$3,000,000
30 Chestnut Dr
Orleans, MA, 02653
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..
Property Details
Price:
$3,000,000
MLS #:
73587830
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
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
Interior
Above Grade Finished Area
3677
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
1
Heating
Baseboard, Oil
Exterior
Architectural Style
Cape
Attached Garage YN
1
Covered Spaces
2
Garage Spaces
2
Lot Features
Cleared, Level
Open Parking Spaces
10
Parking Features
Attached, Garage Door Opener
Parking Spots
12
Parking Total
12
Waterfront Features
1/10 to 3/10 To Beach
Financial
Tax Year
2026
Taxes
$12,324
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Single Family in Orleans as of Nov 08, 2026
28
Single Family Listed
135
Avg DOM
731
Avg $ / SqFt
$2,362,011
Avg List Price
Community
- Address30 Chestnut Dr Orleans MA
- CityOrleans
- CountyBarnstable
- Zip Code02653
Subdivisions in Orleans
Similar Listings Nearby
Property Summary
- 30 Chestnut Dr Orleans MA is a Single Family for sale in Orleans, MA, 02653. It is listed for $3,000,000 and features 4 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 $731. The average listing price for Single Family in Orleans is $2,362,011. To schedule a showing of MLS#73587830 at 30 Chestnut Dr in Orleans, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Gibson Sotheby’s International Realty. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors 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.
30 Chestnut Dr
Orleans, MA












































