For sale

$699,900

Est. $4,728/mo —

•

2,345

sq ft

10 Old Waterbury Rd, Middlebury, CT 06762

About this home

Middlebury Multi-Family-RARE FIND! 4 units! Two buildings on one (.41 acre) parcel. Situated on "park like" grounds at end of cul-de-sac with IN GROUND SWIMMING POOL, and two car detached garage. Commuter friendly with easy access to Rt 8 & I-84, and only moments away to Post University and NVCC. 1st building consists of a side by side TRI-PLEX w/garage under and fireplaced L/R's. 2nd building consists of an adorable, detached single-family RANCH STYLE house-3 rooms/1 bedroom w/oversize fireplace living room & oil heat. Separate heat and utilities. Public water & sewer. Enjoy Middlebury's Greenway trails, hop brook lake for swimming, picnicking, hiking, biking and so much more-all within walking distance! The SUBURBAN town of MIDDLEBURY, is HIGHLY SOUGHT AFTER, rated on TOP, for it's schools and LOW, LOW RENTAL VACANCY. Perfect opportunity for OWNER OCCUPANT to live in one unit and collect rent from other 3 units to help pay mortgage! INVESTORS...be proud to add this one to your portfolio!. Start growing "SWEET EQUITY" with this NATURE LOVERS retreat. PLEASE REFER TO AGENT COMMENTS!

Multi-familyProperty Type

1930Year Built

0.41 acresLot Size

$298Price/Sq.Ft.

3 car garageParking

Listed by Judith Caputo • Advantage Realty Group, Inc.

Contact: Agent Attribution Contact: (203) 755-4015 | Office Attribution Contact: (203) 755-4015

Source:Smart MLS #24207437

Payment calculator

$4,728 per month

Principal and interest$3,820

Property taxes

$640

HOA dues

Home insurance

$268

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN TODAY, 5PM TO 7PM
$359,900
2 beds1 bath1,102 sq ft
224 Lopus Rd, Beacon Falls, CT 06403
OPEN SAT, 10AM TO 12PM
$384,900
3 beds1 bath1,008 sq ft
374 Moss Farms Rd, Cheshire, CT 06410
OPEN SAT, 11AM TO 1PM
$599,900
7 beds5 baths3,560 sq ft
81 Old Coach Hwy, Hamden, CT 06518
REDFIN OPEN SAT, 11:30AM TO 1:30PM3D WALKTHROUGH
$420,000
4 beds1.5 baths1,590 sq ft
34 Pilgrim Trl, Woodbury, CT 06798
OPEN SAT, 12PM TO 2PM
$299,900
3 beds1 bath1,264 sq ft
149 Lakeside Blvd E, Waterbury, CT 06708
OPEN SAT, 12PM TO 2PM
$415,000
3 beds2 baths1,812 sq ft
136 Babbitt Rd, Thomaston, CT 06787
OPEN SAT, 1PM TO 3PM
$359,000
3 beds2 baths1,522 sq ft
27 Seminole Ave, Waterbury, CT 06705
OPEN SUN, 12PM TO 2PM
$365,000
3 beds2 baths1,238 sq ft
368 Hamilton Ave, Watertown, CT 06795
OPEN SUN, 12PM TO 2PM
$299,900
3 beds1.5 baths1,228 sq ft
246 E Waterbury Rd, Naugatuck, CT 06770
OPEN SUN, 12PM TO 2PM
$449,900
3 beds2.5 baths2,647 sq ft
62 Hampton Rd, Waterbury, CT 06708

Around this home

Schools

K - 12
Preschool & daycare

Middlebury Elementary School

Public PreK-5 • Assigned • 1.1mi

5/10

Memorial Middle School

Public 6-8 • Assigned • 0.3mi

8/10

Pomperaug Regional High School

Public 9-12 • Assigned • 4.6mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

10 Old Waterbury Rd · $699,900

Strong offer

$741K and above

75% chance or better to win

Why $741K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 41 days.

