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$3,925,000
4 Beds 3 Baths 993208 MLS
Flywheel Farm. An exceptional, state-of-the-art equestrian facility, designed with the accomplished professional in mind. Set in an unbeatable location - just 2 miles from international show jumping venue Old Salem Farm. Nestled behind private gates on nearly 9 picturesque acres with rolling fields and every amenity for the horse and rider. Impressive 112’ x 200’ outdoor arena with prized Lawton Adams TravelRite footing - surrounded by lush trees and 140 acres of Putnam Land Trust protected space. The stunning, custom-built barn, completed in 2019, is not only elegant, but highly functional. Featuring eight 12’x12’ European style stalls with dutch doors, extra-wide rubber matted aisles, a heated wash stall, two grooming stalls, climate-controlled tack room with laundry & powder room, heated feed room, supply room, expansive hayloft, fly spray system, camera security system and a Sonos surround sound system. There is a superb attached 80’ x 160’ fully insulated indoor arena with TravelRite footing, large windows, and 18 foot ceilings - ideal for year-round riding. Three belgian block covered porches surround the barn for relaxing and watching riders in the shade. There is a light-filled 3 bedroom, 2 bathroom trainer’s cottage with soaring ceilings, floor to ceiling windows, gleaming hardwood floors, woodburning stove, 1 car garage, and a large deck for entertaining. There is also a 2-bay equipment garage with a luxurious, fully updated, 1 bedroom, 1 bathroom apartment above. Beautiful, open grounds with seven large grass turnout paddocks - one with run-in shed stall, plus two additional medical paddocks. Close proximity to area horse shows: Old Salem, HITS Saugerties, CSI Greenwich, Fairfield Hunt Club and Silo Ridge. North Salem schools. This is as turn-key as it gets in the heart of horse country.

4 Star Cobb Lane, Brewster

$1,530,000
5 Beds 6 Baths 1010448 MLS
Exquisite Custom Colonial Estate on Nearly 6 Private Acres with Resort Style Grounds. Presenting a truly exceptional, original owner and custom built Colonial, gracefully set on 5.98 idyllic acres and backing onto a picturesque 100-acre equestrian estate. Encompassing 8,036 square feet of refined living space, this distinguished residence offers 5 bedrooms and 5.5 bathrooms, expertly designed to blend timeless elegance with modern comfort. From the moment you arrive via the circular driveway, framed by manicured gardens and a stately flagpole, the home’s grandeur and craftsmanship are unmistakable. Rich wood siding, a classic wraparound porch, and thoughtfully curated architectural details set the tone for the sophisticated interiors within. The home is designed for both luxurious everyday living and effortless entertaining, featuring a gourmet kitchen, sun-drenched sunroom, elegant home office, expansive bonus room with a home gym, and a beautifully finished walkout basement leading to an expansive patio. Every space reflects quality, scale, and comfort. Step outside to your own private resort. The sprawling, park-like grounds provide a spectacular setting for gatherings both large and intimate. The outdoor oasis features a stunning in-ground heated Gunite pool, hot tub, and an exquisite pool house complete with wet bar, full bathroom, and its own covered deck...creating an unmatched environment for hosting and relaxation. Multiple outdoor living areas, including a screened-in porch and oversized deck, seamlessly extend the home’s entertaining potential. Additional luxury amenities include central air conditioning, central vacuum, automatic whole-house Generac generator, and a comprehensive alarm system, along with a 3-car attached garage. Privately nestled on a country road in scenic Brewster, this remarkable estate offers the rare combination of tranquility and convenience, just minutes from I-84, I-684, Route 22, Metro-North train service, Richter Golf Course, Danbury Fair Mall, and fine dining. A rare opportunity to own a one-of-a-kind legacy property where elegance, privacy, and lifestyle converge.

290 Joes Hill Road, Brewster

$1,443,618
6 Beds 5 Baths H6245131 MLS
Ballad model, just completed on Lot 28-N. Incredible, quality built. Many customizations on this specific home include spectacular floor-to-ceiling stone & tile fireplace, first floor expansion to enlarge family room, finished upper level walk-in attic space for guest room and full bath (adds 300 sq ft, and creates 5th bedroom, this one with ensuite bath), and finished basement area of approx. 750 additional sq. ft. with family room, 6th bedroom and another added full bath. Amenities in all models: Cathedral Ceilings, Granite Kitchens w/Custom Cabinets, Open Floor Plans, Luxurious Primary Bedroom Suites w/Walk-In Closets, 2 or 3-Car Garages. Fortune Ridge residents enjoy spectacular Clubhouse, complete w/2 Pools, Tennis & Basketball Courts, Exercise Room, Children's Playroom, Catering Kitchen, Neighborhood Gathering Room & more! Equestrian Center w/Pastures, Stables & Riding Ring. Private Hiking Trails. Most lots back up to Greenspace - over two thirds of the 300-acre Fortune Ridge property will remain “Forever Green”. (HOA Fee: $150/month. Water/Sewer: estimated at $200/month; will be billed based on usage.) Taxes are Approximate. Convenient to Croton Falls Train Station.

