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

39 Flying Cloud Rd
Stamford, CT 06902

Waterside
  • 4 Beds
  • 3.5 Baths
  • 2,384 sqft

$2,063,300

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $13,556/mo*
Refinance Your Home

$2,063,300

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $13,556/mo*
Refinance Your Home
4 Beds
3.5 Baths
2,384 sqft

Local Information

  • Map ViewExplore the area around 39 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
1976
Living Area
2,384 sqft
Price/Sqft
$865
Parking
Garage

About this House

CHARMING NANTUCKET STYLE COLONIAL IN DOLPHIN COVE. Live the vacation lifestyle which is Dolphin Cove- a sought after waterfront community on the Stamford Old Greenwich line. Beautiful and serene water views await you from the moment you step through the doorway. Open concept Living/Dining Room, Country Kitchen open to the family room- the home and all rooms were positioned to access and enjoy the outdoor patio and water amenities. Upstairs the spacious master bedroom has a dressing room/office adjoining a great opportunity to make a Dream Suite. 3 additional bedrooms and 2 full baths complete the 2nd floor. Kayak or just enjoy watching the boats from your backyard or better yet- dock your own boat behind the house at a Dolphin Cove Dock. Enjoy all Dolphin Cove community amenities- pool, tennis, beach, and community activities.
39 Flying Cloud Rd, Stamford, CT 06902 is a 4 bedroom, 4 bathroom, 2,384 sqft single-family home in Waterside, built in 1976. It last sold for $1,125,000 on Dec 31, 2018. It is currently off market. The Trulia Estimate is $2,063,300, with a rent estimate of $5,206/month.

Home Details for 39 Flying Cloud Rd

Interior Features

Interior Details
BasementNumber of Rooms: 10
Heating & Cooling
Heating: Baseboard, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: WoodPatio
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1976Year Updated: 1976
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 8276 sqft

Price History for 39 Flying Cloud Rd

DatePriceEventSource
12/31/2018$1,125,000Sold
Greenwich MLS, Inc. #104745
11/02/2018$1,249,000PriceChange
Agent Provided
10/16/2018$1,274,000PriceChange
Agent Provided
05/31/2018$1,295,000PriceChange
Agent Provided
04/03/2018$1,395,000Listed For SaleAgent Provided
06/25/2004$1,440,000Sold
Smart MLS #98181858
12/16/2002$1,300,000Sold
N/A
11/30/1998$635,000Sold
N/A

Market trends in Stamford

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$630K
$20KMoM
Sale-to-List Price
102.6%
0.9%MoM
Price per sq ft
$398
$4MoM
Available listings
294
6MoM
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Property Tax and Assessment

Year2025
Tax$24,238
Assessment$1,009,910
Home facts updated by county records

Comparable Sales for 39 Flying Cloud Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3 Davenport Dr, Stamford, CT
0.30
Single-Family Home
$1,125,000
12/03/25
4
3
1,973
30 Dee Lane, Stamford, CT
0.42
Single-Family Home
$986,000
05/15/26
5
2.5
2,444
121 Dolphin Cove Quay, Stamford, CT
0.08
Single-Family Home
$250,000
06/04/26
3
2.5
2,351
19 Burwood Avenue, Stamford, CT
0.37
Single-Family Home
$875,000
06/17/26
4
1.5
1,608
18 Cook Road, Stamford, CT
0.27
Single-Family Home
$899,000
07/21/26
2
2
1,864
34 Davenport Drive, Stamford, CT
0.36
Single-Family Home
$1,200,000
06/23/26
3
2
2,268
602 Fairfield Avenue, Stamford, CT
0.39
Single-Family Home
$975,000
12/15/25
4
2
1,600
11 Hendrie Court, Stamford, CT
0.36
Single-Family Home
$500,000
03/30/26
3
1.5
1,690
3 Webb Ave, Old Greenwich, CT
1.10
Single-Family Home
$1,475,000
02/09/26
4
4
2,023
158 Davenport Drive, Stamford, CT
0.31
Single-Family Home
$4,050,000
08/22/25
4
5
4,220

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Assigned Schools

These are the assigned schools for 39 Flying Cloud Rd.
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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 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

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Homes for sale near 39 Flying Cloud Rd

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Off Market Homes Near 39 Flying Cloud Rd

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Frequently asked questions about 39 Flying Cloud Rd

  • What is 39 Flying Cloud Rd estimated to be worth?
    Trulia's estimated value for 39 Flying Cloud Rd in Stamford, CT is $2,063,300.
  • What is the price history for 39 Flying Cloud Rd?
    39 Flying Cloud Rd in Stamford, CT last sold for $1,125,000 in December 2018.
  • 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 $630K. That is up $20K from the prior month.
  • Does 39 Flying Cloud Rd have air conditioning?
    Yes, 39 Flying Cloud Rd in Stamford, CT has air conditioning.
  • Does 39 Flying Cloud Rd have laundry facilities?
    Yes, 39 Flying Cloud Rd in Stamford, CT has in-unit laundry.