Chester NY Real Estate & Homes for Sale

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Beds:
4
Baths:
3.00
Sq.Ft.:
3,000
Status:
NEW LISTING
MLS#:
966048
Type:
Single Family
Subdivision:
Golden Meadows
Lot size:
1.6 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Keller Williams Realty 845-928-8000
View additional info

ADDITIONAL INFORMATION

Beautiful custom homes are coming soon to 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.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,200
Status:
NEW LISTING
MLS#:
965992
Type:
Single Family
Subdivision:
Golden Meadows
Lot size:
1.51 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Keller Williams Realty 845-928-8000
View additional info

ADDITIONAL INFORMATION

Beautiful custom homes are coming soon to 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.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,998
Status:
NEW LISTING
MLS#:
963657
Type:
Single Family
Lot size:
0.57 Acres
Year built:
1947
A broker reciprocity listing Courtesy: BHG Real Estate Green Team 845-208-9928
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ADDITIONAL INFORMATION

Set on nearly half an acre in the Village of Chester, this charming brick Cape Cod offers a rare combination of privacy and convenience, featuring a flexible four room layout and a fully finished lower level with full bath. Positioned well back from the road with a long private driveway and no homes directly across the street, the setting feels peaceful and tucked away while remaining minutes from Route 17, shopping, dining, local wineries and breweries, Legoland, and Woodbury Common Premium Outlets. A nearby commuter bus with service into New York City is just a short walk from the home. School bus pickup is conveniently located at the corner. Inside, thoughtful renovations have created a clean, modern feel throughout, including updated flooring with no carpeting. The home features two well-appointed bedrooms, including a primary bedroom with a walk-in closet and a second bedroom with built-in storage. Two fully renovated bathrooms and versatile bonus rooms offer flexibility for a home office, guest space, or den. The renovated kitchen anchors the main living space, while a one-year-old boiler provides added peace of mind. Storage is a standout feature, including an unfinished walk-up second floor, a two-car garage, and a separate exterior storage or workshop room ideal for hobbies or projects. With major updates complete, excellent privacy, and commuter-friendly access, this home offers comfort, flexibility, and long-term value in a highly desirable location. Some images included in the listing have been virtually staged to help showcase the intended use and true potential of spaces in the home.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,053
Status:
NEW LISTING
MLS#:
964957
Type:
Condo
Subdivision:
Whispering Hills
Year built:
1984
A broker reciprocity listing Courtesy: ARC Realty 1 in Sales 845-783-5145
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ADDITIONAL INFORMATION

ONLY CASH OFFERS!! LOW TAXES! Two Level Living! 2 Bedrooms! 1 1/2 Bathrooms! 1 Car Garage! Updated Kitchen! Updated Bathrooms! Living Room with Fireplace! Sliders To Patio! Perfect Commuter Location! Walk to NYC Bus & Shopping! Close to Major Highways! Country Club Living! Clubhouses! Pools! Tennis! Tot Lot! Basketball! Dog Walk!

Beds:
2
Baths:
1.00
Sq.Ft.:
1,026
Status:
Active
MLS#:
964090
Type:
Single Family
Lot size:
0.29 Acres
Year built:
1910
A broker reciprocity listing Courtesy: HomeSmart Homes & Estates 845-547-0005
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ADDITIONAL INFORMATION

Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay window create a bright, welcoming atmosphere. Wall sconces add a soft glow, and a wall A/C unit ensures comfort throughout the warmer months. The eat in kitchen blends practicality with charm, offering tile floors, a newer refrigerator, a handy island, abundant cabinetry, and a pantry for extra storage. Another bay window brings in natural light and enhances the home’s cozy appeal. A full bathroom with a classic pedestal sink and tub completes the main living space. The primary bedroom features hardwood floors, newer windows, two closets, and its own wall A/C unit. A second bedroom—equally charming—also offers hardwood floors and plenty of natural light. Throughout the home, you’ll find generous storage options, including ample closets and a pull down attic. The property is thoughtfully equipped with a natural gas generator, a paved driveway, and multiple outbuildings that expand its functionality. The main house includes an attached two car garage, while a separate two car detached garage showcases original carriage house doors that add a touch of historic character. A small shed provides additional storage, and an oversized outbuilding—with an 8' garage door, separate electric and gas meter, and gas boiler heat—offers exceptional versatility. Above it sits a caretaker’s apartment, ideal for guests, extended family, or workspace needs. All structures are being sold as is. An additional parcel with a storage barn is also available, offering even more room to grow, store, or create. This property blends charm, practicality, and potential in a way that’s increasingly rare—inviting you to imagine the many ways it can fit your lifestyle.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,120
Status:
Active
MLS#:
958731
Type:
Single Family
Lot size:
1.8 Acres
Year built:
1990
A broker reciprocity listing Courtesy: eRealty Advisors, Inc 914-712-6330
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ADDITIONAL INFORMATION

