Brewster Homes with Attached Parking features

Welcome to Brewster, New York – a charming town nestled in the heart of Putnam County. Known for its picturesque landscapes and rich history, Brewster offers a unique blend of small-town charm and modern conveniences. With its close proximity to the scenic beauty of the Hudson Valley and easy access to New York City via the Metro-North Railroad, Brewster is an ideal location for those seeking a peaceful retreat without sacrificing urban amenities.

As you explore the real estate options in Brewster, you'll discover a variety of homes that cater to diverse lifestyles. One of the standout features of many properties in this area is the availability of attached parking. Whether you’re a commuter needing quick access to your vehicle or a family looking for the convenience of off-street parking, homes with attached parking provide a perfect solution. No more worrying about street parking or inclement weather – simply park your car and step inside your cozy abode.

Brewster is not just about homes; it’s about community. Residents enjoy local parks, charming shops, and a vibrant dining scene that showcases the best of upstate New York. Outdoor enthusiasts can take advantage of nearby hiking trails, lakes, and recreational areas, making Brewster an ideal place for families and individuals who appreciate nature.

If you're looking for a home that combines comfort, convenience, and community spirit, Brewster is the perfect place to call home. Come explore the possibilities and discover your dream residence in this delightful town!

Newest Brewster Homes with Attached Parking features

$425,000

3 Beds ⋅ 2 Baths ⋅ 1050325 MLS

Opportunity Knocks! This well loved 3 bedroom ranch offers 1,665 square feet of living space on a level .25-acre lot with town water and sewer. The main level features a spacious living room with a fireplace, formal dining room, and kitchen, along with three bedrooms and a full hall bath. Hardwood floors and central air conditioning add to the home's appeal. The Basement includes a large family room complete with a wet bar and full bathroom, a generous size unfinished area ideal for storage, workshop space, or future expansion and the Laundry area. You will love the outdoor living area with the oversized covered rear deck overlooking and connecting directly to the above-ground pool, making it perfect for entertaining and summer enjoyment. Additional features include a one-car garage, shed and ample storage. Conveniently located just 2 miles from the Brewster Metro-North train station and minutes from I-684 and I-84, this home offers easy commuting and close proximity to schools, shopping, restaurants, and everyday conveniences. While the property has been well maintained over the years, it is in need of updating and repairs and is being sold strictly as-is. An ideal opportunity for investors, contractors, or handy buyers looking to restore and personalize a home in a desirable commuter-friendly location and sought after neighborhood!

21 Allan 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

$1,299,000

4 Beds ⋅ 3 Baths ⋅ 1037425 MLS

Discover luxury living at Homesite #35, featuring the highly sought-after McCourt Modern Farmhouse in Toll Brothers' newest premier community in the Town of Southeast. Perfectly positioned on a desirable corner homesite, this elegant home blends sophisticated design, exceptional craftsmanship, and modern luxury. The thoughtfully designed floor plan offers the convenience of a first-floor primary bedroom suite, creating a private retreat complete with a spa-inspired bath featuring a stunning Kohler freestanding soaking tub. The inviting great room is anchored by a charming wood-burning fireplace, providing warmth and character throughout the seasons. Step outside and experience the ultimate in indoor-outdoor living with an expansive luxury outdoor space featuring premium TimberTech decking, ideal for entertaining, dining al fresco, or simply enjoying the beauty of your surroundings. Upstairs, three generously sized bedrooms offer comfort and flexibility for family and guests. Additional highlights include a 2-car side-entry garage and rough plumbing in the basement, providing the opportunity for future finished living space tailored to your needs. Projected for a Winter 2026 move-in, this exceptional home comes with designer-selected features and finishes that have been thoughtfully curated to complement its stunning architecture and modern farmhouse style. Located within one of the area's most anticipated luxury communities, Homesite #35 offers the perfect combination of elegance, comfort, and convenience. With limited opportunities available, this is your chance to own a beautifully crafted new home from one of the nation's leading luxury builders. Take advantage of our limited Quick Move-In sales event offering exclusive incentives!

