370 Tucker Hill Rd, Middlebury, CT 06762

Off market sep 2019 for $1M

$2,300,234

•

12,000

sq ft

370 Tucker Hill Rd, Middlebury, CT 06762

About this home

Authentic in every way! Circa 1930's Topsfield is one of Middlebury's grand estates situated on 48+/- acres in the heart of town. Sited at the end of a long private driveway with majestic trees, mature landscaping, an expansive lawn, pastures, and views to the south. Being offered by the original family at a fraction of its replacement value and waiting for the next generation of ownership. Incredible potential to live in the home of ones dreams. Potential conservation easements or subdivision possible as well.

Single-familyProperty Type

1927Year Built

49.5 acresLot Size

$192Est. Price/Sq.Ft.

3 garage spacesParking

Listed by Pels Matthews • William Raveis Real Estate

Listed by Stacey Matthews • William Raveis Real Estate

Bought with Pels Matthews • William Raveis Real Estate

Bought with Stacey Matthews • William Raveis Real Estate

Source:Smart MLS #170141985

Redfin Estimate

$2,300,234

$1.3M since sold in September 2019$156K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 224.5% higher than the average sale price ($709K) of 6 comparable homes.

SOLD SEP 18, 2026
$900,000
A
3 beds2.5 baths4,236 sq ft
625 Charcoal Ave, Middlebury, CT 06762
SOLD AUG 3, 2026
$602,500
B
4 beds2.5 baths3,300 sq ft
321 Artillery Rd, Middlebury, CT 06762
SOLD SEP 14, 2026
$735,000
C
4 beds2.5 baths2,753 sq ft
117 Crest Rd, Middlebury, CT 06762
SOLD DEC 11, 2025
$600,000
D
4 beds4.5 baths4,042 sq ft
1 Umberfield Rd, Waterbury, CT 06708
SOLD MAR 19, 2026
$900,000
E
4 beds4.5 baths5,388 sq ft
77 Eastfield Rd, Waterbury, CT 06708
SOLD AUG 27, 2026
$515,000
F
4 beds2.5 baths2,157 sq ft
880 Whittemore Rd, Middlebury, CT 06762

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Earn from this home

Sell

$1,480,116

Est. take-home

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Rent

$4,363/mo

Redfin rental estimate

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Market trends in 06762, CT

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.5%

0.1% MoM

Median sale price

$575K

$149 MoM

Avg. days on market

48d

1 days MoM

Recently sold homes

5 MoM

New listings for sale

COMING SOON
$479,900
3 beds2 baths2,006 sq ft
961 Middlebury Rd, Middlebury, CT 06762
$485,000
3 beds2 baths1,440 sq ft
314 Porter Ave, Middlebury, CT 06762
$550,000
4 beds2.5 baths1,911 sq ft
802 Charcoal Ave, Middlebury, CT 06762
$650,000
3 beds2.5 baths2,643 sq ft
85 Ridgewood Dr #85, Middlebury, CT 06762
3D WALKTHROUGH
$895,000
3 beds3.5 baths3,024 sq ft
25 Juniper Rd, Middlebury, CT 06762
See all

Provided by Redfin

Sale history for 370 Tucker Hill Rd

Date

Event

Price

Smart MLS #170141985

Sep 12, 2019

Sold

$1,000,000

$83/sq ft

Sep 11, 2019

Listing Removed

—

Aug 1, 2019

Contingent

—

Nov 9, 2018

Listed

$1,495,000

$125/sq ft

Smart MLS #170031882

Nov 3, 2018

Listing Removed

—

Nov 13, 2017

Listed

$1,495,000

$125/sq ft

Smart MLS #L10218581

Aug 11, 2017

Listing Removed

—

May 4, 2017

Listed

$1,500,000

$125/sq ft

Smart MLS #L10050433

Aug 11, 2017

Listing Removed

—

Jun 9, 2015

Listed

$1,900,000

$158/sq ft

Tax history for 370 Tucker Hill Rd

*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

Stories

Lot width

—

Lot depth

—

Lot size

2,156,220

Year renovated

—

Sq. Ft.

12,000

Year built

1927

Style

Single Family Residential

County

New Haven County

APN

1193114

Parking Spaces

Basement

Yes

Accessible

Yes

HOA Dues

—

Garage

Yes

Features

Views, Green

Last updated by owner on Feb 4, 2024.

