Refine Search
Sort by
$9,850,000
5 Beds 5 Baths 73395925 MLS
Legacy, Lifestyle & Opportunity - A discreet treasure in one of Cape Cod's most prestigious enclaves, this exceptional waterfront property offers rare access to legacy, lifestyle, and limitless potential. Originally part of a historic compound long held by the Mellon family and now by noted philanthropist and collector William Koch, the property stands as a rare opportunity to own a slice of coastal legacy. This waterfront estate offers 1.78 acres of private grounds, a beautifully preserved five-bedroom residence, and a substantial deep-water dock with direct access to Nantucket Sound—accommodating six or more vessels with ease. Inside, the home exudes understated charm with a seamless connection to outdoor living—screened porch, expansive deck, and water views from most rooms. A welcoming main-level primary suite with adjoining study anchors the floor plan, while the heart of the home features a stone fireplace, an open-concept kitchen, and a screened porch that opens to an expansive deck—perfect for entertaining or quiet reflection. Upstairs, guest bedrooms are enhanced by gracious proportions and stunning vistas. With additional buildable parcels from the same legacy estate also available, this is a rare opportunity to establish a private compound in one of New England's most exclusive waterfront enclaves. A sanctuary of coastal beauty and historic significance, all within the beloved village of Osterville - home to world-class golf, protected waters, and the timeless allure of Cape Cod. 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.

14 Indian Trail, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

$7,750,000
7 Beds 11 Baths 73383981 MLS
Privately sited within the prestigious Oyster Harbors golf enclave, this extraordinary estate is a masterclass in architectural sophistication and resort-style living. Encompassing a 10,000-square-foot main residence, a stunning two-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. A gracious covered front porch welcomes you into a dramatic foyer, setting the tone for the refined interiors that follow. The main living spaces unfold in a thoughtfully designed layout that flows from formal living and family rooms to an elegant dining area with each space inviting connection, comfort, and celebration. At the heart of the home, the chef's kitchen is both striking and functional, anchored by dual oversized islands clad in premium granite, and accompanied by a fireside sitting room that beckons lingering conversation. Adjacent, the spectacular sunroom redefines indoor-outdoor living with a custom crafted bar and casual seating area at one end and a full second kitchen with custom built-in grill and dining area at the other, all enclosed by retractable screens for effortless seasonal enjoyment. Tucked away on the main level, the primary suite offers a private sanctuary, with its own fireplace, luxurious spa-like bath, and refined home office. The comfort and sophistication continue on the second level with four generously proportioned en-suite bedrooms and an inviting sitting room. Designed for comfort and connection, the finished lower level offers a wine cellar, media room, game room, and fitness space. This lavish interior flows effortlessly to an equally impressive exterior, where lush landscaping surrounds a resort-style pool framed by expansive lounging areas-perfect for everything from quiet afternoons to grand entertaining. Completing this offering is a beautiful two-bedroom guest house providing privacy and comfort for visiting guests. Set within a prestigious gated enclave with coveted beach and dock rights, this remarkable estate is the perfect fusion of architectural sophistication and everyday warmth - an extraordinary offering in one of Cape Cod's most prestigious settings. 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.

440 Grand Island Dr, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

$779,000
3 Beds 3 Baths 73383281 MLS
Offered for sale for the first time in over 50 years, this antique three-family residence presents a rare development opportunity in Provincetown at a unique price. Spanning 1,362 square feet, the property features two studio apartments on the first floor and a spacious one-bedroom unit with an attic and bonus room on the second floor. This level lot enjoys abundant natural light throughout the day and offers room for potential expansion. The property could convey with architectural drawings for a fully reimagined over 2,000 square foot three-family residence. Betterment has been paid in full. Don't miss this opportunity to either pursue a multi-unit development project or create your own single-family home in Provincetown.

37 D Court Street, Provincetown

Listing courtesy of Listing Agent: Iskren Georgiev from Listing Office: Gibson Sotheby's International Realty.

$1,150,000
2 Beds 2 Baths 73379350 MLS
$200,000 PRICE IMPROVEMENT! A rare opportunity to own the iconic Blue Heron Gallery in the heart of Wellfleet, just steps from Main Street. Originally built as a Truro cottage in 1946 and relocated here in the 1970s, this distinctive property blends history, charm, and opportunity. Zoned for both Commercial and Residential use, it offers endless possibilities—continue as a gallery or boutique, create a live/work space, or convert to a residence (buyer to verify all uses). Beautiful gardens enhance the setting, with restaurants, galleries, boutiques, the harbor, and Wellfleet's famous oysters just moments away. Recent improvements include a newer roof, updated windows, Azek trim, and refreshed landscaping. Price reflects current condition. Buyer to complete septic repair after closing at buyer's expense. Board of Health-approved repair plan in hand; estimated cost $6,000-$8,000. Buyer to perform own due diligence.