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 serves as the heart of the home, offering abundant space, a warm fireplace, and a comfortable gathering atmosphere. Upstairs, the serene primary bedroom retreat features a private balcony overlooking the expansive backyard, providing a peaceful place to relax and take in the property’s beautiful surroundings. Additional highlights include a partially finished full basement, central air, alarm system, new generator, and expansive rear deck ideal for entertaining or relaxing. Conveniently located with easy access to Route 17 and shopping, this property offers the perfect blend of privacy, comfort, and convenience.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,084
Status:
Active
MLS#:
962709
Type:
Condo
Lot size:
0.11 Acres
Year built:
1987
A broker reciprocity listing Courtesy: HomeSmart Homes & Estates 845-547-0005
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ADDITIONAL INFORMATION

Welcome to 2913 Whispering Hills Drive – A Move-In Ready End Unit in the Heart of Chester! This bright and spacious 2-bedroom, 1-bath townhouse offers an open-concept layout with soaring vaulted ceilings and an abundance of natural light. As an end unit, you’ll enjoy added privacy along with extra windows that make the space feel even more expansive. The inviting living room features a cozy fireplace and seamlessly flows into the dining area, creating the perfect space for everyday living and entertaining. Step out onto your private balcony to enjoy morning coffee or evening relaxation. The kitchen is well-appointed with granite countertops, stainless steel appliances, and plenty of cabinet space. The beautifully renovated bathroom offers modern finishes and a fresh, updated feel. Additional highlights include: Brand new furnace, brand new central air conditioning unit, one-car garage with electric vehicle charger, open layout with vaulted ceilings, end-unit location for added privacy. While a fresh coat of paint could make it truly shine, the major updates have already been done — making this an excellent opportunity for both homeowners and investors alike. Conveniently located close to shopping, dining, major highways, and everything Chester has to offer. Don’t miss your chance to own this well-maintained, light-filled townhouse in Whispering Hills!

Beds:
5
Baths:
6.00
Sq.Ft.:
5,403
Status:
Active
MLS#:
962813
Type:
Single Family
Lot size:
5.4 Acres
Year built:
1982
A broker reciprocity listing Courtesy: Flag Realty Group 845-205-0089
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ADDITIONAL INFORMATION

DISCOVER THE EPITOME OF LUXURY LIVING! With 5400 sq ft of breathtaking property, where every corner is designed for both elegance and practicality!! With expansive living areas, high-end finishes, and modern amenities, this home is perfect for entertaining or enjoying quiet moments. Embrace a lifestyle of comfort and sophistication in a space that truly feels like a retreat all year round!! Featuring a main house of 3800 sq. ft. with 4 bedrooms and 3.5 baths, complemented by a beautifully finished basement that adds three additional rooms and another bath. The open kitchen boasts elegant granite countertops, while two sunrooms and spacious living areas provide ample space for relaxation and entertainment. The attached 1600 sq. ft. post & beam (log house) in-law suite ensures complete privacy for guests or extended family, featuring its own entrance, kitchen, and living spaces. With Central AC, and modernized bathrooms, this home is move-in ready. Step outside to a stunning park-like backyard, perfect for outdoor enthusiasts, complete with three private decks, lush gardens, stone patios, a greenhouse, fire pit, and a dedicated BBQ area. “See it now -gone soon!!!”

