Courtesy: Blooming Realty
845-388-1900
220 Oxford Road is a Truly Impressive Property! Offering over 3,500 sq ft of beautifully maintained living space, this home features 3 bedrooms plus an additional upper-level room, 3 full baths, and 1 half bath. Spacious living room, stunning family room, and a practical, well-designed kitchen. The home showcases elegant finishes throughout along with brand new flooring that adds a fresh modern touch. Full basement provides excellent storage space. Additional features include Central AC, original Andersen custom windows, and an attached 2-car garage. Step outside to a massive deck, spacious shed, and gorgeous landscaping set on a nice-sized lot. Conveniently located close to all amenities, this property offers privacy, space, and everything you could want in a home and more!
Courtesy: Platinum Realty Associates
845-354-3246
A Private Suburban Retreat on Prestigious Garnet Hill. This Center Hall Colonial offers an exceptional residence- refined suburban living with the space, privacy, and sophistication sought by discerning buyers—just about an hour from Manhattan. Positioned on a beautifully landscaped 3+ acre property, the home features approximately over 4,700 square feet of elegant living space, offering 5 bedrooms and 3.5 full baths. Luxury begins at the illuminated pillars lining the paver driveway, leading to a stone-accented front entry. Inside, sun-filled interiors highlight quality craftsmanship throughout. The two-story foyer features tray ceilings and expansive windows, while recessed lighting, built-in surround sound, and pre-wiring for a security system add comfort and functionality. The chef’s kitchen is a true centerpiece, featuring floor-to-ceiling custom cabinetry, granite countertops, a large center island with seating, and a premium Sub-Zero stainless-steel refrigerator. Adjacent casual dinette provides effortless flow for hosting, with sliding doors opening to the outdoor living areas which provide direct access to a deck & patio area. The oversized family room becomes the center of the home surrounded by windows and comforted by the fireplace. Upstairs, the primary suite offers a private retreat with two custom walk-in closets, a sitting area, and alcove. The en-suite bath features dual vanities, a walk-in shower with multiple shower heads, and a jetted soaking tub overlooking serene sunset views. Three additional bedrooms and one full bathroom are generously sized and thoughtfully arranged on the same level. Outdoors, the property delivers a resort-style experience, expansive open grounds framed by mature landscaping and stunning sunset views. The setting offers exceptional privacy and room to relax, entertain, or expand. Additional highlights include a three-car garage and a setting that perfectly balances tranquility with accessibility. This is a rare opportunity to enjoy luxury suburban living—where space, serenity, and elegance meet effortless access to New York City.
Courtesy: MK Realty Inc
845-782-0205
Welcome to 208 Glenmere Rd, Chester, NY! This charming country home, nestled on picturesque grounds, is now available for sale. The main level features an eat-in kitchen, a formal dining room, and two spacious bedrooms, while the upper level offers three additional bedrooms. The newly renovated cottage boasts new flooring, windows, kitchen, and heating system. The interior has been freshly painted, and all appliances and flooring are almost new. With 1,815 square feet of living space set on a one-acre lot, there's ample room to relax and enjoy the tranquility of this lightly traveled roadway. To elevate your property, you get this extraordinary two-story garage, a rare find that perfectly blends functionality and versatility. Fully powered with electricity, this space becomes more than just storage—it transforms into the ultimate workshop, creative studio, or home office, tailored to your passions and needs. The thoughtfully designed upper level invites endless possibilities, whether you seek a private retreat, an inspiring workspace, or a recreational haven. Bright, spacious, and easily accessible, this well-constructed garage is a game-changer, adding both convenience and significant value to your home. Call today to schedule your showing!