71 Stonehollow Drive, Brewster

$1,325,000
5 Beds 6 Baths 905655 MLS
Nestled in the heart of the highly sought-after Indian Wells community, this spectacular custom home is a true masterpiece. Both the exterior and interior exude perfection, offering a blend of sophistication and comfort at every turn. The beautifully renovated expansive floor plan, designed with both entertaining and relaxation in mind, boast over 6,000 sq. ft. (independently measured) of living space. The 1st floor layout features gracious living and dining rooms, and a gourmet chef’s kitchen, complete with top-tier Viking appliances, which flows seamlessly into the spacious family room complete with cathedral ceilings and a raised hearth stone fireplace, making it perfect for gatherings of any size. A breathtaking first floor primary bedroom suite features an ensuite bath, oversized walk in closets and a private deck that overlooks the stunning gunite pool—your very own oasis. Whether you're waking up to serene views or enjoying a quiet evening, this space offers ultimate tranquility. For added convenience, the first floor also includes a versatile multi-purpose room, ideal for in-laws, nanny or weekend guests. This private suite features its own full bedroom, bath, and small kitchen prep area, ensuring independence and privacy. This renovated and turn-key home is filled with high-end finishes and luxury details, including a large wrap around deck and a fully equipped gym. With a sprawling 3.21-acre lot, the expansive yard offers ample space for outdoor activities, from sports to leisure, all set in a beautifully landscaped environment. The private heated pool area provides a serene backdrop for sun-soaked afternoons. For those seeking the perfect blend of modern living, privacy, and elegance, this Indian Wells gem is truly a once-in-a-lifetime opportunity.

62 Indian Wells Road, Brewster

$1,300,000
4 Beds 5 Baths 892338 MLS
Custom-built & Quality-built home. First time on the market. Priced to Sell. 55 Enoch Crosby Road is a lovely Contemporary Colonial complete w/Accessory Apartment, 4-car heated garages and showcases a thoughtful and well-planned design. Tucked away on a peaceful 5.5-acre property, your private, lighted, tree-lined drive leads you home to serene & peaceful grounds featuring a 16 X 38 ft. heated in-ground pool. Inside you will be greeted by an open foyer w/inlaid flooring, formal dining room, family room/den, sunken living room w/gas fireplace, radiant floor heat and a wall of custom doors & windows that allow natural sunlight to radiate. Crafted w/quality and designed for comfort, this home offers generous living spaces and striking ceiling height throughout. The convenient & well-proportioned first-floor primary suite boasts double walk-in closets, floor-to-ceiling tiled shower, Jacuzzi tub, radiant floor heat and direct access to the private outdoors. Eat-in kitchen is appointed w/granite countertops, gas range, large pantry, wine fridge, double wall oven, radiant floor heat & ample cabinet/counter space. The main level also includes a half bath, first floor laundry room thoughtfully designed w/custom dog bath. The 2nd floor recreation area provides the perfect setting for relaxation & fun, complete w/a full-size pool table, cozy lounge areas, and a generous-sized 2nd family room nearby. The open catwalk layout overlooks the main level and connects two large bedrooms, bonus room, full bath & convenient hall office space. The Accessory apartment provides many opportunities (extended family living, in-law/mother daughter, rental income, Airbnb, home office/business). Inside you will find a spacious one-bedroom apartment w/radiant floor heat, private deck w/awning. Plenty of storage throughout including a full walk-up attic & full walk-out basement w/woodburning stove and additional full bath. If you are looking for a unique & custom-built home that TRULY HAS IT ALL – you have found it! The Enoch Crosby area is located in a sought-after community near the Middle Branch Reservoir, golfing, bike paths, local restaurants, shopping & Danbury CT. GREAT commuter location with its close proximity to Metro North Train Station, Route 684/84, 27 miles to Westchester County Airport, 30 miles to White Plains, 59 miles to NYC.

55 Enoch Crosby Road, Brewster

$1,191,003
4 Beds 3 Baths H6244218 MLS
Accepted Offer. This Bravo model, set on Lot 30-N. (Photo Shown is of Similar Model Already Built & Occupied.) *ALL Homes are TO BE BUILT.* Your chance to own one of 103 new single family homes in this totally inclusive community. Incredible, quality built. Amenities: Cathedral Ceilings, Granite Kitchens w/Custom Cabinets, Open Floor Plans, Luxurious Primary Bedroom Suites w/His & Hers Walk-In Closets, 2 or 3-Car Garages. Fortune Ridge residents enjoy spectacular Clubhouse, complete w/2 Pools, Tennis & Basketball Courts, Exercise Room, Children's Playroom, Catering Kitchen, Neighborhood Gathering Room & more! Private Hiking & Riding Trails. Most lots back up to Greenspace - over two thirds of the 300-acre Fortune Ridge property will remain “Forever Green”. Choose your dream home! (HOA Fee: $150/month. Water/Sewer: estimated at $200/month - will be billed based on usage.) Taxes are Approximate. Convenient to Croton Falls Train Station. Additional Information: ParkingFeatures:2 Car Attached,

70 Stonehollow Drive, Brewster

$1,152,000
4 Beds 5 Baths 1004187 MLS
Discover this charming and elegant Farmhouse Colonial home offering approximately 4,300 sq ft of living space on a stunning 7 acre park like property in Southeast, NY. Featuring 4 generously sized bedrooms and 4.5 baths, this residence boasts the rare luxury of 4 fireplaces-one each in the Principle bedroom, living room, dining room, and kitchen. This home includes a thoughtful addition with its own separate entrance, a second floor, and a full bathroom, making it ideal for au-pair suite, extended family, guests or home office. The home sits at the end of a long, winding driveway, surrounded by mature trees and beautiful landscaping. Enjoy the heated in-ground pool and hot tub with a spacious surrounding patio, perfect for entertaining. Additional highlights include a detached 2 car garage with attached gym, PLUS a potential subdividable building lot.-offering endless potential for expansion or future development. Freshly painted. Recently refinished gleaming hardwood floors, as seen. Floors recently While the kitchen awaits your personal touch, this exceptional property provides the perfect canvas to create your dream home in a serene, private setting. Bordering North Salem and Croton Falls it is minutes to 1-684 and Metro North Train Station.

