Back to Search
Active
120 Days on market
99 Old Purchase Road Edgartown — Photo 1 of 34

99 Old Purchase Road Edgartown — Photo 1 of 34

Recent Drop: $75,000

$1,850,000
$1,775,000

$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.

View Standard Listing

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

Original Price$1,850,000
Annual Taxes$2,791
HOA Fee$1200

Parking

Garage0
Off-Street4

Interior Specifications

Total Rooms7
Fireplaces1
FlooringWood, Tile, Flooring - Stone/Ceramic Tile
BasementFull, Interior Entry, Bulkhead

Climate & Utilities

HeatingElectric Baseboard, Propane, Pellet Stove, Ductless
CoolingDuctless
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionConventional (2x4-2x6)
RoofShingle
FoundationConcrete Perimeter
ZoningR60

Property & Lot

Acres0.71
SqFt Lot30,927
Lot FeaturesWooded, Cleared, Level

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

Second
Primary BedroomBedroom 2Bedroom 3Bathroom 2Bathroom 3
Main,First
Living RoomDining RoomKitchenBedroom 4Bathroom 1
Living Room
Lvl Main,First

Skylight, 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,First

Wood / Coal / Pellet Stove, Flooring - Wood, Exterior Access, Slider

Kitchen
Lvl Main,First

Flooring - Hardwood, Pantry, Countertops - Stone/Granite/Solid, Kitchen Island, Deck - Exterior, Exterior Access, Slider, Lighting - Overhead

Primary Bedroom
Lvl Second

Bathroom - Half, Skylight, Flooring - Hardwood, Closet - Double

Bedroom 2
Lvl Second
Bedroom 3
Lvl Second

Closet, Flooring - Wood

Bedroom 4
Lvl Main,First

Closet, Flooring - Hardwood

Bathroom 1
Lvl Main,First

Bathroom - Full, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile, Lighting - Overhead

Bathroom 2
Lvl Second

Bathroom - Full, Bathroom - Tiled With Shower Stall, Skylight, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Double Vanity, Lighting - Overhead

Bathroom 3
Lvl Second

Bathroom - Half, Skylight, Flooring - Laminate, Countertops - Stone/Granite/Solid, Lighting - Overhead

Property History

Price Drop
$1,775,000

Was $1,850,000

Sep 5, 2026

MLS® 73531632

Listed
$1,850,000

Jun 8, 2026

MLS® 73531632

Expired
$1,895,000

Mar 31, 2026

MLS® 73357805

Listed
$1,895,000

Apr 10, 2025

MLS® 73357805

Listing Provided By

Listing Agent: Stephanie Roache

Listing Office: Donnelly + Co.

MLS® Number: 73531632