Date
Details
Price
Change
Source
4/16/2026
Listed
$815,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/29
$815,000 Coming Soon
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1/29
Property Description
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.
Full Property Details
Full Property Details for 245 Upper Whittemore Rd
General
- Price: $815,000
- Taxes: (July 2025-June 2026)
- Status: Coming Soon
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24167463
- Updated: 4/17/2026
- Added to Site: 2 day(s) ago
- Expected Market Date: 4/20/2026
Interior
- Number of Rooms: 8
- Interior Features: Auto Garage Door Opener, Cable - Available, Central Vacuum, Security System
- Fireplace: Yes
- Number of Fireplaces: 1
- Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Electric Dryer
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 3
- Primary Bedroom: Primary Bedroom - 9 ft+ Ceilings, Full Bath, Hardwood Floor, 18 x 15, Main
- Bedroom 1: Bedroom - Hardwood Floor, 16 x 12, Upper
- Bedroom 2: Bedroom - Hardwood Floor, 19 x 12, Upper
Other Rooms
- Family Room: Family Room - 9 ft+ Ceilings, Gas Log Fireplace, Hardwood Floor, 23 x 20, Main
- Kitchen: Kitchen - Bay/Bow Window, Breakfast Bar, Built-In Hutch, Granite Counters, Dining Area, Hardwood Floor, 24 x 14, Main
- Dining Room: Dining Room, 14 x 12, Main
- Office: Office - 9 ft+ Ceilings, 12 x 12, Main
- Laundry: Main Level
- Other Room 1: Other - Wall/Wall Carpet, 18 x 13, Upper
Additional Information
- Pool: Yes
- Pool Description: Heated, Vinyl, Salt Water, In Ground Pool
Exterior
- Exterior Features: Underground Utilities, Sidewalk, Gutters, Underground Sprinkler, Patio
- Color: tan
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Total Spaces: 8
- Parking: Attached Garage, Under House Garage, Driveway
Location
- County: New Haven
- Driving Directions: Route 64 to Upper Whittemore or Middlebury Road to Charcoal Ave to Tranquility Road to Upper Whittemore.
School Information
- Elementary School: Long Meadow
- Middle School: Memorial
- High School: Pomperaug
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Hydro Air, Propane
- Heating Fuel: Propane
- Water Heater: Propane, Domestic
Utilities
- Sewer: Septic
- Water: Private Well
Structural Information
- Architectural Style: Cape Cod
- Construction Status: No/Resale
- Exterior Const.: Shake
- Basement Desc.: Full, Full With Walk-Out
- Roof: Asphalt Shingle
- Attic: Yes
- Disability Access: Bath Grab Bars, Lever Door Handles
- Square Feet: 2,990
- Above Ground: 2,990 Sq. Ft.
- Year Built: 2005
Lot Features
- Lot Size (Acres): 3.03
- Driveway/Sidewalk: Paved
- Zoning: R40
- Lot Description: Professionally Landscaped
Green Features
- Energy Features: Generator, Ridge Vents, Thermopane Windows
Financial Considerations
- Assessment Amount: $449,200
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 1192081
Listed by BHGRE Gaetano Marra Homes, Donna Bannon
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 245 Upper Whittemore Rd —
Donna Bannon
BHGRE Gaetano Marra Homes
Agent Contact: (203) 233-7499 Office Contact: (203) 758-1300
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 245 Upper Whittemore Rd
School District:Regional School District 15
| Name | Grades | Distance |
|---|---|---|
Long Meadow Elementary School 65 North Benson Road, Middlebury, CT 06762 | PK-5 | 1.9 mi |
Memorial Middle School, Middlebury, CT 1 Memorial Drive, Middlebury, CT 06762 | 6-8 | 2.5 mi |
Pomperaug Regional High School 234 Judd Road, Southbury, CT 06488 | 9-12 | 2.3 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 245 Upper Whittemore Rd
Tax History
Tax History for 245 Upper Whittemore Rd
Year
Property Taxes
Change
Tax Assessment
Change
2025
$14,608
—
$449,200
—
2023
$14,644
1%
$449,200
—
2023
$14,491
3%
$449,200
—
2022
$14,042
20%
$449,200
34%
2021
$11,692
-1%
$335,700
—
2020
$11,783
5%
$335,700
—
2019
$11,212
3%
$335,700
—
2018
$10,914
3%
$335,700
—
2017
$10,571
-3%
$335,700
-4%
2016
$10,872
3%
$350,600
—
2015
$10,560
3%
$350,600
—
2014
$10,287
2%
$350,600
—
2011
$10,118
—
$350,600
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 245 Upper Whittemore Rd
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- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 4Total Baths
- 4,094Sq. Ft.
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- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 2Total Baths
- 1,040Sq. Ft.
- Single Family
- Active
- Updated 2 days ago
- 1Bed
- 1Total Bath
- 696Sq. Ft.
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- Single Family
- Active
- Updated 2 days ago
- 4Beds
- 1Total Bath
- 1,287Sq. Ft.
- Single Family
- Active
- Updated 4 days ago
- 3Beds
- 1Total Bath
- 1,296Sq. Ft.
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245 Upper Whittemore Road, Middlebury, CT 06762 (MLS# 24167463) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 245 Upper Whittemore Road is currently listed for $815,000 and was received on April 16, 2026. Want to learn more about 245 Upper Whittemore Road? Do you have questions about finding other Single Family real estate for sale in Middlebury? You can browse all Middlebury real estate or contact a Coldwell Banker agent to request more information.