Is Oak Bluffs, MA dog-friendly?

As of early 2026, 96% of users say it's dog friendly

Do kids play outside in Oak Bluffs, MA?

As of early 2026, 86% of users say kids play outside

Are yards well-kept in Oak Bluffs, MA?

As of early 2026, 83% of users say yards are well-kept

Is Oak Bluffs, MA walkable to restaurants?

As of early 2026, 79% of users say it's walkable to restaurants

Is a car needed in Oak Bluffs, MA?

As of early 2026, 79% of users say car is needed

Would people walk alone at night in Oak Bluffs, MA?

As of early 2026, 78% of users say people would walk alone at night

Is Oak Bluffs, MA walkable to grocery stores?

As of early 2026, 78% of users say it's walkable to grocery stores

Is there wildlife in Oak Bluffs, MA?

As of early 2026, 73% of users say there's wildlife

Do residents of Oak Bluffs, MA plan to stay at least 5 years?

As of early 2026, 73% of users say they plan to stay for at least 5 years

Does Oak Bluffs, MA show holiday spirit?

As of early 2026, 70% of users say there's holiday spirit

Is Oak Bluffs, MA quiet?

As of early 2026, 67% of users say it's quiet

Is parking easy in Oak Bluffs, MA?

As of early 2026, 62% of users say parking is easy

Are neighbors friendly in Oak Bluffs, MA?

As of early 2026, 59% of users say neighbors are friendly

Are there community events in Oak Bluffs, MA?

As of early 2026, 47% of users say there are community events

Does Oak Bluffs, MA have sidewalks?

As of early 2026, 44% of users say there are sidewalks

Are the streets well-lit in Oak Bluffs, MA?

As of early 2026, 36% of users say streets are well-lit

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 .

What are the closest schools to Paddock Rd?

The closest schools to Paddock Rd in Oak Bluffs, MA are Martha's Vineyard Regional High School (rated 6/10), Oak Bluffs Elementary School (Pre-K/Middle, rated 7/10).

How big is the lot at Paddock Rd?

The lot at Paddock Rd in Oak Bluffs, MA is about 25.6 acres .

OFF MARKET

Paddock Rd
Oak Bluffs, MA 02557

Studio

Studio

(on 25.63 acres)

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
7 S Meadow Ln, Oak Bluffs, MA	0.25	Single-Family Home	$1,850,000	03/31/26	4	3	3,142
63 Bayes Hill Rd, Oak Bluffs, MA	0.43	Single-Family Home	$2,900,000	03/30/26	4	4	5,169
103 Meadow View Rd, Oak Bluffs, MA	0.42	Single-Family Home	$1,687,500	07/10/26	3	2.5	2,862
5 Bayes Hill Circle, Oak Bluffs, MA	0.48	Single-Family Home	$1,600,000	01/20/26	4	2.5	2,855
7 Upper Meadow Ln, Oak Bluffs, MA	0.50	Single-Family Home	$1,625,000	05/12/26	4	2.5	3,268
44 Tiffany Dr, Oak Bluffs, MA	0.56	Single-Family Home	$1,600,000	01/06/26	4	4.5	4,023
18 Puritan Dr, Oak Bluffs, MA	0.60	Single-Family Home	$1,885,000	07/29/26	5	3.5	2,527
10 Wood Duck Way, Oak Bluffs, MA	0.67	Single-Family Home	$2,250,000	12/10/25	4	3.5	3,014
26 Box Turtle Ln, Oak Bluffs, MA	0.74	Single-Family Home	$1,995,000	08/29/25	4	3.5	2,891
30 Sengekontacket Rd, Oak Bluffs, MA	0.77	Single-Family Home	$2,125,000	10/30/25	4	3	2,262

