Chester, NY Homes for Sale with Garage

Set on 10 private acres with sweeping mountain views from nearly every room, 69 Cedar Pond is a five-bedroom, eight-bath estate that exemplifies expansive design and contemporary style. The striking A-frame architecture, double-height windows, and soaring ceilings create dramatic, light-filled interiors where every angle frames the surrounding landscape and sunsets.A three-story entry

Emily Iason Four Seasons Sotheby's Int.

The one you don't to miss. 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

Alexander Fayn Prominent Properties Sotheby's

Welcome to your private, wooded oasis! This charming home perfectly blends convenience with comfort, featuring an ideal layout for multi-generational living or guests with two bedrooms and a full bathroom on the main floor. A cozy wood insert is the heart of the main living space, creating both warmth and a wonderful ambiance on chilly evenings. Beyond the existing bedrooms, there is additional

Luanne McGann Century 21 Full Service Realty

Step into this newly renovated contemporary ranch, where comfort meets value on 6.3 acres of peaceful living. Featuring 4 spacious bedrooms and 3.5 bathrooms, this home has been beautifully renovated with new plumbing, spotlights, flooring, kitchen, painting, and full wiring for a camera and security system. Enjoy a large eat-in kitchen, formal dining room, cozy family room, and a bright attic

Chaim Weiss Exit Realty Venture

One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space.Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk

Ernie Acampora River Realty Services, Inc.

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

Frank Golio Howard Hanna Rand Realty

A truly rare opportunity to secure over two acres of prime land in the highly desirable and rapidly appreciating town of Chester. This charming property isn't just a home; it's a foundation for your future and a strategic long-term investment. Set on a sprawling 2.1+ acre lot, this property offers the space and privacy that is simply unmatched in today's market. The current single-level structure

Nikki Grzegorzewski Keller Williams Realty

Stunning Chester Home with Pool, Pond & Private Backyard Oasis! Discover your own private retreat in this meticulously maintained 3-bedroom, 2.5-bath home in Chester. Perfectly positioned for privacy on a scenic lot featuring its own backyard pond, this property offers a rare combination of comfort and outdoor amenities. Step inside to a bright and airy main level where hardwood floors connect

Christine Koenig Keller Williams Realty

Welcome to an extraordinary 4,400+ square foot residence in the coveted Warwick School district, where luxury and lifestyle converge to create the ultimate entertainer’s dream. This meticulously maintained and thoughtfully updated home offers breathtaking panoramic views, inviting you to unwind in the serene front atrium or the sun-drenched sunroom at the rear. Step inside to discover a

Hilary Ryan Goldman Howard Hanna Rand Realty

Thoughtfully repositioned with a nearly $15,000 price adjustment makes this Country Woods colonial an unbeatable value! Now priced to allow for updates while securing a prime location, generous living space, a beautiful setting, and room to add your personal style. Country Woods is one of Chester’s most sought-after neighborhoods. This handsome Colonial sits on 1.7 landscaped acres and offers

Kimberly Starks Howard Hanna Rand Realty

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

Elizabeth Broderick Tuxedo Hudson Realty Corp

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

Debbie Goldstein Howard Hanna Rand Realty

Set back on a quiet street, just steps from downtown Sugar Loaf is this large home on almost an acre. Walk into the open living room and dining room, open to the kitchen with stainless steel appliances. The primary bedroom has access to the back deck, perfect for sipping your morning coffee overlooking the large peaceful backyard. Two additional bedrooms and a full bath complete the main floor.

Kimberly Corkum Keller Williams Realty

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.).

Karen Gauvin Our House Real Estate Group

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

Jie Liu Keller Williams Hudson Valley

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

Joseph Rosenfeld Flag Realty Group

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.

Joseph Mendlowitz eRealty Advisors, Inc

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

Jennifer Gold RE/MAX Benchmark Realty Group

A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This will truly be a lovely property with land, privacy and wonderful mountain views! This modern farm house cape features over 2,600 sq ft. and is completely CUSTOM and DELIVERED TURN-KEY ... build this home, or bring your own dream plans/ideas! This ONE LEVEL living

Karen Gauvin Our House Real Estate Group

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

Bente Brown John J Lease REALTORS Inc

Welcome to this charming Colonial set in the desirable Trout Brook ll subdivision of Monroe. This lovely home offers the perfect balance of privacy and convenience—just minutes to local shops and the village, and a short 10–15 minute drive to all major highways. Plus, you're only an hour from NYC, making it ideal for commuters or weekend getaways. Outdoor enthusiasts will love the close proximity

Lauren Kelly Howard Hanna Rand Realty

Big price reduction! Come see it before it's gone. Nice end unit 3 bedroom 2.5 bath condo with 2 car garage in whispering hills. Primary bedroom with private full bath and 2 nice size extra bedrooms plus a hall bath on the 2nd floor. Warm up on those cold nights with the fireplace in the living room. Enjoy a quiet moment on your private patio sipping your coffee. Great location with playground

Darlene Provino Century 21 E & M Williams Rlty

Discover a rare opportunity to own a one-of-a-kind estate set on 53 sprawling acres in the heart of Chester, NY—perfectly suited for luxury living, farming, or future development with subdivision potential. This impressive property features a 3-car garage with 10-foot doors, outdoor wood-burning furnace, and two 250-gallon oil tanks for efficient heating.Nature lovers and hobby farmers

Ramanjit Dhanoa eXp Realty

Views abound from this stunning colonial in the Warwick Ridge Sub-Division. Don't miss out on this custom built colonial.includes Chefs kitchen, quartz counters, extensive trim package, custom tile, hardwood the worksAccepted Offer 12/1

Robert Valentine BHG Real Estate Green Team

Welcome in to this beautifully maintained 3-bed, 2.5-bath townhouse offering the perfect blend of comfort, space, and convenience. The main level welcomes you with gleaming hardwood floors and a formal dining room—ideal for gatherings and everyday meals alike. The bright, spacious living areas flow effortlessly, creating a warm and inviting atmosphere.Upstairs, the primary bedroom features

Brittany Barry HV Premier Properties Realty