**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. LOWER LEVEL SQUARE FOOTAGE IS FINISHED BUT NOT HEATED
Sold for $555,000
$555,000
14 Oakland Drive, Trumbull, CT 06611
3beds
1,647sqft
Single Family Residence
Built in 1955
0.3 Acres Lot
$579,200 Zestimate®
$337/sqft
$3,860 Estimated rent
Home value
$579,200
$521,000 - $643,000
$3,860/mo
Zestimate® history
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$3,793/mo
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List your homeWhat's special
Brick fireplaceSun-filled roomsMature treesQuiet side streetCrown moldingBeautiful landscapingFlat shaded backyard
Zillow last checked:
Listing updated:
Listed by:
Pritchard Homes Team at William Raveis Real Estate,
Sarah Pritchard Provenzano (203)414-5571,
William Raveis Real Estate 203-255-6841
Bought with:
Mary Amenda, RES.0011551
William Pitt Sotheby's Int'l
Source: Smart MLS,MLS#: 24136348
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Features: Ceiling Fan(s), Hardwood Floor
- Level: Main
- Area: 156 Square Feet
- Dimensions: 13 x 12
Bedroom
- Features: Hardwood Floor
- Level: Main
- Area: 120 Square Feet
- Dimensions: 10 x 12
Bedroom
- Features: Ceiling Fan(s), Hardwood Floor
- Level: Main
- Area: 72 Square Feet
- Dimensions: 8 x 9
Bathroom
- Features: Tub w/Shower
- Level: Main
- Area: 42 Square Feet
- Dimensions: 6 x 7
Bathroom
- Features: Stall Shower
- Level: Lower
- Area: 32 Square Feet
- Dimensions: 8 x 4
Dining room
- Features: Hardwood Floor
- Level: Main
- Area: 120 Square Feet
- Dimensions: 12 x 10
Kitchen
- Features: Skylight
- Level: Main
- Area: 130 Square Feet
- Dimensions: 10 x 13
Living room
- Features: Bay/Bow Window, Fireplace, Hardwood Floor
- Level: Main
- Area: 187 Square Feet
- Dimensions: 11 x 17
Office
- Level: Lower
- Area: 112 Square Feet
- Dimensions: 14 x 8
Other
- Level: Lower
- Area: 112 Square Feet
- Dimensions: 8 x 14
Rec play room
- Level: Lower
- Area: 275 Square Feet
- Dimensions: 11 x 25
Heating
- Hot Water, Oil
Cooling
- Ceiling Fan(s), Central Air
Appliances
- Included: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Lower Level
Features
- Basement: Full,Sump Pump,Storage Space,Interior Entry,Partially Finished,Liveable Space
- Attic: Pull Down Stairs
- Number of fireplaces: 1
Interior area
- Total structure area: 1,647
- Total interior livable area: 1,647 sqft
- Finished area above ground: 1,148
- Finished area below ground: 499
Property
Parking
- Total spaces: 2
- Parking features: Attached
- Attached garage spaces: 2
Features
- Patio & porch: Deck
- Exterior features: Rain Gutters, Lighting
Lot
- Size: 0.3 Acres
- Features: Level
Details
- Parcel number: 392250
- Zoning: A
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1955
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: Basketball Court, Golf, Lake, Library, Park, Public Rec Facilities, Shopping/Mall, Tennis Court(s)
- Subdivision: Long Hill
HOA
- Has HOA: No
Location
- Region: Trumbull
Financial & listing details
- Price per square foot: $337/sqft
- Tax assessed value: $236,670
- Annual tax amount: $8,696
- Date on market: 10/29/2025
Price history
| Date | Event | Price |
|---|---|---|
| 12/22/2025 | Sold | $555,000+11.2%$337/sqft |
Source:  Smart MLS #24136348 Report a problem | ||
| 10/29/2025 | Listed for sale | $499,000+38.6%$303/sqft |
Source: Smart MLS #24136348 Report a problem | ||
| 12/2/1997 | Sold | $359,900$219/sqft |
Source: Smart MLS #97007646 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $8,696 +2.9% | $236,670 |
| 2024 | $8,451 +1.6% | $236,670 |
| 2023 | $8,316 +1.6% | $236,670 |
| 2022 | $8,182 +15.8% | $236,670 +21.8% |
| 2021 | $7,066 +2% | $194,320 |
| 2020 | $6,930 +2.3% | $194,320 |
| 2018 | $6,775 +1.9% | $194,320 |
| 2017 | $6,650 +1.6% | $194,320 -0.6% |
| 2015 | $6,543 +2.2% | $195,500 |
| 2014 | $6,405 +2.7% | $195,500 |
| 2013 | $6,234 +3.8% | $195,500 |
| 2012 | $6,004 -6% | $195,500 -21.9% |
| 2011 | $6,385 +1.2% | $250,400 |
| 2010 | $6,310 +4.7% | $250,400 |
| 2009 | $6,027 +0.9% | $250,400 |
| 2008 | $5,975 +5.1% | $250,400 |
| 2007 | $5,684 +3.8% | $250,400 +1.2% |
| 2006 | $5,475 +23.4% | $247,400 +73.9% |
| 2005 | $4,435 +6.4% | $142,240 |
| 2004 | $4,170 +4.1% | $142,240 -2.1% |
| 2003 | $4,006 +14.9% | $145,300 +0.1% |
| 2001 | $3,485 +7.8% | $145,200 +20% |
| 2000 | $3,232 +6.8% | $121,030 |
| 1999 | $3,026 | $121,030 |
Find assessor info on the county website
Neighborhood: Long Hill
Nearby homes
- $478,9003 bd1 ba1.1k sqft10 Oakland Dr, Trumbull, CT 06611Off Market
- $543,0003 bd2 ba1.3k sqft24 Oakland Dr, Trumbull, CT 06611Off Market
- $673,6003 bd2 ba1.9k sqft15 Meadowview Dr, Trumbull, CT 06611Off Market
- $484,8002 bd1 ba1.4k sqft15 Oakland Dr, Trumbull, CT 06611Off Market
- $593,6003 bd2 ba1.6k sqft17 Meadowview Dr, Trumbull, CT 06611Off Market
- $658,6003 bd2 ba2.6k sqft11 Meadowview Dr, Trumbull, CT 06611Off Market
- $534,5003 bd2 ba1.1k sqft9 Oakland Dr, Trumbull, CT 06611Off Market
- $616,0003 bd1 ba1.4k sqft19 Oakland Dr, Trumbull, CT 06611Off Market
Nearby schools
GreatSchools rating
- 9/10Jane Ryan SchoolGrades: K-5Distance: 1 mi
- 8/10Madison Middle SchoolGrades: 6-8Distance: 1.5 mi
- 10/10Trumbull High SchoolGrades: 9-12Distance: 1.8 mi
Schools provided by the listing agent
- Elementary: Jane Ryan
- Middle: Madison
- High: Trumbull
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Connecticut
- Fairfield County
- Trumbull
- 06611
- Long Hill
- 14 Oakland Drive
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