$5,995,000

20 Sunnyside Ave Vineyard Haven, MA 02568

Vineyard Haven Neighborhood

Estimated payment $35,555/month

Total Views 1,602
3 Beds
3 Baths
2,280 Sq Ft
$2,629 Price per Sq Ft

Highlights

  • Waterfront
  • 0.82 Acre Lot
  • Wood Flooring
  • Tisbury Elementary School Rated A-
  • Deck
  • Patio

About This Home

Waterfront Estate with Deep-Water Dock & Private Beach.

Experience an exceptional Martha’s Vineyard waterfront lifestyle at this rare Lagoon Pond offering, ideally located just minutes from Vineyard Haven’s vibrant harbor, restaurants and shops. The property features a private deep-water dock—ideal for the avid boater—along with its own sandy beach for effortless access to the water.

The refined residence was completely renovated in 2022, with interiors by Nicole Hogarty Designs. Filled with natural light and expansive water views, the home is complemented by beautifully landscaped grounds and mature specimen trees, creating a private setting for outdoor living and entertaining.

Amenities include a professional-grade bocce court, cold plunge, large hot tub, and classic Island outdoor shower. A separate, stylish party barn provides a versatile setting for everything from intimate gatherings to summer celebrations.

Offering an uncommon combination of privacy, waterfront access, boating, and proximity to downtown Vineyard Haven, this distinctive estate captures the best of Island living—from mornings on the water to sunset cocktails on the dock.

Listing Agent

Peyton Wallace

Studio Realty Listed on: 08/22/2026

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $29,733

Year Built

  • Built in 2004 | Remodeled in 2022

Lot Details

  • 35,719 Sq Ft Lot
  • Waterfront
  • Property is zoned R20

Interior Spaces

  • 2,280 Sq Ft Home
  • Wood Flooring

Bedrooms and Bathrooms

  • 3 Bedrooms
  • 3 Full Bathrooms

Outdoor Features

  • Deck
  • Patio

Utilities

  • Septic Tank
  • Cable TV Available

Listing and Financial Details

  • Tax Lot 3
  • $2,414,100 per year additional tax assessments

Home Details

Home Type

Single Family

Est. Annual Taxes

$29,733

Year Built

Built in 2004 | Remodeled in 2022

Lot Details

0.82 Acres

Listing Details

  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Frontage: Waterfront
  • Lot Features: Beautifully planted yard and grounds
  • LotSizeAcres: 0.82
  • Co List Office Mls Id: 1053
  • Building Area Total: 2280
  • Has Fireplace?: No
  • Effective Year Built: 2022
  • Year Built: 2004
  • reviewed: Yes
  • Special Features: None
  • Year Built: 2004
  • Year Renovated: 2022

Interior Features

  • Appliances: Stove: Y, Washer: Y
  • Has Basement: Partial Crawl for Storage and Utilities
  • Full Bathrooms: 3
  • Total Bedrooms: 3
  • Fireplace Features: 1 - Woodburning
  • Flooring: Hardwood/Tile
  • Interior Amenities: AC,Ins,OSh, Floor 1: Beautiful open great room with kitchen, living and dining. Opens to a deck with views for sun or dining. There is also a den with sliding door and full bath., Floor 2: Three bedrooms and two full baths - the primary has its own private luxurious bathroom. Laundry is tucked off the hallway.

Exterior Features

  • Pool Private: No
  • Exterior Features: PvtBch, PubBch, Deck, H/Tub, Patio, WViews
  • Other Structures: Stairs lead to deepwater dock and sandy beach along the shoreline. Detached party barn with bocce court provides bonus rec. space and storage in winter. Additional shed near the barn and entrance to the property.

Garage/Parking

  • Parking Features: Shell driveway

Utilities

  • Heating: GFHA
  • Sewer: Septic Tank
  • Utilities: Cbl
  • Water Source: Town

Lot Info

  • Lot Size Sq Ft: 35719
  • Zoning: R20

Multi Family

  • Number Of Units Furnished: Unfurnished

Tax Info

  • Tax Annual Amount: 29733
  • Tax Lot: 3
  • Tax Map Number: 16N
  • Tax Other Annual Assessment Amount: 2414100
  • Tax Year: 2026

Map

Range of Values:

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Value Increase
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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Tax History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $30,758 $4,063,100 $2,552,000 $1,511,100
2024 $23,737 $2,974,600 $1,893,500 $1,081,100
2023 $22,148 $3,025,700 $1,903,600 $1,122,100
2022 $19,243 $2,211,887 $1,091,287 $1,120,600
2021 $17,389 $1,896,300 $1,033,900 $862,400
2020 $16,705 $1,790,500 $1,033,900 $756,600
2019 $16,807 $1,832,800 $1,033,900 $798,900
2018 $13,557 $1,399,200 $821,900 $577,300
2017 $12,940 $1,420,400 $879,700 $540,700
2016 $11,946 $1,304,200 $839,100 $465,100
2015 $12,644 $1,417,500 $952,400 $465,100
Source: Public Records

Property History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Event Price List to Sale Price per Sq Ft Prior Sale
08/22/2026 08/22/26 For Sale $5,995,000 +178.8% $2,629 / Sq Ft
08/23/2017 08/23/17 Sold $2,150,000 -7.5% $925 / Sq Ft View Prior Sale
06/15/2017 06/15/17 Pending -- -- --
03/10/2017 03/10/17 For Sale $2,325,000 -- $1,000 / Sq Ft
Source: LINK (Vineyard)

Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Type Sale Price Title Company
Quit Claim Deed $2,150,000 --
Deed $980,000 --
Source: Public Records

Mortgage History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Status Loan Amount Loan Type
Open $1,000,000 Stand Alone Refi Refinance Of Original Loan
Open $1,586,000 Adjustable Rate Mortgage/ARM
Closed $1,619,900 Adjustable Rate Mortgage/ARM
Closed $1,600,000 No Value Available
Source: Public Records

Source: LINK (Vineyard)

MLS Number: 44868

APN: TISB-000016N-000000-000003

Massachusetts Dukes County Vineyard Haven 02568 Vineyard Haven

20 Sunnyside Ave, Vineyard Haven, MA

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Listing Agent
Peyton Wallace
Studio Realty
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