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$555,000

  • Sold
  • Closed
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,647 Sq. Ft.
  • 2 Car Garage
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**HIGHEST & BEST OFFERS DUE TUES, NOV 4 @ 12PM** Looking for the perfect blend of comfort, convenience, and one level living? This beautifully maintained ranch is situated on a quiet side street in one of Trumbull's most desirable neighborhoods and is the perfect place to call home! 14 Oakland Drive welcomes you with sun-filled rooms, gleaming hardwood floors, crown molding, and a sense of warmth throughout. Sunlight pours in through the bay window, illuminating the living room with hardwood floors and a brick fireplace. Seamless flow brings you into the dining room, ideal for everyday living or entertaining. The kitchen features wood cabinetry, a skylight and an eating area. Access to the deck overlooking the private backyard offers an easy connection between indoor/outdoor living. Down the hall, you will find 3 bedrooms and a full bathroom. The partially finished LL features a large rec room, full bath, laundry room, and two multi-purpose spaces - think home office, gym, playroom, or guest suite. A two car garage completes this home. The flat, shaded backyard is perfect for relaxing during spring, summer and autumn nights or for hosting parties, enhanced by the pretty backdrop of mature trees & beautiful landscaping. Set in a peaceful neighborhood minutes to schools, hiking trails, parks, restaurants, highway. 14 Oakland Drive has been loved by the owners for 60 years and is waiting for you to put your own personal touch on it and make memories for years to come.

Full Property Details for 14 Oakland Dr

General

  • Sold For: $555,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24136348
  • Added to Site: 78 day(s) ago

Interior

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

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Full Bath: Stall Shower, 4 x 8, Lower

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - Ceiling Fan, Hardwood Floor, 12 x 13, Main
  • Bedroom 1: Bedroom - Hardwood Floor, 12 x 10, Main
  • Bedroom 2: Bedroom - Ceiling Fan, Hardwood Floor, 9 x 8, Main

Other Rooms

  • Living Room: Living Room - Bay/Bow Window, Fireplace, Hardwood Floor, 17 x 11, Main
  • Kitchen: Kitchen - Skylight, 13 x 10, Main
  • Dining Room: Dining Room - Hardwood Floor, 10 x 12, Main
  • Office: Office, 8 x 14, Lower
  • Game room: Yes
  • Game Room: Rec/Play Room, 25 x 11, Lower
  • Rec Room: 25 x 11, Lower
  • Laundry: Lower Level
  • Other Room 1: Other, 14 x 8, Lower

Exterior

  • Exterior Features: Deck, Gutters, Lighting
  • Color: Beige

Parking

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

Location

  • County: Fairfield
  • Neighborhood: Long Hill
  • Driving Directions: Main Street to Oakland Drive. House on right.

School Information

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

Community

  • Community Name: Long Hill

Heating & Cooling

  • Cooling Type: Ceiling Fans, Central Air
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Upright Tank, 40 Gallon Tank

Utilities

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

Structural Information

  • Architectural Style: Ranch
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Sump Pump, Storage, Interior Access, Partially Finished, Liveable Space, Full With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 1,647
  • Above Ground: 1,148 Sq. Ft.
  • Below Ground: 499 Sq. Ft.
  • Year Built: 1955

Lot Features

  • Lot Size (Acres): 0.3
  • Zoning: A
  • Lot Description: Level Lot

Financial Considerations

  • Assessment Amount: $236,670
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 392250

Listed by William Raveis Real Estate, Pritchard Homes Team at William Raveis Real Estate, Sarah Pritchard Provenzano
Sold by William Pitt Sotheby's Int'l, Mary Amenda

Listing agent

— 14 Oakland Dr —

  • Sarah Pritchard Provenzano

    William Raveis Real Estate

Agent Contact: (203) 414-5571 Office Contact: (203) 255-6841

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 14 Oakland Dr

School District:Trumbull School District
NameGradesDistance
Jane Ryan School
190 Park Lane, Trumbull, CT 06611
K-51 mi
Madison Middle School
4630 Madison Avenue, Trumbull, CT 06611
6-81.5 mi
Trumbull High School
72 Strobel Road, Trumbull, CT 06611
9-121.8 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 14 Oakland Dr

Date
Details
Price
Change
Source
12/22/2025
Sold
$555,000
11.22%
MLS
10/29/2025
Listed
$499,000
—
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 William Raveis Real Estate, Pritchard Homes Team at William Raveis Real Estate, Sarah Pritchard Provenzano
Sold by William Pitt Sotheby's Int'l, Mary Amenda

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14 Oakland Drive, Trumbull, CT 06611 (MLS# 24136348) is a Single Family property that was sold at $555,000 on December 22, 2025. Want to learn more about 14 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.