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

What is the price history for 20 Paddock Rd?

20 Paddock Rd in Oak Bluffs, MA last sold for $3,100,000 in October 2021.

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 .

What are the closest schools to 20 Paddock Rd?

The closest schools to 20 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).

OFF MARKET

$3,100,000

Last sold price

5 Beds
4,920 sqft (on 2.01 acres)

20 Paddock Rd, Oak Bluffs, MA 02557

Currently Off Market - Sold Oct 18, 2021 for $3,100,000

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
2 Hope'S Way, Oak Bluffs, MA	0.36	Lot/Land	$665,000	03/06/26	3	3.5	1,716
34 Paddock Rd, Oak Bluffs, MA	0.19	Lot/Land	$1,800,000	10/02/25		-	-
200 Edgartown Vineyard Hvn, Oak Bluffs, MA	1.02	Lot/Land	$1,100,000	12/29/25		-	-
Red Buoy Ln #147, Vineyard Haven, MA	1.20	Lot/Land	$585,000	02/05/26		-	-
Lyle Ln, Vineyard Haven, MA	1.66	Lot/Land	$525,000	05/29/26		-	-
Worcester Avenue & Olinda, Oak Bluffs, MA	1.59	Lot/Land	$500,000	11/17/25		-	-
56 Holmes Hole Rd, Oak Bluffs, MA	1.75	Lot/Land	$450,000	06/15/26		-	-
61 3rd St N, Edgartown, MA	2.19	Lot/Land	$699,000	08/31/26		-	-
11 Boylston Dr, Edgartown, MA	2.35	Lot/Land	$435,000	08/18/26		-	-
77 Sixth Street N Street, Vineyard Haven, MA	2.30	Lot/Land	$612,500	07/29/26		-	-

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
22 Paddock Rd, Oak Bluffs, MA 02557	0.08	$1,895,000	6	6.5	4,500	For Sale
25 Paddock Rd #23, Oak Bluffs, MA 02557	0.08	-	-	-	-	Off Market
40 Paddock Rd #18, Oak Bluffs, MA 02557	0.13	-	-	-	-	Off Market
34 Paddock Rd, Oak Bluffs, MA 02557	0.19	-	-	-	-	Off Market
14 High Meadow Ln, Oak Bluffs, MA 02557	0.17	$1,750,000	3	3	1,932	For Sale
63 Bayes Hill Rd, Oak Bluffs, MA 02557	0.18	$2,900,000	4	4	5,169	Recently Sold
5 Bayes Hill Circle, Oak Bluffs, MA 02557	0.19	$1,600,000	4	2.5	2,855	Recently Sold
19 Tiffany Dr, Oak Bluffs, MA 02557	0.22	$2,143,100	4	2.5	2,585	Off Market
11 High Meadow Ln, Oak Bluffs, MA 02557	0.22	$1,674,400	4	2.5	1,811	Off Market
4 High Meadow Ln, Oak Bluffs, MA 02557	0.25	$2,260,000	4	3.5	2,810	For Sale
35 Double Ox Rd, Oak Bluffs, MA 02557	0.27	$685,000	-	-	-	For Sale
13 W Meadow Lane, Oak Bluffs, MA 02557	0.28	$1,610,400	4	3.5	2,623	Off Market

Local Information

Map ViewExplore the area around 20 Paddock Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Lot/Land

Built in 2021

2.01 acre lot

4,920 sqft

About this House

=THE PRESERVE AT THE WOODLANDS. Nestled in a private and beautiful multi-acre woodland setting, The Preserve At The Woodlands is Martha's Vineyard's newest luxury home enclave with beautiful pond, woodlands and golden meadow views. This gorgeous property is surrounded by conservation land that connects with miles of walking/hiking trails -- and the property also offers convenient access to the bicycle path, Farm Neck Golf Club and all three down-Island towns and beaches. The Preserve At The Woodlands consists of 26 home sites, ranging in size between 1.8 and 4.0 acres, each designed to provide for privacy and views amidst the natural landscape. There are underground utilities and Town Water in place and each lot has been approved for up to six (6) bedrooms per the Oak Bluffs Board Of Health. Carefully crafted association covenants have been developed to preserve the character, integrity and value of this distinctive property. Note: See the attached sales brochure with map showing all available lots and pricing.

20 Paddock Rd, Oak Bluffs, MA 02557 is a 5 bedroom, 4,920 sqft lot/land built in 2021. It last sold for $3,100,000 on Oct 18, 2021. This property is not currently displayed as for sale or rent on Trulia.

