43 Sengekontacket Road, Oak Bluffs, MA 02557
Property image
Property image
FOR SALE
2.9 ACRES

$5,495,000

Original price: $5,995,000
  • 3 Beds
  • 3 Baths
  • 2,234 sqft (on 2.90 acres)

43 Sengekontacket Road, Oak Bluffs, MA 02557

Est. Mortgage $30,238/mo*
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Home Highlights

Single-Family Home
Built in 1980
2.9 acre lot
$2,460/sqft
Garage

Local Information

  • Map ViewExplore the area around 43 Sengekontacket Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside from boating, the swimming and clamming in the immediate waters are sublime. Expansive lawns slope down to the water on three sides of the residence - one of the most enchanting settings on the waterfront on Martha's Vineyard.
Last check for updates: about 10 hours ago
Listing courtesy of Peyton Wallace, (508) 687-2699
Studio Realty LLC
Source: CCIMLS, MLS#22603599
Also Listed on CCIMLS, LINK, LINK.

Home Details for 43 Sengekontacket Road

Interior Features

Interior Details
Basement: PartialNumber of Rooms: 6
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3
Appliances & Utilities
Appliances: Electric, Water Heater
Heating & Cooling
Heating: ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Electric
Windows, Doors, Floors & Walls
Flooring: Wood, Tile
Levels, Entrance, & Accessibility
Stories: 1Floors: Wood, Tile

Exterior Features

Exterior Home Features
Roof: Asphalt ShingleExterior: Outdoor Shower
Parking & Garage
Number of Garage Spaces: 1Has a GarageNo Attached GarageHas Open ParkingParking Spaces: 4Parking: Detached,Garage Door Opener,Driveway,Unpaved,Gravel
Frontage
WaterfrontWaterfront: Waterview, Waterfront, OtherOn Waterfront
Water & Sewer
Water Body: Other, Salt

Days on Market

Cumulative Days on Market: 22Days on Market: 46

Property Information

Year Built
Year Built: 1980
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Shingle Siding, Wood Siding
Property Information
Parcel Number: OAKB M:0047 B:0002 L:000

Price & Status

Price
List Price: $5,495,000Price Per Sqft: $2,460

Active Status

MLS Status: Active

Location

Direction & Address
City: Oak Bluffs

Agent Information

Listing Agent
Listing ID: 22603599

Building

Building Area
Building Area: 2234 Square Feet

HOA

Has an HOA

Lot Information

Lot Area: 2.9 Acres

Listing Info

Special Conditions: None

Miscellaneous

BasementMls Number: 22603599Showing Requirements: Call Listing Office, Call Listing Agent

Additional Information

HOA Amenities: Clubhouse,Tennis Court(s),Common Area,Road Maintenance

Around this home

What Locals Say about Oak Bluffs

At least 18 Trulia users voted on each feature.

  • 96 % Say it's dog friendly

  • 86 % Say kids play outside

  • 83 % Say yards are well-kept

  • 79 % Say it's walkable to restaurants

  • 79 % Say car is needed

  • 78 % Say people would walk alone at night

  • 78 % Say it's walkable to grocery stores

  • 73 % Say there's wildlife

  • 73 % Say they plan to stay for at least 5 years

  • 70 % Say there's holiday spirit

  • 67 % Say it's quiet

  • 62 % Say parking is easy

  • 59 % Say neighbors are friendly

  • 47 % Say there are community events

  • 44 % Say there are sidewalks

  • 36 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Easy to walk dogs"
    0
    Flag
  • P5j4f84ncw
    "Local people, well known community,quite,hard working people,solid business,good schools,hospitality,new opportunities,security and safety place to leave. "
    0
    Flag
  • Adrianalleyne
    "Oak Bluffs has a vibrant history and continues to be a bastion of African American culture. It’s worth checking out some of the many cultural sites in Oak Bluffs and throughout the island "
    0
    Flag
  • Trulia User
    "Oak Bluffs is a charming town with a bustling summer harbor and lovely shopping district. It’s a beautiful place to live. "
    0
    Flag
  • Jrheneeb
    "I love it here. It’s beautiful and the people are amazing. It’s a great place To come relax and unwind. "
    0
    Flag
  • Kayceesmith27
    "I take the bus to and from work . Car for longer distances. Boat to get to the main land which is 45min ride."
    0
    Flag
  • Andrea H.
    "This is fantasy island. It is not like the real world it's not fast paced. we say we're on island time. there's hardly any crime it's safe for kids. and it's a good community."
    0
    Flag
  • tkurian
    "I own a property in Oak Bluffs"
    0
    Flag
  • Kristin Z.
    "We live here year round in what most people think is a vacation paradise for the rich and famous. But in actuality it is one of the best communities to live in terms of caring wonderful neighbors and exciting intellectual stimulation throughout the winter in the form of performances, music groups, communities by interests. "
    0
    Flag
  • Island R. E.
    "This is a lovely and desirable area close to town and everything the island has to offer."
    1
    Flag

