CONTINGENT

Contingent

$949,900

Est. $6,620/mo —

•

4,844

sq ft

16 Windy Rdg, Trumbull, CT 06611

About this home

Exceptional multi-generational living opportunity in the heart of Trumbull! This expansive 4,844 sq. ft. home is perfect for a big family. The main home features 4 bedrooms, 3 full bathrooms, full dining room, living room and kitchen with hardwood floors throughout. In addition there's an extra 1,100+sqft finished walkout basement. The other side of the home is a private legal ADU Designed for comfort and privacy, townhouse style 2 bedrooms 1.5baths with a full kitchen, living room, laundry a private driveway and balcony. The main home also features a spacious attached two-car garage and private backyard complete with an oversized deck area and an in-ground swimming pool, creating the perfect setting for entertaining and outdoor enjoyment. Offering generous living space and a unique layout, this one-of-a-kind property combines functionality, versatility, and endless possibilities.

Single-familyProperty Type

1947Year Built

0.56 acresLot Size

$196Price/Sq.Ft.

2 garage spacesParking

Listed by Edison Andrade • Coldwell Banker Realty

Contact: Agent Attribution Contact: (203) 703-2225 | Office Attribution Contact: (203) 322-2300

Source:Smart MLS #24187764

Payment calculator

$6,620 per month

Principal and interest$4,992

Property taxes

$1,264

HOA dues

Home insurance

$364

Utilities

Add

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Affordability tools

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN THU, 11AM TO 2PM
$1,799,000
5 beds3.5 baths2,732 sq ft
239 Beach Rd, Fairfield, CT 06824
OPEN THU, 11AM TO 1PM
$1,000,000
3 beds2.5 baths2,291 sq ft
107 Benedict Ave, Fairfield, CT 06825
OPEN SAT, 11AM TO 1PM3D WALKTHROUGH
$649,000
3 beds1.5 baths1,464 sq ft
36 Great Meadow Rd, Milford, CT 06460
OPEN SAT, 12PM TO 4PM
$2,750,000
5 beds6.5 baths6,920 sq ft
27 Walnut Ln, Weston, CT 06883
OPEN SAT, 1PM TO 3PM
$1,500,000
4 beds3.5 baths4,181 sq ft
11 Oak Ridge Dr, Newtown, CT 06470
OPEN SAT, 1PM TO 3PMVIDEO TOUR
$894,900
4 beds2.5 baths3,923 sq ft
32 Pine Tree Hill Rd, Newtown, CT 06470
OPEN SUN, 12PM TO 3PM
$799,900
3 beds3 baths2,103 sq ft
50 Oak Ridge Rd, Stratford, CT 06614
OPEN SUN, 12PM TO 2PM
$479,900
3 beds1.5 baths1,569 sq ft
76 Newton St, Stratford, CT 06614
OPEN SUN, 12PM TO 3PM
$195,000
2 beds1 bath924 sq ft
28 Woodland Park, Shelton, CT 06484
OPEN SEP 7, 12PM TO 2PM
$719,900
4 beds2.5 baths2,256 sq ft
30 Dartmouth Dr, Shelton, CT 06484

Around this home

Schools

K - 12
Preschool & daycare

Frenchtown Elementary

Public K-5 • Assigned • 0.8mi

9/10

Madison Middle School

Public 6-8 • Assigned • 2.3mi

8/10

Trumbull High School

Public 9-12 • Assigned • 1.5mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Auto garage door opener
Two fireplaces
In-law apartment with separate entry
Full heated, partially finished walk-out basement
Attic with walk-up storage space
Ceiling fans and central air

Bedrooms
6 bedrooms

Bathrooms
4 full bathrooms
1 half bathroom

Kitchen
Electric range
Refrigerator

Laundry & utility
Washer and electric dryer
Laundry room on lower level
50-gallon hot water tank

Heating & cooling
Hot air and hot water heating
Heating fuel: oil and solar
Active solar energy features

