lakeview Drive, Chester

$875,000

4 Beds ⋅ 3 Baths ⋅ 1011165 MLS

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.

49 Stone Mountain Trail, Chester

$775,000

3 Beds ⋅ 3 Baths ⋅ 986323 MLS

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 layout designed for everyday living. The updated kitchen, complete with brand new LG appliances, center island, and a stylish tiled backsplash, opens into a formal dining room—perfect for hosting friends. Enjoy multiple living spaces, including a sun-filled living room and a cozy family room with a fireplace, creating a warm and welcoming atmosphere. A dedicated home office offers the flexibility you need for remote work or a quiet study space. Upstairs, the primary suite is a true retreat, featuring a private full bath with double vanities, a whirlpool tub, and a private balcony overlooking Creamery Pond—the perfect place to start or end your day. Two additional generously sized bedrooms and a full hall bath complete the upper level. The finished basement (not included in square footage) provides even more room to spread out, offering ideal space for a playroom, home gym, or guest area, along with walkout access and egress windows for added convenience. Step outside to your expansive deck and enjoy your private, fenced-in waterfront backyard—perfect for summer barbecues, morning coffee, or simply taking in the peaceful surroundings. Spend your days fishing, kayaking, or relaxing by the water from your own private dock. Conveniently located near schools, the Village of Sugar Loaf, boutique shops, and dining, and just about an hour to NYC. Enjoy easy access to local orchards, wineries, ski areas, the Appalachian Trail, and the Heritage Bike Trail—making this home ideal for both relaxation and year-round recreation. A rare opportunity to own a true waterfront gem!

149 Creamery Pond Road, Chester

$875,000

3 Beds ⋅ 3 Baths ⋅ 974429 MLS

The Conklin House: A Masterpiece of History & Modern Luxury. Experience the perfect blend of early 20th-century charm and 21st-century comfort. The Conklin House, a classic 1908 Queen Anne Victorian, stands as a commanding presence at the edge of the historic Village of Sugar Loaf. The home has always been used residentially but zoning permits commercial usage as well. Originally ordered from the Sears & Roebuck catalogue and delivered by rail, this "pre-fab" pioneer was famously the first electrified home in the area. The current owner has meticulously performed a full-scale reconstruction, ensuring the home is entirely turn-key while honoring its heritage. The home features modern infrastructure with all-new mechanical systems, walls, and energy-efficient windows. Its preserved character is astounding. Every period molding, the original grand staircase, panel doors and authentic flooring have been salvaged and restored. The architectural heritage is monumental as it features its signature steeply pitched hipped roof and a dominant front-facing gable that defines its Victorian silhouette. Built for Howard Conklin—the local postmaster/general store owner—and later by his son, Dr. Roger Howard Conklin, this residence has been a cornerstone of the community for over a century. It represents a rare opportunity to own a piece of Hudson Valley history without the burden of historic maintenance. The lifestyle in Sugar Loaf and Chester, NY is refreshing, especially to New Yorkers getting away from the city. Nestled in a tight-knit arts and crafts hamlet, one is steps away from 18th-century buildings housing artisan studios, galleries, and boutique eateries. And there is rich Outdoor Adventure to take advantage of too! The area has direct access to the 18-mile Heritage Trail for biking and walking, plus proximity to Goosepond Mountain State Park and the Birnberg Nature Preserve. Its rural serenity offers a quiet, creative lifestyle surrounded by majestic mountains and rolling meadows, all while being part of a bustling weekend destination. Driving to and from the Conklin House to NYC is about 1 hour and 15 minutes and using mass transit a little longer. This is more than a house; it is a storied landmark reimagined for the modern connoisseur. Nothing compares to the character, lifestyle and wilderness that the Conklin House has to offer.

2 Pine Hill Road, Chester

$759,900

4 Beds ⋅ 3 Baths ⋅ 981270 MLS

This beautiful custom home is planned to be built in the highly sought-after Sugar Loaf area, offering the convenience of municipal water and sewer. The main level welcomes you with warm hardwood floors and a kitchen featuring a choice of elegant granite or quartz countertops, a stainless steel appliance package, a center island perfect for meal preparation, and a spacious dining area with a slider that opens to a spacious deck. The cozy family room, complete with a fireplace, creates an ideal spot for gatherings. Also on this level are three comfortable bedrooms, including a primary suite with a bathroom showcasing a double vanity, a relaxing soaking tub, and a tiled shower, along with a stylish main hall bath. The finished lower level offers additional space with an extra bedroom or home office, along with a large recreation or living room—perfect for relaxing or entertaining. Enjoy extra features and the chance to choose custom finishes that make your home uniquely yours. Located conveniently near shopping, charming boutique stores, restaurants, wineries, breweries, apple orchards, lakes, Appalachian trails, and major commuter routes, with just about an hour to reach NYC.

