Homes for Sale in 02633

/6
$250,000
- Land
- 0.72 Acre
- $347,222 per Acre
0 George Ryder Rd Unit 73104629, Chatham, MA 02633

Amazing opportunity to build your dream home in Chatham on this .72-acre, panhandle, private residential lot. Build a 3-bedroom home connected to town sewer, 4-bedroom with approval. (buyer's & buyer's agents verify with Board of Health). The water, gas, electric, cable and sewer are on George Ryder Road. This property is convenient to shopping, seven restaurants, the bike path, a medical office,

Shane Masaschi

Compass

(508) 691-8324

0 George Ryder Rd Unit 73104629, Chatham, MA 02633
/52
$8,500,000
- 7 Beds
- 6.5 Baths
- 6,521 Sq Ft
44 Buena Vista Rd, Chatham, MA 02633

Chatham Waterfront Masterpiece. A private estate on Cape Cod's most coveted coastline in one of New England's most prestigious coastal communities. 44 Buena Vista Road is an extraordinary waterfront estate, a rare offering blending timeless elegance with resort-style amenities. Designed for both grand entertaining and intimate family living, this residence offers sweeping ocean views,

Shane Masaschi

Compass

(508) 400-2035

44 Buena Vista Rd, Chatham, MA 02633
/50
$975,000
- 2 Beds
- 2 Baths
- 1,340 Sq Ft
67 A Leonard Way, Chatham, MA 02633

Welcome to 67 A Leonard Way, a charming ranch-style 2-bedroom home tucked away on a quiet street just minutes from downtown Chatham. Inside you'll find a beautifully renovated kitchen with granite countertops, stainless steel appliances and custom cabinetry. The open living and dining areas feature a fireplace, built-in shelving, and hardwood floors, creating a warm and inviting atmosphere. With

Shane Masaschi

Compass

(508) 276-7761

67 A Leonard Way, Chatham, MA 02633
/74
$4,395,000
- 3 Beds
- 4.5 Baths
- 3,640 Sq Ft
287 Cedar St, Chatham, MA 02633

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

Shane Masaschi

Compass

(508) 290-5337

287 Cedar St, Chatham, MA 02633
/39
$1,700,000
- 3 Beds
- 2 Baths
- 2,008 Sq Ft
9 Bettys Path, Chatham, MA 02633

Welcome to 9 Bettys Path, your private hideaway w/panoramic views of nature's finest artwork! This charming 3-bed, 2-bath home is nestled on a 1.8-acre lot, complete with a stunning kettle pond and a lush pastoral backdrop. Renovated in 2014, the home boasts a fresh roof and all the modern comforts. Step inside to find an inviting living room with a cozy fireplace, a dining room that opens onto a

Shane Masaschi

Compass

(508) 682-4461

9 Bettys Path, Chatham, MA 02633
/67
$4,950,000
- 4 Beds
- 5.5 Baths
- 5,372 Sq Ft
335 Stage Island Rd, Chatham, MA 02633

Family-friendly home on Chatham's private Stage Island boasts captivating barrier beach and ocean views. This 10-room, 4-BR, 5.5-bath shingle-style home has 5,372 sf of living space designed for entertaining, indoors and out. The bright and airy 1st floor features a spacious great room with towering windows, a coffered ceiling, and Rumford fireplace. The kitchen boasts top-of-the-line appliances,

Jack Bohman Gibson Sotheby's International Realty

335 Stage Island Rd, Chatham, MA 02633
/76
$4,345,000 Open Sat 11AM - 1PM
- 4 Beds
- 5.5 Baths
- 4,908 Sq Ft
45 Meadow View Rd S, Chatham, MA 02633

New construction and a deeded boat slip in the Oyster River Hills private neighborhood marina. Another magnificent home by Sears Point Residential, move-in ready. 4 BR, 5.5 Bath, 4,908 sf classic shingle-style Cape. The home's axis is a chef's kitchen featuring Thermador appliances and a large center island with Quartz countertops. The open floor plan flows seamlessly from the living room to the

Jack Bohman Gibson Sotheby's International Realty

45 Meadow View Rd S, Chatham, MA 02633
/16
$7,950,000
- 4 Beds
- 4.5 Baths
- 4,020 Sq Ft
169 Shore Rd, Chatham, MA 02633

Steps from the iconic Chatham Bars Inn, this extraordinary coastal residence has been reenvisioned to offer the perfect blend of timeless seaside character and modern sophistication. The result of a visionary collaboration between Turntide Development and Schneeberger Collective, this luxurious home has undergone a full-scale transformation under the direction of architect Leslie Schneeberger.

Chris Rhinesmith Compass Massachusetts, LLC

169 Shore Rd, Chatham, MA 02633
/25
$3,795,000
- 4 Beds
- 4 Baths
- 3,030 Sq Ft
17 Bucks Ln, Chatham, MA 02633

This Chatham Beach House is calling...hope you answer.... Picture perfect Cape Cod style home with divine views over Nantucket Sound offers the idyllic Chatham beach lifestyle you have been dreaming of.....Steps to the private association beach of Harding's Shores for uncrowded enjoyment and warm water swimming. Classic 4BR 4 bath Cape home with two large decks for al fresco dining or morning

Lori Fanning Smith Compass Massachusetts, LLC

17 Bucks Ln, Chatham, MA 02633
/76
$3,295,000
- 3 Beds
- 3.5 Baths
- 3,014 Sq Ft
7 Squanto Dr, Chatham, MA 02633

This Nantucket-style home features extraordinary views across a tidal salt marsh, Oyster Pond, and the 3 church steeples in Town. Enjoy the fireworks display New Year's Eve, ever-changing beauty of the seasons, and a host of wildlife from this elevated .69 acre site. With just over 3,000 square feet this exceptionally-crafted home is the perfect size; with an open floor plan ideal for

Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

7 Squanto Dr, Chatham, MA 02633
/60
$7,299,000
- 4 Beds
- 5 Baths
- 4,214 Sq Ft
12 Pond St, Chatham, MA 02633

Custom Home in Chatham Village. 4-bedroom, 5-bathroom residence located steps from Oyster Pond and its sandy beach. This thoughtful home offers open floor plan, high ceilings, hardwood floors and expansive water views. Deeded access to an association dock and mooring field for boating enthusiasts. The gourmet kitchen features stone countertops, large center island with seating, and premium

Tim Bailey John C Ricotta & Assoc.

12 Pond St, Chatham, MA 02633
/49
$3,650,000
- 3 Beds
- 4.5 Baths
- 4,361 Sq Ft
86 Champlain Rd, Chatham, MA 02633

Hidden gem on Chatham's historic Loop with views of Stage Harbor, the Stage Harbor Lighthouse and Nantucket Sound. Savor the warm summer breezes from this 3 BR, 4.5 Bath, 4,361 sf home with a private deeded footpath to the sandy shores of Stage Harbor. Thoughtfully designed to capture harbor and wetland views, the house features vaulted ceilings, an abundance of windows, hardwood floors and an

Jack Bohman Gibson Sotheby's International Realty

86 Champlain Rd, Chatham, MA 02633
/44
$4,950,000
- 4 Beds
- 3.5 Baths
- 3,878 Sq Ft
38 Indian Trail, Chatham, MA 02633

BREATHTAKING SUNSETS OVER NANTUCKET SOUND. Perched above Buck's Creek with panoramic views stretching to Nantucket Sound, this extraordinary 1.3-acre Chatham property is a true waterfront sanctuary. Designed to embrace its breathtaking natural surroundings, the home features walls of glass and an expansive wraparound deck that blur the line between indoors and out. Spectacular sunsets create a

