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Bay Isle Homes for Sale

14411 Hampshire Bay Circle, Winter Garden image
14411 Hampshire Bay Circle, Winter Garden $885,000 ▼

Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers home offers a rare combination of sophisticated design, thoughtful craftsmanshi...

  • 4 Beds
  • 5 Baths
  • Bay Isle 48 17 SubDv.
  • 34787 Zip Code
Home › Winter Garden › Bay Isle
📋 What's on This Page
  • About Bay Isle Neighborhood
  • Location & Connections
  • Neighborhood Amenities & Lifestyle
  • HOA Information
  • Frequently Asked Questions
  • Available Homes

Bay Isle Homes for Sale

Winter Garden, FL 34787 | Black Lake-Adjacent Neighborhood in Southern 34787

Bay Isle is a small residential neighborhood in Winter Garden set just east of Black Lake, between the Daniels Road and Winter Garden Vineland Road corridors south of SR 50. The neighborhood sits in the southern 34787 area near Black Lake Park, Country Lakes, and Glynwood, with quick access to SR 429, Florida's Turnpike, and Winter Garden Village. View Available Homes

✔ Information verified current as of May 2026

About Bay Isle Neighborhood

Bay Isle is a compact established subdivision in southern Winter Garden, positioned along the eastern edge of Black Lake — a roughly 212-acre lake that anchors a cluster of small lakefront and lake-adjacent neighborhoods on the south side of the city. The neighborhood is set inside the Daniels Road / Winter Garden Vineland Road grid, with Stoneybrook West sitting across Black Lake to the southwest.

The setting is residential and quiet — single-family homes on conventional lots, mature landscaping common throughout the area, and direct connections out to SR 429 and the Turnpike for commutes north into Apopka or south toward I-4 and the theme park corridor. Unlike the master-planned, amenity-heavy communities further south in Horizon West, Bay Isle reads as a smaller, more conventional neighborhood — closer in character to Black Lake Park and Glynwood than to a Hamlin or Bridgewater village.

Bay Isle's draw is location: walking-distance proximity to Black Lake green space, a short drive to Winter Garden Village for everyday retail, and quick highway access without the CDD assessments that come with newer Horizon West construction. Buyers looking for an established 34787 address south of SR 50 — without the price step into Stoneybrook West's gated golf community — tend to consider this corridor.

📊 Quick Facts
Property Style:Single-family homes
Setting:Black Lake-adjacent, southern 34787
HOA Fee:Contact us for current fee
CDD Fee:No (verify with county records)
Nearest Lake:Black Lake (~212 acres)
School District:Orange County Public Schools
🌳 Black Lake Setting

Bay Isle sits on the east side of Black Lake, a roughly 212-acre natural lake in southern Winter Garden. The lake is a defining geographic feature for this part of 34787 — Black Lake Park is the closest direct-access neighborhood, with Stoneybrook West occupying the larger gated/golf community footprint across the water to the southwest. Lake access from Bay Isle itself is not a community amenity; the value here is lake-adjacent green space and the lower-density feel that comes with proximity to the lake basin.

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Bay Isle Location & Connections

Bay Isle is located in southern Winter Garden, set inside the Daniels Road and Winter Garden Vineland Road corridors east of Black Lake. The neighborhood is roughly two miles south of SR 50 and sits within easy reach of both SR 429 and Florida's Turnpike, making commutes in either direction along the western Orlando metro straightforward. Downtown Winter Garden and the historic Plant Street district sit roughly five miles north.

🏘️ Adjacent Neighborhoods & Areas
  • Black Lake Park — directly adjacent on Black Lake
  • Country Lakes (also referenced as Country Lake Estates) — neighboring established subdivision
  • Glynwood — neighboring 34787 subdivision
  • Stoneybrook West — gated golf community across Black Lake to the southwest
  • Black Lake (~212-acre lake) — defining western boundary of this neighborhood cluster
  • Winter Garden Vineland Road (CR 535) and Daniels Road — the two primary north-south arteries serving the area
🚗 Detailed Commute Times
  • Downtown Orlando: ~25–30 minutes (~17 miles via SR 429 / SR 408)
  • UCF Campus: ~35–45 minutes (~28 miles)
  • Walt Disney World: ~15–20 minutes (~10 miles via SR 429)
  • Universal Orlando: ~20–25 minutes (~14 miles)
  • SeaWorld Orlando: ~20–25 minutes (~15 miles)
  • Cocoa Beach: ~75–90 minutes (~70 miles)
  • Winter Garden Village: ~5–8 minutes (~2.5 miles)
  • Downtown Winter Garden / Plant Street: ~10–12 minutes (~5 miles)
✈️ Airport Access
  • Orlando International Airport (MCO): ~30–35 minutes (~22 miles via SR 429 / SR 528)
  • Orlando Sanford International Airport (SFB): ~50–55 minutes (~40 miles)

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Bay Isle Amenities & Lifestyle

Daily life in Bay Isle leans on its surroundings rather than internal amenities. Black Lake green space sits at the doorstep, Winter Garden Village is a short drive north for everyday retail, and the historic Plant Street downtown core in downtown Winter Garden is roughly five miles away for restaurants, the West Orange Trail, and weekend events.

