This home's estimate is 20.6% higher than the average sale price ($722K) of 6 comparable homes.
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245 Upper Whittemore Rd, Middlebury, CT 06762
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About this home
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.
Redfin Estimate
Market trends in 06762, CT
Last updated August 2026
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Est. $3,429 per month, based on comparable rentals
Sale and tax history for 245 Upper Whittemore Rd
- Sale History
- Tax History
$293/sq ft
$273/sq ft
$273/sq ft
$43/sq ft
Public record
Property details
Parking
- Garage Information
- Garage & Parking: Attached Garage, Under House Garage, Driveway
- Garages Number: 3
- Parking Information
- Parking Total Spaces: 8
Interior
- Virtual Tour Information
- Interior Information
- Total Rooms: 8
- Laundry Room Location: Main level
- Laundry Room Info: Main Level
- Interior Features: Auto Garage Door Opener, Cable - Available, Central Vacuum, Security System
- In-Law Apartment: Possible
- In-Law Access: First Floor, Second Floor
- Handicap Features: Bath Grab Bars, Lever Door Handles
- Fireplaces Total: 1
- Cooling System: Central Air
- Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Electric Dryer
- Bathroom Information
- # of Baths (Full): 2
- # of Baths (Half): 1
- Bedroom Information
- Beds Total: 3
- Room Information
- Basement Description: Full, Full With Walk-Out
- Has Attic
Exterior
- Exterior Features
- Roof Information: Asphalt Shingle
- Exterior Siding: Shake
- Exterior Features: Underground Utilities, Sidewalk, Gutters, Underground Sprinkler, Patio
- Lot Information
- Lot Description: Professionally Landscaped
- Pool Information
- Swimming Pool
- Pool Description: Heated, Vinyl, Salt Water, In Ground Pool
- Building Information
- Foundation Type: Concrete
- Construction Description: Frame
- Color: tan
- Property Information
- Radon Mitigation Air
- Property Type: Single Family For Sale
- Living Area SQFT Per Public Record: 2990
- Driveway Type: Paved
Financial
- Assessments Information
- Assessed Value: $449,200
Utilities
- Utility Information
- Water Source: Private Well
- Sewage System: Septic
- Hot Water Description: Propane, Domestic
- Heat Type: Hydro Air
- Heat Fuel Type: Propane
- Fuel Tank Location: In Ground
- Energy Features: Generator, Ridge Vents, Thermopane Windows
Location
- School Information
- Middle Jr High School: Memorial
- High School: Pomperaug
- Elementary School: Long Meadow
- Location Information
- State: Connecticut
- Nearby Amenities: Bocci Court, Golf Course, Lake, Library, Medical Facilities, Park, Tennis Courts
- Directions: Route 64 to Upper Whittemore or Middlebury Road to Charcoal Ave to Tranquility Road to Upper Whittemore.
- County: New Haven
Public facts
- Beds: 3
- Baths: 2.5
- Sq. Ft.: 2,990
- Stories: 2.0
- Lot Size: 3.03 acres
- Style: Single Family Residential
- Year Built: 2005
- Year Renovated: —
- County: New Haven County
- APN: 1192081
Other
- Documents & Disclosures
- Supplement Count Public: 1
Around this home
Schools
Public PreK-5 • Assigned • 1.9mi
Public 6-8 • Assigned • 2.6mi
Public 9-12 • Assigned • 2.2mi
Climate risks
Minimal risk of a flood reaching the building in the next 30 years
Unlikely to be in a wildfire in next 30 years
7 days above 97° expected this year, 15 days in 30 years
25% chance of strong winds in next 30 years
2 unhealthy days expected this year, 4 days in 30 years
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.
Nearby similar homes
New listings for sale in 06762
Home values near 245 Upper Whittemore Rd
| Address | Redfin Estimate |
|---|---|
4 Beds | 3 Baths | 3928 Sq. Ft. | $1,522,102 |
5 Beds | 4.5 Baths | 7669 Sq. Ft. | $1,468,873 |
| Address | Redfin Estimate |
|---|---|
4 Beds | 4.5 Baths | 4555 Sq. Ft. | $1,102,835 |
3 Beds | 3.5 Baths | 5292 Sq. Ft. | $892,913 |
| Address | Redfin Estimate |
|---|---|
3 Beds | 1.5 Baths | 1636 Sq. Ft. | $552,365 |
4 Beds | 2.5 Baths | 4349 Sq. Ft. | $971,337 |
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