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$950,000
3 Beds 2 Baths 22603572 MLS
Welcome to 1016 Stony Brook Road, a beautifully appointed center-entrance Colonial thoughtfully designed to replicate the timeless elegance of a classic New England Sea Captain's home. Built in 1999, this exceptional residence offers approximately 2,000 square feet of thoughtfully designed living space, combining the charm and architectural details of a historic home with the benefits of newer construction. Rich in character, the home features gleaming hardwood floors, custom built-ins, pocket doors, wainscoting, and detailed millwork throughout. A double-sided fireplace connects the living room and den, creating a warm and inviting atmosphere perfect for everyday living and entertaining. The second floor offers three spacious bedrooms, a home office, and a Jack-and-Jill bath. A walk-up attic with skylight and full walk-out basement provide excellent opportunities for future expansion, including the potential for additional living space and a third bath. Set along one of Brewster's most scenic roads within the Historic District, this property abuts conservation-protected land, offering privacy, tranquility, and a beautiful natural backdrop. Enjoy being just minutes from the Stony Brook Grist Mill, Brewster's renowned beaches, conservation trails, and charming village amenities. This rare opportunity blends timeless craftsmanship, classic Cape Cod charm, and modern convenience in one of Brewster's most desirable locations.

1016 Stony Brook Road, Brewster

$1,450,000
4 Beds 4 Baths 22603393 MLS
Welcome to this spacious, meticulously kept home, perfectly sited on an expansive lot (almost 2 acres!) that offers both privacy and pretty woodlands offering plenty of room to enjoy the outdoors. Thoughtfully cared for inside and out, this inviting property combines timeless charm with generous living spaces designed for comfortable everyday living.The main level offers easy one-floor living with gorgeous living and dining rooms, office, kitchen, den, primary suite plus 1st floor laundry room. The lower, walkout level is bright and open with large family room, craft studio, bdrm, full bath and utility-storage area. The 2nd floor offers 2 large bdrms, full bath and spacious attic. Other nice touches include new heat, water tank and feshly painted exterior plus a 2-car garage, gorgeous back deck and front porch, pretty gardens and mature plantings, lofty ceilings and hardwood thru-out much of the 1st floor. Located in one of Brewster's most desirable areas, this exceptional property offers the perfect blend of space and comfort with easy access to beaches, dining, shopping and golf. Not to be missed!

69 Martingale Lane, Brewster

$1,479,000
4 Beds 3 Baths 22603359 MLS
N of 6A. MUST SEE Stunning, Exceptional, Extraordinaire, Chic & Light -filled! Brewster Greek Revival with approx 2,249 sq ft and a rare combination of historic N.E. character, with thoughtful modern updates. Outside it feels like a private sanctuary with mature trees and landscaped grounds creating true seclusion on close to an acre setting and minutes to beaches. A one car garage with a barn/shed attached to it for all your outdoor items.First flr plan consists of a sitting room/den directly as you enter rear of house, a custom Chef's kitchen with a center island. Off the dining area is a very large laundry room which could serve also as a pantry, plus a very pretty full bath with tub. Also off the kitchen is the access to the charming screened -in porch, facing South to gather in for morning breakfast or use during inclement weather days, Beyond the DR off the kitchen is a living room/library with a classic center double sided fireplace serving both rooms. The second level consists of a half bath plus a primary bdrm with an ensuite full bath with shower and the rest of the bedrooms.Gas heat, Roof 2019, washer ~1 yr old and more has been updated. A coastal delight

44 Brier Lane, Brewster

$2,000,000
4 Beds 4 Baths 22603348 MLS
Where life slows to the rhythm of nature, over 800 acres of protected Punkhorn Conservation become a way of life. Hidden at the end of a quiet cul-de-sac in coveted Deerfield Estates, this nature's reserved area embraces Upper Mill & Seymour Ponds to create one of Brewster's most idyllic settings. There are places that invite you to visit & there are places that invite you to stay. This is one of them. This beautifully renovated four bedroom, four bath turnkey Cape offers an effortless blend of privacy, comfort, and resort-inspired living. Summer afternoons drift effortlessly from the sparkling pool to the spa before ending with sunset cocktails at your custom tiki bar, where conversations linger longer after the stars appear. Mornings begin with nature, bike rides, kayaking or swimming at Upper Mill Pond a mile away. Dream on in to experience soaring ceilings w/ skylights, gleaming hardwood floors, a heated two-car garage, thoughtful finishes and design selections to create an atmosphere of understated elegance. Offering two suites, a formal dining, eat-in kitchen, spacious deck & finished lower level, this isn't simply where you'll live, it's how you'll remember truly living.

