For sale

$349,900

Est. $2,593/mo —

•

1,388

sq ft

409 Highland Dr, Waterbury, CT 06708

About this home

Cherished by its original owner and meticulously maintained throughout the years, this special home is ready for its next chapter-and its next lucky owner! Offering timeless charm, comfortable living spaces, and incredible potential, this is an opportunity you won't want to miss. The classic brick exterior sets the tone, while beautiful hardwood flooring and an inviting open-concept living, dining, and kitchen area create a warm, welcoming atmosphere. Outside, the beautiful, level yard and covered patio provide the perfect setting for summer gatherings, outdoor dining, or simply unwinding at the end of the day. Looking for room to grow and make a home your own? The full, unfinished basement offers a blank canvas brimming with possibilities, whether you envision a recreation room, home gym, hobby space, or in-law apt. An added half bath in the basement is a valuable bonus! A two-car garage and extra-wide driveway offer plenty of parking for you and your guests. This home is a special opportunity for buyers looking for lasting value and room to make their mark. Don't let this one pass you by-schedule your private showing today and discover all the possibilities waiting for you!

Single-familyProperty Type

1963Year Built

0.33 acresLot Size

$252Price/Sq.Ft.

2 car garageParking

Listed by Lynn LaForme • Regency Real Estate, LLC

Contact: Agent Attribution Contact: (203) 910-8618 | Office Attribution Contact: (860) 945-9868

Source:Smart MLS #24216270

Payment calculator

$2,593 per month

Principal and interest$1,910

Property taxes

$564

HOA dues

Home insurance

$120

Utilities

Add

5 minutes to get started. No credit impact.

Affordability tools

See this home in person

We'll connect you with a local agent to show you this home, answer your questions, and assist you on your buying journey.

Next available tour time: Today

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN THU, 5PM TO 7PM3D WALKTHROUGH
$615,000
3 beds2.5 baths2,128 sq ft
70 Eastwood Hall Rd, Watertown, CT 06795
0.66 acre lot • 2 garage spots • Pool
OPEN FRI, 3PM TO 6PM
$274,990
2 beds2 baths1,684 sq ft
198 Straitsville Rd, Prospect, CT 06712
1.36 acre lot • Garage • Pool
OPEN SAT, 10AM TO 4PM
$395,000
2 beds1 bath1,350 sq ft
40 Berkshire Rd, Southbury, CT 06488
3,049 sq ft lot • Parking • Built 1950
OPEN SAT, 11AM TO 1PM
$585,000
3 beds2.5 baths2,363 sq ft
45 Beleden Gardens Dr, Bristol, CT 06010
0.35 acre lot • 2 garage spots • Built 2025
OPEN SAT, 12PM TO 2PM
$675,000
4 beds2.5 baths2,256 sq ft
35 Brookside Pl, Cheshire, CT 06410
0.92 acre lot • 3 garage spots • Built 1985
OPEN SAT, 1PM TO 3PM3D WALKTHROUGH
$309,900
3 beds1 bath1,470 sq ft
48 Rockdale Ave, Oakville, CT 06779
0.3 acre lot • 2 parking spots • Built 1900
OPEN SUN, 11AM TO 1PM
$325,000
4 beds3 baths1,731 sq ft
86 Sycamore St, Bristol, CT 06010
0.23 acre lot • 2 garage spots • Built 1950
OPEN SUN, 1PM TO 3PM
$325,000
2 beds2 baths1,432 sq ft
198 Heritage Vlg Unit B, Southbury, CT 06488
$783 HOA • Garage • Pool
OPEN SUN, 1PM TO 3PM
$360,000
3 beds1.5 baths2,208 sq ft
50 Deering Ln, Waterbury, CT 06706
8,276 sq ft lot • 3 parking spots • Pool
OPEN SUN, 1PM TO 3PM
$344,900
3 beds1.5 baths1,129 sq ft
30 Old Wolcott Rd, Bristol, CT 06010
0.58 acre lot • Built 1915 • Listed 10 days