20 Bank Street, Wellfleet

Listing courtesy of Listing Agent: Dawn Lee from Listing Office: Gibson Sotheby's International Realty.

$4,499,000
8 Beds 9 Baths 73377530 MLS
Nestled in the heart of the West End, this historic 1847 Greek Revival Captain's Home is now available for purchase after 29 years under the same ownership. As one of the largest buildings in the neighborhood, the West End Inn serves primarily as a private residence but is also licensed as a B&B. The first floor was completely renovated in 2019. The property features three kitchens, a kitchenette, and four separate living quarters, each with private entrances. The light-filled, three-family layout offers potential to be converted into a substantial single-family home. There are nine bathrooms, eight bedrooms, two dens, two decks, two private garden spaces, and a beautifully appointed front yard. The top floor, with its large deck, provides water views and unobstructed vistas of Telegraph Hill and stunning sunsets. Parking is available for five or more cars, and beach access is directly across the street. Betterment paid in full.

44 Commercial Street, Provincetown

Listing courtesy of Listing Agent: Iskren Georgiev from Listing Office: Gibson Sotheby's International Realty.

$2,700,000
7 Beds 7 Baths 73373131 MLS
For the first time in generations, this landmark Pleasant Bay compound—anchored by the iconic "Topside" main residence and the charming two-bedroom "Boathouse"—is offered as a rare, generational waterfront estate, a site long cherished by those who have called it home. With a deep-water dock, moorings, and direct access to the bay, the property delivers a front-row seat to the rhythms of Pleasant Bay and boundless recreation. Both homes enjoy sweeping 270-degree views across the water to Eastward Ho, the Chatham Yacht Club, and the Atlantic beyond. Thoughtfully sited by its original architect to capture the light and water at every turn, "Topside" offers 5 bedrooms and 4.5 baths with timeless coastal character and spaces designed for gathering, while the "Boathouse" sits just above the shoreline, featuring 2 bedrooms, 1 bathroom, and its own deck for quiet moments by the sea. A secluded garden patio and broad waterfront lawn offer a blend of intimacy and scale. With a strong rental history and potential for expansion or personalization, this is a lifestyle property that invites multigenerational living, savvy investment, or a private retreat. A once-in-a-lifetime opportunity to own one of Cape Cod's most storied, landmark waterfront settings.

645 S Orleans, Orleans

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$3,595,000
3 Beds 5 Baths 73371097 MLS
NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retreat ''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 w/walnut top offers space for casual dining & flows to the dining area. The nearby butler's pantry enjoys a Subzero beverage fridge. The inviting living area w/gas fireplace opens to a 3-season porch and is adjacent to the deck that overlooks conservation. The 1st story primary suite boasts an ensuite bath w/radiant floor heat & walk-in closet. The 2nd story features 2 en-suite bedrooms, family room & home office. Finished lower-level w/9'' ceilings, a full bath, & 725 sq ft. Cedar roof, copper downspouts, generator & irrigation by well. With its prime location, its an easy walk to town & the beach.

287 Cedar St, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Compass.

$1,950,000
5 Beds 3 Baths 73369737 MLS
Set on its own peninsula overlooking Buttermilk Bay, this landmark waterfront residence offers an extraordinary 485 feet of direct water frontage and vibrant views in every direction. With water visible from nearly every window, the home captures the beauty, light, and that define life on the Cape. The front garden welcomes you with mature plantings and picturesque arches that create a peaceful and inviting approach. Inside, the home blends Mediterranean architectural character with thoughtful modern updates, offering generous space for entertaining while maintaining the warmth and charm of a classic villa. Bay views greet you immediately and continue to unfold as you move through the living spaces and into the sunroom with panoramic views over the large yard. The main living areas are designed to bring the outdoors in, filling the home with natural light. Upstairs the bedrooms enjoy western exposure, offering serene sunset views over the water at the end of each day.

56 Rip Van Winkle Way, Bourne

Listing courtesy of Listing Agent: James Abdu from Listing Office: Upper Cape Realty Corp..

$6,800,000
5 Beds 3 Baths 73358568 MLS
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 prime beach front on Chatham Harbor, Pleasant Bay, and the Atlantic Ocean beyond. Quick salt water access to anywhere by boat from your own private beach. A perfect spot for relaxing, entertaining under the sun or stars, and creating lasting memories. This coastal property features panoramic water views, five bedrooms, three baths, and 1850+ square feet of living space to leave as you will or make it your own.....Zoning of a 69,000 plus square foot lot in R40 zone allows room for a guest house and a pool with town approvals in addition to the large main house...Buyers and agents should verify all information herein...Floor plans in DOCUMENTS

238 Cranberry Lane, Chatham

Listing courtesy of Listing Agent: John Burke from Listing Office: William Raveis Chatham.

