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For Sale

30 Chestnut Dr, Orleans MA 02653

Orleans, MA 02653

$3M
4 BD · 4 BA · 3,677 sf · 2.1 ac · Built 1998
The residence

Set on two private acres in one of East Orleans' most coveted Barley Neck neighborhoods, 30 Chestnut Drive 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..

At a glance
Property type
Single Family Residence
Status
Active
Year built
1998
Lot size
2.1 acres
Living area
3,677 sf
MLS#
bca3b34bc7281830d7f1bcd89cacc623
Beds · Baths
4 · 4
Location

Orleans, MA.

Orleans sits within Cape Cod, in Massachusetts, and keeps the character of that stretch of the map — its streets, shoreline and architecture read as of a piece with the towns around it. Our advisors know the market here street by street and can speak to how a particular address sits within it.

Estimated Monthly Payment+
$15K/mo
Approximate · principal & interest only
Display Currency
$3M

Indicative conversion — settlement always in USD.

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Listing courtesy of Gibson Sotheby's International Realty · MLSPIN

MLS Property Information Network.The property listing data and information 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 are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing 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 or leasing. 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 set forth herein.

Listings updated Oct 16, 2026

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