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..
For sale
$3,000,000
30 Chestnut Drive, Orleans, MA 02653
4beds
3,677sqft
Single Family Residence
Built in 1998
2.1 Acres Lot
$2,824,000 Zestimate®
$816/sqft
$-- HOA
What's special
Wood-burning fireplaceDeeded beach accessBeautifully appointed kitchenCharming window seatLuxurious first-floor primary suiteFour-season sunroomSurrounded by mature landscaping
- 26 days
- 2,399
- 226
Zillow last checked:
Listing updated:
Listed by:
Daneen Law 508-237-0977,
Gibson Sotheby's International Realty
Source: CCIMLS,MLS#: 22605085
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Heating
- Oil
Cooling
- Central Air
Appliances
- Included: Oil, Water Heater
Features
- Flooring: Wood, Tile
- Basement: Full
- Number of fireplaces: 1
Interior area
- Total structure area: 3,677
- Total interior livable area: 3,677 sqft
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Direct Access, Garage Door Opener
- Attached garage spaces: 2
Features
- Stories: 2
- Patio & porch: Patio, Porch, Screened Porch
- Exterior features: Outdoor Shower
- Has private pool: Yes
Lot
- Size: 2.1 Acres
Details
- Additional structures: Outbuilding
- Parcel number: ORLE M:57 B: L:480
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Shingle Siding
- Roof: Asphalt,Pitched
Condition
- Year built: 1998
Utilities & green energy
- Water: Well
Community & HOA
Location
- Region: Orleans
Financial & listing details
- Price per square foot: $816/sqft
- Tax assessed value: $2,088,500
- Annual tax amount: $12,324
- Date on market: 10/7/2026
- Cumulative days on market: 26 days
Estimated market value
$2,824,000
$2.68M - $2.97M
$4,026/mo
Price history
| Date | Event | Price |
|---|---|---|
| 10/7/2026 | Listed for sale | $3,000,000+156.4%$816/sqft |
Source: | ||
| 3/6/2015 | Sold | $1,170,000-2.4%$318/sqft |
Source: | ||
| 12/28/2014 | Listed for sale | $1,199,000+23.6%$326/sqft |
Source: oldCape Sotheby's International Realty #21411071 Report a problem | ||
| 2/16/2011 | Sold | $970,000-2.9%$264/sqft |
Source: | ||
| 10/15/2010 | Listing removed | $999,000$272/sqft |
Source: NCI #20907184 Report a problem | ||
| 7/2/2010 | Price change | $999,000-8.3%$272/sqft |
Source: NCI #20907184 Report a problem | ||
| 6/11/2010 | Price change | $1,090,000-4.4%$296/sqft |
Source: NCI #20907184 Report a problem | ||
| 5/27/2010 | Price change | $1,140,000-4.2%$310/sqft |
Source: NCI #20907184 Report a problem | ||
| 5/15/2010 | Listed for sale | $1,190,000-7.8%$324/sqft |
Source: NCI #20907184 Report a problem | ||
| 8/29/2009 | Listed for sale | $1,290,000+658.8%$351/sqft |
Source: NCI #20907184 Report a problem | ||
| 3/17/1995 | Sold | $170,000$46/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $11,686 +3.2% | $1,872,700 +6% |
| 2024 | $11,328 +7.8% | $1,767,200 +4.8% |
| 2023 | $10,508 +10% | $1,686,700 +38.4% |
| 2022 | $9,553 | $1,218,500 |
| 2021 | $9,553 +4.2% | $1,218,500 +0.5% |
| 2020 | $9,170 +8.5% | $1,212,900 +6.2% |
| 2019 | $8,453 +16.4% | $1,142,300 +4.3% |
| 2018 | $7,263 +6.8% | $1,095,400 +1.9% |
| 2017 | $6,803 -10.8% | $1,074,800 -9% |
| 2016 | $7,627 +1.9% | $1,180,700 +1.3% |
| 2015 | $7,485 +3.5% | $1,165,900 |
| 2014 | $7,229 +1% | $1,165,900 -0.6% |
| 2013 | $7,156 +6% | $1,173,100 +2.7% |
| 2012 | $6,749 +5.5% | $1,141,900 -0.6% |
| 2011 | $6,399 -14.8% | $1,148,900 -21.2% |
| 2010 | $7,513 +5% | $1,458,800 -0.5% |
| 2009 | $7,153 +16.6% | $1,465,800 +8% |
| 2008 | $6,135 +6% | $1,357,300 +0.2% |
| 2007 | $5,787 +2.1% | $1,355,200 -0.5% |
| 2006 | $5,666 +3.8% | $1,361,900 +9.5% |
| 2005 | $5,459 +2.5% | $1,243,600 +2.9% |
| 2004 | $5,327 +5.2% | $1,208,000 +22.1% |
| 2003 | $5,065 | $989,200 |
Find assessor info on the county website
Monthly payment
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