Courtesy: Tuxedo Hudson Realty Corp
845-915-4567
Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with original wooden and stone mantles, 10' ceilings, and large sun-filled windows throughout. The main level offers two gracious living rooms, a formal dining room, a dedicated office, and an updated kitchen outfitted with a Wolf range, cherry cabinetry, generous storage, and a walk-in pantry. A dedicated first-floor laundry room adds convenience. Upstairs are four spacious bedrooms and two full bathrooms, including a generous primary suite with a large walk-in closet and a 5-piece ensuite bath. These spaces reflect the thoughtful renovation completed in 2014 by previous owners, which also included a living room extension, upgraded kitchen, and a 1,250 sq ft three-car garage designed to complement the home’s historic profile. The lower level is just as impressive. The dry, clean basement contains a unique wine-tasting room set against the original hand-stacked stone foundation, offering a charming and unexpected entertaining space. The 5-acre property offers level, usable land framed by mature native trees—including two historic Linden trees dating to the late 1800s—and expansive lawn. In 2022, the owners installed an 8,000 sq ft organic vegetable garden complete with deer fencing and a full irrigation system, creating a highly productive and beautiful outdoor space. Additional improvements include new trees and screening, newly added parking, a ground-floor repaint, refinished wood floors, an EV charger (CCS), and the conversion of the former stable into a functional workshop. Three outbuildings expand the estate’s potential for creative, professional, or commercial work. The 3,036 sq ft workshop is fully equipped with 6" concrete floors for heavy machinery, 220V power, propane heat, ventilation systems, a bathroom with independent septic, and a four-bay garage. The 1,300 sq ft former stable has been transformed into another heated workspace with 220V power, a kitchenette, a sink, and large sliding barn doors for easy access. The charming 144 sq ft red barn, believed to predate the house and possibly dating back to the 1700s, features traditional mortise-and-tenon joinery and hand-tooled beams. Today it serves as a functional landscape shed while retaining its historic character. History runs deep on the property. The grounds include the historic Sears Cemetery, an 11-memorial family graveyard with stones predating the home's construction. Among those buried here is Hector Craig, a U.S. Congressman and father-in-law to William Havemeyer, part of a family central to the development of early Washingtonville. A rare opportunity to own a fully modernized historic estate, this property seamlessly merges historic integrity, architectural detail, and contemporary comfort across home, land, and workspaces. One Hour to NYC, Close to All Transportations, Dining, Hiking, Shopping and other Conveniences.
Courtesy: eXp Realty
888-276-0630
Welcome to this beautifully maintained 2,318 sq ft Colonial located in the desirable Chester/Sugar Loaf area within the Warwick Valley School District. Set on a landscaped .32-acre lot, this home offers a warm and inviting layout with generous space, natural light, and an ideal setting for comfortable everyday living. The first floor features hardwood flooring and a thoughtful floor plan designed for both relaxation and entertaining. The formal living room provides a bright and welcoming space, while the formal dining room is perfect for gatherings and special occasions. The spacious eat-in kitchen includes granite countertops, stainless steel appliances, a pantry, and a French door that leads to the rear deck. The kitchen flows seamlessly into the family room, complete with a gas fireplace that serves as a cozy focal point and enhances the inviting feel of the home. Upstairs, the primary bedroom offers excellent space along with a walk-in closet featuring built-in organization. Three additional generously sized bedrooms provide flexibility for guests, home office needs, or hobbies. A full hall bathroom serves the additional bedrooms, and the second-floor layout provides comfort, function, and privacy for all. The large unfinished basement, accessible through a Bilco door, offers exceptional storage space and potential for future finishing. Whether you envision a recreation room, home gym, workshop, or simply need ample storage, the basement adds valuable versatility to the property. Outdoor living is a true highlight, with a spacious deck ideal for morning coffee, outdoor dining, or relaxing in the fresh air. The paver patio provides another great space for gatherings, barbecues, and enjoying time with friends. The backyard offers privacy and room for play, pets, gardening, or outdoor enjoyment. Professionally maintained landscaping and hardscaping help create a beautiful and welcoming setting from arrival to backyard. Located in a prime commuter-friendly area, this home offers quick access to major highways, shopping, dining, local attractions, parks, schools, and everything the charming Sugar Loaf and Warwick areas have to offer. With a spacious interior, inviting outdoor spaces, and a well-designed layout, this home presents a wonderful opportunity to enjoy comfort, convenience, and a warm sense of home in one of the region’s most desirable communities.