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
44 Paddock Rd #20, Oak Bluffs, MA 02557	0.08	-	-	-	-	Off Market
8 Paddock Rd, Oak Bluffs, MA 02557	0.15	$5,450,000	4	5.5	3,300	For Sale
5 Paddock Road, Oak Bluffs, MA 02557	0.20	-	-	-	-	Off Market
4 High Meadow Ln, Oak Bluffs, MA 02557	0.23	$2,260,000	4	3.5	2,810	For Sale
7 S Meadow Ln, Oak Bluffs, MA 02557	0.25	$1,850,000	4	3	3,142	Recently Sold
22 Paddock Rd, Oak Bluffs, MA 02557	0.23	$1,895,000	6	6.5	4,500	For Sale
25 Paddock Rd #23, Oak Bluffs, MA 02557	0.23	-	-	-	-	Off Market
14 High Meadow Ln, Oak Bluffs, MA 02557	0.27	$1,750,000	3	3	1,932	For Sale
34 Paddock Rd, Oak Bluffs, MA 02557	0.24	-	-	-	-	Off Market
Paddock Rd, Oak Bluffs, MA 02557	0.27	-	-	-	-	Off Market
11 High Meadow Ln, Oak Bluffs, MA 02557	0.31	$1,660,800	4	2.5	1,811	Off Market
40 Paddock Rd #18, Oak Bluffs, MA 02557	0.32	-	-	-	-	Off Market

Local Information

Map ViewExplore the area around Paddock Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Lot Size

25.63 acres

About this House

This single-family home is located at Paddock Rd, Oak Bluffs, MA. Paddock Rd is in Oak Bluffs, MA and in ZIP code 02557. This property has a lot size of 25.63 acres.

Paddock Rd, Oak Bluffs, MA 02557 is a studio single-family home. It is currently off market. The Trulia Estimate rent is $7,819/month.

Home Details for Paddock Rd

Property Information
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 25.63 acres

Price and Tax history

Year	Property tax	Tax assessment
2025	$950	$188,200

Home facts updated by county records

Additional Cost

Market trends in Oak Bluffs

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

4MoM

Around this home

Oak Bluffs Elementary School
PK-8
Public
390 Students
Oak Bluffs School District
7/10
GreatSchools Rating
Parent Rating Average
An 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 Review
10mo ago
4 Reviews

View nearby schools on GreatSchools

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

Sourced by Trulia users. Learn more about our methodology.

Trulia User
Resident
1w ago
"Easy to walk dogs"
0
Flag
P5j4f84ncw
Resident
6mo ago
"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
Visitor
1y ago
"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
Resident
1y ago
"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
Visitor
1y ago
"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
Resident
7y ago
"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.
Prev. Resident
8y ago
"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
11y ago
"I own a property in Oak Bluffs"
0
Flag
Kristin Z.
11y ago
"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.
11y ago
"This is a lovely and desirable area close to town and everything the island has to offer."
1
Flag

LGBTQ Local Legal Protections

Frequently asked questions about Paddock Rd

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.
What are the closest schools to Paddock Rd?
The closest schools to Paddock Rd in Oak Bluffs, MA are Martha's Vineyard Regional High School (rated 6/10), Oak Bluffs Elementary School (Pre-K/Middle, rated 7/10).
How big is the lot at Paddock Rd?
The lot at Paddock Rd in Oak Bluffs, MA is about 25.6 acres.

Explore by feature - Washer/dryer

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2,281 sqft
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PET FRIENDLY
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4 bd
2 ba
1,520 sqft
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APPLY INSTANTLY
PET FRIENDLY
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$2,250/mo
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2 bd
1 ba
600 sqft
7 Wapello St,
Oak Bluffs, MA 02557
$28,500/mo
Fees may apply
9 bd
6.5 ba
3,500 sqft
9 Tuckernuck Ave,
Oak Bluffs, MA 02557

Apartments for Rent

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Contact for price
1-2 bd
1-2 ba
145 Main St #776f18ccb,
Vineyard Haven, MA 02568
Contact for price
1-2 bd
1-2 ba
490 Edgartown Vineyard Haven Rd #776f18ccb,
Edgartown, MA 02539
FURNISHED
$7,323/mo
Total price
3 bd
2 ba
25 Simpson Ave #ID1514679P,
Vineyard Haven, MA 02568
FURNISHED
$7,390/mo
Total price
4 bd
3 ba
13 N Meadow Ln #ID1514673P,
Vineyard Haven, MA 02568
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Oak Bluffs
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Off Market Homes Near Paddock Rd