136-140 Guinea Road, Brewster

$1,150,000
4 Beds 3 Baths 900090 MLS
Welcoming 4-Bedroom Colonial in Fortune Ridge – Perfect for Relaxing or Entertaining! Built in 2019 with significant upgrades and beautifully maintained, this 4-bedroom, 2.5-bath home sits on a lush, professionally landscaped 0.81-acre property that’s as private as it is picturesque. Inside, the inviting open layout includes a formal living room, formal dining room, and a sunny eat-in kitchen with stone countertops and stainless steel appliances that flows seamlessly into the spacious family room—perfect for gatherings big or small—with a cozy gas fireplace as the centerpiece. An all-season sunroom with cathedral ceilings offers the perfect spot to enjoy the beauty of every season. Upstairs, the primary suite is a private retreat with two walk-in closets and a spa-inspired bath. Three additional bedrooms and a full hall bath complete the second level. The walk-out lower level features a large, versatile finished space—ideal for a gym, recreation room, or media area—plus abundant storage. Step outside to multiple Trex decks, including a custom pergola with retractable screens, lighting, and adjustable louvers for the perfect balance of sun and shade—an entertainer’s dream. Professionally designed solar and electric landscape lighting enhance both the front and back yards, creating a warm, inviting glow in the evenings while highlighting the property’s natural beauty. For garden enthusiasts, a custom greenhouse provides the perfect space to cultivate herbs, flowers, or seasonal vegetables year-round, adding both beauty and function to the grounds. In Fortune Ridge, you’ll enjoy resort-style amenities: clubhouse, pool, tennis, basketball, playground, gym, over six miles of walking trails, and even an on-site equestrian facility. Convenient to Metro North, highways, shopping, dining, and schools. There are simply too many wonderful features to list here—request the full features and upgrades list for all the details!

31 Stonehollow Drive, Brewster

$1,100,000
4 Beds 4 Baths 945099 MLS
Welcome to 18 Stonehollow Drive, a beautifully appointed home nestled within the highly sought-after Fortune Ridge community in Brewster. Thoughtfully designed and meticulously maintained, this exceptional residence offers effortless, move-in-ready living with nothing left to do but enjoy. A striking foyer sets the tone upon entry, opening to bright, open living spaces enhanced by built-in Sonos ceiling speakers and smart-home features powered by a Nest system. The kitchen is both stylish and functional, featuring man-made stone countertops and ample space for everyday living and entertaining. While officially a four-bedroom home, the layout lives like five, offering flexible spaces to accommodate guests, a home office, or additional living needs. The home offers three and a half baths, including a tranquil primary suite featuring motorized blinds in the bathroom for added comfort and privacy. A conveniently located laundry room on the main level adds to the thoughtful design. The finished lower level includes a finished bedroom and a versatile bonus room ideal for a home office, gym, media room, or play space. Step outside to take in breathtaking, 180-degree exceptional views that truly must be seen in person to be fully appreciated. An expanded deck and a stunning bluestone patio completed in 2024 create the perfect backdrop for both entertaining and quiet moments at home. Additional highlights include durable hardboard siding, a rare natural gas connection for the home, a full-house generator, a booster pump providing excellent water pressure, private community water and sewer, and a three-car garage offering ample storage and parking. Fortune Ridge residents enjoy access to a community clubhouse with a fitness center, along with tennis courts, a basketball court, and multiple pools. Ideally located close to shopping, dining, the train station, and major highways, this home offers the perfect blend of luxury, convenience, and lifestyle. A truly turnkey offering in one of Brewster’s premier communities.

18 Stonehollow Drive, Brewster

$1,085,147
3 Beds 3 Baths H6245242 MLS
Forte model with expanded Kitchen & Front Porch just completed on Lot 33. Incredible, quality built. Upgrades on this home: Expanded Kitchen addition; Fireplace; Rough plumbing in Basement for future bath + double egress window; Finished extra room (home office) on upper level; Full house automatic generator. Fortune Ridge Amenities: Cathedral Ceilings, Granite Kitchens, Open Floor Plans, Luxurious Primary Suites, 2 or 3-Car Garages. Fortune Ridge residents enjoy spectacular Clubhouse, complete with 2 Pools, Tennis & Basketball Courts, Exercise Room, Children's Playroom, Catering Kitchen, Neighborhood Gathering Room & more! Equestrian Center with Pastures, Stables & Riding Ring. Private Hiking Trails. Most lots back up to Greenspace - over two thirds of the 300-acre Fortune Ridge property will remain “Forever Green”. Choose your dream home now! (HOA Fee: $150/month. Water/Sewer: estimated at $200/month - will be billed based on usage.) Taxes are Approximate. Convenient to Croton Falls Train Station.

60 Stonehollow Drive, Brewster

$995,000
2 Beds 2 Baths 932277 MLS
Welcome to Your Peach Lake Retreat! Experience lakeside living at its finest in this turnkey 2-bedroom home that lives like a 3-bedroom, set within the sought-after Vails Grove Lake Community, offering breathtaking views and direct water access for all your lake toys. Enjoy boating, swimming, and fishing in the summer, or ice skating and ice fishing in the winter. One of the few motorboat-friendly lakes in the area, Peach Lake provides true year-round enjoyment. Vails Grove residents enjoy private amenities including lake and docking rights, a lifeguard-attended beach, playground, basketball court, and a lakefront pavilion with year-round community events. Inside, this sun-filled home blends rustic charm with modern comfort. The open floor plan features skylights in every room, pine floors, and reclaimed wood accents throughout, adding warmth and character. Step into a warm and inviting living room perfect for relaxing and entertaining. A mid-century fireplace adds both warmth and charm. The high, beamed ceilings enhance the sense of space and architectural character. Fold-out doors to a spacious deck with panoramic lake views. The kitchen showcases a stainless farmhouse sink, subway tile backsplash, LG fridge, Bosch dishwasher, and beverage fridge. The primary suite offers lake views, barnwood doors housing a walk-in closet, updated bath. A second bedroom and full bath complete the main level. The lower level features versatile recreational space, a guest room/office with custom closets, a bathroom with heated floors, and walk-out access to a patio. Outdoors, enjoy the fountain pond, expansive backyard with stone walkways, vegetable gardens, outdoor bar, shed, and a Wi-Fi–equipped lakefront patio. The maintenance-free aluminum dock provides effortless lake access, and the jet ski with trailer is included. Additional features include outdoor lighting, abundant electrical outlets, and garage #5 may be transferred to the buyer for a fee. This home is the ultimate year-round lake retreat, perfect for living and entertaining. Conveniently located near I-84 and 684, three golf courses, the Danbury Mall, and a variety of dining and shopping options. See documents for additional facts & features.

