Homes In Orlando For Sale Search
$870,000
4 Beds ⋅ 5 Baths ⋅ Bay Isle 48 17 SubDv. ⋅ 34787 Zip Code
Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers home offers a rare combination of sophisticated design, thoughtful craftsmanship, and resort-caliber amenities — all within walking distance of Winter Garden Village and AdventHealth. A soaring two-story foyer and grand living room welcome you with an abundance of natural light streaming through an exceptional array of windows — a hallmark of the home's open, airy character. At the heart of the home lies a commanding gourmet kitchen, completely updated in 2021 with quartz countertops, a handsome marble backsplash, and a professional-grade induction cooktop with custom hood vent. Rich cherry cabinetry, a wall oven, built-in microwave, generous center island, and extensive counter space are all finished with elegant crown molding — flowing seamlessly into the expansive family room with French doors opening to the outdoor living area. The main-level primary suite is a true sanctuary, featuring rich laminate flooring, serene pool and spa views, and architectural transom windows that elevate the abundant natural light. Two oversized walk-in closets with custom built-in organization systems flank a luxurious en-suite bath complete with a dual-sink vanity, deep soaking tub, and a spa-inspired walk-in shower. Upstairs, three additional bedrooms offer both privacy and connection. A private en-suite bedroom with generous walk-in closet is discreetly separated via a catwalk, while two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas and a shared water closet and tub/shower. Your private home theater is fully equipped for the ultimate cinematic experience — theater seating, a 4K HD projector, Dolby surround sound, all convey with the home. The space also offers flexibility as a fifth bedroom. A loft game area and additional half bath complete the upper level's entertainment suite. Step outside to your private oasis: a sparkling pool and spa enclosed within an oversized screened lanai, complete with an outdoor shower and multiple seating areas ideal for effortless outdoor entertaining. An additional state of the art Clearlight 2 person infrared sauna provides relaxation, and rejuvenation. A three-car split garage — two bays connected to the main home, a third independently accessed — provides exceptional versatility for a workshop, boat storage, collector vehicles, or extra storage. A dedicated EV charging station is already in place. Eight-foot interior doors and extensive crown molding throughout reinforce the home's refined aesthetic. New roof (2019) · Pool pump (2018) · Full kitchen renovation (2021) Bay Isle's gated grounds feature a park, playground, walking trail, and a fishing pier on Black Lake — offering a tranquil, connected lifestyle just minutes from major roadways and every amenity Winter Garden has to offer.

14411 Hampshire Bay Circle, Winter Garden
Start Your Search

Orange County › Winter Garden › Bay Isle

Bay Isle, Winter Garden

Bay Isle is a 2000s neighborhood in south Winter Garden, in the 34787 zip code. Homes are block and stucco. Most homes fall between about 2,400 and 4,000 square feet under air, the median lot is roughly a third of an acre, and a three car garage is standard.

Homes here carry an HOA, billed quarterly, typically around $320. Confirm the figure on a specific parcel before relying on it.

What the homes are

  • Built Essentially all built in the 2000s.
  • Construction Block and stucco. Shingle roofs are near universal.
  • Size Most homes fall between about 2,400 and 4,000 square feet under air.
  • Bedrooms Four bedrooms is the most common plan.
  • Garage A three car garage is standard.
  • Lot The median lot is roughly a third of an acre.
  • HOA Billed quarterly, typically around $320. Confirm on a specific parcel before relying on it.

Where Bay Isle is

Bay Isle, centered at 28.526891, -81.592446. Drag to explore.
Street level, inside the neighborhood. Drag to look around.

Drive times below are measured on the road network from the center of Bay Isle, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.

Driving toTimeMiles
Downtown Orlando23 min16.7
Walt Disney World22 min18.0
Orlando International Airport28 min25.1
Universal Orlando23 min15.6

Public schools nearby

  • SunRidge Elementary School 12 min, 4.6 mi
  • Whispering Oak Elementary School 7 min, 2.7 mi
  • West Orange High School 6 min, 2.3 mi
  • Lake Whitney Elementary School 8 min, 3.3 mi

Private schools nearby

  • StarChild Academy Winter Garden 3 min, 1.2 mi
  • Winter Garden Christian Academy 5 min, 2.0 mi

Parks and recreation

  • Tildenville Park 9 min, 3.9 mi
  • North Edge Park 6 min, 2.5 mi
  • West Orange Dog Park 6 min, 2.8 mi
  • George Bailey Park 7 min, 3.1 mi

Groceries and errands

  • Target Grocery 4 min, 0.9 mi
  • A&E Grocery Store 9 min, 4.0 mi
  • Publix Super Market at West Point Commons 4 min, 1.8 mi
  • Armazém X Winter Garden 6 min, 1.9 mi

Nearest is not the same as zoned. The schools above are the closest ones to Bay Isle by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Orange County Public Schools before it matters to a decision.

Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in Bay Isle actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 2 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated September 2026.

Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.

What homes sold for in Bay Isle

$950,100Median sale price
$224Median per square foot
237 daysMedian days to contract
2Homes sold in 12 months

Sale prices ran from $780,000 to $1,120,200, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.

Seller concessions

50%Of sales included a seller credit
$5,000Typical credit when there was one
1 of 2Sales carrying a credit

A seller credit covers part of the buyer's closing costs and comes off the seller's proceeds, so the headline sale price overstates what the seller kept. Budget for it if you are selling, and ask for it if you are buying.

How buyers paid

Cash 1 sales50%
Conventional 1 sales50%

Cash was 50% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.

Questions about a specific home in Bay Isle, or want to know what yours would sell for?
Call or text Brenden Rendo at 407-616-9019 or send a message.

About this data. Source is the Stellar MLS feed for Bay Isle in Winter Garden, Orange County, covering closed sales from 25 September 2025 through 20 September 2026, refreshed monthly and current as of September 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.