Beds:
4
Baths:
3.00
Sq.Ft.:
2,506
Status:
Active
MLS#:
961100
Type:
Single Family
Lot size:
1.4 Acres
Year built:
1998
A broker reciprocity listing Courtesy: Century 21 Full Service Realty 845-782-2221
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ADDITIONAL INFORMATION

Updated 4BR Colonial in Chester – Monroe-Woodbury Schools! Welcome home to this beautifully maintained 4-bedroom, 3-bath Colonial offering timeless style, functional space, and significant updates in the highly sought-after Monroe-Woodbury Central School District! A grand two-story entry foyer with a dramatic cathedral ceiling makes an impressive first impression, filling the home with natural light. Hardwood floors and crown molding add warmth and architectural detail throughout the main level. The updated kitchen showcases granite countertops and stainless-steel appliances and flows seamlessly into the inviting family room, featuring a wood-burning fireplace and custom built-in cabinetry—creating the perfect setting for both everyday living and entertaining. A formal dining room provides an elegant space for gatherings, while a main-level den/home office offers flexibility for remote work, playroom, or additional living space. Upstairs, the primary suite offers high ceilings, a walk-in closet, and an updated private bath complete with a jetted tub. Three additional bedrooms and full bath complete the upper level. The finished basement adds 775 square feet of additional living space, with multiple egress windows including a versatile bonus room —ideal for a gym, media room, guest space, or second office. Major improvements have already been completed, including dual-zone central A/C (2018), roof (2021), well pump and holding tank (2019), heat pump (2020), and a Trex deck and front porch (2022), providing peace of mind for years to come. Enjoy year-round comfort, low-maintenance outdoor living, and welcoming curb appeal. Ideally located with convenient access to major highways, shopping, dining, parks, and recreational trails—just 60 miles to NYC—this home offers the perfect balance of suburban comfort and commuter convenience. Move-in ready and thoughtfully updated—this one truly stands out! Schedule your private showing today!

Beds:
4
Baths:
3.00
Sq.Ft.:
3,348
Status:
Active
MLS#:
961236
Type:
Single Family
Lot size:
53 Acres
Year built:
2002
A broker reciprocity listing Courtesy: eXp Realty 888-276-0630
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ADDITIONAL INFORMATION

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 development, or a private sustainable sanctuary, this estate delivers on every front. THE RESIDENCE Built in 2002, the custom-designed 3,348 sq. ft. home features 4 spacious bedrooms and 3 full baths. The layout is thoughtfully crafted to maximize natural light and views of the sprawling grounds. The infrastructure is built for the enthusiast, featuring an oversized 3-car garage with 10-foot doors—perfect for car collections, boats, or equipment. THE GROUNDS & EQUESTRIAN APPEAL Step outside into a nature lover’s paradise. The property is crisscrossed with miles of well-maintained horse trails, making it a premier choice for equestrian pursuits. The land is rich with resources, including an estimated $30,000 in marketable timber and a thriving, mature orchard boasting over 40 trees including pear, cherry, apple, and peach varieties. SUSTAINABILITY & UTILITY Embrace a self-sufficient lifestyle with an infrastructure designed for resilience. The property features a large-scale chicken coop with a capacity for up to 200 birds and an incredibly efficient heating system powered by an outdoor wood-burning furnace, significantly reducing utility costs while utilizing the property's natural resources. INVESTMENT & DEVELOPMENT Positioned in one of Orange County’s most investment-friendly regions, the 53.00-acre lot size offers significant subdivision possibilities. Investors and developers will recognize the rare value in the expansive road frontage and the desirable Chester location, just moments from local amenities yet completely secluded. Discover the endless possibilities of 20 Goshen Road—where your private retreat meets a high-yield investment.

Beds:
6
Baths:
4.00
Sq.Ft.:
4,204
Status:
Active
MLS#:
960665
Type:
Single Family
Lot size:
1 Acres
Year built:
1872
A broker reciprocity listing Courtesy: Joseph Baratta Company Realty 800-628-3119
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ADDITIONAL INFORMATION

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.

Open House:

Sunday, 3/8 1:00-3:00PM

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
2,544
Status:
Active
MLS#:
959390
Type:
Single Family
Lot size:
1.9 Acres
Year built:
1997
A broker reciprocity listing Courtesy: Keller Williams Hudson Valley 845-610-6065
View additional info