Around this home

Schools

K - 12
Preschool & daycare

B. W. Tinker School

Public PreK-5 • Assigned • 0.7mi

4/10

West Side Middle School

Public 6-8 • Assigned • 0.5mi

3/10

John F. Kennedy High School

Public 9-12 • Assigned • 0.7mi

1/10

Provided by GreatSchools

About Town

Plot

Town Plot, located between Highland Avenue and Watertown Avenue, is a residential and commercial Waterbury neighborhood with hillside streets and a strong Italian-American imprint. The neighborhood’s character concentrates around the Watertown Avenue corridor near Highland Avenue, where corner bakeries, old-school delis, and long-running eateries set a steady, lived-in rhythm. Brick multifamilies and tidy single-family homes mix with small storefront strips and pocket churches on the slopes. Community pillars include La Tavola Ristorante, Domenic & Pia Downtown Deli, and the Palace Theater for nights out beyond the hill. Fulton Park and nearby trails add green breaks from the dense street grid. Routes toward Downtown and the Naugatuck River valley shape daily movement without changing the neighborhood’s grounded feel.

Provided by Walk Score and Local Logic

Offer insights

409 Highland Dr · $349,900

Strong offer

$372K and above

75% chance or better to win

Why $372K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 45 days.

SALE-TO-LIST

Most homes are selling 2% above list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Open floor plan
One fireplace
Attic with hatch access
Full basement with walk-out, garage access, interior access, and concrete floor

Bedrooms
3 bedrooms

Bathrooms
1 full bathroom
2 half bathrooms

Kitchen
Oven/range
Microwave
Refrigerator
Dishwasher

Laundry & utility
Washer
Dryer
Laundry room on the lower level

Heating & cooling
Hot water heating fueled by oil
Central air

Sale and tax history for 409 Highland Dr

Sale History
Tax History

Public record

Public record
Zoning

Beds

Baths

1.5

Stories

Lot width

—

Lot depth

—

Lot size

0.33 Acres

Year renovated

1985

Finished Sq. Ft.

1,388

Unfinished Sq. Ft.

—

Total Sq. Ft.

1,388

Year built

1963

Style

Single Family Residential

County

New Haven County

APN

1392572

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Low Density Residential District

The RL District is established to provide for single family dwellings and limited nonresidential uses on lots having a minimum area of 6,000 sq ft. Uses and Conditional Accessory Uses are permitted by Zoning Permit, Special Permit, or Special Exception approval as provided in Article 11of these Regulations.

Permitted uses

Include but are not limited to:

No uses permitted by right

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

4/10 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

3/10 Air Factor

2 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Waterbury, CT • 06708

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

91/ 100

Exceptional sunlight

Sunscore

This home ranks in the top 20% for direct sun exposure in Waterbury. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.8 hrs

6 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 409 Highland Dr

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

Nearby homes have recently sold between $335,000 and $380,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $335K to $380K.

SOLD AUG 19, 2026
$335,000 Last sold price
3 beds2.5 baths1,355 sq ft
585 Congress Ave, Waterbury, CT 06708
$5/sq ft
smaller lot
39 years newer
SOLD FEB 4, 2026
$358,600 Last sold price
3 beds1.5 baths1,500 sq ft
87 Highland Dr, Waterbury, CT 06708
$13/sq ft
smaller lot
4 years older
SOLD AUG 3, 2026
$351,600 Last sold price
3 beds1.5 baths1,368 sq ft
91 Mount Carmel Ave, Waterbury, CT 06708
$5/sq ft
smaller lot
6 years older
SOLD APR 17, 2026
$359,900 Last sold price
3 beds1.5 baths1,236 sq ft
78 Carriage Dr, Waterbury, CT 06708
$39/sq ft
smaller lot
15 years newer
SOLD AUG 14, 2026
$336,000 Last sold price
3 beds1.5 baths1,440 sq ft
17 Hickory Hill Dr, Waterbury, CT 06708
$19/sq ft
smaller lot
2 years older
SOLD MAY 22, 2026
$380,000 Last sold price
3 beds2 baths1,200 sq ft
25 Greenview Dr, Waterbury, CT 06708
$65/sq ft
smaller lot
9 years newer

