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$6,990,000
5 Beds ⋅ 6 Baths ⋅ 73569424 MLS
Experience the very best of Chatham living. Few properties offer this extraordinary combination of premium waterfront living and the ability to stroll to everything the historic village center has to offer. Set behind privacy fencing and mature plantings on Oyster Pond, this distinctive home sits steps from your private boat dock and steps from vibrant downtown Chatham. Walk to your morning coffee, acclaimed restaurants, luxury boutiques, fine galleries, the historic bandstand, parades and summer baseball games. Then return home to the water, step aboard your boat, and cruise through Stage Harbor to Nantucket Sound and beyond. The private pier and dock provide coveted tidal deep-water access, while stunning water views are enjoyed from nearly every room. The four-plus one bedroom residence spans three levels of exceptional water-view living with expansive windows, generous gathering spaces, a beautiful primary suite, separate guest quartiers and a rare six-car garage. Bring your vision to masterfully renovate the existing home or design an entirely new custom masterpiece. A truly unparalleled real estate opportunity.

108 Queen Anne Road, Chatham

Listing courtesy of Listing Agent: Dawn Marie Boynton from Listing Office: .
$1,469,000
5 Beds ⋅ 10 Baths ⋅ 73548115 MLS
New co-ownership opportunity: Own one-eighth of this professionally managed, turnkey home by Pacaso. Fox Hill sits on 2.74 acres in Chatham, a renovated coastal estate with sweeping views of Crows Pond, Eastward Ho and Pleasant Bay from nearly every angle. The shingle-style exterior is substantial and classic Cape Cod, with a two-car garage and a private boat dock giving direct access to the water. The open, airy living room has a stone fireplace, window seats and vast water views throughout. The kitchen continues the view with a Wolf gas range, a large island with seating and doors opening to an expansive deck overlooking Crows Pond. The three-level layout includes a quiet office, a lower-level gym, an indoor sauna and a guest suite with its own full kitchen and living room. An elevator connects all floors. The pool, patio and private boat dock anchor Fox Hill's outdoor sequence, with sunrise and sunset views in one of Cape Cod's most storied seaside towns.

558 Fox Hill Rd, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .
$6,500,000
10 Beds ⋅ 10 Baths ⋅ 73535185 MLS
Landmark Chatham Georgian estate set on 1.3 acres overlooking Oyster Pond, with downtown and beach just moments away. Known as ''Beechwood'', this iconic residence was built in 1948 for Henry Howes, a descendant of one of Chatham's earliest families and showcases exceptional craftsmanship throughout. The stately brick main structure is flanked by two projecting wings. The home offers over 7,500 sq ft with 10 bedrooms and 10 bathrooms. Inside, enjoy hand-painted murals, sweeping water views, curved staircases, intricate woodwork, and beautifully scaled living spaces filled with character. The lower level features a ''speakeasy'', ballroom, workshop, and storage. Outside, expansive terraces, mature gardens, bluestone walkways, towering trees, and rolling lawns create a spectacular setting leading toward the water. The property was divided into three townhouse residences, but has since been used as a single-family home. A rare chance to own one of Chatham's most iconic legacy properties.

150-154 Cross Street, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.
$5,900,000
6 Beds ⋅ 8 Baths ⋅ 73533378 MLS
The newest release within a private gated enclave in South Chatham's emerging luxury corridor, 50 Sylvan Way is a bespoke custom estate minutes from the Cape's most iconic downtowns, beaches, and dining, yet removed enough to feel like a world apart. Thirteen rooms across over 6000 square feet of living space sited on 1.635 bucolic acres. A first-floor primary wing. Three-car garage. Every bedroom ensuite. An open-concept great room with soaring ceilings anchors the floor-plan, while a fully finished basement provides a complete auxiliary level for guests and entertaining — a depth of program rarely found. Outside, a pool and integrated jacuzzi anchor the aquatic experience, framed by a dramatic firewall feature and wraparound deck purpose-built for outdoor living at scale. Constructed by R.A. Martin — among the most trusted names in Chatham construction — the property offers a rare opportunity to customize finishes to suit. A singular proposition in the Chatham marketplace!

50 Sylvan Way, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .
$5,850,000
5 Beds ⋅ 6 Baths ⋅ 73495151 MLS
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.

15 Windy Hill Way, Chatham

Listing courtesy of Listing Agent: Timothy Bailey from Listing Office: John C. Ricotta & Associates, Inc..
$4,250,000
4 Beds ⋅ 6 Baths ⋅ 73493426 MLS
The location that has it all...walk to both town, fish pier, beach and baseball games... New Farmhouse being built by Morgan and Son is well underway and expecting completion by July. Enjoy Chatham from this 4BR 5.5 baths, 3980Sq foot home. All bedrooms offer specious accommodations with private baths. First floor boasts a primary suite, an inviting study, living room with vaulted ceilings large slider with views overloooking the new pool and patio area, airy chef's kitchen and dining area. A detached outer building houses a one car garage and a seperate

222 Barcliff, Chatham

Listing courtesy of Listing Agent: Lori Fanning Smith from Listing Office: Compass.
$4,500,000
6 Beds ⋅ 7 Baths ⋅ 73479712 MLS
Set within a private gated enclave in South Chatham’s emerging luxury corridor, 48 Sylvan Way is a singular estate moments from the Cape’s most iconic downtowns, beaches, and dining. Encompassing 1.63 acres with exceptional usability and recreational, the property offers rare privacy and scale in one of Chatham’s most compelling settings. Spanning 5,700 square feet across twelve rooms, this bespoke new construction residence showcases custom craftsmanship and intentional design, conceived for refined, generational living. Three distinct bedroom wings provide comfort and separation, with each bedroom generously sized and ensuite. At its heart, a breathtaking great room anchored by a custom-designed kitchen rises to 23-foot shiplap ceilings with reclaimed beams and a fireplace, while an 18-foot wall of glass opens to the heated saltwater pool and patio for seamless indoor-outdoor living. A rare offering defined by craftsmanship and presence —modern Cape Cod estate living elevated.

48 Sylvan Way, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

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