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$4,495,000
4 Beds 4 Baths 22601752 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 and dramatic walls of glass fill the home with natural light and frame spectacular sunsets; while sliders open to an expansive wraparound deck for effortless indoor-outdoor living. A chef's kitchen, dual living areas, and an open dining space - all framed by stunning views - create an exceptional setting for entertaining. Offering nearly 5,000 sq ft across three levels, you'll enjoy four bedrooms and 3.5 baths, highlighted by a luxurious primary suite with panoramic views. Multiple living spaces provide flexibility for quiet relaxation or hosting guests. The walk-out finished lower level features several rooms plus a convenient kitchenette. A seasonal catwalk leads to Bucks Creek for kayaking, paddle-boarding, or clamming, and the calm waters of popular Harding's Beach are only a short stroll. Other notable features include reclaimed wood floors, 3 fireplaces, natural gas heat, Central A/C, generator, outdoor shower, 2-car garage, and rental history. Paradise found in one of the most coveted towns on Cape Cod!

38 Indian Trail, Chatham

$3,390,000
4 Beds 4 Baths 22601737 MLS
Tucked away in Chatham's most desirable residential enclaves, this property offers a blend of classic Cape Cod charm & refined living. Set on 40,500 sq. ft. of beautifully landscaped grounds, the home invites both quiet retreat and gracious living. Inside, rich pine floors flow throughout a lovely designed layout featuring 10 spacious rooms, including 4 bedrooms & 3.5 baths The gourmet kitchen is the heart of the home, complemented by a walk-in pantry, dining room with f/place, & multiple livings areas each enhanced with 2 additional f/places. A lovely primary bedroom en suite is matched by his/hers walk-in closets. Architectural details abound, including 2 staircases, a walkout partially finished lower level & expansion potential above the oversized 2 car garage. Perfectly positioned to enjoy the best of Chatham living, whether it's walking the iconic Chatham Loop, a short distance from the house or launching a boat from Oyster Harbor boat landing a stones throw away, for all your coastal adventures. Modern comforts include central air, whole-house generator & outdoor shower. It's more than a home-it's a lifestyle-defined by location, character, and timeless coastal elegance.

60 Harbor Hill Road, Chatham

$5,750,000
5 Beds 5 Baths 22601572 MLS
Experience refined coastal living in this fully renovated waterfront, water view estate on the Oyster River in Chatham, complete with deeded boat house! Encompassing over 4,000 square feet, this exceptional 5 Bdrm, 4-1/2 bath residence blends timeless elegance & luxurious touches throughout. Soaring cathedral ceilings and thoughtfully designed custom built-ins create a sense of openness and sophistication. A first-floor primary suite offers a private retreat with tranquil water views, private bath & walk-in-closet. Four additional water view bedrooms provide comfort and flexibility for family and guests. A walk-out lower level expands living space with an entertainment room and full bath. Features include new HVAC w/natural gas heat, Central A/C, outside shower, well-irrigation, spacious deck, yard with pool potential, and private stairs to the water. Beautifully sited on 1.83 acres of pastoral grounds, you'll enjoy over 230 feet of frontage on one of the most desirable boating waterways in Chatham, with deep water access to Nantucket Sound. This exceptional property just off the Chatham Loop offers both privacy and a picturesque natural setting only minutes to Town.

70 Judges Way, Chatham

$699,999
1 Baths 22601404 MLS
Prime Chatham Residential Potential with R20 Zoning! This unique property offers a rare opportunity to create a standalone single-family home just moments from the vibrant heart of downtown Chatham. Prospective buyers should note that the building is currently utilized as a commercial barber shop under a 1969 variance; however, it is situated in the R20 residential zone. This provides a compelling path for conversion: by petitioning the Zoning Board of Appeals (ZBA) to lift the existing variance, a new owner could return the property to its residential roots as a charming coastal cottage or private pied-a-terre.The 600-square-foot building sits on a prominent corner lot on Route 28 with dedicated front and rear parking. It is fully equipped with town water and sewer (rated for 550 GPD), natural gas heat, and a 2020 mini-split for cooling. The interior already features a sink and laundry area, offering a head start on a residential floor plan. While any change of use from ''Personal and Household Services'' requires formal ZBA approval, the R20 zoning makes this a high-potential project for a custom home. Shown by appointment only.