$12,250,000
5 Beds 6 Baths 73342640 MLS
Exquisite Waterfront Estate in Exclusive Oyster Harbors: Experience the pinnacle of coastal luxury with this magnificent Cape Cod waterfront estate, nestled in the prestigious gated community of Oyster Harbors. Boasting 450 feet of pristine water frontage with a private beach and breathtaking views over Cotuit Bay and North Bay, this property offers spectacular sunsets, an elegant coastal lifestyle, and unparalleled privacy. Stepping into the grand foyer, you are greeted by vaulted ceilings and expansive windows that showcase panoramic water views, seamlessly blending the outdoors with the refined interiors. The open-concept living spaces include a gracious living room, a fireplace-warmed dining room with custom built-ins, and a sophisticated sitting area, all designed for effortless entertaining. A private home library, accessed by a spiral staircase, overlooks both the main level and the serene waters of North Bay. The gourmet chef's kitchen is a masterpiece, featuring a granite center island, custom built-ins, and a charming breakfast nook with wraparound picture windows framing the breathtaking waterfront vistas. The sumptuous first-floor primary suite is a sanctuary of relaxation, offering private patio access, a spacious walk-in closet, and a spa-inspired en-suite with dual vanities, a luxurious soaking tub, and a glassless double-headed rain shower. The sun-drenched sunroom complete with a full wet bar and sliders on three sides opens directly to the meticulously designed outdoor living areas. The second level hosts four additional spacious bedrooms, a generous family room, and a bonus room with a private balcony, designed for both comfort and relaxation. This exceptional residence also features a partially finished lower level, thoughtfully designed to enhance both convenience and functionality with direct outdoor access perfect for accommodating small boats, golf carts and other recreational essentials. Set on 1.37 acres of pristine coastal land, this estate is an outdoor enthusiast's paradise. The meticulously landscaped grounds feature a built-in fire pit, an outdoor shower, a waterside in-ground pool, a sandy beach, and a private dock. A rare opportunity to own a world-class waterfront residence, this home delivers unparalleled elegance, modern luxuries, and the very best of Cape Cod's coastal living.

71 Sand Pt, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

$3,999,000
5 Beds 9 Baths 73322653 MLS
Discover the epitome of luxury at this exquisite waterfront estate, a haven of tranquility and elegance. Built in 2002 and meticulously renovated, this stunning home offers unmatched comfort and privacy on 4.32 acres. With prime waterfront access and breathtaking views, this expansive 16-room residence features 5 spacious bedrooms and 9 baths including steam shower. The interior boasts two elegant primary suites with gas fireplaces, expansive walk-in closets, and deep hydro-massaging tubs. The masterfully crafted kitchen is equipped with top-line appliances, custom cabinets and granite countertops. The lower level includes hobby and pool table rooms, a kitchenette, an entertainment center and substantial storage. Outdoors, enjoy a stunning heated saltwater pool, oversized hot tub, waterfalls, multilevel stone terrace, outdoor shower, cabana with full bath and a built-in cooking area.This waterfront estate is more than just a home; it's a lifestyle.

26 Walkerwoods Dr, Harwich

Listing courtesy of Listing Agent: Karen Lopez from Listing Office: Great Estates Realty, Inc..

$9,950,000
6 Beds 9 Baths 73285680 MLS
Discover the epitome of luxury living in this custom-designed waterfront estate, featuring breathtaking views of Eel River and Nantucket Sound. Located in the village of Osterville and set on an expansive and beautifully landscaped 2.4-acre lot, this stunning residence features over 8,000 square feet of meticulously crafted living space with rich details, modern comforts and extraordinary views. The grand interiors seamlessly blend with the exquisitely landscaped outdoor spaces, featuring an inground pool, hot tub, spacious pool house, and a substantial private deep-water dock. Upon entering the home, the grand foyer leads you into the magnificent great room with a two-story custom fireplace, where panoramic vistas of the water and breathtaking sunsets set the scene for unforgettable family gatherings as well as effortless entertaining. The generous floor plan also features a refined library, formal dining room, a gourmet kitchen with center island, custom cabinetry and top-of-the-line appliances and a state-of-the-art home theatre. The six en-suite bedrooms include a first-floor suite with French doors leading to the back yard and a lavish primary suite with a luxurious bathroom, two walk-in closets and a private deck overlooking the water. Enhanced with modern conveniences such as a Sonos whole-house sound system and a 9-zone Hydro air system, every detail has been carefully planned and implemented. Additional highlights include a private guest suite above the attached 3-car garage and a sprawling entertainment room with a balcony on the third level highlighted by western exposure to experience breathtaking sunsets. Located just minutes from the upscale boutiques and renowned dining of Osterville village, this extraordinary property offers a lifestyle of unparalleled elegance and tranquility by the sea. 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.

501 Eel River Rd, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

$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 data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.

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.

board logoCopyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .