
99 Old Purchase Road Edgartown — Photo 1 of 34
Recent Drop: $75,000
$1,775,000
Investment Analysis — 99 Old Purchase Road
Edgartown, MA 02539
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 0.79% cap rate and $14,091/yr in estimated NOI at the $1,775,000 list price. Adjust every assumption in the calculator below.
Beds
4
Baths
2.5
SqFt
2,064
Style
Single Family
Built
1985
Set at the end of a cul-de-sac, this property offers a peaceful setting on .71 acres, with easy access to more than 25 acres of Land Bank conservation land. Morning Glory Farm is just a short distance away, offering a wonderful connection to the seasonal beauty and character of the Island. The bike path, Edgartown Village, and South Beach are also nearby, providing an easy balance of privacy and convenience. Filled with natural light, the post-and-beam home features a spacious kitchen with a large center island, walk-in pantry, and garden access. The dining area opens to a generous deck, while the sunken living room features cathedral ceilings, a floor-to-ceiling brick fireplace, and views of the surrounding landscape. A first-floor bedroom and full bath offer flexibility for guests. Upstairs, the primary suite includes a half bath, along with two additional bedrooms and a full bath. Established gardens, an outdoor shower, and expansive decking extend the living space outdoors. A basement provides additional storage and overflow space. Town sewer allows for expansion to as many as seven bedrooms, offering meaningful future potential in a private and well-connected Edgartown setting.
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 MLS and other third-party data may be inaccurate or out of date.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
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Water Heater • Dishwasher • Range • Refrigerator • Washer • Dryer • Range Hood
Neighborhood
Public Transportation • Walk/Jog Trails • Golf • Bike Path • Conservation Area
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl Main,FirstSkylight, Ceiling Fan(s), Flooring - Stone/Ceramic Tile, Window(s) - Picture, Deck - Exterior, Exterior Access, Slider, Lighting - Overhead, Half Vaulted Ceiling(s)
Dining Room
Lvl Main,FirstWood / Coal / Pellet Stove, Flooring - Wood, Exterior Access, Slider
Kitchen
Lvl Main,FirstFlooring - Hardwood, Pantry, Countertops - Stone/Granite/Solid, Kitchen Island, Deck - Exterior, Exterior Access, Slider, Lighting - Overhead
Primary Bedroom
Lvl SecondBathroom - Half, Skylight, Flooring - Hardwood, Closet - Double
Bedroom 2
Lvl SecondBedroom 3
Lvl SecondCloset, Flooring - Wood
Bedroom 4
Lvl Main,FirstCloset, Flooring - Hardwood
Bathroom 1
Lvl Main,FirstBathroom - Full, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile, Lighting - Overhead
Bathroom 2
Lvl SecondBathroom - Full, Bathroom - Tiled With Shower Stall, Skylight, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Double Vanity, Lighting - Overhead
Bathroom 3
Lvl SecondBathroom - Half, Skylight, Flooring - Laminate, Countertops - Stone/Granite/Solid, Lighting - Overhead
Property History
$1,775,000
Was $1,850,000
Sep 5, 2026
MLS® 73531632
$1,850,000
Jun 8, 2026
MLS® 73531632
$1,895,000
Mar 31, 2026
MLS® 73357805
$1,895,000
Apr 10, 2025
MLS® 73357805
Listing Agent: Stephanie Roache
Listing Office: Donnelly + Co.
MLS® Number: 73531632








