The agencies at Chester
These agencies offer a selection of luxury properties vente at Chester. Feel free to contact them for personalized assistance.
The Conklin House: A Masterpiece of History & Modern Luxury. Experience the perfect blend of early 20th-century charm and 21st-century comfort. A classic 1908 Queen Anne Victorian stands as a commanding presence at the edge of the historic Village of Sugar Loaf. The home has always been used residentially but zoning permits commercial usage as well. Originally ordered from the Sears & Roebuck catalogue and delivered by rail, this pre-fab pioneer was famously the first electrified home in the area. The current owner has meticulously performed a full-scale reconstruction, ensuring the home is entirely turn-key while honoring its heritage. The home features modern infrastructure with all-new mechanical systems, walls, and energy-efficient windows. Its preserved character is astounding. Every period molding, the original grand staircase, panel doors and authentic flooring have been salvaged and restored. The architectural heritage is monumental as it features its signature steeply pitched hipped roof and a dominant front-facing gable that defines its Victorian silhouette. Built for Howard Conklin—the local postmaster/general store owner—and later by his son, Dr. Roger Howard Conklin, this residence has been a cornerstone of the community for over a century. It represents a rare opportunity to own a piece of Hudson Valley history without the burden of historic maintenance. The lifestyle in Sugar Loaf and Chester, NY is refreshing, especially to New Yorkers getting away from the city. Nestled in a tight-knit arts and crafts hamlet, one is steps away from 18th-century buildings housing artisan studios, galleries, and boutique eateries. And there is rich Outdoor Adventure to take advantage of too! The area has direct access to the 18-mile Heritage Trail for biking and walking, plus proximity to Goosepond Mountain State Park and the Birnberg Nature Preserve. Its rural serenity offers a quiet, creative lifestyle surrounded by majestic mountains and rolling meadows, all while being part of a bustling weekend destination. Driving to and from the Conklin House to NYC is about 1 hour and 15 minutes and using mass transit a little longer. This is more than a house; it is a storied landmark reimagined for the modern connoisseur. Nothing compares to the character, lifestyle and wilderness that the Conklin House has to offer.
…By Ellis Sotheby's International Realty
18 Acres Property Available Together For The First Time! Calling all builders, investors, and primary users. This sale is comprised of adjacent parcels totaling 18 acres in Woodbury, New York. Currently configured as an income-producing four-family property, and a newly constructed single-family structure with detached equipment/vehicle storage garage. Ideal for subdivision or use under current configuration. Approved variance for commercial usage for street-adjacent section of parcels allows for future mixed use development. Property can be delivered vacant or with tenants in place per purchaser's preference. Located within 1.5 miles from major throughways and Woodbury Common Premium Outlets.
…By Annonceur International
Colonial Masterpiece - This one-of-a-kind Hudson Valley residence artfully combines authentic, historic character with flawless contemporary design set on a bucolic, level parcel. The c. 1790’s antique colonial portion of the home features a timeless natural stone facade, standing seam roof, and welcoming red front door evoking true period charm. An architecturally inspired contemporary wing clad in cedar was added in the 1980s, creating a spacious, chic, light-filled interior, and a seamless blend of old and new. The property is punctuated outside with towering pines and mature, perennial plantings. The antique portion of the home maintains beamed ceilings and crafted wood details in the main room, and it flows to the soaring, light-filled section, on two levels. On the main level, the large contemporary living room, and an open-concept kitchen and dining room are designed for modern, sophisticated living. This open main living room has slider doors to the pool area and sitting areas at the back of the home. A home office, a large entry foyer, a den and full bath round out the main level. Upstairs a luxurious sun-soaked primary suite with a sitting room, serves as a private retreat along with three other cozy bedrooms and a hall bath in the antique portion of the home. Original details of stonework, wood accents, and early craftsmanship - are preserved and accented throughout, while modern amenities bring comfort and ease. With four bedrooms, three full baths, and a lower level home gym, this exceptional property offers design aesthetic and daily utility in one. The outdoor spaces are a true escape. At the rear of the home, an expansive deck and stone patio surround a sparkling in-ground pool, cloistered into a private alcove and framed by a beautiful cedar pergola. The sprawling rear lawn is perfect for outdoor entertaining or imaginative uses. A detached 2-car garage has bonus space above, perfect for a studio, more exercise space or further creative pursuits. The property offers a viewshed of Highland Lakes State Park with over 3,000 acres of preserved woodlands, trails, and lakes for year round recreation. Ideally located in central Orange County in NY’s Hudson Valley, this special home is about 90 minutes from New York City and approximately 35 minutes to the Catskills and Shawangunks. The region is renowned for its leading cultural and entertainment institutions, medical and educational institutions, vibrant farm-to-table dining, the Shawangunk wine trail, Bethel Woods, Storm King Art Center and more. Completely unique and stunningly beautiful in every aspect, here is a one of one lifestyle opportunity, not to be missed.
