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$4,950,000
3 Beds ⋅ 4 Baths ⋅ 73570275 MLS
Situated along the peaceful shores of the Oyster Pond River, this stunning seaside home effortlessly blends classic New England architecture with modern luxury. Arriving along a gravel driveway bordered by blooming hydrangeas and mature trees, the residence makes an immediate impression with crisp white columns and a bluestone walkway. Inside, light-filled interiors showcase clean architectural lines, light wood floors, and custom built-ins. At the heart of the home lies a soaring vaulted great room anchored by a large stone fireplace, framed by double-height windows and glass French doors that capture panoramic water views.Designed for effortless entertaining and everyday comfort, the main level flows between open gathering areas and quiet retreats. The eat-in chef's kitchen features custom cabinetry and professional-grade appliances, including a Sub-Zero refrigerator, double ovens, and a Thermador range. Adjoining the kitchen, the formal dining room serves as a centerpiece for hosting, complete with built-in display shelving and a cozy window seat, illuminated by a custom glass pendant light fixture suspended from a recessed ceiling. A first-floor en suite bedroom completes the main level, providing refined accommodations for guests or family. On the second level, a light-filled den is equipped with a wet bar, a built-in alcove day bed, and a private balcony overlooking the water. The primary suite serves as a true sanctuary, complete with vaulted ceilings, expansive windows framing water views, and a contemporary fireplace. The spa-like primary bath boasts a deep soaking tub with a wood surround, a glass shower with textured wall tiling, dual-sink vanities with under-cabinet lighting, and connects to a spacious walk-in closet. The lower level offers endless possibilities with a stone fireplace, built-in workstations, additional guest space, and a fully appointed bath with a deep soaking tub. Outside, multi-tiered outdoor spaces - including covered decking, a stone patio, and manicured lawns running down toward the water's edge - offer front-row seats to Chatham's iconic maritime landscape. Whether setting off by kayak for a day on the water or enjoying al fresco entertaining amidst unsurpassed natural beauty, this property represents coastal Cape Cod living at its absolute finest.

103 Aunt Nabby's Lane, Chatham

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .
$1,695,000
2 Beds ⋅ 4 Baths ⋅ 73561031 MLS
Discover coastal living in this custom-built 2015 contemporary Cape, just 3/10 mile from Forest Beach in desirable South Chatham. Approximately 2,300 sq. ft. includes 2 spacious en-suite bedrooms with walk-in closets, 3½ baths and extra space in the finished basement with full bath. The open floor plan features 8-10' ceilings, abundant natural light, and white oak floors. The kitchen opens to the dining and living areas with a gas fireplace. Amenities include Anderson Stormwatch windows, gas heat, central air and underground utilities provide year-round comfort. The finished lower level offers a Jacuzzi bath, antique pine bar, and pool table. Quality construction includes double-dipped cedar shingles, Azak trim and decking, heavy-duty asphalt roof, and three porches (two covered). This south-facing lot offers close proximity to Nantucket Sound. Close to Forest Beach, post office, restaurants, package store, and Cape Cod Rail Trail, this beautifully crafted home offers exceptional quality, comfort and a location in one of South Chatham's most desirable neighborhoods.

43 Tobey Turtle, Chatham

Listing courtesy of Listing Agent: Timothy Bailey from Listing Office: John C. Ricotta & Associates, Inc..
$4,250,000
3 Beds ⋅ 4 Baths ⋅ 73552814 MLS
Exceptional waterfront estate offering breathtaking views from nearly every room and a private sandy beach. Lovingly owned by the same family for nearly three decades, this spectacular 3 bedroom, 3.5 bath residence offers three levels of beautifully designed living overlooking Crow's Pond. A grand foyer opens to a dramatic living room with soaring ceilings, a fireplace, walls of windows, and sweeping water views. Glass doors lead from the living room to a deck and patio overlooking the water, creating the perfect setting for entertaining or relaxing. The first floor also features a waterfront dining room, kitchen, spacious primary suite, wood-paneled den, powder room, laundry, and an attached two-car garage. A charming side porch provides yet another inviting outdoor retreat with spectacular water views. Upstairs, two guest bedrooms enjoy water views and share a full bath. The walkout lower level offers a family room, office, full bath, natural light, and excellent storage. Experience Cape Cod's finest waterfront living with boating, kayaking, swimming, and fishing right from your private sandy beach. Ideally located next to Eastward Ho! and a short drive to downtown Chatham.

600 Fox Hill Rd, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.
$2,295,000
4 Beds ⋅ 4 Baths ⋅ 73548377 MLS
Enjoy this retreat like home with two great rooms which can be used for entertaining and family gatherings, an open kitchen with large dining space, a first floor primary with en-suite bathroom including laundry. Wrap around decks taking in nature is at every turn of this unique home. This home has deeded rights to Lovers Lake perfect for swimming, kayaking and fishing. Located at the end of a quiet cul-de-sac, this home offers privacy and views of nature at every turn. and floor-to-ceiling fireplaces, a large kitchen with granite and island with seating open to a dining area, a primary suite with en-suite full bathroom with washer dryer and lots of closets, and a half bath. Upstairs is a second primary bedroom with walk-in closet, its own fireplace and sitting area, an additional bedroom, and a full bath. The walkout lower level has a bedroom with full windows, a full bath, and another washer/dryer which all leads to a stone patio with fire pit and custom built stone seating.. Close to Chatham Village, bike bath and Chatham beaches.

55 Winterset Drive, Chatham

Listing courtesy of Listing Agent: Janet Stuart from Listing Office: Coldwell Banker Realty - Concord.
$4,995,000
4 Beds ⋅ 4 Baths ⋅ 73529657 MLS
Perched on the waterfront in Chatham's coveted Stage Island neighborhood, this exceptional 4-bedroom, 4-bath coastal retreat offers 270-degree panoramic views of Stage Harbor, Nantucket Sound, and surrounding tidal marshes. Built to stringent post-Katrina standards and completed in 2011, the home showcases superior construction, reinforced structural tie-downs, and impact-rated windows. Designed to maximize its breathtaking setting, the light-filled open floor plan features walls of glass and stunning water views from nearly every room. The main level includes a spacious living room with fireplace, dining area, updated kitchen, two bedrooms, and a shared bath. Upstairs, two private en-suite bedrooms enjoy elevated harbor vistas. The walkout lower level offers a family room and fitness space overlooking the water. A 2025 kitchen renovation, 2019 revetment, direct water access for kayaking, paddleboarding, fishing, clamming, and swimming, make this an exceptional opportunity.

56 Stage Island Road, Chatham

Listing courtesy of Listing Agent: James Lowenstern from Listing Office: eXp Realty LLC.
$2,950,000
4 Beds ⋅ 4 Baths ⋅ 73511079 MLS
TURNKEY!! Just open the door to one of Chatham's most desirable neighborhoods, a timeless single-family residence, set on over 40 sq. ft. of manicured land, presents an exceptional opportunity for sophisticated coastal living. This property, maintained in great condition, embodies a refined aesthetic and functional design. The kitchen, thoughtfully designed for both culinary pursuits and social engagement, features stainless steel appliances, stone counters, and a convenient peninsula. Its open-plan configuration seamlessly connects with the living room, enhancing the flow for entertaining, and includes a built-in microwave and a high-end range. The living room serves as a central gathering space, distinguished by a fireplace that provides warmth and ambiance. Integrated built-in shelves offer both display and storage solutions, complementing the rich hardwood flooring that extends throughout. 4 bedrooms, 3.5 baths, and oversized 2 car garage with staircase to loft, a walkout finished basement complete wonderful house

60 Harbor Hill Rd, Chatham

Listing courtesy of Listing Agent: Jacqueline Casey from Listing Office: Shore Road Realty, LLC.
$4,295,000
4 Beds ⋅ 4 Baths ⋅ 73509923 MLS
This exceptional coastal retreat was designed to capture sweeping views of tidal salt marshes, natural vistas, and Nantucket Sound from nearly every room. Soaring ceilings & dramatic walls of glass fill the home with natural light and frame spectacular sunsets. Multiple sliders open to an expansive wraparound deck for effortless indoor-outdoor living. Chefs kitchen, dual living areas, and adjacent open dining create an exceptional setting for relaxing or entertaining. There's nearly 5,000 sq on three levels, with 4 bedrooms and 3.5 baths. The luxurious primary suite offers panoramic water and sunset views. A finished multi-room lower level includes family room and convenient kitchenette. Solar panels, generator, gas heat, Central A/C, outside shower, reclaimed wood floors & more. You'll enjoy a seasonal dock/catwalk on Bucks Creek for kayaking, paddle-boarding, or clamming from your own back yard - and the calm waters of Harding's Beach are a short stroll via sidewalk. Don't miss out!

38 Indian Trail, Chatham

Listing courtesy of Listing Agent: Lori Jurkowski from Listing Office: Christie's International Real Estate Atlantic Brokerage.
$4,500,000
4 Beds ⋅ 4 Baths ⋅ 73492591 MLS
Panoramic Stage Harbor views are the centerpiece of this exceptional Morris Island waterfront setting. The property offers four bedrooms and 3.5 baths, each room oriented to the scenery beyond. The residence pairs a classic seaside character with an elevated aesthetic. The main living level is bright and welcoming with a high-end kitchen, generous living room and dining area overlooking the water and doors to an expansive waterside deck. A versatile layout supports single-level living, featuring a first-floor suite currently enjoyed as a family room with a fireplace, soaring ceilings, full bath, and access to the deck. The upper level includes three bedrooms and a den, all benefiting from stunning outlooks. Professionally designed grounds provide a sense of seclusion, complemented by a private footpath to the shoreline. An exceptional offering in one of Chatham's most coveted waterfront locations.

346 Morris Island Road, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

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