Courtesy: Keller Williams Realty
845-928-8000
Own a true piece of history with the iconic Hambletonian House, a one-of-a-kind Victorian estate built in the 19th century by William Rysdyk, original owner of Hambletonian 10—the legendary sire that shaped nearly all modern Standardbred racehorses. Perfectly positioned on nearly three private acres atop a knoll in the heart of Chester, New York, this meticulously maintained property offers a rare blend of historic grandeur, modern comfort, and income-producing potential. The main residence features seven bedrooms and four and a half baths, showcasing timeless Victorian craftsmanship throughout, including soaring ceilings, original hardwood floors, intricate moldings, marble fireplaces, pocket doors, and elegant architectural details that have been carefully preserved. Expansive living and entertaining spaces flow seamlessly into outdoor areas, ideal for gatherings, events, or quiet enjoyment of the serene setting. Enhancing the property’s versatility is a second detached building featuring a well-appointed two-bedroom apartment, ideal for guest accommodations, rental income, or on-site management. A separate pool house with a full bathroom and sauna introduces a resort-style element, creating a private retreat perfect for relaxation, wellness, or entertaining. The current owner has taken exceptional care in maintaining and improving the property, including significant updates to major mechanical systems and the roof, ensuring both historic integrity and modern reliability. This thoughtful stewardship allows the next owner to enjoy the property with confidence while preserving its legacy. With strong potential as a hospitality property, the estate presents flexible opportunities for use as a bed and breakfast, short-term rental, private residence, or boutique event venue. Its rich provenance, combined with strong visual appeal and a unique story, creates a standout offering that cannot be easily replicated in today’s market. Situated in close proximity to local amenities, transportation, and the charm of the surrounding area—and just 45 miles from Manhattan—the property offers both privacy and accessibility. Whether you are seeking a distinctive primary residence, a lifestyle investment, or a legacy property with unmatched historical significance, the Hambletonian House represents a truly rare opportunity.
Courtesy: MK Realty Inc
845-782-0205
Welcome to 4 Greycourt Road, your dream home awaits! This delightful residence boasts a spacious 6-room layout, featuring 3 generous bedrooms and 1.5 baths, all nestled on over 2.5 acres of stunning greenery. Imagine whipping up culinary masterpieces in the well-appointed kitchen, complete with ample cabinetry and modern appliances—perfect for any cooking enthusiast! Each bedroom is a serene retreat, filled with natural light from large windows that create a warm and inviting atmosphere. But the real gem lies outside—step onto the expansive deck, ideal for outdoor living and entertaining. Picture sunny afternoons by the sparkling inground pool, marking memories forever. Additional features include self-maintained Generac generator, new natural gas boiler installed in 2021, an updated well and water softener. Don’t miss your chance to own this captivating home! Call today to schedule your private showing and take the first step toward your new lifestyle!
Courtesy: Artisan Realty
845-721-2058
New beginnings offered in this light and bright fully refreshed end unit in the highly sought after Whispering Hills community. Featuring new designer paint throughout, brand new luxury vinyl plank (LVP) flooring, new stainless steel appliances, two car garage with recently installed garage doors and so much more. Located close to major highway, NYC bus and shopping. Club house with gym, basketball and tennis courts, playgrounds and 2 inground pools. Low taxes! Town and County, $1,110.66, Village $1,207.63, School $3,184.65. **Interior photos coming soon
Courtesy: Howard Hanna Rand Realty
845-928-9691
Brand new to the market! This spectacular spacious colonial has room for everyone! Perched at the top of the Fieldcrest subdivision with sweeping views that can’t be missed you will find this property that offers something for everyone. Set on 1.3 picturesque acres in a desirable neighborhood, this beautifully maintained home offers the perfect blend of comfort, space, and functionality. Enjoy sweeping views and breathtaking sunsets from the expansive front porch overlooking the oversized front yard. The property is designed for both relaxation and entertaining, featuring a fenced backyard with a new oversized Trex deck with a 20-year guarantee, an above-ground oval swimming pool with a new filter (2025), elevated garden/play area, storage shed, and a newer paved driveway leading to the attached two-car garage. Inside, the home showcases gleaming wood floors and recessed lighting throughout the main level. The oversized dining room is filled with natural light from a triple bay window and accented with elegant chair rail molding. A spacious living room with a stunning stone fireplace creates a warm and inviting atmosphere, while the expansive family room offers endless possibilities for entertaining and everyday living, complete with a pellet stove capable of heating the whole house and French doors connecting to the living room. The kitchen is thoughtfully designed with granite countertops, abundant cabinetry, pantry storage, stainless steel appliances all under five years old, double ovens, tiled flooring, recessed lighting, and direct access to the backyard deck. Upstairs, you’ll find three generously sized bedrooms plus a bonus room ideal for a home office or flex space. All bedrooms offer ample closet space and abundant natural light. The main hall bath features a double vanity, while the spacious primary suite includes an en-suite bath with a shower and relaxing Jacuzzi soaking tub. Convenient second-floor laundry adds to the home’s practicality. A walk-up attic provides exceptional storage space, while the full basement offers even more room for storage or future possibilities. Additional updates include central air with a 4-ton condenser unit just four years young, a boiler and water heater both approximately six years old, and appliances all under five years old.
