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Brewster, New York Homes for Sale

Brewster is a village within the town of Southeast in Putnam County, New York, approximately 50 miles north of New York City. Brewster is the most densely populated portion of the town. The village is named after two early farmer landowners, Walter and James Brewster.

Brewster, founded in 1894, and known as the “Hub of the Harlem Valley” is located on the eastern edge of Putnam County, just above the Westchester County line and situated within a ½ square mile area, home to a Metro North commuter station, a Brewster Elementary school, various faith based institutions, commercial establishments, restaurants, a museum and library enjoyed by approximately 2,162 residents in 881 households. A historic community about an hour north of New York City, the Village of Brewster is in the midst of a dramatic renaissance. New water and sewer lines, artful renovations of classic homes and building, pedestrian friendly streets and a scenic setting will make Brewster a vital 21st century Business and cultural destination. Within five minutes can you walk to a fine library, a fast commuter train and a world-class trout stream. To fully utilize Brewster’s rich future, residents must make the most of a unique blend of rural and modern assets. With accessible, small-town government and strong community spirit, the village embraces its role as an environmental steward f the Croton Reservoir System. Simultaneously, citizen groups carefully evaluate and integrate state-of-the-art communication and transportation systems to ensure Brewster’s long-term role as the economic hub of the entire Harlem Valley.

The mission of the Brewster Central School District is to provide an environment in which all children will learn just like any other school. The school district includes one high school, one middle school, one intermediate school (grades 4-5) and two elementary schools; Brewster High School, Henry H. Wells Middle School, C.V. Starr Intermediate School, John F. Kennedy Elementary School and Garden Street Elementary School. The organizational structure will possess the resources and personnel to establish high standards of achievement, to foster respect and dignity for each individual, to offer varied learning opportunities, and to equip all students with the skills necessary to become productive, contributing members of the world community. Brewster schools are very good and achieve many things. 

Village of Brewster: http:/www.brewestervillage-ny.gov
Brewster Central School District: http://www.brewesterschools.org

Brewster Homes for Sale

$14,900,000
938337 MLS
Discover an extraordinary 320+ acre legacy property in Putnam County — a former summer camp steeped in history and now poised for its next chapter with absolute privacy and limitless potential. Spanning 8 separate tax lots, the offering includes nearly 50 acres of commercially zoned land across 3 parcels and approximately 270 acres of residentially zoned land across the remaining 5. The crown jewel is the 95.63-acre flagship parcel, entered from Ballyhack Road, where a pristine 20-acre private lake with a newly updated dam and semi-developed waterfront awaits. Miles of established trails wind through the property, passing dozens of the original camp structures that still stand in various stages of disrepair— a lakefront lodge, large dining halls, recreation and education buildings, dormitories, medical facilities, and even an inground pool — all evoking a bygone era while inviting imaginative reuse or redevelopment. A brand-new, never-used $7 million state-of-the-art sewage treatment plant capable of servicing 60-65 homes sits ready on site, complete with current SPDES permit, full generator, and 100% redundant backup system. An additional entrance can be reclaimed from Old Route 22 via one of the commercial parcels, offering outstanding accessibility and development flexibility. Beyond the private lake, the land is enriched by two tributaries of the East Branch Croton River and approximately 1,640 feet of direct frontage on the river itself — a renowned stretch for kayaking and canoeing within the pristine Great Swamp watershed. At the Ballyhack entrance, a charming 3-bedroom ranch home serves as the ideal caretaker’s residence or gatehouse. Rolling topography, mature woodlands, and dramatic elevations create a landscape that feels worlds away, yet the property remains remarkably convenient to major highways and Metro North train stations for easy access to and from NYC. Surrounded by nature's embrace, every acre beckons for recreation and adventure, defining the perfect escape for those seeking solitude, sport, and serenity. The possibilities for development and use are vast with the permitted and special uses available with this multi-zoned, multiple-parcel property. A sample of permitted uses in C1 zoning include: research and development, veterinary hospitals, greenhouses and nurseries, restaurants, health or fitness clubs, recreational sports facilities, business and professional offices, banks, drive-in and fast food establishments. A sample of special uses include: light manufacturing, retail centers, warehouses, conference and cultural centers, membership club, nursery schools and day care centers. Rarely does a canvas of this scale, privacy, natural beauty, and built-in modern utilities come available. This is more than land — it’s a once-in-a-generation opportunity to shape something truly remarkable.

