Chester NY Real Estate & Homes for Sale

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Beds:
4
Baths:
3.00
Sq.Ft.:
1,867
Status:
NEW LISTING
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
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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!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,954
Status:
NEW LISTING
MLS#:
951920
Type:
Single Family
Lot size:
0.93 Acres
Year built:
1999
A broker reciprocity listing Courtesy: Cronin & Company Real Estate 845-744-6275
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ADDITIONAL INFORMATION

MONROE WOODBURY SCHOOLS! BRAND NEW KITCHEN! ABSOLUTE MUST SEE!Welcome to your dream home in the highly sought-after Monroe Woodbury School District. Privately set at the end of a long driveway on just under one acre, this beautifully renovated Colonial offers an incredible balance of peace, privacy, and recent upgrades. From the moment you step inside, you are greeted by a stunning foyer that sets the tone for the rest of the home. The main living level features gorgeous new wood floors and an impressive staircase that immediately catches the eye. The cozy living room is anchored by a wood-burning fireplace, creating a warm and inviting space perfect for snowy winter nights. Designed with entertaining in mind, the expansive family room flows seamlessly into the dining area and is filled with natural light. Double-wide sliders frame picturesque views of the private backyard and lead out to a spacious rear deck, ideal for gatherings or quiet mornings with coffee. The absolutely stunning kitchen has been completely redone and is a true showstopper, featuring quartz countertops, upgraded cabinetry, and stainless steel appliances that make both everyday living and hosting effortless. A convenient half bath and large storage closet completes the first floor. Upstairs, you will find three generously sized bedrooms, including an impressive primary suite with a spa-like ensuite bath that feels straight out of a luxury retreat. An additional large hall bathroom and a versatile bonus room provide endless possibilities for a home office, playroom, or guest space. Storage is abundant with a large basement, attic, and a two-car garage. Adding to the home’s value and efficiency is a paid-off BP Solar array that will convey free and clear, offering substantial electric savings for years to come. To sum it all up, this is a beautifully renovated Colonial in the Monroe Woodbury School District, set on a large and usable property with central air conditioning, a two-car garage, an incredible primary suite, and so much more. There is truly so much to love here, and this is a home you need to see in person to fully appreciate. Call today to schedule your private showing.

Beds:
5
Baths:
4.00
Sq.Ft.:
5,080
Status:
NEW LISTING
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:
4
Baths:
4.00
Sq.Ft.:
4,508
Status:
Active
MLS#:
953574
Type:
Single Family
Lot size:
3.8 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Keller Williams Realty 845-928-8000
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ADDITIONAL INFORMATION

A Refined Custom Estate in One of Warwick’s Most Coveted Enclaves. Set on 3.8 private acres and surrounded by similarly distinguished luxury residences, this exceptional custom home offers the rare balance of architectural elegance, lifestyle amenities, and commuter convenience—located within the highly regarded Warwick School District. Offering over 4,500 square feet of beautifully finished living space and 6,800+ total square feet including an unfinished basement, the home showcases thoughtful design and elevated finishes throughout. A dramatic double-height great room with a striking gas fireplace creates a memorable arrival, while graceful arched doorways and upgraded black windows add timeless sophistication. The main-level primary suite serves as a private retreat, complete with a spa-inspired bath and exclusive deck/patio overlooking the serene grounds. Designed for both intimate living and entertaining, the home features a butler’s pantry, media room, refined lounge spaces, a dedicated office nook, and an upper-level catwalk and loft that enhance the home’s custom character. The expansive unfinished basement provides endless opportunities for future customization—ideal for a private gym, wine cellar, or entertainment level. Outdoors, enjoy a welcoming front rocking-chair porch and peaceful acreage offering privacy without isolation. Natural gas availability adds everyday convenience and long-term value. Ideally positioned in a prime commuter location, the property is just moments from major highways and within walking distance to Tin Barn Brewing, while also offering close proximity to Warwick’s celebrated wineries, farm markets, and dining—delivering a lifestyle that is both refined and relaxed. A rare opportunity to own a sophisticated estate where luxury, location, and lifestyle converge.

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.

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:
4
Baths:
1.00
Sq.Ft.:
2,000
Status:
Active
MLS#:
2600369
Type:
Single Family-Detached
Lot size:
1.9 Acres
Year built:
1997
A broker reciprocity listing Courtesy: Robert DeFalco Realty, Inc. 718-987-7900
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ADDITIONAL INFORMATION

BEAUTIFUL HOME - GREAT LOCATION.

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!

