Overlook at Lake Speer
A small gated Winter Garden lakefront community on Lake Speer.
Live the MaxLife.
$1.9M
Median Price
$1.2M – $3M
75
Homes
$275–$425
Monthly HOA
2006
Established
Keene's Crossing Elementary
School Zone
Overlook at Lake Speer — Market Pulse
Active listings + recent-sold aggregates from the Stellar MLS, 34787 area · about $258/sq ft · aggregate statistics only, no addresses or individual listings published.
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Background
A brief history
Overlook at Lake Speer was developed starting in 2006 on a parcel fronting Lake Speer in Winter Garden. Roughly 75 custom lots were released, most with direct lakefront or lake-view orientation. The recession slowed the original build-out; many lots sat unbuilt until 2013–2018 when the market recovered and construction picked up. That's why the community's home stock reads as a mix of 2006–2009 early-recession custom builds and 2014–2020 modern-lean rebuilds. Build-out is now largely complete. The lake itself is a smaller private-feeling lake with light motor-boat traffic — residents use it primarily for paddleboarding, kayaking, and pontoon recreation rather than wakeboarding or skiing.
The feel
What it's like to live here
Overlook at Lake Speer occupies a niche — it's genuinely lakefront, it's gated, and the scale is small enough (75 homes) that turnover is thin and residents know each other. Lake Speer isn't a Butler Chain lake, so the property premiums are lower than true Butler Chain lakefront, which is why the community trades at a more attainable price point than Lake Sheen Reserve or Willows on the Lake. Architecture is mixed — 2006–2009 early-recession customs in traditional and Mediterranean, plus a growing share of 2014–2020 transitional and modern lakefront builds. Lots run 0.35 to 0.8 acre. The gate is keypad rather than staffed.
The details
What to expect
Architecture & Lots
Mix of 2006–2009 early-recession customs (traditional and Mediterranean) and 2014–2020 transitional and modern lakefront builds. Main homes 3,500–6,500 square feet. Lots 0.35 to 0.8 acre. Tile, metal, and architectural shingle roofs in a mix.
Lifestyle & Amenities
Keypad gated entrance, private docks on most lakefront lots, shared community boat slips, lakefront park. Lake Speer is smaller than the Butler Chain — primarily used for paddleboarding, kayaking, and pontoon recreation rather than wakeboard or ski. No community pool or clubhouse by design.
HOA Rules & Fees
Monthly dues $275–$425. Active architectural review for exterior changes. Short-term rentals prohibited; 6-month minimum lease. Dock and boat-lift modifications require HOA plus county permits.
Schools
Zoned for Keene's Crossing Elementary, Bridgewater Middle (STEM magnet), and Windermere High School. The Horizon West school triangle is heavily in demand.
Access & Commute
Four minutes to the 429, 10 minutes to Disney, 20 minutes to Windermere downtown, 25 minutes to Restaurant Row, 35 minutes to MCO.
Community
Amenities
- Keypad gated entrance
- Direct Lake Speer frontage with private docks
- Shared community boat slips and lakefront park
- Small private-feeling lake — kayak and pontoon recreation
- More attainable lakefront price point than Butler Chain
Know Before You Buy
HOA rules worth knowing
- Monthly HOA $275–$425
- Short-term rentals prohibited; 6-month minimum lease
- Dock modifications require HOA plus county permits
- All exterior changes require architectural review
Education
School assignments
- Keene's Crossing Elementary
- Bridgewater Middle (STEM magnet)
- Windermere High School
School zone assignments change. Verify with Orange County Public Schools before purchase.
Market Commentary
What the market is doing
Current median trades in the $1.7M–$2M band. Non-waterfront interior homes move $1.2M–$1.6M. Direct Lake Speer lakefront with private docks runs $2.1M–$2.7M. A handful of recent custom rebuilds have closed $2.8M–$3M. Price-per-square-foot runs $330 for dated originals to $450 for renovated or new-build lakefront. The community is less price-sensitive than Butler Chain lakefront but more price-sensitive than the fully-unhoused non-chain lakefront parcels in Horizon West.
Active MLS Inventory
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Homes available in Overlook at Lake Speer
12 homes currently listed in Overlook at Lake Speer.
$2,850,000
9656 Weatherstone Ct
Windermere, FL 34786
6 bd · 7 ba · 7,016 sqft
Weatherstone On Lake Olivia
MLS ID #O6414766, THE AGENCY FL.
Listing provided by Stellar MLS
$799,999
9225 Mcdavid Ct
Windermere, FL 34786
4 bd · 2 ba · 2,713 sqft
Roberts Landing
MLS ID #O6424617, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$1,259,000
2230 Ridgewind Way
Windermere, FL 34786
5 bd · 4 ba · 3,064 sqft
Estates At Windermere
MLS ID #O6410264, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$1,400,000
1700 Lake Roberts Ct
Windermere, FL 34786
5 bd · 4 ba · 3,929 sqft
Butler Bay,Windermere Club
MLS ID #O6410847, CREEGAN GROUP.
Listing provided by Stellar MLS
$460,000
11429 Brownstone St
Windermere, FL 34786
4 bd · 3 ba · 1,910 sqft
Lake Burden South Ph 2
MLS ID #O6421245, WEMERT GROUP REALTY LLC.
Listing provided by Stellar MLS
$3,200 /mo
12947 Runswick Ave
Windermere, FL 34786
4 bd · 2 ba · 2,300 sqft
Lakes/Windermere Ph 02a
MLS ID #O6425118, RATIO REAL ESTATE, LLC.
Listing provided by Stellar MLS
Also Worth Seeing
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Explore Waterleigh →
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Butler Chain of Lakes
Willows on the Lake
A small gated Butler Chain community with private dock access.
$1.8M – $4.5M · 65 homes
Explore Willows on the Lake →
Butler Chain of Lakes
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Gated lakefront estates on Lake Sheen, a Butler Chain headwater.
$1.5M – $5M · 90 homes
Explore Lake Sheen Reserve →
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of July 15, 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA