Off market sep 2021 for $585K

$786,760

Est. refi paymentEst. refi $4,479/mo

•

3,172

sq ft

53 Windy Hill Rd, Milford, CT 06461

About this home

Bring your porch rocker! Beautiful, move-in ready 3 Bedroom 2.5 Bath Center Hall Colonial ideally situated on a quiet cul-de-sac on a quiet tree-lined street. The entertainment friendly floor plan features a spacious Living Room/Dining Room for your largest crowds, a fabulous Great Room encompasses a chef friendly Eat-in Kitchen accented with stainless appliances, granite counter top, and breakfast bar that spills into a sunny main level Family Room with a dramatic cathedral ceiling, a gas fireplace, and plenty of room for the largest of sectionals, also includes sliders to a private deck and large gorgeous green lawn fully fenced yard. Three bedrooms on the upper level includes a King size Master with a spa-inspired full bath with 2 vanities, a free standing tub, pretty tile floor, and separate shower. A nicely finished lower level Game Rm/Media Room has brand new carpet, a built-in bar, game area, and plenty of room for multiple screens, ideal for football Sunday. Hardwood and Crown Molding on the first floor. 2 car garage. Hard wired generator. Central Air, 2 car garage. Hard wired for hybrid vehicles. Close to Metro North New York City train, Milford Green, and beautiful sandy beaches. A stand out gem that won’t last!

Single-familyProperty Type

2006Year Built

0.29 acresLot Size

$248Est. Price/Sq.Ft.

2 car garageParking

Listed by Stephanie Ellison • Keller Williams Realty Prtnrs.

Bought with Sade Tejuoso • TEJ Realty Group

Source:Smart MLS #170418379

Redfin Estimate

$786,760

$202K since sold in September 2021$24K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 20.3% higher than the average sale price ($654K) of 5 comparable homes.

SOLD JUN 30, 2026
$725,000
A
3 beds3 baths2,462 sq ft
20 Twin Oaks Ter, Milford, CT 06460
SOLD FEB 6, 2026
$465,000
B
3 beds2 baths2,464 sq ft
24 Collingsdale Dr, Milford, CT 06461
SOLD MAR 23, 2026
$695,000
C
3 beds3 baths2,288 sq ft
73 Valley View Rd, Milford, CT 06461
SOLD JUL 13, 2026
$830,000
D
4 beds2.5 baths2,834 sq ft
40 Zurko Farm Rd, Milford, CT 06461
SOLD APR 23, 2026
$555,000
E
3 beds2 baths1,596 sq ft
43 Collingsdale Dr, Milford, CT 06461

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$318,515

Est. take-home

List your home with Redfin and save $7,868

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$3,168/mo

Redfin rental estimate

List your home for rent

Market trends in 06461, CT

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

101.3%

0.5% MoM

Median sale price

$517K

$12K MoM

Avg. days on market

38d

2 days MoM

Recently sold homes

3 MoM

New listings for sale

OPEN SUN, 12PM TO 1:30PM
$950,000
4 beds2.5 baths4,022 sq ft
481 Orange Ave, Milford, CT 06461
OPEN SUN, 2PM TO 3:30PM
$385,000
3 beds2 baths1,731 sq ft
63 Camden St, Milford, CT 06461
OPEN SUN, 11AM TO 1PM
$349,000
1 bed1 bath1,313 sq ft
1427 Naugatuck Ave #1427, Milford, CT 06461
$450,000
2 beds2 baths1,645 sq ft
1412 Windward Rd #1412, Milford, CT 06461
OPEN TODAY, 12PM TO 3PM
$699,900
3 beds2.5 baths2,635 sq ft
66 Augusta Dr, Milford, CT 06461
OPEN SUN, 12PM TO 2PM
$925,000
4 beds3 baths2,362 sq ft
139 Wepawaug Dr, Milford, CT 06461
OPEN SUN, 12PM TO 2PM
$499,000
4 beds1 bath1,225 sq ft
4 Windy Hill Rd, Milford, CT 06461
OPEN SUN, 12PM TO 2PM
$789,900
4 beds2.5 baths2,562 sq ft
104 Juniper Dr, Milford, CT 06461
$519,900
3 beds2.5 baths1,960 sq ft
55 W Rutland Rd, Milford, CT 06461
$529,000
4 beds1.5 baths2,016 sq ft
210 North St, Milford, CT 06461
See all