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SOLD
AUG 19, 2026
$2,195,000
4 bd
2.5 ba
2,890 sqft
30 Daggett Ave,
Tisbury, MA 02568
Dawn Bellante, Sandpiper Realty, Inc.
SOLD
AUG 19, 2026
$3,600,000
5 bd
6.5 ba
4,372 sqft
139 Main St,
Tisbury, MA 02568
Portfolio Properties
SOLD
AUG 18, 2026
$435,000
11 Boylston Dr,
Edgartown, MA 02539
Wallace & Co. Sotheby's
SOLD
AUG 14, 2026
$1,200,000
66 Munroe Ave #17,
Oak Bluffs, MA 02557
Ocean Park Realty Inc
SOLD
AUG 13, 2026
$1,035,000
3 bd
2 ba
1,135 sqft
21 Butler Ave,
Oak Bluffs, MA 02557
Compass LLC
SOLD
AUG 13, 2026
$1,035,000
3 bd
2 ba
1,135 sqft
21 Butler Ave #1,
Oak Bluffs, MA 02557
Jen O'Hanlon, Compass
SOLD
AUG 11, 2026
$1,695,000
3 bd
3 ba
2,296 sqft
177 W Tisbury Rd,
Edgartown, MA 02539
Sandpiper Realty
SOLD
AUG 11, 2026
$2,100,000
4 bd
4 ba
2,516 sqft
25 Pennacook Ave,
Oak Bluffs, MA 02557
Martha's Vineyard Island-Wide Realty
SOLD
AUG 11, 2026
$6,400,000
7 bd
5.5 ba
4,730 sqft
180 Pilot Hill Farm Rd,
Tisbury, MA 02568
Tea Lane Associates
SOLD
AUG 7, 2026
$530,000
2 bd
1 ba
704 sqft
124 Skiff Ave #C-12,
Tisbury, MA 02568
Island Real Estate
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Oak Bluffs
Take a look

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Homes for sale near Paddock Rd

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1.95 ACRES
$5,450,000
4 bd
5.5 ba
3,300 sqft
8 Paddock Rd,
Oak Bluffs, MA 02557
Sandpiper Realty
0.89 ACRES
$2,260,000
4 bd
3.5 ba
2,810 sqft
4 High Meadow Ln,
Oak Bluffs, MA 02557
Portfolio Properties
0.8 ACRES
$1,750,000
3 bd
3 ba
1,932 sqft
14 High Meadow Ln,
Oak Bluffs, MA 02557
Compass | Point B
1.57 ACRES
$4,695,000
7 bd
4.5 ba
5,320 sqft
8 Fresh Pond Rd,
Oak Bluffs, MA 02557
Keller Williams Realty
1.38 ACRES
$2,800,000
4 bd
4.5 ba
4,023 sqft
44 Tiffany Dr,
Oak Bluffs, MA 02557
MV Luxury Homes
0.26 ACRES
$2,250,000
3 bd
3.5 ba
2,475 sqft
35 Double Ox Rd,
Oak Bluffs, MA 02557
Ocean Park Realty Inc
0.47 ACRES
$1,850,000
4 bd
2 ba
1,833 sqft
22 Old Harbor Ln,
Oak Bluffs, MA 02557
Sandpiper Realty
1.34 ACRES
$3,400,000
3 bd
4.5 ba
3,260 sqft
27 Double Ox Rd,
Oak Bluffs, MA 02557
Sandpiper Realty
0.81 ACRES
$1,800,000
4 bd
3 ba
2,064 sqft
18 Wood Duck Way,
Oak Bluffs, MA 02557
Portfolio Properties
0.81 ACRES
$1,800,000
4 bd
3 ba
2,864 sqft
18 Wood Duck Way,
Edgartown, MA 02539
Portfolio Properties
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Oak Bluffs
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Paddock Rd
Oak Bluffs, MA 02557