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58 Whistler Lane Chatham MA 02633

Chatham, MA58 Whistler Lane

Sale Price$5,800,000

Sold

MLS Number 22201987

  • Residential
  • Bathroom 3
  • Bathrooms Total Decimal 2.5
  • Bedrooms 4
  • Full Bath 2

Set in a highly coveted North Chatham location, this charming four-bedroom residence boasts panoramic ocean views and a pristine private beach to enjoy coastal living at its finest. A spacious deck runs the length of the home along the water, with sliding glass doors that seamlessly connect the indoor and outdoor living spaces. Stunning vistas are on full display throughout, while the spacious grounds allow ample space to add a swimming pool or tennis court. Minutes from everything Chatham has to offer, endless opportunities await in an unrivaled setting.

Listed by Paul E Grover of Berkshire Hathaway HomeServices Robert Paul Properties

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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439 Sea View Avenue Barnstable MA 02655
Sold

MLS Number 22504164

  • Residential
  • Parking Spaces 4
  • Bathroom 6
  • Bathrooms Total Decimal 5
  • Bedrooms 6

Presenting the quintessential Cape Cod beach home on sought-after Sea View Avenue. This classic waterfront residence enjoys unobstructed views of Nantucket Sound with a picture-perfect sandy beach. The six-bedroom home showcases Old World craftsmanship and original period details throughout, including wide heart pine plank floors and paneling. At the heart of the home, a spacious living room with beamed ceilings, built-in bookshelves, and a fireplace gives way to a magnificent sunroom with a wet bar, where days can be spent soaking up the brilliant backdrop. The all-white kitchen offers convenience and functionality, with a pantry, breakfast bar, and access to a glorious swimming pool and patio area through sliding glass doors. A first-floor primary suite boasts breathtaking ocean views that set the stage each morning, while an en suite guest bedroom completes the main level. The second floor features four bedrooms and two full bathrooms, ensuring ample space for family and friends. Additional highlights include a two-car garage, verdant grounds, and multiple outdoor seating areas to bask in an unsurpassed setting. Located minutes from Wianno, Oyster Harbors, the village center, and everything else Osterville has to offer, this iconic beach home delivers an extraordinary lifestyle waiting to be enjoyed.

Listed by Paul E Grover of Berkshire Hathaway HomeServices Robert Paul Properties (508.364.3500), Matthew de Groot of Berkshire Hathaway HomeServices Robert Paul Properties

Listing Sold by cci.UnrepBuyer

$
$
%
$/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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15 Flakeyard Lane Yarmouth MA 02673

Yarmouth, MA15 Flakeyard Lane

Sale Price$5,785,000

Sold

MLS Number 22002663

  • Residential
  • Parking Spaces 25
  • Bathroom 7
  • Bathrooms Total Decimal 6
  • Bedrooms 4

Once upon a time, tucked away along the shores of Lewis Bay facing Nantucket Sound, a rare piece of land featuring 280 degree views was creatively combined with its neighboring properties awaiting a dream come true. Inspired by a vision, this is the day the dream to build the ''Blue Diamond'' was born. Today, a landmark on Cape Cod sited on 2+ acres featuring 400 feet of private beach, this oceanfront estate is unlike anything else you have ever seen. After years of pure commitment in the design & conceptualization to bring a masterpiece to life, this oceanfront property was built to offer timeless elegance enhanced by state-of-the-art amenities. Walk in to find 18 foot ceilings & tall picture windows displaying the beauty that only nature can bring, enhanced by materials imported from all over the world. Fossilized stone from Mexico as columns, Loggia walls covered w/ stone from the Philippines & all doors made from Columbian Oak are a few to mention. Imagine breathtaking sunrises & sunsets from multiple master bedrooms while enjoying the best firework displays on 4th of July. It's your time to live your dream.

Listed by DREAM International of Keller Williams 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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120 Vineyard Road Barnstable MA 02635
Sold

MLS Number 21905874

  • Residential
  • Parking Spaces 10
  • Bathroom 8
  • Bathrooms Total Decimal 7
  • Bedrooms 6

Luxuriously appointed beachfront estate with panoramic views of Nantucket Sound. Privately sited and located in one of the most desirable locations in the Village of Cotuit, this masterful residence has been classically designed with over 5,800 square feet of living space and five bedrooms with en suite baths. The home features vast expanses of windows that showcase dramatic Sound views, chef's kitchen, master suite with den, multiple fireplaces, finished lower level with theater, three car garage, and separate guest cottage.