Courtesy: Prominent Properties Sotheby's
201-768-9300
The one you don't to miss. Nestled on a serene cul-de-sac in the executive subdivision of Country Woods, this magnificent home sits on one of the most beautiful streets within the sought-after Monroe-Woodbury School District. Step into perfection as you enter the grand foyer and are immediately welcomed by a light-filled, open floor plan that exudes elegance and sophistication. This meticulously maintained home showcases exquisite craftsmanship and attention to detail throughout Custom moldings, gleaming hardwood floors, designer lighting, and stately architectural columns that evoke the feel of a Westchester or Bergen County estate. The bright and spacious formal living room flows seamlessly into a warm and inviting family room featuring a stunning custom stone fireplace, elegant mantle, and French doors leading to the outdoors. The expansive chef’s kitchen is a showstopper complete with granite countertops, a large center island, built-in cooktop, double oven, microwave, stainless steel appliances, and a walk-in pantry. Perfect for both everyday living and entertaining. The formal dining room, accented by wainscoting and a lighted niche, provides ample space for memorable gatherings. Upstairs, the luxurious primary suite offers vaulted ceilings, two walk in closets, and a spa inspired bath, along with an adjoining office or private gym. Four additional bedrooms are generously sized, each offering comfort and style. The fifth and second largest bedroom is perfect for guests or extended family. The full, finished walkout basement with 9 foot ceilings and a half bath adds an impressive space for entertaining. Outside, your private backyard oasis awaits featuring a magnificent Trex deck overlooking 3.8 acres of pure tranquility. With its perfect blend of luxury, privacy, and convenience, this exceptional home offers an ideal retreat just a 45 minute commute from New York City.
Courtesy: BHG Real Estate Green Team
845-208-9928
Back on Market. Charming 4-Bedroom Colonial in the Heart of Hudson Valley. Priced to Sell, tons of potential and great commuter location with close proximity to highway! Welcome to this spacious 4-bedroom, 2.5-bath home nestled in the picturesque town of Chester, NY, in the heart of the beautiful Hudson Valley. Offering 2,090 sq ft of living space, plus a finished rec room with an additional 1,026 sq ft, this home is brimming with potential and ready for your personal touch! Step inside to find generously sized rooms, a traditional layout with excellent flow, and a finished basement that opens up endless possibilities—recreation room, home gym, playroom, or even a private studio space. Turn the spacious primary suite into a true retreat, featuring a private screened-in balcony, perfect for enjoying your morning coffee or winding down with a peaceful view at the end of the day. While the home does need a bit of TLC, it's priced to sell and presents a fantastic opportunity for anyone looking to customize a home to their liking. Whether you're a first-time buyer, someone ready to create your dream space, or even an experienced real estate investor, this could be the opportunity you've been waiting for. Solar panels leased $101/month - Lease to be assigned to new buyer. Set on a lovely lot in a quiet neighborhood, you’ll enjoy peace and privacy while still being close to local shops, restaurants, parks, and commuter routes. Chester offers small-town charm with easy access to all the natural beauty and attractions the Hudson Valley has to offer. Don't miss out on this incredible value—bring your vision and make this house your home! Home is being sold AS IS.