Provided by Redfin

Sale history for 53 Windy Hill Rd

Date

Event

Price

Smart MLS #170418379

Sep 8, 2021

Sold

$585,000

$184/sq ft

Jul 18, 2021

Contingent

—

Jul 9, 2021

Listed

$564,500

$178/sq ft

Smart MLS #170394704

Jul 9, 2021

Listing Removed

—

May 11, 2021

Contingent

—

Apr 30, 2021

Listed

$549,000

$173/sq ft

Public Records

Jun 16, 2020

Sold

$462,000

$146/sq ft

Smart MLS #170290744

Jun 15, 2020

Sold

$452,000

$142/sq ft

May 8, 2020

Contingent

—

Apr 30, 2020

Listed

$449,900

$142/sq ft

Meticulously maintained 3 bed 2.5 bath Colonial. This open and bright home has so much to offer. You will love the updated eat-in kitchen with granite counters, stainless steel appliances, and breakfast bar! The kitchen is open to the family room with a beautiful fireplace and vaulted ceilings. Relax in your large master suite with soaring ceilings a walk-in closet, and completely remodeled master bathroom with Kohler lithocast tub (doesn't get cold to touch), shower spray jets, and heated floors! Private fenced-in yard with a deck with hot tub, patio, storage shed and spacious yard, perfect for entertaining! Other upgrades include 2018 All windows and exterior doors replaced, transferrable lifetime warranty. 2018 In-ground irrigation system New flooring on 2nd level, removed the carpet. Whole-home standby generator (Generac) Hot tub new AC 2019. Propane lines ran for firepit and gas grill. 2 eV charging ports in garage Boost pump to increase water pressure Driveway resealed 2019.

Smart MLS #N335514

Jun 14, 2013

Sold

$420,000

$132/sq ft

Apr 1, 2013

Listed

$449,000

$142/sq ft

Public Records

Mar 20, 2007

Sold

$483,000

$152/sq ft

Smart MLS #98318927

Feb 8, 2007

Listed

$499,900

$158/sq ft

Smart MLS #N258554

Feb 8, 2007

Listed

$499,900

$158/sq ft

Smart MLS #98305805

Feb 9, 2007

Listing Removed

—

Oct 13, 2006

Listed

$499,900

$158/sq ft

Smart MLS #N253813

Feb 6, 2007

Listing Removed

—

Oct 13, 2006

Listed

$499,900

$158/sq ft

Smart MLS #N239588

Jan 6, 2007

Listing Removed

—

Jan 6, 2006

Listed

$499,900

$158/sq ft

Smart MLS #98289942

Dec 6, 2006

Listing Removed

—

Jun 23, 2006

Listed

$519,900

$164/sq ft

Public Records

Aug 8, 2005

Sold

$280,000

$88/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$8,731 (+2.0%)

$87,010 + $234,350

$321,360

2022

$8,564 (+19.3%)

$87,010 + $234,350

$321,360

2021

$7,181 (−0.1%)

$49,000 + $210,720

$259,720

2020

$7,189 (−3.6%)

$49,000 + $210,720

$259,720

2019

$7,454 (+6.7%)

$49,000 + $210,720

$259,720

2018

$6,985 (−0.2%)

$49,000 + $202,810

$251,810

2017

$6,998 (−2.8%)

$49,000 + $202,810

$251,810

2016

$7,201 (+8.8%)

$49,000 + $209,660

$258,660

2013

$6,618

$49,000 + $202,830

$251,830

2011

$6,618

$49,000 + $202,830

$251,830

Tax history for 53 Windy Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$8,731 (+2.0%)

$87,010 + $234,350

$321,360

2022

$8,564 (+19.3%)

$87,010 + $234,350

$321,360

2021

$7,181 (−0.1%)

$49,000 + $210,720

$259,720

2020

$7,189 (−3.6%)

$49,000 + $210,720

$259,720

2019

$7,454 (+6.7%)

$49,000 + $210,720

$259,720

2018

$6,985 (−0.2%)

$49,000 + $202,810

$251,810

2017

$6,998 (−2.8%)

$49,000 + $202,810

$251,810

2016

$7,201 (+8.8%)

$49,000 + $209,660

$258,660

2013

$6,618

$49,000 + $202,830

$251,830

2011

$6,618

$49,000 + $202,830

$251,830

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

0.29 Acres

Year renovated

—

Sq. Ft.