Listed by Paul E Grover of Berkshire Hathaway HomeServices Robert Paul Properties

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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74 Sears Point Road Chatham MA 02633

Chatham, MA74 Sears Point Road

Sale Price$5,775,000

Sold

MLS Number 21407880

  • Residential
  • Bathroom 4
  • Bathrooms Total Decimal 3.5
  • Bedrooms 5
  • Full Bath 3

This exceptional waterfront property offers arresting panoramas of Stage Harbor and beyond. Situated in one of Chatham's most private enclaves, the property is comprised of two adjoining lots totaling 6.6 acres and 350 feet of water frontage. A long winding driveway and charming barn enhance the property's magical approach. Currently there is an existing five bedroom, three and half bath classic Cape Cod style residence built in 1959 spanning 2,500 s.f. sited on the property. This unbeatable setting offers exceptional potential to built a dramatic dream estate or to reinvent the old. Existing Polhemus Savery DaSilva architectural plans are available. Discover more about this spectacular property upon request.

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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47 & 53 Little Beach Road Chatham MA 02633
Sold

MLS Number 22106088

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

Prominently sited in the sought-after beach enclave of Morris Island, this iconic compound includes two beachfront cottages with glorious ocean views and direct beach access. Evoking relaxed summers of yesteryear, these quintessential Cape cottages can be enjoyed as offered or can be the ultimate setting for a new home and guest house offering magnificent water views in a serene setting. Take a short stroll to town or simply relax while enjoying breathtaking sunrises and sunsets from the waterside decks. #53 is configured as a three-bedroom cottage with an enormous loft. #47 is configured as a two-bedroom cottage with a spacious loft for guests. This rare offering provides an incredible setting to kick off your shoes and bask in the simple yet stunning beauty of Chatham. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

Listed by Paul E Grover of Berkshire Hathaway HomeServices Robert Paul Properties (508.364.3500),

Listing Sold by William Raveis Real Estate & Home Services

$
$
%
$/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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120 Freeman Lane Orleans MA 02643

Orleans, MA120 Freeman Lane

Sale Price$5,760,000

Sold

MLS Number 21401931

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

This magnificent home is reminiscent of the turn-of-the-century shingle style mansions that dotted the New England coast. Some say, this is the best available ocean side estate on Cape Cod. Most of the rooms were designed to take advantage of the breathtaking harbor & ocean views. Incredible layered millwork, extensive moldings, wainscoting & bead board throughout the home create a high degree of originality yet achieve a casual elegance. Each interior & exterior room is located to receive natural light at the most appropriate time of the day. The gardens & pool to the rear of the home are exquisite, creating your own private paradise by the sea. This home was artistically designed by the Boston architect firm of Meyer & Meyer, constructed by master builder Lee Savery of Polhemus & Savery Architects & Builders. Click on Visual Tour.

Listed by Alberti Team of oldCape Sotheby's International Realty

Listing Sold by Buyer Brokers of Cape Cod-

$
$
%
$/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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25 Wikis Way Chatham MA 02633

Chatham, MA25 Wikis Way

Sale Price$5,750,000

Sold

MLS Number 22502194

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

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 by nature's stage of everchangingtides and migratory birds. The property itself is a private oasis of hydrangeas, native oak trees, and pollinator gardens. Set on nearly two acres, the grounds offer resort style living with amenities including a heated gunite pool overlooking the ocean, a tennis court, and sandy beach access to the private association beach. Renovated throughout the years, this classic Cape Cod shingle-style estate exudes both warmth andluxury. As you step into the formal foyer, your eye is immediately drawn to the stunning views beyond.Expansive windows capture the breathtaking scenery throughout. The dining room seamlessly connects to the kitchen, guiding you to the dramatic living room with its cathedral beamed ceilings and a large central hearthan ideal setting for family gatherings and entertaining. This wing also offers abundant storage, including pantry space, a project room, laundry facilities, and a half bath, ensuring both convenience and functionality.The home is thoughtfully designed layout offers the perfect blend of private spaces and convivial family living. The private primary suite is a sanctuary all its own, occupying the entire second floor and accessed by a private stairway. It includes a view-filled office and features two expansive his-and-hers closets. On the main level, the unique "grandchildren suite" provides separate living quarters with three en-suite bedrooms, direct access to the pool, a kitchenette with an inviting sitting area and a cozy central hearth. Beneath this wing and adjacent to the outdoor shower is a separate bunk room with a full bath and laundry accessed from the outdoors offering the perfect hideaway for kids to play and relax while still being close to the main living areas. This magnificent Morris Island estate offers endless possibilities and is a once-in-a-lifetime opportunity.

