38 Paddock Rd, Chilmark, MA 02557
OFF MARKET

38 Paddock Rd
Chilmark, MA 02557

  • 5 Beds
  • 5 Baths
  • 3,506 sqft (on 2.30 acres)

$4,079,200

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $22,660/mo*

$4,079,200

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $22,660/mo*
5 Beds
5 Baths
3,506 sqft
(on 2.30 acres)

Local Information

  • Map ViewExplore the area around 38 Paddock Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2019
Lot Size
2.3 acres
Living Area
3,506 sqft
Price/Sqft
$1,163

About this House

This single-family home is located at 38 Paddock Rd, Chilmark, MA. 38 Paddock Rd is in Chilmark, MA and in ZIP code 02557. This property has 5 bedrooms, 5 bathrooms and approximately 3,506 sqft of floor space. This property has a lot size of 2.30 acres and was built in 2019.
38 Paddock Rd, Chilmark, MA 02557 is a 5 bedroom, 5 bathroom, 3,506 sqft single-family home built in 2019. It last sold for $600,000 on Aug 15, 2019. It is currently off market. The Trulia Estimate is $4,079,200, with a rent estimate of $8,039/month.

Home Details for 38 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: 2019
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Lot Information

Lot Area: 2.30 acres

Price History for 38 Paddock Rd

DatePriceEventSource
08/15/2019$600,000Sold
N/A

Market trends in Oak Bluffs

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
54
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Property Tax and Assessment

Year2025
Tax$19,575
Assessment$3,876,300
Home facts updated by county records

Comparable Sales for 38 Paddock Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.43
Single-Family Home
$1,600,000
01/06/26
4
4.5
4,023
0.41
Single-Family Home
$2,900,000
03/30/26
4
4
5,169
0.43
Single-Family Home
$1,600,000
01/20/26
4
2.5
2,855
0.27
Single-Family Home
$1,449,000
08/19/25
3
2
2,284
0.36
Single-Family Home
$1,850,000
03/31/26
4
3
3,142
0.56
Single-Family Home
$1,687,500
07/10/26
3
2.5
2,862
0.56
Single-Family Home
$1,625,000
05/12/26
4
2.5
3,268
0.70
Single-Family Home
$1,885,000
07/29/26
5
3.5
2,527
0.78
Single-Family Home
$1,765,000
08/18/25
4
3.5
2,450
0.68
Single-Family Home
$1,500,000
09/22/25
4
3.5
2,336

Nearby homes

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Assigned Schools

These are the assigned schools for 38 Paddock 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

Sourced by Trulia users. 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 38 Paddock Rd

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Off Market Homes Near 38 Paddock Rd

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Frequently asked questions about 38 Paddock Rd

  • What is 38 Paddock Rd estimated to be worth?
    Trulia's estimated value for 38 Paddock Rd in Chilmark, MA is $4,079,200.
  • What is the price history for 38 Paddock Rd?
    38 Paddock Rd in Chilmark, MA last sold for $600,000 in August 2019.
  • Is Chilmark a buyer's or seller's market?
    Chilmark is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Chilmark?
    Residents describe Chilmark, MA as dog-friendly, well-kept, and walkable to restaurants. See recently sold homes in Chilmark, MA.
  • How big is the lot at 38 Paddock Rd?
    The lot at 38 Paddock Rd in Chilmark, MA is about 2.3 acres.