Chatham Homes

MLS Number 22503617

• Residential
• Bedrooms 5
• Bathroom 4
• Square Feet 4,307
• Town Chatham

Tucked within the exclusive & secluded enclave of Morris Island, this one-of-a-kind water view residence is a rare treasure offering architectural distinction and an intimate connection to Cape Cod's unspoiled coastal beauty. With panoramic views spanning Stage Harbor to the Atlantic shoreline, the home was thoughtfully designed to embrace its extraordinary setting--inviting nature's ever-changing light and tide into every living space. Whether you're taking in the sunrise from the terrace or enjoying quiet moments inside, this residence is a canvas of coastal tranquility and sophistication. Enhancing its unmatched location is a deeded path to the famed Monomoy Trail--an exclusive feature that offers direct access to serene landscapes and protected natural habitats. Step outside and explore miles of scenic trails, salt marshes, and wildlife-rich terrain right from your doorstep. It's an invitation to live in harmony with nature, every day. Inside, you'll find spaces that blend modern luxury with classic charm: soaring ceilings, handcrafted millwork, and expansive windows that frame ocean and harbor vistas. From the chef's kitchen to the spa-inspired baths, each detail reflects a commitment to comfort & artistry. Whether you're entertaining in elegant indoor spaces, relaxing on the sun-drenched deck or patio, or exploring your private path to Monomoy's pristine beauty, this home is more than a place to live - it's a place to thrive. Every detail, view, and moment capture the spirit of life on the Cape, offering a legacy property that's as inspiring as it is inviting.

Listed by Dee M Sullivan and Jenna Sullivan of Christie's International Real Estate Atlantic Brokerage

MLS Number 22504540

• Residential
• Bedrooms 4
• Bathroom 6
• Square Feet 4,717
• Town Chatham

Set on nearly an acre in one of Chatham's most coveted enclaves, this Stage Island residence offers an extraordinary combination of refined craftsmanship and sweeping Stage Harbor views. The welcoming foyer opens to a dramatic living room with walls of glass framing the water, filling the space with natural light. A stylish kitchen with center island and dining area extends to an expansive deck, creating effortless flow between indoors and outdoors. The first floor also features a private ensuite bedroom, cozy den, and laundry area--providing flexibility for both guests and single-level living. Upstairs, three additional ensuite bedrooms include a serene primary suite with panoramic views, a spa-like bath, and spacious walk-in closet. With generous gathering areas and thoughtful details throughout, the home captures the essence of coastal luxury. The lower level adds over a thousand square feet of versatile living space with a large family room, fitness area, mudroom, and powder room. Designed with entertaining and everyday comfort in mind, the home also boasts extensive custom millwork, built-ins, and high-end finishes that elevate every detail. Outdoors, professionally installed Chatham blue granite walkways, a rear patio, and a built-in marine grill set the stage for alfresco dining and summer celebrations. Railings, landscaping, and window treatments throughout the home enhance both style and functionality. From sunrise over the harbor to evenings gathered on the deck, this property embraces its waterfront setting while offering modern ease. Stage Island's rare combination of privacy, natural beauty, and close proximity to town makes this a once-in-a-generation offering along Cape Cod's treasured coastline.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

MLS Number 22503738

• Residential
• Bedrooms 7
• Bathroom 7
• Square Feet 6,521
• Parking Spaces 10

Chatham Waterfront Masterpiece. A private estate on Cape Cod's most coveted coastline in one of New England's most prestigious coastal communities. 44 Buena Vista Road is an extraordinary waterfront estate, a rare offering blending timeless elegance with resort-style amenities. Designed for both grand entertaining and intimate family living, this residence offers sweeping ocean views, sophisticated interiors, and seamless transitions to the outdoors. A grand 5-bedroom, 4 bath, 4,551 sf colonial home with impeccable craftsmanship & 5 fireplace features multiple sun-drenched living spaces and seamless indoor-outdoor flow. The 1,970 sf, 2 bed, 2.5 bath colonial guest house, built in 2016, is perfect for extended family & friends. Nestled along the Chatham shoreline this 2.6-acre property boasts a sparkling in-ground pool, hot tub, and beautifully integrated fire feature. Live an active lifestyle with a private tennis court, half basketball court, space for lawn games and all your summer activities. .2 miles to Hardings Beach, a premier Nantucket Sound beach. This is a once-in-a-generation opportunity to own a legacy estate on the water.