90 Pewter Circle, Chester

$869,900

4 Beds ⋅ 3 Baths ⋅ 966048 MLS

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 open-concept living spaces ideal for modern living. Lot 3 will showcase an approximately 3200 sq. ft. colonial offered at $879,900, and Lot 4 will feature a beautiful traditional colonial approx. 2500 sq ft., priced at $869,900. Buyers also have the opportunity to bring their own custom plans and collaborate with the builder to create a home tailored to their vision. Each residence will be crafted with quality finishes and attention to detail throughout. The heart of the home will be a beautifully designed custom kitchen featuring a selection of cabinetry styles, granite or quartz countertops, farmhouse sinks, and a generous $27,000 allowance toward kitchen and bathroom cabinetry and surfaces. These thoughtfully curated options allow buyers to personalize their space while maintaining a high standard of design. Hardwood floors will be installed throughout the home, creating warmth and continuity from room to room, while the bathrooms will feature beautifully selected tile finishes for both style and durability. The spacious family room will serve as a welcoming gathering space, complete with a stunning 36-inch fireplace. The open layout flows seamlessly into a large dining area perfect for hosting holidays and special occasions, along with a comfortable living room designed for everyday relaxation and entertaining. Upstairs, each home will offer four generously sized bedrooms. The primary suite is designed as a private retreat, complete with a spa-inspired bathroom featuring a soaking tub, double vanity, and separate shower—creating a serene space to unwind at the end of the day. Golden Meadows offers exceptional convenience, located just minutes from major highways, shopping centers, apple orchards, wineries, and a wide selection of restaurants. Residents will also enjoy close proximity to the charming boutiques and the Sugar Loaf Performing Arts Center, the scenic Heritage Trail for biking and walking, and the vibrant community atmosphere that makes this area so desirable. This is a rare opportunity to build a new custom home in a prime location while enjoying modern amenities, refined finishes, and the ability to personalize your dream home from the ground up.

10 Wells Sweep Lane, Chester

$879,900

4 Beds ⋅ 3 Baths ⋅ 965992 MLS

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 open-concept living spaces ideal for modern living. Lot 3 will showcase an approximately 3200 sq. ft. colonial offered at $879,900, and Lot 4 will feature a beautiful traditional colonial approx. 3000 sq ft., priced at $869,900. Buyers also have the opportunity to bring their own custom plans and collaborate with the builder to create a home tailored to their vision. Each residence will be crafted with quality finishes and attention to detail throughout. The heart of the home will be a beautifully designed custom kitchen featuring a selection of cabinetry styles, granite or quartz countertops, farmhouse sinks, and a generous $27,000 allowance toward kitchen and bathroom cabinetry and surfaces. These thoughtfully curated options allow buyers to personalize their space while maintaining a high standard of design. Hardwood floors will be installed throughout the home, creating warmth and continuity from room to room, while the bathrooms will feature beautifully selected tile finishes for both style and durability. The spacious family room will serve as a welcoming gathering space, complete with a stunning 36-inch fireplace. The open layout flows seamlessly into a large dining area perfect for hosting holidays and special occasions, along with a comfortable living room designed for everyday relaxation and entertaining. Upstairs, each home will offer four generously sized bedrooms. The primary suite is designed as a private retreat, complete with a spa-inspired bathroom featuring a soaking tub, double vanity, and separate shower—creating a serene space to unwind at the end of the day. Golden Meadows offers exceptional convenience, located just minutes from major highways, shopping centers, apple orchards, wineries, and a wide selection of restaurants. Residents will also enjoy close proximity to the charming boutiques and the Sugar Loaf Performing Arts Center, the scenic Heritage Trail for biking and walking, and the vibrant community atmosphere that makes this area so desirable. This is a rare opportunity to build a new custom home in a prime location while enjoying modern amenities, refined finishes, and the ability to personalize your dream home from the ground up.

1414 Kings Highway, Chester

$699,995

6 Beds ⋅ 4 Baths ⋅ 960665 MLS

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 over 4,000 square feet of living space, the home blends authenticity with thoughtful updates. Original architectural elements—including wide-plank floors, carefully refinished—add warmth and character throughout. Two staircases provide access to the second floor, reflecting the home’s natural evolution over time. The kitchen is rich in historic detail, highlighted by authentic hand-hewn wood support beams, original to the house and a true testament to 19th-century craftsmanship. Modern enhancements integrate seamlessly, including granite countertops, custom cabinetry, stainless steel appliances, and new high-performance HPL flooring designed for durability. The layout includes six bedrooms and four bathrooms, with twin primary suites located on opposite wings of the home, each offering walk-in closets and a sense of privacy. The welcoming foyer features new hardwood floors, while the spacious mudroom has been updated with new tile flooring and a full bathroom, ideal for everyday country living. A sunken family room with a fireplace creates a cozy gathering space, and the large formal dining room, featuring newly refinished hardwood floors, is perfectly suited for holidays and special occasions. At the rear of the home, a sun-filled sunroom offers a peaceful retreat—ideal for indoor plants, a reading nook, or a creative space that enjoys natural light throughout the day and connects the home to its surrounding landscape. The basement reflects the home’s practical history. While rustic, it once served as a working space where wine was produced beginning in the 1950s, complete with original shelving used for canning and seasonal storage. Outside, raised garden boxes invite you to plant vegetables, herbs, or flowers—continuing the tradition of working the land and enjoying the rewards of homegrown living. Additional features include a two-car garage with upper-level storage and a location that offers the peace of country life with convenience—just one hour from NYC. This is more than a residence—it is a historic home, lovingly maintained, ready to welcome its next chapter.

487 Black Meadow Road, Chester

$350,000

858370 MLS

Very private lot in mature subdivision of large homes. Home site has been cleared and driveway base laid down. With a small amount of brush-clearing in the tree line there can be views of the valley and watershed lands.

Odyssey Drive, 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.