Off Market Sep 2025 for $1.1M

$1,353,956

Est. refi paymentEst. refi $7,472/mo

•

7,643

sq ft

8 Up The Rd, West Simsbury, CT 06092

About this home

Privately set on estate-like 2 acre grounds beautifully landscaped w/graceful circular drive,stone walls,& lush lawns accented by vibrant perennial gardens. In 2002 a thoughtfully designed major addition elevated the home w/expanded living - an exceptional luxury residence offering a perfect blend of light-filled interiors & expansive living spaces ideal for both everyday & grand-scale entertaining. A refined & relaxed open concept brightened by abundant windows framing peaceful views. Modern Frch drs open to the Sunrm,a highlight of the home w/custom built ins & amazing entertainers kitch w/Subzeros,wine cave,fridge drawers & more! Seamless access from many rms invites you to the backyard oasis w/stunning pool,patio & decks offering endless possibilities for leisure & lifestyle.The stylish expansive gourmet Kit opens to FR w/gorgeous river rock frpl.Stunning 10' islnd,prof grade appl,& brkfst rm w/picturesque views insure the Kit takes center stage at every gathering. Indulge in the comfort of serene 1st fl Primary w/generous dressing room/wlk in & well appointed spa bath. The bright upper level offers 3 spacious ensuite bedrooms,each w/private bth, plus a 5th ensuite bed/bonus rm & a flex rm ideal as 2nd study.Great versatile space for game rm or gym in spacious finished LL.3 car attached plus 1 car det gar.Simsbury is conveniently located between NYC & Boston w/easy access to Bradley Int'l airport. Enjoy top schools,miles of hike/bike trails,and an award winning community.

Single-familyProperty Type

1968Year Built

2 acresLot Size

$177Est. Price/Sq.Ft.

4 car garageParking

Listed by Ellen Seifts • Berkshire Hathaway NE Prop.

Bought with Christine Horkman • Regency Real Estate, LLC

Source:Smart MLS #24109701

Redfin Estimate

$1,353,956

$204K since sold in September 2025$88K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 41.7% higher than the average sale price ($956K) of 6 comparable homes.

SOLD JUL 15, 2026
$875,000
A
4 beds3.5 baths4,233 sq ft
158 Westledge Rd, West Simsbury, CT 06092
SOLD AUG 19, 2026
$1,160,000
B
5 beds4 baths5,267 sq ft
11 Whitman Pond Rd, Simsbury, CT 06070
SOLD AUG 20, 2026
$785,000
C
4 beds3.5 baths3,106 sq ft
181 Farms Village Rd, West Simsbury, CT 06092
SOLD AUG 17, 2026
$585,000
D
4 beds3 baths2,957 sq ft
47 Westledge Rd, West Simsbury, CT 06092
SOLD JUL 1, 2026
$1,570,000
E
4 beds5 baths7,160 sq ft
22 Joshua Dr, West Simsbury, CT 06092
SOLD JUL 24, 2026
$760,000
F
5 beds3.5 baths3,317 sq ft
79 High Valley Dr, Canton, CT 06019

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Earn from this home

Sell

$369,154

Est. take-home

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Refinance

Est. cash available

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Rent

$4,611/mo

Redfin rental estimate

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Market trends in 06092, CT

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

112.2%

+2.2% MoM

Median sale price

$630K

$20K MoM

Avg. days on market

10d

19 days MoM

Recently sold homes

8 MoM

New listings for sale

COMING SOON
$1,150,000
6 beds4 baths5,141 sq ft
29 Pilfershire Ln, West Simsbury, CT 06092
$549,000
3 beds2 baths2,450 sq ft
57 Westledge Rd, West Simsbury, CT 06092
$550,000
4 beds3 baths2,622 sq ft
7 Banbury Dr, West Simsbury, CT 06092
COMING SOON
$649,000
4 beds2.5 baths2,700 sq ft
25 Watson Dr, West Simsbury, CT 06070
COMING SOON
$759,000
4 beds2.5 baths2,997 sq ft
10 Saw Mill Rd, West Simsbury, CT 06092
See all

