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$875,000
3 Beds ⋅ 2 Baths ⋅ 73574852 MLS
This classic Colonial-style home is set on a quiet road ending in a cul-de-sac, close to the Cape Cod Rail Trail and Nantucket Sound beaches. The welcoming first floor features a living room with a wood-burning fireplace, a spacious dining room with hardwood floors, an eat-in kitchen, a bedroom, a bath, and a convenient laundry area. An enclosed, unfinished breezeway offers the potential for a future mudroom and connects the home to an oversized two-car garage. Upstairs are two additional bedrooms, including one with a private balcony deck, along with a full bath and a comfortable sitting room w/fireplace that could also serve as a home office. Additional unfinished space above the garage and breezeway provides exciting possibilities for future living space, a guest suite, studio, or potential accessory dwelling unit, subject to applicable approvals. Highlights include hardwood floors, two fireplaces, oil heat, town water, split-system air conditioning, flexible spaces, passing Title V septic inspection report and wonderful expansion potential in a desirable South Chatham location.

31 Old Village Rd, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Compass.
$975,000
3 Beds ⋅ 2 Baths ⋅ 73570542 MLS
This special home circa 1865 was completely restored down to the studs with a long list of improvements inside and out. Everything has been done here so you can move in and enjoy the wonderful fall months ahead! A stunning new kitchen is the heart of the home, and features a Bertazonni professional range and hood, white custom cabinets, quartz countertops and center island. Relax in the adjacent family room with a cathedral ceiling, restored stained-glass windows and cozy fireplace. A separate dining room with original tin ceiling opens to a charming front porch. There are 3 bedrooms including an en-suite primary on the 2nd floor. Many of the design choices and renovations in the home reflect the period it was built, further enhancing its appeal. The blend of authentic charm with modern updates creates the perfect Chatham cottage retreat! Amenities include gorgeous wood floors, A/C, natural gas heat, on-demand hot water heater, outside shower, new stone driveway, town sewer connection & much more. The pastoral ¾ acre lot offers a beautiful expansive back yard with field that provides many options, including room for a pool or possibly detached garage. This central location provides easy access to shopping, Chatham and Harwich restaurants, and Nantucket Sound beaches. Come view the Zimri Bassett house and fall in love with this Chatham gem!

1455 Old Queen Anne Rd, Chatham

Listing courtesy of Listing Agent: Lori Jurkowski from Listing Office: Christie's International Real Estate Atlantic Brokerage.
$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.
$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: .
$1,795,000
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.
$1,175,000
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.
$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.
$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.
$1,250,000
3 Beds ⋅ 2 Baths ⋅ 73531412 MLS
Canoe and kayak on Mill Pond. Direct water front at the end of the cul-de-sac. Turn key - Fully furnished year round and off season rental histoy. Very private and peaceful setting yet conveninet to shopping, restaurants, beaches and highways. 3 Bedrooms, 2 baths. First floor master. Plenty of closet space. Walkout basement. Large deck overlooking Mill Pond. Gas fireplace instert. Gas stove. Washer and dryer. May assume summer rentals.

35 Duncan Lane, Chatham

Listing courtesy of Listing Agent: John Habeeb from Listing Office: Alliance Realty Advisors, Inc..
$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.
$829,000
3 Beds ⋅ 2 Baths ⋅ 73460325 MLS
Located in the sought after neighborhood of Countryside Estates. Sitting on a knoll this home offers gleaming hardwood floors throughout and open concept. The soaring cathedral ceilings in the kitchen and family room makes this home light and bright ! All stainless appliances are almost brand new and the oil tank has just been upgraded to double wall meeting today's regulation. There is natural gas and town water in the road, The wood burning fireplace creates ambiance when sitting in the family while relaxing with a good book or watching TV. The yard is filled with beautiful perennials that explode throughout spring and summer. The seller will install a new septic and hook up to town water.

33 Duck Marsh Ln, Chatham

Listing courtesy of Listing Agent: Darci Sequin from Listing Office: Gibson Sotheby's International Realty.
$2,800,000
3 Beds ⋅ 2 Baths ⋅ 73457238 MLS
Professional photos coming soon! Just moments from Hardings Beach, this inviting three-bedroom, two-bath home offers the perfect coastal getaway. Enjoy the benefits of a sought-after association featuring a dock, kayak storage, and a lovely picnic area overlooking the water. Take in spectacular water views and unforgettable sunsets, with private stairs leading down to the water’s edge of Bucks Creek for easy access and serene enjoyment. Inside, the home is a pleasure to show, highlighted by a wonderful sunroom that captures the light and scenery year-round. A rare opportunity to enjoy Chatham living at its best. An abutting property, 92 Indian Trail, is available for $3,200,000.

78 Indian Trail, Chatham

Listing courtesy of Listing Agent: Judith Smith from Listing Office: John C. Ricotta & Associates, Inc..
$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..
$789,000
3 Beds ⋅ 2 Baths ⋅ 73435928 MLS
Located in Chatham's Countryside neighborhood, this three-bedroom, two-bath cape-style ranch gets plenty of natural light and features a primary suite with a private bath and good closet space. Two additional bedrooms can be used for family, guests, or a home office. The living room has a brick fireplace. A one-car garage and large unfinished basement sits below the home, and the property sits on roughly ½ acre, offering space for outdoor activities or gardening. While in need of some updating, recent upgrades include Roof, Furnace, gas water heater, electrical, and it provides solid value and strong potential in a sought-after location that is close to local amenities.

49 Duck Marsh, Chatham

Listing courtesy of Listing Agent: Timothy Bailey from Listing Office: John C. Ricotta & Associates, Inc..
$3,595,000
3 Beds ⋅ 5 Baths ⋅ 73371097 MLS
NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retreat ''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 & 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 and is adjacent to the deck that overlooks conservation. 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. Finished lower-level w/9'' ceilings, a full bath, & 725 sq ft. Cedar roof, copper downspouts, generator & irrigation by well. With its prime location, its an easy walk to town & the beach.

287 Cedar St, Chatham

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

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