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$1,400,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 2,487 Sq. Ft.
  • Updated 8 days ago
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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.

Full Property Details for 5314 Chiswick Cir

General

  • Price: $1,400,000
  • HOA FEE: $29/month
  • HOA FEE FREQ.: Annually
  • Taxes: $4,798 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6438441
  • Updated: 9/3/2026
  • Added to Site: 10 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 8
  • Interior Features: Ceiling Fan(s), Kitchen and Family Room Combination, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Family Room, Wood Burning
  • Appliances: Dishwasher, Electric Water Heater, Microwave, Range, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Laminate, Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 4

Other Rooms

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

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Deck, In Ground, Outside Bath Access, Screen Enclosure
  • Spa: Yes
  • Spa Description: Heated, In Ground

Exterior

  • Exterior Features: French Doors, Private Yard, Rain Gutters, Sidewalk, Sliding Doors
  • Deck/Patio: Covered, Deck, Screened
  • Porch/Patio/Deck: Covered, Deck, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3
  • Parking Features: Driveway, Garage Door Opener, Open

Location

  • Area: 32812 - Orlando/Conway / Belle Isle
  • County: Orange
  • Development Name: 32812 - Orlando/Conway / Belle Isle
  • Subdivision: WINDSOR PLACE PH 01
  • Driving Directions: From Conway Rd, turn onto Hoffner Ave traveling West, turn left onto Wadsworth Ave, right onto Chiswick Cir, and follow around until the homes appear on your right.
  • Direction Faces: Northeast

School Information

  • Elementary School: Shenandoah Elem
  • Middle School: Conway Middle
  • High School: Oak Ridge High

Community

  • Community Name: 32812 - Orlando/Conway / Belle Isle
  • Association: Yes
  • Assoc. Name: Paula Butler / Sentry Management
  • Pet Restrictions: Please verify with the HOA.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Sewer Connected, Water Connected

Structural Information

  • Architectural Info: Ranch
  • Architectural Style: Ranch
  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 2,487
  • Sq. Ft. Source: Public Records
  • Year Built: 1993

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.25
  • Lot Size (Sq. Ft.): 11,045
  • Lot Size: 11045
  • Frontage: Street Paved
  • Street/Road Desc.: Paved
  • Fencing (Description): Fenced, Other

Water Features

  • Water View: Yes

Financial Considerations

  • Association Fee: $346
  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $4,798
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: WINDSOR PLACE PHASE 1 30/28 LOT 24
  • Flood Zone Info: X
  • APN: 5314 CHISWICK CIR. BELLE ISLE, FL 32812
  • Property ID: 5314 CHISWICK CIR. BELLE ISLE, FL 32812

Listed by Berkshire Hathaway Homeservices Results Realty

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Listing agent

— 5314 Chiswick Cir —

  • Berkshire Hathaway Homeservices Results 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 5314 Chiswick Cir

School District:Orange County School District
NameGradesDistance
Shenandoah Elementary School, Orlando, FL
4827 Conway Road, Orlando, FL 32812
PK-50.6 mi
Conway Middle School
4600 Anderson Road, Orlando, FL 32812
6-81.7 mi
Oak Ridge High School
700 West Oak Ridge Road, Orlando, FL 32809
9-123 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5314 Chiswick Cir Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/02/2026
Listed
$1,400,000
311.76%
MLS
7/12/2004
Sold
$340,000
—
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 5314 Chiswick Cir

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,798
5%
$313,220
6%
2024
$4,573
4%
$296,390
3%
2023
$4,415
5%
$287,757
6%
2021
$4,213
-2%
$271,239
-3%
2022
$4,300
2%
$279,376
4%
2021
$4,213
2%
$267,494
2%
2019
$4,114
1%
$261,480
2%
2018
$4,069
2%
$256,605
2%
2017
$3,974
—
$251,327
2%
2016
$3,963
-2%
$246,158
1%
2015
$4,024
1%
$244,447
1%
2014
$3,995
2%
$242,507
2%
2013
$3,928
—
$238,923
—
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.

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Listed by Berkshire Hathaway Homeservices Results Realty

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5314 Chiswick Circle, Belle Isle, FL 32812 (MLS# O6438441) is a Single Family property with 4 bedrooms and 3 full bathrooms. 5314 Chiswick Circle is currently listed for $1,400,000 and was received on September 02, 2026. Want to learn more about 5314 Chiswick Circle? Do you have questions about finding other Single Family real estate for sale in Belle Isle? You can browse all Belle Isle real estate or contact a Coldwell Banker agent to request more information.

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