39 Sengekontacket Rd, Oak Bluffs, MA 02557
Property image
Property image
SOLD
NOV 14, 2025

$3,830,600

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 2,861 sqft (on 1.30 acres)

39 Sengekontacket Rd, Oak Bluffs, MA 02557

Est. Refi. Payment $21,731/mo*
Refinance Your Home
Currently Off Market - Sold Nov 14, 2025 for $3,746,925 (8% below list price)

Home Value

Trulia Estimate
$3.83M
Since last month
Increased$27K (+0.7%)
Since last year
Increased$141K (+3.8%)
Since last sale
Increased$95K (+2.5%)
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 +138% in the last 10 years
MonthEstimated value
2026
August 2026$3.84M
August 2026$3.83M
July 2026$3.81M
June 2026$3.8M
May 2026$3.82M
April 2026$3.78M
March 2026$3.81M
February 2026$3.8M
January 2026$3.76M
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
30 Sengekontacket Rd, Oak Bluffs, MA
0.19
Single-Family Home
$2,125,000
10/30/25
4
3
2,262
10 Wood Duck Way, Oak Bluffs, MA
0.30
Single-Family Home
$2,250,000
12/10/25
4
3.5
3,014
29 Majors Cove Ln, Edgartown, MA
0.45
Single-Family Home
$4,500,000
06/11/26
5
4
3,518
103 Meadow View Rd, Oak Bluffs, MA
0.66
Single-Family Home
$1,687,500
07/10/26
3
2.5
2,862
7 S Meadow Ln, Oak Bluffs, MA
0.87
Single-Family Home
$1,850,000
03/31/26
4
3
3,142
32 Flamingo Dr, Edgartown, MA
0.91
Single-Family Home
$1,817,500
02/27/26
5
3
2,432
16 Mockingbird Dr, Edgartown, MA
0.83
Single-Family Home
$2,495,000
11/20/25
4
5
2,694
18 Puritan Dr, Oak Bluffs, MA
0.91
Single-Family Home
$1,885,000
07/29/26
5
3.5
2,527
2 Farm Path, Oak Bluffs, MA
1.09
Single-Family Home
$1,705,000
03/24/26
4
3
3,058

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
43 Sengekontacket Road, Oak Bluffs, MA 02557
0.06
$5,495,000
3
3
2,234
For Sale
30 Sengekontacket Rd, Oak Bluffs, MA 02557
0.19
$2,174,200
4
3
2,262
Off Market
18 Wood Duck Way, Edgartown, MA 02539
0.23
$1,800,000
4
3
2,864
For Sale
18 Wood Duck Way, Oak Bluffs, MA 02557
0.23
$1,800,000
4
3
2,064
For Sale
26 Box Turtle Ln, Oak Bluffs, MA 02557
0.25
$2,049,500
4
3.5
2,891
Off Market
31 Ice Pond Ln, Oak Bluffs, MA 02557
0.28
-
-
-
-
Off Market
10 Wood Duck Way, Oak Bluffs, MA 02557
0.30
$2,250,000
4
3.5
3,014
Recently Sold
27 Brush Island Ln, Oak Bluffs, MA 02557
0.33
$3,694,000
4
4.5
4,000
Off Market
19 Stone Pound Way, Oak Bluffs, MA 02557
0.40
$2,498,500
3
2.5
2,742
Off Market
10 SE Bachelder Avenue, Edgartown, MA 02539
0.43
$3,684,300
3
2.5
1,353
Off Market
29 Majors Cove Ln, Edgartown, MA 02539
0.45
$4,500,000
5
4
3,518
Recently Sold

Local Information

  • Map ViewExplore the area around 39 Sengekontacket Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1974
1.3 acre lot
2,861 sqft
$1,310/sqft
HOA $92/mo

About this House

SPECTACULAR WATERFRONT home with stunning water views from every room. Situated in a private location in the Sengekontacket Association, this is an exceptional property in a rare setting. Completely renovated in 2014. In addition to the breathtaking water view of Major's Cove and of Felix Neck throughout the home, the front of the property faces serene pastoral views. This home offers four bedrooms with a main floor master and ensuite, exquisite craftmanship throughout and a unique setting on the water. Great care was taken in the planning of this home to ensure maximum enjoyment of the tranquil surroundings and views. Each of three bedrooms on the second floor has a water view. The quality of materials used in the construction of this home is outstanding. As you walk through the property, the landscaping and gardens are impeccable, and have been featured in MV Magazine. The back yard gently slopes down to the water. Carefully planned by the owners, this home was constructed to follow net zero design principles which provide an energy-efficient retreat. Lovingly maintained by the owners, this property is a true one of a kind sanctuary on the Vineyard.
39 Sengekontacket Rd, Oak Bluffs, MA 02557 is a 4 bedroom, 4 bathroom, 2,861 sqft single-family home built in 1974. It last sold for $3,746,925 on Nov 14, 2025 (8% below the $4,075,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,830,600.
Last check for updates: about 14 hours ago
Listed by Jayne Isford
Ocean Park Realty Inc
Bought with: Katya Brush, Compass | Point B
Source: LINK, MLS#43191

Home Details for 39 Sengekontacket Rd

Interior Features

Interior Details
Basement: Partially finished basement with playroom, large workshop and separate utility room.Basement is fully insulated.Clamdoor bulkhead.Number of Rooms: 8
Beds & Baths
Number of Bedrooms: 4Main Level Bedrooms: 1Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2861 Square Feet
Appliances & Utilities
Utilities: CblAppliances: Stove: Jenn-Air Steam Convection oven and Jenn-Air Convection oven, Washer: Electrolux
Heating & Cooling
Heating: ElectricNo CoolingHas HeatingHeating Fuel: Electric
Windows, Doors, Floors & Walls
Flooring: 2
Levels, Entrance, & Accessibility
Floors: 2
View
Has a ViewView: Pasture

Exterior Features

Exterior Home Features
Other Structures: There is a very pretty outdoor storage shed with a good amount of storage space. The property is entitled to install a boat mooring subject to prior review and approval by the Oak Bluffs Harbormaster.Exterior: C/Tennis, Cov, Deck, Garden, ScrPorch, WViewsFoundation: Poured concrete.Garden
Parking & Garage
No CarportNo GarageNo Attached GarageParking: Parking for several cars.
Frontage
WaterfrontWaterfront: WaterfrontFrontage Type: WaterfrontOn Waterfront
Water & Sewer
Sewer: Septic Tank

Property Information

Year Built
Year Built: 1974Year Renovated: 2014
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Property Information
Parcel Number: 48650

Price & Status

Price
List Price: $4,075,000Price Per Sqft: $1,310/sqft

Active Status

MLS Status: S

Location

Direction & Address
City: Oak Bluffs

Building

Building Area
Building Area: 2861 Square Feet

HOA

HOA Fee Includes: Community tennis courts, boat dock, club house, garbage pick up, road maintenance and snow removal. Association Board reviews fees annually.Has an HOAHOA Fee: $1,100/Annually

Lot Information

Lot Area: 1.3 Acres

Offer

Listing Agreement Type: E

Miscellaneous

BasementMls Number: 43191

Price and Tax history

DateEventPrice
Nov 14, 2025
Source: LINK #43191
Sold
$3,746,925
Oct 6, 2025
Source: LINK #43191
Pending
$4,075,000
Sep 6, 2025
Source: LINK #43191
Contingent
$4,075,000
May 15, 2025
Source: LINK #43191
Listed For Sale
$4,075,000
Nov 19, 2012
Source: LINK #22721
Sold
$1,200,000

Market trends in Oak Bluffs

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
72
14MoM

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

LGBTQ Local Legal Protections

© 2026 LINK, All Rights Reserved. Data last updated: 2026-09-12 00:13:25 PDT. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update.

Frequently asked questions about 39 Sengekontacket Rd

  • What is 39 Sengekontacket Rd estimated to be worth?
    Trulia's estimated value for 39 Sengekontacket Rd in Oak Bluffs, MA is $3,830,600.
  • What is the price history for 39 Sengekontacket Rd?
    39 Sengekontacket Rd in Oak Bluffs, MA last sold for $3,746,925 in November 2025.
  • Is Oak Bluffs a buyer's or seller's market?
    Oak Bluffs is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Oak Bluffs?
    Residents describe Oak Bluffs, MA as dog-friendly, well-kept, and walkable to restaurants. See recently sold homes in Oak Bluffs, MA.
  • How big is the lot at 39 Sengekontacket Rd?
    The lot at 39 Sengekontacket Rd in Oak Bluffs, MA is about 1.3 acres.
  • Does 39 Sengekontacket Rd have parking?
    Yes, 39 Sengekontacket Rd in Oak Bluffs, MA has on-site parking.

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