283 Whittemore Road

Closed 6/18/26
Closed 6/18/26
Gallery Image 1
Last Sold Price
$500,000
3 beds2,500 sqft$200/sqft
283 Whittemore Rd, Middlebury, CT 06762

Description

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,...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, New Furnace (2024), 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).
LISTING CLOSED: 06/18/2026 12:00 AM

  1. Listed by Jennifer Sisco • RE/MAX Heritage
    P: (203) 417-5764 C: (203) 417-5764 jenrheritage@gmail.com

Property Details for 283 Whittemore Road

Status
Closed
MLS #
24169230
Days on Market
24
Taxes
$6,159 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
Single Family
MLS Type
Residential
Year Built
1972
Lot Size
0.39 AC / 16,988 SF
County
New Haven County
Basement Description
Full, Heated, Fully Finished, Garage Access, Interior Access, Liveable Space, Full With Walk-Out
Direct Waterfront
No
Expected Active Date
04-30-2026
Garages Number
2
Neighborhood
N/A
Style
Raised Ranch
Garage Parking Info
Attached Garage
Swimming Pool
No
Expected On Market Date
04-30-2026
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Location

Listing Courtesy of RE/MAX Heritage, Jennifer Sisco

Sold By Better Living Realty, LLC, Rob Marucci

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Building Information for 283 Whittemore Road

Stories-Year Built1972Building Size-Lot Size0.39 AC / 16,988 SF

Payment Calculator

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$3,055 per month

30 year fixed, 6.55% Interest

Principal and Interest

$2,541

Property Taxes

$513

HOA Dues

$0

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Property Information for 283 Whittemore Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: I-84 to Straits Tpk, to Whittemore Rd. Turn onto Shadduck Rd. Driveway is on Shadduck.
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Latitude: 41.526723
  • Longitude: -73.090897
  • Neighborhood Amenities: Golf Course, Lake, Medical Facilities, Park, Playground/Tot Lot, Public Rec Facilities, Public Transportation, Shopping/Mall
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $6,159
Interior and Exterior Features
Exterior Features
  • Exterior Features: Shed, Porch, Deck, Garden Area, Lighting, Patio
  • Waterfront Description: Walk to Water, Access
Interior Features
  • Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Pull-Down Stairs
  • Cooling System: Window Unit
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Laundry Room Info: Lower Level
  • Rooms Total: 6
Room 1
  • Room Entry Order: 1
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Features: Balcony/Deck,Sliders
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Features: Ceiling Fan,Half Bath
  • Room Level: Main
  • Room Type: Primary BR Suite
Room 4
  • Room Entry Order: 4
  • Room Features: Ceiling Fan
  • Room Level: Main
  • Room Type: Bedroom
Room 5
  • Listing Key: 500AE76CCD823CB1E0631A01100AE239
  • Room Entry Order: 5
  • Room Features: Remodeled,Ceiling Fan
  • Room Level: Lower
  • Room Type: Bedroom
Room 6
  • Room Entry Order: 6
  • Room Features: Remodeled,Gas Log Fireplace,Full Bath,Sliders
  • Room Level: Lower
  • Room Type: Rec/Play Room
Property
Property and Assessments
  • Construction Description: Frame
  • Exclusions: Per Inclusions/Exclusions Addendum
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Concrete
  • Fuel Tank Location: In Garage
  • Handicap Features: Accessible Bath, Bath Grab Bars, Multiple Entries/Exits
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1972
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Lower Level
  • In Law Apartment: Possible
  • Sq Ft Est Heated Below Grade: 1200
  • Living Area SQFT Per Public Records: 1300
Lot Information
  • Lot Description: Corner Lot, Level Lot
  • Parcel Number: 1193292
  • Sq Ft Est Heated Above Grade: 1300.0
  • Sq Ft Total: 2500.0
  • Zoning: R40
Utilities
  • Energy Features: Generator Ready
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Tankless Hotwater
  • Sewage System: Public Sewer Connected
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 283 Whittemore Road

DateEvent & SourcePriceAppreciation
Jun 18, 2026

Closed (Public Record)

Public Record #1943334834

$500,000

+5.4% / yr

Feb 13, 2013

Closed (Public Record)

Public Record #348061146

$247,500—
DateEvent & SourcePrice
06/18/2026

Closed (Public Record)

Public Record #1943334834

$500,000

+5.4% / yr

02/13/2013

Closed (Public Record)

Public Record #348061146

$247,500

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

Public Records for 283 Whittemore Road

Taxable ValueLand$55,100Additions$134,300Total$189,400
Tax Record2025$6,159 ($513 / month)
Home Facts
Beds3Baths1.5Total Finished SqFt1,300 SqFtAbove Grade Finished SqFt1,300 SqFtUnfinished Basement SqFt576 SqFtStories1Lot Size16,988 SqFtStyleSingle Family ResidenceYear Built1972Year Renovated1972ZoningR40CountyNAUGATUCK VALLEYAPNMDBY M:4-06 L:463

Schools near 283 Whittemore Road

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

Memorial Middle School
Public6 to 8

Pomperaug Regional High School
Public9 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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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 283 Whittemore Road, Middlebury, CT 06762
$500,000
3
2,500
16,988
22 Shadduck Road, Middlebury, CT 06762
$405,000
4
2,978
49,658
27 Shadduck Road, Middlebury, CT 06762
$90,000
2
1,083
0
36 Shadduck Road, Middlebury, CT 06762
$40,000
2
854
0
286 Whittemore Road, Middlebury, CT 06762
–
–
–
18,884
366,340
40 Shadduck Road, Middlebury, CT 06762
$223,000
4
1,248
91,040

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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 RE/MAX Heritage, Jennifer Sisco

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.