21 Paddock Rd, Oak Bluffs, MA 02557
Property image
Property image
OFF MARKET

$4,304,400

Trulia Estimate
  • 6 Beds
  • 5.5 Baths
  • 4,353 sqft (on 2.33 acres)

21 Paddock Rd, Oak Bluffs, MA 02557

Est. Refi. Payment $24,433/mo*
Refinance Your Home
Currently Off Market - Sold Aug 7, 2020 for $600,000

Home Value

Trulia Estimate
$4.3M
Since last month
$200 (0%)
Since last year
Decreased$168K (-3.8%)
Since last sale
Increased$4M (+617.4%)
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 +87% in the last 10 years
MonthEstimated value
2026
August 2026$4.3M
August 2026$4.3M
July 2026$4.3M
June 2026$4.32M
May 2026$4.25M
April 2026$4.22M
March 2026$4.22M
February 2026$4.19M
January 2026$4.12M
2025
2024
2023
2022
2021
2020

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
63 Bayes Hill Rd, Oak Bluffs, MA
0.26
Single-Family Home
$2,900,000
03/30/26
4
4
5,169
44 Tiffany Dr, Oak Bluffs, MA
0.35
Single-Family Home
$1,600,000
01/06/26
4
4.5
4,023
5 Bayes Hill Circle, Oak Bluffs, MA
0.28
Single-Family Home
$1,600,000
01/20/26
4
2.5
2,855
7 S Meadow Ln, Oak Bluffs, MA
0.36
Single-Family Home
$1,850,000
03/31/26
4
3
3,142
7 Upper Meadow Ln, Oak Bluffs, MA
0.46
Single-Family Home
$1,625,000
05/12/26
4
2.5
3,268
103 Meadow View Rd, Oak Bluffs, MA
0.59
Single-Family Home
$1,687,500
07/10/26
3
2.5
2,862
18 Puritan Dr, Oak Bluffs, MA
0.65
Single-Family Home
$1,885,000
07/29/26
5
3.5
2,527
35 Tower Ridge Rd, Oak Bluffs, MA
0.73
Single-Family Home
$1,700,000
11/03/25
3
4
2,558
126 Border Rd, Tisbury, MA
0.83
Single-Family Home
$1,685,000
10/09/25
3
3
2,251
515 Edgartown Rd, Tisbury, MA
1.16
Single-Family Home
$1,500,000
03/03/26
6
3
5,418

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
0.06
$1,895,000
6
6.5
4,500
For Sale
25 Paddock Rd #23, Oak Bluffs, MA 02557
0.06
-
-
-
-
Off Market
40 Paddock Rd #18, Oak Bluffs, MA 02557
0.11
-
-
-
-
Off Market
34 Paddock Rd, Oak Bluffs, MA 02557
0.11
-
-
-
-
Off Market
14 High Meadow Ln, Oak Bluffs, MA 02557
0.19
$1,750,000
3
3
1,932
For Sale
19 Tiffany Dr, Oak Bluffs, MA 02557
0.27
$2,143,100
4
2.5
2,585
Off Market
4 High Meadow Ln, Oak Bluffs, MA 02557
0.25
$2,260,000
4
3.5
2,810
For Sale
63 Bayes Hill Rd, Oak Bluffs, MA 02557
0.26
$2,900,000
4
4
5,169
Recently Sold
11 High Meadow Ln, Oak Bluffs, MA 02557
0.25
$1,674,400
4
2.5
1,811
Off Market
5 Bayes Hill Circle, Oak Bluffs, MA 02557
0.28
$1,600,000
4
2.5
2,855
Recently Sold
44 Paddock Rd #20, Oak Bluffs, MA 02557
0.27
-
-
-
-
Off Market
44 Tiffany Dr, Oak Bluffs, MA 02557
0.35
$2,800,000
4
4.5
4,023
For Sale

Local Information

  • Map ViewExplore the area around 21 Paddock Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2020
2.33 acre lot
4,353 sqft
$989/sqft

About this House

THE PRESERVE AT THE WOODLANDS is Oak Bluff's newest luxury enclave nestled in a beautiful woodland setting with bucolic meadow views and a lovely pond. This gorgeous property connects with miles of walking/hiking trails and a bike path to Farm Neck Golf Club and all three down island towns and beaches. There are underground utilities and town water in place. Carefully crafted association covenants have been developed to preserve the character, integrity and value of this distinctive property. Your new construction dream home waits!
21 Paddock Rd, Oak Bluffs, MA 02557 is a 6 bedroom, 6 bathroom, 4,353 sqft single-family home built in 2020. It last sold for $600,000 on Aug 7, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,304,400.

Home Details for 21 Paddock Rd

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 2020
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 2.33 acres

Price and Tax history

DateEventPrice
Aug 7, 2020
Source: LINK #36690
Sold
$600,000
Jun 30, 2020
Source: Agent Provided
Pending
$2,397,000
Jun 1, 2020
Source: Agent Provided
Listed For Sale
$2,397,000

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

Frequently asked questions about 21 Paddock Rd

  • What is 21 Paddock Rd estimated to be worth?
    Trulia's estimated value for 21 Paddock Rd in Oak Bluffs, MA is $4,304,400.
  • What is the price history for 21 Paddock Rd?
    21 Paddock Rd in Oak Bluffs, MA last sold for $600,000 in August 2020.
  • 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.
  • Does 21 Paddock Rd have air conditioning?
    Yes, 21 Paddock Rd in Oak Bluffs, MA has air conditioning.
  • How big is the lot at 21 Paddock Rd?
    The lot at 21 Paddock Rd in Oak Bluffs, MA is about 2.3 acres.

Explore by feature - Air Conditioning

Explore by feature - Washer/dryer

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

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 21 Paddock Rd

Skip to last item
Skip to first item

Homes for sale near 21 Paddock Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item