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Patrick Cooper
REALTOR®
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30 Chestnut Dr, Orleans, MA 02653

$3,000,000
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Active
BEDS4 BATHS3 full 1 partial SQUARE FEET3,677 MLS#73587830
STATUSActive PROPERTY TYPEResidential - Single Family

Property Description

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..

30 Chestnut Dr | MLS# 73587830

This single family home located at 30 Chestnut Dr, Orleans, MA 02653 is currently listed for sale with an asking price of $3,000,000. This property was built in 1998 and has 4 bedrooms and 3 full and 1 partial baths with 3677 sq. ft. Search Orleans real estate on patrickcooper.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Full
Cooling: Central Air
Fireplaces: 1
Garage: 2 car attached
Heating: Baseboard, Oil
Home Style: Cape
Lot Size: 2.10 Acres
Taxes: $12,324
Year Built: 1998

Feature Descriptions

Building Area Total: 3677
Compensation Based On: N/A
Compensation Broker Transaction: N/A
Compensation Buyer Agency: N/A
Compensation Sub Agency: N/A
Compensation Sub Agency Offered: N/A
Days on Site: 36
Fireplace Y/N: Yes
GarageY/N: Yes
HeatingY/N: 1
Lot Features: Cleared, Level
Parcel Number: M:0057 B:0000 L:00480,2364643
Parking Features: Attached, Garage Door Opener
Parking Total: 12
Rooms Total: 7
Sewer: Private Sewer
Water: Private
Waterfront Features: 1/10 to 3/10 To Beach

Listed By / Shown By

Listed By

Agency Name: Gibson Sotheby's International Realty
Agent Name: Daneen Law
Agency Phone: 508-255-6000

Shown By

Agent Name: Patrick Cooper
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

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Estimated Payment

$ 8,578.70 per month $6,676.70 Principal & Interest $1,027.00 Property Tax $875.00 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 11/13/2026. The listing information on this page last changed on 11/13/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 11/13/2026 12:11:26 AM EST) or MLSPIN MLS (last updated Thu 11/12/2026 11:38:32 PM EST) or Prime MLS (last updated Thu 11/12/2026 11:32:25 PM EST) or MREIS (last updated Fri 11/13/2026 12:05:15 AM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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