20 Leeward Dr, Westerly, RI 02891
Property image
Property image
OFF MARKET

$1,309,900

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 3,402 sqft (on 0.46 acres)

20 Leeward Dr, Westerly, RI 02891

Refinance Your Home
Currently Off Market - Sold Mar 14, 2019 for $620,000

Home Value

Trulia Estimate
$1.31M
Since last month
Increased$56K (+4.5%)
Since last year
Increased$152K (+13.3%)
Since last sale
Increased$679K (+109.5%)
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 +137% in the last 10 years
MonthEstimated value
2026
August 2026$1.3M
July 2026$1.24M
June 2026$1.27M
May 2026$1.24M
April 2026$1.24M
March 2026$1.24M
February 2026$1.2M
January 2026$1.18M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
4 Shore Rd, Westerly, RI
0.24
Single-Family Home
$970,000
08/11/26
3
3
2,738
26 Windward Dr, Westerly, RI
0.18
Single-Family Home
$1,270,000
08/07/26
3
2.5
3,510
7 Leeward Dr, Westerly, RI
0.09
Single-Family Home
$1,260,000
05/11/26
4
3
2,263
1 Turtleback Rd, Westerly, RI
0.28
Single-Family Home
$875,000
12/29/25
3
4
2,569
4 Ice Pond Rd, Westerly, RI
0.16
Single-Family Home
$1,800,000
01/08/26
5
3
3,517
32 Trolley Ln, Westerly, RI
0.61
Single-Family Home
$855,000
09/26/25
3
2
2,366
2 Quail Run, Westerly, RI
0.48
Single-Family Home
$1,150,000
10/07/25
3
1.5
2,451
47 Shore Rd, Westerly, RI
0.47
Single-Family Home
$977,500
10/31/25
3
2
1,830
15 Windward Dr, Westerly, RI
0.09
Single-Family Home
$1,450,000
09/30/25
5
3.5
2,305
38 Setting Sun Dr, Westerly, RI
0.19
Single-Family Home
$1,595,000
09/05/25
2
3.5
4,065

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
18 Leeward Dr, Westerly, RI 02891
0.02
$1,471,300
4
3
3,030
Off Market
16 Setting Sun Dr, Westerly, RI 02891
0.07
$1,164,500
3
2
1,953
Off Market
15 Windward Dr, Westerly, RI 02891
0.09
$1,385,500
5
3.5
2,305
Off Market
6 Setting Sun Dr, Westerly, RI 02891
0.16
$865,700
3
2
1,856
Off Market
45 Ice Pond Ln, Oak Bluffs, MA 02557
0.15
$3,890,700
1
2.5
1,560
Off Market
3 Setting Sun Dr, Westerly, RI 02891
0.18
-
-
-
-
Off Market
26 Windward Dr, Westerly, RI 02891
0.18
$1,270,000
3
2.5
3,510
Recently Sold
38 Setting Sun Dr, Westerly, RI 02891
0.19
$1,855,200
2
3.5
4,065
Off Market
109 Watch Hill Rd, Westerly, RI 02891
0.24
$2,250,000
4
4.5
3,923
Recently Sold
4 Shore Rd, Westerly, RI 02891
0.24
$970,000
3
3
2,738
Recently Sold
No Bottom Ridge Rd, Westerly, RI 02891
0.25
-
-
-
-
Off Market
18 No Bottom Ridge Rd, Westerly, RI 02891
0.29
$1,600,000
-
-
-
For Sale

Local Information

  • Map ViewExplore the area around 20 Leeward Dr.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1984
Lot Size
0.46 acres
Living Area
3,402 sqft
Price/Sqft
$385
Parking
Garage

About this House

A fabulous home located near the Avondale section of Westerly minutes from Watch Hill. This Nantucket Style home is well maintained, has a great kitchen, double ovens, granite, stainless appliances.Other features include: Irrigation system,Central air, gas fireplaces , "instant on" Generator, smart home technology and Nest Thermostats. Charming surroundings abound including a wonderful outside porch and patio. Make this your full time home or your summer residence.
20 Leeward Dr, Westerly, RI 02891 is a 3 bedroom, 3 bathroom, 3,402 sqft single-family home built in 1984. It last sold for $620,000 on Mar 14, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,309,900, with a rent estimate of $4,049/month.

Home Details for 20 Leeward Dr

Interior Features

Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 9

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1984
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.46 acres

Price and Tax history

DateEventPrice
Mar 14, 2019
Source: StateWide MLS RI #1198658
Sold
$620,000
Jul 20, 2018
Source: Agent Provided
Listed For Sale
$649,000
Nov 1, 2013
Source: Agent Provided
ListingRemoved
$599,000
Oct 31, 2013
Source: N/A
Sold
$537,500
Oct 26, 2011
Source: Agent Provided
ListingRemoved
$625,000

Market trends in Westerly

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
3MoM

Around this home

What Locals Say about Westerly

At least 172 Trulia users voted on each feature.

