Edgartown, MA 02539 15 Twenty First Street North

$2,675,000

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Presented By: Jen O'Hanlon with Compass LLC - 508-212-8278
  • MLS# 44320
  • 05/21/2026
  • Request Tour
  • Request Info
  • Beds • 4
  • Full/Half Baths • 5 / 3
  • SQFT • 3,740

Home Details

Located on a quiet street just moments from Edgartown Village, this versatile compound offers a rare combination of privacy, flexibility, and proximity to some of the Island’s most treasured outdoor amenities. Set on over a half-acre, the property features a main residence and a detached guest house, thoughtfully positioned with separate driveways and a natural buffer of mature trees. The main house offers a comfortable and inviting interior, highlighted by a bay window and a spacious open kitchen and dining area with granite countertops, custom cabinetry, and direct access to the deck. A sunken living room offers separation while maintaining an open flow. The main level includes a primary bedroom and an additional bedroom, while the second floor offers a third bedroom, a full bathroom, and flexible living space. The finished lower level offers approximately 790 sq ft of additional finished space, including a recreation area, den, and full bathroom, along with approximately 525 sq ft of unfinished storage. Outdoor living is equally inviting, with a deck off the kitchen leading to the heated pool and patio. The space includes a pool house with half bath, an outdoor shower, and ample room for dining and lounging, surrounded by hydrangeas. There is ample yard space behind both the main house and guest house, ideal for games, outdoor entertaining, or simply enjoying the privacy and natural setting. The guest house, built in 2011, is thoughtfully separated from the main house by its own private driveway and mature landscape screening. It features a spacious living area, a main-level bedroom, and additional finished space upstairs, along with full bathrooms on both levels. There is also a half bath with laundry, a one-car garage, and a full basement. At the end of 21st Street you’ll find direct access to over 150 acres within the Caroline Tuthill Preserve, as well as the Boulevard landing on Sengekontacket Pond — perfect for kayaking, paddle boarding, or boating. Edgartown Village is approximately 1.5 miles away. A unique opportunity with an established rental history — details upon request. Furniture available for separate purchase.
Presented By: Jen O'Hanlon with Compass LLC - 508-212-8278

Interior Features for 15 Twenty First Street North

Bedrooms

Main Level Bedrooms2
Total Bedrooms4

Bathrooms

Half Baths3

Other Interior Features

BasementApproximately 790 s.f. of additional finished space with large recreation area, den, and full bathroom, plus a 525 s.f. unfinished room with bulkhead for easy access for storing outdoor furniture.
Fireplace Features1
Fireplace Y/NNo
FlooringHardwood/Tile/Luxury Laminate
Furnished Y/NUnfurnished
Interior AmenitiesMedia, OSh, Floor 1: Open kitchen and dining area with granite countertops, custom cabinetry. Primary bedroom and additional bedroom., Floor 2: 1 Bedroom, Full Bathroom + additional living space.

General for 15 Twenty First Street North

AppliancesStove: Yes, Electric, Washer: Yes
Building Area UnitsSquare Feet
CityEdgartown
Full Baths5
HeatingGFHW
Lot Size Square Feet23087
MLS Area2
Other StructuresPool house with bathroom and outdoor shower. Heated inground pool.
Property SubtypeSingle Family Residence
Property Type1 Family
SewerSeptic Tank
Standard StatusActive
StatusA
Tax Annual Amount5878.84
Tax Assessed Value1969400
Tax Lot98
Tax Year2026
TaxOtherAnnualAssessmentAmount401100
Total Rooms12
UtilitiesCbl
ViewNone, Trees/Woods
Year Built1993
Year Built Effective2011
ZoningR20

Exterior for 15 Twenty First Street North

Building Area Total3740
Exterior AmenitiesDeck, P/Pool, Porch, Garden
Foundation DetailsPoured concrete
Frontage TypeNone
Lot FeaturesYes
Lot Size Acres0.53
Lot Size Area0.53
Parking Features6
Water SourceWell

Additional Details

Price History

Ron Jackson

Agent
Price $2,675,000
MLS#44320
List Date 05/21/2026
Property Type Single Family
Phone 617.733.0109
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