245 Upper Whittemore Road Middlebury, CT $ 815,000
245 Upper Whittemore Road
$ 815,000
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245 Upper Whittemore Road

Middlebury, CT, 06762
$ 815,000
Bedrooms3 Baths2.1 Sq 2,990

Monthly Estimate*

$ 5,018

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Single Family Home for sale in Middlebury, CT

for $815,000 with 3 bedrooms and 2 full baths, 1 half bath. This 2,990 square foot home was built in 2005 on a lot size of 3.03.

Enjoy magnificent sunsets from this exceptional home, privately set on just over three acres in one of the area's most desirable locations. The beautifully landscaped grounds offer both open space and a wooded backdrop for added privacy, along with views of a neighboring stone wall. An in-ground heated saltwater pool is surrounded by an expansive patio and charming pergola-perfect for outdoor entertaining. Three garages are conveniently accessible from both the upper and lower driveways. Inside, the home features 2,990 square feet of thoughtfully designed living space with custom touches throughout. The spacious kitchen includes a dining area, breakfast bar, and a 36" GE Monogram dual-fuel range, offering ample space for cooking and gathering. The adjoining 23' x 20' family room provides a welcoming setting, a propane fired custom fireplace and overlooks the scenic rear property. The primary suite features a walk-in closet, an additional closet, and an updated full bath. The main level is completed by a formal dining room, private office/library, powder room, and laundry area. Upstairs, you'll find two additional bedrooms, a full bath, and a flexible guest area and lots of room for expansion. Additional highlights include the lush grounds, patio, heated saltwater pool, pergola, and more. The house was built with 3 bedrooms, but the septic system supports a 4 bedroom home.

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Single Family Contingent

Price

$ 815,000

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 14,608

Style

Lot Size

3.03

Year Built

2005

Town/City

Middlebury

MLS | Web ID

24167463

Features
General
Zoning R40
Neighborhood N/A
County New Haven
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Under Contract
Acres 3.03
Directions Route 64 to Upper Whittemore or Middlebury Road to Charcoal Ave to Tranquility Road to Upper Whittemore.
High School Pomperaug
City Middlebury
Elementary School Long Meadow
Sq Ft Total 2990
DOM 1
Year Built 2005
Style Cape Cod
Year Built Source Public Records
Handicap Features Bath Grab Bars Lever Door Handles
Pool Description Heated Vinyl Salt Water In Ground Pool
Energy Features Generator Ridge Vents Thermopane Windows
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Interior
Cooling System Central Air
Total Rooms 8
Basement Description Full Full With Walk-Out
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Exterior
Water Source Private Well
Lot Description Professionally Landscaped
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* Excluded Features
List By
Donna Bannon

Listing Agent

Bhgre Gaetano Marra Homes

Broker

donna.bannon1002@gmail.com

Email

Affordability Calculator

$6,235
Per Month
80%
20%
0%
Monthly Principal & Interest
$5,018
Monthly Property Taxes
$1,217
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3042522 Elementary School
3042695 Middle School
Pomperaug High School High School
Pricing History
DatePricePrice ChangeDescription
4/17/2026$815,000 Listed Price

Map


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245 Upper Whittemore Road, Middlebury, CT, 06762 is a Single Family Home for sale at $815,000 with 2,990 sqft and a lot size of 3.03. 245 Upper Whittemore Road has 3 bedrooms, 2.1 baths, and was built in 2005. The property's zip code is 06762 which is in Middlebury, CT