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$8,500
4 Beds ⋅ 3 Baths ⋅ 73575727 MLS
Off-Season Rental – 47 Aunt Deborah’s Lane, South Chatham. Enjoy the Cape in the quieter months at this spacious and beautifully furnished 3-bedroom, 3-bath home in desirable South Chatham. Offering approximately 2,019 square feet of comfortable living space, the home is located on a quiet residential lane just a short walk from Forest Beach and Nantucket Sound.The well-designed layout provides plenty of room to spread out, with multiple living areas, a bright sunroom, and three generously sized bedrooms. Sleeping accommodations include one king bed, two queen beds, two twin beds, and an additional daybed, making the home equally well suited for a family, couple, or professionals seeking additional space.Built in 2007 and thoughtfully maintained, the property offers the comfort and convenience of a newer Cape home while retaining a relaxed coastal feel. Central air conditioning, comfortable furnishings, and a fully equipped home make this an easy transition for an extended off-season stay.The South Chatham location provides convenient access to Chatham, Harwich Port, Route 28, local restaurants and shopping, while offering the opportunity to enjoy nearby beaches and the Cape without the summer crowds.Available for off-season rental from January 1st through mid-May 2027. Rental term, utilities, pets, and other terms subject to owner approval.

47 Aunt Deborah's Lane, Chatham

Listing courtesy of Listing Agent: Jared Cacciapaglia from Listing Office: Cacci Properties LLC.
$2,240,000
4 Beds ⋅ 3 Baths ⋅ 73571912 MLS
A meticulously maintained and beautifully decorated beach home awaits you in quaint village of South Chatham.Ideally situated between downtown Chatham and Harwich Port, this exceptional property offers the perfect blend of comfort, privacy, convenience and classic Cape Cod charm.Nestled near Forest Beach,Mill Creek,the Cape Cod Rail Trail, tennis court and conservation areas, this puts nature and recreation at your fingertips.The spacious home features 4 bedroomsand 3 baths providing plenty of room for family and guests. Thoughtfully designed for comfortable living and surround sound for entertaining, the home offers inviting spaces inside and out.The two car garage has been transformed into a fantastic game room complete with air hockey, ping pong and foosball-a wonderful space for kids and adults alike.Outside, the beautifullylandscaped yard and gardens are irrigated by a private well, keeping everything lush throughout the season. Three decks, one is a roof top, outdoor shower,firepit, patio creat the perfect setting for relaxing, entertaining and enjoying the warm Cape Cod evenings.The home is being offered partially furnished.

20 Circle Drive, Chatham

Listing courtesy of Listing Agent: Barbara Carroll-Horne from Listing Office: Gibson Sotheby's International Realty.
$4,000,000
5 Beds ⋅ 3 Baths ⋅ 73571777 MLS
A rare opportunity awaits high above the dunes of Hardings Beach to build the bluff house of your dreams. Nestled within the private enclave of Hall’s Bluff, this five-bedroom home boasts majestic, sweeping views of Nantucket Sound, Monomoy Island, and beyond. The sunsets are spectacular. Ownership includes deeded access to a neighborhood footpath leading directly to Harding's Beach and the Oyster River. Built in 1957, the house is in poor condition, but will be a wonderful project for the right buyer. The house is being sold as.

64 Harbor View, Chatham

Listing courtesy of Listing Agent: The Bohman Hartung Group from Listing Office: Gibson Sotheby's International Realty.
$2,600,000
3 Beds ⋅ 3 Baths ⋅ 73570905 MLS
Set on a tranquil dead-end lane in Chatham's Old Village, this 2006-built home pays homage to its 1720 predecessor, blending classic charm with modern living in one of the town's most appealing locations. Just steps from Lighthouse Beach and downtown Chatham, this remarkable property offers an exceptional opportunity for a full-time residence, summer getaway, or investment home. Designed for entertaining family and friends, the main level features a bright, open-concept living area with a cozy gas fireplace, hardwood floors, a distinct dining space, and a light-filled kitchen with a center island and pantry closet. French doors lead out to a private, beautifully landscaped fenced-in yard with a stone patio, gas fire pit, outdoor shower, and a charming shed. A main-floor primary bedroom, full bath, and cozy den or office complete this level. The upper level hosts two additional bedrooms and a full bath. The expansive lower level adds even more versatile space, including an entertainment room, a bonus space for an office or overflow guests, a half bath, and a laundry room.

10 Mill Hill Lane, Chatham

Listing courtesy of Listing Agent: The Bohman Hartung Group from Listing Office: Gibson Sotheby's International Realty.
$1,795,000
3 Beds ⋅ 3 Baths ⋅ 73569230 MLS
Steps from Cockle Cove Beach! This gorgeous, pristine 3-bedroom, 3-bathroom home offers the perfect blend of modern updates and beachside living. Located just steps from Cockle Cove Beach and right across the street from the Taylors Pond dock, this spotless property is completely move-in ready. Kitchen & Baths have been beautifully remodeled within the past few years. Walls were opened up to create a bright, seamless flow and allow winter views of Taylors Pond from the kitchen, dining area and the fire placed living room. Generous living spaces feature three distinct family areas to gather, relax, and entertain. A lower-level family room features its own full bathroom. It is the perfect escape for rainy days. Three Full Baths easily accommodate a house full of family and weekend guests. Beautiful, established gardens offer incredible curb appeal and are easy to maintain. The absolute best part of this home is where it sits. Walk right over to Cockle Cove Beach for or launch your kayak or paddle board in Taylors Pond and paddle to Nantucket Sound. Many other important updates and renovations have been completed by the current owners.

23 Taylors Pond Rd, Chatham

Listing courtesy of Listing Agent: Kathleen Phelan from Listing Office: Compass.
$1,375,000
2 Beds ⋅ 3 Baths ⋅ 73568802 MLS
One of the iconic Christopher Ryder House condominiums can be yours in time for the Fall season. This elegant two-bedroom, three-bath home blends timeless architectural character with refined two-level living. Gracious rooms, high ceilings, oversized windows, skylights, original beams, and warm wood floors create an inviting atmosphere throughout. The open floor plan features a spacious living room with gas fireplace flowing seamlessly into the dining room space and updated chef's kitchen—perfect for entertaining. A sunlit office space opens through sliding doors to a private patio, ideal for gatherings, gardening, or a peaceful outdoor retreat. The primary suite offers a walk-in closet and updated bathroom. The spacious second bedroom enjoys a nearby full hall bath, with the additional second office space providing flexibility for work or guests. Interior access to the garage, along with additional storage, adds everyday convenience. A rare opportunity to enjoy architectural charm, modern comfort, and effortless living in one exceptional home.

1114 Orleans Rd Unit 8, Chatham

Listing courtesy of Listing Agent: Betsy Hargreaves from Listing Office: Gibson Sotheby's International Realty.
$1,950,000
4 Beds ⋅ 3 Baths ⋅ 73567876 MLS
Reaching into the ocean, the road to Chatham follows a path carved by memory, a line etched straight through the geography of the heart. At 4 Williams Way, that coastal journey finds its destination. Tucked away on a five-home cul-de-sac, this 1.5 acre Contemporary Cape Cod offers sanctuary in a prime location, just minutes to downtown Chatham and 1.7 miles to Cockle Cove Beach, all while being sheltered from peak summer traffic. Spanning 2,198 interior square feet, this 4 bedroom, 2.5 bath home marries classic coastal architecture with refined single-level living. The open-concept living area is anchored by a light-filled chef's kitchen featuring a spacious quartz-clad island with seating for four. The primary bedroom suite offers dual walk-in closets and an en-suite bathroom complete with soaker tub and tiled shower. The centerpiece of the property is a dramatic and private outdoor living room. Sheltered beneath a beadboard soffit ceiling, this open-air retreat invites you to settle in with friends and family, light the logs in the Cambridge ledgestone fireplace, and play home movies on the custom inset TV. Beyond the canopy, the patio opens completely to the sky; from there, cross the lawn to the fenced vegetable garden for homegrown ingredients, or head to the detached shed to chart your next project. Back inside, the second floor hosts three additional bedrooms and a full bath. Main floor laundry is smartly located in the half bath. The attached one car garage offers walk-up storage above for seasonal gear and long-term organization. Follow your heart to Chatham and let the salt air settle—4 Williams Way is your canvas for reconnection. All parties to verify information contained herein.

4 Williams Way, Chatham

Listing courtesy of Listing Agent: Erin Terkelsen from Listing Office: LPT Realty, LLC.
$1,175,000
3 Beds ⋅ 3 Baths ⋅ 73557909 MLS
When offering please include proof of funds or pre-approval letter. Deposits may be paid via Depositlink or check payable to Compass LLC.

190 Heritage Ln, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Compass.
$8,950,000
4 Beds ⋅ 3 Baths ⋅ 73556482 MLS
The SandBox, an icon of Shore Road, sits on one of the most coveted streets in America, steps from the Chatham Bars Inn - where waterfront estates are generational and cherished. Set on an over one-acre lot with immense private beachfront, the home reflects the architectural heritage of the setting, with classic cedar shake and shingle detailing throughout. A staircase framed by flowering landscaping leads to a bluestone patio and entertaining spaces over the beach, with a private trail to the water's edge -- one of the first points on the Eastern Seaboard to greet the sunrise each morning. Inside, a shiplap-clad great room opens the home for gathering, flowing into dining and kitchen areas with water views from every angle. The primary suite is a retreat framed by its own bay window, while well-appointed guest spaces offer comfort for family and friends. Extensively renovated, the home retains the craftsmanship of its original build - true, enduring Cape Cod character. This is where summers are made. Shore Road beachfront grows more coveted with time, and opportunities like this rarely surface - a chance to secure one of the most aspirational addresses on the entire East Coast.

166 Shore Road, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .
$995,000
3 Beds ⋅ 3 Baths ⋅ 73538377 MLS
Sprawling and spacious, 65 Captain Kendrick Drive presents an exceptional opportunity to own a beautifully situated 3 br 3 bath home in one of Chatham's most peaceful settings. Seasonal views of the Monomoy River create a serene backdrop, inviting relaxing vibes and a true sense of coastal tranquility.Offering 1,754 sqft of main-level living, the home many features include an updated eat-in kitchen, large living room with fireplace, and a dining room that leads you towards two distinct, comfortable sitting areas that open to expansive decks with winter water views. 1632 sf of additional finished space in the walkout lower level add tremendous flexibility. Recent improvements include a new roof, new windows, kitchen renovations, and cooling systems. Generous living spaces, thoughtful updates, and a serene Chatham setting, make this home ready to be enjoyed for years to come.

65 Captain Kendrick Dr, Chatham

Listing courtesy of Listing Agent: Barbara Garside from Listing Office: eXp Realty LLC.
$1,899,000
3 Beds ⋅ 3 Baths ⋅ 73519558 MLS
Unique post-and-beam masterpiece, blending rustic character with modern comfort. This dramatic home showcases soaring cathedral ceilings, exposed timber framing, and an open lofted design with stained glass windows, creating an impressive sense of space and light. Rich wood details and crisp white walls create a timeless balance of warmth, craftsmanship, and coastal elegance. Thoughtfully designed for gathering, relaxing, and entertaining, this one-of-a-kind property offers the charm of a custom retreat with the functionality of today’s living. Ideally located close to beaches, shopping and restaurants. With deeded rights to the private beach just steps away, a beautiful landing to launch your kayaks. This is a truly distinctive home with architectural character, inviting spaces, and an unforgettable sense of place. (Moorings should be available on Taylor's Pond with a relatively short waitlist, check with the Harbormaster!)