2 Serenity Ridge Lane Unit #35, 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

$1,250,000

4 Beds ⋅ 4 Baths ⋅ 1026366 MLS

Welcome to your own private riverside retreat, where exceptional craftsmanship, contemporary design, and breathtaking natural beauty come together in perfect harmony. Thoughtfully custom built and meticulously maintained by its original owners, this stunning multi-level residence offers over 3,900 square feet of beautifully designed living space, perfectly positioned to capture tranquil views of the East Branch Croton River. At the heart of the home is a beautifully appointed custom chef’s kitchen featuring a large center island, granite countertops, abundant white cabinetry, a generously sized pantry, dual ovens, a six-burner Viking gas range with a dual-motor, Viking exhaust hood, and a Sub-Zero refrigerator/freezer. Designed for both everyday living and effortless entertaining, the kitchen flows seamlessly into the formal dining room and sun-filled living room. The living room is anchored by a fireplace and showcases striking floor-to-ceiling custom mahogany tilt-and-turn windows with oversized glass panels that flood the home with natural light while framing picturesque river views. Step outside to the expansive deck, an ideal setting for outdoor dining, entertaining, or simply relaxing as the seasons unfold along the water's edge. The elegant formal dining room provides the perfect backdrop for gatherings and special celebrations. Completing the main level are a full bath, laundry room, and a versatile flex space featuring a pass-through to the kitchen, breakfast bar, and direct access to the deck—ideal as a casual dining area, sitting room, home office, or reading nook. Upstairs, the luxurious primary suite serves as a peaceful sanctuary with generous space for sleeping, lounging, and dressing with two walk in closets. A stunning double-sided fireplace creates warmth and ambiance for both the bedroom and spa-inspired ensuite bath, complete with a walk-in shower, Jacuzzi tub, skylight, and vanity. A private balcony offers the perfect place to enjoy your morning coffee or unwind with a good book while overlooking the peaceful landscape. Two additional spacious bedrooms, a beautifully appointed full bath with dual vanity and glass-enclosed shower, and an impressive open foyer highlighted by three elegant chandeliers complete the second level. The walk-out lower level features a fully legal one-bedroom accessory apartment with its own private entrance, spacious deck, full kitchen, laundry, and expansive living with flexible space for a dining room or home office. Whether used for multi-generational living, guest accommodations, an au pair suite, or rental income, this thoughtfully designed space offers exceptional flexibility while maintaining privacy for everyone. Set on nearly three idyllic acres, the grounds are every bit as remarkable as the home itself. Lush lawns, mature trees, flowering shrubs, a charming small pond with waterfall, and the gentle flow of the East Branch Croton River create a truly enchanting setting. Wander down the private path to the river, where the soothing sounds of flowing water provide a daily escape. Observe abundant wildlife including egrets, owls, turtles, geese, and other native species, or launch a kayak or canoe and spend the afternoon exploring the peaceful river. Despite its serene and secluded setting at the beginning of 6,000 acres of The Great Swamp, this extraordinary waterfront property is just minutes from Metro-North, major highways, local shops, restaurants, hiking trails, Thunder Ridge Ski Area, and all the charm, recreation, and culture the historic Hudson Valley has to offer. Where luxury meets nature, and every day feels like a peaceful escape.

23 River 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

$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 final stages of completion, 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 freestanding soaking tub beside a large, glass-enclosed walk-in 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

$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

$739,999

4 Beds ⋅ 3 Baths ⋅ 990889 MLS

Welcome to 33 Orchard Ct in Brewster, NY — a beautifully maintained Colonial set on nearly one private acre in a peaceful cul-de-sac setting. Built in 1994, this spacious 4-bedroom, 2.5-bath home offers the perfect combination of classic charm, functional living space, and everyday comfort. Inside, you’ll find a bright and inviting layout featuring an open-concept kitchen ideal for both daily living and entertaining. Generous living spaces, abundant natural light, and a seamless flow create a warm and welcoming atmosphere throughout the home. Ideally situated close to shopping, restaurants, on Rte 22, Brewster schools are right around the corner as well as parks, Metro-North, 84 and 684. Enjoy easy access to all that Brewster and the surrounding Hudson Valley have to offer, including recreation, dining, and everyday conveniences just minutes away.

33 Orchard Court, Brewster

$869,000

4 Beds ⋅ 3 Baths ⋅ 982755 MLS

Introducing a to-be-built residence crafted by an experienced local builder known for quality and attention to detail. Thoughtfully planned with today’s lifestyle in mind, this beautifully designed raised ranch with subtle Colonial flair offers both comfort and functionality. Perfectly sited on over three acres, the proposed home will feature an open-concept floor plan filled with natural light, ideal for everyday living and entertaining. The spacious living room flows seamlessly into an eat-in kitchen, with sliders leading to a large deck—perfect for indoor-outdoor gatherings. The primary suite will serve as a peaceful retreat, complete with a private bath and walk-in closet. Two additional bedrooms on the main level, along with a lower-level bedroom, provide flexible space for guests, multi-generational living or a dedicated home office. Quality finishes and modern amenities include hardwood floors, high ceilings, foam insulation, central air, a gas fireplace, and a two-car garage. The expansive walkout lower level offers a family room, bedroom, full bath, laundry area, and waterproof laminate flooring—ideal for extended living, a guest suite, recreation space, or whatever best suits your needs. Set in a serene location just 75 minutes from New York City, it provides convenient access to Metro-North Railroad, Routes 22, 684, and 84, as well as nearby attractions such as Thunder Ridge Ski Area, along with shopping, dining, and all the charm of the Hudson Valley. Photos include virtual renderings and images of a recently completed similar home. Finishes and features are subject to change during construction. **This is considered a *to be built home* and contract terms will require purchaser to fund the buildout.**

73 Farm To Market Road, 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

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