69 Vails Lake Shore Drive, Brewster

$900,000
5 Beds 4 Baths 886319 MLS
Travel back in time with this enchanting historical home that effortlessly combines old-world charm in a bucolic neighborhood nestled next to a castle. Sitting on a generous 1-acre lot and constructed in 1790, this delightful property is brimming with character around every corner. The main floor boasts a lovely staircase, cozy parlor, welcoming living room with a fireplace, dining room, kitchen with a butler's pantry, au-pair entrance, and more. Upstairs, discover 5 bedrooms, 3 bathrooms, and a back staircase leading down to the au-pair area. Relax on the screened-in porch with access to the flagstone patio, or enjoy the expansive rear yard perfect for gatherings, barbecues, and cozy nights by the fire pit. Balanced between historic elegance, this sprawling property offers original beamed ceilings and hardwood flooring, natural gas, solar panels, and convenience - located near major highways, shopping, schools, and restaurants. This property is a must-see! Come take a trip back in time and explore this charming slice of history.

115 Turk Hill Road, Brewster

$895,000
4 Beds 4 Baths 1004945 MLS
This impeccably maintained home has off the charts "WOW factor!" Located on a quiet cul de sac in a beautiful neighborhood, you will find 40 Farrell Dr perched happily atop a hill with views of the distant mountains. Incredible curb appeal is just the beginning! Around the back, up the stone steps, is a summer entertainer's dream. The heated inground salt water pool is surrounded by a stamped concrete patio, gorgeous plantings and a gazebo all in a very private backyard setting. Inside, you'll find a move-in ready home with a mother-daughter setup. The main level has a total of 2.5 baths and 3 bedrooms, one of which is an oversized primary bedroom with a large walk-in closet and recently updated ensuite bath, plus an office. The second level of the home has a full bath, large den with tons of closet space, and the 4th bedroom in the house; shared utilities with its own heat zone and mini-split AC. There is a private, exterior entrance to the second level finished attic space, as well as access from the main level making this the perfect compound or au pair suite. Enjoy preparing and eating meals in the updated, eat-in kitchen composed of a 5 burner electric cooktop, double ovens, stone counters and tons of cabinet space. Conveniently located off the kitchen is a mudroom with a half bath and access to the backyard, easy access for pool party guests. The dining room is trimmed with thick crown molding and leads into the sun-filled formal living room with hardwood floors. For quieter days, relax by a fire in the large den that leads to the covered, screened-in porch. Storage is no problem in this home! There's tons of storage in the unfinished basement and additional storage in the super clean crawl space accessible from within the garage. And for your outdoor toys and tools, there's an attached shed space next to the garage and detached shed in the backyard. Even the garage is immaculate with new epoxy flooring, water spigots to easily wash cars and a generator hookup. And your dogs will love it, too, with an invisible fence already setup! You truly need to tour this home to appreciate how well thought out and special it is, inside and out!

40 Farrell Drive, Brewster

$875,000
4 Beds 3 Baths 1002558 MLS
Set on five private acres in the Hudson Valley, 22 Indian Wells Road offers the kind of space, privacy, and natural beauty that feels increasingly rare — all while keeping you close to everyday conveniences, Metro-North, local restaurants, shops, parks, and the charm of Brewster and the surrounding Hudson Valley towns. Tucked away in a quiet development, this property immediately sets the tone with a peaceful, retreat-like setting surrounded by mature trees, open outdoor space, a large backyard pond, and a mix of peach and nectarine trees. Whether you’re dreaming of quiet mornings, summer entertaining, room to garden, space to explore, or simply a home that gives you room to breathe, this property delivers a lifestyle that feels both grounded and elevated. Inside, the home is bright, warm, and thoughtfully designed, with hardwood floors flowing throughout the first and second levels, 9-foot ceilings on the first floor, and oversized floor-to-ceiling windows that bring in beautiful natural light. The family room serves as an inviting gathering space, complete with a fireplace and French doors that lead directly out to the bluestone patio — seamlessly connecting indoor comfort with outdoor living. The chef’s kitchen is both stylish and functional, featuring all-new stainless steel appliances, granite countertops, a pantry, a breakfast bar, and an eat-in layout ideal for everyday meals, morning coffee, and casual entertaining. For more formal gatherings, the dining room offers a dedicated space to host holidays, dinner parties, and special occasions. The home’s layout is designed with both convenience and flexibility in mind, including a laundry room conveniently located on the first floor and a 3-car attached garage with loft space and enough room for a lift to be added. Upstairs, in addition to three bedrooms, the primary suite offers a true retreat with a large walk-in closet, a bonus space that could be used as an office or second oversized walk-in closet, and an en-suite bath featuring a stall shower, dual sinks, and a jacuzzi tub. Outdoors, the five-acre setting is the true centerpiece. The bluestone patio provides the perfect place to dine, entertain, or unwind while overlooking the natural beauty of the property. From the house, you can hear the peaceful sound of water flowing through the backyard stream, which winds beneath charming bridges and leads you toward the expansive fields at the back end of the property. A large pond, mature fruit trees, a chicken coop, and a chicken run further enhance the property’s unique charm and offer a rare opportunity to enjoy a more peaceful, self-sufficient Hudson Valley lifestyle. Offering the perfect blend of privacy, character, possibility, and convenience, 22 Indian Wells Road is more than just a home — it’s a private Hudson Valley escape with the space to make it your own.

