877 TILDEN OAKS TRAIL, MLS# – O6343042

Modern Craftsman Charmer in Oakland Park – Corner Lot, No Rear Neighbors, and Steps from the West Orange Trail!
Welcome to 877 Tilden Oaks Trail, a beautifully designed David Weekley Modern Craftsman home in the heart of Oakland Park—one of Winter Garden’s most sought-after communities. Featuring 5 bedrooms, 4 bathrooms, 3,084 sq. ft., and stunning curb appeal, this move-in ready home offers timeless character, incredible location, and thoughtful upgrades throughout. Situated on a private corner lot with no rear neighbors, this home delivers both space and serenity. From the inviting rocking-chair front porch to the charming detached rear-entry garage with a Tesla Level 2 EV charger, every detail has been carefully curated. Inside, you’ll find wide-plank white oak laminate flooring, a dedicated home office, and an open-concept layout that flows beautifully for entertaining. The chef’s kitchen is a showstopper, boasting quartz countertops, a farmhouse sink, built-in wall oven and microwave, custom 42″ solid wood cabinetry, and a gorgeous herringbone tile backsplash—all centered around a large island ideal for gatherings. The first-floor primary suite is a true retreat with a spa-inspired bathroom featuring wood-look ceramic tile, dual vanities, a soaking tub, a walk-in shower, and an oversized custom walk-in closet. The spacious family room opens up to a screened-in rear patio through elegant French doors, providing indoor-outdoor living year-round. Upstairs, you’ll find a large loft and three additional bedrooms, perfect for family, guests, or flex space. This layout offers versatility for today’s modern lifestyle. Live the Florida Lifestyle in Oakland Park, a masterfully planned traditional neighborhood design (TND) community with mature oaks, lakes, parks, and preserved natural beauty that captures the essence of “Old Florida.” Amenities include: Two resort-style pools, Walking trails and green spaces, Direct access to the West Orange Trail (just 2 blocks away!), Golf cart access throughout and into the Historic Downtown Winter Garden district
Located in the golf cart district, you’re just minutes (or a short bike/golf cart ride) from: Downtown Winter Garden, Plant Street Market, Crooked Can Brewery, boutique shops, weekly farmers market, and local eateries – Top-rated public and private schools – Easy access to major highways including SR 429 and the Turnpike. Why wait to build new? Inventory is tight and new construction comes with long wait times and rising costs. This home is move-in ready, meticulously maintained, and packed with upgrades—making it an ideal opportunity for buyers who want it all, now. Don’t miss your chance to own this one-of-a-kind home in one of Central Florida’s most beloved communities. Schedule your private tour today!

Additional Details

• Elementary School: Tildenville Elem
• Middle Or Junior School: Lakeview Middle
• High School: West Orange High
• Association Amenities: Clubhouse, Park, Playground, Pool, Recreation Facilities, Trail(s)
• Baths Full: 4
• Baths Half: 0
• Modification Timestamp: September 19, 2025 at 07:23pm
• Builder Model: Skyline
• Builder Name: David Weekley Homes
• Building Area: 4193
• Cooling: Central Air, Zoned
• Days on the Market: 8
• Direction Faces: West
• Directions: From Downtown Winter Garden, head west on Plant St which becomes Oakland Avenue. Turn right onto Tilden Oaks Trail. Home Will be on your right. You can park on either side of Tilden Oaks Trail, or in the driveway down the alley.
• Flooring: Carpet, Ceramic Tile, Laminate
• Foundation Details: Slab
• Furnished: Unfurnished
• Heating: Central, Electric, Heat Pump, Natural Gas, Zoned
• Laundry Features: Inside, Laundry Room
• Levels: Two
• List Agent Email: [email protected]
• List Agent: Matthew Matin
• List Agent Phone: 321-948-5857
• List Office: CLOCK TOWER REALTY
• List Office Phone: 407-832-7332
• Listing Terms: Cash, Conventional, VA Loan
• Lot Features: Corner Lot, City Lot
• MLS Area Major: 34787 - Winter Garden/Oakland
• MLS Status: Active
• Modification Time Stamp: September 19, 2025 at 07:18pm
• Roof: Shingle
• Source System: 769539877
• Status Change Time: September 11, 2025 at 04:17pm
• View: Trees/Woods
• WaterSource: Public
• Zoning: PUD