104 Five Mile River Rd, Darien, CT 06820
Property image
Property image
OFF MARKET

$5,936,800

Trulia Estimate
  • 5 Beds
  • 5 Baths
  • 4,945 sqft (on 0.72 acres)

104 Five Mile River Rd, Darien, CT 06820

Tokeneke
Est. Refi. Payment $40,194/mo*
Refinance Your Home
Currently Off Market - Sold Nov 14, 2016 for $3,550,000

Home Value

Trulia Estimate
$5.94M
Since last month
Decreased$113K (-1.8%)
Since last year
Increased$494K (+8.9%)
Since last sale
Increased$2M (+69.5%)
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 +77% in the last 10 years
MonthEstimated value
2026
September 2026$6.02M
August 2026$6.11M
July 2026$6.13M
June 2026$6.01M
May 2026$5.9M
April 2026$5.83M
March 2026$5.83M
February 2026$5.65M
January 2026$5.56M
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
90 Five Mile River Road, Darien, CT
0.12
Single-Family Home
$4,250,000
05/08/26
5
4.5
5,060
128 Five Mile River Road, Darien, CT
0.17
Single-Family Home
$3,464,000
07/16/26
5
3.5
2,478
13 Edgehill Drive, Darien, CT
0.31
Single-Family Home
$5,500,000
08/27/26
5
5
3,240
1 Coves End Road, Darien, CT
0.31
Single-Family Home
$6,000,000
04/22/26
6
5
4,807
5 Wilson Avenue, Norwalk, CT
0.34
Single-Family Home
$3,600,000
09/01/26
5
4.5
4,619
98 Rowayton Avenue, Norwalk, CT
0.21
Single-Family Home
$3,715,000
11/03/25
5
4.5
3,581
9 Milton Place, Norwalk, CT
0.42
Single-Family Home
$3,200,000
11/04/25
5
4.5
5,442
74 Roton Avenue, Norwalk, CT
0.41
Single-Family Home
$3,495,000
12/15/25
5
4
4,946
3 Bittersweet Trail, Norwalk, CT
0.59
Single-Family Home
$3,200,000
06/01/26
4
4
4,254
13 Pond Street, Norwalk, CT
0.31
Single-Family Home
$3,475,000
05/14/26
4
3.5
3,188

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
90 Five Mile River Road, Darien, CT 06820
0.12
$4,250,000
5
4.5
5,060
Recently Sold
13 Searles Road, Darien, CT 06820
0.18
$4,918,300
5
5
4,890
Off Market
128 Five Mile River Road, Darien, CT 06820
0.17
$3,464,000
5
3.5
2,478
Recently Sold
111 Rowayton Avenue #302, Norwalk, CT 06853
0.17
$4,438,100
3
3
2,281
Off Market
111 Rowayton Avenue #201, Norwalk, CT 06853
0.17
$4,000,000
3
3
2,399
Recently Sold
98 Rowayton Avenue, Norwalk, CT 06853
0.21
$3,982,100
5
4.5
3,581
Off Market
1 McKinley Street, Norwalk, CT 06853
0.22
$2,988,000
2
3
2,044
Recently Sold
40 Old Farm Road, Darien, CT 06820
0.27
$7,013,000
5
6.5
6,474
Off Market
90 Rowayton Woods Drive #90, Norwalk, CT 06854
0.22
$481,800
1
1
751
Off Market
143 Rowayton Avenue #C, Norwalk, CT 06853
0.23
$5,053,300
4
4.5
3,436
Off Market
143 Rowayton Avenue #B, Norwalk, CT 06853
0.23
$4,530,900
3
2.5
2,307
Off Market
143 Rowayton Avenue #D, Norwalk, CT 06853
0.23
$7,331,500
4
4.5
3,777
Off Market

Local Information

  • Map ViewExplore the area around 104 Five Mile River Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1900
0.72 acre lot
4,945 sqft
$1,201/sqft
Garage

About this House

Originally built in 1900, this home has truly retained a sense of Five Mile River history while offering all the amenities desired by today's buyers. 5 BD & 5 BA, with guest suite on lower level with sweeping water views. Master bedroom features a jet tub, large walk-in closet & porch overlooking Five Mile River. Enjoy open concept living area, dining room & the chef's kitchen featuring fireplace, marble counters, stainless steel appliances & wine fridge, large gym, office with built-ins, & two car garage. Estate-like grounds feature spectacular views of the waterfront, beautiful infinity pool & spa, large outdoor stone fireplace, rose gardens & large screened in porch ideal for summer meals. Priced to sell, this won't last long! This listing is on two lots - the home lot is not in a flood zone; the waterfront lot is in a flood zone.
104 Five Mile River Rd, Darien, CT 06820 is a 5 bedroom, 5 bathroom, 4,945 sqft single-family home in Tokeneke, built in 1900. It last sold for $3,550,000 on Nov 14, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $5,936,800.

Home Details for 104 Five Mile River Rd

Interior Features

Interior Details
BasementNumber of Rooms: 10
Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1900Year Updated: 2007
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Exterior Features

Exterior Home Features
Exterior: Wood
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 0.72 acres

Price and Tax history

DateEventPrice
Nov 14, 2016
Source: Smart MLS #99152107
Sold
$3,550,000
Sep 28, 2016
Source: Agent Provided
PriceChange
$3,595,000
Price decreased by 10%
Sep 1, 2016
Source: Agent Provided
PriceChange
$3,995,000
Price decreased by 11%
Jul 15, 2016
Source: Agent Provided
Listed For Sale
$4,490,000
Mar 30, 2007
Source: Smart MLS #98315036
Sold
$3,300,000

Market trends in Darien

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.82M
$155KMoM
Sale-to-List Price
110.3%
1.4%MoM
Price per sq ft
$821
$21MoM
Available listings
29
7MoM

Around this home

Neighborhood Overview

Tokeneke
See Local Highlights
Neighborhood stats provided by third party data sources.

LGBTQ Local Legal Protections

Frequently asked questions about 104 Five Mile River Rd

  • What is 104 Five Mile River Rd estimated to be worth?
    Trulia's estimated value for 104 Five Mile River Rd in Darien, CT is $5,936,800.
  • What is the price history for 104 Five Mile River Rd?
    104 Five Mile River Rd in Darien, CT last sold for $3,550,000 in November 2016.
  • Is Darien a buyer's or seller's market?
    Darien is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Darien?
    The median sale price in Darien is $2.82M. That is down $155K from the prior month.
  • Does 104 Five Mile River Rd have a pool?
    Yes, 104 Five Mile River Rd in Darien, CT has a pool.
  • How big is the lot at 104 Five Mile River Rd?
    The lot at 104 Five Mile River Rd in Darien, CT is about 0.79 acres (34,412 sq ft).

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