433 GILBERT ROAD
Winter Park, FL 32792
$660,000
A RARE SECOND CHANCE IN WINTER PARK PINES! This beautifully updated three-bedroom, two-bath POOL home is available again, giving one fortunate buyer another opportunity to make it theirs. This beautifully updated and spacious home, offering nearly 1,800 square feet of thoughtfully designed living space on a spacious lot backing to a peaceful conservation easement. Featuring separate living and family rooms, a remodeled kitchen, and an exceptional outdoor retreat, this inviting home is perfectly designed for both everyday living and entertaining.
From the moment you arrive, the classic brick entry creates a warm first impression. Inside, the flexible floor plan provides plenty of space to gather, relax, work from home, or host guests. Laminate wood flooring and updated baseboards (2022) complement plantation shutters, recessed lighting, and ceiling fans throughout. Multiple storage closets add everyday functionality, while updated windows and French doors fill the home with natural light and seamlessly connect the indoor and outdoor living spaces.
The remodeled kitchen (2021) features crisp white shaker cabinetry, quartz countertops, a subway tile backsplash, stainless steel appliances, an oversized stainless-steel sink, and a breakfast bar with seating for four. A dedicated coffee bar and pantry add convenience, while the large bay window overlooks the pool and private backyard, creating the perfect backdrop for everyday living.
The spacious primary suite offers a walk-in closet and ceiling fan. Its ensuite bathroom, renovated in 2022, features large marble-look tile, a double vanity with quartz countertops, and a beautifully updated walk-in ...
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Listing Courtesy of: KELLER WILLIAMS WINTER PARK
407-545-6430
Buyer Represented by: BHHS FLORIDA REALTY
| Listing Id: | O6428430 |
|---|---|
| List Price: | $669,900 |
| Close Price: | $660,000 |
| Close Date: | 2026-11-13 |
| Property Type: | Residential |
| Property Sub Type: | Single Family Residence |
| Status: | Closed |
| Bedrooms Total: | 3 |
| Bathrooms Full: | 2 |
| Living Area: | 1,800 |
| Tax Annual Amount: | $4,032 |
| Lot Size Square Feet: | 9,230 |
| Lot Size Acres: | 0.21 |
| Architectural Style: | Ranch |
| Waterfront?: | No |
| City: | Winter Park |
| County Or Parish: | Orange |
| Subdivision Name: | Winter Park Pines |
| Postal Code: | 32792 |
| Year Built: | 1965 |
| Additional Parcels?: | No |
| Appliances: | Dishwasher, Disposal, Microwave, Range, Refrigerator |
| Association Amenities: | Golf Course, Pickleball Court(s), Playground, Pool, Tennis Court(s), Trail(s) |
| Attached Garage?: | Yes |
| Bathrooms Total Integer: | 2 |
| Building Area Source: | Public Records |
| Building Area Total: | 2754 |
| Building Area Units: | Square Feet |
| Carport?: | No |
| Direction Faces: | East |
| Foundation Details: | Slab |
| Construction Materials: | Block |
| Cooling: | Central Air |
| Directions: | From downtown Winter Park, head east on Fairbanks Ave. Turn right on N Ranger Road, right on Bower Road and wind the left on Gilbert Road. 433 Gilbert Road will be on your right. |
| Elementary School: | Brookshire Elem |
| Exterior Features: | Private Mailbox, Rain Gutters, Sidewalk |
| Fencing: | Fenced, Vinyl |
| Flooring: | Ceramic Tile, Laminate, Terrazzo |
| Furnished: | Unfurnished |
| Garage Spaces: | 2 |
| Garage?: | Yes |
| Community Features: | Park, Playground, Pool, Sidewalks, Tennis Court(s) |
| Heating: | Electric |
| High School: | Winter Park High |
