Under contract-accepting backup offers. Two stories, two bedrooms, two and a half baths, with the boring expensive stuff already handled. NEW roof overhead, NEW AC, NEW hot water heater, special assessment already paid, NEW living room flooring downstairs, NEW carpet up, and FRESH paint throughout. The first floor opens into a foyer that gives way to a full dining room on one side and a kitchen with breakfast bar seating on the other, both flanking a living room that stretches to back sliders. A second set of sliders off the front leads to a private patio, so you get cross-breeze and two outdoor spots before you even head upstairs. A half bath sits tucked off the kitchen for guests. Upstairs holds two true primary suites, each with its own full bathroom and its own private balcony. One faces the front, one faces the back, both have walk-in closets, and the laundry closet lives upstairs where the laundry actually is. Windsor Pines comes with a community pool and a playground, and the location does the rest of the work. You’re a few minutes from The Loop, where the grocery run, the dinner reservation, and the movie all happen in one parking lot. Ten minutes to downtown Kissimmee and the lakefront, straight onto Osceola Parkway or the Turnpike when you need to be elsewhere, and about fifteen minutes from the Disney gates when you don’t. Two primaries. Two porches. Two private balconies. One opportunity.
Property Details
Price:
$175,000
MLS #:
O6403991
Status:
Active Under Contract
Beds:
2
Baths:
2.5
Type:
Condo
Subtype:
Condominium
Subdivision:
WINDSOR PINES 1 CONDO
Neighborhood:
34741kissimmeedowntowneast
Listed Date:
May 1, 2026
Finished Sq Ft:
1,290
Total Sq Ft:
1,560
Lot Size:
806 sqft / 0.02 acres (approx)
Year Built:
1982
See this Listing
Schools
Elementary School:
Highlands Elem
Middle School:
Kissimmee Middle
High School:
Osceola High School
Interior
Appliances
Electric Water Heater, Range, Refrigerator
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Laminate, Tile
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Kitchen/Family Room Combo, Open Floorplan, PrimaryBedroom Upstairs, Solid Surface Counters, Thermostat, Walk-In Closet(s)
Laundry Features
Inside
Levels
Two
Exterior
Association Amenities
Park, Playground, Pool, Recreation Facilities
Community Features
Association Recreation – Owned, Buyer Approval Required, Community Mailbox, Deed Restrictions, Park, Playground, Pool, Sidewalks
Construction Materials
Block, Concrete, Stucco
Direction Faces
South
Exterior Features
Balcony, Lighting, Rain Gutters, Sidewalk, Sliding Doors
Fencing
Fenced
Lot Features
Landscaped, Sidewalk
Open Parking YN
1
Parking Features
Assigned, Ground Level, Guest, Open
Patio And Porch Features
Covered, Rear Porch
Roof
Shingle
Security Features
Smoke Detector(s)
Financial
HOA Fee
$375
HOA Fee Frequency
Monthly
HOA Includes
Common Area Taxes, Community Pool, Maintenance Structure, Maintenance Grounds, Manager, Pool Maintenance, Recreational Facilities, Trash, Water
HOA Name
Association Management Group of CFL/Melanie Ault
HOA Phone
(407) 847-9950
Tax Year
2025
Taxes
$992
Map
Community
- Address1329 WINDSOR DRIVE KISSIMMEE FL
- SubdivisionWINDSOR PINES 1 CONDO
- CityKISSIMMEE
- CountyOsceola
- Zip Code34741
Subdivisions in KISSIMMEE
- Association of Poinciana Villages
- BELLALAGO
- BELLAVIDA PH 01
- COMPASS BAY
- EAGLE LAKE PH 1
- EAST PALM RESORT CONDO
- MargaritaVille
- POINCIANA NBRHD 5 NORTH VILL 3
- POINCIANA SUBDIVISION NBRHD 5 NORTH VIL 3
- POINCIANA VLG 2 NBHD 1
- ROLLING OAKS PH 7
- Siesta Lago
- SONOMA RESORT AT TAPESTRY PH 1
- STOREY CREEK PH6
- STOREY LAKE TR K
- SUMMERVILLE RESORT
- VENTURA AT WINDSOR HILLS CONDO PH 1
Market Summary
Property Summary
- Located in the WINDSOR PINES 1 CONDO subdivision, 1329 WINDSOR DRIVE KISSIMMEE FL is a Condo for sale in KISSIMMEE, FL, 34741. It is listed for $175,000 and features 2 beds, 3 baths, and has approximately 1,290 square feet of living space, and was originally constructed in 1982. The current price per square foot is $136. The average price per square foot for Condo listings in KISSIMMEE is $203. The average listing price for Condo in KISSIMMEE is $247,021. To schedule a showing of MLS#o6403991 at 1329 WINDSOR DRIVE in KISSIMMEE, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of SERHANT. 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 InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. 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. 1329 WINDSOR DRIVE
KISSIMMEE, FL
