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

Orleans, MA, 02653
$ 3,000,000
Bedrooms5 Baths3.1 Sq 3,677

Monthly Estimate*

$ 20,720

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Single Family Home for sale in Orleans, MA

for $3,000,000 with 5 bedrooms and 3 full baths, 1 half bath. This 3,677 square foot home was built in 1998 on a lot size of 2.1.

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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Single Family Active

Price

$ 3,000,000

Bedrooms

5

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 12,324

Style

Cape Cod

Lot Size

2.1

Year Built

1998

Town/City

Orleans

County/Region

Barnstable

MLS | Web ID

22605085

Features
General
Heating Oil
Cooling Central Air
Roof Asphalt Pitched
Appliances Oil Water Heater
Garage Spaces 2
Patio/Porch Features Patio Porch Screened Porch
Architectural Style Cape Cod
Construction Materials Shingle Siding
Year Built 1998
Stories Count 2
Property Subtype Single Family Residence
Tax Year 2026
County Barnstable
Property Type Residential
Attached Garage true
Garage Y/N true
Other Structures Outbuilding
Total Rooms 7
Full Baths 3
Status Active
Directions Main Street to Barley Neck Road to Nichols Road to Chestnut Drive. GPS may take your down Old Field so you may want to follow these directions
City Orleans
MLS Area Orleans
Lot Size Units Acres
Lot Size Square Feet 91345
Tax Annual Amount 12324
Showing Instructions Call Daneen Law 508.237.0977
Virtual Tour https://www.zillow.com/view-imx/fcf27d39-750e-42ab-a349-f8d722801506?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard
Building Area Units Square Feet
Standard Status Active
Tax Assessed Value 2088500
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Interior
Basement Full
Flooring Wood Tile
Total Fireplaces 1
Air Conditioning Y/N true
Heating Y/N true
Half Baths 1
Total Bedrooms 5
Total Baths 4
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Exterior
Exterior Amenities Outdoor Shower
Parking Features Direct Access Garage Door Opener
Water Source Well
Lot Size Area 2.1
Building Area Total 3677
Lot Size Acres 2.1
Waterfront Y/N false
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* Excluded Features
List By
Daneen Law

Listing Agent

Gibson Sotheby's International Realty

Broker

daneen.law@gibsonsir.com

Email

Affordability Calculator

$21,747
Per Month
95%
5%
0%
Monthly Principal & Interest
$20,720
Monthly Property Taxes
$1,027
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Pricing History
DatePricePrice ChangeDescription
10/7/2026$3,000,000 Listed Price

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30 Chestnut Drive, Orleans, MA, 02653 is a Single Family Home for sale at $3,000,000 with 3,677 sqft and a lot size of 2.1. 30 Chestnut Drive has 5 bedrooms, 3.1 baths, and was built in 1998. The property's zip code is 02653 which is in Orleans, MA