111 Ballyhack Road, Brewster
$4,250,000
1008903 MLS
Excellent Main Street location, only one mile from I-684/84. This is a 3-story professional building with elevator and 80-car parking lot. 3 entrances. 90% occupied.

155 Main Street, Brewster
$2,795,000
4 Beds ⋅ 7 Baths ⋅ 947922 MLS
Sunny Ridge. Brewster’s most extraordinary offering. Set behind iron gates up a long winding drive, this estate will thrill you. Perched on a peaceful cul-de-sac street in a highly sought-after location on the Southeast/North Salem border - just 60 miles from NYC and 4 miles to the Metro North train station. Set on over 15 acres with commanding panoramic views and a profound sense of privacy - your closest neighbors are the horses at the abutting farm. The 8,000+ sq. ft main residence offers a level of craftsmanship that simply doesn’t exist at this price point. As you step inside the entry foyer, the exquisite architectural details are immediately apparent - custom millwork, detailed moldings, elegant archways, tray ceilings, and gleaming hardwood floors. The focal point is an incredible floating staircase - providing access to three magnificent levels of luxury living. There is a formal living room with soaring 20+ foot ceilings, six fireplaces, a massive fully equipped chef’s kitchen, a fully finished 2200+ sq. ft lower level with custom wet bar, movie theater, gym, wine cellar, and two french door walkouts to covered patios. Multiple offices for working from home. Cozy den with french doors out to wrap-around mahogany deck, covered porch, and outdoor kitchen with patio. Gorgeous formal dining room - ideal for dinner parties and entertaining. Upstairs, there is an expansive primary bedroom suite with sitting area, balcony, spa-like bath, and dual walk in closets. Down the hall, there are three additional en-suite bedrooms with walk-in closets and a laundry room. There is an attached heated 4 car garage, as well as a custom-built 4,000 sq.ft carriage barn, which provides garage space for an additional 12 cars. The carriage barn also offers a world of possibilities as a guest house, art/music studio, and more. Sunny Ridge is a rare and compelling opportunity for the discerning buyer seeking a private, resort-caliber estate within easy reach of Manhattan.

16 Reynwood Drive, Brewster
$1,950,000
5 Beds ⋅ 7 Baths ⋅ 1029717 MLS
Magnificent Stone & Stucco Tudor Estate nestled on 2 professionally landscaped, manicured acres in Brewster’s historic Milltown area, this custom-built 7,400 sq. ft. Tudor estate effortlessly blends grand elegance with cutting-edge modern luxury. From the moment you step into the soaring 2-story marble and granite foyer, the home’s exceptional craftsmanship is on display. The main level features a sweeping open floor plan anchored by 10’ to 14’ ceilings, gorgeous hardwood floors with custom inlays, and floor-to-ceiling bay windows that frame views of your private backyard oasis. The family room serves as a stunning centerpiece with its 14’ tray ceiling, Sonos-powered audio system, and a magnificent wood-paneled marble fireplace. For the culinary enthusiast, the gourmet eat-in kitchen boasts high-end appliances, bespoke handmade cherry cabinetry, two island preparation areas, and dual dishwashers. Conveniently located nearby is a dedicated, separate laundry room with integrated pantry storage for ultimate organization. An Unparalleled Main-Level Primary Wing Retreat to the expanded master suite, a completely private sanctuary redesigned for ultimate modern living. This sprawling wing features its own dedicated sitting room and a rare, highly desired "his and hers" dual office setup, providing two entirely separate, quiet workspaces for remote professionals. The suite's multiple walk-in closets have been entirely reimagined with premium California Closets systems, offering impeccable custom organization. The retreat is completed by opulent his-and-her master baths. To ensure absolute comfort for everyone, every additional bedroom in this estate also features its own dedicated full bath and walk-in closet. Premium Amenities & Smart Home Technology Entertainment & Audio: Enjoy a cinematic experience at home with a state-of-the-art 4K Home Theater featuring a massive 120-inch screen. Immersive sound follows you throughout the entire estate via a multi-room Sonos audio system. Connectivity: Stay seamlessly connected with high-speed network Ethernet ports and modern USB outlets strategically installed throughout the home. Smart Climate & Wellness: Stay perfectly comfortable with an integrated Smart Home AC/Heat setup managing the premium Hydro-Air climate control system. Drink with confidence knowing the property is outfitted with a whole-house water filtration system. Elite Home Gym: The dedicated full exercise room is a fitness enthusiast's dream, fully equipped with premium Peloton and Tonal smart training systems. Entertainer’s Backyard: Step out onto expansive patios leading to a heated, in-ground saltwater pool, all secured within a beautifully fenced 2-acre lot with mature trees and shrubs. Lower Level Living: The full, walk-out finished basement also hosts a legal accessory apartment equipped with 1 bedroom, a great room, a full kitchen, a dining area, and finished storage—perfect for extended family or guests. Parking & Mechanicals: Car enthusiasts will love the two heated attached garages accommodating up to 5 vehicles. Located in the desirable Brewster School District (John F. Kennedy Elementary) with an easy commute , this single-family masterpiece offers an unparalleled lifestyle.