Courtesy: eXp Realty
888-276-0630
Welcome to 65 Oxford Springs Road, Chester, NY a custom-built Country Contemporary set on a private, 2.3-acre hilltop. This property offers the perfect mix of privacy, space, and convenience, all just minutes from the NYS Thruway, local state parks, and about 50 minutes from NYC. Inside, the home features a bright, open floor plan with plenty of natural light. You’ll find rich hardwood floors, custom trim work, and impressive 26-foot ceilings that give the main living area a spacious, inviting feel. The living room centers around a striking stone fireplace and flows into a modern granite kitchen with an oversized island and stainless steel appliances ideal for both everyday living and entertaining. The home includes five bedrooms and four bathrooms, with a primary suite that features its own fireplace and a private balcony overlooking the peaceful surroundings. French doors off the dining area lead to a backyard deck that’s perfect for quiet mornings or hosting guests. A standout feature of this property is the two-story detached cottage (approx. 1,000 sq. ft.), offering endless possibilities an art studio, office, guest space, or creative retreat. Recent improvements include a new oil heating system with an above-ground tank. Please note: this home is located on a private road, approximately 0.6 miles from the main road. Experience the charm of country living with the comfort of modern design in this rare Orange County retreat.
Courtesy: Century 21 E & M Williams Rlty
845-778-3543
Nice end unit 3 bedroom 2.5 bath condo with 2 car garage in whispering hills. Primary bedroom with private full bath and 2 nice size extra bedrooms plus a hall bath on the 2nd floor. Warm up on those cold nights with the fireplace in the living room. Enjoy a quiet moment on your private patio sipping your coffee. Great location with playground and tennis across the street, pool, clubhouse and bus stop just 1 block over. Convenient to Route 17, and the NYS Thruway for commuters. Legoland is just 10 minutes away! Convenient shopping, and restaurants nearby. Quaint downtown Sugarloaf shopping area, The Castle Fun Center and local theatre is within a few minutes drive.
Courtesy: Exit Realty Connections
845-298-6034
Motivated sellers. Welcome to Whispering Hills, one of the most sought-after communities in the area with resort style amenities and unbeatable commuter convenience. Picture yourself coming home to this beautiful space. The large living room opens to sliding glass doors that lead out to your private deck, the perfect spot to unwind after a long day. Cathedral ceilings create an open, airy feel, and the fireplace adds cozy charm on cool nights while you enjoy a cup of hot chocolate or a glass of wine. The kitchen has been thoughtfully updated with stainless steel appliances, a five-burner chef’s gas stove, granite countertops, subway tile, and a spacious pantry. The dining area feels peaceful and bright with a large window, plenty of natural sunlight, and a custom window seat with extra storage. Down the hall, the updated bathroom features a new vanity and a relaxing jacuzzi tub. It offers dual entry leading directly into the dressing area, a large walk-in closet, and the main bedroom. The second bedroom is currently being used as a home office. In addition, this unit has been recently freshly painted and includes new luxury vinyl flooring, new light fixtures, and modern upgrades throughout. Enjoy entertaining on your private deck or patio. The one car garage provides additional storage. Additional parking spaces are available. TV mount is included in sale. Maintenance free living is yours with HOA coverage that includes trash removal, water, lawn care, and snow removal. The community features two pools, 2 tennis courts, 2 basketball and handball courts, 2 playgrounds, dog runs, and 2 clubhouses with fully equipped fitness centers. With shopping, dining, access to major highways, and a NYC bus stop right inside the community for an easy commute. This home truly has it all
Courtesy: RE/MAX Benchmark Realty Group
845-565-0004
Discover modern living at its finest in this beautifully designed 2,870 sq ft contemporary home set on 4.1 stunning acres featuring a peaceful pond and a seasonal babbling brook. Offering wonderful privacy and an effortless indoor–outdoor lifestyle, this property is a rare retreat surrounded by nature. Inside, oak hardwood floors flow across both levels, setting a warm yet sophisticated tone. The lower level welcomes you with a sleek entry area leading into multiple stylish living spaces, including a formal living room and a sunken living room with fireplace and sliders that open directly to the expansive backyard. The bright eat-in kitchen features newer stainless steel appliances (dishwasher is brand new!) and is filled with natural light, perfect for everyday meals or hosting. Just off the kitchen, a beautifully versatile room with sliders to the deck offers an effortless indoor–outdoor dining experience. Whether used as a formal dining room or a casual gathering space, it creates a seamless connection between the home’s interior and the natural beauty of the backyard—perfect for al fresco meals, weekend entertaining, or simply enjoying the fresh Hudson Valley air. A recently updated full bathroom, a charming sunroom, laundry/mud room, and a spacious flex room—ideal for a den, playroom, sitting room, office, gym, or guest space—complete this level. Upstairs, the primary bedroom suite impresses with soaring cathedral ceilings, three walk-in closets, and a recently updated en-suite bathroom with modern finishes. Two additional spacious bedrooms share a full hallway bathroom, providing comfort and convenience for family or guests. Step outside to enjoy the peaceful deck overlooking your private natural landscape. The newly fenced backyard is perfect for pets, play, and entertaining, while the oversized two-car garage, whole-house generator, UV light water filtration system, and new gutter guards add everyday practicality and peace of mind. With unmatched privacy, contemporary style, updated amenities, and a breathtaking natural setting, this home offers the perfect blend of elegance, comfort, and escape.
Courtesy: BHG Real Estate Green Team
845-208-9928
Welcome to the Villas at Sugar Loaf — an unbeatable location that rarely sees homes come on the market! Just half a mile from the charming hamlet of Sugar Loaf, this beautifully maintained move-in ready townhome is in the highly sought-after Warwick School District. With easy access to major highways and train stations, this home is ideal for commuters. Inside, you’ll love the bright, open floor plan offering the perfect combination of comfort, convenience, and style — ideal for both everyday living and entertaining. The cozy gas fireplace anchors the spacious living room, which opens to a large deck overlooking lush greenery — perfect for relaxing or grilling. The attached oversized one-car garage, conveniently located off the entryway, provides extra storage. The kitchen was upgraded in 2019 with Wolf cabinets, new appliances, and backsplash. That same year, bathroom vanities and toilets were replaced and in 2020 updating included a new water boiler and softener system. Upstairs, you’ll find three generous bedrooms, including a primary ensuite with a jetted tub and two walk-in closets. A second full bath serves the other two spacious bedrooms, each with ample closet space. The newly painted and carpeted lower level offers plenty of room to expand or create a home office, gym, or recreation area. In 2024, a modern French Drain system was installed as well. Enjoy the culture, dining, and entertainment just steps from your door in quaint Sugar Loaf, home to restaurants, a new gourmet coffee bistro, unique shops, post office, brewery, and the Sugar Loaf Performing Arts Center. You’re also just minutes from the Village of Warwick, known as the “Crown Jewel of Orange County,” offering even more shopping, outdoor activities, dining, and community events. Welcome to your new TOWN and your new HOME!
Courtesy: Howard Hanna Rand Realty
845-928-9691
Discover the perfect blend of comfort, convenience, and community in this 2-bedroom, 1-bath end-unit townhouse. Situated in a quiet corner of the neighborhood, this home offers extra privacy and natural light, along with the added benefit of an attached 1-car garage for secure parking and storage. Inside, you'll find a thoughtfully designed layout that maximizes space and livability - ideal for first-time buyers, downsizers, or anyone seeking a low-maintenance lifestyle. But this home is more than just what's inside. Located in a commuter-friendly community, you'll have access to an impressive selection of amenities designed to enhance your daily life: Two (2) sparkling swimming pools perfect for cooling off in the summer; Two (2) tennis courts, plus basketball and handball courts to keep you active; A fully equipped fitness center just steps from your door; Two (2) playgrounds for little ones to enjoy; and two (2) dedicated dog runs - a dream for your furry friends. Whether you're relaxing poolside, getting in a workout, or taking a stroll with your pup, this community truly offers something for everyone.