37 Autumn Court, Brewster

$675,000
2 Beds 2 Baths 22603281 MLS
Classic charm and modern conveniences make this spacious 2+ bdrm the perfect year round or seasonal getaway. Located in that sweet center area of Brewster with easy access to beaches, shopping and local-flavor restaurants, this property has been thoughtfully updated over the years; brand new roof (2026), kitchen, VT Castings gas stove, newer water heater, many windows and lower level walkout has new heat and specialized dehumidifying system. Main level offers 2 bdrms, full bath, sunny living room and dining-kitchen area with direct access to a raised deck. A perfect spot to relax! Lower level is walkout with large recreation room, studio space plus full bath and laundry room. Outdoor space has new walkways, outdoor shower, mature plantings and circular drive.This is a special property with a comfy warmth, exuding charm and ready for new memories!

267 Alden Drive, Brewster

$719,000
3 Beds 2 Baths 22602844 MLS
Welcome to this exceptional, single-level retreat beautifully positioned on its lot in the heart of Brewster. Designed for effortless Cape Cod living, this home features a seamless open-concept layout anchored by a cozy gas fireplace perfect for gathering after a day at the bay. Kitchen is oversized with wet bar & center island. The primary suite boasting an oversized bathroom & generous closet space throughout. Convenience is key with a dedicated laundry room right off the kitchen & an EV/RV charger already installed outside. An impressive, unfinished walk-out basement spans the entire length of the home offering a blank canvas to easily add a recreation room, home gym or extra guest quarters. Step outside to a beautifully private backyard with plenty of room for property expansion or gardens. Minutes from Brewster's famous beaches, the Cape Cod Rail Trail, and historic Route 6A, this property blends turnkey comfort with incredible future potential. Your Cape Cod chapter starts here!

49 Thousand Oaks Drive, Brewster

$2,400,000
4 Beds 5 Baths 22602397 MLS
This coastal contemporary cape style home by Eastward companies is one of a two lot Brewster subdivision close to beautiful Crosby Landing Beach, The Cape Cod Rail Trail and the Town of Orleans. Exceptional custom finish work enhances the superb floorplan and rich amenities. The cathedral great room incorporates the chef's kitchen with Thermador appliance package & 10' center island, fireplaced living room and breakfast room. A four-season sunroom adds natural light and a quiet space. A formal dining room, primary bedroom suite, mud room and laundry complete the first floor living option. Upstairs are a loft/office and three guest bedrooms. The finished lower level with 9' ceilings, a full bath and full-sized windows offers space for exercise, media or a playroom. The natural setting, artful landscape plan and large patio with gas fire pit provide for outdoor enjoyment. There is ample room for an inground pool. Natural gas utilities, EV charger, low-maintenance composite exterior. Convenient location is close to Orleans activities, Nickerson State Park. Buyer customization is welcome at this stage, delivery of completed home in 2027. Photos are of a similar, completed home.

47 Bay View Drive, Brewster

$1,450,000
5 Beds 4 Baths 22602346 MLS
This beloved classic colonial occupies one of the best locations in Beechwood Landing Association, conveniently close to both the sandy association beach on Greenland Pond and the boating access and mooring field on Long Pond. A gathering place for generations, this home is loaded with character and offers three levels of finished space for friends and family. Linger on the farmer's porch, then enter the multiple living spaces which include a great room with a cathedral kitchen and fireplace, a front-to-back living room and an inviting a four season sunroom. Upstairs are four bedrooms including the primary suite. The finished walkout level offers a 2nd kitchen, more sleeping space & a full bath. Traditional finishes throughout harken back to a time of long, leisurely Cape summer vacations. For the hobbyist there's a spacious workshop/studio above the garage. Recent updates include a new roof (2026), gas generator, heating system & 6br septic (2009). The private yard is beautifully planted with perennials, beech trees & evergreens. Enjoy Brewster's finest freshwater boating and swimming from the superb association amenities. The abutting 2+ acre lot is also available for purchase.

206 Landing Drive, Brewster

$2,400,000
4 Beds 6 Baths 22602254 MLS
This luxurious, classic New England Cape-style home by Eastward Companies is one of a new two lot Brewster subdivision close to beautiful Crosby Beach, The Cape Cod Rail Trail and the Town of Orleans. Form meets function at the highest level with an exceptional degree of custom finish work. The cathedral great room is the home's hub, it combines the Thermador-equipped kitchen with the fireplaced living room and dining area, all of which is open to the vaulted sunroom. Three levels of finished space include a complete first-floor living arrangement with the luxurious primary suite, laundry, pocket office, garage, mudroom and entertaining areas all accessible. Upstairs are two substantial guest bedroom suites with cathedral ceilings. The fourth bedroom is a private suite above the garage with a separate entrance, ideal for long-term guests. Eastward's signature attention to finish work is evident throughout, from the distinctly decorated baths to the 900+- sq ft of rec space in the 9' ceiling-height finished lower level with full bath. An optional inground pool is available. Delivery in 2027. At this stage Buyer input as to finishes is welcome. Photos are of a similar home.