Home Details for 20 Paddock Rd

Interior Features
Heating & Cooling Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility Stories: 2

Exterior Features
Exterior Home Features Roof: AsphaltExterior: Wood

Property Information
Year Built Year Built: 2021
Property Type / Style Property Type: Lot LandArchitecture: Cape Cod

Community
Units in Building: 1

Lot Information
Lot Area: 2.01 acres

Price and Tax history

Date	Event	Price
Oct 18, 2021 Source: LINK #38915	Sold	$3,100,000
Aug 31, 2020 Source: N/A	Sold	$535,000
Apr 20, 2020 Source: Agent Provided	ListingRemoved	$550,000
Mar 18, 2020 Source: Agent Provided	Listed For Sale	$550,000

Year	Property tax	Tax assessment
2025	$22,531	$4,461,500

Additional Cost

Market trends in Oak Bluffs

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

14MoM

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
11mo 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
1mo ago
"Easy to walk dogs"
0
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P5j4f84ncw
Resident
7mo ago
"Local people, well known community,quite,hard working people,solid business,good schools,hospitality,new opportunities,security and safety place to leave. "
0
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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
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Trulia User
Resident
2y ago
"Oak Bluffs is a charming town with a bustling summer harbor and lovely shopping district. It’s a beautiful place to live. "
0
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Jrheneeb
Visitor
2y ago
"I love it here. It’s beautiful and the people are amazing. It’s a great place To come relax and unwind. "
0
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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
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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
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tkurian
11y ago
"I own a property in Oak Bluffs"
0
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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 20 Paddock Rd

What is the price history for 20 Paddock Rd?
20 Paddock Rd in Oak Bluffs, MA last sold for $3,100,000 in October 2021.
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.
What are the closest schools to 20 Paddock Rd?
The closest schools to 20 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).

Explore by feature - Air Conditioning

APPLY INSTANTLY
FURNISHED
$4,950/mo
Total price
3 bd
1 ba
1,056 sqft
28 2nd Ave,
Oak Bluffs, MA 02557
APPLY INSTANTLY
FURNISHED
$3,500/mo
Total price
2 bd
2 ba
1,000 sqft
Address Not Disclosed,
Oak Bluffs, MA 02557
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$6,550/mo
Total price
4 bd
2 ba
1,520 sqft
107 Barnes Rd,
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
$15,000/mo
Fees may apply
5 bd
3 ba
3,000 sqft
55 Samoset Ave,
Oak Bluffs, MA 02557

Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Oak Bluffs, MA

FURNISHED
$7,323/mo
Total price
3 bd
2 ba
1,022 sqft
25 Simpson Ave #ID1514679P,
Vineyard Haven, MA 02568
FURNISHED
$7,390/mo
Total price
4 bd
3 ba
2,281 sqft
13 N Meadow Ln #ID1514673P,
Vineyard Haven, MA 02568
APPLY INSTANTLY
FURNISHED
$4,950/mo
Total price
3 bd
1 ba
1,056 sqft
28 2nd Ave,
Oak Bluffs, MA 02557
APPLY INSTANTLY
FURNISHED
$3,500/mo
Total price
2 bd
2 ba
1,000 sqft
Address Not Disclosed,
Oak Bluffs, MA 02557
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$6,550/mo
Total price
4 bd
2 ba
1,520 sqft
107 Barnes Rd,
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

Skip to last item

Contact for price
1-2 bd
1-2 ba
490 Edgartown Vineyard Haven Rd #776f18ccb,
Edgartown, MA 02539
Contact for price
1-2 bd
1-2 ba
145 Main St #776f18ccb,
Vineyard Haven, MA 02568
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
APPLY INSTANTLY
FURNISHED
$3,500/mo
Total price
2 bd
2 ba
Address Not Disclosed,
Oak Bluffs, MA 02557
See more homes for rent in
Oak Bluffs
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Skip to first item

Off Market Homes Near 20 Paddock Rd

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SOLD
SEP 15, 2026
$1,340,000
2 bd
3 ba
1,864 sqft
51 Davis St,
Tisbury, MA 02568
Sandpiper Realty
SOLD
SEP 14, 2026
$2,890,000
5 bd
4.5 ba
3,881 sqft
10 N Bog Rd,
Edgartown, MA 02539
Vineyard Village Realty
SOLD
SEP 11, 2026
$1,050,000
4 bd
2 ba
1,513 sqft
1 Dodgers Hole Road,
Edgartown, MA 02539
Island Real Estate
SOLD
SEP 11, 2026
$1,450,000
2 bd
2.5 ba
2,000 sqft
7 Meetinghouse Village Way,
Edgartown, MA 02539
The Agency
SOLD
SEP 11, 2026
$1,185,000
1 bd
1 ba
546 sqft
61 Ocean Ave #4,
Oak Bluffs, MA 02557
Sandpiper Realty
SOLD
SEP 10, 2026
$2,100,000
4 bd
3 ba
2,348 sqft
82 Oyster Pond Rd,
Edgartown, MA 02539
Cronigs Real Estate
SOLD
SEP 8, 2026
$1,375,000
3 bd
3 ba
1,621 sqft
27 Laurel Ave,
Oak Bluffs, MA 02557
Lisa Sheehan, Berkshire Hathaway HomeServices Robert Paul Properties
SOLD
SEP 4, 2026
$1,700,000
3 bd
3 ba
2,293 sqft
10 Trotters Ln,
West Tisbury, MA 02575
Conroy & Company R.E., Inc.
SOLD
SEP 2, 2026
$905,000
2 bd
1 ba
1,074 sqft
22 Firehouse Ln,
Oak Bluffs, MA 02557
Compass LLC
SOLD
SEP 1, 2026
$625,000
2 bd
1 ba
814 sqft
10 Forest Cir,
Oak Bluffs, MA 02557
Cronigs Real Estate
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