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.
Sold for $875,000
$875,000
245 Upper Whittemore Road, Middlebury, CT 06762
3beds
2,990sqft
Single Family Residence
Built in 2005
3.03 Acres Lot
$834,800 Zestimate®
$293/sqft
$5,542 Estimated rent
Home value
$834,800
$793,000 - $877,000
$5,542/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
Donna Bannon (203)233-7499,
BHGRE Gaetano Marra Homes 203-758-1300
Bought with:
Shelley Drakeley, RES.0790749
Drakeley Real Estate, Inc.
Source: Smart MLS,MLS#: 24167463
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Features: High Ceilings, Full Bath, Hardwood Floor
- Level: Main
- Area: 270 Square Feet
- Dimensions: 15 x 18
Bedroom
- Features: Hardwood Floor
- Level: Upper
- Area: 228 Square Feet
- Dimensions: 12 x 19
Bedroom
- Features: Hardwood Floor
- Level: Upper
- Area: 192 Square Feet
- Dimensions: 12 x 16
Dining room
- Level: Main
- Area: 168 Square Feet
- Dimensions: 12 x 14
Family room
- Features: High Ceilings, Gas Log Fireplace, Hardwood Floor
- Level: Main
- Area: 460 Square Feet
- Dimensions: 20 x 23
Kitchen
- Features: Bay/Bow Window, Breakfast Bar, Built-in Features, Granite Counters, Dining Area, Hardwood Floor
- Level: Main
- Area: 336 Square Feet
- Dimensions: 14 x 24
Office
- Features: High Ceilings
- Level: Main
- Area: 144 Square Feet
- Dimensions: 12 x 12
Other
- Features: Wall/Wall Carpet
- Level: Upper
- Area: 234 Square Feet
- Dimensions: 13 x 18
Heating
- Hydro Air, Propane
Cooling
- Central Air
Appliances
- Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Main Level
Features
- Central Vacuum
- Windows: Thermopane Windows
- Basement: Full
- Number of fireplaces: 1
Interior area
- Total structure area: 2,990
- Total interior livable area: 2,990 sqft
- Finished area above ground: 2,990
Property
Parking
- Total spaces: 8
- Parking features: Attached, Driveway, Garage Door Opener, Paved
- Attached garage spaces: 3
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: Bath Grab Bars, Lever Door Handles
Features
- Patio & porch: Patio
- Exterior features: Sidewalk, Rain Gutters, Underground Sprinkler
- Has private pool: Yes
- Pool features: Heated, Vinyl, Salt Water, In Ground
Lot
- Size: 3.03 Acres
- Features: Landscaped
Details
- Parcel number: 1192081
- Zoning: R40
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod
- Property subtype: Single Family Residence
Materials
- Shake Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 2005
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Underground Utilities, Cable Available
Green energy
- Energy efficient items: Ridge Vents, Windows
Community & neighborhood
Security
- Security features: Security System
Community
- Community features: Bocci Court, Golf, Lake, Library, Medical Facilities, Park, Tennis Court(s)
Location
- Region: Middlebury
Price history
| Date | Event | Price |
|---|---|---|
| 6/15/2026 | Sold | $875,000+7.4%$293/sqft |
Source:  Smart MLS #24167463 Report a problem | ||
| 4/21/2026 | Pending sale | $815,000$273/sqft |
Source: Smart MLS #24167463 Report a problem | ||
| 4/20/2026 | Listed for sale | $815,000+526.9%$273/sqft |
Source: Smart MLS #24167463 Report a problem | ||
| 3/12/2004 | Sold | $130,000$43/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $14,608 -0.2% | $449,200 |
| 2024 | $14,644 +1.1% | $449,200 |
| 2023 | $14,491 +3.2% | $449,200 |
| 2022 | $14,042 +20.1% | $449,200 +33.8% |
| 2021 | $11,692 -0.8% | $335,700 |
| 2020 | $11,783 +5.1% | $335,700 |
| 2019 | $11,212 +2.7% | $335,700 |
| 2018 | $10,914 +3.2% | $335,700 |
| 2017 | $10,571 +0.1% | $335,700 -4.2% |
| 2015 | $10,560 +2.7% | $350,600 |
| 2014 | $10,287 +1.7% | $350,600 |
| 2013 | $10,118 +2.8% | $350,600 |
| 2012 | $9,841 -8.9% | $350,600 -22.8% |
| 2011 | $10,805 +0.7% | $454,200 |
| 2009 | $10,733 +1.8% | $454,200 |
| 2008 | $10,542 +6% | $454,200 |
| 2007 | $9,947 +221.9% | $454,200 +349.1% |
| 2005 | $3,090 +51.7% | $101,140 +53.1% |
| 2004 | $2,037 | $66,080 |
Find assessor info on the county website
Neighborhood: 06762
Nearby schools
GreatSchools rating
- 5/10Long Meadow Elementary SchoolGrades: PK-5Distance: 1.9 mi
- 8/10Memorial Middle SchoolGrades: 6-8Distance: 2.6 mi
- 8/10Pomperaug Regional High SchoolGrades: 9-12Distance: 2.3 mi
Schools provided by the listing agent
- Elementary: Long Meadow
- Middle: Memorial
- High: Pomperaug
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Connecticut
- New Haven County
- Middlebury
- 06762
- 245 Upper Whittemore Road
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