Tour for free, no strings attached

Instant answers, or connect with a local agent

Start an offer

Early Access listings

EARLY ACCESSREDFIN COMING SOON

$525,000

4 beds2.5 baths2,300 sq ft

1 Longview Dr, East Granby, CT 06026

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

$379,900

2 beds2 baths1,864 sq ft

155 Dockerel Rd, Vernon, CT 06066

Nearby similar homes

$269,000

2 beds1 bath1,078 sq ft

46 Windsor St, Waterbury, CT 06708

Eat-in kitchen • Covered front porch • Enclosed sunroom

$299,900

3 beds2 baths1,674 sq ft

101 Birchwood St, Waterbury, CT 06708

L-shaped ranch • Formal dining room • Eat-in kitchen

$399,900

4 beds2.5 baths2,244 sq ft

128 Midwood Ave, Waterbury, CT 06708

Hardwood floors • Dual brick fireplace • Spacious kitchen

$318,000

2 beds1 bath1,376 sq ft

117 Arden Rd, Waterbury, CT 06708

Finished basement • Separate dining room • Solar panel system

$399,900

6 beds3 baths1,528 sq ft

52 Alder St, Waterbury, CT 06708

In law apartment • Newer kitchen • Updated flooring

$399,900

3 beds2.5 baths2,647 sq ft

62 Hampton Rd, Waterbury, CT 06708

Finished basement • Walkout lower level • 5,662 sq ft lot

New listings for sale in 06708

COMING SOON

$374,900

3 beds2.5 baths2,030 sq ft

24 Rockhurst Dr, Waterbury, CT 06708

Newer kitchen • Granite countertops • Butcher block island

$349,900

3 beds2 baths1,388 sq ft

409 Highland Dr, Waterbury, CT 06708

Hardwood flooring • Level yard • Covered patio

OPEN SUN, 4PM TO 6PM

$385,000

3 beds3 baths1,444 sq ft

65 Heritage Dr, Waterbury, CT 06708

Cozy fireplace • Basement • Deck

$169,900

2 beds1.5 baths1,054 sq ft

218 Oakville Ave Unit G, Waterbury, CT 06708

Tri-level townhouse • Extra storage • Great location

$525,000

6 beds4 baths3,650 sq ft

25 Bunker Hill Ave, Waterbury, CT 06708

Electric heat • Gas cooking • 5,227 sq ft lot

$589,000

4 beds2.5 baths2,904 sq ft

50 Shiring Ln, Waterbury, CT 06708

Golf course views • Hard wood flooring • Wooded trim work

$137,900

2 beds1 bath722 sq ft

23 Shirley St #12, Waterbury, CT 06708

Cul de sac • Off street parking • $275 HOA

$259,000

3 beds1.5 baths1,220 sq ft

53 Elk Ave, Waterbury, CT 06708

Remodeled home • Hardwood floors • Central air

$449,900

3 beds2.5 baths1,960 sq ft

39 Regency Hl, Waterbury, CT 06708

Spacious island • Double wall ovens • Ensuite full bath

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

More real estate resources

Neighborhoods
Cities
Zip Codes
Minor Civil Divisions
Popular Searches

Town Plot 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.

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.

06770 homes for sale
06795 homes for sale
06704 homes for sale
06705 homes for sale
06708 homes for sale

Guilford homes for sale
Wallingford homes for sale
Glastonbury homes for sale
Farmington homes for sale
Madison homes for sale

Houses for rent in Waterbury	Agents near me	Westport, CT homes for sale	Waterbury 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	Waterbury Property Records
Condos for sale near me	Norwalk, CT homes for sale	CT New Listings

New Haven homes for sale
West Hartford homes for sale
Milford homes for sale