Courtesy: Keller Williams Realty
845-928-8000
This is a "Neat as a pin" ranch in the Village of Chester. The kitchen has many updated appliances and a custom pantry with large pull-out drawers. The Living room wood floors were refinished and are immaculate. The bathroom has been updated and built to be ADA-compliant with a space-saving "pocket door." There is a large shed in the backyard, all near all the activities the Village has to offer. 12/1/25: Being shown as backup.
Courtesy: Keller Williams Realty
845-928-8000
A truly rare opportunity to secure over two acres of prime land in the highly desirable and rapidly appreciating town of Chester. This charming property isn't just a home; it's a foundation for your future and a strategic long-term investment. Set on a sprawling 2.1+ acre lot, this property offers the space and privacy that is simply unmatched in today's market. The current single-level structure is neat, practical, and immediately livable, boasting a recently refreshed interior and a key functional update with a new roof installed in 2001. More importantly, the property is inherently designed for growth. With ample acreage, the home presents an easy and exciting opportunity for expansion, allowing you to seamlessly double its footprint, add a master wing, or build the custom luxury features you’ve always wanted. The location is unparalleled. Situated adjacent to an established enclave of newer, high-end construction, your investment here is guaranteed to appreciate. You gain the prestige of a sought-after neighborhood without the price tag of a brand-new build. Despite the serene, private setting, you will enjoy exceptional commuter convenience. Benefit from quick, effortless access to Route 17 and all major retail and dining centers, putting everything you need just minutes away. Generous 2.1+ Acres of usable, private land. Perfect single-level layout ideal for easy future additions. Two-Car Detached Garage providing excellent storage and utility space. Reliable Oil-Fired Heating system with an Above-Ground Tank. Seize the opportunity to purchase an acreage advantage in Chester. This property is waiting for your vision—show and sell!
Courtesy: SHAHAR Management LLC
845-476-7101
Listed on the National Register of Historic Places in the Sugar Loaf Historic District, this stunning Victorian is a Circa 1910 Sears Roebuck Kit Home (#118 The Clyde). Not only is this your dream home located in beautiful Sugar Loaf, NY, it is also zoned for extensive commercial use. Just a 1-minute walk to the quaint Sugar Loaf Arts & Crafts Village, cafes and Sugar Loaf Performing Arts Center. Enjoy morning coffee on the porch and head to work in your office with custom built library and pocket doors on the first level. With a whole house generator on stand-by you never have to worry about a storm leaving you without power. Purchased by an artist this home has been extensively and lovingly restored in every possible way to enhance your living experience. There are custom moldings, central air, central vac system, pocket doors, Navian high efficiency tankless boiler, 50-year shingle roof in 2006, a custom copper Yankee gutter system, and more. Love to cook-the kitchen has beautiful natural lighting and plenty of space for family and friends. When you walk through the door you will know this house is different from the rest and stands above. Just an hour to NYC! USDA Eligible.
Courtesy: MS Realty Group USA, Inc
845-367-7470
Welcome to 10 Damian Court — a stunning custom Colonial set on 2.6 acres of beautifully landscaped grounds in a peaceful Chester cul-de-sac. Built in 2004, this impressive home offers over 4,300 sq ft of elegant living space, featuring 11 bedrooms and 6.5 baths designed for comfort and flexibility. Enjoy a spacious eat-in kitchen with granite counters and pantry, a formal dining area, and a bright family room perfect for gatherings. The primary suite includes a private bath and walk-in closet, offering a true retreat. Additional highlights include central air, a full basement, and a 3-car garage. Surrounded by nature yet conveniently close to major shopping and transit, this property combines serenity and accessibility in the desirable Monroe-Woodbury School District. A rare opportunity to own a home of this scale and quality — schedule your private tour today!
Courtesy: Exit Realty Venture
845-999-3948
Step into this newly renovated contemporary ranch, where comfort meets value on 6.3 acres of peaceful living. Featuring 4 spacious bedrooms and 3.5 bathrooms, this home has been beautifully renovated with new plumbing, spotlights, flooring, kitchen, painting, and full wiring for a camera and security system. Enjoy a large eat-in kitchen, formal dining room, cozy family room, and a bright attic with a full bedroom and bath — ideal for guests or a private retreat. The seller made major improvements, giving the home a fresh, modern feel that looks and feels brand new. Located in a quiet neighborhood with friendly neighbors and easy access to shopping areas. An opportunity you don’t want to miss — grab this deal before it’s gone!