ADDITIONAL INFORMATION

Welcome to 5 Bens Way, a beautifully positioned residence tucked away on a quiet cul-de-sac in the highly sought-after Town of Chester, New York. This property offers an exceptional blend of privacy, space, and convenience, making it an outstanding opportunity for buyers seeking a well-rounded Hudson Valley lifestyle with easy access to modern amenities, commuter routes, and recreational attractions. Set on a generously sized parcel, this home immediately stands out for its curb appeal and setting. The peaceful residential street enhances the sense of tranquility while still being just minutes from the heart of Chester Village, Sugar Loaf, and surrounding communities. The location provides convenient access to local shopping, dining, parks, and everyday services, while also offering proximity to major roadways that connect seamlessly to Orange County and beyond. Inside, the home offers a thoughtfully designed layout that balances functionality and comfort. Natural light fills the living spaces, creating a warm and inviting atmosphere throughout. The main living areas are well-proportioned, allowing for flexible use whether entertaining guests, working from home, or enjoying everyday living. The flow between rooms enhances both usability and visual appeal, offering a layout that adapts easily to a variety of lifestyles and needs. The kitchen serves as a central gathering space and is designed to support both daily routines and special occasions. Has ample cabinetry, generous counter space, and a layout that promotes efficiency, the kitchen is well-suited for cooking, hosting, and casual dining alike. Adjacent dining and living areas allow for seamless transitions, making the home ideal for gatherings of any size. Bedrooms are comfortably sized and offer a peaceful retreat at the end of the day. Each room provides flexibility for different uses, such as guest accommodations, home office space, or creative studios. Bathrooms are conveniently located and designed to support comfort and functionality. Additional interior features contribute to the home’s overall appeal, including ample storage options, practical utility spaces, and thoughtful design elements that enhance daily living. The home’s layout allows for both shared spaces and private areas, providing balance and versatility. Step outside to enjoy the outdoor features that truly elevate this property. The yard offers abundant space for outdoor activities, gardening, or simply enjoying the natural surroundings. Whether relaxing outdoors, hosting gatherings, or creating personalized outdoor living areas, the property provides a strong foundation for a variety of uses. The lot’s size and configuration offer privacy while maintaining ease of maintenance. One of the standout aspects of Bens Way is its location within the Hudson Valley, a region known for its scenic beauty, seasonal activities, and vibrant local culture. Nearby parks, trails, and recreational areas offer year-round opportunities for outdoor enjoyment. The area also provides access to wineries, farm markets, cultural destinations, and community events that contribute to a rich and dynamic lifestyle. Commuters will appreciate the property’s accessibility to major routes, making travel to surrounding towns, employment centers, and transit options both efficient and convenient. This balance of peaceful residential living with practical connectivity makes the location particularly attractive. Whether you are looking for a primary residence or a long-term investment opportunity, this home presents a compelling option. Its combination of location, layout, outdoor space, and overall livability creates a strong value proposition in today’s market. This property offers the opportunity to own a home that supports comfort, flexibility, and connection to everything the Chester area has to offer. Schedule your private showing today and explore the potential that 5 Bens Way holds for its next owner.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,867
Status:
Active
MLS#:
956879
Type:
Single Family
Subdivision:
Cooper's Ridge
Lot size:
1 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Our House Real Estate Group 845-705-8093
View additional info

ADDITIONAL INFORMATION

ONE LEVEL LIVING/ EASY COMMUTE- with additional space upstairs and down! ... Don't miss this beautiful TURN-KEY Arts & Crafts-style FARMHOUSE TO BE BUILT! ..... COME AND FULLY CUSTOMIZE this 4-bdrm, 3 bath, 2,106+/- sq. ft home (including bonus room)! LARGE MAIN FLOOR PRIMARY BEDROOM with ENSUITE BATH & WALK-IN CLOSET plus A SECOND MAIN FLOOR BEDROOM (NURSERY, OFFICE, CRAFT ROOM ETC.). FANTASTIC VAULTED FAMILY ROOM WITH LARGE FIREPLACE (GAS OR WOOD-BURNING), GOURMET KITCHEN with eat-in breakfast area and PANTRY including a convenient pass-through window to the family room! Separate DINING ROOM with French doors to the back plus a FULL HALL BATH and convenient LAUNDRY area. Upstairs offers 2 ADDITIONAL LARGE BEDROOM with WALK-IN CLOSETS & another large full bath. ....Finish the optional second floor bonus space for an office, bedroom, gym, studio and more for an extra 239 sq ft! Two-car garage with convenient access right to the kitchen for easy grocery loading PLUS a FULL WALK- OUT BASEMENT!! ..... BUYER-FINANCED BUILD: CASH OR CONSTRUCTION-TO-PERMANENT LOAN ONLY. ..... CALL TO SCHEDULE A TOUR OF THE LOT & schedule a builder's meeting. This will be a fantastic home with all high end finishes, standard! Lovely 1-Acre lot w/MOUNTAIN VIEWS ... VERY COMMUTABLE!

