22 Flying Cloud Rd, Stamford, CT 06902
Property image
Property image
OFF MARKET

$3,562,300

Trulia Estimate
  • 5 Beds
  • 6.5 Baths
  • 4,337 sqft

22 Flying Cloud Rd, Stamford, CT 06902

Waterside
Est. Refi. Payment $23,293/mo*
Refinance Your Home
Currently Off Market - Sold Oct 3, 2013 for $2,075,000

Home Value

Trulia Estimate
$3.56M
Since last month
Increased$93K (+2.7%)
Since last year
Increased$255K (+7.7%)
Since last sale
Increased$2M (+72.8%)
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 +73% in the last 10 years
MonthEstimated value
2026
August 2026$3.59M
July 2026$3.49M
June 2026$3.53M
May 2026$3.52M
April 2026$3.42M
March 2026$3.48M
February 2026$3.37M
January 2026$3.34M
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
2 Joshua Slocum Dock, Stamford, CT
0.19
Single-Family Home
$2,125,000
08/25/26
3
2.5
2,615
9 Davenport Dr, Stamford, CT
0.35
Single-Family Home
$2,550,000
06/23/26
6
5.5
5,450
2 Sylvan Ln, Old Greenwich, CT
0.54
Single-Family Home
$4,200,000
07/08/26
5
3.5
4,795
30 Dee Lane, Stamford, CT
0.45
Single-Family Home
$986,000
05/15/26
5
2.5
2,444
28 Irvine Rd, Old Greenwich, CT
0.66
Single-Family Home
$4,600,000
05/04/26
5
6
4,538
118 Shore Rd, Old Greenwich, CT
0.69
Single-Family Home
$4,150,000
07/20/26
5
4.5
3,384
30 Park Ave, Old Greenwich, CT
0.84
Single-Family Home
$4,325,000
05/15/26
5
4.5
4,500
57 Lockwood Ave, Old Greenwich, CT
0.60
Single-Family Home
$4,361,000
12/03/25
5
5.5
5,400
3 Davenport Dr, Stamford, CT
0.36
Single-Family Home
$1,125,000
12/03/25
4
3
1,973
60 Benjamin St, Old Greenwich, CT
0.61
Single-Family Home
$7,250,000
07/06/26
6
6
5,941

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
15 Flying Cloud Rd, Stamford, CT 06902
0.03
$3,538,900
6
5.5
4,591
Off Market
46 Signal Rd, Stamford, CT 06902
0.09
$1,750,000
-
-
-
Recently Sold
42 Signal Rd, Stamford, CT 06902
0.09
$1,750,000
-
-
-
Recently Sold
150 Dolphin Cove Quay, Stamford, CT 06902
0.08
$4,332,100
5
4.5
4,138
Off Market
54 Signal Rd, Stamford, CT 06902
0.13
$1,750,000
-
-
-
Recently Sold
199 Dolphin Cove Quay, Stamford, CT 06902
0.12
$4,125,600
3
3.5
4,539
Off Market
106 Dolphin Cove Quay, Stamford, CT 06902
0.14
$1,663,000
4
4
4,424
Off Market
106 Dolphin Cv, Quay Stamford, CT 06902
0.14
$2,074,200
4
4
3,738
Off Market
50 Signal Rd, Stamford, CT 06902
0.16
$1,750,000
-
-
-
Recently Sold
14 Joshua Slocum Dock East, Stamford, CT 06902
0.16
$1,740,100
3
3.5
2,746
Off Market
2 Joshua Slocum Dock, Stamford, CT 06902
0.19
$2,125,000
3
2.5
2,615
Recently Sold
40 Eureka Ter, Stamford, CT 06902
0.21
-
4
2.5
2,623
Off Market

Local Information

  • Map ViewExplore the area around 22 Flying Cloud Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1974
Living Area
4,337 sqft
Price/Sqft
$821
Parking
Garage

About this House

Completely renovated and stunningly re-imagined and decorated 5 bedroom waterfront home with private dock and lap pool. 270 degree views of Long Island sound, Old Greenwich shoreline and Dolphin Cove Club grounds and beaches. Contemporary esthetic makes this dream home and Flying Cloud location so special, it must be seen.
22 Flying Cloud Rd, Stamford, CT 06902 is a 5 bedroom, 7 bathroom, 4,337 sqft single-family home in Waterside, built in 1974. It last sold for $2,075,000 on Oct 3, 2013. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,562,300, with a rent estimate of $6,709/month.

Home Details for 22 Flying Cloud Rd

Interior Features

Interior Details
BasementNumber of Rooms: 9
Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 3
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: WoodPatioPorch
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1974
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 9147 sqft

Price and Tax history

DateEventPrice
Jul 2, 2018
Source: Agent Provided
ListingRemoved
$3,395,000
Apr 3, 2018
Source: Agent Provided
Listed For Sale
$3,395,000
Oct 3, 2013
Source: Greenwich MLS, Inc. #84383
Sold
$2,075,000
Aug 7, 2009
Source: Smart MLS #98422168
Sold
$2,225,000
Nov 18, 1998
Source: N/A
Sold
$1,150,000

Market trends in Stamford

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$679K
$48.83KMoM
Sale-to-List Price
102.7%
0.2%MoM
Price per sq ft
$403
$5MoM
Available listings
287
7MoM

Around this home

Neighborhood Overview

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

What Locals Say about Waterside

At least 55 Trulia users voted on each feature.

  • 77 % Say there are sidewalks

  • 75 % Say it's dog friendly

  • 68 % Say streets are well-lit

  • 68 % Say kids play outside

  • 66 % Say yards are well-kept

  • 63 % Say it's quiet

  • 60 % Say car is needed

  • 60 % Say parking is easy

  • 58 % Say it's walkable to restaurants

  • 58 % Say they plan to stay for at least 5 years

  • 54 % Say people would walk alone at night

  • 54 % Say there's holiday spirit

  • 52 % Say it's walkable to grocery stores

  • 46 % Say neighbors are friendly

  • 44 % Say there's wildlife

  • 27 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Dccjs9x2dy
    "Safe , nice , friendly , good neighbors, good places for enjoy delicious food , nice access to take public transportation , libraries , places for recreation , public schools , beautiful churches."
    0
    Flag
  • Trulia User
    "I Lived Here for 58 years. So use olot of things. I just Need a Change of Scenery, I Enjoy Just Being With My Husband and My 🐕 Just Wanna Enjoy Life."
    0
    Flag
  • Vivian C.
    "easy access to public transportation. walking distance. decent hours. safe locations. train to bus availabilities and vise versa"
    0
    Flag
  • Clive F.
    "It is a very diverse area. Clean and safe. I wouldnt mind living here. Stamford is a growing city. You"
    7
    Flag
  • TG
    "I can walk to the train station. If I drive there is good parking, and there are frequent trains into New York. Also easy to get places thanks to being so close to the I95 freeway."
    0
    Flag
  • Jordan D.
    "One of Stamford's best kept secrets is the Waterside area. This area is just over the Old Greenwich border and has dock access to Long Island Sound, waterfront dining and a great park/beach. Minutes to 2 train stations!"
    8
    Flag
  • Rfriedmanmdceo
    "Private Gated Community- Southfield Point"
    0
    Flag
  • Sally S.
    "The Waterside Community is a true neighborhood. Silver Street is one of the last tree-lined streets in Stamford. Everyone is friendly and truly cares about each other. It's a close-knit community that welcomes diversity. Where else can you own an affordable home, in a safe neighborhood with friendly neighbors so close to the Sound (and not flood during hurriicanes!)? Southfield Beach/Park is a hidden gem. "
    2
    Flag
  • Rfriedmanmdceo
    "Southfield Point is an upscale affluent "gated" private community adjacent to Dolphin Cove and Old Greenwich at the southwestern shoreside tip of Stamford. It is actually closer to Old Greenwich than to downtown Stamford ("
    1
    Flag
  • Sally S.
    "The Waterside area of Stamford has undergone a dramatic transformation over the past decade. Once known for Industry and Low Income Housing Projects, Waterside is now home to the Avalon Stamford Harbor Apartments, Renovated Southfield Park and Beach, 1 mile Waterfront Pier, Tree-Lined Neighborhoods, Multi-Million Dollar Waterfront Homes, Corporate Parks, Lively Waterfront Restaurants, and the new Harbor Point Project. Enjoy a day at the beach, a walk at the Rosa Hartman Park/Woods, a stroll on the Pier, or a delicious meal at any one of many restaurants. Located on the Stamford/Greenwich Border, NYC is only 45 minutes away via Metro-North train or car. "
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 22 Flying Cloud Rd

  • What is 22 Flying Cloud Rd estimated to be worth?
    Trulia's estimated value for 22 Flying Cloud Rd in Stamford, CT is $3,562,300.
  • What is the price history for 22 Flying Cloud Rd?
    22 Flying Cloud Rd in Stamford, CT last sold for $2,075,000 in October 2013.
  • Is Stamford a buyer's or seller's market?
    Stamford is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Stamford?
    The median sale price in Stamford is $679K. That is up $48.83K from the prior month.
  • Does 22 Flying Cloud Rd have a pool?
    Yes, 22 Flying Cloud Rd in Stamford, CT has a pool.
  • How big is the lot at 22 Flying Cloud Rd?
    The lot at 22 Flying Cloud Rd in Stamford, CT is about 0.21 acres (9,147 sq ft).

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