883 Tilden Oaks Trail

Off Market

883 Tilden Oaks Trail

Oakland FL 34787

3992 sq. ft.

6500 sq. ft.

Single-Family

Last sold for $1,075,000

Matthew McKee, last sold this property on 30 April 2026 after 16 days on market.

Overview

Nestled in the heart of Winter Garden’s beloved Golf Cart District, this oversized Seaside model by David Weekley invites you to embrace a lifestyle where luxury meets charm. Tucked within the picturesque Oakland Park Subdivision, this home offers not just a place to live but a way to experience the very best of this vibrant community. Step inside, and you’re greeted by the golden warmth of light wood laminate floors and streams of natural light pouring through every window. The gourmet kitchen, truly the soul of the home, is a chef’s haven with a gas stovetop, sleek finishes, and plenty of room to gather, cook, and connect. Just steps away, the main-floor master retreat becomes your personal sanctuary—offering peace, privacy, and every comfort you could wish for. The second floor is a haven in its own right, with three spacious bedrooms circling a versatile loft space. Whether it becomes a playroom, a cozy reading nook, or your dream work-from-home setup, the possibilities are endless. Outside, the rare 3-car garage, discreetly accessed via a quiet alley, adds both convenience and a touch of exclusivity. But the magic doesn’t stop at your doorstep. Imagine mornings strolling leafy trails, afternoons exploring Winter Garden's historic downtown, and evenings savoring craft beer or artisan treats at the nearby Plant Street Market—a true local gem just moments away. From farmers markets to boutique shops, this is a neighborhood where every day feels like a celebration. This isn’t just a home; it’s a gateway to the lifestyle you’ve been dreaming of. Don’t wait—schedule your private tour today and let this storybook setting become your reality.

Features

4 bedrooms

4 bathrooms

3 carspaces

3 garage spaces

3992 sq. ft. floor area

6500 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Oakland over the last 12 months, the estimated median property value of 883 Tilden Oaks Trail is $659.84k.

Median value

$659.84k

Estimated value range

$135k - $2.7m

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Oakland. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 883 Tilden Oaks Trail

2026

Sold

$1,075,000

30 Apr 2026 by Matthew McKee, of COMPASS FLORIDA LLC

Happy sellers in Oakland

91%

91% of sellers in Oakland reported that their sale price either exceeded or met their price expectations.

Oakland stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 41 reviews in Oakland over the last 12 months.

Local market activity for 4 bedroom single-family properties in Oakland

In the last 12 months, 701 four-bedroom single-family properties similar to 883 Tilden Oaks Trail, have been sold.

This represents a 16% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Oakland for a market analysis.

Heidi Pfeffer-Morgan

at Dalton Wade | Florida

(38 reviews)

Get a market analysis

Erica Diaz

at Erica Diaz Team

(633 reviews)

Get a market analysis

Angela Camacho

at La Rosa Realty LLC

(68 reviews)

Get a market analysis

Sherri Palmer

(97 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Oakland

Heidi Pfeffer-Morgan

Sellers who recommend Heidi Pfeffer-Morgan have praised them for being clear communication, reliable, dedicated, great negotiation, local expert, friendly, and resourceful

5 (38 reviews)
9 Reviews in Oakland
8 Sales in Oakland

View profile

Erica Diaz

Erica Diaz is an award winning recommended agent for Oakland. They have 46 local sales and collected 7 local reviews across the last 12 months.

5 (633 reviews)
7 Reviews in Oakland
46 Sales in Oakland

View profile

Angela Camacho

Angela Camacho is a recommended agent for Oakland. They have 7 local sales and collected 6 local reviews across the last 12 months.

5 (68 reviews)
6 Reviews in Oakland
7 Sales in Oakland

View profile

Sherri Palmer

Sellers who recommend Sherri Palmer have praised them for being local expert, responsive, clear communication, supportive, detail-oriented, dedicated, and friendly