For sale

$3,295,000

Est. $18,861/mo —

•

2,330

sq ft

29 & 33 Lagoon Pond Rd, Vineyard Haven, MA 02568

About this home

Rare downtown Vineyard Haven compound offering! A unique opportunity to own two separate properties offered together just moments from the ferry, harbor, restaurants, and shops. 33 Lagoon Pond Road is a newly built 3BR/3BA home featuring an open floor plan, designer kitchen with quartz countertops, custom tile baths, water views, private backyard, spacious deck, attached two-car garage, and strong rental history. Complementing 33 Lagoon Pond Road, is 29 Lagoon Pond Road originally built in 1950 and beautifully renovated in 2020. This 2BR/1BA cottage with a private patio and outdoor shower, is ideal for guests, extended family, employee housing, or additional rental income. A rare highlight is the oversized rear parking lot accommodating approximately 10 vehicles--an exceptional amenity in downtown Vineyard Haven. Whether you're seeking a family compound, investment property, or luxury in-town retreat with unmatched flexibility and income potential, this one-of-a-kind offering is not to be missed.

Single-familyProperty Type

2025Year Built

0.28 acresLot Size

$1,414Price/Sq.Ft.

2 garage spacesParking

Listed by Madelyn Silvia • Wallace & Co. Sotheby's International Realty

Listing updated: Oct 19, 2026 at 07:24pm

Redfin checked: a minute ago

•Source:CCIMLS #22603560

Payment calculator

$18,861 per month

Principal and interest$17,520

Property taxes

$929

HOA dues

Home insurance

$412

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (9)

OPEN SAT, 11:30AM TO 1PM3D WALKTHROUGH
$575,000
3 beds1 bath888 sq ft
28 Avalon Dr, East Falmouth, MA 02536
0.27 acre lot • 3 parking spots • Built 1956
OPEN SAT, 11:30AM TO 1PM
$1,300,000
3 beds2.5 baths2,486 sq ft
14 Bayshore Dr, Mashpee, MA 02649
0.45 acre lot • Garage • Pool
OPEN SAT, 12PM TO 1:30PM
$1,475,000
3 beds2.5 baths2,624 sq ft
64 Randolph St, Teaticket, MA 02536
7,200 sq ft lot • 2 garage spots • Built 1975
OPEN SUN, 11AM TO 1PM
$565,000
2 beds1.5 baths1,620 sq ft
97 Prince Henry Dr, E Falmouth, MA 02536
0.23 acre lot • 4 parking spots • Built 1957
OPEN SUN, 1PM TO 3PM
$595,000
3 beds2.5 baths1,560 sq ft
350 Old Barnstable Rd Unit 3A, East Falmouth, MA 02536
$520 HOA • 2 parking spots • Built 2004
OPEN SUN, 1PM TO 3PM
$1,195,000
3 beds1.5 baths912 sq ft
11 Stanley St, Oak Bluffs, MA 02557
0.35 acre lot • 6 parking spots • Built 1986
OPEN SUN, 1PM TO 3PM
$800,000
3 beds2 baths2,442 sq ft
3 Viber Ln, E Falmouth, MA 02536
0.53 acre lot • Garage • Built 1982
OPEN SUN, 1PM TO 3PM
$800,000
3 beds2 baths2,442 sq ft
3 Viber Ln #1, East Falmouth, MA 02536
Garage • Built 1982 • Listed 109 days
OPEN NOV 17, 1PM TO 3PM
$2,095,000
4 beds4 baths2,876 sq ft
18 Sylvan Ave, Vineyard Haven, MA 02568
0.34 acre lot • 3 parking spots • Built 2005

Around this home

Schools

K - 12
Preschool & daycare

Tisbury Elementary School

Public PreK-8 • Assigned • 0.4mi

4/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 2.5mi

6/10

Provided by GreatSchools

About Martha's

Vineyard

Martha's Vineyard, located between Vineyard Sound and Nantucket Sound, is a coastal and rural West Tisbury neighborhood with wooded back roads and broad farm fields. The neighborhood’s character concentrates around the West Tisbury Village Center at State Road and Edgartown–West Tisbury Road, where the library lawn, small shops, and a low-key town-green rhythm set the pace. Architecture leans to shingled cottages, classic capes, and working farm outbuildings tucked behind stone walls. The Polly Hill Arboretum adds curated woodland paths and rare plantings to the island’s natural palette. The Grange Hall anchors a calendar of community gatherings, while Alley’s General Store keeps the everyday essentials distinctly local. Long Point Wildlife Refuge and nearby beaches frame a lifestyle shaped by trails, ponds, and salt air.

