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Jamie Deihl
REALTOR®
(719) 468-9744
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14039 Hampshire Bay Circle, Winter Garden, FL 34787

$819,900

86 Total Photos [Click to View All]

Property Description

Fully Renovated 4BR Luxury Home | Bay Isle Gated | Private Cinema | Grand Primary Suite | Corner Lot Fully renovated 4-bedroom, 3.5-bath plus additional upstairs half bath, home located in the desirable Bay Isle gated community in Winter Garden. Residents enjoy access to a private lake, park, sidewalks, and gated security. HOA covers landscaping, private roads, amenities, and security. This premium corner-lot property features an oversized paved courtyard with ample space for a future pool and custom outdoor living area, ample parking, irrigation system, rain gutters, and a whole-house water filtration system (owned, no lease). Spacious layout includes open kitchen/family room, living/dining room combo, extended loft, private cinema room with reclining theater seating, 120 screen, short-throw projector, and surround sound system, and enclosed lanai ideal for entertaining. Interior features include porcelain tile flooring in main living areas and kitchen, high ceilings, crown molding, solid wood cabinetry, solid surface countertops, walk-in closets, and showers in all full bathrooms. The grand primary suite on the main level features a spa-style bathroom with jetted soaking tub and dual shower, along with two walk-in closets and an exceptional bonus area with three separate rooms and independent entrance, currently used as additional closets, offering flexible potential for a home office, gym, studio, or private retreat. Recent updates include roof replaced in 2021 and three A/C units (one brand new) for enhanced efficiency and reliability. The floor plan offers: Primary suite on the main level Upstairs private suite with bathroom and walk-in closet Two additional upstairs bedrooms with shared full bathroom Additional upstairs half bath (powder room) Prime location near Winter Garden Village, new hospital, and just minutes from charming Downtown Winter Garden, with easy access to major highways, theme parks, and Orlando International Airport.

14039 Hampshire Bay Circle | MLS# O6274785

This single family home located at 14039 Hampshire Bay Circle, Winter Garden, FL 34787 is currently listed for sale with an asking price of $819,900. This property was built in 2006 and has 4 bedrooms and 3 full and 2 partial baths with 3801 sq. ft. Hampshire Bay Circle is located in the BAY ISLE 48 17 subdivision. Search BAY ISLE 48 17 real estate on jamiedeihl.watsonrealtycorp.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air, Attic Fan
Garage: 2 car attached
Heating: Central
Lot Size: 0.40 Acres
Roof Type: Shingle
Stories: 2.0
Taxes: $11,068
Year Built: 2006
Square Feet: 3,801

Amenities

Ceiling Fans(s)
Eat-in Kitchen
High Ceilings
Kitchen/Family Room Combo
Living Room/Dining Room Combo
Primary Bedroom Main Floor
Walk-In Closet(s)
Window Treatments
French Doors
Lighting
Rain Gutters

Feature Descriptions

Appliances: Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator
Community Features: Gated Community - Guard, Park, Playground, Sidewalks
Days on Site: 410
Directions: Take Winter Garden Vineland Rd to Hampshire Bay Cir Use the left lane to turn left onto Winter Garden Vineland Rd Slight left to stay on Winter Garden Vineland Rd At the traffic circle, take the 2nd exit and stay on Winter Garden Vineland Rd Turn left ont
Exterior: Block, Stucco
Flood Zone Code: x
Flooring: Tile, Vinyl
Foundation: Slab
HOA Fee: 141/ Monthly
HOA Y/N: Yes
Home Warranty Y/N: No
Listing Terms: Cash, Conventional, FHA, VA Loan
Lot Dimensions: 0.4
Other Equipment: Irrigation Equipment
Ownership: Fee Simple
Pets Allowed: Yes
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Sewer: Public Sewer
Showing Instructions: 24 Hour Notice, Appointment Only, Call Listing Agent
Special Sale Provisions: None
Utilities: Cable Available, Cable Connected, Sewer Available, Sewer Connected, Water Available, Water Connected
Water: Public
Water Access Y/N: No
Zoning: R-1

Listed By / Shown By

Listed By

Agency Name: SUMMERHILL REALTY GROUP LLC
Agency Contact: 407-963-8083

Shown By

Agent Name: Jamie Deihl
Agent Phone: (719) 468-9744
Agency Title: Watson Realty Corp., REALTORS ®

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Estimated Payment

$ 5,115.15 per month $3,953.68 Principal & Interest $922.33 Property Tax $239.14 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 03/10/2026. The listing information on this page last changed on 03/10/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 03/10/2026 12:42:09 AM EST) or GAMLS (last updated Mon 03/09/2026 11:14:58 PM EST) or Stellar MLS (last updated Tue 03/10/2026 12:29:11 AM EST) or SPC MLS (last updated Mon 03/09/2026 11:20:30 PM EST) or Martin MLS (last updated Mon 03/09/2026 11:38:19 PM EST) or Indian River MLS (last updated Mon 03/09/2026 11:30:27 PM EST) or Daytona MLS (last updated Mon 03/09/2026 11:36:51 PM EST) or Northeast Florida MLS (last updated Tue 03/10/2026 12:18:46 AM EST) or Beaches MLS (last updated Tue 03/10/2026 12:35:40 AM EST) or BORMLS (last updated Mon 03/09/2026 11:15:20 PM EST) or Golden Isles MLS (last updated Mon 03/09/2026 11:26:41 PM EST) or Amelia/Nassau MLS (last updated Mon 03/09/2026 11:25:21 PM EST) or Dixie Gilchrist Levy MLS (last updated Mon 03/09/2026 11:42:28 PM EST). Real estate listings held by brokerage firms other than Watson Realty Corp., REALTORS ® may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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