22 Indian Wells Road, Brewster

$875,000
4 Beds 4 Baths 997282 MLS
This is the one you’ve been waiting for! The perfect mix of social hub and private sanctuary. Meticulously maintained home nestled on a quiet cul-de-sac along NY-CT border, perfect for family living and entertaining. The home features a spacious yet cozy living room with wood-burning fireplace, chef's kitchen will all new appliances, formal dining room, a private primary suite, and 3 nicely sized additional bedrooms. Plus an additional 335 SF of attic storage. The finished lower level offers exceptional flexibility and can serve as an in-law suite, playroom, gym, media room with bar—ideal for guests or multi-generational living. Recent updates include a NEW ROOF (2024), new kitchen appliances (2024), and a new pool liner (2021). Conveniently located near the Metro-North Southeast station and tons of amenities in both the NY and CT directions. TURN KEY AND READY TO ENJOY!

9 Rose Lane, Brewster

$855,000
3 Beds 2 Baths 992277 MLS
Main house plus cottage! Set in a beautiful, private setting near the reservoir and located on a quiet dead-end road, this sprawling ranch offers space, versatility, and endless potential. The main home features 3 bedrooms and 1.5 bathrooms, along with a 3-car garage—two bays together plus a separate third bay, all attached for convenience. The property also offers two separate driveways—one for the main house and one for the cottage—providing added privacy and functionality. A spacious living room with a large picture window fills the home with natural light, creating a warm and inviting atmosphere. Hardwood floors run throughout the home, currently protected under carpeting, waiting to be revealed. While the home reflects its original style, it has been meticulously maintained and is exceptionally clean—ready for a new owner to bring their vision and personal touches. The large eat-in kitchen features a breakfast bar and offers plenty of space for everyday living and entertaining. The main level also includes a cozy wood-burning fireplace and a flexible bonus space that can easily serve as a dining area, den, home office, or playroom—whatever suits your lifestyle. The expansive semi-finished walkout basement provides incredible additional living space, complete with a wood-burning stove, a dedicated wine cellar, and a retro-style bar that feels like a fun throwback to the 70s—perfect for entertaining. Whether you envision a recreation room, family room, or home gym, the possibilities are endless. Step outside to enjoy the in-ground pool, surrounded by privacy and natural beauty—ideal for relaxing or hosting guests. A covered front porch offers the perfect spot to unwind—whether you're enjoying your morning coffee in a rocking chair or a glass of wine in the evening. A standout feature of this property is the separate cottage, offering complete independence with its own septic system and electric meter. Heated by electric and complemented by a wood-burning fireplace, this charming space includes a bedroom, living room, kitchen, private laundry, and a large deck—perfect for extended family, guests, or potential rental income. Located in the desirable Southeast area, this home offers the perfect balance of tranquility and convenience—just minutes to highways, train, bike paths, shopping, and year-round outdoor activities including fishing, skiing, and hiking. Total Sq footage of 3800 is both the Main House & Cottage - Main House Sq footage is 2,840 Sq Feet & Cottage is 960 Sq Feet

51 - 53 Ivy Hill Road, Brewster

$854,000
4 Beds 3 Baths 933133 MLS
Nestled on a serene and scenic stretch of Gage Road in the town of Southeast, this exceptional 4 bedroom 2.5 bathroom Colonial offers a perfect blend of elegance, comfort, and privacy. The dramatic foyer welcomes you with abundant natural light and gleaming cherry wood floors, setting a warm and inviting tone. A dedicated home office provides a quiet retreat for work and study, while the formal living room, adorned with decorative columns, is currently used as a recreation space. The spacious family room can accommodate even the largest flat-screen TV, perfect for movie night or game days. The chef's kitchen features timeless design, generous counter space, and an adjacent breakfast nook bathed in morning light. The formal dining room, with its ornate ceiling, is perfect for entertaining, and a charming half bath completes the main level. Upstairs, the primary suite is a private sanctuary, offering double doors, a spa-inspired bathroom, and an enviable sized closet. Three additional bedrooms provide ample space for family or guests, accompanied by a pristine hall bath. A 500+ square foot roughed-in bonus room above the garage awaits your personal finishing touches, and the full unfinished basement with high ceilings could add even more versatile space. Outside, a beautiful patio overlooks a wooded backdrop where no future homes can be built behind, ensuring lasting privacy. There is easy access to the nature paths in your ample wooded acreage, perfect for hiking or ATV adventures. Car enthusiasts will appreciate the rare three-bay garage, connected to a combined mudroom/laundry area. Energy efficiency is enhanced by solar panels, while an automatic whole-home generator provides peace of mind during power outages. Although this home offers a sense of seclusion, it is only minutes away from major highways and the Connecticut border, providing the ideal balance of tranquility and convenience. Don't miss the opportunity to make 424 Gage Road your own!

424 Gage Road, Brewster

$850,000
4 Beds 3 Baths 991339 MLS
Welcome to 282-284 Doansburg Road — a rare private country retreat set on 2.5 picturesque acres in the heart of Brewster. Offering approximately 4,000 square feet of combined living space between the main residence and separate guest house, this unique property blends charm, flexibility, and endless possibilities. The main home features spacious living areas filled with natural light, a finished basement ideal for recreation, a home office, gym, or additional entertaining space, and a layout designed for comfortable everyday living. Surrounded by mature trees and peaceful views, the home offers the perfect balance of privacy and warmth. Adding tremendous value and versatility is the separate guest house located above the detached oversized 2-car garage — ideal for extended family, guests, multi-generational living, a private office setup, or potential rental income opportunity. The grounds are truly special, highlighted by a scenic pond that creates a tranquil setting rarely found in today’s market. Whether enjoying quiet mornings overlooking the water, entertaining outdoors, or simply embracing the serenity of nature, this property offers a lifestyle that feels worlds away while remaining conveniently located near major highways, Metro-North, shopping, dining, and schools. A one-of-a-kind opportunity to own a private estate with flexible living options, beautiful natural surroundings, and timeless country charm.

282-284 Doansburg Road, Brewster

$850,000
3 Beds 3 Baths 976350 MLS
Very well-maintained and move-in ready home set on over 1 private acre overlooking natural wooded buffer, offering exceptional privacy in the convenient Springhouse Estates neighborhood. Ideally located close to schools, shopping, and major commuting routes while enjoying a quiet residential setting with minimal local traffic. This home offers more space than it appears, featuring a thoughtfully designed 2-story, approximately 1,800 square foot addition that blends seamlessly with the original structure. The main level of the addition provides approximately 900 square feet of finished living space with access to the rear deck, creating a versatile layout suitable for a variety of living arrangements, work-from-home needs, guest accommodations, or recreation space. The unfinished lower level offers excellent natural light, rear access, and additional potential for future finishing or expanded storage. The original home includes 3 spacious bedrooms, a hall bath, and a primary bedroom bath, complemented by vaulted ceilings, abundant natural light, and a contemporary feel. Numerous updates throughout the home include hydro-air heating and cooling, refinished hardwood flooring, updated stainless appliances, and many additional improvements. The finished lower level adds valuable living space with high ceilings, attractive wood-look luxury vinyl flooring, a full bath with spa tub, dedicated laundry area, and additional storage. This level also includes access to the attached two-car garage with openers, providing both convenience and functionality. Outdoor living is equally impressive with a large rear deck and pergola accessible from both the dining area and the addition, overlooking a private backyard with a recently installed oval above-ground pool. Beautiful landscaping, stone walkways, and retaining walls enhance the property's curb appeal. A standout feature is the approximately 1,100 square foot detached building with 12-foot ceilings and oversized garage doors, currently used as a car enthusiast’s workspace with lift. This flexible space offers many possibilities for hobbies, workshop use, additional vehicle storage, or creative workspace. Additional features include water softener and reverse osmosis systems, expanded electrical panel with generator readiness, and numerous property improvements. A unique opportunity to own a spacious and versatile home in a desirable private setting.

26 Drovers Lane, Brewster

$827,000
3 Beds 4 Baths 864278 MLS
Welcome to 243 Dingle Ridge Road – Private, Peaceful, and Full of Possibility Set on nearly an acre in scenic Southeast, NY, this 3-bedroom, 3.5-bath colonial offers 2,880 sq ft of thoughtfully designed living space with open views overlooking a neighboring horse farm. Here, you get the best of both worlds—low Putnam County taxes and highly regarded North Salem schools. The main level features gleaming hardwood floors and sunlit living and dining spaces, ideal for everyday living and easy entertaining. The Eat-In kitchen boasts stainless steel appliances and ample cabinet space for the home chef. Upstairs, the spacious primary suite includes a private bath, while two additional bedrooms share a full hall bath. The finished, walk-out lower level includes a full bath and offers flexible space for guests, a home office, gym, or playroom. A standout feature is the detached 4-car garage with a large upper level, perfect for storage, a workshop, or future expansion. The home is also equipped with a whole-house generator, providing peace of mind year-round. Enjoy the serenity of upstate living with convenient access to highways, shopping, and Metro-North. Whether you're commuting or working from home, 243 Dingle Ridge Road offers the perfect blend of privacy, flexibility, and convenience.

243 Dingle Ridge Road, Brewster

$820,000
3 Beds 3 Baths 999077 MLS
Welcome Home! This Colonial sits on a quiet culdesac in a highly sought after neighborhood. The flat grounds are well maintained and landscaped. Stone walls align the driveway and the walkway that directs you to the covered front porch. As you step onto the porch, you'll be greeted by glass paned double doors. Inside, hardwood floors flow throughout and natural light fills up the space. The doorways and windows are adorned with decorative moldings and the living room boasts a fireplace. The eat in kitchen features tile flooring with decorative inlays as well as stainless appliances, granite countertops and cherry cabinets. In addition there is a formal dining room and sliders off of the kitchen, which give access to a large deck and a huge backyard that are all perfect for entertaining this summer! Continuing off of the kitchen is the main floor's biggest attraction, the Great Room with vaulted wood paneled ceilings and big picture window. You will also find a half bathroom and a pantry/mudroom with washer/dryer hookup on this floor. The primary ensuite is located upstairs and it has ample closet space and tasteful bathroom design. There are two other bedrooms, an office and a second full bathroom, also on this level. The walkout basement lends home to a very clean mechanical space. Schedule a showing today! This one won't be on the market long.

18 Bradley Court, Brewster

$815,000
3 Beds 3 Baths 887672 MLS
Completely Updated Sprawling Ranch offering 3,600 Sq Ft of Refined Living Space, ideal for extended family living! Welcome to this beautifully updated 3,600 square-foot ranch-style home, nestled on a tranquil cul-de-sac and set on a private, one-acre lot. Blending modern luxury with classic comfort, this expansive residence offers exceptional living space, both inside and out. The main level features a state-of-the-art kitchen outfitted with premium appliances, sleek countertops, and custom cabinetry—perfect for everyday living and entertaining. Adjacent is a formal dining room and a spacious living room, creating a seamless flow for hosting guests. A large family room with a cozy gas fireplace offers the perfect spot to unwind, while a dedicated den/office adds flexible space for work or study. The primary suite is a true retreat, complete with a walk-in closet and a beautifully updated ensuite bathroom. Two additional generously sized bedrooms share a fully renovated hall bathroom, ensuring space and comfort for family and guests alike. The lower level offers incredible versatility, ideal for extended family living or multi-generational use. It includes a second family room, a full bath, a den, and an additional office area—all bathed in natural light through large windows and featuring direct walk-out access to the backyard. Additional highlights include central air conditioning, a two-car garage, and wonderful outdoor living spaces including two decks and a large patio—perfect for entertaining or enjoying quiet moments in your serene, tree-lined backyard. This move-in ready gem offers privacy, space, and modern convenience, all in a highly desirable location. ONLY 1.3 Miles to Brewster Train Station and Mins to I-684 or I-84 making this home IDEAL for commuters! Don't hesitate, this Gem will not last!

9 Carol Court, Brewster

$810,000
4 Beds 3 Baths 920750 MLS
Stunning Georgian Colonial on Nearly 3 Acres – A Perfect Blend of Elegance, Comfort, and Privacy!!! Welcome to this breathtaking 4-bedroom, 3-bath Georgian-style Colonial, gracefully set on nearly 3 acres of lush, park-like grounds. This exceptional home offers the perfect balance of timeless sophistication and modern comfort—ideal for both everyday living and unforgettable entertaining. From the moment you enter, you’re welcomed by soaring cathedral ceilings in the foyer and family room, creating a grand yet inviting ambiance. The open-concept layout seamlessly connects the living, dining, and kitchen areas, making it easy to host gatherings or enjoy quiet moments with loved ones. The formal dining room is perfect for holiday celebrations, while the cozy living room and den offer peaceful retreats for reading, relaxing, or game nights. At the heart of the home is a sunlit, spacious kitchen designed to inspire—featuring abundant counter space, a large pantry, and a layout that’s as functional as it is beautiful. The family room, with its dramatic ceilings and charming wood stove, is a warm and welcoming space where memories are made—whether you're curling up by the fire on a chilly evening or entertaining guests year-round. Upstairs, the luxurious primary suite is your private sanctuary, complete with a full bath, sitting room, and three walk-in closets. Three additional generously sized bedrooms and gleaming hardwood floors throughout provide comfort and flexibility for family and guests alike. The walkout basement opens to a serene backyard oasis—perfect for summer BBQs, family gatherings, or simply enjoying the peace and beauty of nature. Whether you're entertaining a crowd or savoring a quiet morning coffee, this home offers the best of both worlds. With a dedicated home office for remote work and a versatile den for play or relaxation, there’s space for every lifestyle need. This is more than just a house—it’s a place to call home, where every detail has been thoughtfully designed for comfort, connection, and joy. Come experience the warmth, privacy, and elegance of this extraordinary property. Your dream home awaits!

499 Farm To Market Road, Brewster

$800,000
3 Beds 3 Baths 967020 MLS
If you're looking for your dream Modern Farmhouse, this is it. No expense was spared in this completely renovated home, and every detail reflects the highest quality and taste. Three bedrooms with a fourth bonus room that can be converted to fit your lifestyle. En Suite Master bath. Hard wood flooring throughout. The gourmet kitchen includes Quartz counters and stainless appliances. Once you move in, you will never have to worry about unexpected maintenance as there is 100 year metal roofing, 30 year smart siding, high efficiency propane heat and water heat, Central A/C, and completely new electric, plumbing, and HVAC. Situated on almost 3/4 of an acre of land with privacy but deceivingly close to the Metro North, Highways 684 and 84, and all the shopping and dining the area has to offer.

127 Brewster Hill Road, Brewster

$790,000
4 Beds 3 Baths 991526 MLS
Welcome Home to this charming and spacious 4-bedroom, 2.5-bath Tudor-style Colonial, perfectly set on a private, level 1.33-acre property designed for both everyday living and effortless entertaining. A warm and inviting entry with hardwood floors leads into a bright formal living room, while the extra-large dining room offers the perfect setting for gatherings, highlighted by a stunning double-sided wood-burning fireplace that adds character and charm. The heart of the home is the well-appointed kitchen, featuring granite countertops, stainless steel appliances, a double wall oven, electric cooktop, and tile flooring—all open to a comfortable family room with a fireplace, creating a seamless flow for modern living. An updated powder room and a spacious laundry/mudroom with sink—perfect for busy households—are conveniently located just off the kitchen and adjacent to the oversized two-car garage. Step outside to a spacious Trex deck overlooking the beautifully level and private backyard, complete with a pergola for shade—ideal for outdoor dining and relaxing. A set of steps leads down to a patio with a fire pit area, perfect for entertaining or enjoying quiet evenings. Upstairs, you’ll find three well-appointed bedrooms, including two with walk-in closets, along with an updated hall bath featuring a sleek stand-up shower. The expansive primary suite offers a walk-in closet, additional linen storage, and a private bath with double vanity and whirlpool tub, along with a separate room housing the shower and toilet for added privacy. Additional highlights include a large unfinished basement providing ample storage, a whole-home Breeze airflow system, new hot water heater, new well holding tank, and a new water softener system. Conveniently located to highways, train, shops, schools, bike path, skiing, hiking, and more, this home offers the perfect blend of classic charm, thoughtful updates, and comfortable living—don’t miss the opportunity to make it yours!