Provided by Redfin

Sale history for 8 Up The Rd

Date

Event

Price

Smart MLS #24109701

Sep 10, 2025

Sold

$1,150,000

$150/sq ft

Aug 12, 2025

Pending

—

Jul 31, 2025

Contingent

—

Jul 15, 2025

Listed

$1,150,000

$150/sq ft

Smart MLS #170410299

Jul 30, 2021

Listing Removed

—

Jun 24, 2021

Listed

$1,150,000

$150/sq ft

Smart MLS #G10015368

Sep 16, 2015

Sold

$720,000

$94/sq ft

Jan 20, 2015

Listed

$739,900

$97/sq ft

BEST VALUE IN TOWN! Wonderful curb appeal with stone walls and circular driveway! Totally redone in 2003 with exceptional additions-feels like new! Stunning high quality kitchen and baths, gorgeous riverstone fireplaced family room, first floor master bedroom suite with luxurious bath, private guest quarters and an amazing four season sunroom, ideal for entertaining. Inviting open floor plan overlooking the private grounds with a heated inground pool, spa, pool house and gardens! Additional square footage in lower level. A real beauty in West Simsbury!

Smart MLS #G685952

Jan 22, 2015

Listing Removed

—

Jun 10, 2014

Listed

$899,000

$118/sq ft

Smart MLS #G669598

Jun 6, 2014

Listing Removed

—

Dec 11, 2013

Listed

$975,000

$128/sq ft

Smart MLS #G654653

Sep 30, 2013

Listing Removed

—

Jun 18, 2013

Listed

$1,250,000

$164/sq ft

Smart MLS #G641527

Jun 18, 2013

Listing Removed

—

Jan 25, 2013

Listed

$1,399,000

$183/sq ft

Smart MLS #G630770

Jan 25, 2013

Listing Removed

—

Aug 21, 2012

Listed

$1,499,999

$196/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$30,120 (+2.6%)

$122,150 + $759,570

$881,720

2024

$29,370 (+4.7%)

$122,150 + $759,570

$881,720

2023

$28,056 (+46.1%)

$122,150 + $759,570

$881,720

2022

$19,199

$129,180 + $367,820

$497,000

2021

$19,199 (+4.1%)

$129,180 + $367,820

$497,000

2020

$18,434 (−0.6%)

$129,180 + $367,820

$497,000

2019

$18,548 (−0.7%)

$129,180 + $367,820

$497,000

2018

$18,682 (−23.2%)

$129,180 + $367,820

$497,000

2017

$24,321 (+4.4%)

$150,180 + $477,290

$627,470

2016

$23,292 (−13.0%)

$150,180 + $477,290

$627,470

2014

$26,777 (−3.6%)

$150,170 + $570,800

$720,970

2011

$27,765

$150,170 + $570,800

$720,970

Tax history for 8 Up The Rd

Year

Property tax

Land + Additions

Assessment*

2025

$30,120 (+2.6%)

$122,150 + $759,570

$881,720

2024

$29,370 (+4.7%)

$122,150 + $759,570

$881,720

2023

$28,056 (+46.1%)

$122,150 + $759,570

$881,720

2022

$19,199

$129,180 + $367,820

$497,000

2021

$19,199 (+4.1%)

$129,180 + $367,820

$497,000

2020

$18,434 (−0.6%)

$129,180 + $367,820

$497,000

2019

$18,548 (−0.7%)

$129,180 + $367,820

$497,000

2018

$18,682 (−23.2%)

$129,180 + $367,820

$497,000

2017

$24,321 (+4.4%)

$150,180 + $477,290

$627,470

2016

$23,292 (−13.0%)

$150,180 + $477,290

$627,470

2014

$26,777 (−3.6%)

$150,170 + $570,800

$720,970

2011

$27,765

$150,170 + $570,800

$720,970

*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

6.5

Stories

Lot width

—

Lot depth

—

Lot size

2 Acres

Year renovated

2000

Sq. Ft.

6,759

Year built

1968

Style

Single Family Residential

County

Hartford County

APN

695349

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 10, 2026.