| Interior Features: | Built-in Features, Ceiling Fans(s), Eat-in Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s) |
| Laundry Features: | In Garage |
| Levels: | One |
| Ownership: | Fee Simple |
| Living Area Source: | Public Records |
| Living Area Units: | Square Feet |
| Lot Features: | Landscaped, Near Golf Course, Sidewalk, Paved, Unincorporated |
| Lot Size Acres: | 0.21 |
| Postal Code Plus4: | 4826 |
| Middle Or Junior School: | Glenridge Middle |
| MLS Area Major: | 32792 - Winter Park/Aloma |
| MLS Area Major: | 32792 - Winter Park/Aloma |
| Original List Price: | $675,000 |
| Other Equipment: | Irrigation Equipment |
| Parcel Number: | 09-22-30-9664-04-310 |
| Parking Features: | Driveway, Garage Door Opener, On Street, Workshop in Garage |
| Patio And Porch Features: | Covered, Deck, Front Porch, Porch, Rear Porch, Screened |
| Pets Allowed: | Cats OK, Dogs OK, Yes |
| Pool Features: | Gunite, In Ground, Screen Enclosure |
| Township: | 22 |
| Road Surface Type: | Asphalt, Paved |
| Roof: | Shingle |
| Listing Terms: | Cash, Conventional, FHA, VA Loan |
| Tax Year: | 2025 |
| Security Features: | Security System, Security System Owned |
| Senior Community?: | No |
| Sewer: | Public Sewer |
| Special Listing Conditions: | None |
| State Or Province: | FL |
| Association?: | No |
| Utilities: | BB/HS Internet Available, Electricity Connected, Sewer Connected, Water Connected |
| View: | Trees/Woods |
| Water Source: | Public |
| Public Survey Range: | 30 |
| Public Survey Section: | 09 |
| Zoning: | R-1A |
| Possession: | Close Of Escrow |
| Spa?: | No |
| Vegetation: | Mature Landscaping, Trees/Landscaped |
| Window Features: | Shutters |
| Additional Lease Restrictions: | Buyer to verify lease restrictions with Orange County. |
| Additional Rooms: | Family Room |
| Additional Water Information: | Public Boat Ramp to Winter Park Chain of Lakes located less than 10 minutes drive. |
| Alternate Key Folio Num: | 09-22-30-9664-04-310 |
| Amenities Additional Fees: | Winter Park Pines 18 is a Public Golf Course, membership not required. Cady Way Pool also has membership availability. |
| Available For Lease Yn: | Yes |
| Backups Requested Yn: | Yes |
| Building Area Total Srch Sq M: | 255.85 |
| Calculated List Price By Calcula: | 372.17 |
| Cddyn: | No |
| Dprurl: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6428430?w=Agent&skip_sso=true |
| Dprurl 2: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6428430?w=Customer |
| Dpryn: | Yes |
| Exist Lse Tenant Yn: | No |
| Flood Zone Code: | X |
| Flood Zone Date: | 2009-09-25 |
| Flood Zone Panel: | 12095C0255F |
| Green Verification Count: | 0 |
| Homestead Yn: | Yes |
| Lease Restrictions Yn: | Yes |
| Listing Exclusion Yn: | No |
| Living Area Meters: | 167.23 |
| Lot Size Square Meters: | 857 |
| Minimum Lease: | 8-12 Months |
| Pet Restrictions: | Buyer to verify pet restrictions with Orange County. |
| Property Description: | Walk-Up |
| Realtor Info: | As-Is, See Attachments, Sign |
| Room Count: | 10 |
| Sdeo yn: | No |
| Total Acreage: | 0 to less than 1/4 |
| Unit Number Yn: | No |
| Water Access Yn: | No |
| Water Extras Yn: | No |
| Water View: | No |
| Association 2 Yn: | 0 |
| Attribution Contact: | 407-545-6430 |
| Originating System Name : | Stellar MLS |
| In Law Suite Yn: | No |
| Green Energy Generation Yn: | No |
| Listing Contract Date: | 2026-07-25 |
| Fireplace?: | No |
| Pool Private?: | Yes |
| New Construction?: | No |
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Property Last Updated: November 14, 2026 03:03 AM - ET
