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$479,000
2 Beds ⋅ 2 Baths ⋅ 941610 MLS
End-unit tri-level townhouse tucked away on a quiet cul-de-sac in the highly sought-after Reed Farm community. As the last townhouse in the development, this desirable Upper Jonathan model enjoys added privacy, extra green space, and sweeping long-range views from its elevated setting. Offering approximately 1,610 square feet of living space across three levels, the home features two bedrooms and two bathrooms, boasting an open, airy layout filled with natural light.The renovated kitchen showcases new quartz countertops, stainless steel appliances, and refinished cabinetry. Vaulted ceilings, a cozy fireplace, and sliding glass doors enhance the inviting main living area and open to a private deck overlooking the scenic landscape. The main-level primary suite includes a generously sized updated bathroom and an adjacent flexible room perfect for a home office, sitting area, or nursery. An inviting loft level overlooks the dramatic living space below and features a spacious bedroom area along with an additional lounge or flex space ideal for guests, reading, or a work-from-home setup. The lower level offers approximately 600 square feet of finished storage space, including a large recreation room, laundry area, and multiple storage closets. Reed Farm’s beautifully maintained grounds offer residents access to a clubhouse, swimming pool, tennis and basketball courts, and a playground. Ideally located near orchards, Metro-North, and major commuter routes, this home offers the perfect blend of comfort, convenience, privacy, and community living.

806 Orchard Hill Lane, Brewster
$349,900
2 Beds ⋅ 1 Baths ⋅ 1048316 MLS
Welcome to this beautifully renovated 2-bedroom, 1-bath cottage on a quiet street, conveniently located minutes from shopping, schools, and the community beach. Renovated in about 2021, this charming home features hardwood floors, recessed LED lighting, and an updated kitchen with newer countertops, island, and stainless-steel appliances. The renovated bathroom adds a stylish touch, while updated windows, vinyl siding, roof, and septic provide peace of mind. With minimal steps to the entrance, the home offers easy access, while the fully fenced backyard provides a great space for your pup to enjoy. Relax on the front deck or covered rear porch. A large shed provides plenty of additional storage, and the asphalt driveway completes the package. A wonderful opportunity to enjoy a comfortable, updated home in a convenient location!

3 Preston Place, Patterson
$594,769
3 Beds ⋅ 2 Baths ⋅ 1047465 MLS
Great commuter location! This charming 3-bedroom, 2-bath Ranch is situated in a desirable neighborhood and offers comfortable living with plenty of flexible space. The main level welcomes you into a spacious living room with beautiful hardwood floors. A hallway leads to three bedrooms and a full hall bathroom. The eat-in kitchen features a convenient door to the breezeway, which connects to the one-car garage, as well as a sliding glass door leading to a newer Trex deck. The deck overlooks the nicely fenced-in backyard, creating a wonderful space for relaxing, entertaining, and enjoying the outdoors. The finished lower level provides excellent additional living space, including a large family room, full bathroom, laundry room, den/office, and plenty of storage. Conveniently located for commuters and close to everyday amenities, this well-maintained home offers comfort, versatility, and outdoor enjoyment in a desirable neighborhood. Don't miss the opportunity to make this wonderful Ranch your new home!

7 Pine Road, Brewster
$725,000
3 Beds ⋅ 2 Baths ⋅ 1039488 MLS
Your private Brewster retreat awaits. Set back on more than three picturesque, park-like acres, this spacious contemporary raised ranch offers a rare combination of privacy, space, flexibility, and exceptional outdoor living. With over 2,900 square feet, three bedrooms, and a versatile floor plan that lives like a four-bedroom, there is room here to spread out, entertain, work from home, and simply enjoy life. And then there’s the setting. This is where the property truly shines. Surrounded by mature trees, lush greenery, and beautifully maintained grounds, the property feels like your own private escape. The expansive deck overlooks the serene landscape and inviting pool, creating the perfect backdrop for summer entertaining, lazy afternoons, morning coffee, or evenings under the stars. There is a wonderful sense of space and seclusion here that is increasingly hard to find. At the center of the home, the generous kitchen features granite countertops, stainless steel appliances, and oak hardwood floors, while the spacious living areas offer plenty of room for both everyday living and entertaining. A fireplace in the living room and a wood-burning stove in the family room add warmth and character to the home. The spacious primary bedroom with en-suite bath, along with two additional bedrooms, completes the main level. The lower level adds another dimension of flexibility, offering a potential au pair or in-law setup, additional living space, and tons of storage. Whether you need guest space, a home office, recreation area, or simply more room for everyone and everything, this level offers numerous possibilities. The best part? You get the feeling of being tucked away in your own private oasis without sacrificing convenience. Enjoy easy access to shopping, restaurants, two nearby train stations, and major parkways, making commuting and everyday errands a breeze. Three-plus acres. Over 2,900 square feet. Incredible outdoor living. Endless possibilities. And privacy you can feel the moment you arrive. This is the kind of property that needs to be experienced in person.

