THIS LISTING IS FOR THE SALE OF 5314 AND 5308 CHISWICK TOGETHER (the property next door) BY THE SAME OWNER. Rare opportunity to purchase two side-by-side single-family homes, and both have been beautifully maintained. Rare opportunity to own two side-by-side homes in Belle Isle’s highly sought-after Windsor Place community, minutes from Orlando International Airport and the Conway Chain of Lakes. Offered together at a slight discount by one seller, this pairing includes a 4-bed/3-bath, 2,487-sq-ft pond-front pool home with no rear neighbors and a 3-bed/2-bath, 2,146-sq-ft pond-view pool home. Both single-story residences feature desirable split-bedroom plans, vaulted ceilings, crown molding, wood-burning fireplaces, and French doors opening to backyard oases with screen-enclosed pools overlooking a tranquil pond, perfect for enjoying those glorious sunsets. The larger home has two ensuite bedrooms, a three-car garage, an extended deck, a covered lanai, a breakfast bar, and stainless-steel GE appliances. The second home shines with a renovated kitchen (granite, 42-inch soft-close cabinets, stainless-steel appliances, breakfast bar), a stunningly remodeled primary bath (freestanding tub, frameless rain-shower, quartz vanities), an oversized pool with raised spa and solar heating, and wrought-iron fencing that borders both properties, with the middle portion left open for easy adventures back and forth. Recent updates across both include new roofs (2022/2023), pool resurfacing (2022), whole-home replumbs (2022/2024), HVAC (2021), water heater (2024), and deck renovations (2022). Schedule your private showing today and experience this rare opportunity firsthand. Individual MLS listing #’s: O6435964 & O6435963. 5314 – All Furniture, decor, artwork, washer, and dryer are NEGOTIABLE. 5308 – Furniture and all items except for those on the rear patio are NEGOTIABLE. 2nd refrigerator DOES NOT CONVEY.
Property Details
Price:
$1,400,000
MLS #:
O6438441
Status:
Active
Beds:
4
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINDSOR PLACE PH 01
Neighborhood:
32812orlandoconwaybelleisle
Listed Date:
Sep 2, 2026
Finished Sq Ft:
2,487
Total Sq Ft:
3,444
Lot Size:
11,045 sqft / 0.25 acres (approx)
Year Built:
1993
See this Listing
Schools
Elementary School:
Shenandoah Elem
Middle School:
Conway Middle
High School:
Oak Ridge High
Interior
Appliances
Dishwasher, Electric Water Heater, Microwave, Range, Refrigerator
Bathrooms
3 Full Bathrooms
Cooling
Central Air
Flooring
Laminate, Tile
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
Laundry Features
Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
Levels
One
Exterior
Architectural Style
Ranch
Attached Garage YN
1
Construction Materials
Block, Stucco
Covered Spaces
3
Direction Faces
Northeast
Exterior Features
French Doors, Private Yard, Rain Gutters, Sidewalk, Sliding Doors
Fencing
Fenced, Other
Garage Spaces
3
Lot Features
Landscaped, Sidewalk
Open Parking YN
1
Parking Features
Driveway, Garage Door Opener, Open
Patio And Porch Features
Covered, Deck, Screened
Roof
Shingle
Spa Features
Heated, In Ground
View
Water
Financial
HOA Fee
$346
HOA Fee Frequency
Annually
HOA Name
Paula Butler / Sentry Management
HOA Phone
407-788-6700
Tax Year
2025
Taxes
$4,798
Map
Community
- Address5314 CHISWICK CIRCLE BELLE ISLE FL
- SubdivisionWINDSOR PLACE PH 01
- CityBELLE ISLE
- CountyOrange
- Zip Code32812
Subdivisions in BELLE ISLE
Market Summary
Current real estate data for Single Family in BELLE ISLE as of Sep 06, 2026
20
Single Family Listed
54
Avg DOM
342
Avg $ / SqFt
$937,084
Avg List Price
Property Summary
- Located in the WINDSOR PLACE PH 01 subdivision, 5314 CHISWICK CIRCLE BELLE ISLE FL is a Single Family for sale in BELLE ISLE, FL, 32812. It is listed for $1,400,000 and features 4 beds, 3 baths, and has approximately 2,487 square feet of living space, and was originally constructed in 1993. The current price per square foot is $563. The average price per square foot for Single Family listings in BELLE ISLE is $342. The average listing price for Single Family in BELLE ISLE is $937,084. To schedule a showing of MLS#o6438441 at 5314 CHISWICK CIRCLE in BELLE ISLE, FL, contact your CENTURY 21 Carioti agent at 2392986550.
Similar Listings Nearby
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 5314 CHISWICK CIRCLE
BELLE ISLE, FL