Chris Rhinesmith Compass Massachusetts, LLC

38 Indian Trail, Chatham, MA 02633
/53
$3,750,000
- 5 Beds
- 3.5 Baths
- 2,659 Sq Ft
92 Barcliff Ave, Chatham, MA 02633

Honored with the prestigious 2004 Chatham Preservation Award, this iconic historical residence was meticulously restored to perfection in 2002, seamlessly blending its storied heritage with the finest modern luxuries. Nestled in a prime yet private locale, the home's enchanting exterior teases with a glimpse of the lush, secluded garden, a serene oasis framed by a stately pergola. The

Chris Rhinesmith Compass Massachusetts, LLC

92 Barcliff Ave, Chatham, MA 02633
/93
$6,750,000
- 5 Beds
- 5.5 Baths
- 5,620 Sq Ft
15 Windy Hill Way, Chatham, MA 02633

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

Tim Bailey John C Ricotta & Assoc.

15 Windy Hill Way, Chatham, MA 02633
/43
$4,200,000
- 6 Beds
- 4 Baths
- 3,808 Sq Ft
150 Barcliff Ave, Chatham, MA 02633

Chatham: where hydrangeas meet the sea and harbors merge into the ocean. A place where cherished memories are created and passed on through generations. If you've been dreaming of living in this storybook town, just a short stroll from sandy beaches and its vibrant Village, you've arrived. Welcome to 150 Barcliff Avenue. Tucked along one of Chatham's most picturesque streets, this updated home

Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

150 Barcliff Ave, Chatham, MA 02633
/41
$2,699,000
- 4 Beds
- 3.5 Baths
- 3,834 Sq Ft
106 Stage Neck Rd, Chatham, MA 02633

Nestled on just over an acre of meticulously landscaped grounds with a private well for irrigation near the Oyster River, this 4-bedroom, 3.5-bath home offers a rare opportunity to create your dream space. With deeded access to a small, shared boathouse, it provides a serene and sophisticated lifestyle. Built in 1987 and lovingly cared for, the home retains its classic charm and is ready for your

Jen Graham Christie's International Real Estate Atlantic Brokerage

106 Stage Neck Rd, Chatham, MA 02633
/63
$3,495,000
- 4 Beds
- 3.5 Baths
- 4,857 Sq Ft
36 Moonbeam Ln, Chatham, MA 02633

This expansive Cape with timeless curb appeal is located in an exclusive Chatham neighborhood, and includes deeded rights to the Oyster Pond River. Immaculate and lightly used, you'll find 4,857 square feet of comfortable, casual elegance in a thoughtfully-designed floor plan. There are 4 spacious bedrooms including a lovely first-floor primary En-suite. Bright granite & stainless kitchen opens

Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

36 Moonbeam Ln, Chatham, MA 02633
/40
$2,995,000 Open Sun 11AM - 1PM
- 4 Beds
- 4.5 Baths
- 3,603 Sq Ft
290 Old Comers Rd, Chatham, MA 02633

''On Pink Wink Pond'' embodies the essence of Cape Cod. A startling entrance of Belgian blocks with carriage lighted and stone pillars greets the visitor. Ascending the farmers porch and upon entry, an illuminated tile mural of Pink Wink Pond boasts the home's attention to artistic detail. The two-story windowed great room is surrounded by crystal blue shiplap and offers a gas fireplace. Sub-Zero

Catherine Baran Berkshire Hathaway HomeServices Robert Paul Properties

290 Old Comers Rd, Chatham, MA 02633
/44
$1,100,000 Open Sat 11AM - 12:30PM
- 2 Beds
- 2 Baths
- 1,504 Sq Ft
24 Chickadee Ln, Chatham, MA 02633

Nature-lovers! A beautifully renovated post 'n beam home perched above the Monomoy River with peeks of the water from the main bedroom, screened porch, and huge patio! Completely updated in '23/'24 with new exterior sheathing, siding, windows, doors, and refinished wood floors. The kitchen boasts new cabinetry, counters, and SS appliances. The bathrooms feature new tile floors, vanities, toilets,

Amy Harbeck Kinlin Grover Compass

24 Chickadee Ln, Chatham, MA 02633
/52
$8,500,000
- 5 Beds
- 4.5 Baths
- 4,305 Sq Ft
30 Tisquantum Rd, Chatham, MA 02633

The first stop of the east wind and the morning sunrise , this elegant Cape Cod home offers an unparalleled living experience with sweeping views over the Atlantic Ocean, Stage Harbor and an enchanting salt marsh that leads to Nantucket Sound. This 5BR ,4.5 bath expanded shingled home offers a luxurious yet comfortable coastal lifestyle incorporating classic Cape Cod architectural styles with

Lori Fanning Smith Compass Massachusetts, LLC

30 Tisquantum Rd, Chatham, MA 02633
/13
$2,375,000
- Land
- 0.57 Acre
- $4,166,667 per Acre
98 Horizon Dr, Chatham, MA 02633

New construction well underway with deeded rights to Lover's Lake for swimming, fishing and boating! Classic Cape Cod home sited high on a knoll with over 3000 s.f. spanning three levels with 3 BR's and 4.5 baths. Open floor plan offers great room with vaulted ceilings, fireplace and adjacent kitchen with center breakfast island and high end appliances .First floor primary suite with full bath

Lori Fanning Smith Compass

98 Horizon Dr, Chatham, MA 02633
/14
$1,000,000
- Land
- 0.16 Acre
- $6,250,000 per Acre
723 Main St, Chatham, MA 02633

Town of Chatham officially assigned new street address 723 MAIN STREET! Take advantage of this last opportunity to build on a vacant lot on Main Street in downtown Chatham! This lot is 7,010 square feet (0.16 acres) located across from Chatham Veterans Field, home of the Chatham Anglers baseball team. This truly is the last opportunity to build on a vacant lot in downtown Chatham. For those who

Matthew Burger Kinlin Grover Compass

723 Main St, Chatham, MA 02633
/95
$2,150,000
- 4 Beds
- 4.5 Baths
- 3,902 Sq Ft
2016 Main St, Chatham, MA 02633

Stunning Magazine-Quality Home with Resort-Style Living on Main StreetTucked privately off Main Street, this breathtaking home offers the perfect balance of privacy and prime location. Designed for both relaxed living and stylish entertaining, the interior boasts an open floor plan with beautiful shiplap walls, a dedicated dining room with built-in wet bar, and a thoughtfully placed half bath

Daneen Law Gibson Sotheby's International Realty

2016 Main St, Chatham, MA 02633
/32
$11,900,000
- 7 Beds
- 9 Baths
- 6,276 Sq Ft
108 Shore Rd, Chatham, MA 02633

Located along Chatham’s transcendent shoreline, this elegant coastal estate includes a Main House, a Guest House with a 3 car garage, and a waterfront Boat House/Cabana. Surrounded by beautiful hardscape, the Colonial style Main Residence has been rebuilt with a modern, open floor plan designed for entertaining. Spectacular views of Chatham Harbor and the Atlantic abound. The Main House features

Frank Denauw Frank G. Denauw, Esq.

108 Shore Rd, Chatham, MA 02633
/2
$659,000
- Land
- 1.01 Acres
- $652,475 per Acre
1761 Main St, Chatham, MA 02633

Nestled in the picturesque town of Chatham, expansive one-acre lot presents a rare opportunity to craft your dream home in a serene setting. Backing up to a tranquil cranberry bog, this unique property offers privacy and natural beauty, providing an idyllic backdrop for your future residence.With ample space and potential, this versatile lot may accommodate two homes, making it perfect for those

Kimberly Clark Bayside Realty Consultants

1761 Main St, Chatham, MA 02633
/45
$1,399,500
- 2 Beds
- 3 Baths
- 1,861 Sq Ft
116 Happy Valley Rd, Chatham, MA 02633

Located off a private way to Ridgevale Beach overlooking a majestic cranberry bog sits this cozy colonial paradise. Built in 2015 by an award winning design/build company is this very private getaway. 1st level open plan features brk bar & dining/living area with views to the bog pond. Door to south facing deck setup for dining & and all day sun. 2 entry kitchen with granite counters & stainless

