245 Upper Whittemore Road

Closed 6/15/26Virtual Tour
Closed 6/15/26Virtual Tour
Gallery Image 1
Sold
Last Sold Price
$875,000
3 beds2,990 sqft$293/sqft
245 Upper Whittemore Rd, Middlebury, CT 06762
Single FamilyProperty Type
3.03 acresLot Size
2005Year Built
$293/sq ftPrice per sq ft
8 carsParking Spaces

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,...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.
  • Listed by: Donna Bannon 203.233.7499 donna.bannon1002@gmail.com • BHGRE Gaetano Marra Homes
Listing closed: 06/15/2026 12:00 AM • Source: SMARTMLS, MLS#: 24167463
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Location

Listing Courtesy of BHGRE Gaetano Marra Homes, Donna Bannon

Sold By Drakeley Real Estate, Inc., Shelley Drakeley

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$5,665 per month

30 year fixed, 6.55% Interest

Principal and Interest

$4,448

Property Taxes

$1,217

HOA Dues

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Property Information for 245 Upper Whittemore Road

Property Details
  • Taxes: $14,608 / year
  • MLS Type: Residential
  • County: New Haven County
  • Basement Description: Full, Full With Walk-Out
  • Direct Waterfront: No
  • Expected Active Date: 04-20-2026
  • Garages Number: 3
  • Style: Cape Cod
  • Garage Parking Info: Attached Garage, Under House Garage, Driveway
  • Swimming Pool: Yes
  • Expected On Market Date: 04-20-2026
Building Information
  • Year Built: 2005
  • Lot Size: 3.03 AC / 131,986 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Route 64 to Upper Whittemore or Middlebury Road to Charcoal Ave to Tranquility Road to Upper Whittemore.
  • Elementary School: Long Meadow
  • Flood Zone: No
  • High School: Pomperaug
  • Latitude: 41.529515
  • Longitude: -73.138748
  • Middle Jr High School: Memorial
  • Neighborhood Amenities: Bocci Court, Golf Course, Lake, Library, Medical Facilities, Park, Tennis Courts
  • State: Connecticut
Parking
  • Parking Total Spaces: 8
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $14,608
Interior and Exterior Features
Exterior Features
  • Exterior Features: Underground Utilities, Sidewalk, Gutters, Underground Sprinkler, Patio
  • Pool Description: Heated, Vinyl, Salt Water, In Ground Pool
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Electric Dryer
  • Attic Description: Walk-In
  • Cooling System: Central Air
  • Heat Type: Hydro Air
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Interior Features: Auto Garage Door Opener, Cable - Available, Central Vacuum, Security System
  • Laundry Room Info: Main Level
  • Laundry Room Location: Main level
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Bay/Bow Window,Breakfast Bar,Built-In Hutch,Granite Counters,Dining Area,Hardwood Floor
  • Room Length: 24.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 14.0
Room 2
  • Room Entry Order: 2
  • Room Features: 9 ft+ Ceilings,Gas Log Fireplace,Hardwood Floor
  • Room Length: 23.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 20.0
Room 3
  • Room Entry Order: 3
  • Room Length: 14.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 12.0
Room 4
  • Room Entry Order: 4
  • Room Features: 9 ft+ Ceilings
  • Room Length: 12.0
  • Room Level: Main
  • Room Type: Office
  • Room Width: 12.0
Room 5
  • Listing Key: 4F83573FE37173C2E063E201100A11D1
  • Room Entry Order: 5
  • Room Features: 9 ft+ Ceilings,Full Bath,Hardwood Floor
  • Room Length: 18.0
  • Room Level: Main
  • Room Type: Primary Bedroom
  • Room Width: 15.0
Room 6
  • Room Entry Order: 6
  • Room Features: Hardwood Floor
  • Room Length: 16.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 7
  • Room Entry Order: 7
  • Room Features: Hardwood Floor
  • Room Length: 19.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 8
  • Room Entry Order: 8
  • Room Features: Wall/Wall Carpet
  • Room Length: 18.0
  • Room Level: Upper
  • Room Type: Other
  • Room Width: 13.0
Property
Property and Assessments
  • Color: tan
  • Construction Description: Frame
  • Driveway Type: Paved
  • Exterior Siding: Shake
  • Foundation Type: Concrete
  • Fuel Tank Location: In Ground
  • Handicap Features: Bath Grab Bars, Lever Door Handles
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 2005
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: First Floor, Second Floor
  • In Law Apartment: Possible
  • Living Area SQFT Per Public Records: 2990
Lot Information
  • Lot Description: Professionally Landscaped
  • Parcel Number: 1192081
  • Sq Ft Est Heated Above Grade: 2990.0
  • Sq Ft Total: 2990.0
  • Zoning: R40
Utilities
  • Energy Features: Generator, Ridge Vents, Thermopane Windows
  • Heat Fuel Type: Propane
  • Hot Water Description: Propane, Domestic
  • Radon Mitigation Air: Yes
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 245 Upper Whittemore Road

DateEvent & SourcePriceAppreciation
Jun 10, 2026

Closed (Public Record)

Public Record #1943334876

$875,000

+8.9% / yr

Mar 12, 2004

Closed (Public Record)

Public Record #134210179

$130,000—
DateEvent & SourcePrice
06/10/2026

Closed (Public Record)

Public Record #1943334876

$875,000

+8.9% / yr

03/12/2004

Closed (Public Record)

Public Record #134210179

$130,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 245 Upper Whittemore Road

Taxable ValueLand$88,700Additions$360,500Total$449,200
Tax Record2025$14,608 ($1,217 / month)
Home Facts
Beds3Baths2.5Total Finished SqFt2,990 SqFtAbove Grade Finished SqFt2,990 SqFtUnfinished Basement SqFt2,018 SqFtStories2Lot Size131,987 SqFtStyleSingle Family ResidenceYear Built2005Year Renovated2005ZoningR40CountyNAUGATUCK VALLEYAPNMDBY M:7-08 L:038

Schools near 245 Upper Whittemore Road

This home is within Regional School District 15.
Rating
School
Type
Grades
Distance
Long Meadow Elementary School
Public - PK to 5
Memorial Middle School
Public - 6 to 8
Pomperaug Regional High School
Public - 9 to 12
Westover School
Private - 9 to 12
Rating
School
Distance
Long Meadow Elementary School
PublicPK to 5

Memorial Middle School
Public6 to 8

Pomperaug Regional High School
Public9 to 12

Westover School
Private9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of BHGRE Gaetano Marra Homes, Donna Bannon

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.