28 Flying Cloud Rd, Stamford, CT 06902
OFF MARKET

28 Flying Cloud Rd
Stamford, CT 06902

Waterside
  • 3 Beds
  • 4.5 Baths
  • 3,628 sqft

$3,393,200

Trulia Estimate
as of Jun 24, 2026
Est. Refi. Payment $21,869/mo*
Refinance Your Home

$3,393,200

Trulia Estimate
as of Jun 24, 2026
Est. Refi. Payment $21,869/mo*
Refinance Your Home
3 Beds
4.5 Baths
3,628 sqft

Local Information

  • Map ViewExplore the area around 28 Flying Cloud Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Serenity and luxury await in this custom-built home with dramatic open water views in the coveted Dolphin Cove Community. Built to current FEMA requirements, the quality of this home shines from the moment you step through the door into the 2-story foyer with wall to wall windows framing a sparkling sunset over LI Sound. Dazzle your guests with seamless indoor/outdoor entertaining space and a private dock for evening sails or an afternoon water skiing on the Sound. Your new community offers activities for young and old, from swimming and tennis to launching a kayak from the private beach or mingling with friends over cocktails at a monthly club social. A brand-new lifestyle awaits just over the Old Greenwich border, minutes from the Stamford or Old Greenwich trains and town. 45 minutes from NYC.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 28 Flying Cloud Rd

Interior Features

Interior Details
BasementNumber of Rooms: 9Types of Rooms: Laundry Room
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Cement ConcretePatio
Parking & Garage
GarageParking: Garage Attached

Property Information

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

Community

Units in Building: 1

Lot Information

Lot Area: 9147 sqft

Additional Information

On Site Laundry Available

Price History for 28 Flying Cloud Rd

DatePriceEventSource
04/15/2020$2,300,000Sold
Smart MLS #170192729
11/12/2019$2,399,000ListingRemovedAgent Provided
10/28/2019$2,399,000PendingAgent Provided
09/11/2019$2,399,000PriceChange
Agent Provided
05/10/2019$2,500,000Listed For SaleAgent Provided

Market trends in Stamford

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$609K
$3.33KMoM
Sale-to-List Price
101.6%
0.1%MoM
Price per sq ft
$394
$4MoM
Available listings
300
62MoM
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Property Tax and Assessment

Year2025
Tax$41,691
Assessment$1,737,110
Home facts updated by county records

Comparable Sales for 28 Flying Cloud Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
158 Davenport Drive, Stamford, CT
0.36
Single-Family Home
$4,050,000
08/22/25
4
5
4,220
9 Davenport Dr, Stamford, CT
0.35
Single-Family Home
$2,550,000
06/23/26
6
5.5
5,450
36 Shore Rd, Old Greenwich, CT
0.34
Single-Family Home
$4,350,000
07/03/25
4
3
3,529
10 Clark St, Old Greenwich, CT
0.73
Single-Family Home
$2,950,000
07/15/25
5
4.5
3,549
121 Dolphin Cove Quay, Stamford, CT
0.12
Single-Family Home
$250,000
06/04/26
3
2.5
2,351
30 Dee Lane, Stamford, CT
0.44
Single-Family Home
$986,000
05/15/26
5
2.5
2,444
3 Davenport Dr, Stamford, CT
0.35
Single-Family Home
$1,125,000
12/03/25
4
3
1,973
36 Highview Ave, Old Greenwich, CT
0.76
Single-Family Home
$3,750,000
08/15/25
4
3.5
3,343
62 Park Ave, Old Greenwich, CT
0.78
Single-Family Home
$3,600,000
05/29/26
4
4.5
3,261
18 Grant Ave, Old Greenwich, CT
0.70
Single-Family Home
$4,150,000
10/03/25
4
4.5
3,491

Nearby homes

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Assigned Schools

These are the assigned schools for 28 Flying Cloud Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

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

What Locals Say about Waterside

At least 54 Trulia users voted on each feature.

  • 77 % Say there are sidewalks

  • 75 % Say it's dog friendly

  • 69 % Say streets are well-lit

  • 68 % Say kids play outside

  • 67 % 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

  • 57 % Say they plan to stay for at least 5 years

  • 55 % 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

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Homes for sale near 28 Flying Cloud Rd

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Off Market Homes Near 28 Flying Cloud Rd

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28 Flying Cloud Rd, Stamford, CT 06902 is a 3 bedroom, 5 bathroom, 3,628 sqft single-family home built in 2003. 28 Flying Cloud Rd is located in Waterside, Stamford. This property is not currently available for sale. 28 Flying Cloud Rd was last sold on Apr 15, 2020 for $2,300,000. The current Trulia Estimate for 28 Flying Cloud Rd is $3,393,200.