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$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
$999,000
5 Beds ⋅ 5 Baths ⋅ 1024061 MLS
Exquisitely designed and beautifully appointed, this exceptional Colonial in the highly sought-after Windsor Woods neighborhood masterfully blends timeless elegance with modern luxury. Lovingly maintained by its original owners, the home is perfectly sited on beautifully manicured grounds offering both privacy and outstanding curb appeal. A light-filled foyer welcomes you with soaring ceilings, gleaming hardwood floors, and a sparkling chandelier, setting the tone for the refined craftsmanship and impeccable décor found throughout the home. Natural light graces every room, creating an inviting atmosphere where sophisticated entertaining and everyday living come together effortlessly. The elegant formal dining room provides a gracious space for hosting guests. Enhanced by expansive windows, rich hardwood flooring, and detailed decorative molding, it creates the perfect backdrop for intimate dinners and celebrations. At the heart of the home is an open-concept kitchen and family room thoughtfully crafted for today's lifestyle. The chef-inspired kitchen is beautifully appointed with gleaming white cabinetry, granite countertops, updated appliances, a professional six-burner gas cooktop, an oversized center island, built-in coffee bar, spice drawer, generous pantry, and exceptional storage. Whether enjoying your morning coffee, preparing meals, or gathering for casual conversations, this space effortlessly becomes the center of daily life. The kitchen flows seamlessly into the warm and inviting family room, where a lovely wood-burning fireplace, oversized windows, and rich hardwood flooring create a welcoming ambiance for relaxing evenings or entertaining year-round. Sliding doors open onto a private deck overlooking landscaped grounds featuring an in-ground sprinkler system, tasteful outdoor lighting, and a storage shed, creating an equally inviting outdoor retreat. Completing the main level is an aesthetically pleasing home office with French doors, hardwood flooring, and abundant natural light, offering a quiet and inspiring workspace. A stylish powder room, thoughtfully positioned laundry room, and convenient access to the oversized three-car garage complete this exceptionally functional level. Upstairs, an attractive bonus room with high ceiling, abundant natural light, and French doors provides remarkable versatility as a media room, playroom, or craft room. Just beyond, the luxurious primary suite serves as a private sanctuary, featuring tranquil mountain views, custom walk-in closets, and a spa-inspired bath complete with dual vanities, a soaking tub, and a glass-enclosed shower. Three generously sized additional bedrooms and a nicely appointed full bath provide comfortable accommodations for all. The walk-out lower level offers exceptional flexibility with two thoughtfully designed living spaces. A fully legal one-bedroom accessory apartment features its own private entrance, full kitchen with living area, bedroom, full bath with glass-enclosed shower, and private laundry, making it ideal for multi-generational living, guests, an au pair, or rental income. Separate from the apartment is additional finished living space featuring a comfortable den, recreation area, full bath with a large walk-in tiled glass shower, and generous storage. Designed for today's lifestyle, this meticulously maintained home also offers numerous thoughtful upgrades, including smart thermostats, high-efficiency furnaces, a tankless water heater, a water softening system providing enhanced comfort, efficiency, and peace of mind. Ideally located in a peaceful yet convenient setting just 75 minutes from New York City, this remarkable home offers easy access to Metro-North, Routes 22, I-684, and I-84, while being moments from Thunder Ridge Ski Area, shopping, dining, and the countless recreational opportunities and natural beauty that define the Hudson Valley. A home of luxury, comfort, and timeless sophistication.

128 Apple Hill Road, Brewster
$250,000
2 Beds ⋅ 1 Baths ⋅ 1020553 MLS
Rustic cabin with private dock located on a small private lake. Enjoy peace and tranquility from your deck while you take in the best nature has to offer in this 2 bedroom cabin with direct waterfront access. This property is a private co-op owning 110 acres in Putnam County with a large lake surrounded by 28 cabins concealed from the lake by trees and plantings. Shareholders hold leases to their cabins. The lake is motor-free and offers swimming, fishing and (non-motor) boating. The cabin is seasonal since the community water is turned off from approximately the middle of October until the middle of April thus making it the perfect three-season get away. The community is careful to preserve the quiet and historic nature of this special place. The cabins were built starting in the 1920’s and the ability to make changes to their exterior, size, structure and concealment is greatly restricted in order to preserve their rustic character. Likewise, the community considers itself the steward of the lake and the surrounding wooded landscape. Financing is not permitted. Final sale is dependent upon co-op Board approval of prospective buyers. Please note there is no toilet in the cabin, only an outhouse.

00 Fairfield Drive Unit #25, Brewster
$675,000
3 Beds ⋅ 4 Baths ⋅ 1012324 MLS
Welcome home to 136 Foggintown Road! The moment you turn down that winding driveway you just know. Set on over two gorgeous private acres in Brewster, this charming 3 bedroom 4 bathroom Cape Cod has so much to offer. The kitchen has been nicely updated with navy and white cabinetry, granite countertops, stainless steel appliances, shiplap walls. The main level offers living room with fireplace, and dining room that leads into the kitchen. As well as, a primary bedroom with full bathroom, a second bedroom and a dedicated office space giving you everything you need all on one floor. The upper level has one bedroom plus bonus space perfect for a playroom, TV room or whatever suits your needs. The finished lower level with its own separate rooms gives everyone the space and privacy they need making this home a rare find for those looking for flexible living arrangements under one roof. Outside you will enjoy the mature landscaping, charming garden and deck. Minutes to Metro North, Route 22 and I-684. Brewster Central School District.

136 Foggintown Road, Brewster
$409,900
2 Beds ⋅ 2 Baths ⋅ 1018224 MLS
Welcome to Putnam Lake! This charming updated Cape sits on a Rare 0.42-acre corner lot in a quiet, established neighborhood with Putnam Lake rights! Officially a 2 bedroom 1.5 - bath home, this property features two additional flex rooms perfect for guests, a home office or hobby space. Thoughtful built-in cabinetry, desk space and abundant storage to maximize every square foot. This home includes updates such as: Bosch high-efficiency heat pump with central air (2021), new oil furnace (2021), new half bath (2026), professionally serviced water heater (2026), water filtration system, water softener and well tank (2018), septic pump replacement (2022) with septic serviced (2026), New washer (2024) New Dryer (2022), new gutters and downspouts (2021), New Decking (2026) and vinyl replacement windows with sun blocking coating for improved energy efficiency . Additional highlights include: propane range, pellet stove insert with the option to restore a wood-burning fireplace, bamboo flooring on the main level, hardwood flooring upstairs, attic exhaust fan, generator hookup with dedicated transfer panel, Verizon FIOS, NYSEG electric and a detached shed/workshop. The partially fenced yard offers plenty of room for entertaining, gardening, pets or play. Included with ownership are Putnam Lake rights, offering swimming, fishing, boating and beach access just two blocks away, with the public beach approximately 1/2 mile away from the home. This home is also conveniently located just 10 minutes to I-84 and I-684, 12 minutes to the Southeast Metro North Station and 15 minutes to the Danbury Fair Mall. Move-in ready with modern mechanical updates, exceptional storage, flexible living space and a rare combination of a large lot and lake rights- This is Putnam Lake living at its BEST.

21 Cameron Road, 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
$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

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.