2 Overlook Dr, Westerly, RI 02891
OFF MARKET

2 Overlook Dr
Westerly, RI 02891

  • 6 Beds
  • 6.5 Baths
  • 6,390 sqft (on 1.12 acres)

$6,522,500

Trulia Estimate
as of Aug 11, 2026

$6,522,500

Trulia Estimate
as of Aug 11, 2026
6 Beds
6.5 Baths
6,390 sqft
(on 1.12 acres)

Local Information

  • Map ViewExplore the area around 2 Overlook Dr.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1910
Lot Size
1.12 acres
Living Area
6,390 sqft
Price/Sqft
$1,021

About this House

WATCH HILL, RI WATCH HILL WATER VIEW ESTATE set on a bluff overlooking the ocean and surrounded by broad lawns and gardens, this impeccably restored turn-of-the-century home is located within a quick walk of the beach and sports wonderful architectural details, a 10,000 bottle wine cellar and a fantastic pool and pool house. Jim Michalove $4.7M
2 Overlook Dr, Westerly, RI 02891 is a 6 bedroom, 8 bathroom, 6,390 sqft single-family home built in 1910. It last sold for $3,900,000 on May 29, 2020. It is currently off market. The Trulia Estimate is $6,522,500, with a rent estimate of $5,480/month.

Home Details for 2 Overlook Dr

Interior Features

Heating & Cooling
Heating: Baseboard, OilHeating Fuel: Baseboard
Interior Details
Number of Rooms: 13Types of Rooms: Dining Room, Family Room, Laundry Room
Appliances & Utilities
DishwasherRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: OtherExterior: Stone, Wood

Property Information

Year Built
Year Built: 1910
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 1.12 acres

Price History for 2 Overlook Dr

DatePriceEventSource
05/29/2020$3,900,000Sold
N/A
12/16/2018$4,500,000ListingRemovedAgent Provided
05/11/2018$4,500,000Listed For SaleAgent Provided
02/14/2018$4,500,000ListingRemovedAgent Provided
06/28/2017$4,500,000Listed For SaleAgent Provided
01/17/2015$4,700,000ListingRemovedAgent Provided
09/19/2014$4,700,000PriceChange
Agent Provided
04/29/2014$4,980,000Listed For SaleAgent Provided
01/01/2014$5,600,000ListingRemovedAgent Provided
04/25/2013$5,600,000Listed For SaleAgent Provided
12/22/2008$5,500,000Sold
N/A

Market trends in Westerly

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$581K
$71.97KMoM
Sale-to-List Price
—
Price per sq ft
$329
$70MoM
Available listings
67
6MoM
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Property Tax and Assessment

Year2025
Tax$39,494
Assessment$5,554,700
Home facts updated by county records

Comparable Sales for 2 Overlook Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
16 Yosemite Valley Rd, Westerly, RI
0.32
Single-Family Home
$2,759,000
09/24/25
9
9
10,136
13 Everett Ave, Westerly, RI
0.48
Single-Family Home
$8,200,000
09/29/25
6
3.5
5,063
7 Wapan Rd, Westerly, RI
0.52
Single-Family Home
$6,950,000
08/25/25
4
4.5
3,844
121 Avondale Rd, Westerly, RI
0.66
Single-Family Home
$4,500,000
05/11/26
8
10.5
10,966
112 Avondale Rd, Westerly, RI
0.80
Single-Family Home
$2,871,000
10/31/25
3
4.5
4,707
9 Arraquat Rd, Westerly, RI
0.61
Single-Family Home
$7,100,000
02/02/26
3
4
4,507
52 Avondale Rd, Westerly, RI
1.11
Single-Family Home
$4,075,000
02/27/26
4
3.5
4,149
21 E Hills Rd, Westerly, RI
0.88
Single-Family Home
$3,200,000
05/01/26
5
4
2,868
8 Pasadena Ave, Westerly, RI
0.53
Single-Family Home
$1,700,000
07/24/26
3
3
1,950
20 Westerly Rd, Westerly, RI
0.48
Single-Family Home
$3,700,000
09/26/25
2
2
912

Nearby homes

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Assigned Schools

These are the assigned schools for 2 Overlook Dr.
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 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

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Apartments for Rent

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Explore by feature - Pet Friendly

13 pet-friendly rentals in Westerly, RI

Explore by feature - Garage

17 rentals with a garage in Westerly, RI

Explore by feature - Air Conditioning

41 rentals with air conditioning in Westerly, RI

Explore by feature - Washer/dryer

33 rentals with a washer/dryer in Westerly, RI

Homes for sale near 2 Overlook Dr

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Off Market Homes Near 2 Overlook Dr

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Frequently asked questions about 2 Overlook Dr

  • What is 2 Overlook Dr estimated to be worth?
    Trulia's estimated value for 2 Overlook Dr in Westerly, RI is $6,522,500.
  • What is the price history for 2 Overlook Dr?
    2 Overlook Dr in Westerly, RI last sold for $3,900,000 in May 2020.
  • Is Westerly a buyer's or seller's market?
    Westerly is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Westerly?
    The median sale price in Westerly is $581K. That is down $71.97K from the prior month.
  • Does 2 Overlook Dr have laundry facilities?
    Yes, 2 Overlook Dr in Westerly, RI has laundry facilities.
  • How big is the lot at 2 Overlook Dr?
    The lot at 2 Overlook Dr in Westerly, RI is about 1.1 acres.