8 Bridey Lane, Brewster
$1,800,000
4 Beds ⋅ 4 Baths ⋅ 1027367 MLS
This exceptional new construction showcases elegant Southern Colonial architecture paired with refined, modern luxury, offering approximately 5,348 square feet of thoughtfully designed living space in a coveted end-of-cul-de-sac setting. Currently in the early stages of construction with framing underway, the home features a gracious blend of formal and informal living areas, highlighted by 9-foot ceilings and 7-foot doors on the main level that flow seamlessly into a gourmet’s kitchen with an expansive center island, premium appliances, a walk-in pantry, and a fully appointed butler’s pantry. The upper level offers bright, generously scaled rooms with eight-foot ceilings, including four bedrooms with walk-in closets, one with an ensuite bath, two sharing a Jack-and-Jill bath, and an impressive primary suite designed as a private retreat with a spa-inspired bathroom featuring a glass-enclosed wet room with soaking tub and shower. A main laundry room on the upper level is complemented by an additional laundry area near the mudroom on the main floor for added convenience. Set on 3 acres, the property provides ample space to create a private outdoor oasis with room for a pool and additional amenities, while the unfinished walk-out basement offers exceptional potential for future customization. The builder’s interior designer has finalized a premier selection of finishes, ensuring a harmonious blend of classic architecture and modern luxury. This is a rare opportunity to acquire a brand-new, professionally styled estate in a private cul-de-sac setting.

31 Tea House Lane, Brewster
$1,500,000
920256 MLS
321 Guinea Road in the Town of Southeast presents a rare opportunity with flexible RC (Rural Commercial) zoning that permits a range of uses including retail, offices, restaurants, and light commercial operations. The property also offers potential subdivision opportunities with approvals and variances, adding further development value. At the same time, its rural setting makes it equally attractive as a private estate or equestrian retreat (with conditional approval), with ample acreage suitable for custom homes, paddocks, or stables. Conveniently located near I-84 and I-684, this property is well positioned for both commercial users and developers seeking to serve the Hudson Valley, Westchester, and Connecticut markets, while also offering the charm and possibilities of estate living. This parcel is part of the Reed Road assemblage and can be purchased individually or together with neighboring properties for a package of up to 232 acres.

321 Guinea Road Avenue, Brewster
$1,200,000
4 Beds ⋅ 4 Baths ⋅ 1025029 MLS
Stunning Home in Fortune Ridge. Welcome to this exceptional 4 bedroom 2 Full and 2 half bath custom-built home in the highly sought-after Fortune Ridge community. Built in 2022 and offering approximately 3,350 square feet of impeccably designed living space, this pristine residence showcases a sleek, modern aesthetic complemented by premium upgrades and designer finishes throughout. The heart of the home is the expansive chef’s kitchen, featuring high-end appliances, a large center island, abundant cabinetry, and the perfect layout for both everyday living and entertaining. The kitchen flows seamlessly into the oversized family room, where beautiful windows flood the space with natural light and a stunning fireplace creates a warm and inviting atmosphere. The main level also offers a versatile formal dining room, currently utilized as a home office, as well as a comfortable living room. A convenient laundry room and mudroom are located just off the attached two-car garage. Upstairs, the luxurious primary suite serves as a private retreat, complete with two spacious walk-in closets and a spa-inspired bath featuring a soaking tub and upscale finishes. Three additional generously sized bedrooms and a well-appointed hall bath complete the second floor. The living space continues in the finished lower level, offering incredible flexibility for recreation and relaxation. Complete with a half bathroom and sliding doors to the backyard, this expansive area is currently configured as a golf simulator and is ideal as a family room, game room, fitness area, or guest space. Step outside to your own private oasis and one of the most desirable lots in the neighborhood. The fully fenced backyard has been thoughtfully designed and professionally landscaped with stunning hardscape patios, retaining walls, and an expanded deck, creating the perfect setting for outdoor entertaining and peaceful evenings at home. Residents of Fortune Ridge enjoy outstanding community amenities, including a clubhouse with fitness center, playroom, gathering hall and kitchen for private events, swimming pool, tennis courts, basketball court, and playground. Ideally located just minutes from the Westchester border, I-684, and only 2.3 miles from the train station, this home offers the perfect combination of luxury, convenience, and lifestyle. This stunning home in one of the area's premier neighborhoods is truly move-in ready and won't last long!