Sale and tax history for 16 Windy Rdg

Sale History
Tax History

Date

Event

Price

Smart MLS #24187764

Aug 6, 2026

Contingent

—

Jul 16, 2026

Listed

$949,900

$196/sq ft

Avail #1

Oct 21, 2025

Rental Removed

$3,200

$1/sq ft

Sep 10, 2025

Listed for Rent

$3,200

$1/sq ft

Smart MLS #170421814

Oct 8, 2021

Sold

$635,000

$131/sq ft

Aug 4, 2021

Contingent

—

Jul 21, 2021

Listed

$647,900

$134/sq ft

Welcome Home - this is the rare find you have been waiting for! Expanded, spacious, lovingly maintained 6 BD/4.5 BTH Cape/Colonial with legal Inlaw/Accessory townhouse & I/G pool, located in desirable neighborhood in the Heart of Trumbull! Beautifully landscaped level lot & lovely curb appeal greets you to a home w/ gleaming H/W flrs thruout. Main home showcases a formal DR & sunny LR w/ woodburning FPL, builtins, picture window, crown mldg. Remodeled EIK w/ center island, granite counters, newer SS appliances, gas range, marble bksplash, skylight, recessed lts. Just off the kitchen is a heated sunrm w/ vltd ceiling that opens to a large deck overlooking private fenced yard, abundant veggie gardens & sparkling I/G pool w/ newer liner & pump - perfect for outdoor entertaining! Full BTH & 2 large BDS on main lvl, one with a wall of builtins, ideal for a home office! Upper lvl touts a full BTH w/ jettub, a roomy BD w/ builtins & a huge MSTR w/ walkin closet & attic access. Wonderful FR/Home theater w/ full BTH in finished walkout LL + plenty of storage. From the main home, or from the 2nd driveway/separate entrance, enter the 2004 townhome addition which offers gas heat, large kitchen, LR/DR combo & private deck, half BTH & full size washer/dryer on main lvl. Upper lvl has 2 generous BDS, each with huge walkin closets, & a full BTH w/vltd ceiling & pulldown attic. City water/sewer, C/A. Award wining school district! Mile to Merritt/25. Walk to shops/restaurants/trails/parks!

Public Records

Feb 15, 2011

Sold

$506,000

$104/sq ft

Smart MLS #V985721

Oct 4, 2010

Listed

$549,900

$114/sq ft

Join or sign in to view all info

Public record

Beds

Baths

4.5

Stories

Lot width

—

Lot depth

—

Lot size

0.56 Acres

Year renovated

—

Finished Sq. Ft.

3,656

Unfinished Sq. Ft.

—

Total Sq. Ft.

3,656

Year built

1947

Style

Multi-Family (2-4 Unit)

County

Fairfield County

APN

395467

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 12, 2023.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 97° expected this year, 15 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

4/10 Air Factor

5 unhealthy days expected this year, 7 days in 30 years

Provided by First Street

Historical weather

Trumbull, CT • 06611

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

89/ 100

Very good sunlight

Sunscore

This home receives average direct sun exposure in Trumbull. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10.2 hrs

5.8 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 16 Windy Rdg

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $575,000 and $760,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $575K to $760K.

SOLD JUL 30, 2026
$735,000 Last sold price
3 beds2.5 baths1,903 sq ft
162 Killian Ave, Trumbull, CT 06611
$190/sq ft
smaller lot
SOLD JUL 31, 2026
$575,000 Last sold price
3 beds2.5 baths1,938 sq ft
2010 Old Town Rd, Trumbull, CT 06611
$101/sq ft
smaller lot
30 years newer
SOLD JUN 15, 2026
$610,000 Last sold price
4 beds2.5 baths2,716 sq ft
28 Grandview Dr, Trumbull, CT 06611
$29/sq ft
larger lot
16 years newer
SOLD APR 1, 2026
$705,000 Last sold price
4 beds2.5 baths2,096 sq ft
65 Bonnie View Dr, Trumbull, CT 06611
$140/sq ft
larger lot
46 years newer
SOLD JUL 22, 2026
$760,000 Last sold price
5 beds3 baths3,092 sq ft
7 Merrill Rd, Trumbull, CT 06611
$50/sq ft
smaller lot
6 years older
SOLD JUL 8, 2026
$755,000 Last sold price
5 beds3.5 baths2,864 sq ft
75 Parkway Dr, Trumbull, CT 06611
$68/sq ft
smaller lot
7 years older

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(475) 405-2745

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Details provided by Smart MLS and may not match the public record. Learn more.

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