Ward Brown William Raveis Real Estate & Home Services

116 Happy Valley Rd, Chatham, MA 02633
/40
$1,475,000
- 3 Beds
- 3.5 Baths
- 2,225 Sq Ft
355 Training Field Rd, Chatham, MA 02633

Just 8/10 of a mile to Jackknife Point BeachThis beautifully appointed Chatham retreat offers the perfect blend of comfort, style, and solar efficiency. A charming farmer’s porch welcomes you into a light-filled home with high ceilings, an open layout, and a skylit kitchen with granite counters, stainless steel appliances, and a large island. The living room features a cozy gas fireplace, and the

Margaret McDonald Mathieu Newton Sotheby's International Realty

355 Training Field Rd, Chatham, MA 02633
/32
$5,900,000
- 4 Beds
- 4.5 Baths
- 4,654 Sq Ft
25 Wikis Way, Chatham, MA 02633

TIMELESS COASTAL LUXURY // Prepare to be embraced by one of the most breathtaking panoramas in all of Cape Cod. This exceptional property offers sweeping and unobstructed views that stretch from Stage Harbor and the iconic Chatham Lighthouse, to the natural beauty of Monomoy Island and the sparkling expanse of the Atlantic Ocean. From first light until sunset, this coastal retreat is surrounded

Chris Rhinesmith Compass Massachusetts, LLC

25 Wikis Way, Chatham, MA 02633
/28
$1,300,000
- 3 Beds
- 3 Baths
- 2,202 Sq Ft
319 Riverview Dr, Chatham, MA 02633

Sited on nearly an acre of land in Riverbay Estates, this spacious three bedroom, three bath home offers ample privacy and outdoor living space.Built in 1984 with an addition and updates in 2004, the home is designed with flexibility for one floor living with a generous sized first level primary suite withgas fireplace, walk in closet, and outdoor access. The kitchen features abundant cabinet

Chris Rhinesmith Compass

319 Riverview Dr, Chatham, MA 02633
/68
$2,445,000 Open Sat 12PM - 3PM
- 4 Beds
- 3.5 Baths
- 4,072 Sq Ft
55 Winterset Dr, Chatham, MA 02633

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick

Tara Schiffmann Brown Bayview Real Estate

55 Winterset Dr, Chatham, MA 02633
/29
$2,300,000
- 3 Beds
- 4.5 Baths
- 1,834 Sq Ft
292 Stage Harbor Rd, Chatham, MA 02633

Approximately a half mile to either Oyster Pond Beach or Stage Harbor and 3/4 of a mile to the center of Chatham Village sits this exceptional 3 bedroom 4 bath custom Farmhouse with inviting front porch built in 2018. Hardwood floors thruout and, formal dining area, custom kitchen along with an office for those working remotely. Home has central a/c and a gas stove in the Livingroom. The lower

Ward Brown William Raveis Real Estate & Home Services

292 Stage Harbor Rd, Chatham, MA 02633
/30
$2,300,000
- 4 Beds
- 2 Baths
- 1,238 Sq Ft
213 Main St, Chatham, MA 02633

Location! Location in the heart of Chatham! Historic Greek Revival circa 1850's in the Old Village, with water views of Chatham Harbor, Andrew Harding's landing and Lighthouse beach & Main St shopping/dining, Band Concerts, nearby! This charming 4 bed/2 bath home has a sunny eat-in beamed family room with sliders to deck, cozy kitchen adjacent and a front Living room with gas fireplace, warm

Phyllis Power Compass

213 Main St, Chatham, MA 02633
/39
$1,649,000
- 3 Beds
- 2.5 Baths
- 2,340 Sq Ft
307 Riverview Dr, Chatham, MA 02633

Discover luxury & comfort in this stunning Riverbay home nestled with beautiful landscaping on Riverview Drive. This meticulously renovated 7 room ranch offers 2340 Sq. ft of elegant living space, featuring 3 spacious bedrooms, 2.5 luxurious tiled baths with double vanities. As you step inside, the inviting foyer introduces you to the warmth of a formal living room with fireplace, open plan to