Market trends in Oak Bluffs

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
58
4MoM

Home Value

Trulia Estimate
$5.15M
Since last month
Decreased$654K (-11.3%)
Since last year
Increased$984K (+23.6%)
Since last sale
Increased$2M (+58.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +168% in the last 10 years
MonthEstimated value
2026
September 2026$5.15M
August 2026$5.1M
July 2026$5.81M
June 2026$5.48M
May 2026$5.51M
April 2026$5.53M
March 2026$5.59M
February 2026$5.72M
January 2026$4.15M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
39 Sengekontacket Rd, Oak Bluffs, MA
0.06
Single-Family Home
$3,746,925
11/14/25
4
3.5
2,861
30 Sengekontacket Rd, Oak Bluffs, MA
0.24
Single-Family Home
$2,125,000
10/30/25
4
3
2,262
10 Wood Duck Way, Oak Bluffs, MA
0.35
Single-Family Home
$2,250,000
12/10/25
4
3.5
3,014
103 Meadow View Rd, Oak Bluffs, MA
0.67
Single-Family Home
$1,687,500
07/10/26
3
2.5
2,862
29 Majors Cove Ln, Edgartown, MA
0.49
Single-Family Home
$4,500,000
06/11/26
5
4
3,518
16 Majors Cove Ln, Edgartown, MA
0.75
Single-Family Home
$1,350,000
11/20/25
3
2
1,965
32 Flamingo Dr, Edgartown, MA
0.96
Single-Family Home
$1,817,500
02/27/26
5
3
2,432
7 S Meadow Ln, Oak Bluffs, MA
0.89
Single-Family Home
$1,850,000
03/31/26
4
3
3,142
18 Puritan Dr, Oak Bluffs, MA
0.91
Single-Family Home
$1,885,000
07/29/26
5
3.5
2,527
16 Mockingbird Dr, Edgartown, MA
0.89
Single-Family Home
$2,495,000
11/20/25
4
5
2,694

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
39 Sengekontacket Rd, Oak Bluffs, MA 02557
0.06
$3,746,925
4
3.5
2,861
Recently Sold
30 Sengekontacket Rd, Oak Bluffs, MA 02557
0.24
$2,174,200
4
3
2,262
Off Market
18 Wood Duck Way, Edgartown, MA 02539
0.27
$1,800,000
4
3
2,864
For Sale
18 Wood Duck Way, Oak Bluffs, MA 02557
0.28
$1,800,000
4
3
2,064
For Sale
27 Brush Island Ln, Oak Bluffs, MA 02557
0.30
$3,694,000
4
4.5
4,000
Off Market
31 Ice Pond Ln, Oak Bluffs, MA 02557
0.31
-
-
-
-
Off Market
26 Box Turtle Ln, Oak Bluffs, MA 02557
0.30
$2,049,500
4
3.5
2,891
Off Market
10 Wood Duck Way, Oak Bluffs, MA 02557
0.35
$2,250,000
4
3.5
3,014
Recently Sold
14-R Pulpit Rock Rd, Oak Bluffs, MA 02557
0.40
$2,013,600
3
3
2,343
Off Market
36R Pulpit Rock Rd, Oak Bluffs, MA 02557
0.46
$3,909,500
3
3.5
2,385
Off Market
19 Stone Pound Way, Oak Bluffs, MA 02557
0.46
$2,498,500
3
2.5
2,742
Off Market

Price and Tax history

DateEventPrice
Aug 9, 2026
Source: CCIMLS #22603599
PriceChange
$5,495,000
Price decreased by 8%
Feb 11, 2026
Source: LINK #36712
Listed For Sale
$5,995,000
Dec 17, 2010
Source: LINK #20574
Sold
$3,250,000

LGBTQ Local Legal Protections

Peyton Wallace, Studio Realty LLC
Agent Phone: (508) 687-2699
All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than CC&I Assoc. of REALTORS®, Inc. includes the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS®, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. This site was last updated 2026-09-09 00:43:15 PDT. All properties are subject to prior sale, changes, or withdrawal. Copyright 2026© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

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Frequently asked questions about 43 Sengekontacket Road

  • What is the estimated monthly payment for 43 Sengekontacket Road?
    Based on a $5,495,000 list price with 20% down at today's rates, the estimated monthly payment for 43 Sengekontacket Road in Oak Bluffs, MA is approximately $31,508 (about $29,143 principal & interest, $2,290 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Oak Bluffs?
    Residents describe Oak Bluffs, MA as dog-friendly, well-kept, and walkable to restaurants. See homes for sale in Oak Bluffs, MA.
  • What are the closest schools to 43 Sengekontacket Road?
    The closest schools to 43 Sengekontacket Road in Oak Bluffs, MA are Martha's Vineyard Regional High School (rated 6/10), Oak Bluffs Elementary School (Pre-K/Middle, rated 7/10).
  • What is 43 Sengekontacket Road estimated to be worth?
    Trulia's estimated value for 43 Sengekontacket Road in Oak Bluffs, MA is $5,154,000.
  • Does 43 Sengekontacket Road have air conditioning?
    Yes, 43 Sengekontacket Road in Oak Bluffs, MA has air conditioning.
  • How big is the lot at 43 Sengekontacket Road?
    The lot at 43 Sengekontacket Road in Oak Bluffs, MA is about 2.9 acres.
43 Sengekontacket Road, Oak Bluffs, MA 02557 is a 3 bedroom, 3 bathroom, 2,234 sqft single-family home built in 1980. This property is currently available for sale and was listed by CCIMLS on Jul 25, 2026. The MLS # for this home is MLS# 22603599.