Property details

Parking

Garage Information
Garage & Parking: Detached Garage
Garages Number: 3

Interior

Interior Information
Total Rooms: 13
Laundry Room Info: Lower Level
Interior Features: Cable - Available, Elevator
Fireplaces Total: 9
Appliances Included: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 6
# of Baths (Half): 2

Bedroom Information
Beds Total: 7

Room Information
Rooms Additional: Foyer, Mud Room
Room Count: 11
Basement Description: Full
Has Attic
Attic Description: Walk-up

Exterior

Exterior Features
Roof Information: Slate
Exterior Siding: Brick, Stucco
Exterior Features: Barn, French Doors, Gutters, Stone Wall, Terrace

Lot Information
Lot Description: May be Subdividable, Some Wetlands, Cleared, Level Lot, Lightly Wooded, Fence - Stone

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

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 7162
Driveway Type: Shared, Paved

Financial

Assessments Information
Assessed Value: $698,030

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Oil
Heat Type: Radiator, Steam
Heat Fuel Type: Oil
Fuel Tank Location: In Basement

Location

School Information
High School: Per Board of Ed
Elementary School: Per Board of Ed

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Lake, Library, Park, Private School(s)
Directions: Rte 64 to Rte 188. Private driveway sign posted for 404 Tucker Hill
County: New Haven

Public facts

Beds: 6
Baths: 7.0
Sq. Ft.: 12,000
Stories: 2.0
Parking Spaces: 10
Basement: Yes
Accessible: Yes
Lot Size: 49.5 acres
Style: Single Family Residential
Year Built: 1927
Year Renovated: —
County: New Haven County
APN: 1193114
HOA Dues: —
Garage: Yes
Features: Views, Green

Home facts updated by owner on Feb 4, 2024

Other

Documents & Disclosures
Supplement Count Public: 7

Around this home

Schools

Middlebury Elementary School

Public PreK-5 • Assigned • 0.7mi

5/10

Memorial Middle School

Public 6-8 • Assigned • 1.3mi

8/10

Pomperaug Regional High School

Public 9-12 • Assigned • 3.2mi

8/10

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

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

In this area, properties receive around 8.8 hours in June and 4.3 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

4.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.19M – $2.65M

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Nearby similar homes

$429,900

4 beds2.5 baths2,244 sq ft

128 Midwood Ave, Waterbury, CT 06708

$389,000

3 beds2 baths1,238 sq ft

152 Saugus Ave, Oakville, CT 06779

3D WALKTHROUGH

$339,000

3 beds2 baths1,506 sq ft

327 Highland Dr, Waterbury, CT 06708

$319,900

2 beds1 bath1,284 sq ft

34 Springdale Ave, Waterbury, CT 06708

$398,900

4 beds2.5 baths2,090 sq ft

232 Lakeside Blvd E, Waterbury, CT 06708

$280,000

2 beds1 bath676 sq ft

327 Steinmann Ave, Middlebury, CT 06762

New listings for sale in 06762

COMING SOON

$479,900

3 beds2 baths2,006 sq ft

961 Middlebury Rd, Middlebury, CT 06762

$485,000

3 beds2 baths1,440 sq ft

314 Porter Ave, Middlebury, CT 06762

$550,000

4 beds2.5 baths1,911 sq ft

802 Charcoal Ave, Middlebury, CT 06762

$650,000

3 beds2.5 baths2,643 sq ft

85 Ridgewood Dr #85, Middlebury, CT 06762

3D WALKTHROUGH

$895,000

3 beds3.5 baths3,024 sq ft

25 Juniper Rd, Middlebury, CT 06762

Home values near 370 Tucker Hill Rd

Data from public records.

Address	Redfin Estimate
335 Tucker Hill Road, Middlebury, CT 4 Beds \| 2.5 Baths \| 3601 Sq. Ft.	$952,684
372 Tucker Hill Road, Middlebury, CT 7 Beds \| 6.5 Baths \| 6600 Sq. Ft.	$995,760

Address	Redfin Estimate
347 Tucker Hill Road, Middlebury, CT 4 Beds \| 4.5 Baths \| 3847 Sq. Ft.	$952,348
231 Tucker Hill Road, Middlebury, CT 2 Beds \| 2 Baths \| 1623 Sq. Ft.	$398,455

Address	Redfin Estimate
193 Tucker Hill Road, Middlebury, CT 2 Beds \| 1 Baths \| 1030 Sq. Ft.	$252,365
404 Tucker Hill Road, Middlebury, CT 4 Beds \| 4.5 Baths \| 4123 Sq. Ft.	$1,272,945

Property information provided by Smart MLS when last listed in 2018. This data may not show owner updates. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06762, CT

Sale history for 370 Tucker Hill Rd

Tax history for 370 Tucker Hill Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06762

Home values near 370 Tucker Hill Rd

More real estate resources