1772 Main Street, Chatham

$12,999,900
4 Beds 7 Baths 22601380 MLS
In one of Chatham's most storied and visually captivating settings, adjacent to the iconic Mitchell River wooden drawbridge, this extraordinary waterfront estate--masterfully crafted by the renowned Eastward Companies--represents a rare convergence of architectural distinction, coastal heritage, and modern luxury. Spanning more than 6,200 square feet across three impeccably designed levels, the residence is a study in refined elegance and thoughtful scale. Every detail has been curated for a sense of timeless sophistication while embracing the natural beauty of its surroundings. The main level unfolds with effortless grace, where a grand open-concept kitchen and great room--anchored by one of four gas fireplaces--serves as the heart of the home. A formal dining room, butler's pantry, and coffee bar create an environment equally suited for intimate gatherings and elevated entertaining. Bathed in natural light, the breakfast room offers serene views over the resort-caliber outdoor setting, where a 16' x 36' Gunite pool with integrated spa and sun shelf, is set against the tranquil backdrop of the Mitchell River. The first-floor primary suite is a private sanctuary, appointed with a a spa-quality bath featuring radiant heated floors, a soaking tub, and a glass-enclosed shower. The upper level reveals a dramatic loft retreat with fireplace, wet bar, and private deck--an ideal vantage point to take in sweeping water views. A second primary suite, equally refined, is complemented by two additional guest bedrooms and baths. Above the garage, a substantial bonus room with its own deck captures panoramic vistas of Stage Harbor and the historic Chatham Coast Guard Boathouse. This home is further distinguished by its exceptional level of finish and infrastructure, including Wolf appliances, curated fixtures, central vacuum, whole-house generator, 400-amp electrical service, and professionally landscaped grounds supported by a private irrigation well. An outdoor shower completes the effortless indoor-outdoor lifestyle. A singular offering of enduring quality and provenance--this is more than a home; it's a legacy property in one of Cape Cod's most treasured waterfront settings.

157 Bridge Street, Chatham

$4,995,000
5 Beds 5 Baths 22601118 MLS
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.

101 Morris Island Road, Chatham

$5,850,000
5 Beds 6 Baths 22601111 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

$4,500,000
4 Beds 4 Baths 22601006 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

$1,399,000
3 Beds 2 Baths 22600988 MLS
Perfectly positioned on a corner lot in a quiet neighborhood, this beautifully maintained home offers peaceful living just moments from everything Chatham has to offer. Located less than a mile from downtown, it provides easy access to shops, restaurants, beaches, and landmarks including the Fish Pier, Veterans Field, Seaside Links, and Chatham Bars Inn. Offering two levels with 2,448 sqft (1,530 sqft finished), the home has been meticulously maintained, with updates including a new roof, central A/C, outdoor shower, renovated primary bath, updated appliances, and more. The main level features a bright living room with a wood-burning fireplace and bay window, an updated kitchen with breakfast bar, and a dining area ideal for entertaining. A spacious primary suite with an updated bath, along with two guest bedrooms and a full bath, complete the level. The lower level adds flexibility with a second living area, bonus bunk room, garage, laundry, and additional storage. Outside, enjoy a lush lawn, large patio, new outdoor shower, and new walkway. With a strong 15+ year rental history, this home is equally well suited as a year-round residence, seasonal retreat, or investment property.

137 Shane Drive, Chatham

$699,999
22600731 MLS
IMMEDIATE RENTAL INCOME OPPORTUNITY! Secure a high-visibility commercial asset with an established, successful tenant already in place. This prime Route 28 corner lot serves as a gateway to downtown Chatham and features a well-maintained 600 sq. ft. building currently operating as ''Next Level Barber Shop'' equipped with four chairs. This offering is ideal for an investor seeking a turn-key property with a stable nine-year business history. The site includes eight dedicated parking spaces, town water, and a public sewer connection rated for 550 GPD. Modern infrastructure includes natural gas, forced hot air, and a 2020 mini-split for summer cooling. The interior features a convenient on-site laundry/kitchen area with a sink located just inside the rear door. While currently permitted for ''Personal and Household Services'', the R20 zoning offers significant long-term flexibility. This is a rare opportunity to own a standalone footprint in one of the Cape's most desirable destinations with immediate rental income and a proven track record of success. Shown by appointment only. Buyer to verify all information contained herein.

1772 Main Street, Chatham

$4,499,900
3 Beds 7 Baths 22600794 MLS
A distinguished new residence by Eastward Companies, this exceptional home seamlessly blends timeless architecture with modern luxury, all within walking distance to Chatham Village, Oyster Pond, and renowned dining. Thoughtfully designed and impeccably crafted, the home spans over 5,800 square feet across three finished levels. The main level offers an elegant yet inviting floor plan, featuring a chef's kitchen with a butler's pantry, a formal dining room, and a sunlit breakfast nook. The great room is anchored by a gas fireplace, custom built-ins, and striking beamed ceilings, creating a warm and sophisticated gathering space. A first-floor primary suite provides a private retreat, complete with a walk-in closet and its own gas fireplace. Upstairs, two en-suite bedrooms offer comfort and privacy, including a separate suite above the garage and another with a private balcony. A versatile loft with a full bath adds additional living flexibility. The finished lower level is designed for entertaining, featuring a wet bar and full bath. Outdoors, the property is equally impressive with a heated Gunite pool and spa, professionally landscaped grounds with irrigation, and an outdoor shower--perfect for embracing the Cape Cod lifestyle. Additional amenities include a two-car garage, central vacuum, alarm system, and town sewer connection. A rare opportunity to own new construction of this caliber in one of Chatham's most desirable in-town locations.

33 Crowell Road, Chatham

$4,900,000
5 Beds 5 Baths 22600293 MLS
Located in Chatham's Quitnesset neighborhood on Morris Island, ideally situated between the Association's private deeded beach and the trails of the protected Monomoy National Wildlife Refuge, this elegant and spacious home embodies the quintessential Cape Cod lifestyle. Step into the sunlit foyer leading to a soaring great room with a fireplace and a chef's kitchen designed for entertaining. Enjoy casual meals in the breakfast room overlooking the expansive backyard or host formal gatherings in the dining room. The first-floor primary suite features a walk-in closet and private bath, while the octagonal sunroom and wood-paneled family room with a second fireplace offer peaceful retreats. Upstairs are four bedrooms, 3 full baths (2 ensuite) and a charming hideaway accessed by a spiral staircase. A back staircase off the mudroom leads to a large bonus room with expansion potential, while the basement with a full bath offers endless possibilities. Outside, enjoy the privacy of a large deck and yard to expand summer entertaining. With deeded beach rights, protected nature trails and proximity to downtown Chatham this home is a rare Cape Cod gem.

169 Tisquantum Road, Chatham

$2,700,000
3 Beds 2 Baths 22505704 MLS
Discover the charm of coastal living just moments from Hardings Beach. This inviting 3-bedroom, 2-bath home enjoys beautiful water views over Bucks Creek and spectacular west-facing sunsets. Private stairs lead directly to the water's edge, making it easy to launch a kayak, explore the creek, or simply relax by the shore. The light-filled sunroom provides the perfect place to unwind while taking in the ever-changing coastal scenery throughout the seasons. Residents enjoy access to the Hardings Beach Hills Association dock, kayak storage, and waterfront picnic area, offering exceptional opportunities to enjoy life on the water. Whether you're seeking a year-round residence, seasonal retreat, or investment opportunity, this home offers an exceptional Chatham location surrounded by natural beauty. Abutting property at 92 Indian Trail is also available for $3,200,000.

78 Indian Trail, Chatham

$3,100,000
3 Beds 3 Baths 22505703 MLS
Wake each morning to sparkling water views and end your day with spectacular sunsets over Bucks Creek. Located in Chatham's coveted Hardings Beach Hills neighborhood, this thoughtfully updated and meticulously maintained 3-bedroom, 3-bath home captures sweeping westerly water views. The primary suite features a private balcony overlooking the water, while a dedicated office offers flexibility for remote work or guests. Set on a private .40-acre lot with a classic Cape Cod outdoor shower, the property also includes owned solar panels and an EV charging station. Just moments from Hardings Beach, one of Chatham's premier family-friendly beaches, you'll enjoy easy access to Nantucket Sound. The neighborhood association offers a dock with kayak storage and a waterfront picnic area for exploring Bucks Creek. A rare opportunity to enjoy stunning views, unforgettable sunsets, modern energy-efficient features, and the relaxed coastal lifestyle in one of Chatham's most sought-after neighborhoods. Abutting property at 78 Indian Trail is also available for $2,800,000.

92 Indian Trail, Chatham

$475,000
2 Beds 1 Baths 22504973 MLS
Tucked away on a quiet street in the heart of North Chatham, this second-floor condominium offers a rare opportunity to own in one of Cape Cod's most coveted locations. Perfect as a seasonal retreat, investment property, or smart entry into the Chatham market, it blends convenience and charm. Sunlight fills the welcoming interior, highlighting hardwood floors, a cozy wood-burning fireplace, and an updated kitchen and bath with granite counters. Enjoy morning coffee by the oversized picture window overlooking a tranquil setting alive with birds and butterflies. A small shared balcony adds fresh air, while private laundry and basement storage enhance ease of living. Ideally situated within walking distance to coffee shops, restaurants, and the village, this is effortless Cape Cod living. The property offers immediate income potential and long-term lifestyle appeal--an exceptional chance to secure your place in Chatham.

109 Misty Meadow Lane, Chatham

$5,495,000
2 Beds 3 Baths 22503829 MLS
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.

99 Uncle Alberts Drive Ext, Chatham

$3,595,000
3 Beds 5 Baths 22502029 MLS
NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retreat nestled ''On the Loop'' in Chatham. This elegant residence showcases exceptional craftsmanship & luxurious finishes, making it a true masterpiece of coastal living. The gourmet kitchen w/Quartz countertops is a chef's dream, featuring top-of-the-line Subzero, Miele, and Wolf appliances. The center island w/walnut top offers space for casual dining and flows to the dining area. The nearby butler's pantry enjoys a Subzero beverage fridge. The inviting living area w/gas fireplace opens to a 3-season porch which extends your living space and is adjacent to the deck that overlooks a pristine conservation area. The 1st story primary suite boasts an ensuite bath w/radiant floor heat & walk-in closet. The 2nd story features 2 en-suite bedrooms, family room & home office. The finished lower-level w/9'' ceilings, a full bath, & 725 sq ft of living space. Features include custom woodwork, 1st floor laundry, irrigation by well, dual fuel gas hydro air hvac w/heat pump to maximize efficiency, generator & 1-car garage. With its prime location, you can easily walk to town, a nearby beach & boat mooring.

287 Cedar Street, Chatham

$1,650,000
1 Baths 22403062 MLS
Zoned Gb3, this great commercial, multi-use property consists of 2 buildings. The first building built in1995 has 948 sf with a multi-use space, an office and full bath. There is a Viessman heating and hot water system and the full basement is waiting to be finished. The second building has1,638 sf built in 2003 with 2 bays and a carport . One bay has a gas heater and the second floor is ready to be finished. Lots of possibilities - documents attached include Gb3 standard permitted uses section 3.4 and Appendix 1 ''Schedule of Use Regulations'', floor plans, and septic site plan. Great opportunities-previously a builders work shop and warehouse for storing automobiles, boats, vintage motorcycles etc. The solar panels are owned. Please verify all information contained herein. Don't miss this special property!

231 Crowell Road, Chatham

$1,650,000
22402924 MLS
Zoned Gb3, this great commercial, multi-use property consists of 2 buildings. The first building built in1995 has 948 sf with a multi-use space, an office and full bath. There is a Viessman heating and hot water system and the full basement is waiting to be finished. The second building has1,638 sf built in 2003 with 2 bays and a carport. One bay has a gas heater and the second floor is ready to be finished. Lots of possibilities - documents attached include Gb3 standard permitted uses section 3.4 and Appendix 1 ''Schedule of Use Regulations'', floor plans, and septic site plan. Great opportunities-previously a builders work shop and warehouse for storing automobiles, boats, vintage motorcycles etc. The solar panels are owned. Please verify all information contained herein. Don't miss this special property!

231 Crowell Road, Chatham

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