Off market jul 2021 for $440K

$665,827

Est. refi paymentEst. refi $1,532/mo

•

3,273

sq ft

285 Bacon Pond Rd, Woodbury, CT 06798

About this home

The charm of old! Custom Gambrel Cape home with so many extra touches; paneling, built-in bookshelves & corner hutch, beamed ceilings, exposed brick and so much more. Level driveway leaving only a few steps from the attached garage to the eat-in kitchen and on to the first-floor master bedroom. Over 3200 square feet of the living area consisting of formal dining and living rooms, eat-in kitchen, and an additional main level office/bedroom. The upper level includes three more bedrooms with built-ins, a full bath, and a walk-in attic for storage. The home's family room is located in the walkout lower level and offers a bar, gorgeous brick fireplace, and half bath, making it the perfect gathering room for indoor get together's. Centrally located in downtown Woodbury, this home is just a short walk to all the fine restaurants in the Middle Quarter section of Woodbury. Don't miss this charmer as it is tucked just off the road with an attached two-car garage, open front porch, and a huge screened porch with a stone floor set back behind the garage overlooking the property.

Subject to probate court approval

Single-familyProperty Type

1962Year Built

1.09 acresLot Size

$203Est. Price/Sq.Ft.

2 car garageParking

Listed by Timothy Drakeley • Drakeley Real Estate, Inc.

Bought with Cathy Masi • Flagpole Realty Inc

Source:Smart MLS #170377989

Redfin Estimate

$665,827

$226K since sold in July 2021$12K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.4% lower than the average sale price ($711K) of 6 comparable homes.

SOLD AUG 27, 2026
$605,000
A
3 beds3.5 baths2,479 sq ft
30 Park Rd, Woodbury, CT 06798
SOLD SEP 9, 2026
$570,000
B
4 beds2.5 baths2,428 sq ft
148 Colonial Dr, Southbury, CT 06488
SOLD AUG 3, 2026
$635,000
C
4 beds2.5 baths2,157 sq ft
20 Stagecoach Rd, Woodbury, CT 06798
SOLD JUL 31, 2026
$1,275,000
D
4 beds3.5 baths3,480 sq ft
46 Grassy Hill Rd, Woodbury, CT 06798
SOLD AUG 12, 2026
$477,000
E
3 beds2.5 baths1,704 sq ft
38 Mountain Rd, Woodbury, CT 06798
SOLD SEP 29, 2026
$705,000
F
4 beds2.5 baths2,367 sq ft
121 Carriage Dr, Southbury, CT 06488

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Earn from this home

Sell

$309,524

Est. take-home

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Refinance

Est. cash available

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Rent

$3,971/mo

Redfin rental estimate

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Market trends in 06798, CT

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.0%

+0.5% MoM

Median sale price

$500K

$216 MoM

Avg. days on market

60d

6 days MoM

Recently sold homes

16 MoM

New listings for sale

3D WALKTHROUGH
$290,000
2 beds1.5 baths1,430 sq ft
74 Washington Rd #40, Woodbury, CT 06798
$2,149,900
6 beds4.5 baths5,973 sq ft
348 Weekeepeemee Rd, Woodbury, CT 06798
OPEN TODAY, 12PM TO 2PM
$849,900
4 beds2 baths2,662 sq ft
63 Main St N, Woodbury, CT 06798
$550,000
3 beds2.5 baths2,796 sq ft
164 Quanopaug Trl, Woodbury, CT 06798
OPEN TODAY, 10AM TO 12PM
$875,000
3 beds2.5 baths2,480 sq ft
2 Pomperaug Rd, Woodbury, CT 06798
$990,000
6 beds3.5 baths3,842 sq ft
92 Quail Run Rd, Woodbury, CT 06798
$199,900
2 beds1 bath913 sq ft
229 Bacon Pond Rd #312, Woodbury, CT 06798
OPEN TODAY, 12PM TO 2PM
$299,900
2 beds2 baths1,182 sq ft
47 Woods Way #47, Woodbury, CT 06798
$550,000
3 beds2 baths1,550 sq ft
578 Old Sherman Hill Rd, Woodbury, CT 06798
OPEN TODAY, 10AM TO 12PM
$925,000
4 beds2.5 baths2,568 sq ft
69 Nonnewaug Rd, Woodbury, CT 06798
See all

Provided by Redfin

Sale history for 285 Bacon Pond Rd

Year

Property tax

Land + Additions

Assessment*

2023

$7,307 (−0.4%)

$69,990 + $181,440

$251,430

2022

$7,334

$69,990 + $181,440

$251,430

2021

$7,334

$69,990 + $181,440

$251,430

2020

$7,334

$69,990 + $181,440

$251,430

2019

$7,334 (−0.5%)

$69,990 + $181,440

$251,430

2018

$7,374 (−2.1%)

$77,770 + $199,670

$277,440

2017

$7,535 (+3.3%)

$77,770 + $199,670

$277,440

2016

$7,294 (+2.3%)

$77,770 + $199,670

$277,440

2014

$7,127

$77,770 + $199,670

$277,440

Tax history for 285 Bacon Pond Rd

Year

Property tax

Land + Additions

Assessment*

2023

$7,307 (−0.4%)

$69,990 + $181,440

$251,430

2022

$7,334

$69,990 + $181,440

$251,430

2021

$7,334

$69,990 + $181,440

$251,430

2020

$7,334

$69,990 + $181,440

$251,430

2019

$7,334 (−0.5%)

$69,990 + $181,440

$251,430

2018

$7,374 (−2.1%)

$77,770 + $199,670

$277,440

2017

$7,535 (+3.3%)

$77,770 + $199,670

$277,440

2016

$7,294 (+2.3%)

$77,770 + $199,670

$277,440

2014

$7,127

$77,770 + $199,670

$277,440

*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

1.09 Acres

Year renovated

—

Sq. Ft.