Courtesy: Keller Williams Realty
845-928-8000
Set back on a quiet street, just steps from downtown Sugar Loaf is this large home on almost an acre. Walk into the open living room and dining room, open to the kitchen with stainless steel appliances. The primary bedroom has access to the back deck, perfect for sipping your morning coffee overlooking the large peaceful backyard. Two additional bedrooms and a full bath complete the main floor. More space on the lower level with family room includes attached office/craft/bonus room. With the fourth bedroom and a full bath on this level, this could easily lend itself to an "in-law"/mother-daughter au-pair set up, etc. Easy walk to the Arts and Crafts village of Sugar Loaf with unique shops, multiple restaurants, and the Sugar Loaf Performing Arts center. All of this in the desirable Warwick Valley Central School District! Driveway just sealed, new walkway, roof 2021
Courtesy: Century 21 Full Service Realty
845-782-2221
Welcome to your private, wooded oasis! This charming home perfectly blends convenience with comfort, featuring an ideal layout for multi-generational living or guests with two bedrooms and a full bathroom on the main floor. A cozy wood insert is the heart of the main living space, creating both warmth and a wonderful ambiance on chilly evenings. Beyond the existing bedrooms, there is additional flexible space on the main floor that could serve as a dedicated office, den, or playroom. The current owners are maximizing the space by utilizing it as a third main-floor bedroom. Unbeatable Outdoor Entertainment Step outside to your incredible backyard retreat. This true oasis features a heated pool, a charming fire pit for evening gatherings, and a spacious back patio with awnings that offers plenty of room for outdoor dining and cooking. An added outdoor shower is perfect after a swim. For the culinary enthusiast, the sellers have built three outdoor ovens! Expansive Acreage and Versatility The property spans a generous five acres, offering incredible space and flexibility. Two acres are fully fenced, creating a secure area, while the remaining three acres are perfect for recreational vehicles, ATVs, or other outdoor pursuits. A unique feature is the additional sunroom, currently serving as a dedicated space for a home-based business, offering even more versatility. Spacious Second Floor Sanctuary The second floor is dedicated to relaxation and space, featuring a total of three bedrooms. The primary suite is a spacious haven complete with a private ensuite bath. The primary bedroom boasts a huge closet and there's a huge hall closet that offers exceptional storage for the second floor. The second upstairs bedroom also offers great comfort and has access from the bedroom to the second full bathroom. The third bedroom on the second floor provides extra space for family or guests. This home is a perfect blend of indoor comfort, dedicated main-floor living, outdoor entertaining, and acreage for all your hobbies!
Courtesy: Howard Hanna Rand Realty
845-986-4848
Welcome to Country Woods, one of Chester’s most sought-after neighborhoods. This handsome Colonial sits on 1.7 landscaped acres and offers over 3,100 square feet of comfortable living space. A wrap-around front porch invites you inside, where a two-story foyer and 9-foot ceilings create a bright and spacious feel. The formal living and dining rooms flow seamlessly into the kitchen, complete with Corian counters and everything you need to prepare your favorite meals. The casual dining area opens to a warm and inviting family room featuring a vaulted ceiling, fireplace, and a wall of windows framing peaceful views — the perfect spot to gather for movie or game night as you watch the snow falls outside. A first-floor bedroom offers flexible space for a home office, guest suite, or quiet meditation room. A conveniently located laundry room and half bath complete the main level. Upstairs, unwind in the primary bedroom suite, plus three additional bedrooms and a full hall bath. Need more space? The full walk-out basement provides endless possibilities — a home gym, game room, or recreation area — the choice is yours. Step outside to enjoy your own private retreat, ideal for entertaining, gardening, or simply relaxing on the oversized deck overlooking a tranquil Koi pond with waterfall and wooded backdrop. Conveniently located near major commuter routes, shopping, Woodbury Common Premium Outlets, schools, cafes, and restaurants — this home truly has it all. Call today to schedule your private tour and spend the holidays in your new home.
