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75 Tilipi Run Chatham MA 02633

Chatham, MA75 Tilipi Run

Sale Price$9,150,000

Sold

MLS Number 21607303

  • Residential
  • Bathroom 6
  • Bathrooms Total Decimal 5
  • Bedrooms 6
  • Full Bath 4

Situated in one of Chatham's most prestigious neighborhoods, this luxurious Morris Island residence is truly unique among waterfront properties. Perched high above the shoreline, with panoramic views of the Atlantic Ocean and Monomoy Islands, this world class home offers a magnificent living experience. Commanding views from nearly every room, this six bedroom, four full and two half bath home has excellent flow and generously proportioned rooms. The finest artisan fixtures and custom craftsmanship are seen throughout. Highlights include a magnificent great room with stone and wood architectural touches, a gourmand's kitchen, a magnificent first floor master suite, billiard room, & a lower level filled with every amenity imaginable. gardens, this is one of Chatham's finest properties.

Listed by Chris Rhinesmith of Pine Acres Realty

Listing Sold by Pine Acres Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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113 Seapine Road Chatham MA 02650

Chatham, MA113 Seapine Road

Sale Price$9,150,000

Sold

MLS Number 22500816

  • Residential
  • Bathroom 6
  • Bathrooms Total Decimal 5.5
  • Bedrooms 4
  • Full Bath 5

Designed by award-winning firm Polhemus Savery DaSilva and enhanced by designer Lisa Tharp, this waterfront masterpiece embodies timeless coastal luxury. Perfectly sited on Crows Pond, the open-concept main level captures stunning water views from every angle--including the chef's kitchen, great room, and dining area. These spaces open to a screened porch, stone patio, infinity pool, and deck--offering a front-row seat to Fourth of July fireworks.Sophisticated details like coffered ceilings, custom built-ins, a monochrome palette, and striking fixtures elevate the home's elegant aesthetic. A private first-floor guest suite includes its own patio and spa-like bath. Upstairs, find a luxurious primary suite, a water-view bedroom, a charming children's room, and a central loft. Designed for entertaining, the lower level offers a bunk room, full bath, game room, media space, and direct access to an outdoor shower. This turnkey, resort-style retreat offers seamless indoor-outdoor living and exceptional accommodations for guests--all in a setting that defines coastal sophistication.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

Listing Sold by cci.unknownoffice

$
$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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260 North Bay Road Barnstable MA 02655
Sold

MLS Number 21609028

  • Residential
  • Parking Spaces 3
  • Bathroom 8
  • Bathrooms Total Decimal 7
  • Bedrooms 5

Classic Cape Cod Estate! This stunning and traditional Royal Barry Wills waterfront residence sits on the banks of Cotuit Bay and offers magnificent water views, 275 feet of water frontage and inspirational sunsets. Capturing the luxurious spirit of Oyster Harbors, a private gated community, this home features elegant interiors with rich details, modern comforts and extraordinary views. Dramatic vaulted ceilings and expansive windows; sprawling master suite; chef's kitchen with two granite center islands; handsome home library; a fabulous entertainment room in the lower level; and formal and informal living spaces all provide ample room to host family and friends. The 1.52 acre site combines access to outdoor adventure and modern amenities in a natural setting. Add in a private 2 bedroom, 1,287 sq ft guest house, an in-ground pool, sandy beach and private dock, and this property takes your life to new heights!

Listed by Robert B Kinlin of Robert Paul Properties,Inc.

Listing Sold by Robert Paul Properties,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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123 Seapuit River Road Barnstable MA 02655
Sold

MLS Number 21304354

  • Residential
  • Bathroom 4
  • Bathrooms Total Decimal 3.5
  • Bedrooms 4
  • Full Bath 3

Handsome mid-century modern. Spectacular lot with spralling estate settting with magnificent views of river, Dead Neck and Nantucket Sound. 240 feet of shorefront, deep water dock, beach house on the shore with kitchen, bath & bunk room. Large sitting room facing the water.

Listed by Oyster Real Estate

Listing Sold by Oyster Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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79 Sand Point Barnstable MA 02655

Barnstable, MA79 Sand Point

Sale Price$9,000,000

Sold

MLS Number 22300428

  • Residential
  • Parking Spaces 8
  • Bathroom 6
  • Bathrooms Total Decimal 5.5
  • Bedrooms 6

Sun, Sand, and Sea...'The waves of the sea help me get back to me'...and they are yours at this extraordinary residence. The estate setting offers privacy and gloriously commanding views of North Bay and the Cotuit Narrows. Beautifully designed 5,000 square foot floor-plan optimizes the water views with gorgeous spaces for entertaining and relaxing. Hand-sewn French Oak flooring enhances the Great Room with cathedral ceiling, and Chef's Kitchen with Sub-Zero & Thermador. Pantry with Wine Fridge, separate Laundry Room, Beautiful Office/Den space. 5 Bedrooms - 3 Ensuite - plus Carriage House with Kitchen & Full Bath. The deep water Dock is a boater's dream, substantial and protected, complete with an electric Boat Lift, labelled 16,000 pound capacity. This offering includes 50% ownership in the LLC which owns the abutting parcel, 81 Sand Point, on which the heated gunite lap pool was built in 2019 (50' x 10'). Extraordinary Residence in an Outstanding Location.