Listed by Shane K Masaschi of Compass

MLS Number 22502888

• Residential
• Bedrooms 4
• Bathroom 5
• Square Feet 4,214
• Parking Spaces 4

Custom Home in Chatham Village. 4-bedroom, 5-bathroom residence located steps from Oyster Pond and its sandy beach. This thoughtful home offers open floor plan, high ceilings, hardwood floors and expansive water views. Deeded access to an association dock and mooring field for boating enthusiasts. The gourmet kitchen features stone countertops, large center island with seating, and premium appliances. The kitchen flows seamlessly into a bright dining and living area with fireplace - perfect for entertaining. The first-floor primary bedroom includes a walk-in closet, gas fireplace, and ensuite bath. There is a 1/2 bath on the first floor as well as laundry room with utility sink, mudroom, and ample storage. Upstairs, a vaulted-ceiling family room with wet bar opens to porch overlooking Oyster Pond. Three bedrooms, each having a generous closet space and two full baths complete the 2nd floor. The finished lower level includes an entertainment area and 1/2 bath. Outdoor highlights include stone patios, gas firepit, outdoor shower, generator and professionally landscaped grounds. This property offers location, design, and amenities in one of Chatham's most sought-after neighborhoods.

Listed by Timothy P Bailey of John C Ricotta & Assoc.

MLS Number 22501564

• Residential
• Bedrooms 5
• Bathroom 3
• Square Feet 1,896
• Parking Spaces 10

This private oasis in North Chatham , hidden by a long and winding lane, takes you into the past. A spectacular historic setting including natural vegetation rests on one of the last large water front parcels in Chatham. Surrounded by over 1.5 acres, with opportunities for a family compound on a fabulous bluff overlooking, and ownership of, prime beach front on Chatham Harbor, Pleasant Bay, and the Atlantic Ocean beyond. Over 114 feet of private beach protected by a beautiful rock revetment. Quick salt water access to anywhere by boat from your own beach. A perfect spot for relaxing, entertaining under the sun or stars and creating lasting memories .This coastal property features panoramic water views, five bedrooms, three baths, and 1850+ square feet of living space to leave as you will or make it your own... A 69,000 plus square foot lot in R 40 zone would allow a guest house and a pool with town approvals in addition to the main house. A short jaunt to Main Street, Chatham Bars Inn and Wequassett, and all that Chatham has to offer....Buyers and agents should verify all information herein.

Listed by John B Burke and Catherine L Stevens of William Raveis Real Estate & Home Services

MLS Number 22502496

• Residential
• Bedrooms 5
• Bathroom 6
• Square Feet 5,620
• Parking Spaces 5

This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous storage, and space for an 8-seat table by a picture window. The layout includes a family room with fireplace, living room with fireplace, and dining room. There is a finished basement with full bath adding flexibility and function. Upstairs are two ensuite bedrooms, plus three more bedrooms, two additional full baths and dedicated laundry room. You'll also find an office nook and access to a rooftop deck/widow's walk with water views. An attached two-car garage and deeded access to a quiet stretch of Stage Harbor Beach complete the home. Properties like this seldom come on the market.

Listed by Timothy P Bailey of John C Ricotta & Assoc.

MLS Number 22503957

• Residential
• Bedrooms 5
• Bathroom 5
• Square Feet 3,225
• Parking Spaces 6

LIGHTHOUSE BEACH - A Nantucket-inspired coastal home designed and built by Polhemus Savery DaSilva, this residence beautifully blends elegance and comfort. The open floor plan showcases oversized windows and soaring ceilings, allowing natural light to pour in and illuminating the stunning views of the swimming pool, spa, outdoor kitchen, patio, gas fire-pit, outdoor shower, and irrigated fenced-in lawn. Ownership includes deeded neighborhood access to Lighthouse Beach. The gourmet kitchen and oversized island seamlessly integrate with the dining room, custom bar, pantry, and wine storage. The inviting living room features a cozy gas fireplace. The fifth bedroom has been thoughtfully transformed into an inspiring study. Ascending to the second floor, you'll discover four wonderfully proportioned bedrooms, each offering distant Atlantic Ocean views, and three stylish full baths. The primary suite is a true retreat, boasting glorious views, a spacious walk-in closet, a dressing room, and an exquisite bathroom and shower. Around the corner is the Outermost Harbor Marina, and the nearby Old Village is the gateway to the start of Chatham's Main Street.

Listed by The Bohman Hartung Group of Gibson Sotheby's International Realty

MLS Number 22503829

• Residential
• Bedrooms 2
• Bathroom 3
• Square Feet 1,850
• Town Chatham

Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future 4-bedroom main house w/swimming pool, allowing you to envision the next chapter of luxury living on Cape Cod. Whether you're looking to enjoy the existing home w/separate post & beam garage w/power & water, or build your dream estate, the possibilities are truly remarkable. Additional to the expansive waterfront, this property boasts access to an adjacent cove down a winding 10-foot path. The current home features wood floors, a 2-car garage, office & generous outdoor living areas. An expansive deck provides the perfect vantage point to take in the ever-changing coastal scenery & sea breezes. Combining timeless Cape Cod charm with a vision for the future, 99 Uncle Alberts Dr is a one-of-a-kind offering on the waterfront, perfect for those seeking privacy & a truly iconic Chatham location.

Listed by Shane K Masaschi of Compass

MLS Number 22504282

• Residential
• Bedrooms 6
• Bathroom 7
• Square Feet 5,721
• Parking Spaces 15

The first of two homes in a private, gated South Chatham enclave retreated off Main Street and bound in the rear by over 550' of Chatham Bike Trail. The first home is an uncommonly stylish 5700 +/- SF destination home designed for generational use and comfort situated on a magnificent piece of land with numerous recreational possibilities (see proposed tennis/ pickleball location), direct private Chatham Bike Trail access, heated salt water swimming and so much more. With twelve rooms, six bedrooms, five baths, two half baths and a private office, the home is impressively situated on 1.63+/- acres of estate like grounds which have incorporated old world trees preserved intentionally to further adorn the property. With an abundance of custom new construction features, exterior grounds this grand in scope and absent of wetlands for unrestricted utility and priced under $975.00 a foot. Reimagined from its former use as a 3.35+/- acre ''Farmette'' even equestrian possibilities could be refashioned with the adjoining house lot (to be sold separately). An impressive new construction addition created a 3 car garage, 2 ''en suite bedrooms,...additional details in ''Private Remarks''.

Listed by Chris Olson of eXp Realty,LLC

MLS Number 22504804

• Residential
• Bedrooms 5
• Bathroom 4
• Square Feet 3,080
• Town Chatham

** Pinkwink, Circa 1850** - A beautifully updated antique in Chatham on 1.48 acres. Five bedrooms--four in the main house, one in the two-room guest suite above the detached two-car garage with private deck and screened in porch below. The main house features a large sunlit chef's kitchen with cathedral ceiling and top-tier appliances, wood floors, spacious dining room with fireplace, living room with fireplace, first-floor bedroom currently used as a sitting room, foyer with unique herringbone brick floor, laundry room, plus finished basement. Upstairs, the primary suite offers full bath and three closets, plus two additional bedrooms with full bath. Enjoy picturesque front and back porches, mature plantings, a stone deck, a private back yard with firepit, and space for a swimming pool or tennis court. On the Chatham walking loop, just steps to downtown, Oyster Pond, and Battlefield Landing. Don't miss this exceptional opportunity!

Listed by Timothy P Bailey and John C Ricotta of John C Ricotta & Assoc.

