About 245 Upper Whittemore Road
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.
Features of 245 Upper Whittemore Road
| MLS® # | 24167463 |
|---|---|
| Price | $875,000 |
| Bedrooms | 3 |
| Bathrooms | 2/1 |
| Full Baths | 2 |
| Half Baths | 1 |
| Square Footage | 2,990 |
| Acres | 3.03 |
| Type | Single Family For Sale |
| Style | Cape Cod |
| Status | Closed |
Community Information
| Address | 245 Upper Whittemore Road |
|---|---|
| Area | N/A |
| City | Middlebury |
| County | New Haven |
| State | Connecticut |
| Zip Code | 06762 |
Amenities
| Features | Generator, Ridge Vents, Thermopane Windows |
|---|---|
| Parking Spaces | 8 |
| Parking | Attached Garage, Under House Garage, Driveway |
| Garage Spaces | 3 |
| Is Waterfront | No |
| Waterfront | Not Applicable |
| Has Pool | Yes |
| Pool | Heated, Vinyl, Salt Water, In Ground Pool |
Interior
| Interior Features | Auto Garage Door Opener, Cable - Available, Central Vacuum, Security System |
|---|---|
| Appliances | Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Electric Dryer |
| Heating | Hydro Air, Propane |
| Cooling | Central Air |
| Fireplace | Yes |
| # of Fireplaces | 1 |
Exterior
| Exterior | Shake |
|---|---|
| Exterior Features | Underground Utilities, Sidewalk, Gutters, Underground Sprinkler, Patio |
| Lot Description | Professionally Landscaped |
| Roof | Asphalt Shingle |
| Foundation | Concrete |
School Information
| Elementary | Long Meadow |
|---|---|
| Middle | Memorial |
| High | Pomperaug |
Additional Information
| Date Listed | April 17th, 2026 |
|---|---|
| Days on Market | 1 |
| Zoning | R40 |
| RE / Bank Owned | No |
Listing Details
| Office | BHGRE Gaetano Marra Homes |
|---|
