Chester Homes with Heated Garage Parking features

Welcome to Chester, New York – a hidden gem nestled in the heart of Orange County! Known for its picturesque landscapes and vibrant community spirit, Chester offers the perfect blend of small-town charm and modern conveniences. Surrounded by the stunning natural beauty of the Hudson Valley, residents enjoy a wealth of outdoor activities, from hiking and biking in the nearby mountains to fishing and boating on the serene lakes. Chester is also home to a lively arts scene, rich history, and a variety of local shops and eateries that give the town its unique character.

For those considering making Chester their home, you’ll find a selection of delightful properties that cater to a range of lifestyles. One of the standout features of many homes in this area is the inclusion of heated garage parking. Imagine stepping out of your car into a warm, cozy garage on those chilly winter mornings! Heated garages not only provide comfort but also protect your vehicle from the harsh elements, ensuring it remains in pristine condition year-round.

With Chester's welcoming community, excellent schools, and easy access to nearby cities like New York City and New Jersey, it’s no wonder that this charming town is becoming a sought-after destination for families and individuals alike. Whether you're looking for a quaint cottage, a spacious family home, or a modern retreat, Chester has something for everyone. Come discover the warmth and allure of Chester, where your dream home awaits!

Newest Chester Homes with Heated Garage Parking features

$1,195,000

4 Beds ⋅ 4 Baths ⋅ 1010585 MLS

Welcome to a one-of-a-kind Arts and Crafts style sanctuary where timeless craftsmanship meets modern luxury. Tailored for the discerning buyer or avid automotive enthusiast, this exceptional property features an expansive multi-car garage designed to accommodate prized vehicle collections, a workshop, or custom storage needs. Located in the Town of Chester, this 4,281-square-foot estate masterfully blends timeless architectural detail, rich natural textures, and modern sophistication. Exceptional artistry is on display throughout, highlighted by solid wood doors, dual staircases, striking red oak flooring with Mahogany inlays, and radiant-heated floors across the entire main level. Formal living and dining spaces framed by soaring floor-to-ceiling windows flow effortlessly onto a sweeping bluestone patio, while the chef's kitchen and sunken family room with a rustic wood-burning fireplace lead to a covered outdoor patio and private fire pit area. The main-level primary suite offers a peaceful sanctuary with a gas fireplace, wrap-around covered Trex deck, and a spa-inspired bath with a vintage cast iron clawfoot tub. Upstairs, 3 oversized bedrooms—two with private en-suite baths—are complemented by a full walk-up attic and a bonus loft accessed via a spiral staircase. Enjoy the perfect mix of local charm and seamless transit. Located just minutes from the historic Village of Goshen, you’ll have quick access to boutique shopping, famed local dining, craft breweries, local wineries, and the scenic Orange Heritage Trail. Just 10 miles from Woodbury Common Premium Outlets and 60 miles from NYC, with immediate access to Route 17 (I-86), the NYS Thruway, Chester Park & Ride, and Harriman Train Station.

22 Goshen Road, Chester

$379,900

2 Beds ⋅ 1 Baths ⋅ 964090 MLS

Great new price! Come take a look at this 2 bedroom charmer with additional room offers potential 3+ bedrooms. Larger than it looks - need to see. 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. 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.

7 Hambletonian Avenue, Chester

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