Off market may 2022 for $260K

$466,153

Est. refi paymentEst. refi $1,954/mo

•

994

sq ft

249 Whippoorwill Rd, Old Lyme, CT 06371

About this home

Consider this stunning pastoral retreat for your next renovation project. Dating to the mid-1800s, the home has been lived in year round until recently and the first time publicly offered in decades. Set on 2.25 acres, the farmhouse offers 994 SF to make your own including 3 BRs and a full bath. A garage and workshop are found closest to the home. A large barn/carriage house is set off a bit, flanked by open meadows. The property is bounded partially to the north and west by Champlain South Preserve with 200+ acres and 4+ miles of hiking trails. Located on one of the most scenic Old Lyme country roads, it's just 1.5 miles to the beach, village, schools, marina and country club. Blessed with character and sweet bones, this humble diamond-in-the-rough is looking to her next owner to restore her charm. The perfect space to enjoy hobby farming, gardening, woodworking or studio space. Updates are needed and being sold “as is.” Call for a full packet.

Records indicate 1300-1400 gallon cesspool pumped every five years, town recommended timeframe.

Single-familyProperty Type

1850Year Built

2.25 acresLot Size

$469Est. Price/Sq.Ft.

4 car garageParking

Listed by Nancy Mesham • Coldwell Banker Realty

Bought with Catherine Howard • Berkshire Hathaway NE Prop.

Source:Smart MLS #170468685

Redfin Estimate

$466,153

$206K since sold in May 2022$13K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 31.8% lower than the average sale price ($683K) of 6 comparable homes.

SOLD OCT 29, 2026
$700,000
A
2 beds2 baths1,128 sq ft
3 Neck Rd, Old Lyme, CT 06371
SOLD OCT 15, 2026
$850,000
B
3 beds2.5 baths2,072 sq ft
3 Maple Ln, Old Lyme, CT 06371
SOLD OCT 31, 2026
$1,100,000
C
3 beds2 baths3,113 sq ft
60 Lyme St, Old Lyme, CT 06371
SOLD AUG 2, 2026
$340,000
D
3 beds1 bath1,104 sq ft
6 Blackwell Ln, Old Lyme, CT 06371
SOLD MAY 29, 2026
$510,000
E
3 beds1 bath1,124 sq ft
12 Littlefield Dr, Old Lyme, CT 06371
SOLD JUL 31, 2026
$599,000
F
3 beds1.5 baths1,434 sq ft
118-1 Whippoorwill Rd, Old Lyme, CT 06371

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Earn from this home

Sell

$247,311

Est. take-home

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Refinance

Est. cash available

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Rent

$1,909/mo

Redfin rental estimate

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Market trends in 06371, CT

Last updated October 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-list price

97.9%

0.6% MoM

Median sale price

$715K

$45K MoM

Avg. days on market

38d

18 days MoM

Recently sold homes

8 MoM

New listings for sale

VIDEO TOUR
$535,000
3 beds2 baths1,878 sq ft
55 Rogers Lake Trl, Old Lyme, CT 06371
$399,990
4 beds3 baths2,148 sq ft
60 Town Woods Rd, Old Lyme, CT 06371
$2,195,000
4 beds2.5 baths3,198 sq ft
119 Bill Hill Rd, Lyme, CT 06371
$675,000
4 beds3.5 baths2,506 sq ft
290 Hamburg Rd, Lyme, CT 06371
See all

Provided by Redfin

Sale history for 249 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$4,239

$106,200 + $74,200

$180,400

2022

$4,239 (+0.9%)

$106,200 + $74,200

$180,400

2021

$4,203 (+0.4%)

$106,200 + $74,200

$180,400

2020

$4,185 (+3.4%)

$106,200 + $74,200

$180,400

2019

$4,049 (+2.3%)

$111,800 + $68,900

$180,700

2018

$3,959 (+0.7%)

$111,800 + $68,900

$180,700

2017

$3,930 (+2.6%)

$111,800 + $68,900

$180,700

2016

$3,831 (+3.3%)

$111,800 + $68,900

$180,700

2014

$3,708 (+2.0%)

$111,800 + $76,800

$188,600

2011

$3,634

$111,800 + $76,500

$188,300

Tax history for 249 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$4,239

$106,200 + $74,200

$180,400

2022

$4,239 (+0.9%)

$106,200 + $74,200

$180,400

2021

$4,203 (+0.4%)

$106,200 + $74,200

$180,400

2020

$4,185 (+3.4%)

$106,200 + $74,200

$180,400

2019

$4,049 (+2.3%)

$111,800 + $68,900

$180,700

2018

$3,959 (+0.7%)

$111,800 + $68,900

$180,700

2017

$3,930 (+2.6%)

$111,800 + $68,900

$180,700

2016

$3,831 (+3.3%)

$111,800 + $68,900

$180,700

2014

$3,708 (+2.0%)

$111,800 + $76,800

$188,600

2011

$3,634

$111,800 + $76,500

$188,300

*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

2.25 Acres

Year renovated

—

Sq. Ft.

994

Year built

1850

Style

Single Family Residential

County

New London County

APN

1551383

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 14, 2023.

Property details

Parking

Garage Information
Garage & Parking: Detached Garage, Barn
Garages Number: 4

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 5
Interior Features: Cable - Available

Bathroom Information
# of Baths (Full): 1

Bedroom Information
Beds Total: 3

Room Information
Room Count: 6
Basement Description: Full With Hatchway
Has Attic
Attic Description: Access Via Hatch

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Aluminum
Exterior Features: Barn

Lot Information
Lot Description: Open Lot, Lightly Wooded

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

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 994
Driveway Type: Gravel

Financial

Assessments Information
Assessed Value: $180,400

Utilities

Utility Information
Water Source: Private Well
Sewage System: Cesspool
Hot Water Description: Domestic
Heat Type: Baseboard
Heat Fuel Type: Oil
Fuel Tank Location: In Basement

Location

School Information
Middle Jr High School: Lyme-Old Lyme
High School: Lyme-Old Lyme
Elementary School: Mile Creek

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Library, Medical Facilities, Paddle Tennis, Private Rec Facilities, Public Rec Facilities, Shopping/Mall, Tennis Courts
Directions: 95 North exit 70. Right on Shore Road. Left on Mile Creek. Turn Left on Whippoorwill. First home on the left about a quarter mile down.
County: New London

Public facts

Beds: 3
Baths: 1.0
Sq. Ft.: 994
Stories: 1.0
Lot Size: 2.25 acres
Style: Single Family Residential
Year Built: 1850
Year Renovated: —
County: New London County
APN: 1551383

Home facts updated by county records on Jul 13, 2023

Around this home

Schools

K - 12
Preschool & daycare

Mile Creek School

Public K-5 • Assigned • 1.7mi

9/10

Lyme-Old Lyme Middle School

Public 6-8 • Assigned • 1.1mi

8/10

Lyme-Old Lyme High School

Public 9-12 • Assigned • 0.9mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

10/10 Flood Factor

Estimated 80%+ chance of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 94° expected this year, 17 days in 30 years

8/10 Wind Factor

80% 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

Old Lyme, CT • 06371

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 9.1 hours in June and 4.6 hours in December, which is comparable to the U.S. average for solar exposure.

9.1 hrs

4.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$443,000 – $537,000

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New listings for sale in 06371

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Eat in kitchen • Pantry closets • 0.39 acre lot

$399,990

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Finished lower level • Large yard • Secluded setting

$2,195,000

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14.46 acre lot • 5 garage spots • Built 1973

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Home values near 249 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
268 Whippoorwill Road, Old Lyme, CT 4 Beds \| 1.5 Baths \| 1404 Sq. Ft.	$680,524
240 Whippoorwill Road, Old Lyme, CT 2 Beds \| 1 Baths \| 1828 Sq. Ft.	$733,032
236 Whippoorwill Road, Old Lyme, CT 3 Beds \| 1 Baths \| 1228 Sq. Ft.	$497,020
14 Jadon Drive, Old Lyme, CT 3 Beds \| 3 Baths \| 2576 Sq. Ft.	$737,758
20 Meetinghouse Lane, Old Lyme, CT 3 Beds \| 3 Baths \| 4006 Sq. Ft.	$1,229,582
74 Mile Creek Road, Old Lyme, CT 4 Beds \| 2.5 Baths \| 4576 Sq. Ft.	$1,164,164
9 Jadon Drive, Old Lyme, CT - Beds \| 0.5 Baths \| 1800 Sq. Ft.	$299,993

Address	Redfin Estimate
260 Whippoorwill Road, Old Lyme, CT 5 Beds \| 3 Baths \| 2077 Sq. Ft.	$680,157
234 Whippoorwill Road, Old Lyme, CT 3 Beds \| 2.5 Baths \| 2171 Sq. Ft.	$714,456
232 Whippoorwill Road, Old Lyme, CT 4 Beds \| 2 Baths \| 1584 Sq. Ft.	$525,145
8 Jadon Drive, Old Lyme, CT 3 Beds \| 1.5 Baths \| 1363 Sq. Ft.	$616,969
3 Jadon Drive, Old Lyme, CT 2 Beds \| 1 Baths \| 832 Sq. Ft.	$377,549
70 Mile Creek Road, Old Lyme, CT 2 Beds \| 1 Baths \| 811 Sq. Ft.	$378,077
15 Jadon Drive, Old Lyme, CT 3 Beds \| 2.5 Baths \| 2058 Sq. Ft.	$724,176

Address	Redfin Estimate
262 Whippoorwill Road, Old Lyme, CT 4 Beds \| 2.5 Baths \| 2674 Sq. Ft.	$907,851
252 Whippoorwill Road, Old Lyme, CT 3 Beds \| 1 Baths \| 1469 Sq. Ft.	$505,660
254 Whippoorwill Road, Old Lyme, CT 3 Beds \| 3 Baths \| 2714 Sq. Ft.	$962,055
4 Jadon Drive, Old Lyme, CT 2 Beds \| 1 Baths \| 936 Sq. Ft.	$445,787
11 Jadon Drive, Old Lyme, CT 3 Beds \| 1.5 Baths \| 1345 Sq. Ft.	$508,155
10 Jadon Drive, Old Lyme, CT 3 Beds \| 2.5 Baths \| 3003 Sq. Ft.	$891,382
32 Ben Franklin Road, Old Lyme, CT 7 Beds \| 4.5 Baths \| 5302 Sq. Ft.	$1,794,273

Property information provided by Smart MLS when last listed in 2022. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06371, CT

Sale history for 249 Whippoorwill Rd

Tax history for 249 Whippoorwill Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06371

Home values near 249 Whippoorwill Rd

More real estate resources