5 Lakeside Dr, Weston, CT 06883
Property image
Property image
OFF MARKET

$1,601,000

Trulia Estimate
  • 5 Beds
  • 3 Baths
  • 3,983 sqft (on 2.27 acres)

5 Lakeside Dr, Weston, CT 06883

Est. Refi. Payment $10,894/mo*
Refinance Your Home
Currently Off Market - Sold Apr 8, 2010 for $850,000

Home Value

Trulia Estimate
$1.6M
Since last month
Decreased$29K (-1.7%)
Since last year
Increased$63K (+4%)
Since last sale
Increased$776K (+91.3%)
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 +100% in the last 10 years
MonthEstimated value
2026
September 2026$1.63M
August 2026$1.64M
July 2026$1.65M
June 2026$1.68M
May 2026$1.67M
April 2026$1.62M
March 2026$1.61M
February 2026$1.54M
January 2026$1.52M
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
193 Newtown Turnpike, Weston, CT
0.14
Single-Family Home
$1,340,000
12/15/25
4
4.5
4,100
4 November Trail, Weston, CT
0.35
Single-Family Home
$1,585,000
09/19/25
4
3
4,368
12 Mountain View Drive, Weston, CT
0.74
Single-Family Home
$1,213,000
06/15/26
5
2.5
4,092
59 September Lane, Weston, CT
0.52
Single-Family Home
$1,700,000
09/11/26
5
3.5
4,476
10 Hyde Ridge Road, Weston, CT
0.47
Single-Family Home
$1,620,000
05/29/26
4
3.5
3,310
7 Birch Hill Road, Weston, CT
0.53
Single-Family Home
$1,925,000
05/26/26
5
3
3,481
326 Georgetown Road, Weston, CT
0.49
Single-Family Home
$1,799,000
12/03/25
5
4.5
4,749
14 White Oak Ln, Weston, CT
0.68
Single-Family Home
$1,450,000
06/30/26
5
4.5
3,987
30 Lords Highway, Weston, CT
0.22
Single-Family Home
$3,400,000
04/20/26
5
5
6,670
4 Trails End Road, Weston, CT
0.83
Single-Family Home
$1,440,000
05/07/26
5
3.5
3,888

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
193 Newtown Turnpike, Weston, CT 06883
0.14
$1,340,000
4
4.5
4,100
Recently Sold
19 October Drive, Weston, CT 06883
0.17
$1,580,200
3
3
3,082
Off Market
25 Lakeside Drive, Weston, CT 06883
0.14
$1,649,000
5
3.5
2,926
Off Market
30 Lords Highway, Weston, CT 06883
0.22
$3,400,000
5
5
6,670
Recently Sold
170 & 172 Newtown Turnpike, Weston, CT 06883
0.26
$3,676,900
5
6
7,331
Off Market
173 Newtown Turnpike, Weston, CT 06883
0.25
$1,420,900
4
2.5
3,670
Off Market
152 Old Hyde Road, Weston, CT 06883
0.21
$1,743,100
5
4.5
6,226
Off Market
124 Old Hyde Road, Weston, CT 06883
0.23
$2,262,900
4
5
3,700
Off Market
143 Old Hyde Road, Weston, CT 06883
0.22
$1,795,000
6
4
4,900
For Sale
166 Newtown Turnpike, Weston, CT 06883
0.29
$1,781,800
5
4.5
4,938
Off Market
9 November Trail, Weston, CT 06883
0.30
$2,573,500
6
5.5
6,349
Off Market
28 November Trail, Weston, CT 06883
0.29
$1,529,800
4
3.5
4,474
Off Market

Local Information

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

Home Highlights

Single-Family Home
Built in 1969
2.27 acre lot
3,983 sqft
$402/sqft
Garage

About this House

MOTIVATED SELLER!! Will consider any reasonable offer. Vacation all year in this classic home in sought after "Lakeside". This "hidden gem" is located along the West Branch of the Saugatuck River, less than a mile from Weston's celebrated schools, on a private cul-de-sac of only 14 homes. A beautiful colonial, freshly painted outside/inside, spacious updated 5Brs, updated 2 full and 2 1/2 Bths, flexible living space that will easily adjust to your living style. Hardwood floors throughout, eat-in-kitchen, 2 fireplaces, sliders and bay windows and deck overlooking the captivating views of the lake where you can kayak, canoe, swim, fish or even ice skate! Lower level completely renovated with a separate gym, family room , bath, laundry room and slider out to the patio, "doll house", large yard and access to your own legal dock (get info from agent). Just some of the improvements - new sub-electrical panel for generator, complete new security system, new curtain drains surrounding house, new septic pipes to 3 tanks...and much, MUCH more.
5 Lakeside Dr, Weston, CT 06883 is a 5 bedroom, 4 bathroom, 3,983 sqft single-family home built in 1969. It last sold for $850,000 on Apr 8, 2010. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,601,000, with a rent estimate of $7,349/month.

Home Details for 5 Lakeside Dr

Interior Features

Interior Details
BasementNumber of Rooms: 10Types of Rooms: Laundry Room
Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDisposalMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodPatio
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1969Year Updated: 2003
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.27 acres

Price and Tax history

DateEventPrice
Feb 6, 2020
Source: Agent Provided
ListingRemoved
$787,000
Oct 28, 2019
Source: Agent Provided
PriceChange
$787,000
Price decreased by 0%
Oct 13, 2019
Source: Agent Provided
PriceChange
$789,900
Price decreased by 3%
Sep 28, 2019
Source: Agent Provided
Listed For Sale
$815,000
Sep 24, 2010
Source: Agent Provided
ListingRemoved
$899,000

Market trends in Weston

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
46
1MoM

Around this home

What Locals Say about Weston

At least 40 Trulia users voted on each feature.

  • 98 % Say car is needed

  • 96 % Say yards are well-kept

  • 95 % Say parking is easy

  • 95 % Say it's quiet

  • 85 % Say there's wildlife

  • 80 % Say it's dog friendly

  • 73 % Say there's holiday spirit

  • 62 % Say neighbors are friendly

  • 62 % Say people would walk alone at night

  • 56 % Say kids play outside

  • 52 % Say they plan to stay for at least 5 years

  • 47 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Nikkivines
    "it's gorgeous and rural. it's that perfect combination of large its and a really tight knit community."
    3
    Flag
  • Unspecified
    "I work from home, so commuting isn’t an issue for me. We do have several restaurants, pharmacies and grocery stores within 5-10 minutes. "
    4
    Flag
  • Romulo V.
    "Each house has lots of outdoor space (2-acre law) which is perfect for dogs. There’re dog parks near the area which is great for dog interaction. "
    2
    Flag
  • Lisa_singer
    "Great school system, supportive, welcoming community. Nature Preserve, Historic Society, Pond, cute town center"
    1
    Flag
  • mhcampbell73
    "The town is gear toward families with children as opposed to couples with grown children or retirees. The schools and activities for kids are top notch. However, the cost of living is very high due to the property taxes assessed to support the school system. There is no industry and only a small business base to defray taxes in this primarily bedroom community."
    0
    Flag
  • mhcampbell73
    "With two acre zoning, houses are spaced apart which is why walkability is low. But shopping and restaurants abound in neighboring towns with good access. The school system would rival many private schools. Lots of trees and wildlife. It's just plain beautiful."
    0
    Flag
  • ronfin
    "School are superb, train to Grand Central is 20 minutes away, (1h train ride), safe and child friendly. 15-25 minutes from great restaurants in Westport, Norwalk and Wilton"
    0
    Flag
  • Lindsayjillmarcus
    "I moved to Weston for the town's amazing school system. The Weston community is top notch and the people are friendly. I chose Weston over Westport as this town has so much charm."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5 Lakeside Dr

  • What is 5 Lakeside Dr estimated to be worth?
    Trulia's estimated value for 5 Lakeside Dr in Weston, CT is $1,601,000.
  • What is the price history for 5 Lakeside Dr?
    5 Lakeside Dr in Weston, CT last sold for $850,000 in April 2010.
  • Is Weston a buyer's or seller's market?
    Weston is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Weston?
    Residents describe Weston, CT as well-kept, easy to park in, and quiet. Most residents say you need a car. See recently sold homes in Weston, CT.
  • Does 5 Lakeside Dr have air conditioning?
    Yes, 5 Lakeside Dr in Weston, CT has air conditioning.
  • Does 5 Lakeside Dr have laundry facilities?
    Yes, 5 Lakeside Dr in Weston, CT has laundry facilities.

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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Off Market Homes Near 5 Lakeside Dr

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