30 Chestnut Drive
Orleans, MA, 02653
$3,000,000
Set on two private acres in one of East Orleans’ most coveted Barley Neck neighborhoods, 30 Chestnut Road is an exceptional Cape Cod retreat where refined interiors, resort-style outdoor living, and deeded beach access come together beautifully. Designed for both effortless everyday living and memorable gatherings, the home features four bedrooms and 3.5 baths, including a luxurious first-floor primary suite. The open-concept floor plan is anchored by a beautifully appointed kitchen with a generous center island, high-end appliances, and a butler’s pantry. The adjoining living room, with custom built-ins, a charming window seat, and wood-burning fireplace, offers a warm and inviting place to gather, while the four-season sunroom brings the outdoors in throughout the year. A spacious bonus room above the garage provides wonderful flexibility for overflow guests, a home office, or additional recreation space. Outside, the property is truly extraordinary. The pool area feels like a five-star private oasis, surrounded by mature landscaping and generous space for lounging, dining, and entertaining. A private path leads to the neighborhood’s deeded beach, making days on the water an effortless part of life here. Adding even more possibility is a separate cottage with electricity and a full foundation, offering exciting potential for conversion to an accessory dwelling unit, subject to Town approvals. Private yet close to the beaches, boating, and village amenities that make East Orleans so special, 30 Chestnut Road offers the space, setting, amenities, and lifestyle today’s discerning buyers seek. This is Cape Cod living at its finest..
Current real estate data for Single Family in Orleans as of Oct 10, 2026
53
Single Family Listed
114
Avg DOM
756
Avg $ / SqFt
$2,420,636
Avg List Price
Property Details
Price:
$3,000,000
MLS #:
22605085
Status:
Active
Beds:
5
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
orleans
Listed Date:
Oct 7, 2026
Finished Sq Ft:
3,677
Total Sq Ft:
3,677
Lot Size:
91,345 sqft / 2.10 acres (approx)
Year Built:
1998
Schools
School District:
Nauset
Interior
Appliances
Oil, Water Heater
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
1
Flooring
Wood, Tile
Heating
Oil
Exterior
Architectural Style
Cape Cod
Attached Garage YN
1
Construction Materials
Shingle Siding
Exterior Features
Outdoor Shower
Garage Spaces
2
Other Structures
Outbuilding
Parking Features
Direct Access, Garage Door Opener
Patio And Porch Features
Patio, Porch, Screened Porch
Roof
Asphalt, Pitched
Stories
2
Financial
Tax Year
2026
Taxes
$12,324
Map
Contact Us
Mortgage Calculator
Community
- Address30 Chestnut Drive Orleans MA
- CityOrleans
- CountyBarnstable
- Zip Code02653
Subdivisions in Orleans
Property Summary
- 30 Chestnut Drive Orleans MA is a Single Family for sale in Orleans, MA, 02653. It is listed for $3,000,000 and features 5 beds, 4 baths, and has approximately 3,677 square feet of living space, and was originally constructed in 1998. The current price per square foot is $816. The average price per square foot for Single Family listings in Orleans is $756. The average listing price for Single Family in Orleans is $2,420,636. To schedule a showing of MLS#22605085 at 30 Chestnut Drive in Orleans, 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 Lucy30 Chestnut Drive
Orleans, MA