Phyllis Power Compass

307 Riverview Dr, Chatham, MA 02633
/21
$995,000
- 3 Beds
- 2 Baths
- 1,726 Sq Ft
144 Lakeview Ave, Chatham, MA 02633

Three bedroom ranch house with two car garage in desirable Riverbay Estates. All bedrooms on the first floor for easy living. Great neighborhood for swimming, walking, bike riding, kayaking, and fishing at the two private association ponds and the Monomoy River.... Close to Pleasant Bay and School House Pond beaches. Something for everyone in this very private area...Brokers and buyers are

John Burke William Raveis Chatham

144 Lakeview Ave, Chatham, MA 02633
/46
$4,600,000
- 3 Beds
- 3.5 Baths
- 2,998 Sq Ft
85 Main St, Chatham, MA 02633

OFFERED FULLY FURNISHED INCLUDING ALL CONTENTS SO YOU CAN MOVE RIGHT IN! // Ideally situated in one of Chatham's most sought-after enclaves, just steps from iconic Lighthouse Beach, this exceptional home is rich in character and timeless charm. Beautifully maintained, it offers sun-filled, spacious interiors that transition seamlessly between formal elegance and casual comfort.The thoughtfully

Chris Rhinesmith Compass Massachusetts, LLC

85 Main St, Chatham, MA 02633
/36
$7,200,000
- 5 Beds
- 2.5 Baths
- 1,896 Sq Ft
238 Cranberry Ln, Chatham, MA 02633

This private oasis in North Chatham , hidden by a long and winding lane, takes you into the past. A spectacular historic setting including natural vegetation rests on one of the last large water front parcels in Chatham. Surrounded by over 1.5 acres, with opportunities for a family compound on a fabulous bluff overlooking, and ownership of, prime beach front on Chatham Harbor, Pleasant Bay, and

John Burke William Raveis Real Estate & Home Services

238 Cranberry Ln, Chatham, MA 02633
/58
$1,750,000
- 4 Beds
- 3 Baths
- 1,990 Sq Ft
235 Training Field Rd, Chatham, MA 02633

NEED AN IN-LAW APARTMENT? Tucked away from the road in desirable Riverbay, this comfortable ranch offers easy living with three bedrooms and two full baths. A standout feature is the spacious one-bedroom apartment with its own private entry, a cozy kitchenette, and a fully accessible handicapped bathroom--perfect for guests, extended family, or rental income.The home features a fireplaced living

Keith Bradley Gibson Sotheby's International Realty

235 Training Field Rd, Chatham, MA 02633
/53
$1,400,000
- 4 Beds
- 3 Baths
- 2,391 Sq Ft
68 Chippingstone Rd, Chatham, MA 02633

Ideal rental investment property in Riverbay Estates! Enjoy water views and direct access to Pickerel Pond from this 4-bed, 3-bath home perfect for kayaking and paddleboarding. Features include a first-floor primary suite, living and dining areas with pond views, central A/C, gas heat, and an attached two-car garage. The home is generator ready with a panel for the transfer switch already in

Marcia Thorngate Smith Christie's International Real Estate Atlantic Brokerage

68 Chippingstone Rd, Chatham, MA 02633
/19
$399,000
- 1 Bed
- 1 Bath
- 696 Sq Ft
109 Misty Meadow Ln Unit 2, North Chatham, MA 02650

Set in the desirable Misty Meadow neighborhood, 109 Misty Meadow Unit 2 offers an ideal gateway to the Chatham lifestyle. This ground-floor 1-bedroom, 1-bathroom condominium is a rare find, blending convenience, charm, and investment potential. Whether you're seeking a turnkey rental, seasonal getaway, or an easy-care year-round home, this residence delivers on every front. Inside, the unit is

Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

109 Misty Meadow Ln Unit 2, North Chatham, MA 02650

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