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$799,999
3 Beds ⋅ 2 Baths ⋅ 1049145 MLS
A Rare Brewster Estate-Sale Opportunity! Set on beautiful, expansive grounds surrounded by mature landscaping, this distinctive raised ranch offers a wonderful combination of space, privacy, and property. Welcome to this spacious and versatile 4,032 sq. ft. raised ranch in Brewster, offering an inviting open floor plan and abundant living space. Hardwood floors, two fireplaces, and generous room sizes provide a wonderful foundation to make this home your own. The finished lower level offers additional space for recreation, entertaining, a home office, gym, or guest accommodations. Enjoy the private inground pool and create your own backyard retreat. A 5-bedroom septic system adds flexibility for a variety of living arrangements. A wonderful opportunity to bring your vision to a substantial Brewster home offering space, flexibility, and tremendous potential. Conveniently located near the train station and major highways, offering easy access for commuters while enjoying the tranquility of a spacious property setting. Town Building Department records reflect 3 bedrooms and 1.5 baths, while Town Assessor records reflect 5 bedrooms and 3.5 baths. Buyers are encouraged to conduct their own independent due diligence. Any engineering inspection or evaluation obtained by the buyer shall be for the buyer’s informational purposes only. Estate sale; property is being sold strictly AS IS.

52 Friendly Road, Brewster
$2,795,000
4 Beds ⋅ 7 Baths ⋅ 1048047 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
$998,000
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
$699,900
3 Beds ⋅ 3 Baths ⋅ 1012164 MLS
Nestled on a picturesque 1.91-acre parcel along a tranquil cul-de-sac in Harvest Ridge, this pristine, turn-key Colonial offers a seamless blend of architectural charm and modern convenience. This move-in ready home features 3 spacious bedrooms, 2.5 beautifully renovated baths, and a 4-bedroom septic system offering expansion potential. The heart of the home is a light-filled gourmet chef's kitchen, complete with stainless steel appliances, a high-end Bertazzoni gas range, granite countertops, a center island with seating, a custom tumbled marble backsplash, refinished cabinetry, and durable bamboo flooring. The kitchen flows effortlessly into an inviting living space featuring a cozy fireplace, while French doors open to a sun-drenched deck overlooking a serene, wooded backdrop—ideal for alfresco dining and summer entertaining. A versatile main-floor office provides flexible space for a quiet home workspace, library, or den. The elegant formal dining room is perfect for hosting holidays and memorable dinners. Upstairs, retreat to a lavish primary en suite featuring a spa-inspired bathroom featuring a new double vanity, a renovated shower, a deep soaking tub, and custom closet built-ins. Two additional bright bedrooms with custom storage closets, a refreshed full hall bath, and a generous storage closet complete the upper level. The fully finished lower level expands your living space, boasting a wet bar, recreation space, family room, and abundant private storage. Recent upgrades include: new bamboo flooring throughout the main level, new carpet on the stairs and second level, fresh interior paint, and updated light fixtures throughout the home. Enjoy relaxing walks and bike rides throughout Harvest Ridge. This home is conveniently located near schools, the train, local restaurants, and local farmers markets.

4 Plum Tree Court, Brewster
$1,025,000
4 Beds ⋅ 3 Baths ⋅ 1009323 MLS
Welcome to this stunning brand-new custom farmhouse-style home in Brewster, offering the perfect blend of modern luxury and timeless design. Situated on .44 acres, this beautifully crafted 4-bedroom, 2.5-bath residence features 9-foot ceilings, custom finishes throughout, and exceptional attention to detail. The heart of the home is the designer kitchen, complete with premium Café appliances, a 9-foot waterfall quartz island, built-in microwave, custom cabinetry, and elegant crown moldings. The open-concept layout flows seamlessly into the spacious living areas, creating an ideal space for both everyday living and entertaining. Additional highlights include custom flooring throughout, a luxurious primary suite with an oversized walk-in closet, Ply Gem windows, spray foam insulation from attic to basement for superior energy efficiency, and radiant heated floors in the basement. Exterior features are equally impressive, including James Hardie siding, two stone entry pillars, a paver driveway and walkways, an attached 2-car garage, and a yard irrigation system. Connected to a community septic system and conveniently located near Southeast and major commuter routes. A rare opportunity to own a thoughtfully designed new construction home with high-end finishes and quality craftsmanship throughout. HOA: Approximately $500/quarter (subject to change)

20 Sophia Lane, 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.