Courtesy: Four Seasons Sothebys Intl
518-822-0800
Set on 10 private acres with sweeping mountain views from nearly every room, 69 Cedar Pond is a five-bedroom, eight-bath estate that exemplifies expansive design and contemporary style. The striking A-frame architecture, double-height windows, and soaring ceilings create dramatic, light-filled interiors where every angle frames the surrounding landscape and sunsets. A three-story entry sets the tone, leading into an open great room anchored by a statement fireplace. Walls of glass blur the line between indoors and out, opening to an 1,800 sq ft deck that wraps the home with extraordinary vistas and flows seamlessly to an outdoor bar, dining, and lounge area with fire pit—perfect for entertaining on a grand scale. Expansive spaces continue throughout the main level, which offers two bedrooms with luxurious en suite baths, a powder room, a chef's kitchen, a dining area, and a breakfast nook. Upstairs, the primary suite is generously scaled, with sweeping views and a spa-like bath featuring a soaking tub, private water closet, and double vanity. This level also includes an additional bedroom and a fully renovated guest wing with its own kitchen, great room, bedroom, bathroom, private balcony, and separate exterior entrance for added privacy. The versatile lower level includes a family room, gym, two bedrooms, a wet bar, and walk-out access to the property's outdoor amenities. Every major element has been thoughtfully upgraded—new roof (2020), mechanicals and electrical (2019), furnace (2019), luxury baths (2021), and kitchen appliances. Despite its impressive scale, energy-efficient systems keep the home comfortable and remarkably cost-effective. The 10-acre property is as versatile as the home itself: enjoy private hiking trails, host open-air gatherings, or create a resort-style retreat with a pool, tennis court, or gardens. Nearby vineyards, ski slopes, and Hudson Valley attractions complete the lifestyle.
Courtesy: Keller Williams Hudson Valley
845-610-6065
Discover the perfect blend of versatility and charm with this exceptional property. The main house offers three levels of comfortable living, including four bedrooms, three baths, and a spacious kitchen ideal for gathering and entertaining. The thoughtfully renovated barn extends your options with beautifully finished space that carries rustic character alongside modern updates. Whether you envision a studio, home office, entertainment area, or creative retreat, the barn provides a unique extension to the main home. This property opens the door to endless possibilities make it yours today!
Your Adirondack Sanctuary: Spacious Home Near Gore Mountain Skiing! This charming and distinctive ski house offers the perfect blend of character and convenience on a generous 1.57-acre lot, just 8 miles from Gore Ski Mountain. The home features four bedrooms and one and a half baths, with the primary bedroom conveniently located on the first floor for easy accessibility. The spacious dining room provides an ideal gathering space for meals and entertaining guests after a day on the slopes. Outdoor enthusiasts will appreciate the dedicated gear room with its own outside entrance, perfect for storing ski equipment and wet gear without tracking snow through the main house. The three-season room extends your living space and offers a wonderful spot to enjoy the changing seasons, while the laundry room comes equipped with newer appliances for added convenience. The property boasts a beautiful yard with established gardens and existing fencing that's perfect for pets, making this an ideal retreat for families seeking a unique mountain getaway with both indoor comfort and outdoor appeal. New septic/leachfield as of October 2025
Courtesy: River Realty Services, Inc.
845-564-2800
One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space.Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk to the village!
