53 Oakridge Drive, Westbrook, CT 06498
Property image
Property image
FOR SALE
3D VIEW
3.03 ACRES

$1,295,000

  • 4 Beds
  • 4 Baths
  • 4,937 sqft (on 3.03 acres)

53 Oakridge Drive, Westbrook, CT 06498

Est. Mortgage $9,052/mo*
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Home Highlights

Single-Family Home
Built in 1995
3.03 acre lot
$262/sqft
2 Car Garage

Local Information

  • Map ViewExplore the area around 53 Oakridge Drive.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Discover your own private oasis, this expansive custom-built home built on over 8 acres offers the perfect blend of privacy, comfort, and modern amenities. Featuring 4 bedrooms, 3 full bathrooms, 2 half bathrooms, and an oversized 2-car garage. Situated on the end of a private cul-de-sac the home is surrounded by peaceful natural beauty and thoughtfully designed for both everyday living and entertaining. Outdoor living is truly unmatched, with stunning decks and exterior stairways crafted from premium IPE Brazilian hardwood overlooking a private 3-acre, 30-foot-deep lake. Complete with a dramatic center fountain, lighting, and an aeration system, this remarkable setting creates a one-of-a-kind backdrop for relaxing, entertaining, or simply enjoying the serenity of your surroundings. Located just minutes from award-winning restaurants, shopping, marinas, and Westbrook's three town beaches, this hidden gem offers the rare opportunity to enjoy the best of Connecticut shoreline living while retreating to your own private sanctuary.
Last check for updates: about 6 hours ago
Listing courtesy of Cheryl Cook, (860) 575-8462
Re/Max Valley Shore, (860) 575-8462
Source: Smart MLS, MLS#24190188
Also Listed on Smart MLS.

Home Details for 53 Oakridge Drive

Interior Features

Interior Details
Basement: Full,Heated,Garage Access,Cooled,Partially Finished,Walk-Out AccessNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Bathroom, Den, Dining Room, Family Room, Kitchen, Living Room, Rec Play Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 3Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 4937 Square Feet
Appliances & Utilities
Utilities: Underground Utilities, Cable AvailableAppliances: Electric Cooktop, Oven, Refrigerator, Dishwasher, Trash Compactor, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main LevelRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane Windows
View
Has a ViewView: Water
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: DeckExterior: Outdoor Grill, Rain Gutters, LightingFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 5Parking: Attached,Paved,Driveway,Garage Door Opener,Private
Frontage
WaterfrontWaterfront: Waterfront, Lake, Walk to WaterOn Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 4308 Square FeetFinished Area (below surface): 629 Square Feet

Days on Market

Days on Market: 74

Property Information

Year Built
Year Built: 1995
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1039392

Price & Status

Price
List Price: $1,295,000Price Per Sqft: $262
Status Change & Dates
Possession Timing: Negotiable

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: WestbrookCommunity: Pond Meadow
School Information
Elementary School: Daisy IngrahamHigh School: Westbrook

Agent Information

Listing Agent
Listing ID: 24190188

Building

Building Area
Building Area: 4937 Square Feet

Community

Community Features: Golf, Paddle Tennis, Park, Shopping/Mall, Stables/Riding, Tennis Court(s)

HOA

No HOA

Lot Information

Lot Area: 3.03 Acres

Energy

Energy Efficiency Features: Windows

Miscellaneous

BasementMls Number: 24190188Attic: Floored, Walk-upWater ViewWater View: WaterAttribution Contact: (860) 575-8462Above Grade Unfinished Area: 4308Activation Date: Mon Jul 13 2026

Additional Information

GolfPaddle TennisParkShopping/MallStables/RidingTennis Court(s)

Around this home

What Locals Say about Westbrook

At least 32 Trulia users voted on each feature.