55 Bayview Drive, Brewster

$2,492,000
3 Beds 2 Baths 22602214 MLS
This is an absolutely enchanting waterfront property with private stairs to your own private beach on glistening Cape Cod Bay! With an ever-changing palette of gorgeous views from sunrise to sunset to high and low tides; you'll never want to leave this amazing spot! Sit and enjoy this warm and welcoming gathering place ... swim, play and enjoy the world renowned Brewster tidal flats, kayaking and the warm sun! The adorable main house offers idyllic Brewster living with multiple waterviews, sliders to deck, sandy beach path, kitchen, dining, living room plus family room and 2-bdrms up. The cottage offers a unique separate studio, seasonal living space with own kitchen/bedroom/bath. A fabulous spot for overflow guests. This is an incredible rental property in high demand year after year with returning guests. A waterfront gem with its own private beach on Cape Cod Bay doesn't come along very often!

232 Robbins Hill Road, Brewster

$1,839,000
2 Beds 4 Baths 22601942 MLS
Discover a rare opportunity to own a brand-new waterfront retreat in the heart of Brewster, set directly on the shores of picturesque Schoolhouse Pond. Designed for unforgettable Cape Cod summers, this exceptional home invites you to spend long afternoons on the expansive mahogany deck overlooking the water or launch a kayak right from your backyard. Offering over 3,100 sq ft of impeccably finished living space, the home showcases a stunning chef's kitchen with Thermador appliances, custom cabinetry, and a stylish wet bar, flowing seamlessly into sun-filled living areas anchored by a gas fireplace. A welcoming farmer's porch, elegant stone patios, and professionally designed landscaping with ambient lighting create a true indoor-outdoor lifestyle. Thoughtful smart features include illuminated stairways that light up as you ascend and descend. Thoughtfully designed as a 2-bedroom residence with multiple bonus spaces ideal for guests, office, or formal dining, the home includes a luxurious second-floor primary suite. Just 1.3 miles to Brewster's renowned Bay beaches, this one-of-a-kind waterfront property delivers the ultimate blend of luxury, privacy, and coastal living.

84 Alden Drive, Brewster

$1,270,000
4 Beds 2 Baths 22601601 MLS
Step into a timeless Cape Gambrel built by family for family as the perfect retreat for making lasting memories. Whether it's lazy beach days, cozy afternoons with a book, or rainy-day puzzles, this home captures the essence of Cape Cod living. Idea in town location just a short distance from everything in Brewster! This property includes deeded beach rights and a rare 1/100 share of the highly sought-after Sea Pines Neighborhood Association Beach--widely regarded as one of the most beautiful bay beaches in the area. The home features 4 bedrooms and an open-concept living, kitchen, and dining area with two sliders opening to outside living areas!. A full basement provides additional space and flexibility. Outdoors, enjoy multiple seating areas, a deck, firepit, and two outdoor showers--a true Cape Cod luxury. Recent updates include: New windows and rear slider Durable Azek trim and new gutters; 45-year architectural roof shingles (installed Summer 2012) Natural gas furnace, central A/C, and newer appliances. On a private, level lot, this home offers a peaceful setting with gentle scenic proximity to the shores of Cape Cod Bay. Your own sandy toes and salty kisses can start now!

47 Flying Dragon Road, Brewster

$1,690,000
3 Beds 3 Baths 22601247 MLS
Completed in 2023, this newly built, fully electric home blends elevated design, sustainable living, and timeless Cape Cod charm. Set on 1.15 acres across two parcels (and surrounded by conservation) with private access to Blueberry Pond, the residence offers ~2,400 sq ft across three thoughtfully designed levels. The home was designed with a primary suite on each of the main levels, offering flexibility for multigenerational living or guests. The second floor serves as a private sanctuary, featuring an expansive primary suite with a sitting room, dedicated workspace, and views over native wildflower meadows to the water. The walk-out lower level--with separate entrance and driveway--functions as an ideal guest suite or income-generating Airbnb (earning ~$30K/year). Finishes include Miele appliances, heated towel rails, engineered hardwoods, and Pella windows. A HERS rating of 50, 400-amp power, solar-ready infrastructure, and dual EV chargers reflect true modern efficiency. A screened porch, outdoor shower, and curated gardens complete this rare Brewster retreat--just moments to the Rail Trail and First Light Beach. This home has a passing 4 bedroom Title V Septic.

