Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$890,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 3,779 Sq. Ft.
See This Home
Save This Home
See This Home
Save This Home
Beautifully maintained pool home in the gated community of Bay Isle. This spacious home is set on a luscious lot offering ample privacy and has that true Florida feel. This home has a lot of space and the floor plan is fully functional for a family, and great for entertaining. The Primary Suite is located on the main floor. Once you enter the 2nd floor you will find yourself in the cinema, where you can watch projected movies with the family on a 108" mounted screen. The remaining three bedrooms are on the second floor and divided by the loft and cat walk. Bedroom 2 is a guest suite with a full, private bathroom while bedroom 3 and 4 share a roomy Jack and Jill bath. The epicenter to most homes is the kitchen. This kitchen has 42" cabinets alone with ample counter space. The pool area with a southern exposure allows for sun on the pool for most of the day. This property backs up to a conservation area which provides the utmost privacy on the large screened-in lanai. This truly is a fantastic home with a lot to offer, and it's located in Bay Isle - a small, prestigious, gated community located less than 30 minutes to Disney and Orlando International Airport. Community features include: access to Black Lake, a great shaded playground, walking trail, easy access by foot or car to Winter Garden Village, neighborly neighbors and so much more..quite possibly the finest neighborhood in the area. Close to all major highways leading to Orlando or all Entertainment that makes Central Florida famous.

Full Property Details for 14321 Hampshire Bay Cir

General

  • Price: $890,000
  • HOA FEE: $158/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $10,699 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6339534
  • Updated: 1/2/2026
  • Added to Site: 137 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 13
  • Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Vaulted Ceiling(s), Walk-In Closet(s)
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer
  • Flooring: Carpet, Ceramic Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Electric Dryer Hookup, Laundry Room, Washer Hookup

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Gunite, In Ground, Lighting, Pool Sweep, Screen Enclosure
  • Security/Safety: Security System, Smoke Detector(s)

Exterior

  • Exterior Features: Irrigation System, Lighting, Shade Shutter(s), Sidewalk, Sprinkler Metered

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: BAY ISLE 48 17
  • Driving Directions: From Florida's Turnpike N take exit 267A Tampa, then merge to FL-429 S and take exit 19 for County Rd 535/Winter Garden Vineland Rd. At the traffic circle, take the 2nd exit and stay on Winter Garden Vineland Rd, then make a left to Bristol Isle Ln, then make a left to Hampshire Bay Cir the house will be on the left.
  • Direction Faces: North

School Information

  • Elementary School: Sunrise Elem
  • Middle School: SunRidge Middle
  • High School: West Orange High

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Deed Restrictions, Gated Community - No Guard, Park, Playground, Sidewalks
  • Association: Yes
  • Assoc. Name: Sindi Kelin-Hamil
  • Pet Restrictions: Please refer to HOA Documents

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Heat Pump

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Available, Public, Sprinkler Meter, Underground Utilities

Structural Information

  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Windows: Shutters, Window Treatments
  • Stories/Levels: Two
  • Square Feet: 3,779
  • Sq. Ft. Source: Public Records
  • Year Built: 2002

Lot Features

  • Lot Size (Acres): 0.34
  • Lot Size (Sq. Ft.): 14,832
  • Lot Size: 14832
  • Street/Road Desc.: Asphalt

Financial Considerations

  • Association Fee: $475
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • Tax Amount: $10,699.27
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: BAY ISLE 48/16 LOT 13
  • Flood Zone Info: X
  • APN: 342227016200130
  • Property ID: 342227016200130
  • Block/Lot/Section: 00/00

Listed by Corcoran Premier Realty

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 14321 Hampshire Bay Cir —

  • Corcoran Premier Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 14321 Hampshire Bay Cir

School District:Orange County School District
NameGradesDistance
Sunridge Elementary School
14455 Sunridge Boulevard, Winter Garden, FL 34787
PK-50.9 mi
SunRidge Middle School
14955 Sunridge Boulevard, Winter Garden, FL 34787
6-80.9 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-122 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 14321 Hampshire Bay Cir Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/02/2026
Price Reduced
$890,000
-3.26%
MLS
11/16/2025
Price Reduced
$920,000
-2.65%
MLS
10/01/2025
Price Reduced
$945,000
-3.08%
MLS
9/03/2025
Listed
$975,000
103.12%
MLS
1/30/2015
Sold
$480,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 14321 Hampshire Bay Cir

Year
Property Taxes
Change
Tax Assessment
Change
2024
$10,699
—
$686,692
-7%
2024
$10,699
9%
$738,823
7%
2023
$9,825
29%
$691,509
47%
2021
$7,629
-13%
$469,020
-21%
2022
$8,734
14%
$592,625
30%
2021
$7,629
4%
$457,187
4%
2019
$7,337
8%
$440,392
9%
2018
$6,811
3%
$403,849
3%
2017
$6,589
—
$392,187
3%
2016
$6,558
-11%
$382,173
-8%
2015
$7,343
7%
$415,053
10%
2014
$6,835
12%
$377,321
10%
2013
$6,089
—
$343,019
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 14321 Hampshire Bay Cir

$
Down Payment
%
$
%

$
$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Corcoran Premier Realty

Similar Properties near 14321 Hampshire Bay Cir

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

11145 Hollow Bay dr, Winter Garden, FL 34787 - Photo 1
$914,271

11145 Hollow Bay dr  Winter Garden, FL 34787

  • Single Family
  • Active
  • Updated 12 days ago
  • 4
    Beds
  • 5
    Total Baths
  • 3,327
    Sq. Ft.
Listed by Dr Horton Realty Of Central Florida Llc
15713 Sweet Limetta Dr, Winter Garden, FL 34787 - Photo 1
$850,000

