30 Chestnut Drive
Orleans, MA · $3,000,000
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30 Chestnut Drive

Orleans, MA 02653
$3,000,000
0 days on market · Listed Oct 7, 2026
Data refreshed Oct 7, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
4
Baths
3.5
Sq Ft
3,677
Acres
2.1
Year Built
1998
$ / Sq Ft
$816
Days on Market
0

Investment Snapshot

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STR Range (P50)
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Location & Nearby

Map of 30 Chestnut Drive, Orleans MA with nearby beaches and points of interest
HThis property
  • A
    🚤 Gilman Landing
    0.66 mi
  • B
    🌲 Kent's Point
    1.29 mi
  • C
    🚤 Pahwah Landing
    1.37 mi
  • D
    🚤 Meetinghouse Pond Boat Ramp
    1.45 mi
  • E
    🐟 Pilgrim Lake
    1.56 mi
  • F
    🚤 River Road Town Landing
    1.56 mi
  • G
    🌲 Dickinson Conservation Area
    1.60 mi
  • H
    🐟 Crystal Lake
    1.63 mi

About this property

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..

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Listed by Daneen Law, Gibson Sotheby's International Realty