Off Market Jul 2025 for $525K

$586,500

Est. refi paymentEst. refi $2,262/mo

•

2,272

sq ft

4 Sypher Rd, Chester, CT 06412

About this home

Discover a rare gem in the picturesque town of Chester, Connecticut, with this charming 3-bedroom, 2.5-bath colonial home. Nestled on a private 2-acre lot, this property is a dream come true for horse lovers, featuring a barn that offers ample space for your equestrian needs and a chicken coop. Enjoy direct access to nearby state forest trails for riding or exploring. As you step inside, you will be welcomed by a spacious living room featuring a cozy fireplace, perfect for those relaxing evenings. The home also boasts a large family room that opens to a beautiful wood deck, providing a wonderful space for entertaining and enjoying serene views of your expansive property. Upstairs, you will find a spacious primary suite complete with a walk-in closet and a full bath, offering the privacy and comfort you deserve. Chester is known for its delightful eateries, unique galleries, and quaint shops, creating a vibrant community atmosphere. Additionally, the scenic Connecticut River is just a stone's throw away, providing excellent opportunities for boating and fishing, ideal for any outdoor enthusiast. With its convenient location, you are only 2.5 hours from both New York City and Boston. This is a unique opportunity to own a beautiful home in a storybook setting. Embrace the lifestyle you've always dreamed of in this enchanting property!

Single-familyProperty Type

1969Year Built

2.02 acresLot Size

$258Est. Price/Sq.Ft.

2 car garageParking

Listed by Kelly Puorro • Puorro Realty Group

Listed by Brandon Puorro • Puorro Realty Group

Contact: Agent Attribution Contact: (860) 575-8666

Bought with Craig Milton • Re/Max Valley Shore

Source:Smart MLS #24100784

Redfin Estimate

$586,500

$62K since sold in July 2025$7,000 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 4.5% lower than the average sale price ($614K) of 6 comparable homes.

SOLD MAR 6, 2026
$715,000
A
3 beds2.5 baths2,139 sq ft
8 Butter Jones Rd, Chester, CT 06412
SOLD AUG 10, 2026
$450,000
B
3 beds2 baths1,650 sq ft
216 Reservoir Rd, Killingworth, CT 06419
SOLD MAR 11, 2026
$430,000
C
3 beds1.5 baths2,226 sq ft
545 N Roast Meat Hill Rd, Killingworth, CT 06419
SOLD JUL 29, 2026
$730,000
D
3 beds2.5 baths2,848 sq ft
56 Shailer Pond Rd, Deep River, CT 06417
SOLD JUL 13, 2026
$750,000
E
3 beds3 baths2,231 sq ft
51 Witch Hazel Dr, Deep River, CT 06417
SOLD MAY 12, 2026
$610,000
F
3 beds2.5 baths1,887 sq ft
57 Witch Hazel Dr, Deep River, CT 06417

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Earn from this home

Sell

$138,750

Est. take-home

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Refinance

Est. cash available

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Rent

$2,948/mo

Redfin rental estimate

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Market trends in 06412, CT

Last updated July 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

103.9%

+2.4% MoM

Median sale price

$556K

$79K MoM

Avg. days on market

24d

11 days MoM

Recently sold homes

1 MoM

New listings for sale

NEW 9 HRS AGO
$2,995,000
4 beds5 baths4,926 sq ft
288 Middlesex Ave, Chester, CT 06412
$284,900
3 beds1 bath1,217 sq ft
92 Water St, Chester, CT 06412
$269,900
1 bed1 bath1,034 sq ft
90 Water St, Chester, CT 06412
See all

Provided by Redfin

Sale history for 4 Sypher Rd

Date

Event

Price

Smart MLS #24100784

Jul 25, 2025

Sold

$525,000

$231/sq ft

Jul 5, 2025

Pending

—

Jun 11, 2025

Contingent

—

Jun 6, 2025

Listed

$499,000

$220/sq ft

Smart MLS #170137978

Dec 31, 2018

Sold

$296,000

$130/sq ft

Nov 30, 2018

Contingent

—

Nov 15, 2018

Price Changed

$299,900

$132/sq ft

Oct 23, 2018

Listed

$325,000

$143/sq ft

Well maintained 4 bedroom Colonial in a rural setting not far from Chester Village. Open, level lot close to state forest and Cedar Lake. Remodeled kitchen with granite counters. Wood floors. Large family room with propane stove and sliders to private backyard. Living room with fireplace insert. Walk-in pantry. Partially finished basement. Two car oversized garage and 400 sq ft outbuilding/barn. Zoning would allow 3 horses on the property.