SALE-TO-LIST

Most homes are selling 2% above list price.

About offer insights

Property details

Interior
Exterior
Finance

Interior features
13 total rooms
Partial basement
3 fireplaces

Bedrooms
5 bedrooms

Bathrooms
4 full bathrooms

Heating & cooling
Baseboard heating
Heat fuel: Electric and Oil
Hot water: Other

Sale and tax history for 10 Old Waterbury Rd

Sale History
Tax History

Date

Event

Price

Smart MLS #24207437

Sep 15, 2026

Listed

$699,900

$298/sq ft

Smart MLS #24143678

Jun 1, 2026

Listing Removed

—

Feb 18, 2026

Price Changed

$599,900

$256/sq ft

Dec 5, 2025

Listed

$699,900

$298/sq ft

Smart MLS #170538468

Jan 31, 2023

Listing Removed

—

Nov 29, 2022

Listed

$499,900

$213/sq ft

Smart MLS #170449626

Dec 31, 2021

Listing Removed

—

Nov 2, 2021

Listed

$679,900

$290/sq ft

Public Records

Jan 29, 1993

Sold

$90,000

$38/sq ft

Public Records

Apr 4, 1988

Sold

$180,000

$77/sq ft

Year

Property tax

Land + Additions

Assessment*

2022

$7,377 (+11.7%)

$52,700 + $183,300

$236,000

2021

$6,607 (−0.8%)

$60,300 + $129,400

$189,700

2020

$6,658 (+5.1%)

$60,300 + $129,400

$189,700

2019

$6,336 (+2.7%)

$60,300 + $129,400

$189,700

2018

$6,167 (+3.2%)

$60,300 + $129,400

$189,700

2017

$5,974 (−1.0%)

$60,300 + $129,400

$189,700

2016

$6,035 (+5.7%)

$70,500 + $124,100

$194,600

2014

$5,710 (+1.7%)

$70,500 + $124,100

$194,600

2011

$5,616

$70,500 + $124,100

$194,600

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

0.41 Acres

Year renovated

—

Finished Sq. Ft.

—

Unfinished Sq. Ft.

—

Total Sq. Ft.

—

Year built

—

Style

Other

County

New Haven County

APN

1194297

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 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

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

Middlebury, CT • 06762

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Redfin Estimate for 10 Old Waterbury Rd

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

Nearby homes have recently sold between $375,000 and $510,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $375K to $510K.

SOLD JUL 2, 2026
$480,000 Last sold price
3 beds2.5 baths1,734 sq ft
298 Chipman St, Waterbury, CT 06708
$21/sq ft
larger lot
32 years newer
SOLD JUN 26, 2026
$510,000 Last sold price
2 beds2 baths1,962 sq ft
80 Anawan Ave, Middlebury, CT 06762
$38/sq ft
larger lot
22 years newer
SOLD JUL 9, 2026
$380,000 Last sold price
3 beds1 bath1,608 sq ft
55 Highwood Rd, Waterbury, CT 06708
$62/sq ft
larger lot
SOLD AUG 26, 2026
$439,000 Last sold price
3 beds2.5 baths2,194 sq ft
53 Hampton Rd, Waterbury, CT 06708
$98/sq ft
smaller lot
79 years newer
SOLD AUG 4, 2026
$375,000 Last sold price
4 beds2.5 baths2,766 sq ft
319 Maybrook Rd, Waterbury, CT 06708
$162/sq ft
larger lot
43 years newer
SOLD NOV 17, 2025
$380,000 Last sold price
2 beds1.5 baths1,499 sq ft
146 Richardson Dr, Middlebury, CT 06762
$44/sq ft
smaller lot
10 years newer

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Early Access listings

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

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

Mortgage resources

See this home in person

Nearby open houses (10)

Around this home

Schools

Lifestyle

Offer insights

Property details

Sale and tax history for 10 Old Waterbury Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 10 Old Waterbury Rd

Early Access listings

Nearby similar homes

New listings for sale in 06762

More real estate resources