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$529,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,500 Sq. Ft.
  • 2 Car Garage
  • Updated 5 hours ago

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Open House: 11:00 AM - 1:00 PM

Saturday 5/2 11:00 AM - 1:00 PM

283 Whittemore Road,Middlebury, CT 06762

283 Whittemore RoadMiddleburyCT06762

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Thoughtful updates, versatile living space, and an unbeatable location come together at this gorgeous, meticulously maintained Middlebury home which offers the perfect blend of comfort and functionality and a layout designed for both everyday living and gracious entertaining. Freshly painted throughout, the home feels bright, clean, and move-in ready from the moment you step inside. The heart of the home flows from the kitchen and dining area out to a spacious bi-level deck, overlooking a large, flat backyard, ideal for gatherings, play, or simply enjoying peaceful time outdoors. A lovely lower patio creates an additional outdoor living space that feels like your own private retreat. Downstairs, the recently renovated lower level adds exceptional value and flexibility. Finished with upscale touches, this space features a comfortable living area with a luxurious fireplace, a private bedroom, full bathroom, and direct access to both the oversized 2-car garage and the backyard patio through sliding doors. Practical upgrades provide peace of mind and long-term efficiency, including: New roof and leaf guards (2020), Upgraded 200-amp electrical service, Generator hookup (2020), New double-wall 300-gallon oil tank (2020), New well pump and water softener (2025), and hot and cold water supply in garage (2025).

Full Property Details for 283 Whittemore Rd

General

  • Price: $529,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24169230
  • Updated: Today (4/30/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 6
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3
  • Primary Suite: Ceiling Fan, Half Bath, Main
  • Bedroom 1: Bedroom - Remodeled, Ceiling Fan, Lower
  • Bedroom 2: Bedroom - Ceiling Fan, Main

Other Rooms

  • Living Room: Living Room - Hardwood Floor, Main
  • Dining Room: Dining Room - Balcony/Deck, Sliders, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Remodeled, Gas Log Fireplace, Full Bath, Sliders, Lower
  • Rec Room: Remodeled, Gas Log Fireplace, Full Bath, Sliders, Lower
  • Laundry: Lower Level

Exterior

  • Exterior Features: Shed, Porch, Deck, Garden Area, Lighting, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: New Haven
  • Driving Directions: I-84 to Straits Tpk, to Whittemore Rd. Turn onto Shadduck Rd. Driveway is on Shadduck.

School Information

  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed

Heating & Cooling

  • Cooling Type: Window Unit
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Tankless Hotwater

Utilities

  • Sewer: Public Sewer Connected
  • Water: Private Well

Structural Information

  • Architectural Style: Raised Ranch
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Heated, Fully Finished, Garage Access, Interior Access, Liveable Space, Full With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Disability Access: Accessible Bath, Bath Grab Bars, Multiple Entries/Exits
  • Square Feet: 2,500
  • Above Ground: 1,300 Sq. Ft.
  • Below Ground: 1,200 Sq. Ft.
  • Year Built: 1972

Lot Features

  • Lot Size (Acres): 0.39
  • Zoning: R40
  • Lot Description: Corner Lot, Level Lot

Water Features

  • Water Front Desc.: Walk to Water, Access

Green Features

  • Energy Features: Generator Ready

Financial Considerations

  • Assessment Amount: $189,400
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: Per Inclusions/Exclusions Addendum
  • Property ID: 1193292

Listed by RE/MAX Heritage, Jennifer Sisco

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Listing agent

— 283 Whittemore Rd —

  • Jennifer Sisco

    RE/MAX Heritage

Agent Contact: (203) 417-5764 Office Contact: (203) 452-7653

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 283 Whittemore Rd

School District:Regional School District 15
NameGradesDistance
Middlebury Elementary School
550 Whittemore Road, Middlebury, CT 06762
K-50.5 mi
Memorial Middle School, Middlebury, CT
1 Memorial Drive, Middlebury, CT 06762
6-81.1 mi
Pomperaug Regional High School
234 Judd Road, Southbury, CT 06488
9-124 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 283 Whittemore Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/30/2026
Listed
$529,000
113.74%
MLS
2/13/2013
Sold
$247,500
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 283 Whittemore Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,159
—
$189,400
—
2023
$6,174
1%
$189,400
—
2023
$6,110
3%
$189,400
—
2022
$5,921
4%
$189,400
16%
2021
$5,684
-1%
$163,200
—
2020
$5,728
5%
$163,200
—
2019
$5,451
3%
$163,200
—
2018
$5,306
3%
$163,200
—
2017
$5,139
7%
$163,200
5%
2016
$4,797
3%
$154,700
—
2015
$4,660
3%
$154,700
—
2014
$4,539
2%
$154,700
—
2011
$4,465
—
$154,700
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 283 Whittemore Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by RE/MAX Heritage, Jennifer Sisco

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283 Whittemore Road, Middlebury, CT 06762 (MLS# 24169230) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 283 Whittemore Road is currently listed for $529,000 and was received on April 30, 2026. Want to learn more about 283 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.

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