MLS Number 22504627

• Residential
• Bedrooms 4
• Bathroom 5
• Square Feet 2,850
• Town Chatham

Views, Views, Views!! Sun splashed Stage Harbor waterfront offering and ever-changing vista out to Nantucket Sound and beyond. This four bedroom, 4.5 bath residence blends exquisite taste with timeless coastal elegance. Thoughtfully renovated, the home is designed to showcase wide, sweeping views of the harbor from nearly every room. Light-filled interiors pair refined finishes with a relaxed Cape Cod sophistication, creating a space that feels both luxurious and inviting.A private path leads you directly to the water, with an easy town landing close by, where you can enjoy the ever-changing tides, watch boats drift by, and take in the serenity of waterfront living. With a balance of comfort and craftsmanship, this home offers an unparalleled opportunity to experience Chatham at its very best. Shown by appointment.

Listed by Barbara P Garside of eXp Realty,LLC

MLS Number 22502521

• Residential
• Bedrooms 4
• Bathroom 4
• Square Feet 3,878
• Town Chatham

BREATHTAKING SUNSETS OVER NANTUCKET SOUND. Perched above Buck's Creek with panoramic views stretching to Nantucket Sound, this extraordinary 1.3-acre Chatham property is a true waterfront sanctuary. Designed to embrace its breathtaking natural surroundings, the home features walls of glass and an expansive wraparound deck that blur the line between indoors and out. Spectacular sunsets create a daily spectacle. Spanning 3,878 sq. ft., this beautifully updated 4-bedroom, 3.5-bath home combines modern comforts with timeless coastal charm. Hardwood flooring runs throughout the main levels, complementing a light-filled kitchen at the heart of the home, flanked by two inviting living areas. The primary suite offers a serene retreat with dual walk-in closets, a private study, and a fireplace. Additional features include central A/C, natural gas heat, a whole-house generator, three fireplaces, and a two-car garage. The walkout lower level adds 950 sq. ft. of flexible living space--ideal for guests or recreation. Step outside to launch a kayak or paddleboard right from your backyard. Located in the sought-after Hardings Beach Hills, this contemporary property is one of a kind.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

MLS Number 22504396

• Residential
• Bedrooms 4
• Bathroom 6
• Square Feet 5,800
• Town Chatham

Stunning brand new construction from The Young Companies at 230 Barcliff Avenue is underway...Architecturally pleasing 4BR 6 bath shingled home will offer impeccable details , finish work and fabulous walk to town location. Enjoy walking to Chatham's summer league baseball games, iconic fish pier and exclusive Chatham Bars Inn Resort. The 5800 sf home will offer the best in new amenities with a nod to the shingled coastal cottage estates of times past.. The open interior has both a welcoming front porch as well as a screened porch. The magic continues with high ceilings, centrally located living room with fireplace that opens to well designed kitchen with center island, breakfast room, pantry and adjacent dining room. A robust primary ensuite, private den and three additional quest bedrooms grace the second floor. The lower level has two additional rooms and a full bath. Media room, playroom, gym? you decide. Two car detached garage with additional full bath and potential for a swimming pool. Early summer 2026 occupancy.

Listed by Lori L Fanning Smith of Compass Massachusetts,LLC

MLS Number 22504531

• Residential
• Bedrooms 3
• Bathroom 3
• Square Feet 2,418
• Town Chatham

Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, is a coastal masterpiece nestled in Hardings Beach Hills with panoramic views of the marsh and creek. Blending classic Cape vernacular with modern inspiration, the home is defined by extraordinary craftsmanship and architectural detail. The open main level features a curved fireplace wall with v-groove paneling that flows into the dining area, while a dramatic two-story dining room with reading loft is framed by a wall of windows. The chef's kitchen offers full amenities and casual bar seating, complemented by a versatile bedroom/study, full bath, and mudroom. The serene primary suite boasts a fireplace, built-ins, window seat, and a luminous stained-glass accent window. A guest suite with lofty ceilings completes the upper level, while the walk-out lower level provides family space, custom built-ins, abundant storage, and expansion potential. Outdoors, stonework, mature plantings, expansive decks, and a pergola patio enhance the setting. As part of the Bucks Creek Association, residents enjoy a private picnic area and dock with access to Nantucket Sound.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC