Metcalf Park
Windermere's original lakefront address — Lake Butler Boulevard.
Live the MaxLife.
$6.5M
Median Price
$4M – $17.3M
60
Homes
$0–$0
Monthly HOA
1925
Established
Windermere Elementary
School Zone
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Background
A brief history
Metcalf Park is one of the oldest residential plats in Windermere, running along Lake Butler Boulevard on the east shore of Lake Butler. Original lots were platted in the 1920s during the first Florida land boom, and the street still contains a mix of restored 1950s cottages, 1980s–90s traditional estates, and trophy new-construction custom builds. Unlike Isleworth, Keene's Pointe, or Chaine du Lac, there is no gate — Lake Butler Boulevard is a historic public road that runs the length of the lake's eastern shore. The architectural character is eclectic, and the street's defining feature is its mature tree canopy and 100-foot-plus Butler Chain lake frontages.
The feel
What it's like to live here
Metcalf Park is 'old Windermere' in the literal sense — it predates almost every other luxury community in the area and lacks the gate-and-clubhouse formula that defines the rest of the market. Residents walk or bike along Lake Butler Boulevard, kids fish off private docks, and the street feels more like a historic lakefront neighborhood than a master-planned enclave. That informality is the attraction for a specific kind of buyer — one who wants trophy Butler Chain frontage without the HOA, buyer-approval, or architectural-review regime that comes with gated communities. It's also the one place on the Butler Chain where you'll see a 1954 lakefront cottage and a $17M custom-modern estate on adjacent lots.
The details
What to expect
Architecture & Lots
Mix of eras — 1950s lakefront cottages (a few remaining), 1980s–90s traditional estates, and 2010s–2020s custom Modern and Transitional builds. Lot sizes 1 to 5+ acres with 80 to 200+ feet of Butler Chain frontage. Expect boathouses, covered lifts, and deep-water docks on almost every property.
Lifestyle & Amenities
The amenity is the Butler Chain and the street itself. No HOA, no clubhouse, no gate. Residents have direct access to Lake Butler (which connects to the entire 13-lake chain) and walking/biking access down Lake Butler Boulevard. The historic downtown Windermere core is a 5-minute drive, Isleworth and Keene's Pointe golf club memberships are available to residents who want private club access.
HOA Rules & Fees
No HOA. No architectural review board. No buyer-approval process. Standard Town of Windermere and Orange County building codes apply. This is one of the few Butler Chain luxury streets where a buyer has full control over design and timeline.
Access & Commute
Direct access off Main Street in downtown Windermere — 5 minutes to Park Avenue and the historic town core, 15 minutes to Isleworth, 20 minutes to Dr. Phillips and Restaurant Row, 30 minutes to Orlando International Airport.
Buying Process
Inventory is tight — expect off-market activity to dominate. Many trades happen between neighbors, longtime family contacts, and through builders who track the street. Standard title and due diligence; no association approvals.
Community
Amenities
- Direct Butler Chain of Lakes frontage (Lake Butler)
- Private boathouses, covered lifts, and deep-water docks
- Walking and biking distance to historic downtown Windermere
- No HOA, no gate, no architectural review board
- Mature oak canopy along Lake Butler Boulevard
- Historic 1920s plat — the oldest lakefront address in Windermere
Know Before You Buy
HOA rules worth knowing
- No HOA
- Town of Windermere and Orange County building codes apply
- No buyer-approval process
- No architectural review board
Education
School assignments
- Windermere Elementary
- Gotha Middle School
- Olympia High School
- Private: Windermere Prep, The First Academy
School zone assignments change. Verify with Orange County Public Schools before purchase.
Market Commentary
What the market is doing
Pricing reflects the eclecticism — entry at $4M for an older lakefront cottage on a narrower lot, median around $6–7M, and trophy new-construction estates clearing $17M on the larger parcels. Price-per-square-foot on new builds has pushed past $1,600 on the premier lots. Resale velocity is slow (5–8 transactions per year across the entire street) because owners tend to hold for generations. When a lot does trade, builders actively pursue it.
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Homes available in Metcalf Park
12 homes currently listed in Metcalf Park.
$1,390,000
2014 Down Woods Ln
Windermere, FL 34786
4 bd · 4 ba · 3,344 sqft
Lake Down Woods
MLS# O6413750
$850,000
11155 Lake Butler Blvd
Windermere, FL 34786
3 bd · 2 ba · 1,935 sqft
Wauseon Ridge
MLS# O6414373
$2,999,000
5073 Latrobe Dr
Windermere, FL 34786
4 bd · 6 ba · 4,706 sqft
Isleworth
MLS# O6414325
$3,395 /mo
6873 Northwich Dr
Windermere, FL 34786
3 bd · 3 ba · 2,229 sqft
Lakes Windermere Ph 01 49 108
MLS# O6414222
$1,400 /mo
Windermere, FL 34786
1 bd · 1 ba · 528 sqft
Carrington Townhomes
MLS# O6414255
$14,990 /mo
801 W 2nd Ave
Windermere, FL 34786
5 bd · 7 ba · 5,639 sqft
Aladar On Lake Butler
MLS# O6414179
Also Worth Seeing
Related communities
Windermere
Chaine du Lac
Windermere's quietest gate on the Butler Chain.
$4.5M – $15.5M · 40 homes
Explore Chaine du Lac →
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Reserve at Lake Butler Sound
Windermere's intimate lakefront enclave on Lake Butler.
$2M – $15M · 150 homes
Explore Reserve at Lake Butler Sound →
Windermere
Isleworth
Arnold Palmer's Windermere legacy — Florida's most private address.
$2M – $40M · 660 homes
Explore Isleworth →
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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 June 6, 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.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA