20 E Side Rd
Oak Bluffs, MA 02557
3 Beds
2 Baths
2,302 sqft (on 0.39 acres)
3 Beds
2 Baths
2,302 sqft
(on 0.39 acres)
Local Information
- Map ViewExplore the area around 20 E Side Rd.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
2002
Lot Size
0.39 acres
Living Area
2,302 sqft
Price/Sqft
$1,425
About this House
This single-family home is located at 20 E Side Rd, Oak Bluffs, MA. 20 E Side Rd is in Oak Bluffs, MA and in ZIP code 02557. This property has 3 bedrooms, 2 bathrooms and approximately 2,302 sqft of floor space. This property has a lot size of 0.39 acres and was built in 2002.
20 E Side Rd, Oak Bluffs, MA 02557 is a 3 bedroom, 2 bathroom, 2,302 sqft single-family home built in 2002. It last sold for $2,780,000 on May 16, 2023. It is currently off market. The Trulia Estimate is $3,280,600, with a rent estimate of $5,756/month.
Home Details for 20 E Side Rd
|
|---|
Heating & Cooling Heating: Other, OilAir ConditioningHeating Fuel: Other |
Levels, Entrance, & Accessibility Stories: 2 |
Interior Details Number of Rooms: 6 |
|
|---|
Exterior Home Features Roof: AsphaltExterior: Wood |
|
|---|
Year Built Year Built: 2002Year Updated: 2008 |
Property Type / Style Property Type: Single Family HomeArchitecture: ranch |
|
|---|
Units in Building: 1 |
|
|---|
Lot Area: 0.39 acres |
Price History for 20 E Side Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 05/16/2023 | $2,780,000 | Sold | LINK #40630 |
| 04/05/2023 | $2,775,000 | Pending | LINK #40630 |
| 03/28/2023 | $2,775,000 | Listed For Sale | LINK #40630 |
| 12/17/2022 | $2,900,000 | ListingRemoved | LINK #40165 |
| 10/24/2022 | $2,900,000 | PendingToActive | LINK #40165 |
| 10/18/2022 | $2,900,000 | Pending | LINK #40165 |
| 10/03/2022 | $2,900,000 | Listed For Sale | LINK #40165 |
| 09/18/1992 | $215,000 | Sold | N/A |
Market trends in Oak Bluffs
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
54
- Results are loading
Property Tax and Assessment
| Year | 2025 |
|---|---|
| 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 |
|---|---|---|---|---|---|---|---|
0.04 | Single-Family Home | $1,530,000 | 01/13/26 | 3 | 2 | 2,015 | |
0.04 | 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 | |
0.10 | Single-Family Home | $1,350,000 | 08/15/25 | 3 | 2 | 1,864 | |
0.32 | Single-Family Home | $880,000 | 10/17/25 | 3 | 2 | 1,365 | |
0.50 | Single-Family Home | $1,450,000 | 05/04/26 | 3 | 1.5 | 2,448 | |
0.27 | Single-Family Home | $1,090,000 | 01/16/26 | 3 | 2 | 1,428 | |
0.09 | Single-Family Home | $705,000 | 04/16/26 | 4 | 2 | 2,123 | |
0.87 | Single-Family Home | $1,875,000 | 05/13/26 | 3 | 2 | 2,215 | |
0.43 | Single-Family Home | $1,470,000 | 10/27/25 | 3 | 2.5 | 1,620 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
SOLDJAN 13, 2026Susie Pimpton-Wallo, Compass
SOLDJAN 13, 2026Compass | The O'Hanlon Group
OFF MARKETSandpiper Realty
OFF MARKETOcean Park Realty Inc
OFF MARKETWallace & Co. Sotheby's
OFF MARKETOcean Park Realty Inc
Assigned Schools
These are the assigned schools for 20 E Side Rd.
- Oak Bluffs Elementary School
- PK-8
- Public
- 390 Students
7/10GreatSchools RatingParent Rating AverageAn excellent school where students seem to be happy, learning and engaged. You can tell the teachers really care about and truly want the best for their students. The new principal is very energetic, involved and approachable and he seems very well-liked by students, parents and the staff (which is everything).Parent Review9mo ago - Martha's Vineyard Regional High School
- 9-12
- Public
- 703 Students
6/10GreatSchools RatingParent Rating AverageStandards for academic engagement are ON THE FLOOR at this school. The “c1” courses are equivalent to a special ed class in any other school, and an honors class to a typical c1 course. Very, very low expectations for C1 students, often no homework at all, or just one assignment per week, and very little in class work. Many teachers in the school are just blatantly bad at their jobs. The school is not able to address it due to a lack of new teachers, but also because they refuse to train teachers properly. I will admit, many teachers are incredible, but it is unacceptable that the academic standards are so incredibly low and how the administration allows teachers to get by without being able to teach the curriculum during the school year. Specifically, this school and the school system on the island in general is notorious for its awful math program. The school is now having to extend the math period for freshmen because of the amount of failing students (likely more changes to come). The administration has also consistently shown disregard for the opinions of students and families, particularly about the new phone policy. Many valid arguments were simply dismissed or never addressed or answered prior to the establishment of the policy. The administration is also very unaware of what is actually happening (particularly the former principal) in the student body, as a very, very small percentage of students are actually following the policy—the vast majority sticking to the old rule of just not having phones out in class, while the administration continually brags about how well the implementation of the policy has gone. Hopefully as the former principal is now gone some of these issues will be addressed, but it is important to note that there are many issues with this school.Student Review11mo ago 
Check out schools near 20 E Side Rd.
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.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Apartments for Rent
FURNISHED
FURNISHED
See more homes for rent inOak Bluffs
Homes for sale near 20 E Side Rd
0.3 ACRESWallace & Co. Sotheby's International Realty
1.06 ACRESAlisan Lohan-Conway Properties
Wallace & Co. Sotheby's International Realty
See more homes for sale inOak Bluffs
Off Market Homes Near 20 E Side Rd
SOLDJUL 10, 2026Karen M. Overtoom R.E.
SOLDJUN 29, 2026Island Real Estate
SOLDJUN 10, 2026Wallace & Co. Sotheby's- See more homes for sale inOak Bluffs
Frequently asked questions about 20 E Side Rd
- What is 20 E Side Rd estimated to be worth?Trulia's estimated value for 20 E Side Rd in Oak Bluffs, MA is $3,280,600.
- What is the price history for 20 E Side Rd?20 E Side Rd in Oak Bluffs, MA last sold for $2,780,000 in May 2023.
- Is Oak Bluffs a buyer's or seller's market?Oak Bluffs is currently a buyer'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 20 E Side Rd?The lot at 20 E Side Rd in Oak Bluffs, MA is about 0.39 acres (16,995 sq ft).