About 53 Oakland Drive
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.
Features of 53 Oakland Drive
| MLS® # | 24167633 |
|---|---|
| Price | $995,000 |
| Bedrooms | 4 |
| Bathrooms | 2/1 |
| Full Baths | 2 |
| Half Baths | 1 |
| Square Footage | 3,492 |
| Acres | 1.17 |
| Type | Single Family For Sale |
| Style | Colonial |
| Status | Closed |
Community Information
| Address | 53 Oakland Drive |
|---|---|
| Area | Long Hill |
| City | Trumbull |
| County | Fairfield |
| State | Connecticut |
| Zip Code | 06611 |
Amenities
| Features | Active Solar |
|---|---|
| Parking | Carport, Attached Garage |
| Garage Spaces | 3 |
| Is Waterfront | Yes |
| Waterfront | Pond, View, Access |
| Has Pool | Yes |
| Pool | Gunite, Heated, Spa, In Ground Pool |
Interior
| Interior Features | Auto Garage Door Opener |
|---|---|
| Appliances | Gas Range, Microwave, Range Hood, Refrigerator, Freezer, Dishwasher, Washer, Gas Dryer |
| Heating | Heat Pump, Hot Air, Solar, Zoned, Electric, Propane |
| Cooling | Central Air, Zoned |
| Fireplace | Yes |
| # of Fireplaces | 1 |
Exterior
| Exterior | Vinyl Siding |
|---|---|
| Exterior Features | Shed, Lighting, Underground Sprinkler, Patio |
| Lot Description | Treed, Level Lot, Water View |
| Roof | Asphalt Shingle |
| Foundation | Concrete |
School Information
| Elementary | Jane Ryan |
|---|---|
| Middle | Madison |
| High | Trumbull |
Additional Information
| Date Listed | April 23rd, 2026 |
|---|---|
| Days on Market | 4 |
| Zoning | A |
| RE / Bank Owned | No |
Listing Details
| Office | Compass Connecticut, LLC |
|---|
