250 Upper Whittemore Rd, Middlebury, CT 06762

Off Market Aug 2020 for $2.8M

$3,768,384

Est. refi paymentEst. refi $3,163/mo

•

8,408

sq ft

250 Upper Whittemore Rd, Middlebury, CT 06762

About this home

Sweet dreams are made of this! It won’t be easy to click out of vacation mode in this exceptionally stylish home designed by iconic architects Demetriades & Walker, whose approach to modernism & site integration is spirited by the rich architectural traditions of the past. Interior highlights: spacious great room w/ double-height ceilings, bluestone FP, grand-scale windows w/ motorized shades, wet bar w/ walnut cabinetry & 2 Sub Zero fridges. The spacious chef’s kitchen features walnut cabinetry, white marble countertops, large dining & French doors to covered deck w/ full outdoor kitchen. 2 Sub Zero refrigerators, Miele dishwasher, all Wolf appliances. Walk-in pantry boasts Sub Zero, Freezer, Ice Maker & Miele Dishwasher. Main floor comprised of a FR, sitting room w/ custom shelving & hidden TV wall, office, laundry room, mud room w/ Porcelain flooring & two powder rooms. The 2nd level features grand master suite, w/ 2 dressing rooms & 5-piece bath including a 2-person walk-in shower, Waterworks tub, marble tiles, heated floors & access to balcony. 2 guest bedroom suites & 2 children’s bedrooms. The verdant property offers a myriad of places from which to soak up the sun & sights. Ext. amenities: in-ground heated pool w/ motorized solar/safety cover, custom field stone walls, IPE wood decking, built-in irrigation & garden lighting. A covered porch w/ outdoor kitchen w/ bluestone gas FP, TV, ceiling fans & heaters, grill, ice maker, beer tap, sink, fridge & gas stovetop.

Single-familyProperty Type

2011Year Built

20 acresLot Size

$448Est. Price/Sq.Ft.

3 car garageParking

Listed by Mark Madonna • William Pitt Sotheby's Int'l

Listed by Jeffrey Phillips • William Pitt Sotheby's Int'l

Bought with Jeffrey Phillips • William Pitt Sotheby's Int'l

Bought with Mark Madonna • William Pitt Sotheby's Int'l

Source:Smart MLS #170296681

Redfin Estimate

$3,768,384

$968K since sold in August 2020$262K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 264.5% higher than the average sale price ($1.03M) of 5 comparable homes.

SOLD AUG 10, 2026
$950,000
A
5 beds4.5 baths4,473 sq ft
188 Settlers Hill Rd, Southbury, CT 06488
SOLD JUN 10, 2026
$950,000
B
4 beds3.5 baths4,861 sq ft
112 Southridge Rd, Southbury, CT 06488
SOLD JUL 15, 2026
$1,300,000
C
4 beds4 baths6,415 sq ft
162 Britiani Rd, Southbury, CT 06488
SOLD AUG 25, 2026
$1,129,000
D
4 beds2.5 baths4,260 sq ft
198 Little Fox Ln, Southbury, CT 06488
SOLD JUN 29, 2026
$840,000
E
4 beds3 baths3,925 sq ft
146 Lantern Park Ln S, Southbury, CT 06488

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Earn from this home

Sell

$1,576,994

Est. take-home

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Refinance

Est. cash available

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Market trends in 06762, CT

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.6%

+0.5% MoM

Median sale price

$575K

$78 MoM

Avg. days on market

47d

0 days MoM

Recently sold homes

8 MoM

New listings for sale

$499,900
2 beds1 bath798 sq ft
89 Sandy Beach Rd #89, Middlebury, CT 06762
OPEN TODAY, 11AM TO 1PM
$350,000
3 beds2 baths1,466 sq ft
138 Steinmann Ave, Middlebury, CT 06762
COMING SOON
$599,900
3 beds2.5 baths2,360 sq ft
58 Shadduck Rd, Middlebury, CT 06762
$819,000
4 beds2.5 baths2,700 sq ft
18 Hunting Ridge Rd, Middlebury, CT 06762
$600,000
3 beds2.5 baths1,957 sq ft
16 Caveson Ct #16, Middlebury, CT 06762
$675,000
4 beds3.5 baths1,940 sq ft
46 Washington Dr, Middlebury, CT 06762
$474,900
3 beds2.5 baths1,837 sq ft
133 Algin Dr, Middlebury, CT 06762
$479,900
4 beds2 baths1,630 sq ft
106 Steinmann Ave, Middlebury, CT 06762
$239,900
1 bed1 bath889 sq ft
35 Nutmeg Rd Unit B2, Middlebury, CT 06762
See all

Provided by Redfin

Sale history for 250 Upper Whittemore Rd

Date

Event

Price

Smart MLS #170296681

Aug 27, 2020

Sold

$2,800,000

$333/sq ft

Jul 1, 2020

Contingent

—

May 20, 2020

Listed

$2,850,000

$339/sq ft

Smart MLS #170118237

Nov 8, 2019

Listing Removed

—

May 3, 2019

Relisted

—

May 2, 2019

Listing Removed

—

Mar 19, 2019

Price Changed

$2,850,000

$339/sq ft

Aug 25, 2018

Listed

$3,500,000

$416/sq ft

Public Records

Jun 13, 2008

Sold

$490,000

$58/sq ft

Public Records

Jan 12, 2007

Sold

$450,000

$54/sq ft

Year

Property tax

Land + Additions

Assessment*

2022

$53,476 (+24.5%)

$169,500 + $1,541,200

$1,710,700

2021

$42,966 (−0.8%)

$186,000 + $1,047,600

$1,233,600

2020

$43,299 (+5.1%)

$186,000 + $1,047,600

$1,233,600

2019

$41,202 (+2.7%)

$186,000 + $1,047,600

$1,233,600

2018

$40,104 (+3.2%)

$186,000 + $1,047,600

$1,233,600

2017

$38,846 (+2.1%)

$186,000 + $1,047,600

$1,233,600

2016

$38,043 (+5.7%)

$199,600 + $1,027,200

$1,226,800

2014

$35,994 (+1.7%)

$199,600 + $1,027,200

$1,226,800

2011

$35,405

$199,600 + $1,027,200

$1,226,800

Tax history for 250 Upper Whittemore Rd

Year

Property tax

Land + Additions

Assessment*

2022

$53,476 (+24.5%)

$169,500 + $1,541,200

$1,710,700

2021

$42,966 (−0.8%)

$186,000 + $1,047,600

$1,233,600

2020

$43,299 (+5.1%)

$186,000 + $1,047,600

$1,233,600

2019

$41,202 (+2.7%)

$186,000 + $1,047,600

$1,233,600

2018

$40,104 (+3.2%)

$186,000 + $1,047,600

$1,233,600

2017

$38,846 (+2.1%)

$186,000 + $1,047,600

$1,233,600

2016

$38,043 (+5.7%)

$199,600 + $1,027,200

$1,226,800

2014

$35,994 (+1.7%)

$199,600 + $1,027,200

$1,226,800

2011

$35,405

$199,600 + $1,027,200

$1,226,800

*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

7.52 Acres

Year renovated

—

Sq. Ft.

7,858

Year built

2011

Style

Multi-Family (2-4 Unit)

County

New Haven County

APN

2070781

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 12, 2023.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage
Garages Number: 3

Interior

Interior Information
Total Rooms: 15
Laundry Room Location: large double with dog wash
Laundry Room Info: Main Level
Interior Features: Audio System, Auto Garage Door Opener, Cable - Available, Cable - Pre-wired, Open Floor Plan, Security System
In-Law Apartment: Yes
In-Law Access: First Floor
Entertainment System, Lighting, Security System, Thermostat(s)
Fireplaces Total: 2
Cooling System: Central Air, Zoned
Appliances Included: Gas Cooktop, Wall Oven, Range Hood, Freezer, Subzero, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller

Bathroom Information
# of Baths (Full): 5
# of Baths (Half): 2

Bedroom Information
Beds Total: 6

Room Information
Rooms Additional: Laundry Room, Mud Room, Wine Cellar
Basement Description: Partially Finished, Concrete Floor, Interior Access

Exterior

Exterior Features
Roof Information: Wood Shingle, Shake
Exterior Siding: Shingle, Cedar
Exterior Features: Balcony, Covered Deck, Deck, French Doors, Garden Area, Grill, Lighting, Stone Wall, Underground Sprinkler

Lot Information
Lot Description: Open Lot, Secluded, Water View, Lightly Wooded, Fence - Stone, Professionally Landscaped

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

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

Property Information
Waterfront Description: View
Property Type: Single Family For Sale
Property Info: Horse Property
Living Area SQFT Per Public Record: 7858
Driveway Type: Private, Paved, Dirt, Gravel

Financial

Assessments Information
Assessed Value: $1,233,600

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Electric, Propane
Heat Type: Hot Air, Zoned
Heat Fuel Type: Propane
Fuel Tank Location: In Basement
Energy Features: Programmable Thermostat, Thermopane Windows

Location

School Information
High School: Per Board of Ed
Elementary School: Per Board of Ed

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Lake, Library, Medical Facilities, Private Rec Facilities, Private School(s), Stables/Riding, Tennis Courts
Directions: on GPS
County: New Haven

Public facts

Beds: 6
Baths: 6.0
Sq. Ft.: 7,858
Stories: 2.0
Lot Size: 7.52 acres
Style: Multi-Family (2-4 Unit)
Year Built: 2011
Year Renovated: —
County: New Haven County
APN: 2070781

Home facts updated by county records on Jul 12, 2023

Around this home

Schools

Long Meadow Elementary School

Public PreK-5 • Assigned • 2.0mi

5/10

Memorial Middle School

Public 6-8 • Assigned • 2.4mi

8/10

Pomperaug Regional High School

Public 9-12 • Assigned • 2.3mi

8/10

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

3/10 Heat Factor

7 days above 97° expected this year, 14 days in 30 years

5/10 Wind Factor

25% chance of strong winds in next 30 years

3/10 Air Factor

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

Provided by First Street

Historical weather

Middlebury, CT • 06762

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

8.8 hrs

4.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$3.58M – $4.33M

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Home values near 250 Upper Whittemore Rd

Data from public records.

Address	Redfin Estimate
378 Upper Whittemore Rd, Middlebury, CT 4 Beds \| 3 Baths \| 3928 Sq. Ft.	$1,522,102
167 Upper Whittemore Rd, Middlebury, CT 3 Beds \| 1.5 Baths \| 1636 Sq. Ft.	$552,365

Address	Redfin Estimate
305 Upper Whittemore Rd, Middlebury, CT 4 Beds \| 4.5 Baths \| 4555 Sq. Ft.	$1,102,835
444 Upper Whittemore Rd, Middlebury, CT 6 Beds \| 7 Baths \| 10266 Sq. Ft.	$2,356,059

Address	Redfin Estimate
245 Upper Whittemore Rd, Middlebury, CT 3 Beds \| 2.5 Baths \| 2990 Sq. Ft.	$871,304
40 Upper Whittemore Rd, Middlebury, CT 4 Beds \| 3 Baths \| 3088 Sq. Ft.	$772,617

Property information provided by Smart MLS when last listed in 2020. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06762, CT

Sale history for 250 Upper Whittemore Rd

Tax history for 250 Upper Whittemore Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06762

Home values near 250 Upper Whittemore Rd

More real estate resources