Open House:

Saturday, 3/7 12:00-1:30PM

More Open House Info >

Beds:
5
Baths:
4.00
Sq.Ft.:
5,080
Status:
Active
MLS#:
955725
Type:
Single Family
Subdivision:
Country Woods
Lot size:
3.8 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Prominent Properties Sotheby's 201-768-9300
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ADDITIONAL INFORMATION

Welcome home to 4 Camelback Road. Nestled on a serene cul-de-sac in the executive subdivision of Country Woods, this magnificent home sits on one of the most beautiful streets within the sought-after Monroe-Woodbury School District. Step into perfection as you enter the grand foyer and are immediately welcomed by a light-filled, open floor plan that exudes elegance and sophistication. This meticulously maintained home showcases exquisite craftsmanship and attention to detail throughout Custom moldings, gleaming hardwood floors, designer lighting, and stately architectural columns that evoke the feel of a Westchester or Bergen County estate. The bright and spacious formal living room flows seamlessly into a warm and inviting family room featuring a stunning custom stone fireplace, elegant mantle, and French doors leading to the outdoors. The expansive chef’s kitchen is a showstopper complete with granite countertops, a large center island, built-in cooktop, double oven, microwave, stainless steel appliances, and a walk-in pantry. Perfect for both everyday living and entertaining. The formal dining room, accented by wainscoting and a lighted niche, provides ample space for memorable gatherings. Upstairs, the luxurious primary suite offers vaulted ceilings, two walk in closets, and a spa inspired bath, along with an adjoining office or private gym. Four additional bedrooms are generously sized, each offering comfort and style. The fifth and second largest bedroom is perfect for guests or extended family. The full, finished walkout basement with 9 foot ceilings and a half bath adds an impressive space for entertaining. Outside, your private backyard oasis awaits featuring a magnificent Trex deck overlooking 3.8 acres of pure tranquility. With its perfect blend of luxury, privacy, and convenience, this exceptional home offers an ideal retreat just a 45 minute commute from New York City.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,728
Status:
Active
MLS#:
951876
Type:
Single Family
Lot size:
0.12 Acres
Year built:
1850
A broker reciprocity listing Courtesy: Karten Real Estate Svcs LLC 929-605-5545
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ADDITIONAL INFORMATION

Historic Colonial Era Home in the Heart of Sugar Loaf, NY Located just 60 minutes from NYC Zoned Residential/Commercial Step 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 of a kind Colonial era home, featuring original exposed hand-hewn beams, barn siding walls, and a fireplace • Two spacious workshops/studios – ideal for artists, entrepreneurs, or makers – currently a woodcarvers workshop. • A must-see, living piece of history full of soul and story • Stunning view of Sugar Loaf Mountain right out your front door Zoned commercial/residential, this home offers the perfect blend of live-work potential — ideal for a workshop, gallery, studio, or cozy retreat. Just steps away: • 2 popular restaurants • A vibrant performing arts center • Local breweries with live music • Coffee shop/ Roaster & Brunch House • Year-round craft markets & community events Sugar Loaf is a renowned creative hub, and this home is at the very center of it all. Nestled in the heart of Sugar Loaf’s artisan community, this unique home and shop was long owned by cultural mainstay Jarvis Boone — a woodcarver, painter, entertainer, and local luminary whose influence helped shape Sugar Loaf’s identity as an artists’ village back in the mid 1960’s. Boone’s legacy lives on through his son Clay, who apprenticed with his father beginning at age 7. He has carried on the woodcarving tradition as Sugar Loaf’s resident woodcarver for the last 58 years. This property offers more than walls and beams. Full of character and creative potential, this property is perfect for artists, craftsmen, woodworkers or anyone drawn to a vibrant, storied community. It offers a living canvas for makers and dreamers to carry forward a tradition of creativity. Don't miss your chance to own a timeless treasure in one of the Hudson Valley’s most beloved villages.

