5 Overlook Dr, Old Saybrook, CT 06475
Property image
Property image
OFF MARKET

$1,450,000

Trulia Estimate
  • 5 Beds
  • 3 Baths
  • 5,834 sqft (on 1.85 acres)

5 Overlook Dr, Old Saybrook, CT 06475

Est. Refi. Payment $9,895/mo*
Refinance Your Home
Currently Off Market - Sold Jun 15, 2013 for $700,000

Home Value

Trulia Estimate
$1.45M
Since last month
Increased$14K (+0.9%)
Since last year
Increased$77K (+5.6%)
Since last sale
Increased$754K (+107.7%)
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 +53% in the last 10 years
MonthEstimated value
2026
August 2026$1.45M
August 2026$1.45M
July 2026$1.44M
June 2026$1.48M
May 2026$1.47M
April 2026$1.37M
March 2026$1.42M
February 2026$1.35M
January 2026$1.37M
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
21 Briarcliffe Trail, Old Saybrook, CT
0.26
Single-Family Home
$625,000
09/12/25
3
2.5
1,980
6 Fordham Trl, Old Saybrook, CT
0.57
Single-Family Home
$675,000
08/13/26
3
3
3,000
117 Ayers Point Road, Old Saybrook, CT
0.83
Single-Family Home
$695,000
11/21/25
4
2.5
2,824
6 Trolley Crossing, Old Saybrook, CT
0.71
Single-Family Home
$995,000
07/29/26
3
2.5
3,917
12 Hill Road, Old Saybrook, CT
0.90
Single-Family Home
$991,000
07/15/26
3
3
3,496
10 Trolley Crossing, Old Saybrook, CT
0.77
Single-Family Home
$1,065,000
06/18/26
3
2.5
3,376
11 Trolley Crossing, Old Saybrook, CT
0.86
Single-Family Home
$1,100,000
01/28/26
5
3.5
3,664
210 Springbrook Rd, Old Saybrook, CT
0.15
Single-Family Home
$240,000
02/20/26
2
2
1,431
227 Essex Road, Old Saybrook, CT
0.47
Single-Family Home
$410,000
12/22/25
3
1
1,032
9 Connally Drive, Old Saybrook, CT
1.45
Single-Family Home
$670,000
09/25/25
4
2.5
2,920

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
9 Overlook Drive, Old Saybrook, CT 06475
0.08
$1,759,500
4
4.5
3,556
Off Market
65 Springbrook Road, Old Saybrook, CT 06475
0.18
$652,700
4
2.5
3,098
Off Market
61 Springbrook Road, Old Saybrook, CT 06475
0.19
$550,000
3
3
1,296
For Sale
5 Watch Hill Road, Old Saybrook, CT 06475
0.20
$963,600
4
3.5
2,630
Off Market
7 Fourth Avenue Extension, Old Saybrook, CT 06475
0.28
$1,082,100
4
2.5
3,000
Off Market
5 Sunrise Avenue, Old Saybrook, CT 06475
0.28
$400,000
3
1
1,064
Recently Sold
10 Cliff Drive, Old Saybrook, CT 06475
0.25
$519,900
2
2
1,555
Off Market
21 Briarcliffe Trail, Old Saybrook, CT 06475
0.26
$668,100
3
2.5
1,980
Off Market
13 Sunset Avenue, Old Saybrook, CT 06475
0.36
$350,500
1
1
747
Off Market
81 Essex Road, Old Saybrook, CT 06475
0.37
$1,450,000
3
2
2,570
For Sale
16 Channelside Drive, Old Saybrook, CT 06475
0.39
$2,090,300
4
4.5
6,088
Off Market
9 2nd Avenue, Old Saybrook, CT 06475
0.40
$500,000
2
1
1,040
Recently Sold

Local Information

  • Map ViewExplore the area around 5 Overlook Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1989
1.85 acre lot
5,834 sqft
$249/sqft
Garage

About this House

This spectacular hilltop Nantucket-style Colonial has a wrap-around porch and CT River views. The versatile floor plan includes over 5,800 square feet of living area including a huge eat-in granite kitchen with island, cook-top, wall ovens and a family area with fireplace. In addition, there is also a formal dining room, a den or family room with fireplace and built-ins and a large living room with French doors that open to the patio and heated in-ground pool that round out the main level. Bedrooms and baths are on the upper levels including a master bedroom suite with walk-in closet, en-suite bath and balcony with views of the River. The grounds are landscaped with pretty plantings and stone walls and a detached 3 car garage has a fully finished bonus room above with separate entrance which can have a variety of uses. Make this your own private paradise high above it all. Only minutes to town, commuter roads and railway station. Call David Genovali for more information on this wonderful property -- 860-227-7714. Call today!!
5 Overlook Dr, Old Saybrook, CT 06475 is a 5 bedroom, 3 bathroom, 5,834 sqft single-family home built in 1989. It last sold for $700,000 on Jun 15, 2013. More recently, it was listed as a rental in July 2011 with an asking price of $4,500 per month. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,450,000.

Home Details for 5 Overlook Dr

Interior Features

Interior Details
BasementAtticNumber of Rooms: 8
Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: OtherPatio
Pool
Pool
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1989
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.85 acres

Price and Tax history

DateEventPrice
Jun 15, 2013
Source: Smart MLS #M9138128
Sold
$700,000
Dec 30, 2012
Source: Agent Provided
PriceChange
$799,900
Price decreased by 11%
Jun 26, 2012
Source: Agent Provided
Listed For Sale
$899,900
Jan 18, 2012
Source: Agent Provided
PriceChange
$3,500
Price decreased by 22%
Jul 23, 2011
Source: Agent Provided
Listed For Rent
$4,500

Market trends in Old Saybrook

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
55
4MoM

Around this home

What Locals Say about Old Saybrook

At least 42 Trulia users voted on each feature.