  • 89 % Say parking is easy

  • 88 % Say it's dog friendly

  • 87 % Say yards are well-kept

  • 80 % Say there's wildlife

  • 79 % Say kids play outside

  • 75 % Say people would walk alone at night

  • 72 % Say car is needed

  • 71 % Say there's holiday spirit

  • 66 % Say streets are well-lit

  • 66 % Say it's quiet

  • 62 % Say it's walkable to restaurants

  • 61 % Say neighbors are friendly

  • 61 % Say they plan to stay for at least 5 years

  • 53 % Say there are sidewalks

  • 39 % Say it's walkable to grocery stores

  • 34 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Annie Picardi
    "Beautiful area ,public transit is excellent,Resturant’s, shopping close by, Catholic Church is a bit far from our area, other houses of worship are close by,neighbors are friendly"
    0
    Flag
  • Annie Picardi
    "Great neighbors , awesome restaurants, amazing beach, easy accessibility to I 95 , walking distance to buses and shore line east train, under a mile and half to Amtrak station, nice churches, convient to three grocery stores, "
    0
    Flag
  • Annie Picardi
    "Great neighborhood nice friendly neighbors Cute dogs in the area easy to get to grocery stores retail stores and houses of worship "
    0
    Flag
  • Annie Picardi
    "Great neighborhood nice residents good shopping a nice variety of restaurants , nice movie theatre easy access to I95, only downfall is the coyotes"
    0
    Flag
  • Meredithawerner
    "Yrs family Friendly neighborhood great schools And quiet and safe for kids! Great schools and safe neighborhoods"
    1
    Flag
  • Meredithawerner
    "Great schools quiet family friendly neighborhood and cute small town low taxes easy beach access safe family friendly "
    1
    Flag
  • Rajay55
    "I have lived here for about 20 years, it’s ver safe. It’s closer to I95 and train station. Town beach is a great place to go anytime of the day."
    2
    Flag
  • Raj
    "I have been living her for 18 years, it is Nice quite small town. Town has clean and well maintained beach. There new library, schools are upgraded. I feel Safe living here. There is newly built train transit station for easier commute to New Haven and New London. There two outlet malls within 10 miles. There are Several of mom and pops restaurants for great food."
    7
    Flag
  • Navynique
    "There are many families and amazing schools, but most streets do not have sidewalks and are too winding and wooded to let kids play/ride bikes in the street."
    4
    Flag
  • Quincy S.
    "Yes, dog friendly place with many dog owners and dog walkers. Good places to go walking with dogs. "
    1
    Flag
  • Christian P.
    "I live there. It is important to note that there is almost nothing to do in Westbrook. At least because I don’t have a car I take the train or bus to work or to get around. Keep in mind that I strongly recommend getting your groceries delivered to your house if you don’t have a car."
    10
    Flag
  • Ruthlesstwo2
    "Neighborhood is very peaceful. The people are nice and the cars don’t speed in our neighborhood. And there are very few homes for sale near us. "
    2
    Flag
  • Ruthlesstwo2
    "I have lived in this neighborhood for 25 years, most of the neighbors are really nice people to live near. "
    1
    Flag
  • Matt D.
    "I work and live here with kids in the elementary school. Very safe and proper place to raise the youngins. The shoreline is beautiful and water is calm. Lot's of fun in the Summer and a private hideaway during the other Seasons."
    0
    Flag
  • Matt D.
    "Great for the kids and the Long Island Sound is clean. Islands for exploring and lots of friendly people"
    0
    Flag

Market trends in Westbrook

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
21
3MoM

Home Value

Trulia Estimate
$1.25M
Since last month
Decreased$5K (-0.4%)
Since last year
Increased$220K (+21.8%)
Since last sale
Increased$1M (+2,354.6%)
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 +134% in the last 10 years
MonthEstimated value
2026
September 2026$1.23M
August 2026$1.23M
July 2026$1.26M
June 2026$1.47M
May 2026$1.46M
April 2026$1.48M
March 2026$1.03M
February 2026$962K
January 2026$980K
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
210 Fishing Brook Road, Westbrook, CT
0.69
Single-Family Home
$733,000
02/03/26
5
3.5
2,494
199 Toby Hill Road, Westbrook, CT
0.72
Single-Family Home
$964,000
10/31/25
4
5.5
3,029
87 McVeagh Road, Westbrook, CT
0.27
Single-Family Home
$375,000
02/11/26
3
2
1,080
39 Churchill Lane, Westbrook, CT
0.45
Single-Family Home
$534,999
07/02/26
4
2.5
2,312
29 Meeting House Lane, Westbrook, CT
0.44
Single-Family Home
$575,000
06/18/26
5
3
2,552
405 Pond Meadow Road, Westbrook, CT
0.32
Single-Family Home
$400,000
06/26/26
3
2
1,281
843 Old Clinton Road, Westbrook, CT
1.10
Single-Family Home
$840,000
06/22/26
3
2.5
2,559
14 Halls Road, Westbrook, CT
1.12
Single-Family Home
$953,000
10/17/25
4
3.5
3,440
54 Lakeview Terrace, Westbrook, CT
1.07
Single-Family Home
$655,000
06/02/26
3
3
2,521
321 Old Clinton Road, Westbrook, CT
1.53
Single-Family Home
$945,000
12/09/25
4
3.5
3,961