Open House:

Sunday, 3/8 1:00-3:00PM

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
2,722
Status:
Active
MLS#:
952148
Type:
Single Family
Lot size:
3.2 Acres
Year built:
2002
A broker reciprocity listing Courtesy: Keller Williams Realty 845-928-8000
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ADDITIONAL INFORMATION

Exquisite 4 bedroom 3 bath colonial , timeless grandeur meets modern luxury nestled gracefully on a private cul de sac. Amidst meticulously manicured grounds, this colonial style home offers an unparalleled blend of classic elegance and contemporary comfort, from the moment you approach the stately wrought iron fenced property and are greeted by a wrap around porch, you are welcomed by a grand foyer, and you experience a magnificent and undeniable sense of elegance. The main level unfolds with exquisite architectural details, including extensive crown molding, recessed lighting and hardwood floors throughout. Ornate lighting and dazzling chandeliers add a touch of sophisticated brilliance to every space. The inviting formal living room features custom built-ins that softly illuminate cherished collections, perfectly complemented by french doors leading to the family room with additional access to the wrap-around front porch- an idyllic spot for morning coffee or evening relaxation. The kitchen boasts top of the line stainless steel appliances, a generous pantry and a convenient built in desk. Adjacent to the kitchen, a spacious laundry room offers ample storage and utility. A cozy family room features a charming wood burning fireplace, creating a warm and inviting atmosphere, while a beautifully appointed half bath serves guests on the first floor. Off the eat in kitchen step into the outstanding three season sun room, where retractable windows invite the outdoors in, creating a seamless connection with nature and providing a serene escape. The second floor features plush carpeting that ensures comfort and tranquility. The sanctuary of the primary bedroom suite awaits, featuring dramatic cathedral ceilings and dual expansive closets. The custom primary bathroom is a spa like retreat, designed for ultimate relaxation with radiant heated floors and an oversized shower. The double vanity is a one of a kind custom built vanity by a local artisan. Three additional generously sized bedrooms provide ample space for family or guests. Beyond the interior, the property continues to shine. The expansive back deck is an entertainer's dream complete with self watering planters for effortless gardening. The fully fenced backyard enveloped by mature landscaping, ensures privacy and keeps wildlife at bay, offering a secure haven for recreation and outdoor enjoyment. Further enhancing this magnificent home are a two car garage and a full unfinished walk out basement presenting endless possibilities for customization- imagine a home theater, private gym, home office, additional living space.This is more than just a home. It is a lifestyle. Schedule your private tour today.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,084
Status:
Active
MLS#:
950534
Type:
Condo
Year built:
1984
A broker reciprocity listing Courtesy: Keller Williams Realty 845-928-8000
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ADDITIONAL INFORMATION

Welcome Home! 2 Bedrooms 1 Bathroom move in ready end unit. Recently renovated including a new kitchen with granite counter tops and stainless steel appliances, new bathroom, new windows, new laminate flooring, new water heater, new light fixtures and recessed lighting. Nothing to do but move in! Close to supermarket, post office, restaurants, urgent care, highway. Perfect commuter location. Don't wait this one is ready to go!

Beds:
5
Baths:
4.00
Sq.Ft.:
3,136
Status:
Active
MLS#:
950640
Type:
Single Family
Lot size:
3 Acres
Year built:
2005
A broker reciprocity listing Courtesy: MS Realty Group USA, Inc 845-367-7470
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ADDITIONAL INFORMATION

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 kitchen and additional living space, ideal for an extended family or guests. Enjoy outdoor living with an inground pool and a large, private yard. Complete with a 3-car garage and located in the Monroe-Woodbury School District, this home offers space, comfort, and versatility.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,780
Status:
Active
MLS#:
944582
Type:
Single Family
Lot size:
0.36 Acres
Year built:
1961
A broker reciprocity listing Courtesy: Avion 845-388-1216
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ADDITIONAL INFORMATION

Welcome to your dream home at 108 Pine Hill Rd, Chester, NY, where comfort meets elegance in a spacious single-family abode. This charming home offers a thoughtfully designed layout, featuring a welcoming kitchen with direct outdoor access, perfect for morning coffees or entertaining. The first floor also hosts a cozy living room and a bright family room, both filled with natural light. Upstairs, four generously sized bedrooms await, including a master suite with a private bath for ultimate comfort. The fully finished basement adds versatile living space for a playroom, home gym, or entertainment area. Embrace the vibrant and inviting atmosphere of this beautiful house and make it your new home sweet home. Schedule a viewing today!