410 Blueberry Pond Drive, Brewster

$765,000
3 Beds 2 Baths 22601110 MLS
Freshly price adjusted and motivated seller! Built in 2016 and lovingly maintained by its original and only owner, this move-in ready Ranch offers the ease of one-floor living with a thoughtful, low-maintenance design. Set on over an acre with association rights to Upper Mill Pond and beach area, the home combines privacy, comfort, and functionality in a peaceful setting.The open-concept layout features a spacious kitchen with island and breakfast bar flowing into the dining area and out to a large deck ideal for entertaining or relaxing summer evenings. The primary suite offers a private full bath, while two additional bedrooms provide flexibility for guests, office space, or hobbies. A practical mudroom with laundry, central air, gas heat, full-house generator that makes storms a breeze, leased solar panels that provide valuable electric bill credits, inviting front porch, and insulated and finished two-car garage add to the home's everyday convenience and efficiency.A rare opportunity to own a newer Cape home with modern systems, an easy-living floor plan, and room to simply enjoy life. All parties to verify information contained herein.

98 Leland Road, Brewster

$1,479,000
2 Beds 4 Baths 22600807 MLS
Exceptional new custom-built smart home lives large with nearly 3,000 sq. ft. of flexible living space--perfect for extended family and friends. Great location - close to Oceans Edge Golf Course, Beaches, Nickerson State Park & Rail Trail. Charming cul-de-sac location with a local fruit farm just across the street. The open-concept design features white oak flooring, a first-floor office, second-floor study, & finished lower level with family room & bonus area--ideal for a gym or home cinema. The chef's kitchen offers Samsung smart appliances, custom cabinetry & high-end quartz countertops flowing into a bright living area and sunroom, which overlook the backyard with an outdoor shower & custom shed. Spa-inspired baths include heated floors & smart commodes. Five heating/cooling zones, Mitsubishi dual-fuel system, IA septic, private well for economical landscaping, & smart-home controls enhance efficiency--truly a must-see! BUILDERS' HOME WARRENTY INCLUDED WITH SALE. Buyer acknowledges the Seller must comply with FIRPTA regulations in association with this sale. Upon written request from the Seller the Buyer (s) agrees to extend the closing date for a reasonable amount of time so Seller can obtain a ''Withholding Certificate'' from the IRS prior to the Closing. IA septic-yearly maintaince fee . Taxes are not accurate; check with the town.

58 Old Chatham Road, Brewster

$1,940,000
4 Beds 4 Baths 22600329 MLS
Gracing a knoll above charming and historic Rt 6A on exclusive Ridgewood Dr(Map 26-58), this large lot boasts privacy, and a one-of-a kind view across Drummer Boy Park, Quivett Marsh, and Cape Cod Bay beyond! This new construction pkg offers a rare opportunity to create your dream home in one of Cape Cod's most picturesque settings! With a recent 5 BR septic perc test--there are so many possibilities for your future home! In collaboration with Millbrook Homes, the featured plan checks all of the boxes--1st floor primary BR suite, open layout with living room, dining area, and a family room with fireplace, AC, and a 2 car garage. Upstairs, a loft plus 3 more BRs (1 ensuite!) and unfinished bonus room. Modify it or bring your own plan. Or just buy the lot (MLS#22600881) and hire your own builder! Across the street, Drummer Boy Park offers open green space, historic windmill, and gazebo where the Town Band serenades on summer evenings. Little ones will adore the play area at the Park and nature lovers can explore the scenic trail to the Wing Island conservation area where you'll discover one of the most unspoiled beaches on Cape Cod Bay! See video! Buyers/agents to confirm details.

Ridgewood Drive, Brewster

$1,655,000
4 Beds 4 Baths 22505169 MLS
Stunning Brewster Home!Just minutes from beaches and premier golf courses, this meticulously maintained residence offers the perfect blend of casual elegance and modern comfort. The bright, open floor plan features a gourmet kitchen with center island, custom cabinetry, and gleaming Roca tile floors. The inviting living room flows into the dining area, featuring a soaring ceiling, a gas fireplace and sliding doors that open to a spacious deck overlooking the private backyard.Throughout the home, you'll find custom window shutters and exquisite hardwood floors. There are two primary suites, one on each level, along with two guest bedrooms--one currently used as a sitting room. Additional highlights include beautifully appointed bathrooms, 1st floor laundry, natural gas heat, central air conditioning, a whole-house generator, irrigation system, and an atttached two-car garage with potential bonus space above. A welcoming front porch and professional landscaping complete this stunning oasis, privately nestled on a cul-de-sac surrounded by protected greenspace in a lovely neighborhood.

80 Abby Road, Brewster

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