$1,400,000
5314 Chiswick Circle
Belle Isle, FL 32812
Listing updated: September 3, 2026 at 5:22 PM ET
Listing courtesy of Berkshire Hathaway Homeservices Results Realty · Joseph Doher · MLS #O6438441 · Active · 407-203-0007Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history0 days on market
- Status: ActiveSep 3, 2026
- Listed$1,400,000Sep 2, 2026
- Price increased$1,400,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 0
- Subdivision
- Windsor Place Ph 01
- County
- Orange
- Year built
- 1993
- Living area
- 2,487 sq ft
- Price/sq ft
- $563
- Building area
- 3,444 sq ft (Public Records)
- Lot size
- 11,045 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- X (12095C0430F)
- Garage
- 3 spaces
- Pool
- Private pool
- Annual taxes
- $4,798 (2025)
- Parcel #
- 5314 CHISWICK CIR. BELLE ISLE, FL 32812
- Zoning
- R-1-AA
- MLS #
- O6438441
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Interior Details
- Bedrooms
- 4
- Full bathrooms
- 3
- Flooring
- Laminate, Tile
- Appliances
- Dishwasher, Electric Water Heater, Microwave, Range, Refrigerator
- Interior features
- Ceiling Fans(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
- Laundry
- Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
- Stories / Levels
- One
- Direction faces
- Northeast
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central, Electric
- Cooling
- Central Air
Parking
- Garage spaces
- 3
- Attached garage
- Yes
- Parking features
- Driveway, Garage Door Opener, Open
HOA & Financial
- HOA fee
- $346 / Annually
- Monthly HOA
- $29/mo
- Total monthly fees
- $29/mo
- Total annual fees
- $346
- HOA name
- Paula Butler / Sentry Management
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 8-12 Months
- Listing terms
- Cash, Conventional, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Please verify with the HOA.
- Approval process
- Please verify with the HOA.
Exterior & Construction
- Exterior features
- Private Yard, Rain Gutters, Sidewalk
- Construction materials
- Block, Stucco
- Roof
- Shingle
- Foundation
- Slab
- Pool
- Private pool
- Water view
- Yes
- Road surface
- Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- BB/HS Internet Available, Cable Available, Electricity Connected, Sewer Connected, Water Connected
Community
- Pets allowed
- Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Living Room | First | 15x17 |
| Dining Room | First | 12x15 |
| Kitchen | First | 14x10 |
| Family Room | First | 17x14 |
| Primary Bedroom | First | 13x17 |
| Bedroom 2 | First | 12x14 |
| Bedroom 3 | First | 14x12 |
| Bedroom 4 | First | 13x11 |
Listing Details
- Listing date
- 2026-08-26
- On market date
- 2026-09-02
- Original list price
- $1,400,000
- Occupant type
- Owner
- MLS area
- 32812 - Orlando/Conway / Belle Isle
- Listing AOR
- Orlando Regional
- Status changed
- 2026-09-03
- Tax legal description
- WINDSOR PLACE PHASE 1 30/28 LOT 24
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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.
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Listing provided by Stellar MLS
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively 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.
Based on information submitted to the MLS GRID as of September 3, 2026 at 5:22 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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