Public Records

May 22, 1996

Sold

$180,000

$79/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$5,994 (+0.7%)

$59,620 + $142,210

$201,830

2022

$5,954

$59,620 + $142,210

$201,830

2021

$5,954 (+3.1%)

$59,620 + $142,210

$201,830

2020

$5,776 (−0.6%)

$59,620 + $142,210

$201,830

2019

$5,811 (+10.8%)

$59,620 + $142,210

$201,830

2018

$5,243 (+2.9%)

$63,130 + $130,250

$193,380

2017

$5,097 (+3.1%)

$63,130 + $130,250

$193,380

2016

$4,945 (+3.0%)

$63,130 + $130,250

$193,380

2014

$4,800 (−1.6%)

$63,130 + $130,250

$193,380

2011

$4,880

$77,120 + $145,200

$222,320

Tax history for 4 Sypher Rd

Year

Property tax

Land + Additions

Assessment*

2023

$5,994 (+0.7%)

$59,620 + $142,210

$201,830

2022

$5,954

$59,620 + $142,210

$201,830

2021

$5,954 (+3.1%)

$59,620 + $142,210

$201,830

2020

$5,776 (−0.6%)

$59,620 + $142,210

$201,830

2019

$5,811 (+10.8%)

$59,620 + $142,210

$201,830

2018

$5,243 (+2.9%)

$63,130 + $130,250

$193,380

2017

$5,097 (+3.1%)

$63,130 + $130,250

$193,380

2016

$4,945 (+3.0%)

$63,130 + $130,250

$193,380

2014

$4,800 (−1.6%)

$63,130 + $130,250

$193,380

2011

$4,880

$77,120 + $145,200

$222,320

*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

2.02 Acres

Year renovated

1998

Sq. Ft.

2,272

Year built

1969

Style

Single Family Residential

County

Middlesex County

APN

940103

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

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

Interior

Interior Information
Total Rooms: 7
Laundry Room Info: Main Level
Fireplaces Total: 1
Cooling System: Window Unit
Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 2
# of Baths (Half): 1

Bedroom Information
Beds Total: 3

Room Information
Basement Description: Full, Partially Finished
Has Attic
Attic Description: Access Via Hatch

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Aluminum
Exterior Features: Barn, Deck, Garden Area, Stable, Stone Wall

Lot Information
Lot Description: Lightly Wooded, Level Lot

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

Property Information
Property Type: Single Family For Sale
Property Info: Horse Property
Living Area SQFT Per Public Record: 2272

Financial

Assessments Information
Assessed Value: $277,620

Utilities

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

Location

School Information
Middle Jr High School: Region 4
High School: Valley
Elementary School: Chester

Location Information
State: Connecticut
Nearby Amenities: Health Club, Lake, Library, Medical Facilities, Park, Playground/Tot Lot, Shopping/Mall, Stables/Riding
Directions: GPS Friendly
County: Middlesex

Public facts

Beds: 4
Baths: 2.0
Sq. Ft.: 2,272
Stories: 2.0
Lot Size: 2.02 acres
Style: Single Family Residential
Year Built: 1969
Year Renovated: 1998
County: Middlesex County
APN: 940103

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 3

Around this home

Schools
Places
Transit

Chester Elementary School

Public PreK-6 • Assigned • 3.1mi

7/10

John Winthrop Middle School

Public 7-8 • Assigned • 3.5mi

4/10

Valley Regional High School

Public 9-12 • Assigned • 3.7mi

7/10

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 93° expected this year, 17 days in 30 years

6/10 Wind Factor

69% chance of strong winds in next 30 years

4/10 Air Factor

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

Provided by First Street

Historical weather

Chester, CT • 06412

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 8.9 hours in June and 4.5 hours in December, which is comparable to the U.S. average for solar exposure.

8.9 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$558,000 – $675,000

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Nearby similar homes

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5 beds5 baths4,190 sq ft

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3 beds1 bath1,217 sq ft

92 Water St, Chester, CT 06412

$2,200,000

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New listings for sale in 06412

NEW 9 HRS AGO

$2,995,000

4 beds5 baths4,926 sq ft

288 Middlesex Ave, Chester, CT 06412

$284,900

3 beds1 bath1,217 sq ft

92 Water St, Chester, CT 06412

$269,900

1 bed1 bath1,034 sq ft

90 Water St, Chester, CT 06412

Home values near 4 Sypher Rd

Data from public records.

Address	Redfin Estimate
8 Sypher Rd, Chester, CT 3 Beds \| 2 Baths \| 1250 Sq. Ft.	$437,304
6 Sypher Rd, Chester, CT 3 Beds \| 2 Baths \| 2994 Sq. Ft.	$620,357

Address	Redfin Estimate
16 Sypher Rd, Chester, CT 2 Beds \| 2.5 Baths \| 1726 Sq. Ft.	$580,756
3 Sypher Rd, Chester, CT 4 Beds \| 3 Baths \| 1911 Sq. Ft.	$550,113

Address	Redfin Estimate
2 Sypher Rd, Chester, CT 4 Beds \| 2.5 Baths \| 2278 Sq. Ft.	$541,827
14 Sypher Rd, Chester, CT 2 Beds \| 3 Baths \| 1708 Sq. Ft.	—

Property information provided by Smart MLS when last listed in 2025. 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 06412, CT

Sale history for 4 Sypher Rd

Tax history for 4 Sypher Rd

Public record

Property details

Around this home

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06412

Home values near 4 Sypher Rd

More real estate resources