…By Ellis Sotheby's International Realty
Extensively updated, this residence offers a rare combination of smart home technology, energy efficiency, and thoughtfully designed interior spaces. The home is equipped as a fully integrated smart property, featuring professional-grade WiFi, smart lighting, smart locks, upgraded outlets, and connected appliances, allowing for seamless control of lighting, climate, security, and daily living. A geothermal ground-source heat pump provides efficient year-round heating and cooling, maintaining consistent performance in all seasons. Solar energy supports the home’s electrical usage, creating a more energy-conscious and cost-efficient living environment. These systems are enhanced by closed-cell spray foam insulation, a high-efficiency hybrid water heater, and a fully replaced well water system, delivering long-term reliability and performance. The kitchen features a full KitchenAid appliance suite, including an induction stove, along with an LG internet-connected washer and dryer. Bathrooms have been fully renovated to a high standard, including a primary bath with a Japanese soaking tub, walk-in shower, Toto bidet suite, integrated audio, and premium finishes. The ensuite bath features an oversized walk-in shower with rainfall showerhead and Toto fixtures. Updated plumbing and high-quality materials are carried throughout. Bedrooms have been rebuilt from the studs, including custom European-style built-in wardrobes in the primary, offering clean design and exceptional storage. Additional interior upgrades include new flooring, fresh paint, removal of baseboard radiators, and a fully redesigned mudroom. Exterior updates include fully rebuilt decks (composite and pressure-treated), exterior repainting, garage roof replacement, and thoughtfully designed landscaping with native and seasonal plantings. A premium European hot tub with integrated sound system enhances the outdoor living experience (available separately). The property also features a detached 2-car garage with loft storage, smart locks, an electric vehicle charging port, and a whole-house generator, supported by an upgraded 200-amp electrical panel. Set on nearly 2 acres at the end of a quiet cul-de-sac, the home backs directly to protected forest land, offering exceptional privacy, natural surroundings, and direct access to extensive trail systems.Positioned to take full advantage of its surroundings, the front of the home captures expansive, multi-layered views of the Hudson Highlands, where four distinct mountain ranges unfold into the distance. This elevated vantage point creates a striking sense of depth and tranquility, offering a natural backdrop that evolves with every season. Significant investment has been made in both infrastructure and interior improvements, providing a move-in-ready home where major systems and upgrades have already been completed. Conveniently located in Cornwall, the property is just minutes from the United States Military Academy at West Point and the dining and arts scene of Beacon. Woodbury Common Premium Outlets are also within a short drive. Approximately 60 miles from New York City, with access to Metro-North Railroad via Beacon offering direct service to Grand Central Terminal, the location provides a practical connection for commuters while maintaining a quiet residential setting. A rare opportunity to own a well-positioned home that blends modern efficiency with one of Cornwall’s most compelling natural outlooks.
…By Four Seasons Sotheby's International Realty
Rare opportunity to purchase two adjoining properties in Greenwood Lake’s Indian Park community. Known for its sweeping mountain and lake views, 2 private beaches (1 for swimming and 1 where owners can store and launch kayaks, canoes, row boats, etc.) club house and authentic charm, Indian Park celebrates lake life at its best. Located on the west shore of Greenwood Lake, sunrise is a spectacle to be seen and colors unfold like a Jasper Cropsey painting. This Hudson River School painter found inspiration here and his lasting landscapes of Greenwood Lake are testament to the natural beauty which abounds. 173 Brook Trail captures the essence of this authenticity with its stone fireplace, sunroom office with sweeping views, stargazing balcony and expansive deck space for grilling, lounging and recharging in the Swedish outdoor sauna. Complete with 3 bedrooms, a remodeled kitchen with quartz countertops, recent upgrade of central air and spilt units, and a brand-new furnace (just installed this March) the house is move-in ready or turn-key as a STR, which it is currently permitted for. Included in the sale is neighboring 179 Brook Trail. Previously home to a seasonal cottage that was recently removed, the .65 acre-property has an existing well and septic. Architectural plans for a proposed new home are available.