Listed by Chuck Tuttle of William Raveis Real Estate & Home Services

Listing Sold by cci.unknownoffice

$
$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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52 Oyster Bluff Chatham MA 02633

Chatham, MA52 Oyster Bluff

Sale Price$8,995,000

Sold

MLS Number 22304126

  • Residential
  • Bathroom 6
  • Bathrooms Total Decimal 5.5
  • Bedrooms 5
  • Full Bath 5

A rare offering in Chatham....Formerly part of The Plum Estate, this salt waterfront home offers stunning water views over The Oyster Pond , magnificent pool, spa and patio area and large dock capable of handling multiple boats. This 5BR home underwent a meticulous renovation between 2013-2016 ,preserving original details while optimizing the finest of today's conveniences. The original double doors open unto a truly Great room with high ceilings, fireplace, stunning water vistas and room for multiple sitting and dining areas. Adjacent is the renovated kitchen with center island, breakfast nook and ample cabinetry, A luxurious study/media room , half and full bath complete the first floor. The left side of the house opens to a private ''napping house'' with second study/media room, full bath and bedroom. The second floor offers a spacious primary suite with double closets and full bath. Three additional bedrooms share two baths. The lower level boasts a games and more room with pool table ,and additional table seating and lounging space. Coastal gardens and lawns surround for privacy. Close proximity to shopping and downtown Chatham.

Listed by Lori L Fanning Smith of Compass Massachusetts,LLC

Listing Sold by Compass Massachusetts,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1025 Old Post Road Barnstable MA 02635
Sold

MLS Number 21903441

  • Residential
  • Bathroom 5
  • Bathrooms Total Decimal 4.5
  • Bedrooms 4
  • Full Bath 4

Set on the sparking waters of North Bay at the end of a tree-lined drive, this magnificent waterfront estate blends the very best of indoor and outdoor living. Boasting unparalleled attention to detail, the modern interior is highlighted with soaring ceilings, an open floor plan with defined spaces, and fine craftsmanship throughout. The waterside kitchen is well-appointed with top-of-the-line appliances, custom cabinetry, stone countertops, and elegant fixtures. The dramatic walls of windows superbly frame the stunning water views and expansive grounds, which include lush gardens, tennis court, pool and pool house with guest suite, and protected dock. This exceptional property is close to Cotuit and Osterville villages and several world-class golf resorts.

Listed by Paul E Grover of Robert Paul Properties,Inc.

Listing Sold by cci.unknownoffice

$
$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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249 Seapuit Road Barnstable MA 02655

Barnstable, MA249 Seapuit Road

Sale Price$8,650,000

Sold

MLS Number 22106812

  • Residential
  • Parking Spaces 2
  • Bathroom 4
  • Bathrooms Total Decimal 3.5
  • Bedrooms 4

The Seapuit neighborhood of Osterville was developed on the site of the 200 acre Seapuit Golf Club, one of the earliest golf clubs on Cape Cod, and now consists of large private residential lots. This unique waterfront property, once the site of the Seapuit Inn, consists of three lots. The large, elevated house lot (249 Seapuit Road) is 4.4 acres with frontage on Isham's pond and connected to North Bay. Cedar Tree Landing (253 Seapuit Road) is 2.6 acres fronting on North Bay with a license for a seasonal dock, float, and bulkhead. The third lot (0 Seapuit Road) is 0.74 acres with frontage on Middle Pond and connected to North Bay. It has a Conservation Order of Conditions to build a 3 bedroom house. A property of this size is rarely available and offers the opportunity to create a multisite waterfront estate. The property is offered ''as is''.Osterville is convenient to executive jet service in Hyannis and international airports in Boston and Providence.

Listed by Stewart Young of LandVest,Inc.

Listing Sold by Berkshire Hathaway HomeServices Robert Paul Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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153 Bayberry Way Barnstable MA 02655

Barnstable, MA153 Bayberry Way

Sale Price$8,600,000

Sold

MLS Number 21006295

  • Residential
  • Bathroom 7
  • Bathrooms Total Decimal 6
  • Bedrooms 5
  • Full Bath 5

Designed by well known architect Doreve Nicholaeff, this exquisite waterfront residence features extraordinary design displaying exceptional architectural appointments. Magnificent water views can be found from every room and the western exposure provides glorious sunsets. The entry foyer is spacious and the handsome millwork and contemporary white washed rooms carry into the living room, dining room and kitchen. A lavish master suite is complete with a beautifully appointed office. All auxiliary bedrooms are en suite and the second level is balanced by a family room with outstanding vistas. The dramatic staircase continues to a grand observatory room on the third level. This beautifully crafted and warmly comfortable home is complete with a tennis court, sandy beach and private deep water dock.