70 Uncle Deane's Rd, Chatham

Listing courtesy of Listing Agent: Patrick Davison from Listing Office: .
$4,200,000
3 Beds ⋅ 3 Baths ⋅ 73515489 MLS
Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, is a coastal showpiece set in Hardings Beach Hills, with sweeping views of the marsh and creek. Blending classic Cape vernacular with modern lines, the home showcases exceptional craftsmanship and architectural detail throughout. The open main level is anchored by an arched fireplace wall that flows into a dramatic two-story dining area and reading loft, both set off by a soaring wall of windows with water views. The chef’s kitchen offers bar seating, while a versatile bedroom or study, full bath and mudroom complete the floor. The primary suite is a quiet retreat, featuring a fireplace, built-in bookshelves, a window seat and a luminous stained-glass accent window. A second guest suite with vaulted ceilings completes the upper level. The walk-out lower level provides generous family space, custom built-ins, abundant storage and room for expansion. Outdoors, mature plantings, stonework, a large deck and a pergola.

30 Indian Trail, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.
$2,850,000
3 Beds ⋅ 3 Baths ⋅ 73513527 MLS
Stage Island is among the most exclusive addresses on Cape Cod — a private enclave of fewer than 40 homes where properties rarely change hands and waterfront offerings are nearly nonexistent. When one does surface, it commands attention. This is that moment. Set on 1.07 waterfront acres, sweeping marsh and water views, breathtaking sunsets, and abundant conservation land define a setting that is truly generational. Marsh-front access invites kayaking and quiet recreation, while wildlife and natural beauty frame everyday life. The 3-bedroom, 2,200+ SF contemporary residence is thoughtfully sited and bathed in natural light, anchored by a wall of windows and doors with 270-degree views. The private primary suite offers its own deck and a soaking tub with waterfront views — an orientation that simply cannot be improved upon. Outside, gardens, patios, and decks create multiple zones for alfresco dining, yard games, and summers well spent. A setting this rare does not come twice!

336 Stage Island Rd, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .
$2,295,000
3 Beds ⋅ 3 Baths ⋅ 73477537 MLS
Gracefully sited on edge of Frost Fish Creek, a conservation estuary, this custom built 3 bed,2.5 bath Cape is the essence of Cape Cod style. Sunlit wide pine floors & fine bespoke built-ins, accentuate timeless craftsmanship. Formal living room has grand wood-burning FP, open to elegant dining room & brick floored vaulted ceiling sun/great room with gas FP & wet bar for relaxed moments overlooking koi pond& garden.The chef's kitchen has granite countertops, a generous 6 seat center island, a cooking fireplace & skylit seating area, which flows to the tranquil stone patio for outdoor dining, BBQ.1st FL primary suite with sitting room and en suite bath. Plus lower level office 300 Sq ft, 2 car garage, AC, generator, gas heat, irrigation. Seller to install new 3 BED septic & new 2nd FL heating/AC system. Adjacent Building lot 20,737 Sq ft available for sale $650,000 PIN #73528474 after the house is sold or as a package. 2026 Frost Fish Crk Restoration project for tidal flow in progress.

41 Court St, Chatham

Listing courtesy of Listing Agent: The Nickerson Power Group from Listing Office: Compass.
$3,200,000
3 Beds ⋅ 3 Baths ⋅ 73457239 MLS
Professional photos coming soon! Discover the perfect coastal retreat on Bucks Creek, where sweeping water views and breathtaking sunsets set the backdrop for everyday living.This beautifully maintained home offers 3 bedrooms, 3 baths, and a dedicated office, providing flexible space for both relaxation and productivity. Located just moments from Hardings Beach, the property enjoys a coveted setting within a friendly association that features an association dock on Bucks Creek, complete with kayak storage and a picnic area—ideal for effortless days on the water. The home is enhanced by EV charging station and owned solar, offering exceptional energy efficiency and savings. Thoughtfully designed, light-filled, and meticulously cared for, it is truly a delight to show. Come experience the charm, serenity, and coastal lifestyle this Bucks Creek gem has to offer. An abutting property, 78 Indian Trail, is availbale for sale at $2,800,000.

92 Indian Trail, Chatham

Listing courtesy of Listing Agent: Judith Smith from Listing Office: John C. Ricotta & Associates, Inc..
$5,495,000
2 Beds ⋅ 3 Baths ⋅ 73419421 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.

99 Uncle Alberts Drive Ext, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Compass.

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