Small-Town Charm in Oakland, Florida

Blog Author: Jeffrey Funk | Co-Founder, The Funk Collection, Brokered by eXP Realty | ICON Agent

We absolutely love the charming downtowns of Southwest Orlando, and if you love Windermere and Winter Garden, the hidden gem of Oakland should be next on your list to explore. This quaint trail town is located just 3 miles west of Winter Garden, north of 50, and is a great match for those who want to be close to the action, but have the feel of being worlds apart. 

Life Along The West Orange Trail

West Orange Trail in Oakland, FloridaThe West Orange Trail runs right through the heart of downtown, so if you've been looking for the ultimate in trail town living, Oakland may be right up your alley. The 22-mile-long trail extends west starting at…

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Price Reductions on New Construction Homes in Apopka

If you've been looking for a new construction home in west Orlando, located between Mount Dora and Wekiva Springs State Park, don't miss out on these deals in Winding Meadows. Not only can you save up to $75,000 on select quick move-in homes, but Pulte Homes is also offering a 30-year fixed rate offer 4.250% / 4.991% APR* on select quick move-ins. The Funk Collection team has hand-picked 3 must-see deals:

  • Imperial Lot 194; reduced by $75,000 is now $500,380 | 5 Bed, 3.5 Bath, 2,574 Sq Ft Home with 2-Car Garage*
  • Highgate Lot 48; reduced by $65,000 is now $476,130 | 4 Bed, 2 Bath, 1,850 Sq Ft Home with 2-Car Garage*
  • Coral Grand Lot 200; reduced by $60,000 is now $585,860 | 5 Bed, 3 Bath,…

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What makes Lake Hiawatha Preserve Stand Out in Clermont

Just a few minutes from downtown Clermont, Lake Hiawatha Preserve is one of those hidden gems that shows off exactly why people fall in love with the Florida lifestyle. The 220-acre preserve is situated on the west bank of Lake Minneola and is a perfect way to get out and explore. The Preserve is open from sunrise to sunset, seven days a week and is accessible by car or by biking the South Lake Trail, which connects with the West Orange Trail.

Florida Outdoor Living at Lake Hiawatha Preserve

Lake Hiawatha Preserve Picnic AreaAs you pull up to the Preserve from 12th Street heading north, parking is easy to spot after you take the 2nd exit on the roundabout. For those wanting closer access to the Dog Park, head to the parking…

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Dr. Phillips New Construction Home Deals in Parkview Reserve

New homes for sale in Dr. Phillips are a rare find, and the community of Parkview Reserve built by Pulte Homes is offering some must-see deals on select quick-move-in homes, anticipated to be ready by the end of October 2025. Located off Daryl Carter Parkway and Parkview Reserve Lane, this community is close to Disney, the Orlando Vineland Premium Outlets, and O-Town West.

  • 10226 Parkview Reserve Lane; reduced by $109,900 is now $1,174,720 | 4 Bed, 4 Bath, 3,080 Sq Ft Water view Home with 2-Car Garage*
  • 8267 Fenton Street; reduced by $100,000 is now $1,182,240 | 4 Bed, 4 Bath, 3,080 Sq Ft Water view Home with 2-Car Garage*
  • 10609 Bissell Street; reduced by $75,000 is now $1,198,880 |…

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Where Can You Find One of the Best Breakfast Sandwiches in Winter Garden?

Admittedly, this isn't our first visit to this breakfast favorite at the downtown Winter Garden Farmers Market. Okay, maybe not even our second. So, what is this gem of a breakfast spot that draws a crowd? It's Eggdose, the colorful yellow-and-black booth serving up breakfast sandwiches in Winter Garden, FL. The delicious scent of crispy bacon and whiffs of maple syrup draw in locals and visitors alike.

What makes Eggdose a Must-Try?

Eggdose Breakfast Sandwich at downtown Winter Garden Farmers MarketOur favorite? Picture this: a fluffy, golden brioche bun with soft scrambled eggs, melty cheddar cheese, their signature Eggdose sauce (reminds us of hollandaise), and savory, salty bacon (or breakfast meat of your choice). Is your mouth…

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Your Guide to the 2025 Windermere Craft Beer Fest

The highly anticipated return of the annual Windermere Craft Beer Fest: Re-Tapped is set for 2025! Why are we so excited about this year's event? It's been 6 years since the last event in 2019 and with 20+ local Florida breweries, food vendors, and live music, and the addition of hometown favorite Windermere Brewing Company, 2025 promises a fun-filled evening in the heart of downtown.

What to Expect This Year

The Windermere Craft Beer Fest is a tasting-style event. Think small-pours and a relaxed vibe, perfect for an evening with friends under the canopy of oak trees along Main Street. Perfect for craft beer enthusiasts and newbies alike, it offers a chance to explore and support dozens of Florida…

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New Construction Deals at Harvest At Ovation

Do not miss these quick move-in home deals by builder, Taylor Morrison in the Winter Garden community of Harvest at Ovation. Check out these three top opportunities to save big up to $50K and be in your home by November! Located west of 429 and south of Western Way, this community is located less than 3 miles to Disney property. 

  • 16029 Honey Harvest St; reduced by $50,829 is now $796,000 | 5 Bed, 4.5 Bath, 3,101 Sq Ft Home with 2-Car Garage*
  • 12892 Harvest Rain Ave; reduced by $25,000 is now $774,440 | 4 Bed, 4.5 Bath, 2,837 Sq Ft Home with 2-Car Garage*
  • 12886 Harvest Rain Ave; reduced by $25,000 is now $813,255 | 5 Bed, 4.5 Bath, 3,101 Sq Ft Home with 2.5-Car Garage*

Taylor Morrison is also…

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Exploring Sanford's Food, Culture, and Downtown Charm

There is no shortage of ways to get out and find an adventure around Orlando. Many times we are asked, "What are some of the best day trips from Windermere?" For longtime Windermere residents, Sanford is always near the top of the list. This waterside town has a true mix of historic downtown charm and a thriving food and craft beer scene, offering visitors an eclectic experience. Many times locals find themselves at the Sanford Airport, whether it be for a pick up or drop off, making it a perfect excuse to head downtown and escape for the afternoon. One of the advantages of living in Southwest Orlando is being so close to many vibrant Central Florida destinations.

Downtown Sanford Florida Fountain

How Far is Sanford from…

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Fall Deals on New Builds in Osprey Ranch

If you've been waiting for the opportunity to buy a new home in Winter Garden, now is a great time to consider the new home promotions in Osprey Ranch. K. Hovnanian Homes is offering a fall promotion on select quick-move-in homes closed by 10/31/25. Receive up to $30,000 in flex cash* that can be used in different ways:

  • Lower the home price
  • Towards closing costs
  • Reducing financing costs
  • Towards upgrades or options

Why buyers are choosing Osprey Ranch

More and more buyers are seeking homes in Winter Garden. With access to commuter roads like the 429 and proximity to Disney World, Winter Garden is a hot spot for those who are seeking a home near Orlando. Osprey Ranch, located off New…

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What Makes the 2025 Flower Show Special

Windermere Flower Show 2025 Floral DisplayThis year's Windermere Flower Show isn't just any event; it's part of the town's Centennial Celebration. Hosted by the Windermere Garden Club, "Celebrating Windermere Past and Present" is all about honoring 100 years of history, the present, and tomorrow. And honestly, what better way to celebrate Windermere than with flowers, trees, and plants that truly show off the place we call home?

What you will experience at the Show

From the moment you step inside the Windermere Town Hall, you'll find find entries in three divisions (Horticulture, Design, and Education). You'll experience everything from exhibits featuring horticulture that celebrate local flowers, trees, and plants to creative floral displays that…

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