Property details

Parking

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

Interior

Interior Information
Total Rooms: 13
Laundry Room Info: Main Level
Interior Features: Auto Garage Door Opener, Cable - Available, Open Floor Plan, Security System
Fireplaces Total: 3
Cooling System: Central Air
Appliances Included: Gas Cooktop, Wall Oven, Microwave, Range Hood, Subzero, Dishwasher, Disposal, Washer, Dryer, Wine Chiller

Bathroom Information
# of Baths (Full): 6
# of Baths (Half): 1

Bedroom Information
Beds Total: 5

Room Information
Rooms Additional: Foyer, Laundry Room, Mud Room
Basement Description: Full, Partially Finished
Has Attic
Attic Description: Pull-Down Stairs

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Shingle, Clapboard, Wood
Exterior Features: Underground Utilities, Shed, Deck, Stone Wall, Underground Sprinkler, Patio

Lot Information
Lot Description: Lightly Wooded, Level Lot, Professionally Landscaped

Pool Information
Swimming Pool
Pool Description: Gunite, In Ground Pool

Building Information
Foundation Type: Concrete
Construction Description: Frame

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 6759

Financial

Assessments Information
Assessed Value: $881,720

Utilities

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

Location

School Information
Middle Jr High School: Henry James
High School: Simsbury
Elementary School: Tootin' Hills

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Health Club, Private School(s), Public Rec Facilities, Tennis Courts
Directions: Westledge Rd to Woodchuck Hill to Up the Road. Up the Road is a private drive. See attachments for further information.
County: Hartford

Public facts

Beds: 5
Baths: 6.5
Sq. Ft.: 6,759
Stories: 2.0
Lot Size: 2 acres
Style: Single Family Residential
Year Built: 1968
Year Renovated: 2000
County: Hartford County
APN: 695349

Home facts updated by county records on Jul 10, 2026

Other

Documents & Disclosures
Supplement Count Public: 4

Around this home

Schools

Tootin' Hills School

Public K-6 • Assigned • 1.3mi

9/10

Henry James Memorial School

Public 7-8 • Assigned • 3.0mi

8/10

Simsbury High School

Public 9-12 • Assigned • 2.7mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Historical weather

West Simsbury, CT • 06092

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

8.8 hrs

4.2 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.29M – $1.56M

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Nearby similar homes

NEW CONSTRUCTION

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OPEN SAT, 2PM TO 4PM

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New listings for sale in 06092

COMING SOON

$1,150,000

6 beds4 baths5,141 sq ft

29 Pilfershire Ln, West Simsbury, CT 06092

$549,000

3 beds2 baths2,450 sq ft

57 Westledge Rd, West Simsbury, CT 06092

$550,000

4 beds3 baths2,622 sq ft

7 Banbury Dr, West Simsbury, CT 06092

COMING SOON

$649,000

4 beds2.5 baths2,700 sq ft

25 Watson Dr, West Simsbury, CT 06070

COMING SOON

$759,000

4 beds2.5 baths2,997 sq ft

10 Saw Mill Rd, West Simsbury, CT 06092

Home values near 8 Up The Rd

Data from public records.

Address	Redfin Estimate
7 Up the Road, West Simsbury, CT 5 Beds \| 4 Baths \| 5362 Sq. Ft.	$1,320,852
5 Up the Road, West Simsbury, CT 3 Beds \| 4 Baths \| 2470 Sq. Ft.	$740,084

Address	Redfin Estimate
12 Up the Road, West Simsbury, CT 3 Beds \| 4.5 Baths \| 3495 Sq. Ft.	$850,361
9 Up the Road, West Simsbury, CT 4 Beds \| 2.5 Baths \| 3019 Sq. Ft.	$765,645

Address	Redfin Estimate
4 Up the Road, West Simsbury, CT 5 Beds \| 7 Baths \| 5104 Sq. Ft.	$1,431,877
17 Ruthies Lane, West Simsbury, CT 4 Beds \| 4 Baths \| 5117 Sq. Ft.	$1,073,895

Property information provided by Smart MLS when last listed in 2025. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06092, CT

Sale history for 8 Up The Rd

Tax history for 8 Up The Rd

Public record

Property details

Around this home

Schools

Lifestyle

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06092

Home values near 8 Up The Rd

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