Recently Viewed Properties
See This Home
Save This Listing
Close

$500,000

  • Sold
  • Closed
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,500 Sq. Ft.
  • 2 Car Garage
  • Updated 23 hours ago
See This Home
Save This Home
See This Home
Save This Home
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).

Full Property Details for 283 Whittemore Rd

General

  • Sold For: $500,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24169230
  • Added to Site: 53 day(s) ago

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
Sold by Better Living Realty, LLC, Rob Marucci

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

Date
Details
Price
Change
Source
6/18/2026
Sold
$500,000
-3.66%
MLS
5/14/2026
Price Reduced
$519,000
-1.89%
MLS
4/30/2026
Listed
$529,000
—
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 RE/MAX Heritage, Jennifer Sisco
Sold by Better Living Realty, LLC, Rob Marucci

Similar Properties near 283 Whittemore Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

130 Woodbine St, Naugatuck, CT 06770 - Photo 1
$485,000

130 Woodbine St  Naugatuck, CT 06770

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,965
    Sq. Ft.
Listed by Re/Max Rise
541 Middlebury Rd, Watertown, CT 06795 - Photo 1
$489,900

541 Middlebury Rd  Watertown, CT 06795

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 2,496
    Sq. Ft.
Listed by West View Properties, LLC
45 Adriatic Ln, Naugatuck, CT 06770 - Photo 1
$495,000

45 Adriatic Ln  Naugatuck, CT 06770

  • Single Family
  • Active
  • Updated 7 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,599
    Sq. Ft.
Listed by Keller Williams Realty Prtnrs.
169 Darcangelo Dr, Naugatuck, CT 06770 - Photo 1
$495,000

169 Darcangelo Dr  Naugatuck, CT 06770

  • Single Family
  • Active
  • Updated 7 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,599
    Sq. Ft.
Listed by Keller Williams Realty Prtnrs.

Just Listed near 283 Whittemore Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

45 Rockwell Ave, Waterbury, CT 06708 - Photo 1 Just Listed
$349,900

45 Rockwell Ave  Waterbury, CT 06708

  • Single Family
  • Active
  • Updated 18 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,352
    Sq. Ft.
Listed by Jessica Danard (203) 215-4180
336 Sylvan Ave, Waterbury, CT 06706 - Photo 1 Just Listed
$370,000

336 Sylvan Ave  Waterbury, CT 06706

  • Multi-Family
  • Active
  • Updated 10 hours ago
  • 5
    Total Beds
Listed by Stephanie Peraza (860) 294-3621
15 Howard St, Waterbury, CT 06705 - Photo 1 Just Listed
$450,000
Open House

15 Howard St  Waterbury, CT 06705

  • Multi-Family
  • Active
  • Updated 2 days ago
  • 7
    Total Beds
Listed by Mustafa Muaremi (860) 877-4682
17 Irene Ave, Waterbury, CT 06705 - Photo 1 Just Listed
$335,000
Open House

17 Irene Ave  Waterbury, CT 06705

  • Single Family
  • Active
  • Updated 18 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,827
    Sq. Ft.
Listed by Raelyn Lawrence (860) 921-3597

Price Reduced near 283 Whittemore Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

31 Winchester St, Waterbury, CT 06704 - Photo 1 Price Reduced
-$4,000 (-1.91%)
$205,000

31 Winchester St  Waterbury, CT 06704

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,414
    Sq. Ft.
Listed by Linda Lopez (860) 622-9063
496 Chase Ave, Waterbury, CT 06704 - Photo 1 Price Reduced
-$750 (-12.5%)
$5,250

496 Chase Ave  Waterbury, CT 06704

  • Commercial Lease
  • Active
Listed by Dave Jones Realty, LLC
34 Mitchell Ave, Waterbury, CT 06710 - Photo 1 Price Reduced
-$24,900 (-4.53%)
$525,000

34 Mitchell Ave  Waterbury, CT 06710

  • Multi-Family
  • Active
  • Updated 3 days ago
  • 14
    Total Beds
Listed by Coldwell Banker Calabro
2 S Meadows, Woodbury, CT 06798 - Photo 1 Price Reduced
-$30,250 (-8.01%)
$347,500

2 S Meadows  #2  Woodbury, CT 06798

  • Townhouse
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,069
    Sq. Ft.
Listed by Adams & Adams Real Estate

Recent Sales near 283 Whittemore Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

271 Shadduck Rd, Middlebury, CT 06762 - Photo 1 Sold
$435,000

271 Shadduck Rd  Middlebury, CT 06762

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,288
    Sq. Ft.
Listed by Houlihan Lawrence
Sold by William Raveis Real Estate
18 Freedom Rd, Middlebury, CT 06762 - Photo 1 Sold
$495,650

18 Freedom Rd  Middlebury, CT 06762

  • Single Family
  • Closed
  • Updated 8 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,492
    Sq. Ft.
Listed by Showcase Realty, Inc.
Sold by Tier 1 Real Estate
79 Joshua Town Rd, Waterbury, CT 06708 - Photo 1 Sold
$525,000

79 Joshua Town Rd  Waterbury, CT 06708

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,440
    Sq. Ft.
Listed by Mark Tavares Realty, LLC
Sold by Huntsman,Meade & Partners Comp
141 Joshua Town Rd, Waterbury, CT 06708 - Photo 1 Sold
$515,000

141 Joshua Town Rd  Waterbury, CT 06708

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,260
    Sq. Ft.
Listed and Sold by Ghent Realty Advisors

283 Whittemore Road, Middlebury, CT 06762 (MLS# 24169230) is a Single Family property that was sold at $500,000 on June 18, 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.