For broader context on what's available across the city, the Winter Garden hub guide covers the full set of neighborhoods, schools, parks, and category guides.

🏊 Neighborhood Amenities

Bay Isle is a small residential subdivision without a substantial amenity footprint of its own. Buyers looking for community pools, clubhouses, fitness centers, or gated entries typically consider larger nearby communities such as Stoneybrook West.

Note: HOA-managed amenities specific to Bay Isle should be verified with the HOA management company before relying on them.

🛍️ Shopping & Services

The closest major retail destination is Winter Garden Village at Fowler Groves, an 80+ store open-air shopping center off Daniels Road with anchor stores, big-box retail, and everyday services. Plant Street's downtown shopping district adds independent retail roughly five miles north.

For comprehensive shopping information: View our Winter Garden Shopping Guide →

🍽️ Restaurants

Dining options near Bay Isle range from chain restaurants at Winter Garden Village to the independent restaurants and breweries clustered along Plant Street in downtown Winter Garden, including the Plant Street Market food hall and Crooked Can Brewing.

For comprehensive restaurant information: View our Winter Garden Restaurants Guide →

🎭 Arts & Culture

Downtown Winter Garden's cultural anchors — the restored 1935 Garden Theatre, the Winter Garden Heritage Museum, and the Central Florida Railroad Museum — are roughly five miles from Bay Isle along Plant Street.

For comprehensive arts & culture information: View our Winter Garden Arts & Culture Guide →

🏃 Health & Wellness

AdventHealth Winter Garden Hospital on Fowler Grove Boulevard is the closest full-service hospital, located near Winter Garden Village roughly two to three miles from Bay Isle.

For comprehensive health & wellness information: View our Winter Garden Hospitals Guide →

🌳 Parks & Recreation

The most defining nearby outdoor asset is Black Lake itself, with the surrounding green space along its eastern shore. The West Orange Trail — a 22-mile paved rail-trail running through downtown Winter Garden — is a short drive north and a primary recreation draw for the area.

For comprehensive parks & recreation information: View our Winter Garden Parks & Recreation Guide →

⚽ Sports & Athletics

Stoneybrook West Golf Club sits across Black Lake and is the closest semi-private course to Bay Isle. The West Orange Trail handles cycling and running for the area.

For comprehensive sports & athletics information: View our Winter Garden Sports & Athletics Guide →

🎉 Fun Things to Do

Weekend options near Bay Isle range from the Saturday farmers market and seasonal events on Plant Street to Newton Park on Lake Apopka for sunset views, plus the full theme park corridor a 15–20 minute drive south.

For comprehensive events & activities information: View our Winter Garden Events & Things To Do Guide →

🎓 Schools

Bay Isle is not explicitly listed in published OCPS attendance-zone reference materials. Based on the surrounding Stoneybrook West / NW 34787 cluster, Bay Isle is likely zoned for:

  • Elementary: Whispering Oak Elementary (likely — verify with OCPS)
  • Middle: SunRidge Middle (likely — verify with OCPS)
  • High: West Orange High (likely — verify with OCPS)

School assignments are subject to change. Always verify current attendance zones directly with Orange County Public Schools before relying on this information for a purchase decision.

For comprehensive school information: View our Winter Garden Schools Guide →

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Bay Isle HOA & CDD Information

Bay Isle is a deed-restricted neighborhood managed by a homeowners association. As an established subdivision pre-dating the Horizon West master-plan era, Bay Isle is not part of a Community Development District — buyers should not expect a CDD assessment on top of property taxes here, though this should be confirmed against current Orange County tax records before closing.

💰 HOA Fees & Management Contact

HOA fees and management company information often change. Please contact us and we will be happy to provide you with the current HOA fee, payment schedule, and direct contact information for the HOA management company. We can also check for you to see if there are any current or upcoming special assessments.

📋 What HOA Fees Typically Cover

For an established small subdivision like Bay Isle, HOA dues typically fund a focused set of items rather than the resort-style amenities found in larger gated communities. Common coverage areas include:

  • Common-area landscaping and maintenance
  • Entrance signage and any community-owned features
  • Architectural review and deed-restriction enforcement
  • Reserve funds for long-term maintenance
  • HOA insurance and administrative costs

Specific coverage varies by community. Confirm with the HOA management company.