17 Stableview Lane, Brewster
$1,100,000
4 Beds ⋅ 3 Baths ⋅ 1030639 MLS
From the moment you arrive, this meticulously maintained 4-bedroom, 3.5-bath Colonial welcomes you with timeless curb appeal and the promise of effortless living. Perfectly positioned on a desirable corner lot, this move-in ready home has been thoughtfully updated to blend classic elegance with today's modern conveniences. Step inside to discover warm hardwood floors, a cozy fireplace, custom blinds, and a functional mudroom designed for everyday living. Expansive living spaces are complemented by quality finishes throughout, while stunning sunset views provide the perfect backdrop to unwind at the end of the day. The spacious primary suite serves as a private retreat, featuring a spa-inspired bath complete with a soaking tub, separate shower, water closet, and dual walk-in closets designed for exceptional storage and organization. Every improvement has been made with comfort and peace of mind in mind. A new HVAC system was installed in 2025, while 2020 brought an impressive list of upgrades, including new appliances, California Closets in every bedroom, a Generac generator with a transfer switch, an underground propane tank, an expansive deck and patio, and a built-in fire pit—creating the ideal setting for entertaining or enjoying quiet evenings under the stars. Beautifully cared for and thoughtfully enhanced, this exceptional home offers the perfect balance of style, functionality, and reliability in a highly desirable location. Simply move in, settle in, and begin making memories in a home that's ready to be enjoyed from day one!

8 Shailin Lane, Brewster
$1,100,000
10 Beds ⋅ 6 Baths ⋅ 958315 MLS
Set on five private, wooded acres in one of Putnam County’s most desirable locations, this exceptional 21-room estate offers rare privacy, scale, and architectural significance. Originally built in 1928 and featured in House Beautiful, the home was designed by Ilonka Karasz, renowned artist and co-founder of MoMA. After serving as a wellness retreat, the property has been thoughtfully restored to a stunning single-family residence. A grand foyer opens to a dramatic vaulted living area anchored by a striking fireplace and sliding doors to a garden terrace. The dining area flows seamlessly into a sunlit wet bar and a newly renovated, lofted chef’s kitchen with high-end stainless steel appliances, oversized windows, and a statement granite island. A winding hallway leads to ten renovated bedrooms, five with en-suite baths. A lofted library with a fireplace connects the bedroom wings, while an additional living room or study opens through Andersen doors to a private rear terrace. A winding staircase leads to a beautifully renovated studio with panoramic views and its own terrace. Additional spaces include a billiards and poker room, fitness center, wine cellar, and attached two-car garage. Outdoor amenities feature a 35-foot swimming pool, a tranquil pond, and a covered carport creating a true estate setting with exceptional versatility. With its scale, layout, and prior use, the property offers outstanding flexibility for a variety of lifestyle or income-producing opportunities, including a boutique bed-and-breakfast, luxury short-term rental, wellness or retreat center, private event venue, or multigenerational compound, subject to approvals.

584 Milltown Road, Brewster
$1,010,500
4 Beds ⋅ 5 Baths ⋅ 1010711 MLS
Nestled on 2.84 private, professionally landscaped acres, this impressive 4-bedroom, 4.5-bath Colonial offers over 3300 square feet of beautifully designed living space plus 1090 feet of mostly finished basement. A grand entry welcomes you into a thoughtfully designed floor plan featuring spacious formal and casual living areas, two fireplaces, and abundant natural light throughout. The gourmet kitchen serves as the heart of the home, seamlessly connecting to the dining and entertaining spaces. The expansive primary first floor bedroom suite provides a private retreat with generous closet space and a luxurious bath. Additional highlights include central air, a full basement, and an attached two-car garage. Enjoy the perfect balance of privacy and convenience in a sought-after Brewster location, just minutes from shopping, dining, schools, and major commuter routes. A truly exceptional property offering space, comfort, and timeless appeal.

141 Gage Road, Brewster
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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.