2,272

Year built

2006

Style

Single Family Residential

County

New Haven County

APN

1204304

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Nov 29, 2024.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage
Garages Number: 2

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 6
Interior Features: Auto Garage Door Opener, Cable - Available, Open Floor Plan
Fireplaces Total: 1
Cooling System: Central Air
Appliances Included: Oven/Range, Refrigerator, Dishwasher

Bathroom Information
# of Baths (Full): 2
# of Baths (Half): 1

Bedroom Information
Beds Total: 3

Room Information
Room Count: 8
Basement Description: Full, Full With Hatchway, Partially Finished, Interior Access, Liveable Space, Storage
Has Attic
Attic Description: Access Via Hatch

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Vinyl Siding
Exterior Features: Deck, Patio, Porch, Shed

Lot Information
Lot Description: Level Lot, Fence - Full, Fence - Privacy

Building Information
Foundation Type: Concrete
Construction Description: Frame
Color: Cream

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 2272
Driveway Type: Asphalt

Financial

Assessments Information
Assessed Value: $259,720

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Public Sewer Connected
Hot Water Description: Oil
Heat Type: Hot Air
Heat Fuel Type: Bottle Gas
Fuel Tank Location: Above Ground
Energy Features: Generator Ready, Storm Doors, Thermopane Windows

Location

School Information
Middle Jr High School: West Shore
High School: Jonathan Law
Elementary School: J. F. Kennedy

Location Information
State: Connecticut
Nearby Amenities: Basketball Court, Golf Course, Health Club, Library, Park, Shopping/Mall, Tennis Courts
Directions: West Ave to Innsbruck to Windy Hill; house on left
County: New Haven

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 2,272
Stories: 2.0
Lot Size: 0.29 acres
Style: Single Family Residential
Year Built: 2006
Year Renovated: —
County: New Haven County
APN: 1204304

Home facts updated by county records on Nov 29, 2024

Other

Documents & Disclosures
Supplement Count Public: 3

Around this home

Schools

K - 12
Preschool & daycare

J. F. Kennedy School

Public PreK-5 • Assigned • 0.7mi

8/10

West Shore Middle School

Public 6-8 • Assigned • 1.4mi

7/10

Jonathan Law High School

Public 9-12 • Assigned • 0.8mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

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

6/10 Heat Factor

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

6/10 Wind Factor

58% 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

Milford, CT • 06461

Average low and high temperatures (°F)

36°

21°

38°

23°

52°

34°

61°

43°

69°

52°

80°

61°

84°

68°

81°

61°

76°

58°

65°

47°

55°

38°

40°

26°

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.9 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

8.9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$748,000 – $905,000

Reach more buyers when you sell with Redfin. Save up to $7,868 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

