Active Under Contract
20 Days on market
105 Whalers Walk Edgartown — Photo 1 of 42

105 Whalers Walk Edgartown — Photo 1 of 42

$2,395,000

Investment Analysis — 105 Whalers Walk

Edgartown, MA 02539 — Edgartown

Based on HUD Small Area Fair Market Rent for Dukes County, MA, a 4-bedroom in 02539 carries an estimated $3,430/mo in gross rent — about a 1.14% cap rate and $27,415/yr in estimated NOI at the $2,395,000 list price. Adjust every assumption in the calculator below.

View Standard Listing

Beds

4

Baths

3

SqFt

1,968

Style

Single Family

Built

1987

Renovated Edgartown Retreat With Pool, Terrace + Outdoor Entertaining Pavilions - Designed for relaxed indoor-outdoor living, this recently renovated four-bedroom, three-bath Edgartown home is set on just under an acre and centered around an exceptional new backyard retreat. From quiet mornings by the pool to leisurely dinners beneath the pergolas, the property offers a welcoming setting for enjoying the Vineyard lifestyle. The pool features a sun shelf and built-in seating and is surrounded by an expansive stone terrace with generous room for lounging and entertaining. Two pergola pavilions create a stylish open-air living area with dedicated lounge and dining spaces, while an outdoor shower completes the resort-like setting. An expanded rear deck provides an easy connection between the home and its impressive outdoor amenities. Inside, thoughtful renovations have created bright, comfortable spaces for everyday living and gathering. The redesigned kitchen features crisp white cabinetry, marble countertops, stainless-steel appliances, and an extended marble breakfast bar that connects the kitchen and dining areas while providing additional seating and workspace. Hardwood floors run throughout both levels, and air conditioning has been added for year-round comfort. The first floor also includes a renovated full bath and a new laundry room with front-loading appliances. Upstairs, a newly created primary suite offers privacy and a beautifully finished bath with a large custom-tiled shower. Two additional bedrooms feature new hardwood floors and fresh paint and share a completely renovated full bath. Further improvements include a new front stoop, Bluetooth-controlled irrigation, and a two-car garage with its own rear deck and outdoor shower, adding convenience for island living. Connected to town sewer with capacity for seven bedrooms, the property presents valuable future expansion possibilities. An established rental income history offers additional flexibility for buyers interested in combining personal enjoyment with income-producing potential. With its renovated interiors, exceptional pool setting, multiple outdoor gathering spaces, and room to envision what comes next, this distinctive Edgartown retreat is ready for memorable days and evenings on Martha's Vineyard.

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 1,968 sq ft principal dwelling). Lot size: 41,680 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Estimates — not financial advice

These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.

Property Details

Financials

Original Price$2,395,000
Annual Taxes$3,867

Parking

Garage2
Off-Street6

Interior Specifications

Total Rooms7
Fireplaces2
Flooring--
BasementNone

Climate & Utilities

HeatingForced Air, Oil
CoolingHeat Pump
WaterPrivate
SewerPublic Sewer

Building & Exterior

Construction--
Roof--
FoundationConcrete Perimeter
ZoningR60

Property & Lot

Acres0.96
SqFt Lot41,680
Lot FeaturesWooded, Cleared, Level

Geography

Property History

Listed
$2,395,000

Aug 23, 2026

MLS® 73567153

Terminated
$2,395,000

Aug 17, 2026

MLS® 73548852

Listed
$2,395,000

Jul 13, 2026

MLS® 73548852

Terminated
$2,395,000

Jul 8, 2026

MLS® 73503128

Listed
$2,395,000

Apr 16, 2026

MLS® 73503128

Listing Provided By

Listing Agent: Ekaterina Brush

Listing Office: Compass

MLS® Number: 73567153