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20 Fairway Drive Chatham MA 02633

Chatham, MA20 Fairway Drive

Sale Price$5,300,000

Sold

MLS Number 22102585

  • Residential
  • Bathroom 7
  • Bathrooms Total Decimal 6.5
  • Bedrooms 4
  • Full Bath 6

Sited in town in one of Chatham's most sought after locations, this custom crafted home sets the bar on luxurious living. With views stretching over the golf course and Chatham Harbor, this spectacular 4 BR, 7 BA home with 5,042 square feet is rich in architectural design with crown molding, coffered ceilings, paneled wainscoting and classic fir floors throughout. The main level has open and functional living spaces with 4 fireplaces including a chefs kitchen with large marble island, top-of-the-line appliances, serving galley and breakfast area. Two sumptuous master suites grace the second floor and offer private baths with soaking tubs, walk in closets, and vaulted ceilings. One also includes a fireplace and balcony. Two additional en-suite guest bedrooms complete this level. Additional square footage in custom lower level includes a billiard/media area with bar, wine cellar and gym. The outdoor space offers a resort experience and provides the ultimate in entertaining with the outdoor kitchen, heated saltwater pool /spa, BBQ area and Widows Walk observation deck. Please verify all information contained herein.

Listed by Jessica A King of Compass Massachusetts,LLC

Listing Sold by Cape Cod Associates R E

$
$
%
$/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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30 Deer Run Orleans MA 02653

Orleans, MA30 Deer Run

Sale Price$5,300,000

Sold

MLS Number 22501030

  • Residential
  • Bathroom 7
  • Bathrooms Total Decimal 6.5
  • Bedrooms 5
  • Full Bath 6

Stunning Salt Waterfront Estate on the Mill Pond with panoramic views to Roberts Cove & Nauset Harbor to the Light House & beyond!Superior quality throughout this 5 bedroom 5 1/2 bath home. Great privacy & beautiful easy to care for landscaping. Wonderful open sunny rooms & great flow. Large gourmet kitchen & formal dining room. Beautiful Great Room with a fireplace wall, sliders & a French door to the deck! Super first floor office. Great family room with a beamed ceiling, & it is adjacent to the screened in porch. Lovely first floor primary bedroom en suite with 2 walk in closets & adjacent office. Large sun filled guest rooms with fabulous views. Artistically beautiful inside & out! Short distance to Nauset Beach around the bend, swim in your pool or at the association private beach & sail from you private mooring to Nantucket!

Listed by Nikki Carter of William Raveis Real Estate & Home Services

Listing Sold by Gibson 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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4 Ministers Lane Chatham MA 02650

Chatham, MA4 Ministers Lane

Sale Price$5,300,000

Sold

MLS Number 22501085

  • Residential
  • Bathroom 7
  • Bathrooms Total Decimal 6.5
  • Bedrooms 5
  • Full Bath 6

MAJESTIC SEASIDE LIVING. This unrivaled oceanfront estate located on prestigious Ministers Point in North Chatham offers grand scale living with dramatic Atlantic Ocean vistas. The meticulously designed cedar shingle and sprawling stone exteriors seamlessly blend the elegant interiors that boast striking architectural details, custom finishes and the highest quality craftsmanship. The 11 rooms radiate light and a breadth of picturesque vistas of Chatham's coastline and stretches of North and South Beach. The entry opens to a spectacular living and dining room with soaring coffered ceilings, an imported fireplace, and walls of windows that unveil the majestic sea backdrop. A grand family room with fireplace assures large-scale entertaining while the nearby wood paneled ensuite study delivers coziness and privacy. The main floor is complete with a fully equipped chef's kitchen that leads to a separate second floor ensuite bedroom above the garage. The main stairway leads to a magnificent master suite, a third en suite bedroom and a bookshelves sitting area. The lower level features two more ensuite bedrooms facing the sea. The grounds are mesmerizing with mature trees, native plants and paths to the sea.

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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7 Telegraph Hill Road Provincetown MA 02657
Sold

MLS Number 22405028

  • Residential
  • Parking Spaces 10
  • Bathroom 4
  • Bathrooms Total Decimal 3.5
  • Bedrooms 3

Welcome to 7 Telegraph Hill, an extraordinary home in Provincetown's West End. This remarkable residence has been featured in *Home Remodeling Magazine* and *American Art Collector*. The open concept second-floor living space offers breathtaking ocean views, including Long Point and Wood End lighthouses, through a 10-ft glass wall that opens onto a deck spanning the width of the home. The living & dining spaces are anchored by a striking fireplace, while the custom kitchen features Christopher Peacock cabinetry, a Subzero refrigerator, and a 6-burner Wolf range. A spacious quartz island, bar/pantry with wine chiller, and powder room complete the space. The oversized first-floor primary suite boasts another expansive deck with views, a renovated marble bath with a soaking tub, and a walk-in closet. Two guest suites with en-suite baths enjoy their own private outdoor spaces. Amenities include family room, home office, 2-car garage, home automation, lush gardens and impeccable hardscaping.