  • 88 % Say yards are well-kept

  • 88 % Say it's dog friendly

  • 84 % Say there's holiday spirit

  • 84 % Say parking is easy

  • 78 % Say car is needed

  • 75 % Say people would walk alone at night

  • 66 % Say they plan to stay for at least 5 years

  • 61 % Say neighbors are friendly

  • 61 % Say kids play outside

  • 60 % Say there's wildlife

  • 58 % Say it's quiet

  • 57 % Say streets are well-lit

  • 56 % Say it's walkable to restaurants

  • 52 % Say there are sidewalks

  • 51 % Say there are community events

  • 43 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Diva For Life
    "I think is great to live here I think it safe for family and I hope I can move here with my family soon "
    0
    Flag
  • Trulia User
    "It’s a safe town, good schools. A lot of different activities and programs available for kids from toddlers to high school. The schools are located in convenient safe areas of the town. Lower traffic areas. Pedestrians are plentiful and kids riding bikes to and from school. Several beaches that are great for family gatherings as well as private time to yourself. Everything you need to bring your family up in a quiet shoreline community. Public transportation is available with a trolly during the months of spring and summer. The library is conveniently located next to the elementary school. Plenty of in town shopping available and plenty of great restaurants. Ice cream as well. "
    1
    Flag
  • Jocelynne B. .
    "It’s a safe place to live and the school system is very good. Small class rooms and everyone knows everyone. "
    0
    Flag
  • Tyfinkbus
    "I have lived in Old Saybrook for 15 years and the people are very friendly. The area is peaceful and very well maintained."
    0
    Flag
  • John D.
    "I commute by my car, motorcycle, scooter, or bicycle. I do not use public transportation. I also walk to the beach or downtown. "
    1
    Flag
  • J Jenkins
    "I lived in this neighborhood for 40 yrs, I love it here, we have had our children here and now have there own homes close by. We are only 1.1 miles from I-95, 1.5 to the supermarket, 2 miles to main St and 3 miles to the beach. A great area."
    0
    Flag
  • Svasmatics
    "I moved to Old Saybrook because I work in town. It is close to I-95 and Route9. The town itself and traffic is very different from winter to summer. Summer brings a lot of snow birds and visitors. Stores, traffic, commotion in general is heavier in the summer months. Food prices also go up in the summer."
    2
    Flag
  • Tony
    "I've lived in the area for over 12 years. Everything (shopping, dining, etc.) are all within walking distance, with plenty of sidewalks. most neighbors are friendly, and willing to lend a hand when needed."
    5
    Flag
  • Ali F.
    "No sidewalks. Some neighbors let dogs walk off the leash. There are Coyotes or coy dogs that are found to live around the marsh areas. I have had squirrels in my attic three times even after sealing. "
    6
    Flag
  • Ali F.
    "Love our neighborhood. Close walking to center of town. Neighbors are friendly. Birds, rabbits and squirrels. Sometimes can see coyote or deer. "
    0
    Flag
  • Karen E. d.
    "Train station is within walking distance with newly installed sidewalks and street lighting. I95 is easily accessible for commutes to New York or north. Personally, I am able to walk to my job in the downtown area. "
    0
    Flag
  • Annette M.
    "Wonderful beach community for families and singles. I rent here but most people own and the community is very tight knit and supportive."
    0
    Flag
  • Karen E. d.
    "Lots of friendly dogs in area. Most on leashes or in fenced yards. Some of the Main St. businesses put water out for our four legged friends. "
    1
    Flag
  • Bean_laura
    "Lots of other dogs. Dog parks. Pet stores. Fire hydrants. Pet friendly restaurants and bars. Pet friendly shopping."
    1
    Flag
  • Jocelynne B.
    "It’s a quiet neighborhood with no issues. Saybrook is safe and the school system is excellent. I enjoyed growing up and living in Saybrook. It’s a very friendly community."
    0
    Flag
  • Kearney j.
    "I've lived here for 25 years. it is a safe and welcoming community. pride I. home and property is prevalent everywhere. neighbors are friendly and supportive."
    0
    Flag
  • Rose H. M.
    "Fenwood beach is one of the most desirable areas along the shore, with a private beach, bordering Fenwick golf course, with views of the Saybrook lighthouses from the shore. The residents have lots of social activities, such as the summer lobster bake on the beach. Residents often ride golf carts around the neighborhood and to the beach. Fenwood beach is also a short drive into the quaint town center and to Saybrook Point. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5 Overlook Dr

  • What is 5 Overlook Dr estimated to be worth?
    Trulia's estimated value for 5 Overlook Dr in Old Saybrook, CT is $1,450,000.
  • What is the price history for 5 Overlook Dr?
    5 Overlook Dr in Old Saybrook, CT last sold for $700,000 in June 2013.
  • Is Old Saybrook a buyer's or seller's market?
    Old Saybrook is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Old Saybrook?
    Residents describe Old Saybrook, CT as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See recently sold homes in Old Saybrook, CT.
  • Does 5 Overlook Dr have a pool?
    Yes, 5 Overlook Dr in Old Saybrook, CT has a pool.
  • How big is the lot at 5 Overlook Dr?
    The lot at 5 Overlook Dr in Old Saybrook, CT is about 1.9 acres.

Explore by feature - Pet Friendly

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Apartments for Rent

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Off Market Homes Near 5 Overlook Dr

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Homes for sale near 5 Overlook Dr

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