Listed by Chris Rhinesmith of Compass Massachusetts, LLC

Listing Sold by Christie's International Real Estate Atlantic Brokerage

$
$
%
$/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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77 Towhee Lane Orleans MA 02662

Orleans, MA77 Towhee Lane

Sale Price$5,700,000

Sold

MLS Number 21105482

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

The Best Waterfront Estate & Family Compound on Pleasant Bay. This stunning multi-dwelling one-of-a-kind family compound estate has approx. 345 feet of saltwater frontage on Pleasant Bay with access to the Atlantic Ocean. Beautifully designed and finely crafted home with artistic details, finest amenities and state of the art mechanical systems. Understated casual elegance defines this exquisite home. Custom built home was site oriented to take full advantage of the 180 degree panoramic bay views. Rare two story boat house and charming guest cottage are also included in this property. This estate is truly for the discriminating buyer looking for the finest Cape Cod has to offer. Town approved 10 bedroom septic system. Six bedroom main house, four are being ulitized as en-suite bedrooms.

Listed by Alberti Team of oldCape Sotheby's International Realty

Listing Sold by John C Ricotta & Assoc.

$
$
%
$/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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310 North Bay Road Barnstable MA 02655
Sold

MLS Number 20400913

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

Located in the private gated community of Oyster Harbors is this 1.31 acre waterfront property offering over 200 feet of private sandy beach and private dock. Permits and plans in place for a four bedroom main home. Existing guest house features four bedrooms and water views.

Listed by Kinlin Grover Real Estate

Listing Sold by Buyer Brokerage of Osterville

$
$
%
$/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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373 Bridge Street Chatham MA 02633

Chatham, MA373 Bridge Street

Sale Price$5,700,000

Sold

MLS Number 22000133

  • Residential
  • Bathroom 9
  • Bathrooms Total Decimal 8.5
  • Bedrooms 7
  • Full Bath 8

Available for immediate summer occupancy! Boasting one of Chatham's most sought-after Light House Beach locations, this stunning estate set on 1.54 acres is a true family compound. The brand new 5 BR main house is masterfully designed with a relaxed open layout combining elegance and sophistication. The first floor has a central kitchen, dining room, multiple living spaces with an en-suite bedroom. The upper floor offers a sumptuous master bedroom-suite with a family room and three additional en-suite bedrooms. The lower level has an entertainment room, family room, wine storage and full bath. The guest house built in 2003 offers striking spaces, three fireplaces, a first and second floor master suite, and an indoor lap pool. The estate is enhanced with lushly landscaped grounds, a pool, and a detached garage. (Note: Furniture Photos in Listing sheet are a combo of virtually and past staging efforts)

Listed by Chris Rhinesmith 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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1360 Main Street Barnstable MA 02635

Barnstable, MA1360 Main Street

Sale Price$5,695,000

Sold

MLS Number 22504010

  • Residential
  • Parking Spaces 4
  • Bathroom 4
  • Bathrooms Total Decimal 4
  • Bedrooms 5

This extraordinary Cotuit beachfront home enjoys sweeping views of Sampsons Island and Nantucket Sound. Minutes from everything the village has to offer, the five-bedroom residence boasts an unrivaled location and lifestyle. Immediately upon entering, panoramic views take center stage, with walls of glass that frame the breathtaking surroundings. The open-concept kitchen, dining, and living areas cater to modern living, while a first-floor primary suite offers the utmost convenience. A seaside deck seamlessly blends indoor and outdoor spaces, perfectly designed for relaxing or al fresco entertaining, while a short path at the end of the lawn leads to one of Cape Cod's finest stretches of private beach. On the second level, four additional bedrooms make this home an ideal gathering place for family and friends. A finished lower level, currently outfitted as a home gym, offers flexibility for any need. Blending classic charm with a world-class waterfront setting, this is a rare opportunity to own a truly special piece of Cape Cod.

Listed by Paul E Grover of Berkshire Hathaway HomeServices Robert Paul Properties

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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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 12:51 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.