66 Maple Wood Drive, Brewster
$559,000
4 Beds ⋅ 2 Baths ⋅ 1037538 MLS
Welcome home to this fully updated, sun -drenched private oasis! This home boasts a gourmet kitchen with a center island, perfect for entertaining guests, plus a deck right off the kitchen for effortless indoor-outdoor living. Enjoy a separate dining area and a huge living room with a working fireplace-amazing flow and layout throughout. Three ample sized bedrooms on the top level, plus one huge bedroom on the lower level, make this ideal for extended family. Two full bathrooms, a pool, and complete privacy and seclusion round out this must -see home. Super Low taxes! Priced to move!

97 Old Road, Call Listing Agent
$1,396,000
5 Beds ⋅ 5 Baths ⋅ 1036923 MLS
Don't miss your chance to own this professionally designed Emmett Modern Farmhouse, available for October 2026 delivery in one of Brewster's most sought-after new home communities. With limited opportunities for new construction in the area, this quick move-in home offers the rare combination of luxury finishes, modern efficiency, and the peace of mind that comes with a comprehensive builder warranty. Nestled among picturesque horse farms and riding stables, yet just five minutes from the Brewster Metro-North station, this exceptional residence offers the perfect blend of countryside charm and commuter convenience. Thoughtfully designed for today's lifestyle, the home features a desirable main-level guest suite with a full bath, ideal for visitors, extended family, or multigenerational living. The open-concept design is highlighted by a dramatic 20-foot great room ceiling and a charming wood-burning fireplace, creating an impressive yet inviting space for everyday living and entertaining. The gourmet kitchen flows seamlessly into the main living areas, making gatherings effortless. Upstairs, retreat to the luxurious primary suite, complete with a spa-inspired bath featuring a freestanding Kohler soaking tub. The finished lower level adds valuable living space with a media room, half bath, and flexible recreation area perfect for work, fitness, hobbies, or hosting guests. Enjoy the outdoors from the covered Trex deck, overlooking a private wooded homesite that provides a serene backdrop throughout the seasons. Additional highlights include a side-entry garage, energy-efficient Ply Gem windows, a tankless water heater, and an impressive collection of designer-selected upgrades. Luxury finishes throughout the home include quartz countertops, engineered hardwood flooring, floor-to-ceiling tile accents in select baths, and carefully curated high-end selections that elevate both style and functionality. Skip the lengthy construction timeline and move into a brand-new luxury home this October. This is a rare opportunity to own a professionally designed residence featuring premium upgrades, flexible living spaces, a private wooded setting, and the security of a builder warranty. Quick move-in homes with this level of finish, location, and value are limited, so act now before this opportunity is gone.

45 Drewsclift Drive Unit #25, Brewster
$1,336,000
5 Beds ⋅ 5 Baths ⋅ 1036908 MLS
Discover luxury living in this stunning Emmett New England home, perfectly situated in one of Brewster's newest communities. Surrounded by picturesque horse farms and riding stables, this exceptional neighborhood offers a peaceful countryside setting just five minutes from the Brewster Metro-North train station, providing the ideal balance of privacy and convenience. Designed with versatility and comfort in mind, this thoughtfully appointed home features a main-level guest bedroom and full bath, perfect for visitors, extended family, or multigenerational living. The inviting great room is anchored by a charming wood-burning fireplace, while the gourmet kitchen and open-concept living spaces are ideal for both everyday living and entertaining. The luxurious primary suite serves as a private retreat, highlighted by a spa-inspired bath featuring a freestanding Kohler soaking tub. The finished lower level expands the home's living space with a media room, full bath, and additional flexible living area, offering endless possibilities for recreation, work, or hosting guests. Enjoy outdoor living on the covered Trex deck, overlooking a private wooded backyard that creates a serene natural backdrop year-round. Additional highlights include a side-entry garage and an impressive collection of designer upgrades throughout. This home is beautifully appointed with upgraded design finishes, including floor-to-ceiling tile walls in select bathrooms, quartz countertops, engineered hardwood flooring, and numerous luxury enhancements that elevate both style and functionality. Move in Winter 2026 and enjoy the rare opportunity to own a professionally designed new construction home in one of Brewster's most desirable new communities. Combining luxury finishes, flexible living spaces, natural surroundings, and unmatched commuter convenience, this exceptional residence truly has it all.