Provided by Walk Score and Local Logic

Offer insights

29 & 33 Lagoon Pond Rd · $3,295,000

Strong offer

$3.27M and above

75% chance or better to win

Why $3.27M+ is a strong offer

DAYS ON MARKET

The average home goes pending in 53 days.

SALE-TO-LIST

Most homes are selling 2% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Hardwood, vinyl, and tile flooring
Water heater

Bathrooms
4 full bathrooms

Flooring
Hardwood
Vinyl
Tile

Heating & cooling
Heating present
Cooling present

Sale and tax history for 29 & 33 Lagoon Pond Rd

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2023

$4,107 (+15.5%)

$342,700 + $218,300

$561,000

2022

$3,555 (+20.2%)

$225,600 + $183,000

$408,600

2021

$2,957 (−7.4%)

$225,600 + $96,900

$322,500

2020

$3,194 (+5.9%)

$225,600 + $116,700

$342,300

2019

$3,017 (+14.2%)

$215,800 + $113,200

$329,000

2018

$2,642 (+0.4%)

$205,600 + $74,000

$279,600

2017

$2,631 (+10.4%)

$207,700 + $81,100

$288,800

2016

$2,384 (+24.2%)

$179,200 + $81,100

$260,300

2015

$1,919

$141,100 + $74,000

$215,100

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

6,534 Sq. Ft.

Year renovated

—

Finished Sq. Ft.

650

Unfinished Sq. Ft.

—

Total Sq. Ft.

650

Year built

1950

Style

Single Family Residential

County

Dukes County

APN

2449719

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 23, 2026.

Climate risks

9/10 Flood Factor

Estimated 80%+ chance of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 88° expected this year, 20 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Vineyard Haven, MA • 02568

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

80/ 100

Very good sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.4 hrs

3.1 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 29 & 33 Lagoon Pond Rd

$3,183,458

$112K under list price of $3.30M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $1.2M to $2.0M.

SOLD OCT 14, 2026
$1,980,000 Last sold price
4 beds3 baths2,730 sq ft
5 Pine Tree Ln, Vineyard Haven, MA 02568
$689/sq ft
smaller lot
98 years older
SOLD OCT 19, 2026
$1,700,000 Last sold price
3 beds3.5 baths2,376 sq ft
28 Grovedale Rd, Oak Bluffs, MA 02568
$699/sq ft
smaller lot
2 years older
SOLD MAY 28, 2026
$2,000,000 Last sold price
4 beds3.5 baths2,690 sq ft
151 Tashmoo Ave, Tisbury, MA 02468
$671/sq ft
larger lot
3 years older
SOLD OCT 16, 2026
$2,050,000 Last sold price
3 beds2 baths1,425 sq ft
312 E Chop Dr, Vineyard Haven, MA 02568
$25/sq ft
smaller lot
125 years older
SOLD JUN 12, 2026
$1,187,500 Last sold price
4 beds2 baths1,764 sq ft
54 Columbian, Oak Bluffs, MA 02557
$741/sq ft
smaller lot
36 years older
SOLD MAR 16, 2026
$1,225,000 Last sold price
4 beds2 baths1,566 sq ft
344 Greenwood Ave, Vineyard Haven, MA 02568
$632/sq ft
44 years older

Rental earnings

Est. $1,660 per month, based on comparable rentals

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Nearby similar homes

$1,200,000

4 beds3 baths2,304 sq ft

33 Alyssa Ln, Vineyard Haven, MA 02568

Large side deck • High ceilings • Wood floors

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85 feet of frontage • Private staircase • Expansive views

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Historic character • Period details • Light filled kitchen

New listings for sale in 02568

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Expansive deck • Mature plantings • Evergreen trees

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Details provided by CCIMLS and may not match the public record. Learn more.

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