Listed by Robert B Kinlin of Robert Paul Properties,Inc.

Listing Sold by Robert Paul Properties,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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560 Fox Hill Road Chatham MA 02633

Chatham, MA560 Fox Hill Road

Sale Price$8,500,000

Sold

MLS Number 21508896

  • Residential
  • Bathroom 9
  • Bathrooms Total Decimal 8
  • Bedrooms 6
  • Full Bath 7

Beautifully positioned high on a bluff, this exquisite custom designed coastal retreat offers commanding water views and a deep water dock on Crow's Pond with access to Pleasant Bay and the Atlantic beyond. This exceptional property built with the finest craftsmanship and attention to detail, offers a Christopher Peacock designed kitchen built for entertaining and maximizing views. The home boasts over 10,000 s.f. of living space on three levels with 6 bedrooms and 7.5 baths. Highlights include a great room with coffered ceilings, walls of windows and a fireplace. A breathtaking stone balcony. A master retreat with double walk in closets and home office with mahogany details. The lower level offers additional entertaining space, exercise room, second kitchen and cabana like access to the outdoor Gunite pool and spa.

Listed by David DePasquale of Pine Acres Realty

Listing Sold by Robert Paul Properties, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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504 Old Harbor Road Chatham MA 02650

Chatham, MA504 Old Harbor Road

Sale Price$8,500,000

Sold

MLS Number 22400780

  • Residential
  • Mls Status Closed
  • Parking Spaces 12
  • Bathroom 6
  • Bathrooms Total Decimal 6

''Turntide'' is a spectacular quintessential Cape Cod estate featuring elevated breathtaking panoramic vistas of Chatham Harbor & Atlantic. From this 8 BED/5.5BA mansion you will enjoy unsurpassed sunrises and romantic nights watching the moon rise over the Outer Beach. You will never want to leave. This timeless masterpiece by Architect Edward Sears Read demonstrates the beauty of classic custom architectural moldings and graciously designed living spaces to accommodate every lifestyle. The 2.94 acres of property with sweeping lawn to almost 300 ft of private sandy beach, offers endless possibilities for a pool, tennis court, or a guest house to expand this legacy property further...This is a once in a lifetime opportunity to own one of the finest iconic waterfront estates in Chatham. This North Chatham address is nearby Chatham center for dining and shopping, or Shore Rd, Chatham Bars Inn, the Fish Pier and all the best that Chatham has to offer. Location! Location! Location!

Listed by The Nickerson Power Group of Compass

Listing Sold by Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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219 Green Dunes Drive Barnstable MA 02672
Sold

MLS Number 21714592

  • Residential
  • Bathroom 11
  • Bathrooms Total Decimal 9
  • Bedrooms 5
  • Full Bath 7

Stunning NEW grand Cape style, south facing, waterfront estate designed by noted architect Doreve Nicholaef! The beautiful Private Sandy Beach is magnificently paired with this truly inspirational home. The grand foyer w curved walls & staircase, textures, colors, and endless ocean views will delight the senses. The kitchen area (east wing) gracefully flows to the great room & dining area. Rare imported sycamore adorns the cabinetry and built-ins throughout much of the first fl. Kitchen has 2 islands, fireplace, Viking & Gagganau appliances, all overlooking wall of windows w Lutron power shades. The North wing houses butlers pantry, dog grooming/flower room, mudroom & 4 car garage w car wash hookup! West wing has office/library and 1300sqft master w his & her luxury baths and closets... Upstairs are 3 more magnificent bedrooms with endless water views, unique private baths & access to wonderful deck designed to maximize amazing sunset views. The 5th bedroom/bunk room has 4 built-in beds, play area, & private bath. Lower level has gym, sauna, steam room, climatized art room, electronic command center, cedar room & unfinished bonus room could be used for media room or wine cellar. Smart House design with "Control 4" system. Whole house generator. 8 bedroom septic system. Design for pool and pool house available upon request. 3 floor elevator. Included in the sale is buildable second lot. Qualified buyers please request private showing.

Listed by Jonathan A Matel of William Raveis Real Estate & Home Services

Listing Sold by Kinlin Grover Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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broker reciprocity The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than SeasCape Realty, Inc. are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor SeasCape Realty, Inc. shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

This site was last updated May 28, 2026 6:21 PM EDT. All properties are subject to prior sale, changes, or withdrawal.

SeasCape Realty, Inc. has chosen to display only certain towns and/or types or styles of properties. This site may not show all listings that are available through the Cape Cod & Islands Multiple Listing Service, Inc.