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Frequently Asked Questions

What is the HOA fee for Bay Isle?
Please contact us for the current HOA fee, payment schedule, and HOA management company contact information. Bay Isle is a deed-restricted subdivision, and HOA dues typically cover common-area maintenance and architectural review.
Is there a CDD fee in Bay Isle?
Bay Isle is an established southern Winter Garden subdivision predating the Horizon West master-plan era and is not expected to carry a Community Development District assessment. Confirm against current Orange County property tax records before closing.
What schools serve Bay Isle?
Bay Isle falls within Orange County Public Schools and is likely zoned for Whispering Oak Elementary, SunRidge Middle, and West Orange High based on its location in the Stoneybrook West / NW 34787 cluster, but Bay Isle is not explicitly listed in our reference school-zone mapping. Verify current attendance zones directly with OCPS before making a purchase decision.
Does Bay Isle have lake access?
Bay Isle sits adjacent to Black Lake but does not appear to be a lakefront community with HOA-managed lake access. Direct lake-access neighborhoods on Black Lake include Black Lake Park. Confirm with the HOA whether any community-owned lake access exists.
How close is Bay Isle to Winter Garden Village and AdventHealth Winter Garden?
Both Winter Garden Village at Fowler Groves and AdventHealth Winter Garden Hospital sit roughly two to three miles north of Bay Isle along the Daniels Road corridor — typically a 5 to 8 minute drive depending on traffic.
Is Bay Isle a gated community?
Bay Isle is not currently identified as a gated community in our hub data. Buyers seeking a gated environment in this part of Winter Garden typically look at Stoneybrook West across Black Lake.
How long is the drive from Bay Isle to Walt Disney World?
Walt Disney World is roughly a 15 to 20 minute drive from Bay Isle (about 10 miles) via SR 429, making the neighborhood convenient for Disney employees and families with annual passes.
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Realtor David MyersDavid Myers
Your Winter Garden
Neighborhood Expert
Call/Text: 407.801.3286
Winter Garden Home Buyers Guide

Winter Garden Areas

  • Downtown Winter Garden
  • Horizon West
  • Oakland
  • Winter Garden Village

Downtown Winter Garden Area Neighborhoods

  • Downtown Winter Garden
  • Brandy Creek
  • Chapin Station
  • Courtlea Oaks
  • Courtlea Park
  • Covington Chase
  • Crown Point Springs
  • Daniels Crossing
  • Fullers Crossing
  • Fullers Landing
  • Heritage Plant Street
  • Island Pointe
  • Kings Bay
  • Lake Cove Pointe
  • Lakeview Reserve
  • Lakeview Village Estates
  • Magnolia Wood
  • McAllister Landing
  • Oakglen Estates
  • Oaks at Brandy Lake
  • Park Place
  • Regal Pointe
  • Stanton Estates
  • Sterling Pointe
  • Timbercreek Pines
  • Traditions
  • Trails Winter Garden
  • Tuscany
  • Walkers Grove
  • Winter Oaks

Winter Garden Village Area Neighborhoods

  • Alexander Ridge
  • Amberleigh
  • Avalon Reserve
  • Avalon Ridge
  • Banana Bay Estates
  • Bay Isle
  • Belle Meade
  • Black Lake Park
  • Black Lake Preserve
  • Bradford Creek
  • Bronsons Landing
  • Canopy Oaks
  • Carriage Pointe
  • Cobblestone
  • Country Lakes
  • Cypress Reserve
  • Daniels Landing
  • Deerfield Place
  • Emerald Ridge
  • Estates Lakeview Preserve
  • Foxcrest
  • Glynwood
  • Grove Park
  • Grovehurst
  • Hickory Hammock
  • Johns Lake Pointe
  • Lake Roberts Landing
  • Lakeview Preserve
  • Orange Cove
  • The Orchard
  • Oxford Chase
  • Regency Oaks
  • Reserve Carriage Pointe
  • Roper Reserve
  • Sanctuary Twin Waters
  • Southern Pines
  • Stone Creek
  • Stoneybrook West
  • Sunset Lakes
  • Tilden Place
  • Twinwaters
  • Waterside
  • Westfield Lakes
  • Windermere Crossing
  • Windward Cay
  • Winter Grove
  • Wintermere Harbor
  • Wintermere Pointe
  • Woodbridge on Green

Horizon West Area Neighborhoods

  • Avalon Cove
  • Cove At Hamlin
  • Del Webb Oasis
  • Enclave at Hamlin
  • Encore at Ovation
  • Hamilton Gardens
  • Hamlin Pointe
  • Hamlin Reserve
  • Hamlin Ridge
  • Hawksmoor
  • Harvest at Ovation
  • Highland Ridge
  • Highlands Summerlake
  • Horizon Isle
  • Independence
  • Isles Of Lake Hancock
  • Lake Hancock Preserve
  • Lakeshore
  • Lakeside at Hamlin
  • Lake Star at Ovation
  • Lakeview Pointe
  • Latham Park
  • Mezzano
  • Northlake at Ovation
  • Orchard Hills
  • Orchard Park
  • Osprey Ranch
  • Overlook At Hamlin
  • Panther View
  • Parkview at Hamlin
  • Ravenna
  • Sanctuary at Hamlin
  • Serenade at Ovation
  • Silverleaf Oaks
  • Silverleaf Reserve
  • Storey Grove
  • Summerlake
  • Summerlake Groves
  • Tribute at Ovation
  • Waterleigh
  • Watermark
  • Westhaven Ovation
  • Wincey Groves
  • Winding Bay

Oakland Area Neighborhoods

  • Deer Island
  • Downtown Oakland
  • Hull Island
  • Johns Cove
  • Johns Landing
  • Lake Apopka Sound
  • Longleaf at Oakland
  • Oakland Hills
  • Oakland Park
  • Oakland Trails
  • Trailside Station
  • Tucker Oaks
  • Verde Park

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