108 Old Boston Post Rd, Old Saybrook, CT 06475

Off Market Apr 2020 for $344K

$754,404

Est. refi paymentEst. refi $2,671/mo

•

2,111

sq ft

108 Old Boston Post Rd, Old Saybrook, CT 06475

About this home

Nostalgic Charm! Nestled in the village of Old Saybrook this 1720 “John Pratt” Cape Cod home, sits on a level yard of nearly 1 acre that you can view from your oversized deck. This historic home delivers charm and warmth throughout its 2111 sqft of period craftsmanship. There are 3 Bedrooms, including a downstairs MBS, and 3 full and roomy baths plus a room for an office. Whether it is the wide floorboards in some of the rooms or the cozy fireplace in the Master bedroom, today’s homes just don’t deliver the same feeling that the legendary style of this antique home has to offers. This near downtown location is ideal. You can easily stroll to Main St., enjoy an evening of entertainment at “The Kate” followed by dinner at one of the many walkable restaurants, enjoy a nightcap and take a leisurely walk home. Saybrook Junction is just a 10 min walk away where you can catch a train to NYC or Boston. Although with your Old Saybrook beach rights to both the private town beach & Harvey’s public beach you may just want to stay in town. Sidewalks abound and you may decide to take a walk or jog to Saybrook point and watch the boats, chat with the fishermen, play mini-golf or take advantage of the SPA at the Inn. Come and see for yourself. Home being in offered with 1 year American Home Sheild Mechanical and Appliance protection plan.

Single-familyProperty Type

1720Year Built

0.91 acresLot Size

$357Est. Price/Sq.Ft.

Listed by Melissa Pardi • Berkshire Hathaway NE Prop.

Listed by Peter Zucco • Berkshire Hathaway NE Prop.

Bought with Sandra Orsie • Berkshire Hathaway NE Prop.

Source:Smart MLS #170031733

Redfin Estimate

$754,404

$410K since sold in April 2020$8,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 20.1% lower than the average sale price ($944K) of 6 comparable homes.

SOLD JUN 30, 2026
$900,000
A
3 beds2.5 baths2,170 sq ft
129 Old Boston Post Rd, Old Saybrook, CT 06475
BOUGHT WITH REDFIN JUN 15, 2026
$935,000
B
4 beds3 baths2,516 sq ft
24 Cottage Pl, Old Saybrook, CT 06475
SOLD DEC 16, 2025
$935,000
C
3 beds2.5 baths2,396 sq ft
19 Lynde St, Old Saybrook, CT 06475
SOLD DEC 2, 2025
$650,000
D
3 beds3 baths1,720 sq ft
21 Cottage Pl, Old Saybrook, CT 06475
SOLD JUL 17, 2026
$750,000
E
3 beds2.5 baths1,604 sq ft
29 Old Post Rd, Old Saybrook, CT 06475
SOLD DEC 1, 2025
$1,495,000
F
4 beds3.5 baths2,425 sq ft
66 Pennywise Ln, Old Saybrook, CT 06475

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Earn from this home

Sell

$469,016

Est. take-home

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Refinance

Est. cash available

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Rent

$4,351/mo

Redfin rental estimate

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Market trends in 06475, CT

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

99.9%

0.6% MoM

Median sale price

$735K

$10K MoM

Avg. days on market

43d

6 days MoM

Recently sold homes

8 MoM

New listings for sale

NEW 13 HRS AGO
$1,550,000
4 beds3 baths3,188 sq ft
108 Maple Ave, Old Saybrook, CT 06475
NEW 18 HRS AGO
$969,000
2 beds2.5 baths2,132 sq ft
25 Sheffield St #3, Old Saybrook, CT 06475
$499,999
3 beds1 bath2,718 sq ft
35 School House Rd, Old Saybrook, CT 06475
OPEN SUN, 12PM TO 2PM
$799,500
3 beds1.5 baths1,856 sq ft
71 Knollwood Dr, Old Saybrook, CT 06475
$1,699,000
4 beds2.5 baths3,515 sq ft
11 Fencove Ct, Old Saybrook, CT 06475
COMING SOON
$1,599,000
4 beds3.5 baths2,734 sq ft
138 N Cove Rd, Old Saybrook, CT 06475
OPEN SUN, 11AM TO 1PM
$797,000
2 beds2.5 baths1,565 sq ft
100 Dudley Ave Unit F30, Old Saybrook, CT 06475
$285,000
3 beds1 bath941 sq ft
43 Quarry St, Old Saybrook, CT 06475
See all