15713 Sweet Limetta Dr  Winter Garden, FL 34787

  • Single Family
  • Active
  • Updated 9 days ago
  • 4
    Beds
  • 5
    Total Baths
  • 3,377
    Sq. Ft.
Listed by Premier Sothebys Int'l Realty
15372 Gilligan Ct, Winter Garden, FL 34787 - Photo 1
$884,500

15372 Gilligan Ct  Winter Garden, FL 34787

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 2,781
    Sq. Ft.
Listed by Wra Business & Real Estate
18049 Millhouse Way, Winter Garden, FL 34787 - Photo 1
$882,200

18049 Millhouse Way  Winter Garden, FL 34787

  • Single Family
  • Active
  • Updated 10 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,327
    Sq. Ft.
Listed by Dr Horton Realty Of Central Florida Llc

Just Listed near 14321 Hampshire Bay Cir

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

17016 Hillcrest View Dr, Montverde, FL 34756 - Photo 1 Just Listed
$324,999

17016 Hillcrest View Dr  Montverde, FL 34756

  • Single Family
  • Active
  • Updated 18 hours ago
  • 3
    Beds
  • 1
    Total Bath
  • 1,444
    Sq. Ft.
Listed by Charles Rutenberg Realty Orlando
17414 Pesce Loop, Montverde, FL 34756 - Photo 1 Just Listed
$2,811,628

17414 Pesce Loop  Montverde, FL 34756

  • Single Family
  • Active
  • Updated 15 hours ago
  • 5
    Beds
  • 5
    Total Baths
  • 4,254
    Sq. Ft.
Listed by Orlando Tbi Realty Llc
16650 Bolsena Dr, Montverde, FL 34756 - Photo 1 Just Listed
$1,591,995

16650 Bolsena Dr  Montverde, FL 34756

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 5
    Total Baths
  • 3,878
    Sq. Ft.
Listed by Orlando Tbi Realty Llc
2754 Purple Mdw Ct, Minneola, FL 34715 - Photo 1 Just Listed
$575,000

2754 Purple Mdw Ct  Minneola, FL 34715

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,620
    Sq. Ft.
Listed by Century 21 Carioti

Price Reduced near 14321 Hampshire Bay Cir

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

17416 Eve Dr, Montverde, FL 34756 - Photo 1 Price Reduced
-$10,000 (-7.19%)
$129,000

17416 Eve Dr  Montverde, FL 34756

  • Mobile Home
  • Active
  • Updated 3 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 840
    Sq. Ft.
Listed by Trinity Real Estate Sales Llc
17660 County Rd 455, Montverde, FL 34756 - Photo 1 Price Reduced
-$10,000 (-1.38%)
$714,999

17660 County Rd 455  Montverde, FL 34756

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,593
    Sq. Ft.
Listed by Lpt Realty, Llc
16716 Caravaggio Loop, Montverde, FL 34756 - Photo 1 Price Reduced
-$20,000 (-1.55%)
$1,270,000

16716 Caravaggio Loop  Montverde, FL 34756

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,682
    Sq. Ft.
Listed by Keller Williams Realty Partners Sw
15727 Vetta Dr, Montverde, FL 34756 - Photo 1 Price Reduced
-$40,000 (-3.67%)
$1,050,000

15727 Vetta Dr  Montverde, FL 34756

  • Single Family
  • Active
  • Updated 1 day ago
  • 5
    Beds
  • 4
    Total Baths
  • 3,083
    Sq. Ft.
Listed by Bella Collina Real Estate Co

Recent Sales near 14321 Hampshire Bay Cir

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

14003 Hampshire Bay Cir, Winter Garden, FL 34787 - Photo 1 Sold
$890,000

14003 Hampshire Bay Cir  Winter Garden, FL 34787

  • Single Family
  • Closed
  • 4
    Beds
  • 5
    Total Baths
  • 4,015
    Sq. Ft.
Listed by Buyer Rebates Realty
Sold by American Dream House Realty
2842 Balforn Tower, Winter Garden, FL 34787 - Photo 1 Sold
$790,000

2842 Balforn Tower  Winter Garden, FL 34787

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 3,219
    Sq. Ft.
Listed by Watson Realty Corp
Sold by Keller Williams Elite Partners Iii Realty
13524 Glynshel Dr, Winter Garden, FL 34787 - Photo 1 Sold
$855,000

13524 Glynshel Dr  Winter Garden, FL 34787

  • Single Family
  • Closed
  • 5
    Beds
  • 4
    Total Baths
  • 3,717
    Sq. Ft.
Listed by Exp Realty Llc
Sold by Carmen Quintana
13609 Glynshel Dr, Winter Garden, FL 34787 - Photo 1 Sold
$900,000

13609 Glynshel Dr  Winter Garden, FL 34787

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,923
    Sq. Ft.
Listed by Exp Realty Llc
Sold by Dalton Wade Inc

14321 Hampshire Bay Circle, Winter Garden, FL 34787 (MLS# O6339534) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 14321 Hampshire Bay Circle is currently listed for $890,000 and was received on September 03, 2025. Want to learn more about 14321 Hampshire Bay Circle? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

Tour this property