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$875,000

  • Sold
  • Closed
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,990 Sq. Ft.
  • 3 Car Garage
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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 for 245 Upper Whittemore Rd

General

  • Sold For: $875,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24167463
  • Added to Site: 96 day(s) ago

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
Sold by Drakeley Real Estate, Inc., Shelley Drakeley

Listing agent

— 245 Upper Whittemore Rd —

  • Donna Bannon

    BHGRE Gaetano Marra Homes

Agent Contact: (203) 233-7499 Office Contact: (203) 758-1300

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 245 Upper Whittemore Rd

School District:Regional School District 15
NameGradesDistance
Long Meadow Elementary School
65 North Benson Road, Middlebury, CT 06762
PK-51.9 mi
Memorial Middle School, Middlebury, CT
1 Memorial Drive, Middlebury, CT 06762
6-82.5 mi
Pomperaug Regional High School
234 Judd Road, Southbury, CT 06488
9-122.3 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

Date
Details
Price
Change
Source
6/15/2026
Sold
$875,000
7.36%
MLS
4/20/2026
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.

Listed by BHGRE Gaetano Marra Homes, Donna Bannon
Sold by Drakeley Real Estate, Inc., Shelley Drakeley

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245 Upper Whittemore Road, Middlebury, CT 06762 (MLS# 24167463) is a Single Family property that was sold at $875,000 on June 15, 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.