2,873

Year built

1962

Style

Single Family Residential

County

Litchfield County

APN

935400

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jun 20, 2023.

Property details

Parking

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

Interior

Interior Information
Total Rooms: 9
Laundry Room Location: Basement
Laundry Room Info: Lower Level
Interior Features: Security System
In-Law Apartment: No
In-Law Access: First Floor
Fireplaces Total: 2
Appliances Included: Electric Range, Refrigerator, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 3
# of Baths (Half): 1

Bedroom Information
Beds Total: 4

Room Information
Rooms Additional: Breezeway, Foyer
Room Count: 9
Basement Description: Full With Walk-Out, Partially Finished
Has Attic
Attic Description: Floored, Storage Space

Exterior

Exterior Features
Roof Information: Wood Shingle
Exterior Siding: Wood
Exterior Features: Breezeway, Porch, Porch-Screened

Lot Information
Lot Description: Cleared, Secluded, Lightly Wooded

Building Information
Foundation Type: Block, Concrete
Construction Description: Frame

Property Information
Waterfront Description: Frontage, Brook
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 2873

Financial

Assessments Information
Assessed Value: $251,430

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Domestic
Heat Type: Baseboard
Heat Fuel Type: Oil
Fuel Tank Location: In Basement
Energy Features: Storm Windows

Location

School Information
Middle Jr High School: Woodbury
High School: Nonnewaug
Elementary School: Mitchell

Location Information
State: Connecticut
Nearby Amenities: Basketball Court, Golf Course, Library, Medical Facilities, Park, Private School(s), Tennis Courts
Directions: 64 to old sherman to bacon pond or 6 to park road, right onto bacon pond
Direct Waterfront
County: Litchfield

Public facts

Beds: 5
Baths: 3.0
Sq. Ft.: 2,873
Stories: 2.0
Lot Size: 1.09 acres
Style: Single Family Residential
Year Built: 1962
Year Renovated: —
County: Litchfield County
APN: 935400

Home facts updated by county records on Jun 20, 2023

Other

Documents & Disclosures
Supplement Count Public: 5

Around this home

Schools

Mitchell Elementary School

Public PreK-5 • Assigned • 1.3mi

5/10

Woodbury Middle School

Public 6-8 • Assigned • 1.4mi

6/10

Nonnewaug High School

Public 9-12 • Assigned • 2.0mi

9/10

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

5/10 Heat Factor

7 days above 96° expected this year, 15 days in 30 years

5/10 Wind Factor

26% chance of strong winds in next 30 years

3/10 Air Factor

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

Provided by First Street

Historical weather

Woodbury, CT • 06798

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 8.7 hours in June and 4.2 hours in December, placing it below the U.S. average for solar exposure.

8.7 hrs

4.2 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$633,000 – $766,000

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New listings for sale in 06798

3D WALKTHROUGH

$290,000

2 beds1.5 baths1,430 sq ft

74 Washington Rd #40, Woodbury, CT 06798

$2,149,900

6 beds4.5 baths5,973 sq ft

348 Weekeepeemee Rd, Woodbury, CT 06798

OPEN TODAY, 12PM TO 2PM

$849,900

4 beds2 baths2,662 sq ft

63 Main St N, Woodbury, CT 06798

$550,000

3 beds2.5 baths2,796 sq ft

164 Quanopaug Trl, Woodbury, CT 06798

OPEN TODAY, 10AM TO 12PM

$875,000

3 beds2.5 baths2,480 sq ft

2 Pomperaug Rd, Woodbury, CT 06798

$990,000

6 beds3.5 baths3,842 sq ft

92 Quail Run Rd, Woodbury, CT 06798

$199,900

2 beds1 bath913 sq ft

229 Bacon Pond Rd #312, Woodbury, CT 06798

OPEN TODAY, 12PM TO 2PM

$299,900

2 beds2 baths1,182 sq ft

47 Woods Way #47, Woodbury, CT 06798

$550,000

3 beds2 baths1,550 sq ft

578 Old Sherman Hill Rd, Woodbury, CT 06798

Home values near 285 Bacon Pond Rd

Data from public records.

Address	Redfin Estimate
237 Bacon Pond Road, Woodbury, CT 3 Beds \| 2 Baths \| 1266 Sq. Ft.	$424,605
249 Bacon Pond Road, Woodbury, CT 4 Beds \| 2.5 Baths \| 2239 Sq. Ft.	$622,865

Address	Redfin Estimate
271 Bacon Pond Road, Woodbury, CT 3 Beds \| 3 Baths \| 3485 Sq. Ft.	$724,798
263 Bacon Pond Road, Woodbury, CT 3 Beds \| 2.5 Baths \| 1664 Sq. Ft.	$521,448

Address	Redfin Estimate
242 Bacon Pond Road, Woodbury, CT 4 Beds \| 1 Baths \| 1836 Sq. Ft.	—
243 Bacon Pond Road, Woodbury, CT 4 Beds \| 2 Baths \| 1692 Sq. Ft.	$470,725

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

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