20 E  Side Rd, Oak Bluffs, MA 02557
OFF MARKET

20 E Side Rd
Oak Bluffs, MA 02557

  • 3 Beds
  • 2 Baths
  • 2,302 sqft (on 0.39 acres)

$3,289,400

Trulia Estimate
as of May 13, 2026
Est. Refi. Payment $17,649/mo*

$3,289,400

Trulia Estimate
as of May 13, 2026
Est. Refi. Payment $17,649/mo*
3 Beds
2 Baths
2,302 sqft
(on 0.39 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

The property boasts of an expansive Lagoon Waterfront and stunning sunsets that take your breath away. There are a few steps to small beach area for sunbathing, swimming or kayaking. There is also a transfer of a mooring that is included in the sale. Buyer pays annual fee. Open floor plan includes modern kitchen with two ovens, granite counters and custom glass-front cabinets. A center-piece stone wood-burning fireplace graces the living room, kitchen and dining area. French doors lead out to the deck area for relaxing, dining, or just taking in the view. The first floor has two bedrooms and a full bath. Kitchen area also has a pantry and wide hallway leading to upstairs. The second floor primary bedroom has sweeping views of the Lagoon and shares a full bath with another room that can be a bedroom or study. Tons of closet space along the hallway.There are lovely architectural details throughout the home designed by Bruce MacNelly. This desirable location is only a little over a mile to either Vineyard Haven or Oak Bluffs. Bus line and bike paths are at the end of the road for easy access to all Island locations. Mini- splits are located throughout the home. The laundry area is located in a large basement which also houses a work area and a walk-in owners cedar closet.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from June 01, 2023

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
156 days ago

Home Details for 20 E Side Rd

Interior Features

Interior Details
Basement: Laundry area, cedar closet and work benchNumber of Rooms: 6
Beds & Baths
Number of Bedrooms: 3Main Level Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 2302 Square Feet
Appliances & Utilities
Utilities: CblAppliances: Stove: yes - electric, Washer: yes
Heating & Cooling
Heating: OFHWNo CoolingHas HeatingHeating Fuel: OFHW
Fireplace & Spa
Fireplace: 1
Windows, Doors, Floors & Walls
Flooring: 3
Levels, Entrance, & Accessibility
Floors: 3
View
Has a ViewView: Harbor

Exterior Features

Exterior Home Features
Other Structures: ShedExterior: WViews, Deck, PvtBch, DdBchFoundation: cement
Parking & Garage
No CarportNo GarageNo Attached GarageParking: 3
Frontage
WaterfrontWaterfront: WaterfrontFrontage Type: WaterfrontOn Waterfront
Water & Sewer
Sewer: Septic Tank

Property Information

Year Built
Year Built: 2002Year Renovated: 2016
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Property Information
Parcel Number: 1

Price & Status

Price
List Price: $2,775,000

Active Status

MLS Status: S

Location

Direction & Address
City: Oak Bluffs

Building

Building Area
Building Area: 2302 Square Feet

Lot Information

Lot Area: 0.39 acres

Offer

Listing Agreement Type: E

Miscellaneous

BasementMls Number: 40630Water ViewWater View: Harbor
Last check for updates: about 3 hours ago
Listed by Joanna Fairchild 617-413-8681
eXp Realty
Bought with: Jill Hobby Napior 508-642-0831, Tea Lane Associates
Source: LINK, MLS#40630

Price History for 20 E Side Rd

DatePriceEventSource
05/16/2023$2,780,000Sold
LINK #40630
04/05/2023$2,775,000PendingLINK #40630
03/28/2023$2,775,000Listed For SaleLINK #40630
12/17/2022$2,900,000ListingRemovedLINK #40165
10/24/2022$2,900,000PendingToActiveLINK #40165
10/18/2022$2,900,000PendingLINK #40165
10/03/2022$2,900,000Listed For SaleLINK #40165
09/18/1992$215,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$14,864
Assessment$2,943,300
Home facts updated by county records

Comparable Sales for 20 E Side Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.03
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
0.03
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
0.09
Single-Family Home
$1,310,000
08/18/25
3
2
1,964
0.09
Single-Family Home
$1,600,000
05/22/25
3
2
1,594
0.09
Single-Family Home
$1,350,000
08/15/25
3
2
1,864
0.25
Single-Family Home
$1,850,000
08/04/25
3
3
2,210
0.32
Single-Family Home
$1,270,000
05/23/25
3
2
2,192
0.31
Single-Family Home
$880,000
10/17/25
3
2
1,365
0.49
Single-Family Home
$1,450,000
05/04/26
3
1.5
2,448
0.26
Single-Family Home
$1,090,000
01/16/26
3
2
1,428

Assigned Schools

These are the assigned schools for 20 E Side Rd.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

Learn more about our methodology.
  • P5j4f84ncw
    "Local people, well known community,quite,hard working people,solid business,good schools,hospitality,new opportunities,security and safety place to leave. "
  • 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 "
  • Trulia User
    "Oak Bluffs is a charming town with a bustling summer harbor and lovely shopping district. It’s a beautiful place to live. "
  • Jrheneeb
    "I love it here. It’s beautiful and the people are amazing. It’s a great place To come relax and unwind. "
  • Kayceesmith27
    "I take the bus to and from work . Car for longer distances. Boat to get to the main land which is 45min ride."
  • 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."
  • tkurian
    "I own a property in Oak Bluffs"
  • 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. "
  • Island R. E.
    "This is a lovely and desirable area close to town and everything the island has to offer."

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Apartments for Rent

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Homes for sale near 20 E Side Rd

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© 2026 LINK, All Rights Reserved. Data last updated: 2026-05-12 15:46:40 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.

Homes for rent near 20 E Side Rd

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Off Market Homes Near 20 E Side Rd

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20 E Side Rd, Oak Bluffs, MA 02557 is a 3 bedroom, 2 bathroom, 2,302 sqft single-family home built in 2002. This property is not currently available for sale. 20 E Side Rd was last sold on May 16, 2023 for $2,780,000 (0% higher than the asking price of $2,775,000). The current Trulia Estimate for 20 E Side Rd is $3,289,400.