Courtesy: Keller Williams Realty
845-928-8000
What a remarkable property in the town of Chester, NY-a highly sought after town in the southern Hudson Valley, only 45 minutes from the GW Bridge! This 3 bedroom, 2 bathroom house boasts tons of modern and energy efficient features. A massive renovation done only 5 years ago leaves you with nothing to maintain except to pick your paint colors and finishes. 1st floor main bedroom and additional room that could be an office, guest space or play room. This house has a ton of new systems in the house-all being done about 5 years ago or less, new roof, new complete septic system, regraded back yard, Bilko doors, all new plumbing, newly renovated bathrooms, refinished kitchen, new flooring on the 1st floor and 2nd, new windows in most of the house, new water heater, UV Light system, well pump pressure tank, oil tank (not currently used, but still plumbed), Solar array, mini split heating/cooling system, driveway, sump pump, stainless steel appliances-it's basically a new house! Just minutes from the NYS Thruway, Legoland, Woodbury Commons Premium Outlets, West Point, shopping and public transportation.
Courtesy: R2M Realty Inc.
845-358-2001
Lovely, Light and Airy 2 Bedroom 1 and 1/2 Bath Unit in Desireable Whispering Hills! Updated Kitchen and Bath, New Carpet and Freshly Painted. Downstairs has a Comfy Living Room with a Wood Burning Fireplace , Sunny Dining Room with Slider to a Patio, Convenient Galley Kitchen, Laundry Area and 1/2 Bath. Upstairs are a Spacious Primary Bedroom , Walkthrough Closet to Full Bath and a Roomy Second Bedroom. W/H only 2 years old and HVAC only 6 years old. The Community boasts 2 Inground Pools, 2 Clubhouses, Basketball Court, 2 Playgrounds, Fitness Center, Dog Walk, and Tennis Courts. Conveniently Located to Public Transportation and Shopping. All Ready for it's New Owner to Move right In!
Courtesy: Keller Williams Realty
845-928-8000
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.
