Date
Details
Price
Change
Source
9/12/2025
Listed
$1,985,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/43
$1,985,000
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1/43
Property Description
Tucked away behind association common land, this year-round compound offers the perfect blend of privacy, space, and flexibility. The post-and-beam main house features four bedrooms and combines timeless character with functional design, ideal for everyday living or seasonal enjoyment. A separate two-bedroom guest house with a welcoming farmer's porch is thoughtfully sited to ensure privacy and independence, complete with its own driveway and parking. The detached garage, with a loft above, adds even more versatility--ideal for storage or future finished space. Situated on one of the largest parcels in the Smith Hollow Association, the property enjoys a tranquil, park-like setting. With direct access to the bike path at the end of the road, you're just minutes from Edgartown and all down-island amenities. More than just a house--this is a place to call home.
Full Property Details
Full Property Details for 36 Smith Hollow Dr
General
- Price: $1,985,000
- Taxes: $4,700 (2025)
- Status: Active
- Type: Single Family
- Source: MarthasVineyardFlex
- MLS ID: 32500312
- Updated: 9/12/2025
- Added to Site: 127 day(s) ago
Interior
- Number of Rooms: 11
- Appliances: Electric Water Heater
- Flooring: Carpet, Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 6
Additional Information
- Pool Description: None
Exterior
- Exterior Features: Garden, Outdoor Shower
Parking
- Garage: Yes
- Garage Spaces: 1
Location
- County: Dukes
- Driving Directions: No drive-bys, owners in residence.
Heating & Cooling
- Cooling Type: None
Utilities
- Sewer: Septic Tank
- Water: Well
Structural Information
- Construction: Shingle Siding
- Basement Desc.: Finished, Interior Entry, Full
- Roof: Shingle
- Stories/Levels: 2
- Square Feet: 2,836
- Year Built: 1985
Lot Features
- Lot Size (Acres): 1.7
- Lot Size (Sq. Ft.): 74,052
- Lot Size Source: Assessor
- Street/Road Desc.: Paved
- Road Maintenance: Assoc Maintained
- Zoning: R60
Financial Considerations
- Tax Amount: $4,700
- Tax Year: 2025
Disclosures and Reports
- APN: 11221
- Property ID: 11221
Listed by Katherine Donahue
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 36 Smith Hollow Dr —
Katherine Donahue
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 36 Smith Hollow Dr
School Districts:Martha's Vineyard School District, Edgartown School District
| Name | Grades | Distance |
|---|---|---|
Edgartown Elementary School 35 Robinson Road, Edgartown, MA 02539 | PK-8 | 2.4 mi |
Marthas Vineyard Regional High School 100 Edgartown-Vineyard Haven R, Oak Bluffs, MA 02557 | 9-12 | 1.9 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 36 Smith Hollow Dr
Tax History
Tax History for 36 Smith Hollow Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,700
16%
$1,773,700
11%
2024
$4,060
17%
$1,592,000
15%
2023
$3,478
1%
$1,380,300
22%
2022
$3,438
-9%
$1,134,700
-2%
2021
$3,783
16%
$1,153,500
19%
2020
$3,250
-16%
$970,000
-3%
2019
$3,854
9%
$995,800
9%
2018
$3,550
20%
$917,300
10%
2017
$2,962
10%
$834,300
12%
2016
$2,702
13%
$746,400
8%
2015
$2,397
-8%
$690,700
-2%
2014
$2,605
—
$704,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 36 Smith Hollow Dr
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- Single Family
- Active
- Updated 2 days ago
- 4Beds
- 3Total Baths
- 3,268Sq. Ft.
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- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 1Total Bath
- 1,033Sq. Ft.
Listed by Alice Pierce (781) 749-4300
- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 2Total Baths
- 3,192Sq. Ft.
- Single Family
- Active
- Updated 2 days ago
- 4Beds
- 3Total Baths
- 3,268Sq. Ft.
- Single Family
- Active
- Updated 3 days ago
- 3Beds
- 3Total Baths
- 2,354Sq. Ft.
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- Single Family
- Active
- Updated 3 days ago
- 2Beds
- 3Total Baths
- 1,500Sq. Ft.
- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 1Total Bath
- 1,086Sq. Ft.
- Single Family
- Active
- Updated 2 days ago
- 1Bed
- 2Total Baths
- 1,898Sq. Ft.
- Single Family
- Active
- Updated 16 hours ago
- 5Beds
- 2Total Baths
- 1,428Sq. Ft.
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36 Smith Hollow Drive, Edgartown, MA 02539 (MLS# 32500312) is a Single Family property with 6 bedrooms, 2 full bathrooms and 1 partial bathroom. 36 Smith Hollow Drive is currently listed for $1,985,000 and was received on September 12, 2025. Want to learn more about 36 Smith Hollow Drive? Do you have questions about finding other Single Family real estate for sale in Edgartown? You can browse all Edgartown real estate or contact a Coldwell Banker agent to request more information.