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1114 Orleans Rd Unit 8, Chatham
$1,325,000
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.
43 Tobey Turtle, Chatham
$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..
71 Rowland Drive, Chatham
$1,795,000
3 Beds ⋅ 2 Baths ⋅ 73561027 MLS
Experience the ultimate waterfront lifestyle in this lovely coastal retreat. Perfectly positioned on the edge of Frost Fish Creek, this charming home captures picturesque water views and is thoughtfully designed for effortless indoor-outdoor living. Enjoy direct tidal access to one of Cape Cod's most treasured waterways. Secure a private mooring and launch your kayak, paddleboard, or boat right from your backyard. Meander through scenic Frost Fish Creek into Ryder's Cove and the sparkling waters of Pleasant Bay, where endless opportunities for boating, sailing, fishing, shellfishing, and exploring pristine beaches await. Continue beyond to discover one of New England's most spectacular estuaries and its gateway to the Atlantic Ocean. The expansive rear deck provides the perfect setting for entertaining guests or simply relaxing beneath the stars while taking in the peaceful waterfront setting and ever-changing coastal views.Buyer is responsible for the design and installation of a septic system. Septic engineering is currently underway to determine whether the property will support a two- or three-bedroom septic system.

71 Rowland Drive, Chatham

Listing courtesy of Listing Agent: Dawn Marie Boynton from Listing Office: .
55 Winterset Drive, Chatham
$2,295,000
4 Beds ⋅ 4 Baths ⋅ 73548377 MLS
Renovated and expanded Contemporary Cape at the end of a cul-de-sac on just under two acres allows for a unique amount of privacy while being less than a five minute drive to Chatham Village, Chatham Lighthouse, the Chatham Bars Inn and all that Chatham has to offer. As part of Great Hill Estates, this home has deeded rights to Lover's Lake for swimming, kayaking and canoeing. This home offers large open spaces perfect for entertaining and large gatherings. The first floor has a family room with vaulted beamed ceiling and wood burning fireplace open to a kitchen with large island and dining area, another large living room with gas fireplace open to a wraparound deck for grilling, dining and enjoying the views of nature looking out over the property. Enjoy a first floor primary with ensuite bathroom including laundry and a half bath. Upstairs are two more bedrooms, one as a second primary bedroom with sitting area and fireplace, another bedroom, and a full bath. The lower level has a bedroom, a full bath, second laundry, and walk-out access to a stone patio with custom stone seating area and a built-in gas fire-pit. Features including central a/c, hardwood floors, two car attached garage, brand new Bosch heating system and newer roof. Just steps away from the Cape Cod Rail Trail Bike Path, tennis courts, and pickleball courts. Home is being offered fully furnished.

55 Winterset Drive, Chatham

Listing courtesy of Listing Agent: Janet Stuart from Listing Office: Coldwell Banker Realty - Concord.
558 Fox Hill Rd, Chatham
$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: .
95 Cotchpinicut, Chatham
$5,900,000
4 Beds ⋅ 5 Baths ⋅ 73544856 MLS
Classic Cape Cod home on a one-acre lot on the nicest street in Chatham.... Nooks and crannies and rooms and additions in several directions in this very private location of North Chatham....Choice of three primary bedrooms with attached baths... Views over Chatham Harbor and beyond.......Beach and boating just an easy walk away. Or swim and relax in your own backyard in the heated Gunite pool...Property has been very well maintained by the current owner who has been here for over 36 years and completed a new roof, many new windows, new bedroom addition, newer family room addition and more.....All information here has not been independently verified and buyer should do his/her own due diligence by checking with their attorney, and zoning and building rules and by laws, etc....Assessment numbers subject to change with new Fiscal Year.

95 Cotchpinicut, Chatham

Listing courtesy of Listing Agent: John Burke from Listing Office: William Raveis Chatham.
409 Main St, Chatham
$2,100,000
1 Beds ⋅ 2 Baths ⋅ 73535300 MLS
Location! 409 Main Street in the heart of downtown Chatham Village offers a rare and highly desirable combination: a mixed use building with first floor commercial space with showcase windows, maximum retail exposure and heavy foot traffic along with a fully renovated spacious separate second floor of residential living. There are 5 private in-town parking spaces behind the building and is located in the coveted GB-1 zoning district that has the most versatile business-use options available. The first floor commercial space features an open floor plan with 3 large areas and 4 oversized showcase windows putting your business directly in front of passing pedestrian traffic. The second floor apartment was fully renovated in 2019 and includes one bedroom, a full bath and laundry, and an open concept kitchen and a living area with vaulted ceilings. A large mahogany deck provides excellent outdoor living space. Both floors are independent of one another with separate A/C and heat.

409 Main St, Chatham

Listing courtesy of Listing Agent: Rick Smith from Listing Office: Gibson Sotheby's International Realty.
150-154 Cross Street, Chatham
$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.
50 Sylvan Way, Chatham
$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: .
35 Duncan Lane, Chatham
$1,195,000
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..
56 Stage Island Road, Chatham
$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. Fully furnished, turn-key, move right in!

56 Stage Island Road, Chatham

Listing courtesy of Listing Agent: James Lowenstern from Listing Office: eXp Realty LLC.
70 Uncle Deane's Rd, Chatham
$1,599,000
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: .
336 Stage Island Rd, Chatham
$2,699,000
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: .
60 Harbor Hill Rd, Chatham
$2,850,000
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.
70 Judges Way, Chatham
$5,450,000
5 Beds ⋅ 5 Baths ⋅ 73506909 MLS
Experience refined coastal living in this fully renovated waterfront, water view estate on the Oyster River in Chatham. Encompassing over 4,000 sqft, this exceptional 5-bedroom, 4-1/2 bath residence blends timeless elegance & luxurious touches throughout. Soaring cathedral ceilings & thoughtfully designed custom built-ins create a sense of openness and sophistication. A first-floor primary suite offers a private retreat w/tranquil water views, private bath & walk-in-closet. Four additional water view bedrooms provide comfort and flexibility for guests. A walk-out lower level expands living space with an entertainment room and full bath. 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 PLUS deeded rights to a boat house steps away!

70 Judges Way, Chatham

Listing courtesy of Listing Agent: Lori Jurkowski from Listing Office: Christie's International Real Estate Atlantic Brokerage.
15 Windy Hill Way, Chatham
$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..
48 Sylvan Way, Chatham
$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: .
41 Court St, Chatham
$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.. 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.
33 Duck Marsh Ln, Chatham
$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. New septic and town water are installed.

33 Duck Marsh Ln, Chatham

Listing courtesy of Listing Agent: Darci Sequin from Listing Office: Gibson Sotheby's International Realty.
78 Indian Trail, Chatham
$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..
92 Indian Trail, Chatham
$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..
231 Crowell Road, Chatham
$1,650,000
1 Baths ⋅ 73258353 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

Listing courtesy of Listing Agent: Judith Smith from Listing Office: John C. Ricotta & Associates, Inc..

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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