Courtesy: Cronin & Company Real Estate
845-744-6275
Set at the end of a quiet executive cul-de-sac, this refined modern colonial offers a rare blend of quality, scale, and effortless livability on over two acres of level, park-like grounds framed by mature trees. Designed for both everyday comfort and elevated entertaining, the home unfolds with a sense of openness and intention, where natural light and thoughtful craftsmanship define every space. A dramatic two-story great room serves as the centerpiece, where expansive windows draw the outdoors in and a gas fireplace anchors the space with warmth and sophistication. The seamless flow into the chef’s kitchen creates a natural gathering point, featuring a substantial center island, GE Profile stainless steel appliance suite, custom wine bar, and a sunlit dining area perfectly positioned to overlook the serene backyard. The main level is as functional as it is elegant, offering gleaming hardwood floors, a private home office, mudroom, and a first-floor bedroom that is complemented by the first floor full bath, ideal for guests or multi generational living. Upstairs, four additional bedrooms provide generous accommodations, including a well-appointed primary suite with dual walk-in closets and a spa-inspired bath complete with a glass-enclosed shower and soaking tub designed for quiet retreat. Outdoor living is elevated to a new standard with a custom paver patio centered around a roaring gas fire feature, creating an inviting atmosphere for evening gatherings under the stars. A composite deck extends from the home, offering a peaceful vantage point over the expansive backyard, while the wraparound front porch delivers timeless curb appeal and a place to unwind. Additional highlights include central air conditioning, a three-car garage, impressive well maintained mechanicals, and a full walkout basement with high ceiling height, offering endless potential for future customization. Perfectly positioned within the highly sought after Monroe-Woodbury School District and just minutes to Route 17, the NYS Thruway, and Woodbury Commons, this property offers both convenience and seclusion in equal measure. A home of this caliber is meant to be experienced. Schedule your private tour and discover the lifestyle that awaits.
Courtesy: Weichert Realtors
845-782-4646
Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home features 4 spacious bedrooms and 3 full bathrooms, creating an inviting layout ideal for everyday living and entertaining. Step inside to a grand, sun-filled foyer with soaring ceilings that set the tone for the home’s warm and elegant feel. The thoughtfully designed kitchen is perfect for cooking, gathering, and hosting. Outdoors, enjoy your own private retreat with an above-ground pool, play area, and a beautiful, wooded setting. With over 18 acres, the land offers exceptional privacy, natural beauty, and a peaceful buffer around the home. A rare opportunity to own a spacious Colonial with room to live, relax, and entertain—inside and out. Schedule your private showing today!
Courtesy: RE/MAX Benchmark Realty Group
845-565-0004
Welcome to 35 Maple Avenue, a bright 3 bedroom, 3 full bath Raised Ranch in the desirable Village of Chester ideally located near the Village Park & School. This spacious 2,032 sq. ft. residence built in 2002 & Updated in 2020 including bathrooms & New Kitchen in 2024. The open main level features a White EIK with Quartz Counters & Island, stylish white tile backsplash, Pantry, Black Appliances, Recessed lighting & durable Vinyl plank floors -low maintenance & stylish for a busy lifestyle. Enjoy everyday living & entertaining with a formal dining room that opens to a sliding door to the back deck with a view. Sunny Living room with Bay window, cozy gas fireplace with a striking surround tile & vinyl plank floors perfect for relaxing evenings at home. . Down the hallway to a Primary suite with Full Private Primary bath, 2 additional bedrooms & second Full bath serves the remaining bedrooms. The finished lower level offers flexibility with a private full bath and family room with vinyl flooring and an additional room for an office, guest room or playroom. Laundry room. Practical conveniences include a spacious 2 car garage with Mechanicals and storage. Blacktop driveway with room for 4 cars. Public Water & Sewer is included in the taxes. In 2020 a new gas heating system was installed and updated Air conditioning in 2018. Set on .26 acre landscaped lot with road frontage in a quiet residential neighborhood. A generous back yard with a view of the Village Park. This home offers the perfect balance of comfort and convenient living in a sought-after village location. This is an excellent home for buyers seeking convenience, updates and flexible living. Includes a Shed. Solar Panels are leased. Close to major highways and shopping.