  • 86 % Say it's dog friendly

  • 85 % Say car is needed

  • 76 % Say parking is easy

  • 71 % Say people would walk alone at night

  • 69 % Say yards are well-kept

  • 68 % Say it's walkable to restaurants

  • 68 % Say there's holiday spirit

  • 65 % Say streets are well-lit

  • 64 % Say kids play outside

  • 59 % Say there are sidewalks

  • 58 % Say they plan to stay for at least 5 years

  • 55 % Say neighbors are friendly

  • 53 % Say it's walkable to grocery stores

  • 52 % Say it's quiet

  • 50 % Say there's wildlife

  • 28 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trever625
    "Great place to live, I would recommend doing some research and driving around to find the best area suitable for kids. But all in all it’s a great town with close proximity to the beaches and plenty to do. "
    0
    Flag
  • Stuart Whitcomb
    "There are many outdoor opportunities nearby, like short hikes; activities through our beautiful library and in the adjoining park; and of course the ocean is a short drive from downtown. For older children there are many summer job opportunities nearby, and the downtown is safe and offers a few good options for window shopping and coffee drinks."
    0
    Flag
  • V2rp26znzc
    "Westerly is a great town with beautiful Wilcox Park, beaches, great restaurants, great schools, churches, well kept roads and sidewalks. Downtown Westerly has lots to offer with great jewelry stores, gelato shop, women’s clothing, children’s clothing, bookstores, and a movie theater, "
    0
    Flag
  • Tinamarie Plenninger
    "More dog parks friendly places to bring a dog . I don’t have a dog but family members do. More trash cans for disposables "
    0
    Flag
  • Trulia User
    " It’s beautiful. You feel the energy of the ocean every day and are subject to Mother Nature’s will. "
    0
    Flag
  • Erich.h.fischer86
    "love living so close to the downtown area, friendly neighborhood, close to the beach, close to Mystic and Stonington "
    5
    Flag
  • Heidi P.
    "Highway driving for about 25 minutes; Very easy on and off and not hilly just very straightforward."
    2
    Flag
  • Mary G.
    "Summer pops, downtown shutdown, beach events, movies in the park, drive in, duck races, ice skating ring, "
    2
    Flag
  • Mary G.
    "Side walks and people clean up after their dogs..... friendly people and the Wilcox park is a nice place to walk"
    2
    Flag
  • Scott G.
    "Nice downtown area, close to beautiful beaches and plenty of shopping. Something for everyone with small town charm"
    0
    Flag
  • Genevieve.boas
    "Great areas for walking dogs. Quiet and private. Walking trails and beaches abound along with parks. Beautiful weather."
    0
    Flag
  • Bain682
    "Quiet streets to walk your dog up and down. Plenty of other dog owners around the neighborhood. Dog park in town and other parks plus the beach. Lots of fun items."
    3
    Flag
  • Kathy M.
    "No dogs allowed at my condo, not even to visit. Hard to find apartments that allow dogs also. Nice area to take walks with the dog. There is a dog park also"
    2
    Flag
  • Jean P.
    "We have community fairs.. plays functions either in our park or plenty of summer activities down and around the beaches. extremely family oriented. "
    2
    Flag
  • Unspecified
    "Nosy neighbors!!! Otherwise very great neighborhood. Not fond of the school system and local sober homes."
    1
    Flag
  • Julia
    "The beach town is absolutely gorgeous and so much fun and it’s a great family area to raise kids. Everyone is related in this small Italian town which makes it a special place"
    0
    Flag
  • Davisphilip1717
    "Do you see dogs being walked on a regular basis. They do not seem to be any issues. I have never seen anyone not clean up after their dog."
    2
    Flag
  • Townshorerentals
    "Great place Beautiful beach community everybody would love living here I am a realtor I sell a lot of homes. Come to westerly "
    2
    Flag
  • Malu27
    "Very friendly neighborhood close to town. People take pride in the community and it has a small town feel. Great place to raise a family."
    0
    Flag
  • CC
    "It’s clean. Everyone is nice. You live by the water. "
    0
    Flag
  • Gabriela A.
    "My commute is an 8 minute drive to Watch Hill. I do not see any public transportation during the winter. "
    0
    Flag
  • Morgan K.
    "Nice quaint small town. Amazing ymca and beautiful park right in the center of town. The town decorates for Christmas which is nice. Also the beaches here are accessible and pretty"
    0
    Flag
  • Jovani H.
    "Safe, quiet , and respectful Communtiy. Very clean and beautiful areas around. Summer is always best with beaches and parks."
    2
    Flag
  • Christina C.
    "bus stop is close, mcquades is near by and it's a great local grocery store with delicious foods. also near downtown where there are lots of shops, restaurants, bars, the public library, and most importantly the Wilcox Park. "
    0
    Flag
  • Johnrestelli
    "good quiet community small town living friendly decent taxes great in the summer for beaches can get a little overcrowded "
    0
    Flag
  • Julieserpa62085
    "Westerly is a BEACH COMMUNITY! 😄👙😄. You can be at any corner of this town but u are never a 15 car ride away from the beach ! "
    0
    Flag
  • Jean P.
    "I lived in this neighborhood for one year and absolutely love it I am now looking to stay in this location. searching to rent a home home or renting a larger apartment or possibly purchasing."
    0
    Flag
  • Rory d.
    "Close to beach & river. Very friendly people. Walking distance to cafe, docks, nature preserve; biking distance to village, ice cream, and beaches."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 20 Leeward Dr

  • What is 20 Leeward Dr estimated to be worth?
    Trulia's estimated value for 20 Leeward Dr in Westerly, RI is $1,309,900.
  • What is the price history for 20 Leeward Dr?
    20 Leeward Dr in Westerly, RI last sold for $620,000 in March 2019.
  • Is Westerly a buyer's or seller's market?
    Westerly is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Westerly?
    Residents describe Westerly, RI as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Westerly, RI.
  • Does 20 Leeward Dr have air conditioning?
    Yes, 20 Leeward Dr in Westerly, RI has air conditioning.
  • How big is the lot at 20 Leeward Dr?
    The lot at 20 Leeward Dr in Westerly, RI is about 0.46 acres (20,125 sq ft).

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

6 rentals with an outdoor space in Westerly, RI

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Off Market Homes Near 20 Leeward Dr

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