Discover a timeless piece of livable art. It is a masterclass in organic design by architect Robert Kennedy and builder Eric Winslow. Set on 2.48 wooded acres bordering the estuaries of Herring River (Cape Cod National Seashore), this estate offers ultimate privacy. Kennedy’s signature integration of architecture and custom furnishings begins at the boardwalk entrance and continues throughout the home.The interior features connected separation, using a central chimney, open balconies, and elevation changes to define spaces while maintaining an airy flow. Multiple curving perches offer intimate views of the wild Wellfleet landscape. While social areas are open, the bedrooms are distinctly private. The property also includes a 400 sq. ft. studio loft with a kitchenette above the two-car garage, plus a separate structure housing an artist’s studio (also with kitchenette) and a once-functional indoor pool. This home is the pinnacle of Outer Cape privacy and architectural intent, perfect for the discerning visionary.
Current real estate data for Single Family in Wellfleet as of Apr 21, 2026
24
Single Family Listed
71
Avg DOM
654
Avg $ / SqFt
$1,508,279
Avg List Price
Property Details
Price:
$2,400,000
MLS #:
22601101
Status:
Active
Beds:
5
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Great Pastures
Listed Date:
Apr 1, 2026
Finished Sq Ft:
4,209
Total Sq Ft:
4,209
Lot Size:
108,029 sqft / 2.48 acres (approx)
Year Built:
1987
Schools
School District:
Nauset
Interior
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
3
Flooring
Wood
Heating
Hot Water
Laundry Features
First Floor
Exterior
Architectural Style
Other
Association Amenities
Road Maintenance
Construction Materials
Shingle Siding
Garage Spaces
2
Lot Features
Conservation Area, Major Highway, House of Worship, West of Route 6
Open Parking YN
1
Other Structures
Pool House
Patio And Porch Features
Deck
Roof
Wood, Shingle
Stories
2
Financial
HOA Fee
$500
HOA Fee Frequency
Annually
Tax Year
2026
Taxes
$15,893
Map
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Community
- Address65 & 75 Deer Path Way Wellfleet MA
- SubdivisionGreat Pastures
- CityWellfleet
- CountyBarnstable
- Zip Code02667
Subdivisions in Wellfleet
Property Summary
- Located in the Great Pastures subdivision, 65 & 75 Deer Path Way Wellfleet MA is a Single Family for sale in Wellfleet, MA, 02667. It is listed for $2,400,000 and features 5 beds, 5 baths, and has approximately 4,209 square feet of living space, and was originally constructed in 1987. The current price per square foot is $570. The average price per square foot for Single Family listings in Wellfleet is $654. The average listing price for Single Family in Wellfleet is $1,508,279. To schedule a showing of MLS#22601101 at 65 & 75 Deer Path Way in Wellfleet, MA, contact your Thomas D Brown R E Associates agent at 508-487-1112.
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Raised in Orleans and now a resident of Truro, Lucy is extremely familiar with life on the Outer Cape. She is experienced in real estate sales on Cape Cod and has been involved in construction, development and real estate for over thirty-five years here on the Outer Cape. She presently handles all facets of marketing for both Brown Associates and Cape Vacation Rentals. Degree in Sales & Marketing; formerly associated with Nickerson Realty Corp. where she handled all phases of land development, a…
More About Lucy
65 & 75 Deer Path Way
Wellfleet, MA