Courtesy: MK Realty Inc
845-782-0205
Discover your new haven at this charming 3-bedroom, 2.5-bathroom condo nestled in the vibrant community of Chester, NY. Perfect for those looking to infuse a home with their personal style, this residence offers fantastic potential to make it your own. Let your imagination take the reins and make this spacious house into your dream home! The condo is thoughtfully designed with ample room for rest and rejuvenation. The primary bedroom serves as a peaceful retreat after a busy day. The additional bedrooms provide comfortable living space for family or guests, while the numerous bathrooms ensure morning routines are seamless. Step outside and you'll find yourself in a delightful outdoor area, ideal for weekend gatherings or a quiet morning coffee. The community is just as inviting, with plenty of amenities including a pool and clubhouse. Convenient shopping is just a stone's throw away at the ShopRite of Chester Plaza, making your daily errands a breeze. For those who cherish leisure and entertainment, the Jarvis Boone Memorial Amphitheater offers a cultural escape where various performances can be enjoyed under the stars. Located in a town rich with attractions and community warmth, this condo isn't just a place to live, but a place to love. Embrace the opportunity to create your perfect home in a location that's both convenient and captivating. Whether you're enjoying the local amenities or relaxing in your potential-filled condo, life here promises to be anything but ordinary. Come see why this property could be the cornerstone of your new lifestyle. The apartment is currently tenant occupied.
Courtesy: Serhant LLC
646-480-7665
Set behind a gated entrance with a private guard house and unfolding across 8.4 private acres, The Retreat at Greentree is a true estate in every sense, engineered for privacy, designed for lifestyle, and positioned as one of the most unique offerings in the Hudson Valley. A cascading waterfall greets you on arrival, establishing a sense of calm and separation from the outside world. From that moment forward, every detail reinforces the same idea. This property was built intentionally, without compromise. Originally designed by renowned architect Paul Rudolph, the residence carries a level of architectural pedigree rarely available. Spanning over 7,750 square feet, the home blends that design legacy with modern performance, including radiant heated floors, geothermal systems, and thoughtfully curated living spaces that feel both refined and highly functional. What truly sets this property apart is the lifestyle it delivers. A private helipad offers direct access to Manhattan in approximately 14 minutes, redefining convenience at the highest level. The grounds unfold as a resort-caliber setting, anchored by a heated saltwater pool, three private cabanas, and a fully equipped outdoor kitchen with a dedicated dining space designed for effortless indoor outdoor living. A rare white sand beach introduces an unexpected element, creating a setting that feels more like a destination resort than a private residence. Inside, the home takes on a spa-like atmosphere, with wellness-driven features including a private sauna and spaces designed to restore and recharge. The primary suite is its own retreat, complete with a three-season room that extends the experience outdoors while maintaining complete privacy. A fully built-out home theater adds another layer to the lifestyle, bringing a true cinematic environment into the comfort of your own home. Beyond the property itself, the location adds another dimension. This is the perfect getaway for winter weekends, fall retreats, or summer escapes, surrounded by some of the Hudson Valley’s most sought-after destinations. Just minutes from LEGOLAND New York Resort, Woodbury Common Premium Outlets, Warwick Valley Winery & Distillery, local apple orchards throughout Warwick, Bear Mountain State Park for skiing and outdoor recreation, and the five-star Glenmere Mansion, the area offers a rare blend of recreation, luxury, and accessibility. Hiking, camping, fishing, skiing, biking, horseback riding, fine dining, and shopping are all within reach, creating a year-round lifestyle that is both active and refined. This is more than a residence. It is a fully realized compound, private, efficient, and architecturally significant, built for someone who values time, discretion, and a level of living that cannot be replicated.
Courtesy: Keller Williams Realty
845-928-8000
Welcome to the highly sought-after Creamery Estate! This inviting waterfront Colonial-style home offers the perfect blend of comfort, charm, and scenic beauty, set on an acre of beautifully maintained grounds with peaceful views of Creamery Pond. This 3-bedroom, 3 full bath home features hardwood floors throughout and a spacious, easy-flow layout designed for everyday living. The updated kitchen, complete with brand new LG appliances, butcher block countertops, and a stylish tiled backsplash, opens into a formal dining room—perfect for hosting friends. Enjoy multiple living spaces, including a sun-filled living room and a cozy family room with a fireplace, creating a warm and welcoming atmosphere. A dedicated home office offers the flexibility you need for remote work or a quiet study space. Upstairs, the primary suite is a true retreat, featuring a private full bath with double vanities, a whirlpool tub, and a private balcony overlooking Creamery Pond—the perfect place to start or end your day. Two additional generously sized bedrooms and a full hall bath complete the upper level. The finished basement (not included in square footage) provides even more room to spread out, offering ideal space for a playroom, home gym, or guest area, along with walkout access and egress windows for added convenience. Step outside to your expansive deck and enjoy your private, fenced-in waterfront backyard—perfect for summer barbecues, morning coffee, or simply taking in the peaceful surroundings. Spend your days fishing, kayaking, or relaxing by the water from your own private dock. Conveniently located near schools, the Village of Sugar Loaf, boutique shops, and dining, and just about an hour to NYC. Enjoy easy access to local orchards, wineries, ski areas, the Appalachian Trail, and the Heritage Bike Trail—making this home ideal for both relaxation and year-round recreation. A rare opportunity to own a true waterfront gem!
Courtesy: eXp Realty
888-276-0630
Tucked away on over 3 private acres, this recently renovated custom residence offers a rare blend of seclusion, craftsmanship, and elevated living. Surrounded by hundreds of acres of protected state land, the setting ensures unmatched privacy with direct access to nature, including trails that connect to the Appalachian Trail just beyond your backyard. A natural waterfall adds to the serene landscape, creating a truly one-of-a-kind backdrop. A dramatic entry introduces the home with soaring ceilings and heated marble floors, setting the tone for the refined interiors throughout. The layout flows effortlessly into expansive formal living and dining spaces, ideal for both everyday living and entertaining. At the heart of the home is a thoughtfully designed chef’s kitchen featuring premium appliances, custom stone and tile finishes, a gas range with griddle, double ovens, and an oversized two-tier island with prep sink. A walk-in pantry and elegant butler’s area provide both function and style. The family room is a standout space, offering scale, natural light, and architectural character, making it the perfect gathering area. Designed with entertaining in mind, the outdoor living experience is just as impressive, complete with a full stone kitchen and bar, a spacious stamped concrete patio, and a private hot tub retreat, all surrounded by custom masonry. Upstairs, the primary suite serves as a private sanctuary with its own balcony and spa-inspired bath featuring a soaking tub, custom shower setup with steam capability, and refined finishes throughout. Additional bedrooms are generously sized, offering comfort and flexibility for guests or extended living. The fully finished lower level expands the living space with a recreational area, full gym, and wet bar, perfect for hosting or unwinding. Throughout the home, hardwood flooring, an integrated sound system, and high-efficiency construction with spray foam insulation and multiple heating zones enhance both comfort and performance. Completing the property is a spacious three-car garage, a beautifully maintained yard with room to enjoy, and infrastructure already in place for a future gated entrance. A truly exceptional offering where design, privacy, and lifestyle come together seamlessly.
Courtesy: eXp Realty
888-276-0630
Beautiful Colonial set on just under an acre of meticulously landscaped property, offering breathtaking sunset views from a very private backyard. Great spacious front porch! On a quiet cul-de-sac, this home features a stunning in-ground pool with a new heater, cover & pump. Pool filter, and liner are about 4 years young. The pools heating system runs on propane tank. Entire home was freshly painted just 3 years ago! Behind the house are expansive woods and protected wetlands that cannot be developed, offering exceptional natural privacy! The main level features 9 ft ceilings, a lavatory, a bright dining room, family and living rooms with a fireplace, and an eat-in kitchen with granite countertops, stainless steel appliances, and a center island. Upstairs includes 4 spacious bedrooms, including a primary suite with its own bathroom w/ a jacuzzi tub and separate shower, plus an additional full bathroom in the hallway. The home is thoughtfully updated with major improvements throughout, Including a central AC system upgraded just 2 years ago, along with a regularly maintained boiler with upgraded piping. Additional upgrades include a new driveway & new garage doors. Inside, you’ll find hardwood floors throughout the house and new sliding glass doors that open to a spacious deck. The front porch and back deck have both been freshly re-stained, enhancing the home’s curb appeal. The washer and dryer are included; the washer is approximately 4 years old, while the refrigerator, dishwasher, and oven are about 5 years old. The unfinished, waterproofed basement offers excellent potential for additional living space or storage. The basement foundation walls have been drylocked, and the basement is essentially waterproof.
Courtesy: Keller Williams Realty
845-928-8000
Set gracefully on 3.8 private acres within the highly coveted Warwick School District, this exceptional custom home offers a rare blend of architectural elegance and refined living. Surrounded by a collection of equally distinguished residences, the property provides an expansive, park-like sanctuary while remaining nestled in the heart of one of the region’s most sought-after communities. Spanning over 4,500 square feet of meticulously finished living space, with more than 6,800 total square feet including an expansive unfinished lower level, the residence showcases thoughtful design and elevated craftsmanship at every turn. A dramatic double-height great room anchored by a striking gas fireplace creates a grand yet inviting focal point, while graceful arched openings and upgraded black windows lend a timeless, sophisticated aesthetic. The main-level primary suite is thoughtfully positioned as a private retreat, complete with a spa-inspired bath and exclusive access to a deck overlooking the serene, park-like grounds. Designed with both everyday living and entertaining in mind, the home features a well-appointed butler’s pantry, media room, elegant lounge areas, a dedicated office nook, and an upper-level catwalk and loft that further enhance its architectural character. The unfinished lower level presents a blank canvas for customization—ideal for a private fitness studio, wine cellar, or full-scale entertainment space. Outdoors, a classic rocking-chair front porch welcomes you, while the surrounding acreage offers exceptional privacy without sacrificing accessibility. Natural gas availability adds both convenience and long-term value. Perfectly situated for commuters, the property is moments from major roadways and within walking distance to Tin Barn Brewing, while also enjoying close proximity to Warwick’s renowned wineries, farm markets, and dining destinations.
Courtesy: Q Home Sales
845-357-4663
Welcome to Blooming Grove NY (Chester) Monroe/Woodbury Schools! Wow! This home has a vibe! Custom built 4 bedroom colonial with a front porch, sitting on 3.2 acres fully fenced green property to protect all the flowers, foliage and specimen plantings. This home features spacious rooms throughout, hardwood floors on the main level, Eat in kitchen with open feel to the family room with a warm fireplace, music room/library with custom built bookcases, 4 large bedrooms with ample closet space, large windows overlooking a stunning property, BONUS room! fabulous screened in room with pine floors, special Japanese wood, cathedral ceilings, operable screens and retractable shades, a composite deck with self watering planters, full ready to be finished basement with sliders to the yard, plus a huge custom shed attached to the home which has room for lawn equipment and outdoor furniture storage. This home has Tesla solar panels on the roof, (Only about $50 per month for electric) a large driveway, a gorgeous cul-de-sac, and more!
Courtesy: Ellis Sotheby's Intl Realty
845-353-4250
The Conklin House: A Masterpiece of History & Modern Luxury. Experience the perfect blend of early 20th-century charm and 21st-century comfort. The Conklin House, 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.
Courtesy: Keller Williams Realty
845-928-8000
Experience Elevated Living: Your Private Hudson Valley Retreat at 1311 Whispering Hills Welcome to a home that offers more than just square footage—it offers a lifestyle change. Nestled in the scenic rolling hills of Orange County, 1311 Whispering Hills is a masterclass in modern suburban living. This meticulously maintained residence captures the essence of "home" from the moment you step through the door, blending airy, sun-drenched interiors with the tranquility of a park-like setting. The Interior Experience The heart of the home is designed for the modern rhythm of life. The open-concept living area serves as a versatile canvas, whether you’re hosting sophisticated dinner parties or enjoying a quiet Sunday morning with a book. High ceilings and oversized windows create a seamless connection to the outdoors, while the gourmet-inspired kitchen provides the perfect workspace for the home chef. Retreat to a spacious primary suite that acts as a true sanctuary, featuring generous closet space and a layout designed for maximum relaxation. Resort-Style Amenities & Local Charm Life at Whispering Hills feels like a permanent vacation. As a resident, you have exclusive access to: Active Recreation: Two sparkling swimming pools, tennis and basketball courts, and a modern clubhouse. The Great Outdoors: Minutes from the Heritage Trail, a 19-mile linear park perfect for cycling, running, and walking the dog. Convenience Redefined: Located just a stone’s throw from the historic Village of Chester, the Sugar Loaf Arts & Crafts Village, and the world-renowned Woodbury Common Premium Outlets. The Commuter’s Secret While you’ll feel worlds away from the city noise, you are strategically positioned for an effortless commute. With rapid access to Route 17 and I-87, plus nearby bus and train links to Manhattan, this property offers the rare "best of both worlds" scenario.
Courtesy: eXp Realty
888-276-0630
Welcome to Chester, NY, a resort-style luxury colonial set on a private 1.1-acre cul-de-sac lot in the Monroe-Woodbury area of Orange County. This custom residence delivers the space, craftsmanship, and lifestyle today's relocation and move-up buyers are searching for, with approximately 4,624 square feet, refined architectural detail, mountain views, and seamless indoor-outdoor living. From the bluestone entry and custom foyer to the arched windows, detailed millwork, and stone fireplace, every major room has been designed to make a statement. The chef's granite kitchen, expansive family room, and finished lower level with theater, gym, and additional recreation space create flexibility for entertaining, working from home, and everyday luxury. Outside, the backyard becomes the headline feature: saltwater in-ground pool, firepit, koi pond, extensive pavers, and a 3-season outdoor kitchen that gives this home true vacation-at-home appeal. For buyers looking for a luxury home in Chester NY, a Hudson Valley estate near NYC, or a Monroe-Woodbury area home with pool, privacy, and commuter convenience, This is the kind of property that sells both a residence and a lifestyle.
Courtesy: Keller Williams Realty
845-928-8000
This beautiful custom home is planned to be built in the highly sought-after Sugar Loaf area, offering the convenience of municipal water and sewer. The main level welcomes you with warm hardwood floors and a kitchen featuring a choice of elegant granite or quartz countertops, a stainless steel appliance package, a center island perfect for meal preparation, and a spacious dining area with a slider that opens to a spacious deck. The cozy family room, complete with a fireplace, creates an ideal spot for gatherings. Also on this level are three comfortable bedrooms, including a primary suite with a bathroom showcasing a double vanity, a relaxing soaking tub, and a tiled shower, along with a stylish main hall bath. The finished lower level offers additional space with an extra bedroom or home office, along with a large recreation or living room—perfect for relaxing or entertaining. Enjoy extra features and the chance to choose custom finishes that make your home uniquely yours. Located conveniently near shopping, charming boutique stores, restaurants, wineries, breweries, apple orchards, lakes, Appalachian trails, and major commuter routes, with just about an hour to reach NYC.
Courtesy: Keller Williams Realty
845-928-8000
3 bedroom 2 bath contemporary home tucked away on a quiet street. Modern renovation already started, put your finishing touches on it. Home sold as is. Open concept living, spacious kitchen, private primary suite on 2nd floor with 2 additional bedrooms on 1st floor. Peaceful setting and still close to all amenities. 1,000 sq ft 2 car detached garage.
Chester is located in New York. Chester, New York 10918has a population of 12,477. Chester 10918 is more family-centric than the surrounding county with 37.24% of the households containing married families with children. The county average for households married with children is 36.93%.
The median household income in Chester, New York 10918 is $120,288. The median household income for the surrounding county is $85,640 compared to the national median of $69,021. The median age of people living in Chester 10918 is 39.1 years.
The average high temperature in July is 83.4 degrees, with an average low temperature in January of 16.3 degrees. The average rainfall is approximately 47.1 inches per year, with 39.1 inches of snow per year.
