103 Whittemore Rd, Middlebury, CT 06762
OFF MARKET

103 Whittemore Rd
Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,097 sqft (on 1.45 acres)

$448,500

Trulia Estimate
as of Apr 29, 2026
Est. Refi. Payment $3,069/mo*

$448,500

Trulia Estimate
as of Apr 29, 2026
Est. Refi. Payment $3,069/mo*
3 Beds
2.5 Baths
2,097 sqft
(on 1.45 acres)

Homes for sale near 103 Whittemore Rd

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Apartments for Rent

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Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Updated 3 bedroom 2.5 bath split level home in perfect commuting location. Wonderful open concept living. Kitchen with stainless steel appliances, granite counter, and newer cabinets. Living room/Dining room with hardwood floors and fireplace. Sunken sunroom with sliders to backyard. Perfect layout for entertaining. Upper level boasts master bedroom with full bath. Two other bedrooms have hardwood flooring. Lower level family room has fireplace and half bath. Newer boiler, windows, pex piping, and much more. Welcome home! NEW ROOF JANUARY 2021! A/C âas isâ.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 103 Whittemore Rd

Interior Features

Heating & Cooling
Heating: Baseboard, OilAir ConditioningHeating Fuel: Baseboard
Interior Details
Number of Rooms: 6Types of Rooms: Laundry Room
Appliances & Utilities
DishwasherRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: OtherPatio
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1950
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 1.45 acres

Price History for 103 Whittemore Rd

DatePriceEventSource
03/19/2021$285,000Sold
Smart MLS #170368027
01/25/2021$275,000Listed For SaleAgent Provided
01/15/2021ListingRemovedKeller Williams
12/30/2020$260,000PendingToActiveKeller Williams #170322482
11/18/2020$260,000PendingAgent Provided
10/27/2020$260,000PriceChange
Agent Provided
10/02/2020$267,000PriceChange
Agent Provided
09/12/2020$275,000PendingToActiveAgent Provided
09/01/2020$275,000PendingAgent Provided
07/31/2020$275,000Listed For SaleAgent Provided
08/15/2016$151,000Sold
N/A
07/23/2003$255,000Sold
Smart MLS #W1010768
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Property Tax and Assessment

Year2025
Tax$7,444
Assessment$228,900
Home facts updated by county records

Comparable Sales for 103 Whittemore Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.29
Single-Family Home
$499,900
08/26/25
3
2.5
2,360
0.25
Single-Family Home
$385,000
09/29/25
3
1
1,630
0.34
Single-Family Home
$435,000
10/14/25
3
3.5
1,596
0.34
Single-Family Home
$485,000
08/20/25
3
2
2,534
0.53
Single-Family Home
$400,000
12/22/25
5
2
2,023
0.52
Single-Family Home
$515,000
02/27/26
4
2.5
2,260
0.51
Single-Family Home
$550,000
11/14/25
4
2.5
2,400
0.63
Single-Family Home
$495,000
12/04/25
3
2.5
2,311
0.71
Single-Family Home
$449,900
11/19/25
2
2.5
1,744
0.86
Single-Family Home
$680,000
06/16/25
4
3
2,860

Assigned Schools

These are the assigned schools for 103 Whittemore Rd.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Middlebury

At least 21 Trulia users voted on each feature.
  • 94 % Say yards are well-kept

  • 93 % Say parking is easy

  • 86 % Say car is needed

  • 82 % Say there's holiday spirit

  • 78 % Say there's wildlife

  • 72 % Say it's quiet

  • 63 % Say it's dog friendly

  • 58 % Say people would walk alone at night

  • 52 % Say kids play outside

  • 48 % Say they plan to stay for at least 5 years

  • 47 % Say neighbors are friendly

  • 45 % Say it's walkable to restaurants

  • 36 % Say streets are well-lit

  • 35 % Say there are sidewalks

  • 34 % Say there are community events

  • 27 % Say it's walkable to grocery stores

Learn more about our methodology.
  • Ginacea313@gmail.com
    "It’s a beautiful community with little to no crime. There is a crystal clear lake and a small amusement park. Additionally, there are plenty of hiking trails. Autumn is quite amazing here, with many vibrant colors. "
  • Ginacea313@gmail.com
    "Middlebury is a beautiful town. It is truly a New England gem. Lake Quassapaug is clean and the MRA is well kept. Summers are heavenly here. "
  • Plandusky
    "Region 15 public schools are some of the best in the state. Middlebury, Southbury public schools. Safe neighborhoods lived here 27 years and could have left the car unlocked the whole time"
  • Cadecres
    "I’ve lived here 11 years now and everyone is friendly and thoughtful. This town is a hidden gem, just far enough away from the bustle yet close enough not to be isolated."
  • darrenwittko
    "With excellent schools and beautiful parks, Middlebury is the perfect family community. Close to I-84, it's great for commuters too."
  • Donathom1114
    "This is an excellent community for families. Top notch schools with excellent family activities. Private community with walking trails and child and pet friendly streets. Wonderful neighbors and pride of home ownership,"
  • castaway45
    "I grew up here, moved here when I was 9. Many fond memories. Great place to walk and for recreation, and for kids to play, points were neighbors, community spirit, natural setting."
  • Rtfa50
    "Great neighborhood for a family with children. Close proximity to I-84 both east and westbound. Excellent area for biking, hiking and walking. Easy access to neighboring towns such as Woodbury, Southbury and easy commute for professionals working in both Waterbury or Danbury. "
  • Hallie
    "I have lived here for 10 years and would not live anywhere else. The schools are fantastic, the parks beautiful, and the town beach perfect. Everywhere you look are flowers, towering oaks, and wonderful jogging paths. This is quintessential New England."

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Homes for rent near 103 Whittemore Rd

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Off Market Homes Near 103 Whittemore Rd

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103 Whittemore Rd, Middlebury, CT 06762 is a 3 bedroom, 3 bathroom, 2,097 sqft single-family home built in 1950. This property is not currently available for sale. 103 Whittemore Rd was last sold on Mar 19, 2021 for $285,000. The current Trulia Estimate for 103 Whittemore Rd is $448,500.