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
500 Pond Meadow Road, Westbrook, CT 06498
0.12
$693,300
3
2.5
2,460
Off Market
85 McVeagh Road, Westbrook, CT 06498
0.22
$650,000
4
2.5
2,831
For Sale
87 McVeagh Road, Westbrook, CT 06498
0.27
$375,000
3
2
1,080
Recently Sold
405 Pond Meadow Road, Westbrook, CT 06498
0.32
$400,000
3
2
1,281
Recently Sold
55 Fishing Brook Road, Westbrook, CT 06498
0.35
$730,700
4
2.5
2,220
Off Market
19 Pond Circle Road, Westbrook, CT 06498
0.32
$790,400
4
2.5
2,674
Off Market
27 Pond Circle Road, Westbrook, CT 06498
0.32
$567,200
2
2
1,232
Off Market
369 Pond Meadow Road, Westbrook, CT 06498
0.39
$650,000
6
3
1,296
Recently Sold
343 Pond Meadow Road, Westbrook, CT 06498
0.41
$493,900
3
1.5
1,940
Off Market
110 Fishing Brook Road, Westbrook, CT 06498
0.45
$636,500
4
3
2,704
Off Market
243 Willard Avenue, Westbrook, CT 06498
0.42
$655,500
3
2.5
2,272
Off Market

Price and Tax history

DateEventPrice
Jul 13, 2026
Source: Smart MLS #24190188
Listed For Sale
$1,295,000
Apr 29, 2026
Source: Smart MLS #24166392
ListingRemoved
$1,475,000
Apr 19, 2026
Source: Smart MLS #24166392
Listed For Sale
$1,475,000
May 1, 1995
Source: N/A
Sold
$50,000

LGBTQ Local Legal Protections

Cheryl Cook, Re/Max Valley Shore, (860) 575-8462
Agent Phone: (860) 575-8462
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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Frequently asked questions about 53 Oakridge Drive

  • What is the estimated monthly payment for 53 Oakridge Drive?
    Based on a $1,295,000 list price with 20% down at today's rates, the estimated monthly payment for 53 Oakridge Drive in Westbrook, CT is approximately $9,163 (about $7,038 principal & interest, $2,050 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Westbrook?
    Residents describe Westbrook, CT as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See homes for sale in Westbrook, CT.
  • What are the closest schools to 53 Oakridge Drive?
    The closest schools to 53 Oakridge Drive in Westbrook, CT are Daisy Ingraham School (Pre-K/Elementary, rated 7/10), Westbrook High School (rated 7/10), Westbrook Middle School (rated 8/10).
  • What is 53 Oakridge Drive estimated to be worth?
    Trulia's estimated value for 53 Oakridge Drive in Westbrook, CT is $1,245,600.
  • Does 53 Oakridge Drive have air conditioning?
    Yes, 53 Oakridge Drive in Westbrook, CT has air conditioning.
  • Does 53 Oakridge Drive have laundry facilities?
    Yes, 53 Oakridge Drive in Westbrook, CT has in-unit laundry.
53 Oakridge Drive, Westbrook, CT 06498 is a 4 bedroom, 5 bathroom, 4,937 sqft single-family home built in 1995. This property is currently available for sale and was listed by Smart MLS on Jul 10, 2026. The MLS # for this home is MLS# 24190188.