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99 Cooke Street

$3,895,000

Downtown, Edgartown, MA 02539

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4 beds

4 baths

6 rooms

1,590 SqFt

MLS #44161

LUXURY COTTAGE-STYLE LIVING IN THE VILLAGE – WITH A POOL! This updated classic cottage is located in the heart of Edgartown Village, less than a quarter mile to Main Street. Upon arrival, you are greeted by a spacious porch and elegant French door entry that lead you into the dramatic foyer. The open living plan with kitchen, dining, and living area is light and bright. The first floor opens out onto a charming brick terrace and fenced backyard - the ideal location for outdoor living and entertaining. The swimming pool is the centerpiece of the backyard space. In this delightful cottage, there are a total of FOUR BEDROOMS, each with a full bath. A first-floor primary bedroom suite for comfort and convenience. An elegant staircase leads upstairs to two spacious bedrooms, each with its own private bath. Separating the bedrooms is a charming balcony lined with a wall of ample storage closets, blending style with exceptional functionality. The partially finished lower level includes over 500 square feet of finished space, including a 4th bedroom with its own sitting area, a full bath, and a separate laundry/utility room. There is over 2,000 sq feet of living space in this in-town cottage. Enjoy the benefits of in-town living with easy access to the village’s vibrant restaurant and shopping scene, and also take advantage of the strong rental history.

Property highlights

Furnished

Public Beach

Deck

Hot Tub

Private Pool

Town Sewer

Cable

Town Water

Property Details

Association Fee:
Association Fee Includes:
Basement:
Full finished basement with large bedroomfull bathroomlaundry area and mechanical room
Fireplace Features:
Electric
Flooring:
wood/tile
Foundation Types:
poured foundation
Frontage Type:
None
Heating:
Heat Pump
Interior Features:
A,Ins,MiniSplit,OShFloor 1: Open floor concept with vaulted ceiling as you walk into the home with dining area, living room and kitchen. Bedroom with private bathroomFloor 2: 2 large bedrooms each with their own private bathroom.
Link MLS Comments:
Entering Edgartown - Upper Main Street to Cooke Street #99
Lot Features:
Beautifully landscaped with mature plantings
Parking Features:
Ample parking
Possible Use:
Assessed Building Value:
1242300.00
Assessed Land Value:
1267400.00

Price History

March 02, 2026
$3,895,000

Tax Information

This property was most recently assessed in 2026. It has been assessed at a value of $2,509,700. The annual tax responsibility for this property is $6,225.

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©2026 LINK, All Rights Reserved. Not responsible for misinformation or typographical errors. Prices are subject to change without notice. Listed by Wallace & Co. Sotheby's.