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
69 Cedar Pond Lane, an Chester estate capturing mountain views. Offering great living, proven Airbnb/rental potential, and extensive recent upgrades, this expansive home spans 3 fully finished levels. The sun-drenched main level features soaring skylights, picture windows, an open living/dining area with wood-burning fireplace, and a chef’s kitchen with new countertops, custom backsplash, breakfast bar, dining nook, wine rack, new refrigerator, and beverage fridge. Two bedrooms and 2.5 baths complete the level, plus walkout access to a large patio with outdoor bar, fireplace, and lounge area. Upstairs, the luxurious primary suite boasts mountain views, walk-in closet, and spa bath with dual vanities, soaking tub, shower, and private water closet. A separate in-law apartment offers three bedrooms, second kitchen, living room, updated finishes, media center, and private patio access. The walkout lower level offers a spacious recreation area, kitchenette, Airbnb-ready bedroom, laundry room, half bath, flex room, and hidden finished room behind a custom bookshelf with full bath—ideal as a speakeasy, lounge, office, gym, or studio. Outside, enjoy the private hot tub, fire pit, children’s playset, and multiple seating areas. The yard is scoped for an inground pool, with renderings available. Recent improvements include dual water heaters and HVAC upgrades (2025) and a roof replacement around 2022. A truly versatile property with space to live, entertain, generate income, & expand.
…By Prominent Properties Sotheby's International Realty
Set on nearly three acres in the heart of Warwick’s historic village, Breckenridge is a commanding example of Greek Revival architecture—its stately brick facade, soaring columns, and symmetrical proportions echoing the grandeur of a bygone era. Built in 1911, the residence spans over 6,200 square feet across three levels, offering six bedrooms, five-and-a-half baths, and a wealth of original details including seven fireplaces, cathedral ceilings, and a formal dining hall and library. The home’s architectural elegance is matched by its thoughtful layout, featuring a gourmet kitchen with gas range and pantry, impressive center hall with grand staircase, and elevator access. Add your own touches to this charming estate to bring back to full glory. This estate was built for Morris Rutherfurd, a prominent figure in Warwick’s early 20th-century social and industrial landscape. Rutherfurd, served as president and general manager of the Lehigh & Hudson River Railroad and resided in Warwick until his death in 1944. His legacy reflects the influence of the Gilded Age—a period marked by opulence, industrial expansion, and architectural experimentation. The home’s scale, craftsmanship, and stylistic choices are emblematic of that era’s desire to blend classical European aesthetics with American ambition. Outside, the property continues to impress with a three-car garage, long private drive accommodating up to 20 vehicles, and a fenced, in-ground pool with pool house. Sprinkler systems in both front and rear gardens ensure year-round lushness, while the partly wooded grounds offer privacy and serenity just moments from Main Street. With its rich historical roots and timeless design, this mansion is not just a residence—it’s a living chapter of Warwick’s architectural and cultural heritage. Warwick, New York offers a rare blend of small-town charm, cultural richness, and natural beauty that appeals to both weekenders and full-time residents. Its historic village center is a walkable haven of 19th-century architecture, boutique shops, art galleries, and locally owned restaurants, creating a vibrant yet intimate atmosphere. The community thrives on connection, with seasonal festivals like Applefest, weekly farmers markets, and summer concerts that bring neighbors together. Nature lovers enjoy easy access to the Appalachian Trail, Mount Peter for skiing and hiking, and nearby Greenwood Lake and Wawayanda State Park for boating, fishing, and birdwatching. Recreational amenities include golf courses, parks, and playgrounds, while agritourism flourishes at local orchards, wineries, and creameries such as Pennings Farm and Bellvale Farms Creamery. Warwick also nurtures a strong creative spirit, with cultural institutions like the Warwick Historical Society and a drive-in theater that’s been entertaining locals since 1950. Dining and shopping are elevated yet personal, with standout spots like Grappa Ristorante, Fetch Bar & Grill, and a variety of artisanal boutiques. Altogether, Warwick offers a lifestyle that’s both refined and rooted—perfect for those seeking a deeper sense of place. Conveniently located 60 miles from New York City, less than 90 min drive. Also available is direct bus service to Manhattan via NJ Transit. Ideal for any weekender or commuter.
…By Chapin Sotheby's International Realty
Labors of love are the best kind. They’re ones that carry projects further than any fuel can. At just 60 miles northwest of NYC, this bucolic equine estate served as a private polo field, equestrian center and most importantly a place to live within a landscape that could just as easily be the fields of France or Orange County. When purchased in 2011 the current owners enlisted Jeff Wilkinson, R.A to complete an extensive historic renovation and restoration project that both reimagined and preserved the architectural integrity of this 1910 farmhouse. Most notably, hand-hewn beams were uncovered and the living room ceiling opened up to create a dramatic space that spans from front to back of the house and flows seamlessly to the outdoors through the French doors that lead to the bluestone patio, pool and rolling fields. The kitchen was also updated complete with a La Cornue stove that now takes center stage. Designed as the hub of the house for preparing meals and entertaining, the kitchen flows to the dining room and leads to the screened in sunroom for panoramic meals made for lingering amongst the landscape. The stone basement was also finished as part of the renovation and serves as a family room with both an office nook and extra space for guests. On the second floor, dormers were added to bring more natural light into the upstairs bedrooms. The owners also purchased surrounding parcels to add to the existing acreage. The total is now 80.4 acres which provides an array of opportunities for further development. Outbuildings include a 10-stall barn with tack room, work room, bathroom, washer and dryer and apartment for staff or a clubhouse, as well as a large garage/barn for parking or equipment storage. The property also features a 550-ft by 220-ft crusher dust arena and track, a 300-yard by 130-yard polo field, a 6-horse walker with roof and variable speed and 2 run-in sheds. Wooded and open trails meander throughout the property offering the space to slow the pace, recalibrate, and connect with the landscape for a return to a natural circadian rhythm. Revel in the raw textures of the trees and fields as far as the eye can see and soak in the sun as it lights up the land and shimmers on the pool. 11 minutes to Middletown grocery stores like Adams Fairacre Farms, restaurants and shopping. 15 minutes to City Winery and it’s new affiliated hospitality project Milk Factory. For the car enthusiast Monticello Motor Club, is just 32 minutes away.
…By Ellis Sotheby's International Realty
120 Ridge Road, Tuxedo Park, New York 10987 Auction | September 16 to 29, 2026 An exceptional opportunity to acquire one of the most remarkable private estates in the New York area. Located in the heart of the prestigious private and secure community of Tuxedo Park in the Hudson Valley, this historic French Provincial-style estate spans over 151 acres of private land, approximately 50 minutes from Manhattan. Built in 1928, this remarkable estate combines historic architecture, absolute privacy and contemporary infrastructure in an exceptional natural environment. The property develops approximately 2,080 m² of built space divided between a majestic main residence, a completely renovated guest house and an independent residence in a former carriage house. Reception areas include a large hall, a large lounge, a reception dining room, a remarkable library, a smoking room, an old chapel as well as a cellar and a wine chest. The exteriors are a true private estate with a boathouse on Lake Tuxedo, a historic log cabin with stone fireplace, a spa and pool house, a tea pavilion, a tennis court, a putting green with bunker, as well as numerous terraces, fountains and ancient sculptures. Two swimming pools complete the facilities: an infinity pool and a separate swimming lane. Bordering nearly 2,000 acres of protected natural areas and crisscrossed by ancient equestrian trails, the estate offers an exceptional level of privacy and tranquility. Exceptional self-sufficient energy infrastructure The estate has benefited from an investment of more than $1 million in its energy infrastructure. It has a system combining solar energy, geothermal energy, private microgrid, industrial-grade generators and high-energy efficiency equipment, allowing the property to operate independently of local public grids. A rare combination of historic architecture and contemporary energy technology. Key features Historic estate built in 1928 Approximately 151 acres / more than 61 hectares Approx. 2,080 m² built Main residence, guest house and carriage house Boathouse on Tuxedo Lake Infinity pool Independent swimming lane Spa and pool house Tennis court Putting green and bunker Tea pavilion Historic log cabin Old chapel Exceptional library Cellar and wine chest Large five-car garage Elevator Solar and geothermal system Private energy microgrid Industrial Generators Private estate in a gated and guarded community About 50 minutes from Manhattan A rare opportunity to acquire a large-scale historic estate in one of the most prestigious private communities in New York State. Contact Immobilier Swiss to receive the complete file and the terms and conditions of participation in the auction.
…By Annonceur International
AUCTION BIDDING OPEN: Bidding ends September 29th. Previously listed at $24.995M. Current high bid $7M. Showings daily by appointment. Contact Concierge Auctions at 646.760.8109 or visit www.conciergeauctions.com for more information. Renamor stands as a rare French Provincial estate built in 1928, when a sophisticated New York couple, Renee and George Amory, commissioned a European-inspired retreat whose art collection would later count the Metropolitan Museum of Art among its admirers. The house was built for original owners George Amory, a major stockholder in the container shipping business Sea-Land Freight Company, and his wife Marion Renee, who inspired the Renamor name. Spanning over 150 private acres within the gated, guarded confines of historic Tuxedo Park, the estate adjoins nearly two thousand acres of protected parkland and old bridle trails, delivering rare privacy just fifty minutes from Manhattan. Three residences totaling over 22,000 square feet include a grand main house with a great hall, banquet dining room, library, wine vault, and former chapel, alongside a fully renovated guest house and a carriage house apartment. A more than one million dollar investment made over a decade ago allows the property to operate entirely off the grid, independent of local utilities, with net-zero energy integration including a microgrid system. A boathouse on Tuxedo Lake, log cabin, spa, tea house, tennis court, and dual pools complete this landmark property, ready for a new era of stewardship.
…By Ellis Sotheby's International Realty
Welcome to this updated and move in ready home in the sought-after Lakeside Community on Greenwood Lake. The community offers with membership access to a private beach, clubhouse and dock space on the lake. There is golfing, skiing and all the Warwick attractions just a short drive away. The property has both raspberry and blueberry bushes as well as newly planted apple and peach trees. Built in 1939 with additions in 1997 & 2013. This home boasts updated electric, plumbing, Pella windows, A high efficiency furnace with new roof, gutters and septic in 2024. Features include views and exceptional winter views of Greenwood Lake, heated floors in bathroom, woodstove insert in the Living Room stone fireplace with cathedral ceilings, vaulted ceilings in Dining Room, there is also a deck and outdoor entertainment area. there are 2 driveways with parking for 8 cars. The main level consists of 2 Br's,, LR, DR, Office, Kitchen, Bath and a 2nd floor sleeping loft. Evaporator coil is installed on furnace for central air. New York City bus at entrance to community This Home won't last, Owner is licensed realtor
…By Prominent Properties Sotheby's International Realty
Overlooking the Hudson River in the esteemed hamlet of Balmville, The Rest is a rare and remarkable offering—a Gothic Revival masterpiece and enduring symbol of 19th-century architecture, masterfully adapted for modern living. The Rest was designed as both a living work of art and an inviting home and celebrates the ethos of High Victorian Gothic Revival showcasing soaring tracery ceilings, gasolier-style chandeliers, floor to ceiling doors adorned with wood-framed diamond-patterned glass, and a Tiffany-style stained-glass window at its heart. Rich inlaid and parquet floors, full-height wood wainscoting, and pocket doors feature prominently in the entry hall, drawing room, library, and dining room. Six original marble and wood fireplace mantels anchor the home. Glass-front-built-ins and intimate mullioned bay window seating invite the sharing of secrets. Befitting its name, The Rest is an approachable home, grounded in comfort with expansive views of the Hudson from a bluestone veranda spanning the western facade. A butler's pantry connects the formal dining room with a chef's kitchen featuring granite counters and river views, warm living room with wide wood plank floors, powder room, and access to the heated pool. The second floor offers a primary suite with views of the Hudson and a custom dressing corridor. The spa-like ensuite has a double vanity, quartz counters, bidet, and soaking tub with river views. The second floor is complete with four additional bedrooms and a bonus room, two with river views, and two more full baths. The upper floors are connected by a discreet secondary staircase and anchored by a traditional oculus or 'roof lantern' that beautifully filters daylight down to the floors below. Commissioned in the 1860s by Daniel Bennett St. John— Congressman, Senator, and a founding editor of The New York Times—this estate was brought to life by Frederick Clarke Withers, a leading figure in American Gothic Revival architecture and influenced by Calvert Vaux, co-designer of Central Park.
…By Julia B. Fee Sotheby's International Realty
More than just a home, this private sanctuary offers a lifestyle of luxury, comfort, and seamless access to all the beauty the Hudson Valley has to offer. Nestled at the end of a quiet cul-de-sac and bordering the southern edge of Harriman State Park, this expansive 5-bedroom, 4-bathroom colonial boasts over 4,400 sq ft of resort-style living, plus a massive unfinished basement with roughly 2,000 sf of endless potential. The backyard is truly exceptional—designed for both serene relaxation and unforgettable entertaining, all with total privacy. At its heart is a heated gunite pool with brand-new PebbleTec plaster and a natural stone waterfall. Lush landscaping with mature plantings surrounds a 2,500 sq ft stone patio, enhanced by landscape lighting, outdoor speakers, and a 21-zone Hunter Hydrawise sprinkler system. The stand-alone Sundance Optima spa offers year-round enjoyment, while a fully equipped pool house includes a full bathroom, changing room, kitchen with beverage fridge and ice maker, and laundry hookups. A built-in outdoor gourmet kitchen transforms every gathering, featuring a custom brick pizza oven, 48" DCS grill, 12" side burner, and 27" warming drawer—perfect for hosting in style. Inside, the home is equally impressive. A dramatic two-story foyer with 18' ceilings sets the tone, flowing into an open and sunlit floor plan with 9' ceilings and oversized Andersen windows with transoms. The newly renovated kitchen and bathrooms feature a curated mix of high-end materials and fixtures. Main-level spaces include a formal living and dining room, a spacious family room with vaulted ceilings and a wood-burning fireplace, a private den with a three-sided fireplace, a home office with French doors and plumbing for a wet bar, and a secondary first-floor ensuite—ideal for multi-generational living. The chef's kitchen looks straight out of a design magazine, showcasing seamless quartzite countertops and backsplash, Viking professional appliances, Sub-Zero 30" refrigerator and 18" freezer, pot filler, built-in microwave and convection oven, and a 94-bottle Perlick Pro Series wine fridge. A massive center island anchors the space—perfect for daily living or entertaining. Upstairs, you'll find four generously sized bedrooms and two full baths, including a luxurious primary suite with multiple walk-in closets and a spa-like ensuite bath complete with radiant heated floors, dual vanities, a deep soaking tub, and a walk-in shower. Additional features include central air, central vacuum, a whole-house Generac generator, Pelican carbon series water purification system, WAVE humidity control and ventilation, full security system with outdoor cameras, and a 3-car garage. The large unfinished basement presents endless possibilities for a gym, theater, or additional living space. All just 45 minutes from NYC and minutes to the Palisades Parkway, golf, marinas, and the hiking trails of Harriman State Park and Bear Mountain.
…By Julia B. Fee Sotheby's International Realty
Winter Hill, a flagship property in the Hudson Highlands, stands at the intersection of preservation, nature conservation and modern design. This timeless Tudor Revival in the heart of Garrison is a one-of-a-kind home, perched atop twenty acres of verdant, natural beauty. As you enter the property and approach the house on the long, winding drive, open fields flanked by stately trees stretch out to your left. When the house comes into view along the ridge, you begin to enter a different state of mind. Blood pressure drops, worries fade, and you are home. This is the home you have always wanted. A home where you can welcome family and friends. Built in 1883 for Rev. Walter Thompson and restored and modernized for use as an office over the past decade by a team of skilled architects, designers and craftsmen, Winter Hill emerges in full view as you crest the ridge. Park in either the sprawling forty space lot, perfect for entertaining many guests, or under the porte-cochere, connected to the wrap-around porch. Open the double doors and enter the main foyer, with a unique wall design, and find yourself in an elegant living room, centered on a huge wood-burning fireplace. Original details - pocket doors, gleaming hardwood floors and walls of multi-paned windows - are accentuated by the modern glass chandelier. Beyond is the front parlor, with striking bay window seating. Behind, you will find the massive central dining room, with amazing original fireplace details, then a perfect home office space or potential formal library, with its own fireplace. All of these rooms flow together to make an amazing space for entertaining. Imagine friends, family and community gathering here, in your home. Off the central hall, find the chef's dream kitchen, with beautifully unique light fixtures, stainless appliances, two ovens, a prep sink and abundant counter space. More on this level: a back room that would be a great first floor bedroom, two half baths and a bonus room. Everywhere are open or wooded views. Step out to the covered front porch and slate patio. Here, you'll host drinks in the evening, or simply sit with a cup of tea in the morning, looking over the serene fields. On the second level, arrived at via the convenient, full four-floor elevator, or gorgeous front staircase, opportunity abounds. Currently used as offices, the many large and bright rooms here can be converted into guest bedrooms, family rooms, playrooms and more. Two of the rooms have fireplaces. Other 1800's details, like wood floors and leaded glass windows, are here, as elsewhere. Most rooms have views to the gorgeous grounds. One floor up, find even more bright spaces - bedrooms, guest areas, artist and craft rooms, or wherever your vision takes you. Let’s hop in the elevator and jet down to the lowest level, to discover large spaces that are perfect for home gyms and media rooms. There are huge storage rooms and the new utility systems, including state of the art electrical and a/v rooms. Leaving the basement through the walkout, we exit to the side yard and look out to the fields flowing before us. At the side is the private guest cottage above the two-car garage. This cottage has views of its own, a kitchen and full bathroom. This is a perfect spot for your guests, or extended family. Nearby, the large water tower ensures never running out of fresh water. From here, we can see the property at a different angle. The home’s cedar shingle siding and roof, with stately brick chimneys, rises before us. To our right, protected land, to our left the park-like land and rolling hills stretching out to the tree line, almost as far as you can see. All of this, just minutes to the train and the heart of Cold Spring. Come, visit Winter Hill and join its living story.
…By North Country Sotheby's International Realty
Set in the heart of Beacon's historic Main Street district, 469 Main Street is a rare 1876 mixed use building reimagined for modern life without ever losing its soul. Fully renovated and lovingly maintained by its current owners, an artists couple, this landmark property offers a flexible live/work configuration that can flow as a single residence above thriving commercial space, or be reconfigured into one, two, or three distinct storefronts to suit an owner's vision. Here, exposure and privacy coexist in perfect balance, with the energy of Main Street foot traffic just steps from the calm of a private patio or rooftop deck retreat, making this an exceptional opportunity for a creative entrepreneur, an owner occupant, or an investor seeking to diversify income streams in one of the Hudson Valley's most sought after towns. Character defines every room. Exposed brick, reclaimed hard pine flooring finished in oil, original cast iron and wood brackets, bluestone counters and thresholds, and a granite hitching post reborn as a bench all speak to the building's nineteenth century roots, while high ceilings, oversized windows, ornamental grates, recessed lighting, and farmhouse style pendants bring a refined, livable warmth throughout. The result is an organic flow from one space to the next, elegant yet unpretentious, polished yet full of soul. The commercial level presents two storefronts full of charm and original detail, a back office with classic Dutch doors, and an ADA accessible bathroom, complemented by the Annex, a versatile addition with accordion doors, polished concrete floors, its own bathroom, and a prep kitchen with cabinetry and a mini fridge, ideal for retail, gallery, studio, or hospitality use. Above, the residence unfolds across three thoughtfully designed levels. The ground floor connects an airy, light filled kitchen to the living room and a private back patio with a majestic Sycamore Maple tree, with a striking black spiral staircase rising to the second floor in addition to the front stairway. There, two bedrooms with generous built in cabinetry sit near a reading nook framed by wide windows and pleated Japanese shades, while a bathroom finished in original reclaimed walls and slate tile leads into a grand studio space, currently used as a painter studio, with the possibility of restoring additional windows for even more light. The third floor offers a rooftop studio suited to quiet retreat, opening onto a cedar wood rooftop deck with sweeping views of the city and Mount Beacon beyond. Every system has been considered with the same care as the finishes. The property offers ADA access across all commercial spaces, three electric meters and one water meter, natural gas furnace heating and central air on the first floor, and mini split heating and cooling for the second floor, third floor, and Annex. Additional infrastructure includes a full sprinkler system, hardwired smoke and carbon monoxide detection, fire suppression, and a steel fire door separating the domestic and commercial areas. Outdoors, a solar operated gate opens to a private parking area that doubles easily as a terrace or event space, alongside charming, private back and rooftop patios. A back gate provides access to municipal parking, and a gated private driveway offers additional parking enhanced with planters and benches. Below, a waterproofed basement currently serves as storage and a photography darkroom. A true landmark reborn, 469 Main Street offers an unmatched blend of historic character, livable elegance, and commercial opportunity in the center of Beacon, New York, moments from the region's celebrated art community, galleries, restaurants, and everything this vibrant Hudson Valley city has to offer.
…By Four Seasons Sotheby's International Realty
A rare opportunity to own over 5.9 acres across three separate parcels in the heart of Garrison. The main residence at 111 Philipse Brook Road is a 4-bedroom, 2.5-bath Colonial built in 1987, offering approximately 2,294 square feet of living space on 1.83 acres. The home features a gracious layout with spacious living and dining areas, wood-beamed ceilings, two fireplaces, a finished lower-level recreation room, open and screened porches, and an attached two-car garage. Included in this offering are two additional separately deeded parcels: 2.25-acre lot 1.83-acre lot All three parcels together provide flexibility for estate expansion, compound living, long-term investment, or preservation of privacy. The combined acreage offers a rare opportunity to control surrounding land in this highly desirable Garrison location. Located within the Garrison School District and just minutes to Metro-North, hiking trails, the Hudson River, and the cultural attractions of Cold Spring and Beacon. A unique offering with exceptional potential — available as a package with all three parcels included in the sale.
…By Julia B. Fee 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.