Listed by Iskren Georgiev of Gibson Sotheby's International Realty

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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245 North Bay Road Barnstable MA 02655
Sold

MLS Number 22504570

  • Residential
  • Parking Spaces 4
  • Bathroom 6
  • Bathrooms Total Decimal 5.5
  • Bedrooms 5

Designed by renowned architect Royal Barry Wills, this magnificent Oyster Harbors residence combines timeless elegance with a coveted resort lifestyle in one of Cape Cod's most sought-after communities. The stately white brick facade and lush plantings set the stage immediately upon approach, hinting at the inimitable architectural and design details throughout. Sophisticated yet refined interiors retain many original design elements by the late Richard FitzGerald and complement sweeping views of the Donald Ross-designed golf course that are captured from nearly every room. Across the first level, French doors seamlessly connect to multiple outdoor living areas, including a swimming pool, hot tub, brick patio, and expansive bluestone terrace overlooking the golf course. At the heart of the home, a Smallbone kitchen with a butler's pantry effortlessly flows into the adjacent sunroom, formal dining room, and living room. Offering the utmost privacy and convenience, the first-floor primary suite enjoys its own private patio, as well as a fireplace, walk-in closet, and luxurious bath. The second level includes two well-appointed bedrooms, an office, and two full baths. Perfect for staff or guests, an attached in-law suite above the garage provides two additional bedrooms with a kitchenette and living room. A true legacy property set behind the gates of Oyster Harbors, this extraordinary residence delivers the best of Cape Cod living.

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

Listing Sold by LandVest, 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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861 Sea View Avenue Barnstable MA 02655
Sold

MLS Number 20906611

  • Residential
  • Bathroom 7
  • Bathrooms Total Decimal 6.5
  • Bedrooms 7
  • Full Bath 6

Cape Cod living is at its best in this classic Wianno beach house where stellar views of Nantucket Sound abound from nearly every room. The magnificent 3.34-acre estate setting is a rarity on Sea View Avenue and offers exceptional privacy. With the ocean as its backdrop, the massive window-walled great room with a six-foot fireplace, traditional beamed ceiling, and hard pine floors. Sharing the ocean view, the formal dining room with fireplace opens through French doors to a flagstone patio, a perfect spot for after-dinner conversation. The updated kitchen can serve any occasion from a quiet dinner for two to a large family celebration. Also a detached garage with potential for guest accommodations. A beachfront cabana is an added delight with a central gathering area, changing rooms, and water service. An opportunity not to be missed!

Listed by John B Cotton,Jr of Sotheby's International Realty

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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290 North Bay Road Barnstable MA 02655
Sold

MLS Number 22203160

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

Spectacular sunsets and expansive water views across Cotuit Bay from this Oyster Harbors waterfront estate. Enjoy watching the boats motor between Cotuit Bay & North Bay through ''The Narrows'. Meander across the professional landscaped grounds to your own paved driveway leading down to the water's edge. Slip in a paddle board or kayak and enjoys hours of peaceful gliding throughout Cotuit Bay, North Bay & West Bay. This sprawling 4,100 sf home provides water views from all rooms. The exceptionally large sun room provides multiple gathering areas for all family & friends to enjoy while soaking in the water views & southwest prevailing breezes. The 1st floor also consists of a large formal living room w/ a fireplace, an impressive family room w/ a soaring ceiling, beams, & a fireplace, a kitchen, half bath, & a large master suite w/ a multitude of closets. The 2nd floor of the main house features two bedrooms & a bath (all w/ water views). There is a large bunk room (w/ water views) and bath above the oversized 2-car att. garage. Peaceful waterfront living! The septic system has failed and will be the Buyer's responsibility to replace. All info. should be verified by potential Buyers & their representatives. The swordfish weathervane is excluded.

Listed by John J Hopkins of Frank A Sullivan Real Estate

Listing Sold by Village 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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134 Coles Pond Road Dennis MA 02641

Dennis, MA134 Coles Pond Road

Sale Price$5,250,000

Sold

MLS Number 2011651

  • Condo
  • Bathroom 8
  • Bathrooms Total Decimal 6.5
  • Bedrooms 8
  • Full Bath 5

A Spectacular Waterfront Residence Set Along A Beautiful Stretch Of Unspoiled Cape Cod Coastline. This Gracious Home Provides Over 5000 Sq. Ft. Of Living Space With Magnificent Waterviews From Almost Every Room. A Separate Guest Apartment Compliments This Extraordinary Property.

Listed by Robert B Kinlin of Kinlin Grover Real Estate

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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554 Wianno Avenue Barnstable MA 02655
Sold

MLS Number 21604520

  • Residential
  • Parking Spaces 4
  • Bathroom 8
  • Bathrooms Total Decimal 7.5
  • Bedrooms 12

Located at the end of Wianno Avenue just down the way from the fabled Wianno Club, this incomparable site is 2.08 acres with panoramic views, almost 300 feet of sandy beach, stone revetments, and 2 stone jetties on Nantucket Sound. The house is a classic 1880s summer cottage'' with classic millwork, high ceilings, 12 bedrooms, 7 and a half baths, 3 fireplaces, covered porches, a 3 car detached garage, and a tennis court. A new Title V 12-bed septic system has been installed allowing for the house as is or a new house and guest house. A site of this size is rarely available and offers the opportunity to create a family compound for generations.

Listed by Stewart Young of LandVest, Inc.

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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372 Fox Hill Road Chatham MA 02633

Chatham, MA372 Fox Hill Road

Sale Price$5,250,000

Sold

MLS Number 22500675

  • Residential
  • Bathroom 2
  • Bathrooms Total Decimal 2
  • Bedrooms 2
  • Full Bath 2

Overlooking beautiful Crows Pond, this exquisite property has a myriad of opportunities with a six bedroom septic, conceptual building plans for a four bedroom main house and an existing two bedroom, two bath waterfront home that feels like a private sanctuary exuding a perfect blend of luxury living with an elegant coastal charm. Located on 1.8 acres across from Eastward Ho Country Club. The home highlights custom craftsmanship and detailed finishes and provides ample space for intimate or large gatherings with generously proportioned indoor and outdoor living spaces. The great room with gas fireplace and dining area are view-filled and adjoin a sunroom with a wood burning fireplace, walls of windows and access to a patio. The kitchen has all the amenities as well as a sitting area that opens to a patio with a firepit. The bedrooms afford privacy with a first floor primary suite and a second level sitting room and en suite bedroom-all with water vistas. This home is a perfect Chatham retreat, but can also provide an exceptional palate to create a custom compound or family property for generations to come.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

Listing Sold by Gibson 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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40 Beach Plum Hill Road Barnstable MA 02655
Sold

MLS Number 21408965

  • Residential
  • Bathroom 10
  • Bathrooms Total Decimal 9
  • Bedrooms 5
  • Full Bath 8

Stunningly sophisticated yet relaxing and warm, this like new waterfront residence on Warren's Cove reflects the owner's love of architecture and art and offers every amenity to today's discerning buyer. Set on a private and tranquil 1.94 acre parcel and featuring an ideal blend of lush vegetation and seasonal color, this 6,166 square foot impeccable waterside residence is an idyllic family retreat with five spacious bedrooms and eight full bathrooms. A dramatic entry hall sets the scene for the rest of the striking interior which includes open living and dining rooms, masterfully designed kitchen, family room, sunroom and exquisite master bedroom suite with his and her private offices. Outside spaces to relax are plentiful with an infinity pool, hot tub, multiple decks and private dock. First floor chandelier is excluded.

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.

Ask A QuestionMore Details

21 Wianno Head Road Barnstable MA 02655
Sold

MLS Number 2037720

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

Located In One Of The Most Desirable Areas In Osterville, This 3 Bedroom, 2.5 Bath Home Is The Ideal Blend Of Comfort And Privacy. Features Include A Large Living Room With Hardwood Floors, A Wall Of Bookshelves And Spectacular Waterviews. A Private Setting Highlighted With Mature Plantings, A Private Sandy Beach And Fabulous Deep Water Dock Complete This Offering. Garden Gates, Wrought-iron Doors, All Ornamental Garden Artwork And Statues, Chandelier And Sconces In Dining Room, And All Furniture And Art Work Are Excluded From The Sale.

Listed by Robert B Kinlin of Kinlin Grover Real Estate

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.

Ask A QuestionMore Details

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 5:21 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.