Open House:

Sunday, 2/1 12:00-2:00PM

More Open House Info >

Beds:
2
Baths:
2.00
Sq.Ft.:
1,072
Status:
Active
MLS#:
951306
Type:
Condo
Year built:
1987
A broker reciprocity listing Courtesy: eXp Realty 888-276-0630
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ADDITIONAL INFORMATION

Welcome to 4508 Whispering Hills, a well-maintained and thoughtfully updated 2-bedroom, 1.5-bath home offering comfort and convenience. Recent upgrades include an updated kitchen and bathrooms, hardwood floors, a newer sliding glass door, garage door with opener, and an upgraded furnace, providing peace of mind for the next owner. The home features a one-car garage and a practical layout that makes everyday living easy. Ideally located within walking distance to the bus stop, and just minutes from shopping, dining, and major highways, this home offers excellent accessibility for commuters and everyday errands. A move-in-ready opportunity in a highly convenient location.

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:
2
Baths:
2.00
Sq.Ft.:
1,072
Status:
Active
MLS#:
924165
Type:
Condo
Year built:
1984
A broker reciprocity listing Courtesy: Howard Hanna Rand Realty 845-294-3100
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ADDITIONAL INFORMATION

Welcome to your 2 bedroom, 1.5 bathroom town house condo with a one car garage in the highly desirable Whispering Hills Community in Chester, NY. Well maintained and cared for by its original owner, this unit is located in a nice private section along a green space. The second floor features two spacious bedrooms and one full bathroom. The primary bedroom has cathedral ceilings and a sizable walk-in closet. The second bedroom comes with a large closet. Sliding door lead to a nice outdoor patio area. The one car garage is great for private enclosed parking and offers extra storage. Community recreation events during the year including: pet parades, Earth Day events, gingerbread house decorating, toy drives. Included with monthly HOA fee: Water, garbage and recycling, snow removal, landscaping, pool pass to two separate pool areas, use of tennis courts, basketball court, dog run, playground and clubhouse. Low taxes!!! Excellent commuter location. Bus stop to NYC/NJ in the complex. Close to the highway, supermarket, and shopping. Minutes from Woodbury Common, LegoLand NY, Garnet Health Medical Center, Chester Mall Shopping Center.

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#:
941582
Type:
Condo
Subdivision:
Whispering Hills
Year built:
1987
A broker reciprocity listing Courtesy: John J Lease REALTORS Inc 845-344-2800
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ADDITIONAL INFORMATION

Welcome to this charming 2-bedroom condo in the desirable Whispering Hills community! This unit faces green space and trees for added privacy as well as comfortable living spaces. The home features a cozy living room with a fireplace, a dining area, and a full kitchen ready for everyday meals or weekend entertaining. Enjoy the convenience of having your own in-unit washer and dryer, plus a private patio perfect for relaxing outdoors. The condo offers one full bathroom and one half bath, along with an attached one-car garage for added ease. Whispering Hills residents also enjoy fantastic community amenities, including a sparkling pool, tennis courts, a playground, clubhouse and a basketball court. With a nearby bus stop providing an easy commute to NYC and less than one mile to NYS route 17 this home blends comfort, convenience, and lifestyle—everything you need for modern living!

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:
3
Baths:
2.00
Sq.Ft.:
1,056
Status:
Active
MLS#:
942503
Type:
Single Family
Lot size:
2 Acres
Year built:
1957
A broker reciprocity listing Courtesy: Blooming Realty 845-388-1900
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ADDITIONAL INFORMATION

Discover comfort, privacy, and convenience in this beautifully maintained home set on a 2 acre property. Located in a peaceful area, this residence offers a warm and inviting layout with a nicely sized kitchen, three comfortable bedrooms, and two well kept bathrooms. The outdoors is offering a stunning fenced backyard, lots of playground space for entertainment. Minutes to all major highways and shopping. This huge 2 acre property has a lot potential. A great opportunity act fast!

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.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,617
Status:
Active
MLS#:
938744
Type:
Single Family
Lot size:
2.3 Acres
Year built:
1995
A broker reciprocity listing Courtesy: eXp Realty 888-276-0630
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ADDITIONAL INFORMATION

Welcome to 65 Oxford Springs Road, Chester, NY a custom-built Country Contemporary set on a private, 2.3-acre hilltop. This property offers the perfect mix of privacy, space, and convenience, all just minutes from the NYS Thruway, local state parks, and about 50 minutes from NYC. Inside, the home features a bright, open floor plan with plenty of natural light. You’ll find rich hardwood floors, custom trim work, and impressive 26-foot ceilings that give the main living area a spacious, inviting feel. The living room centers around a striking stone fireplace and flows into a modern granite kitchen with an oversized island and stainless steel appliances ideal for both everyday living and entertaining. The home includes five bedrooms and four bathrooms, with a primary suite that features its own fireplace and a private balcony overlooking the peaceful surroundings. French doors off the dining area lead to a backyard deck that’s perfect for quiet mornings or hosting guests. A standout feature of this property is the two-story detached cottage (approx. 1,000 sq. ft.), offering endless possibilities an art studio, office, guest space, or creative retreat. Recent improvements include a new oil heating system with an above-ground tank. Please note: this home is located on a private road, approximately 0.6 miles from the main road. Experience the charm of country living with the comfort of modern design in this rare Orange County retreat.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,331
Status:
Active
MLS#:
937839
Type:
Condo
Year built:
1984
A broker reciprocity listing Courtesy: Century 21 E & M Williams Rlty 845-778-3543
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ADDITIONAL INFORMATION