…By Ellis Sotheby's International Realty
Coming Soon. On Market Date: 6/12/2026. Set in the heart of the river village of Cornwall-on-Hudson, this stately Colonial offers a rare opportunity to enjoy the very best of the Hudson Valley lifestyle. One Taft Place is just moments from the village center with its restaurants, cafes, galleries, boutique shops, and scenic parks along the Hudson River. Its prime location gives easy access to the greater Hudson Valley's wide array of celebrated amenities. With its brick facade, elegant curved center hall staircase, and classic architectural lines, the home has a stately presence. Built in 1973 by its then original builder-owner, it offers approximately 3,800 square feet of living space across four levels, from the finished lower level to the top-floor observatory, creating a spacious and versatile layout suited for both everyday living, entertaining and extensive options for work-from-home with a view! On the main level, the formal living and dining rooms with bay windows are bathed in south-easterly light. There's a natural, easy flow with a welcoming family room with built-ins, and a den with wet bar. The eat-in kitchen opens to a multi-level rear deck surrounded by mature trees and mostly level back yard. Here too a main-level suite with full bath is ideal for guests, extended family, or home office use. The home offers a true four-bedroom layout with the opportunity to live as a 5 to 6 bedroom residence through the additional bonus and suite spaces. The primary suite is large and offers great privacy, twin closets and dual showers! The third-floor observatory provides a unique and inspiring setting for work or relaxation, featuring a seasonal view of the Hudson River. The finished lower level includes recreation and workspace areas with walk-out access. Additional features include a two-car, attached garage (with new door), and ample driveway / off-street parking. Ideally positioned to enjoy the surrounding Hudson Valley landscape, the location is near to hiking at Storm King Mountain and Black Rock Forest, as well as the iconic Route 218, a renowned scenic drive winding along the mountains above the Hudson River. The United States Military Academy is just minutes away. Offering exceptional location, scale, flexibility, and forward potential, this is an opportunity to enjoy immediately or to thoughtfully update with a contemporary aesthetic. A classic colonial not to be missed, all within one of the Hudson Valley’s most desirable and idyllic settings.
…By Ellis Sotheby's International Realty
A rare opportunity to enjoy space (aprox. 2,300 sq ft) , privacy, and flexibility at an attractive price point in one of Glenwood's most desirable neighborhoods. Ideally located approximately half a mile from the Appalachian Trail Boardwalk and close to recreation, shopping, and schools, this property offers a unique blend of convenience and tranquility.This spacious three bedroom, three full and one half bath home offers approximately 2,500 square feet of living space set on a private lot. The versatile layout features multiple living areas, generously sized rooms, hardwood flooring, and crisp crown moldings throughout. A first-floor suite provides exceptional flexibility is ideal for guests, extended living, a home office, or whatever best suits your needs.The kitchen opens to a bright breakfast area with sliding doors leading to an oversized deck overlooking the backyard and in-ground pool, creating an ideal setting for outdoor dining and entertaining. A large family room addition enhances the home's living space with abundant natural light and room for gatherings.Upstairs, you'll find three well-appointed bedrooms, including a spacious primary suite complete with an en-suite bath and walk-in closet. Home is being sold as is.
…By Kienlen Lattmann Sotheby's International Realty
Nestled on the serene slopes of Buckberg Mountain, this beautifully maintained side-hall Colonial carries the soul of the Civil War era into modern living. The open floor plan flows naturally through sun-filled spaces adorned with rich hardwood floors throughout, mostly original finishes, this home has been lovingly cared for over the years. Upstairs offers four spacious bedrooms, while the main level features a warm family room with a wood-burning fireplace — perfect for cozy evenings in. A legal accessory apartment with its own private entrance provides often much needed flexibility for extended family, while remaining accessible through the main home if desired. Step outside to your own private paradise. The expansive 1.34-acre lot offers a level, grassy lawn with space for a pool, swing set, or entertaining, plus a back deck and lightly wooded areas that create a peaceful, naturalist retreat. Privacy abounds. An electric car charger adds a modern convenience to complete the package. A full unfinished basement offers tremendous storage or future potential. Located in the charming hamlet of Tomkins Cove, you'll enjoy the best of both worlds — a green, safe, and serene community with easy access to New York City just 33 miles away, roughly 35–40 minutes by car. Commuters can also reach the city by bus or train. The surrounding Rockland County and Stony Point area offer wonderful activities including hiking at Harriman State Park, exploring the Stony Point Battlefield, waterfront fun at the Hudson River, local farmers markets, and vibrant dining and shopping nearby. Come and see, an opportunity to own a piece of history in one of the Hudson Valley's lovliest settings.