Courtesy: Our House Real Estate Group
845-705-8093
A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This will truly be a lovely property with land, privacy and wonderful mountain views! This modern farm house cape features over 2,600 sq ft. and is completely CUSTOM and DELIVERED TURN-KEY ... build this home, or bring your own dream plans/ideas! This ONE LEVEL living floor-plan features a primary bedroom suite with full bath and walk-in closets plus a second first floor bedroom or office; a wonderful kitchen/great-room open floor plan and walk-in pantry; formal dining room; fabulous front and rear covered porches and more! Optional finished bonus room on the second level can add an additional 410 sq ft. .... Buyer-Financed CONSTRUCTION TO PERM FINANCING OR CASH ONLY.... Very commutable plus minutes from the vibrant town of Sugar Loaf and Chester, NY!... TO BE BUILT, may have additions/subtractions to price for customization, the taxes are not known at this time, and the attached photos may be computer-generated images and are depictions of what the property may look like.
Courtesy: Our House Real Estate Group
845-705-8093
ONE LEVEL LIVING/ EASY COMMUTE- with additional space upstairs and down! ... Don't miss this beautiful TURN-KEY Arts & Crafts-style FARMHOUSE TO BE BUILT! ..... COME AND FULLY CUSTOMIZE this 4-bdrm, 3 bath, 2,106+/- sq. ft home (including bonus room)! LARGE MAIN FLOOR PRIMARY BEDROOM with ENSUITE BATH & WALK-IN CLOSET plus A SECOND MAIN FLOOR BEDROOM (NURSERY, OFFICE, CRAFT ROOM ETC.). FANTASTIC VAULTED FAMILY ROOM WITH LARGE FIREPLACE (GAS OR WOOD-BURNING), GOURMET KITCHEN with eat-in breakfast area and PANTRY including a convenient pass-through window to the family room! Separate DINING ROOM with French doors to the back plus a FULL HALL BATH and convenient LAUNDRY area. Upstairs offers 2 ADDITIONAL LARGE BEDROOM with WALK-IN CLOSETS & another large full bath. ....Finish the optional second floor bonus space for an office, bedroom, gym, studio and more for an extra 239 sq ft! Two-car garage with convenient access right to the kitchen for easy grocery loading PLUS a FULL WALK- OUT BASEMENT!! ..... BUYER-FINANCED BUILD: CASH OR CONSTRUCTION-TO-PERMANENT LOAN ONLY. ..... CALL TO SCHEDULE A TOUR OF THE LOT & schedule a builder's meeting. This will be a fantastic home with all high end finishes, standard! Lovely 1-Acre lot w/MOUNTAIN VIEWS ... VERY COMMUTABLE!
Courtesy: Keller Williams Hudson Valley
845-610-6065
Welcome to this beautifully maintained colonial with a charming wrap-around front porch, set on 1.5 private acres within the sought-after Monroe-Woodbury School District. Offering over 3,100 square feet of living space, this 5-bedroom, 2.5-bath home blends timeless style with thoughtful design. Step inside the two-story foyer and you’ll find a bright, flowing layout designed for both everyday living and effortless entertaining. Gleaming hardwood floors, generous living spaces, and quality finishes create a warm and welcoming atmosphere throughout. The family room features a vaulted ceiling, wood-burning fireplace, and abundant natural light—beautifully showcased from the open upstairs landing above. The gourmet kitchen is equipped with high-end appliances, a pantry, and an open dining area that leads to a back deck overlooking the expansive backyard—ideal for outdoor entertaining. A formal dining room offers an elegant space for hosting. A main-level bedroom provides flexible options for use as an office, gym, or guest space. The mudroom offers convenient storage for coats and shoes, keeping daily routines organized. Upstairs, the spacious primary suite is a true retreat with tray ceilings, two walk-in closets, and a luxurious en suite bath with a jetted tub and separate shower. Three additional bedrooms and a full bath complete the second floor. A full, unfinished basement presents endless possibilities for customization. Additional highlights include a laundry room, electric pet fence on the full perimeter of the property, and a large, private yard offering the perfect blend of privacy, comfort, and space. Stunning exterior lighting provides striking curb appeal and ambiance in the evening. Don’t miss the opportunity to make this spacious, light-filled colonial—set on 1.5 private acres—your forever home. Schedule your private showing today.
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Chester is located in New York. Chester, New York has a population of 12,477. Chester 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 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 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.