Beds:
5
Baths:
4.00
Sq.Ft.:
4,772
Status:
Active
MLS#:
931380
Type:
Single Family
Lot size:
3.6 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Platinum Realty Associates 845-354-3246
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ADDITIONAL INFORMATION

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 bedrooms and 3.5 full baths. Luxury begins at the illuminated pillars lining the paver driveway, leading to a stone-accented front entry. Inside, sun-filled interiors highlight quality craftsmanship throughout. The two-story foyer features tray ceilings and expansive windows, while recessed lighting, built-in surround sound, and pre-wiring for a security system add comfort and functionality. The chef’s kitchen is a true centerpiece, featuring floor-to-ceiling custom cabinetry, granite countertops, a large center island with seating, and a premium Sub-Zero stainless-steel refrigerator. Adjacent casual dinette provides effortless flow for hosting, with sliding doors opening to the outdoor living areas which provide direct access to a deck & patio area. The oversized family room becomes the center of the home surrounded by windows and comforted by the fireplace.  Upstairs, the primary suite offers a private retreat with two custom walk-in closets, a sitting area, and alcove. The en-suite bath features dual vanities, a walk-in shower with multiple shower heads, and a jetted soaking tub overlooking serene sunset views. Three additional bedrooms and one full bathroom are generously sized and thoughtfully arranged on the same level. The finished lower level offers a private home theater, custom bar, a fully mirrored gym, a bonus room, a full bathroom and walkout access, creating a versatile space ideal for recreation, entertaining, or extended living. Outdoors, the property delivers a resort-style experience with an oversized basketball court, a hot tub, and expansive open grounds framed by mature landscaping and stunning sunset views. The setting offers exceptional privacy and room to relax, entertain, or expand. Additional highlights include a three-car garage and a setting that perfectly balances tranquility with accessibility. This is a rare opportunity to enjoy luxury suburban living—where space, serenity, and elegance meet effortless access to New York City.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,000
Status:
Active
MLS#:
944607
Type:
Single Family
Lot size:
3.2 Acres
Year built:
2008
A broker reciprocity listing Courtesy: eRealty Advisors, Inc 914-712-6330
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ADDITIONAL INFORMATION

B"H Grab this opportunity!!! Cozy Home in great condition sitting on a 3.2 ACER Property!!! Enjoy the above ground pool !!! Wonderful neighborhood and calm area. Open living room with wood burning fireplace, The kitchen offers a breakfast bar, Center island, Stainless steel appliances, Multiple counter space and cabinets. Finished lower level with a Den/office, Family room and full bathroom. Full unfinished attic with lots of storage space. Sq. Ft. is approximate

Beds:
2
Baths:
2.00
Sq.Ft.:
1,072
Status:
Active
MLS#:
942965
Type:
Condo
Lot size:
0.09 Acres
Year built:
1987
A broker reciprocity listing Courtesy: Keller Williams Hudson Valley 845-610-6065
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ADDITIONAL INFORMATION

Welcome to Whispering Hills! This beautifully maintained home features a galley kitchen with stainless steel appliances and a convenient in-unit washer and dryer. The first level offers a stylish half bath and well-kept flooring throughout the kitchen, dining room, and living room. Enjoy cozy evenings by the fireplace, and extend your living space outdoors on the private patio. Upstairs, you’ll find two comfortable bedrooms and a full bath. The primary bedroom includes a walk-through closet that provides direct access to the bathroom, which also opens to the hallway for added convenience. A skylight brightens the upper level with natural light, and both bedrooms are carpeted for comfort. Whispering Hills offers exceptional community amenities, including two pools, a clubhouse, a tennis court, and a tot lot. Sidewalks throughout the neighborhood make it ideal for leisurely strolls any day. Close to shopping, restaurants, and the Short Line bus to the city, this home combines comfort, convenience, and an enjoyable lifestyle. Come take a look!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,816
Status:
Active
MLS#:
943068
Type:
Single Family
Lot size:
10.5 Acres
Year built:
1967
A broker reciprocity listing Courtesy: Loop Realty Inc 845-388-1155
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ADDITIONAL INFORMATION

This nice quiet house is a great place to call home. With almost 11 acres of land, there's a lot of space to enjoy activities and outdoor fun. The first floor of the house offers a nice layout with big living room, family room, kitchen, dining room, and a half bath. and a washer and dryer room . Bedrooms are nice and big making it very comfortable . The house will need some TLC and will need renovation and repairs to restore it to its full potential. This gives you the opportunity to add taste and value to the property. worth checking this out!