Provided by Redfin

Sale history for 108 Old Boston Post Rd

Date

Event

Price

Smart MLS #170031733

Apr 6, 2020

Sold

$344,000

$163/sq ft

Feb 24, 2020

Contingent

—

Feb 3, 2020

Price Changed

$349,900

$166/sq ft

Dec 17, 2019

Relisted

—

Dec 7, 2019

Contingent

—

Jul 31, 2019

Price Changed

$375,000

$178/sq ft

May 31, 2019

Price Changed

$399,000

$189/sq ft

May 31, 2019

Relisted

—

May 26, 2019

Listing Removed

—

May 26, 2019

Relisted

—

Jul 21, 2018

Listing Removed

—

May 21, 2018

Contingent

—

May 18, 2018

Relisted

—

Apr 2, 2018

Listing Removed

—

Mar 22, 2018

Relisted

—

Mar 16, 2018

Contingent

—

Feb 5, 2018

Pending

—

Dec 19, 2017

Listed

—

Nov 13, 2017

Listed

$429,900

$204/sq ft

Smart MLS #M9148234

Aug 1, 2014

Sold

$410,000

$194/sq ft

Jun 5, 2014

Listed

$439,900

$208/sq ft

Public Records

Apr 22, 2009

Sold

$429,999

$204/sq ft

Smart MLS #M9112968

Sep 19, 2008

Listed

$429,999

$204/sq ft

Public Records

May 17, 2000

Sold

$198,500

$94/sq ft

Smart MLS #M9055274

Oct 14, 1999

Listed

$210,000

$99/sq ft

Public Records

Dec 16, 1997

Sold

$110,000

$52/sq ft

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Year

Property tax

Land + Additions

Assessment*

2023

$5,198 (+1.8%)

$74,800 + $179,400

$254,200

2022

$5,104 (+0.1%)

$74,800 + $179,400

$254,200

2021

$5,097

$74,800 + $179,400

$254,200

2020

$5,097 (+1.5%)

$74,800 + $179,400

$254,200

2019

$5,020 (−6.3%)

$74,800 + $179,400

$254,200

2018

$5,355 (−0.3%)

$74,800 + $198,400

$273,200

2017

$5,371 (+2.1%)

$74,800 + $198,400

$273,200

2016

$5,262 (+0.4%)

$74,800 + $198,400

$273,200

2014

$5,243 (+22.5%)

$74,800 + $208,600

$283,400

2011

$4,279

$73,700 + $207,800

$281,500

Tax history for 108 Old Boston Post Rd

Year

Property tax

Land + Additions

Assessment*

2023

$5,198 (+1.8%)

$74,800 + $179,400

$254,200

2022

$5,104 (+0.1%)

$74,800 + $179,400

$254,200

2021

$5,097

$74,800 + $179,400

$254,200

2020

$5,097 (+1.5%)

$74,800 + $179,400

$254,200

2019

$5,020 (−6.3%)

$74,800 + $179,400

$254,200

2018

$5,355 (−0.3%)

$74,800 + $198,400

$273,200

2017

$5,371 (+2.1%)

$74,800 + $198,400

$273,200

2016

$5,262 (+0.4%)

$74,800 + $198,400

$273,200

2014

$5,243 (+22.5%)

$74,800 + $208,600

$283,400

2011

$4,279

$73,700 + $207,800

$281,500

*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

0.91 Acres

Year renovated

—

Sq. Ft.

2,111

Year built

1720

Style

Single Family Residential

County

Middlesex County

APN

1026630

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

Garage Information
Garage & Parking: Unpaved, Off Street Parking

Interior

Interior Information
Total Rooms: 8
Laundry Room Location: Main Floor off Mudroom
Interior Features: Cable - Pre-wired
In-Law Apartment: No
Fireplaces Total: 2
Cooling System: Ceiling Fans
Appliances Included: Electric Cooktop, Wall Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 3

Bedroom Information
Beds Total: 3

Room Information
Rooms Additional: Mud Room
Room Count: 8
Basement Description: Full With Hatchway, Unfinished, Concrete Floor
Has Attic
Attic Description: Crawl Space

Exterior

Exterior Features
Roof Information: Slate
Exterior Siding: Clapboard, Wood
Exterior Features: Deck, Garden Area, Gutters, Shed

Lot Information
Lot Description: Historic District, In Flood Zone, Level Lot, Lightly Wooded, Fence - Partial, Fence - Privacy

Building Information
Foundation Type: Stone
Construction Description: Frame, Stone
Color: Yellow

Property Information
Waterfront Description: Beach Rights
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 2111
Driveway Type: Private, Gravel

Financial

Assessments Information
Assessed Value: $254,200

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Septic
Hot Water Description: Electric
Heat Type: Radiator, Steam
Fuel Tank Location: In Basement
Energy Features: Storm Windows, Thermopane Windows

Location

School Information
Middle Jr High School: Old Saybrook
High School: Old Saybrook
Elementary School: Kathleen E. Goodwin

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Health Club, Library, Medical Facilities, Playground/Tot Lot, Public Pool, Public Rec Facilities, Shopping/Mall
Flood Zone
Directions: Route 1 to Main Street. To Old Boston Post Road, right at the light. House is yellow number 108
County: Middlesex

Public facts

Beds: 3
Baths: 3.0
Sq. Ft.: 2,111
Stories: 2.0
Lot Size: 0.91 acres
Style: Single Family Residential
Year Built: 1720
Year Renovated: —
County: Middlesex County
APN: 1026630

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 3

Listing Information
Has Home Warranty Offered

Around this home

Schools

Kathleen E. Goodwin School

Public PreK-4 • Assigned • 0.1mi

6/10

Old Saybrook Middle School

Public 5-8 • Assigned • 0.6mi

8/10

Old Saybrook Senior High School

Public 9-12 • Assigned • 0.6mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

4/10 Flood Factor

Estimated 14-20% chance 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

6/10 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

4 unhealthy days expected this year, 5 days in 30 years

Provided by First Street

Historical weather

Old Saybrook, CT • 06475

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

9 hrs

4.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$717,000 – $868,000

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Nearby similar homes

$1,699,000

4 beds2.5 baths3,515 sq ft

11 Fencove Ct, Old Saybrook, CT 06475

FOR SALE BY OWNER

$666,000

3 beds2 baths1,580 sq ft

15 Mill Rock Rd W, Old Saybrook, CT 06475

$1,175,000

3 beds2 baths2,904 sq ft

26 Willard Ave, Old Saybrook, CT 06475

NEW CONSTRUCTIONVIDEO TOUR

$1,895,000

4 beds3 baths3,023 sq ft

5 Hemlock Dr, Essex, CT 06426

$12,000,000

4 beds1 bath2,059 sq ft

1445 Boston Post Rd, Old Saybrook, CT 06475

$1,025,000

3 beds2 baths1,426 sq ft

37 Woodland Dr, Old Saybrook, CT 06475

New listings for sale in 06475

NEW 13 HRS AGO

$1,550,000

4 beds3 baths3,188 sq ft

108 Maple Ave, Old Saybrook, CT 06475

NEW 18 HRS AGO

$969,000

2 beds2.5 baths2,132 sq ft

25 Sheffield St #3, Old Saybrook, CT 06475

$499,999

3 beds1 bath2,718 sq ft

35 School House Rd, Old Saybrook, CT 06475

OPEN SUN, 12PM TO 2PM

$799,500

3 beds1.5 baths1,856 sq ft

71 Knollwood Dr, Old Saybrook, CT 06475

$1,699,000

4 beds2.5 baths3,515 sq ft

11 Fencove Ct, Old Saybrook, CT 06475

COMING SOON

$1,599,000

4 beds3.5 baths2,734 sq ft

138 N Cove Rd, Old Saybrook, CT 06475

OPEN SUN, 11AM TO 1PM

$797,000

2 beds2.5 baths1,565 sq ft

100 Dudley Ave Unit F30, Old Saybrook, CT 06475

$285,000

3 beds1 bath941 sq ft

43 Quarry St, Old Saybrook, CT 06475

Home values near 108 Old Boston Post Rd

Data from public records.

Address	Redfin Estimate
102 Old Boston Post Rd, Old Saybrook, CT 3 Beds \| 1 Baths \| 1871 Sq. Ft.	$571,821
116 Old Boston Post Rd, Old Saybrook, CT 3 Beds \| 2.5 Baths \| 1596 Sq. Ft.	$631,804

Address	Redfin Estimate
88 Old Boston Post Rd, Old Saybrook, CT 3 Beds \| 2 Baths \| 1500 Sq. Ft.	$816,502
130 Old Boston Post Rd, Old Saybrook, CT 3 Beds \| 2.5 Baths \| 2023 Sq. Ft.	$754,832

Address	Redfin Estimate
110 Old Boston Post Rd, Old Saybrook, CT 4 Beds \| 3 Baths \| 1718 Sq. Ft.	$750,957
136 Old Boston Post Rd, Old Saybrook, CT 3 Beds \| 2 Baths \| 1924 Sq. Ft.	$634,812

Property information provided by Smart MLS when last listed in 2017. This data may not match . 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 06475, CT

Sale history for 108 Old Boston Post Rd

Tax history for 108 Old Boston Post Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06475

Home values near 108 Old Boston Post Rd

More real estate resources