…By Ellis Sotheby's International Realty
Just 60 minutes from Manhattan, this exceptional Hudson Highlands retreat offers a rare combination of architectural character, protected natural surroundings, and direct access to some of the region’s most celebrated outdoor destinations. Set on 13 private acres across two separate lots—including a second vacant, buildable parcel—the property is tucked away on a quiet dirt road known for its strong sense of community, minimal traffic, and remarkable tranquility. Bordering the 8,000-acre Hudson Highlands State Park Preserve with more than 70 miles of trails, the estate enjoys a setting that feels both deeply secluded and endlessly connected to nature. Outdoor recreation begins at your doorstep. The property features its own trail network and private trailhead connecting directly to the Appalachian Trail, offering true hike-on, hike-off access. Walk to nearby lakes, explore the trails of the Russel Wright Design Center, hike to Anthony’s Nose, or cycle directly from the property to Bear Mountain, one of the Northeast’s premier road biking destinations. A seasonal stream, private campsite, and campfire area further enhance the experience of living immersed in the landscape. Designed by noted Hudson Valley architect Frank Dushin, the residence blends the warmth and craftsmanship of the Arts and Crafts tradition with the clean lines and thoughtful spatial design of modernism. Dramatic exposed beams, natural materials, and a striking sunken living room create spaces that feel both timeless and distinctly connected to their surroundings. The home has been extensively renovated, including a complete reimagining of the primary suite and bath, beautifully updated bathrooms throughout, and a thoughtfully designed laundry room. Two fireplaces, a screened porch, and expansive views of the surrounding gardens and woodlands create inviting spaces for every season. Outside, more than two decades of garden design by a beloved local horticulturist have shaped the landscape into a living extension of the home. Mature plantings, curated garden rooms, and woodland paths unfold across the property, creating beauty and interest throughout the year. A separate wellness pavilion includes a gym, steam room, dedicated shower facilities, outdoor hot tub, and connections for a future sauna, while a detached two-bedroom guest house with its own kitchen offers comfortable accommodations for family and visitors. Rarely does a property combine architectural pedigree, buildable acreage, direct trail access, protected parkland, established gardens, and resort-style amenities so close to New York City. This is a true Hudson Highlands sanctuary—private, peaceful, and connected to the landscape in every direction.
…By Four Seasons Sotheby's International Realty
Whispering Pines is a turn-of-the-century home with stunning Hudson River views on three acres of rolling lawns, mature plantings, and a natural, stone-carved pool. Awaken to sunrises over the river! This property is an extraordinary opportunity for nature lovers seeking peace and privacy. With two state parks practically in your backyard, hiking, kayaking and swimming in mountain lakes is just a stone's throw away. In addition to the original 1900’s house, the property has a garage with loft that could serve as a studio. Just 45 minutes to the George Washington Bridge and 20 minutes to the Metro North Station in Garrison, this property offers breathtaking views, serene surroundings, and ample acreage to create your own oasis. Possible subdivide with easement. Property is being offered As Is.
…By Ellis Sotheby's International Realty
A true retreat for outdoor enthusiasts! Enjoy lakefront living on a private powerboat lake, tucked into a peaceful, deep-water cove. This inviting home features a warm and welcoming great room with vaulted beamed ceilings and a cozy brick fireplace with insert. Updated kitchen with center island breakfast bar is perfect for entertaining! Relax in the sunroom or on the deck and enjoy tranquil lake views. Featuring two bedrooms and a mini loft with expansion potential offering max flexibility. Step right from your backyard to your dock and spend your days fishing, swimming, jet skiing, or cruising the lake by boat with membership in UGLPOA. In winter, embrace ice fishing and the beauty of the season right outside your door. A large lakeside outbuilding is ideal for storing gear or creating the ultimate hangout space. Enjoy year-round activities and community events through the lake association, making every season something to look forward to. Live where every day feels like a getaway!
…By Prominent Properties Sotheby's International Realty
Spring is here and so is your next home! This stunning single-owner colonial has been lovingly maintained since it was built in 2007 — and the moment you walk in, you'll feel the difference that true pride of ownership makes. At 2,092 square feet, three bedrooms, and two and a half baths, this classic colonial checks every box while somehow still feeling like a hidden gem. Inside, the open and flowing floor plan is one of this home's standout features — airy, connected, and bathed in natural light, with high ceilings throughout that give every room a sense of space and elegance, including in the unfinished basement, ready for your vision. The wet bar off the dining room sets the tone for easy entertaining, and main floor laundry means the little things in life stay simple. Out back, a fully fenced yard gives you privacy, peace of mind, and the perfect setup for summer gatherings, pets, and everything in between. The primary suite is genuinely special...a nice sized bedroom plus a large bonus room with a bay window, the en suite bath offers double sinks, a stand-up shower, and a big jacuzzi tub that makes any day feel like spa day. The covered front porch is the kind of charming colonial detail that turns a house into a home — picture yourself there with a coffee as the neighborhood wakes up. And the location? It doesn't get better than this. Garnerville sits in the heart of the Lower Hudson Valley, minutes from the legendary trails of Harriman State Park and Bear Mountain — thousands of acres of breathtaking scenery, waterfalls, and year-round adventure practically at your doorstep. Catch live music at local festivals, browse the Hudson Valley's beloved farmers markets overflowing with local produce, flowers, and artisan goods, or explore the eclectic dining scene — some restaurants even accessible by boat along the Hudson. All of this, just 29 miles from the George Washington Bridge. The commute is easy. The lifestyle is extraordinary. Come see it before someone else does!
…By Ellis Sotheby's International Realty
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These agencies offer a selection of luxury properties vente at Chester. Feel free to contact them for personalized assistance.