130 Cobb Road, Brewster

$789,900
4 Beds 6 Baths 913217 MLS
Welcome to this custom-built front porch Colonial, designed and built by its master builder owner with quality and care throughout. This distinctive home offers more than 4,100 sq. ft. in total, including approximately 3,200 sq. ft. of living space on the first and second floors, 952 sq. ft. of finished space on the lower level, and a walk-up attic of nearly 1,000 sq. ft. that offers excellent expansion potential. The second floor features two primary bedroom suites, two additional bedrooms, and a hall bath. A total of 4 bedrooms and 3 full baths. The additional primary suite not only includes a full bathroom and laundry but also its own dedicated staircase to the first floor with a separate rear entry—making it ideal for flexible use. In total, the home offers 4 bedrooms and 6 baths (3 full, 3 half). On the main floor, the spacious eat-in kitchen opens to the living room with fireplace and connects to the formal dining room, creating an inviting flow for daily living and entertaining. There's a large pantry off the kitchen, two lavatory bathrooms and a separate study/office space. A two-story center hall foyer, custom wall moldings, and detailed trim work add elegance and character throughout. On the lower level, you’ll find a recreation room with walk-out access to its own private patio, finished storage, a half bath, laundry, and utility room. This area also has a separate entrance accessible by a pathway along the side of the house, offering privacy and convenience. The layout lends itself beautifully to extended family or multi-generational living. Outdoor living spaces include multiple patios, spacious decking, and landscaped stone walls that frame the home, all set on 2.44 wooded acres at the end of a quiet cul-de-sac. Situated in the Big Elm subdivision, the home provides a private setting while still only 1 mile from US Route 22 for shopping and commuting, and less than 3 miles to Brewster Schools. A rare opportunity to own a custom residence built with craftsmanship and care.

26 Bradley Drive, Brewster

$787,500
5 Beds 5 Baths 874841 MLS
Two homes for the price of one! Rare opportunity to own a large main Home (3 BDR / 2.5 BATH) and a separate Cottage (2 BDR / 2 BATH) on over 3 + private acres AND a free-standing separate garage. Perfect for a family compound, "live in one, rent the other" or use the 912 sqft Cottage as an artist studio/workspace. The Cottage has a strong rental history. Each home has its own Well, Septic, and 200-amp service. Recent upgrades include new roofs (under 3 yrs), Solar Panels, updated bathrooms, oak floors, vaulted ceilings, and wood-burning stoves in both homes. Both homes feature filtration/UV water systems, new appliances, and new electric. A detached 2.5 cargarage sits separately on the property with its own defined space—ideal for storage, a workshop, or conversion. Heating is floor furnace and electric baseboards. Very efficient home-Solar Panels and Woodburning stoves. Propane tank is above ground. Newly built patio with approved plans for a beautiful Timber Canopy (see image in photos). The fully approved plan included the use of timber from the property. Current Tenant in the 2-bedroom Cottage pays $2,800 per month plus utilities and is month to month. It is possible, with town approval to subdivide the Cottage onto its own parcel since it is in R40 zoning. Enjoy the best of both worlds, private homes in a beautiful setting (surrounded by DEC greenspace) yet an ideal commuter location with close proximity to the train, I-84, as well as local eateries, shopping centers and much more. Overall floor plan is attached under public documents; additional floor plans are available upon request. Split units AC/Heat in Cottage only.

1302 Route 22 Unit #1300, Brewster

$785,000
4 Beds 3 Baths 986113 MLS
Welcome to this beautifully appointed Colonial, meticulously maintained by its original owners and highlighted by a charming rocking chair covered porch. Nestled behind a natural stone wall and set back on a quiet street, this home sits on nearly an acre of land, offering both privacy and timeless curb appeal. A light-filled, freshly painted foyer featuring gleaming hardwood floors and a sparkling chandelier sets the tone for the thoughtfully designed interior. Natural light flows throughout the main level, where living spaces are perfectly suited for both entertaining and everyday comfort. The sun-drenched living room showcases large windows, polished hardwood floors, and elegant French doors leading to the formal dining room. Here, decorative molding, rich hardwood flooring, and multiple windows create a refined setting for gatherings and celebrations. The eat-in kitchen offers ample counter space, a center island, and sliding glass doors that open to the manicured backyard—perfect for morning coffee, casual meals, or late-night bites. The kitchen flows seamlessly into the inviting family room, featuring a beautifully appointed wood-burning fireplace framed by custom built-in shelving, hardwood floors, and an oversized window. This warm and welcoming space is ideal for relaxing or entertaining year-round. Step outside to enjoy easy access to the deck and paved patio—perfect for outdoor dining and summer barbecues. A well-placed laundry room and direct access to the two-car garage add everyday convenience and complete the main level. Upstairs, the primary suite serves as a serene retreat, complete with hardwood flooring, recessed lighting, a spacious walk-in closet, and a private bath. Three additional bedrooms and a full hall bath provide flexibility for extended living, guests, or home office needs. An unfinished bonus area on the upper level, along with a spacious walkout basement, offers incredible potential for future expansion—ideal for a home office, recreation room, gym, or media space. Additional amenities include a new roof, hardwood floors throughout, main level office or den, pantry, private laundry room, powder room, and storage shed. Ideally located in a peaceful setting just 75 minutes from New York City, this home offers convenient access to Metro-North, Routes 22, 684, and 84, as well as nearby attractions including Thunder Ridge Ski Area, local shopping, dining, and the scenic beauty of the Hudson Valley. Don’t miss this exceptional opportunity to own a home that perfectly blends comfort, style, and location.

8 Rose Lane, Brewster

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