Bay Isle Homes for Sale

14423 Hampshire Bay Circle, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Bay Isle 48 17 SubDv. ⋅ 34787 Zip Code

Luxury Living in Winter Garden – 14423 Hampshire Bay Circle 4 Bedrooms | 3.5 Bathrooms | Approximately 3,000 Sq. Ft. | Heated Saltwater Pool & Spa Welcome to 14423 Hampshire Bay Circle, where modern elegance meets luxury Florida living in the highly desirable Winter Garden area. This beautifully appointed residence offers approximately 3,000 square feet of sophisticated living space, featuring 4 spacious bedrooms, 3.5 bathrooms, and an impressive collection of high-end finishes throughout. At the heart of the home is a gourmet chef’s kitchen, thoughtfully designed with premium appliances, including a Sub-Zero refrigerator, professional-style gas range, and upscale finishes that create the perfect setting for both everyday living and entertaining. Step outside into your very own private resort-style oasis, featuring a heated saltwater swimming pool and relaxing spa, ideal for enjoying Florida’s beautiful weather year-round. Whether hosting unforgettable gatherings or unwinding after a long day, this outdoor retreat delivers the ultimate luxury lifestyle. Inside, the home offers an inviting combination of contemporary design, generous living areas, and refined details. The spacious primary suite provides a comfortable private retreat, while the additional bedrooms offer flexibility for family, guests, or a home office. Additional highlights include premium appliances, a high-end washer and dryer, and thoughtfully designed spaces that balance functionality with elegance. Conveniently located in Winter Garden, Florida, this exceptional property offers access to shopping, dining, entertainment, and major roadways while providing the comfort of an upscale residential setting. More than just a home, this is an opportunity to experience luxury, comfort, and resort-style living every day. Schedule your private showing and discover everything this remarkable property has to offer.

14423 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 to	Time	Miles
Downtown Orlando	23 min	16.7
Walt Disney World	22 min	18.0
Orlando International Airport	28 min	25.1
Universal Orlando	23 min	15.6

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

Useful local links

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 November 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

268 daysMedian days to contract

2Homes sold in 12 months

Sale prices ran from $780,000 to $1,120,200.

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 sale50%

Conventional 1 sale50%

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 7 November 2025 through 2 November 2026, refreshed monthly and current as of November 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.