Chester Homes with Washingtonville School district

Welcome to Chester, New York – a picturesque gem nestled in the heart of Orange County. Known for its breathtaking landscapes and vibrant community, Chester is a perfect blend of small-town charm and modern conveniences. With its rolling hills, lush greenery, and access to pristine lakes, this area offers an idyllic setting for families, outdoor enthusiasts, and anyone looking to embrace a tranquil lifestyle.

Chester is not just a place to live; it’s a community where neighbors become friends. The town boasts a variety of local shops, delightful eateries, and seasonal farmers' markets, making it easy to enjoy the best of local culture. The surrounding natural beauty provides ample opportunities for hiking, fishing, and exploring, ensuring that residents can take full advantage of the great outdoors.

For families considering a move, the homes within the Washingtonville School District are particularly appealing. This district is renowned for its commitment to educational excellence, offering a range of programs designed to foster student growth and achievement. Parents can feel confident knowing their children are receiving a quality education in a supportive environment.

Whether you're drawn to Chester's scenic beauty, its tight-knit community, or the outstanding educational opportunities available, this charming town has something for everyone. With a variety of homes to choose from, including cozy cottages and spacious family residences, Chester is the perfect place to call home. Discover the charm of Chester, where every day feels like a retreat, and your next adventure awaits just around the corner.

Newest Chester Homes with Washingtonville School district

$280,000

3 Beds ⋅ 1 Baths ⋅ 1016060 MLS

We are proud to introduce this cornerstone property, located within what was once a thriving enclave of artists. The same owner since 1946, this home and studio are part of a small collection of historic properties that helped define the character of the area. Now, an extraordinary opportunity awaits for the next steward to write the next chapter of this remarkable property. Originally built circa 1800, the home sits quietly within the landscape, its history unfolding through generations of thoughtful additions. Among them was a former general store, where horse-drawn carriages once stopped for dry goods and daily provisions, while the village blacksmith worked just across the way. From the road, passersby may never suspect what lies beyond. Behind its unassuming facade is a private and enchanting oasis, complete with expansive studio space that inspires creativity and retreat. The home itself is rich with period details that have been lovingly preserved through time. Wide-plank floors, beautifully patinated doors, burnished staircase railings, classic fireplaces, and a hidden back staircase all contribute to its authentic historic charm. An elevator was added for convenience to the 2nd floor. The studio still features the original general store counter and shelving, offering a rare connection to the property's past. The generous space lends itself to a wide range of creative pursuits, with a private retreat area tucked behind. Stone walls frame an intimate cottage garden, while the existing potting shed offers potential for expansion into a garage or workshop. This is more than a home—it's a piece of local history waiting to be reimagined. This weekend destination is set amid the rolling hills of Orange County, this property offers easy access to the Hudson Valley's most sought-after destinations, including Storm King Art Center, the artisan community of Sugar Loaf Arts and Crafts Village, wineries, orchards, hiking trails, and the outdoor recreation that has made the region a favored escape for New York City residents seeking space, creativity, and a connection to nature.

815 Craigville Road, Chester

$1,195,000

4 Beds ⋅ 4 Baths ⋅ 1010585 MLS

Welcome to an unparalleled expression of luxury living in the Town of Chester. Built in 2003, this custom-built Cape May/Colonial estate designed by award winning architect Larry Belk estate spans 4,281 square feet of meticulously designed living space, masterfully balancing grand entertaining spaces with intimate everyday comfort. From the moment you arrive, exceptional craftsmanship is on display—from the solid wood doors and dual staircases to the premium radiant-heated floors sweeping across the entire main level. The inviting foyer seamlessly transitions into the formal living and dining rooms, both framed by dramatic floor-to-ceiling windows, intricate crown molding, and striking red oak flooring with Mahogany inlays. Both formal spaces open directly to an expansive bluestone patio, offering an effortless indoor-outdoor lifestyle. At the heart of the home is a true culinary enthusiast’s kitchen, outfitted with oversized granite countertops, custom cabinetry, and a table-height center island. Immediately adjacent, a sunken family room anchored by a rustic wood-burning fireplace serves as the perfect gathering hub, featuring French doors that lead to a covered bluestone patio and a private fire pit area. Retreat to the main-level primary suite—a serene sanctuary complete with gas fireplace and French doors opening to a private, wrap around covered Trex deck. The spa-like primary bath boasts a vintage-inspired cast iron clawfoot tub, a walk-in shower, and dual vanities, all complemented by a massive walk-in closet. A dedicated laundry room completes the main level. Upstairs, discover a versatile bonus loft accessed via a spiral staircase, a full walk-up attic, and three generously sized bedrooms—two of which feature private en-suite baths and walk-in closets. The lower level is an enthusiast’s dream. Beyond vast storage capabilities, this floor houses a dedicated wine-making room and provides direct access to an extraordinary, pristine multi-car garage featuring professional epoxy flooring. A true masterpiece of design, utility, and sophistication. Enjoy effortless travel with immediate access to Route 17 (I-86) and the NYS Thruway, while mass transit options like the Chester Park & Ride and the Harriman Train Station make commuting a breeze. Located just 60 miles from NYC, you can enjoy the peace of the suburbs and be in the city in just over an hour. Unbeatable location for entertainment, dining, and shopping! You are 10 miles from the world-famous Woodbury Common Premium Outlets. Explore Chester’s vibrant local food scene, steps from local restaurants, craft breweries, and renowned local wineries. Outdoor enthusiasts will love the proximity to the scenic Orange Heritage Trail. Exceptional location, maximum convenience, and a perfect place to call home!

22 Goshen Road, Chester

$499,000

4 Beds ⋅ 3 Baths ⋅ 997559 MLS

Nestled on a quiet road off the beaten path, this serene 4-bedroom, 2.5-bathroom Colonial offers the perfect blend of secluded tranquility and commuter convenience. The main level features a traditional layout with a spacious living room, formal dining room, and a cozy recreation room perfect for relaxing. The functional eat-in kitchen serves as the heart of the home, while all four bedrooms are tucked away on the second floor for maximum privacy. Additional features include a two-car garage and a full unfinished basement providing ample storage space. Step outside to explore your own wooded oasis, complete with a concrete patio for entertaining, and private path leading to a picturesque stream flowing under a bridge. Enjoy the peace of a nature-filled lot with the comfort of nearby neighbors, all while being close to Chester’s business district and major transit routes.

63 Hubshop Road, Chester

$1,725,000

4 Beds ⋅ 3 Baths ⋅ 961236 MLS

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.

20 Goshen Road, Chester

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