43 Drewsclift Drive Unit #26, Brewster
$1,675,000
5 Beds ⋅ 5 Baths ⋅ 1029124 MLS
Custom built in 2001 and set on 3.81 private, tree-lined acres, this 6,620 square foot, five bedroom center hall colonial opens with a two-story entrance and a graceful curved staircase. Off the entrance hall sit a formal living room with its own fireplace and a formal dining room. The kitchen features Bilotta Custom Wood Cabinetry, granite countertops, and stainless steel appliances, centered on a large island with a sunny dine-in area. It opens directly into the family room, where a second fireplace and a wall of windows continue the scale of the main level. A Game Room and a private office and music Room with french doors to pool sit nearby. A main-level bedroom with full bath adds flexibility for guests and a laundry room rounds out the main level. Upstairs, the primary suite has its own fireplace, a sitting area, extensive walk-in closets and a spa bath and a Sauna. Three additional bedrooms and two full baths complete the floor. The walk-out basement adds 3,757 square feet beyond the home's 6,620 listed square feet, space for a gym, media room, or other use. Outside, an in-ground gunite pool and deck are set against the picturesque acreage and mature trees. An exceptional four-car garage and another 1,162 square feet unfinished space above that is walk in from the entrance area of main house. Built for entertaining and everyday living alike.

65 Indian Wells Road, Brewster
$1,875,000
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
$549,999
3 Beds ⋅ 2 Baths ⋅ 1023579 MLS
Welcome to this beautifully renovated lakefront ranch in the heart of Brewster! Situated on an impressive 0.75-acre property, this move-in-ready home offers the perfect blend of modern updates, comfort, and scenic waterfront living. Featuring 4 spacious bedrooms and 2 full bathrooms, this meticulously maintained home has been completely renovated. Enjoy a bright and inviting layout, updated finishes throughout, and a full finished basement providing additional living, recreation, or entertaining space. Recent improvements include brand-new siding, adding to the home’s exceptional curb appeal. The forced-air heating system ensures year-round comfort, while the stunning lakefront setting creates a peaceful retreat right in your own backyard. Whether you’re looking for a full-time residence or a weekend getaway, this exceptional waterfront property offers it all. A rare opportunity to own a beautifully updated lakefront home on three-quarters of an acre—this is truly a must-see!

917 Drewville 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
$459,999
2 Beds ⋅ 2 Baths ⋅ 1016395 MLS
Completely renovated and move-in ready, this 2-bedroom, 2-bath Cape Cod in the desirable Putnam Lake community offers the perfect blend of modern updates and classic charm. Extensively rebuilt from the inside out, the home features spray foam insulation throughout the first and second floors, new windows, updated electrical and plumbing systems, renovated bathrooms, an updated kitchen, and new appliances. Hardwood floors run throughout the home, while the inviting living room is anchored by a stone-front wood-burning stove. The kitchen showcases shaker-style cabinetry, stainless steel appliances, and contemporary finishes. Both full bathrooms have been thoughtfully updated, including one with a soaking tub and another with a frameless glass shower. The second floor offers vaulted ceilings, dormer windows that provide abundant natural light, and built-in storage areas that maximize functionality. Freshly primed walls throughout create a clean canvas ready for personal touches. Situated on a 0.37-acre lot with Putnam Lake rights and located within the Brewster Central School District, this home offers the convenience of modern construction standards with the character of a classic Cape Cod design. With significant improvements already completed, this turnkey property is ready for its next owner to move in and enjoy.

29 Overlin Road, Patterson
$495,000
2 Beds ⋅ 1 Baths ⋅ 1010538 MLS
Welcome to this charming ranch-style home nestled on nearly half an acre of flat, level property. From the moment you step inside, you'll appreciate the warmth, comfort, and endless possibilities this home has to offer. Whether you're a first-time homebuyer looking for a place to call your own or an investor seeking a great opportunity, this property provides the perfect canvas to make it your own. Home is being sold as is! Enjoy the convenience of being within walking distance to public transportation and just a short drive to the Metro-North Train Station, I-84, I-684, shopping, dining, and all that the area has to offer. Located minutes from Brewster schools, this cozy and quaint home offers both charm and accessibility. Don’t miss your chance to own this wonderful property—schedule your private showing today and start imagining the possibilities!

15 Maple Drive, Brewster
$475,000
3 Beds ⋅ 2 Baths ⋅ 1006422 MLS
Turn your housing payment into an investment! Whether you're a first-time buyer, investor, or looking for multi-generational living, this move-in-ready two-family offers the opportunity to live in one unit while rental income from the second helps offset your mortgage. Featuring a spacious 2-bedroom apartment and a comfortable 1-bedroom apartment, this well-maintained property has already been updated, making it truly turnkey. Additional highlights include a detached garage, off-street parking, separate utilities, an unfinished basement with abundant storage, and a convenient location just minutes to the Metro-North station, shops, restaurants, parks, and major highways. A rare opportunity to own an income-producing property that's ready from day one.

159 Main Street, Brewster
$999,000
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

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.