3 bedroom 2.1 bath end unit, with 2 car garage! Community pool, tennis, playground. close to bus stop, pool and amenities. Easy access to highways Route 17 and the NYS Thruway.

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
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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.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,084
Status:
Active
MLS#:
935471
Type:
Condo
Subdivision:
Whispering Hills
Year built:
1984
A broker reciprocity listing Courtesy: Howard Hanna Rand Realty 845-928-9691
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ADDITIONAL INFORMATION

Discover the perfect blend of comfort, convenience, and community in this 2-bedroom, 1-bath end-unit townhouse. Situated in a quiet corner of the neighborhood, this home offers extra privacy and natural light, along with the added benefit of an attached 1-car garage for secure parking and storage. Inside, you'll find a thoughtfully designed layout that maximizes space and livability - ideal for first-time buyers, downsizers, or anyone seeking a low-maintenance lifestyle. But this home is more than just what's inside. Located in a commuter-friendly community, you'll have access to an impressive selection of amenities designed to enhance your daily life: Two (2) sparkling swimming pools perfect for cooling off in the summer; Two (2) tennis courts, plus basketball and handball courts to keep you active; A fully equipped fitness center just steps from your door; Two (2) playgrounds for little ones to enjoy; and two (2) dedicated dog runs - a dream for your furry friends. Whether you're relaxing poolside, getting in a workout, or taking a stroll with your pup, this community truly offers something for everyone.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,302
Status:
Active
MLS#:
933779
Type:
Single Family
Lot size:
0.97 Acres
Year built:
1910
A broker reciprocity listing Courtesy: SHAHAR Management LLC 845-476-7101
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ADDITIONAL INFORMATION

Listed on the National Register of Historic Places in the Sugar Loaf Historic District, this stunning Victorian is a Circa 1910 Sears Roebuck Kit Home (#118 The Clyde). Not only is this your dream home located in beautiful Sugar Loaf, NY, it is also zoned for extensive commercial use. Just a 1-minute walk to the quaint Sugar Loaf Arts & Crafts Village, cafes and Sugar Loaf Performing Arts Center. Enjoy morning coffee on the porch and head to work in your office with custom built library and pocket doors on the first level. With a whole house generator on stand-by you never have to worry about a storm leaving you without power. Purchased by an artist this home has been extensively and lovingly restored in every possible way to enhance your living experience. There are custom moldings, central air, central vac system, pocket doors, Navian high efficiency tankless boiler, 50-year shingle roof in 2006, a custom copper Yankee gutter system, and more. Love to cook-the kitchen has beautiful natural lighting and plenty of space for family and friends. When you walk through the door you will know this house is different from the rest and stands above. Just an hour to NYC! USDA Eligible.

Beds:
6
Baths:
3.00
Sq.Ft.:
3,066
Status:
Active
MLS#:
925401
Type:
Single Family
Lot size:
0.55 Acres
Year built:
2003
A broker reciprocity listing Courtesy: eRealty Advisors, Inc 914-712-6330
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ADDITIONAL INFORMATION

Discover refined living at 3 Grand View Terrace, a beautiful 6-bedroom, 3-bath Colonial in Chester's sought-after Valley View Phase II subdivision. This impressive home boasts 3,066 sq ft of living space, with a full walkout basement and an attached 2-car garage. Built in 2003, it features central air and forced air heat. Relax by the fireplace or enjoy the outdoor space on the 0.55-acre lot. This location offers easy access to transportation, shopping, dining, and recreation, Enjoy the peace and quiet of a neighborhood known for its excellent schools and community involvement.

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


The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of the Multiple Listing Service of Staten Island. Real Estate listings held by brokerage firms other than Xome are marked with the Broker Reciprocity logo and detailed information about them includes the name of the listing brokers. The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. 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. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2026, Multiple Listing Service of Staten Island. All rights reserved.



Chester Real Estate

Chester is located in New York. Chester, New York has a population of 12,477. Chester 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 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 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

    $382,000
    17.6%
    change since last quarter
  • # Active listings

    54
    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

City County
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