Beds:
4
Baths:
3.00
Sq.Ft.:
3,866
Status:
Active
MLS#:
940751
Type:
Single Family
Lot size:
5.2 Acres
Year built:
1860
A broker reciprocity listing Courtesy: Tuxedo Hudson Realty Corp 845-915-4567
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ADDITIONAL INFORMATION

Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with original wooden and stone mantles, 10' ceilings, and large sun-filled windows throughout. The main level offers two gracious living rooms, a formal dining room, a dedicated office, and an updated kitchen outfitted with a Wolf range, cherry cabinetry, generous storage, and a walk-in pantry. A dedicated first-floor laundry room adds convenience. Upstairs are four spacious bedrooms and two full bathrooms, including a generous primary suite with a large walk-in closet and a 5-piece ensuite bath. These spaces reflect the thoughtful renovation completed in 2014 by previous owners, which also included a living room extension, upgraded kitchen, and a 1,250 sq ft three-car garage designed to complement the home’s historic profile. The lower level is just as impressive. The dry, clean basement contains a unique wine-tasting room set against the original hand-stacked stone foundation, offering a charming and unexpected entertaining space. The 5-acre property offers level, usable land framed by mature native trees—including two historic Linden trees dating to the late 1800s—and expansive lawn. In 2022, the owners installed an 8,000 sq ft organic vegetable garden complete with deer fencing and a full irrigation system, creating a highly productive and beautiful outdoor space. Additional improvements include new trees and screening, newly added parking, a ground-floor repaint, refinished wood floors, an EV charger (CCS), and the conversion of the former stable into a functional workshop. Three outbuildings expand the estate’s potential for creative, professional, or commercial work. The 3,036 sq ft workshop is fully equipped with 6" concrete floors for heavy machinery, 220V power, propane heat, ventilation systems, a bathroom with independent septic, and a four-bay garage. The 1,300 sq ft former stable has been transformed into another heated workspace with 220V power, a kitchenette, a sink, and large sliding barn doors for easy access. The charming 144 sq ft red barn, believed to predate the house and possibly dating back to the 1700s, features traditional mortise-and-tenon joinery and hand-tooled beams. Today it serves as a functional landscape shed while retaining its historic character. History runs deep on the property. The grounds include the historic Sears Cemetery, an 11-memorial family graveyard with stones predating the home's construction. Among those buried here is Hector Craig, a U.S. Congressman and father-in-law to William Havemeyer, part of a family central to the development of early Washingtonville. A rare opportunity to own a fully modernized historic estate, this property seamlessly merges historic integrity, architectural detail, and contemporary comfort across home, land, and workspaces. One Hour to NYC, Close to All Transportations, Dining, Hiking, Shopping and other Conveniences.

Open House:

Sunday, 3/8 12:00-2:00PM

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
2,870
Status:
Active
MLS#:
935115
Type:
Single Family
Lot size:
4.1 Acres
Year built:
1988
A broker reciprocity listing Courtesy: RE/MAX Benchmark Realty Group 845-565-0004
View additional info

ADDITIONAL INFORMATION

Discover modern living at its best in this beautifully designed 2,870 sq ft contemporary home with flexible floor plan and wonderful tranquility! Set on 4.1 private acres and featuring its own pond and seasonal babbling brook, 16 Oxford Springs Road is perfect for those seeking a full-time residence or Hudson Valley getaway. This home offers retreat-like privacy yet is only minutes to all amenities and approx 60 miles to NYC. Inside, oak hardwood floors flow across both levels, setting a warm yet sophisticated tone. The main level boasts a bright eat-in kitchen, sunken living room with fireplace and sliders to the expansive backyard, a recently updated full bathroom, and 4 living spaces that allow you to customize the space to your specific needs! These adaptable spaces can be tailored to just about any lifestyle whether it be a home office, additional living area, playroom, dining room, or even a guest room. Upstairs, the primary bedroom suite impresses with soaring cathedral ceilings, three walk-in closets, and a recently updated en-suite bathroom with modern finishes. Two additional spacious bedrooms share a full hallway bathroom, providing comfort and convenience for family or guests. Step outside to enjoy the peaceful deck overlooking your private natural landscape, creating a seamless connection between the home’s interior and the natural beauty of the backyard. The newly fenced backyard is perfect for pets, play, and entertaining, while the oversized two-car garage, whole-house generator, UV light water filtration system, and new gutter guards add everyday practicality and peace of mind. With unmatched privacy, contemporary style, updated amenities, and a breathtaking natural setting, this home offers the perfect blend of elegance, comfort, and escape.

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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

    $512,500
    17.6%
    change since last quarter
  • # Active listings

    45
    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