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$995,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 3,492 Sq. Ft.
  • 3 Car Garage
  • Updated 9 hours ago
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Thoughtfully updated over the past four years, this exceptional four-bedroom Colonial offers a private, resort-like setting. The expansive, level property is a true outdoor oasis, featuring a picturesque pond, heated Gunite pool and spa, bluestone patio, pergola, outdoor fireplace, and a dedicated dining and grilling area. Inside, a bright, open floor plan enhances the home's inviting atmosphere. The well-appointed kitchen boasts stainless steel appliances, granite countertops, and a generous pantry, flowing seamlessly into a spacious family room with a cozy fireplace. Formal living and dining rooms showcase beautiful hardwood floors. Upstairs, all bedrooms are generously sized with ample closet space. The renovated primary and hall bathrooms offer a luxurious touch with radiant heated floors. The finished lower level provides versatile living space, including a media room, private office, and home gym. An attached two-car garage with built-in storage and a large backyard shed add convenience and functionality. Energy efficiency is a standout feature with newly installed heat pump, tankless hot water, enhanced insulation, owned solar panels, and a 14KW generator. An additional upgrade is the 50-year architectural roof (just 4 years old). The property is minutes away from shopping, the town library and school system. This is a rare opportunity to own a meticulously maintained home with exceptional indoor and outdoor living.

Full Property Details for 53 Oakland Dr

General

  • Price: $995,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24167633
  • Updated: Today (4/23/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 8
  • Rooms/Areas: Foyer, Gym, Mud Room
  • Interior Features: Auto Garage Door Opener
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Gas Range, Microwave, Range Hood, Refrigerator, Freezer, Dishwasher, Washer, Gas Dryer

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 4
  • Primary Suite: Upper
  • Bedroom 1: Bedroom, Upper
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom, Upper

Other Rooms

  • Living Room: Living Room, Main
  • Family Room: Family Room, Main
  • Kitchen: Kitchen, Main
  • Dining Room: Dining Room, Main
  • Office: Office, Lower
  • Game room: Yes
  • Game Room: Rec/Play Room, Lower
  • Rec Room: Lower
  • Laundry: Upper Level

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, Heated, Spa, In Ground Pool

Exterior

  • Exterior Features: Shed, Lighting, Underground Sprinkler, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Parking: Carport, Attached Garage

Location

  • County: Fairfield
  • Neighborhood: Long Hill
  • Driving Directions: Main Street to Oakland Drive

School Information

  • Elementary School: Jane Ryan
  • Middle School: Madison
  • High School: Trumbull

Community

  • Community Name: Long Hill

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Heat Pump, Hot Air, Solar, Zoned, Electric, Propane
  • Heating Fuel: Electric, Propane
  • Water Heater: Propane, Tankless Hotwater

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Heated, Fully Finished, Cooled
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,492
  • Above Ground: 2,471 Sq. Ft.
  • Below Ground: 1,021 Sq. Ft.
  • Year Built: 1996

Lot Features

  • Lot Size (Acres): 1.17
  • Zoning: A
  • Lot Description: Treed, Level Lot, Water View

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Pond, View, Access

Green Features

  • Energy Features: Active Solar

Financial Considerations

  • Assessment Amount: $425,250
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 390534

Listed by Compass Connecticut, LLC, Tyler Toren

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Listing agent

— 53 Oakland Dr —

  • Tyler Toren

    Compass Connecticut, LLC

Agent Contact: (610) 301-1079 Office Contact: (203) 343-0141

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 53 Oakland Dr

School District:Trumbull School District
NameGradesDistance
Jane Ryan School
190 Park Lane, Trumbull, CT 06611
K-50.9 mi
Madison Middle School
4630 Madison Avenue, Trumbull, CT 06611
6-81.3 mi
Trumbull High School
72 Strobel Road, Trumbull, CT 06611
9-122 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 53 Oakland Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/23/2026
Listed
$995,000
60.48%
MLS
8/31/2018
Sold
$620,000
—
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 53 Oakland Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$15,626
3%
$425,250
—
2023
$15,184
3%
$425,250
—
2022
$14,701
11%
$425,250
17%
2021
$13,198
2%
$362,950
—
2020
$12,944
11%
$362,950
9%
2018
$11,632
2%
$333,620
—
2017
$11,416
3%
$333,620
—
2016
$11,123
1%
$333,620
1%
2015
$11,048
2%
$330,100
—
2014
$10,814
3%
$330,100
—
2011
$10,527
—
$330,100
—
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 53 Oakland Dr

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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 Compass Connecticut, LLC, Tyler Toren

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53 Oakland Drive, Trumbull, CT 06611 (MLS# 24167633) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 53 Oakland Drive is currently listed for $995,000 and was received on April 23, 2026. Want to learn more about 53 Oakland Drive? Do you have questions about finding other Single Family real estate for sale in Trumbull? You can browse all Trumbull real estate or contact a Coldwell Banker agent to request more information.

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