OPEN SUN, 2PM TO 3:30PM

$385,000

3 beds2 baths1,731 sq ft

63 Camden St, Milford, CT 06461

Galley kitchen • New wraparound deck • Newer water heater

$449,900

3 beds2 baths1,465 sq ft

25 Fairfield St, Milford, CT 06460

Quiet street • Inviting living room • Bay window

$459,900

3 beds1 bath1,404 sq ft

63 Golden Hill St, Milford, CT 06460

Historic milford • Updated home • Walkable location

$499,000

4 beds2 baths1,990 sq ft

184 West Ave, Milford, CT 06461

Attached sun room • Eat-in kitchen • Jetted massage tub

$399,900

2 beds1 bath1,980 sq ft

63 Stowe Ave, Milford, CT 06460

Coastal home • Vacation rental • Close to the beach

VIDEO TOUR

$1,925,000

3 beds2.5 baths5,030 sq ft

500 River Rd, Stratford, CT 06614

Spa inspired bath • Designer kitchen • Walk-in pantry

New listings for sale in 06461

OPEN SUN, 12PM TO 1:30PM

$950,000

4 beds2.5 baths4,022 sq ft

481 Orange Ave, Milford, CT 06461

Stone countertops • 0.37 acre lot • Garage

OPEN SUN, 2PM TO 3:30PM

$385,000

3 beds2 baths1,731 sq ft

63 Camden St, Milford, CT 06461

Galley kitchen • New wraparound deck • Newer water heater

OPEN SUN, 11AM TO 1PM

$349,000

1 bed1 bath1,313 sq ft

1427 Naugatuck Ave #1427, Milford, CT 06461

$357 HOA • Garage • Built 1986

$450,000

2 beds2 baths1,645 sq ft

1412 Windward Rd #1412, Milford, CT 06461

Waterfront living • Water views • In ground pool

OPEN TODAY, 12PM TO 3PM

$699,900

3 beds2.5 baths2,635 sq ft

66 Augusta Dr, Milford, CT 06461

Rear deck • Hardwood flooring • 0.41 acre lot

OPEN SUN, 12PM TO 2PM

$925,000

4 beds3 baths2,362 sq ft

139 Wepawaug Dr, Milford, CT 06461

Renovated colonial • Premium appliances • Oversized island

OPEN SUN, 12PM TO 2PM

$499,000

4 beds1 bath1,225 sq ft

4 Windy Hill Rd, Milford, CT 06461

Renovated kitchen • Heated floors • Leased solar panels

OPEN SUN, 12PM TO 2PM3D WALKTHROUGH

$789,900

4 beds2.5 baths2,562 sq ft

104 Juniper Dr, Milford, CT 06461

Covered front porch • Custom kitchen • Granite countertops

$519,900

3 beds2.5 baths1,960 sq ft

55 W Rutland Rd, Milford, CT 06461

Level lot • Deck access • 0.77 acre lot

Home values near 53 Windy Hill Rd

Data from public records.

Address	Redfin Estimate
47 Windy Hill Rd, Milford, CT 4 Beds \| 2.5 Baths \| 2016 Sq. Ft.	$656,016
40 Windy Hill Rd, Milford, CT 3 Beds \| 1 Baths \| 1008 Sq. Ft.	$421,609
60 Windy Hill Rd, Milford, CT 3 Beds \| 2.5 Baths \| 1809 Sq. Ft.	$571,577
65 Windy Hill Rd, Milford, CT 4 Beds \| 2.5 Baths \| 2258 Sq. Ft.	$603,444
45 Thornton St, Milford, CT 4 Beds \| 2.5 Baths \| 2184 Sq. Ft.	$638,433
53 Valley View Rd, Milford, CT 3 Beds \| 1 Baths \| 1118 Sq. Ft.	$453,759
41 Wentworth St, Milford, CT 4 Beds \| 3 Baths \| 2120 Sq. Ft.	$518,053

Address	Redfin Estimate
44 Windy Hill Rd, Milford, CT 3 Beds \| 1 Baths \| 1512 Sq. Ft.	$446,813
70 Windy Hill Rd, Milford, CT 3 Beds \| 1 Baths \| 1104 Sq. Ft.	$472,538
46 Windy Hill Rd, Milford, CT 3 Beds \| 1 Baths \| 1070 Sq. Ft.	$439,399
57 Windy Hill Rd, Milford, CT 3 Beds \| 1.5 Baths \| 1739 Sq. Ft.	$507,407
67 Valley View Rd, Milford, CT 3 Beds \| 1 Baths \| 1380 Sq. Ft.	$495,991
35 Wentworth St, Milford, CT 3 Beds \| 2 Baths \| 1780 Sq. Ft.	$550,103
31 Wentworth St, Milford, CT 3 Beds \| 1 Baths \| 1352 Sq. Ft.	$517,486

Address	Redfin Estimate
34 Windy Hill Rd, Milford, CT 4 Beds \| 2 Baths \| 1588 Sq. Ft.	$547,971
56 Windy Hill Rd, Milford, CT 3 Beds \| 1.5 Baths \| 1701 Sq. Ft.	$511,653
49 Windy Hill Rd, Milford, CT 3 Beds \| 2.5 Baths \| 2292 Sq. Ft.	$670,238
19 Windy Hill Rd, Milford, CT 4 Beds \| 2.5 Baths \| 2748 Sq. Ft.	$635,277
59 Valley View Rd, Milford, CT 3 Beds \| 1 Baths \| 1118 Sq. Ft.	$446,526
57 Innsbruck St, Milford, CT 3 Beds \| 1.5 Baths \| 1200 Sq. Ft.	$489,580
138 West Ave, Milford, CT 3 Beds \| 1 Baths \| 1044 Sq. Ft.	$403,437

Property information provided by Smart MLS when last listed in 2021. This data may not match . Learn more.

More real estate resources

Zip Codes
Minor Civil Divisions
Neighborhoods
Cities
Popular Searches

06614 homes for sale
06477 homes for sale
06460 homes for sale
06461 homes for sale
06484 homes for sale

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

Redfin Brokerage Licenses

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Guilford homes for sale
Wallingford homes for sale
Fairfield homes for sale
Madison homes for sale
Branford homes for sale

Houses for rent in Milford	Agents near me	Westport, CT homes for sale	Milford Housing Market
Houses for sale near me	Greenwich, CT homes for sale	New Haven, CT homes for sale
Land for sale near me	Stamford, CT homes for sale	Milford, CT homes for sale
Open Houses near me	West Hartford, CT homes for sale	Milford Property Records
Condos for sale near me	Norwalk, CT homes for sale	CT New Listings

New Haven homes for sale
Trumbull homes for sale
Westport homes for sale