Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge
2006 to 2013Years built
1,160 to 1,460 sq ftHome size
GatedEntry
Ashton WoodsBuilder
Why people move here

Gated, walkable condos behind Lakeside Village.

Lakeside is a gated condominium community of 380 homes built by Ashton Woods from 2006 to 2013. Two and three bedroom plans, a resort pool, a fitness center and an outdoor fireplace.
Publix and the Lakeside Village shops are a short walk, and Tibet-Butler Preserve is about a mile away. It is the most lock-and-leave option in this part of Windermere.
Downsizers and second-home buyers who want to lock the door and go.

Lakeside at Lakes of Windermere at a glance

Location: Off Winter Garden Vineland Road (SR 535), south of Chase Road, behind Lakeside Village

Builder: Ashton Woods

Built: 2006 to 2013

Homes: 380 condominiums

Home types: Condominiums

Size: About 1,160 to 1,460 sq ft

Bedrooms: 2 to 3 bedrooms

Entry: Gated

Area: Lakes of Windermere & Lake Burden

Life here

What Lakeside at Lakes of Windermere has

🛡Gated entry
🏊Resort-style pool
🏠Clubhouse with billiards
🏋Fitness center
🏐Beach volleyball
🍳Outdoor fireplace and grills
🚲Walking trail
⚓Shared Lake Burden dock
Proximity

What is close to Lakeside at Lakes of Windermere

  • Lakeside Village (Publix) ~0.1 mi
  • Tibet-Butler Preserve ~1.1 mi
  • West Beach Park ~1.6 mi
  • R.D. Keene Park ~1.9 mi

Approximate distances from the community entrance. Walt Disney World is roughly 10 to 15 minutes away off-peak. Two-lane roads around the lakes and SR 535 slow down at rush hour, so send me your work address and I will map your real commute.

Schools

🏫 Sunset Park Elementary

🏫 Horizon West Middle

🏫 Windermere High

Orange County Public Schools. Zoning changes, so verify every address.

OCPS school locator
The numbers

Lakeside at Lakes of Windermere market snapshot

$305,000Median sale priceDown 3.2% from $315,000 the year before.
36 daysDays on marketMedian cumulative days on market.
22Closed sales20 the year before.
97%Sale-to-list price ratioMedian for the last 12 months.

Stellar MLS, residential closed sales, 12 months ending September 30, 2026. Pulled Oct 15, 2026 and refreshed every quarter. Deemed reliable but not guaranteed. For a specific home, request a custom report.

Live MLS listings

Lakeside at Lakes of Windermere homes for sale right now

Straight from Stellar MLS. Save the search and get new Lakeside at Lakes of Windermere listings the day they hit.

Start of list of properties

Active, 8168 BOAT HOOK LOOP, , ,press enter for more details, To favorite this property press control+s.
$320,000
$222
Active
8168 BOAT HOOK LOOP
Windermere, FL 34786
3
Beds
,
2
Baths
,
1,442
square feet,
Welcome to 8168 Boat Hook Loop, Unit 303, a beautifully maintained condominium offering comfortable, low-maintenance living in a desirable community. This move-in ready residence features a spacious three-bedroom, two-bathroom floor plan designed for both everyday living and entertaining. The open-concept layout seamlessly connects the kitchen, dining, and living areas, creating a bright and inviting atmosphere. The kitchen features 42-inch upper cabinets, stone countertops, and a functional layout with ample storage and preparation space. Updates include a replaced HVAC system and hot water heater, providing added comfort and peace of mind. The spacious primary suite offers a comfortable retreat with a private en-suite bathroom and generous closet space. Two additional bedrooms provide flexibility for guests, a home office, or other lifestyle needs. Enjoy the convenience of condominium living with access to community amenities and a location close to shopping, dining, entertainment, and major roadways.
Residential
MLS# O6435857 Southern Realty Group LLC
More Details
See all Lakeside at Lakes of Windermere homes for sale
Free guides

Buying or selling in Lakeside at Lakes of Windermere?

Pick your guide, tell me where to send it, and it opens right away.

🏡 Buyer Guide

How buying in Lakeside at Lakes of Windermere works, from new construction versus resale to what to verify on HOA, CDD and school zoning.

🔑 Seller Guide

Pricing, prep and timing for selling your current home, including how to sell and buy at the same time without moving twice.

Questions buyers ask

Lakeside at Lakes of Windermere FAQ

Where is Lakeside at Lakes of Windermere in Windermere?

Lakeside at Lakes of Windermere is in the Lakes of Windermere and Lake Burden area off SR 535, at Off Winter Garden Vineland Road (SR 535), south of Chase Road, behind Lakeside Village.

How far is Lakeside at Lakes of Windermere from Walt Disney World?

Roughly 10 to 15 minutes off-peak from this part of Windermere. I will map the exact drive from the entrance before you choose.

When were homes in Lakeside at Lakes of Windermere built?

2006 to 2013, by Ashton Woods.

What amenities does Lakeside at Lakes of Windermere have?

Gated entry, Resort-style pool, Clubhouse with billiards, Fitness center, Beach volleyball, Outdoor fireplace and grills, Walking trail, Shared Lake Burden dock.

Is Lakeside at Lakes of Windermere a gated community?

Yes. Lakeside at Lakes of Windermere has a gated entry. I confirm gate type and access rules for any home before you write an offer.

What schools serve Lakeside at Lakes of Windermere?

Schools commonly listed for this community: Sunset Park Elementary, Horizon West Middle, Windermere High. Assignments change, so verify zoning for a specific address with the OCPS School Locator.

Is Lakeside at Lakes of Windermere in the Town of Windermere?

Many Windermere addresses are in unincorporated Orange County, not the Town. Taxes, rules and services differ, so I confirm the jurisdiction for every address.

What do homes in Lakeside at Lakes of Windermere sell for?

Per Stellar MLS, the median sale price in Lakeside at Lakes of Windermere was $305,000 across 22 closed sales in the 12 months ending September 30, 2026. Call or text me at 407.502.4719 for recent sales that match your home.

Your next step

Thinking about Lakeside at Lakes of Windermere?

Give me 30 minutes and tell me your timeline. I will send back:

  • Recent closed sales in Lakeside at Lakes of Windermere, straight from Stellar MLS
  • Town or county, HOA and lake access for the homes that fit
  • Your real commute, mapped from the entrance

No pressure. If you are selling a home somewhere else first, we will plan both sides together.

Semper Fi to your real estate needs. Jorge Martinez, REALTOR®

Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719
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Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge

Information deemed reliable but not guaranteed. Community details come from public sources and change over time; distances are approximate. Market data from Stellar MLS. Buyers should verify Town or county jurisdiction, school assignments, HOA, CDD, lake access and all property details independently. The JEM Property Group is an independently owned and operated real estate team affiliated with Keller Williams Realty. Equal Housing Opportunity.