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Property Description
Welcome to this beautifully updated three-bedroom, two-bathroom pool 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 shower with a frameless glass enclosure. Two additional guest bedrooms and an updated full bathroom complete the bedroom wing. Step outside to the true centerpiece of the home. Backing to a conservation easement, the backyard offers a peaceful setting with enhanced privacy. The screened, in-ground chlorine pool was completely refreshed in 2025 with new tile, repaired beam, resurfacing, and new pool light. The lanai deck was also resurfaced, creating an ideal space for swimming, outdoor dining, and entertaining family and friends. The outdoor improvements continue with fresh landscaping completed in 2025, including new sod, a stone pathway, French drains for improved drainage, and an updated irrigation timer. The fully fenced backyard (2023) provides additional privacy for pets, play, and gatherings. Ideally located near Cady Way Trail and Winter Park Pines Golf Course, you'll also enjoy convenient access to Cady Way Park amenities, including a community pool, playground, tennis and pickleball courts, beach volleyball, and walking trails. AdventHealth Winter Park and the Crosby Wellness Center are just minutes away, while Rollins College, Full Sail University, UCF, and Orlando International Airport are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines modern updates, flexible living spaces, and a private backyard retreat in one of Winter Park's most desirable locations. ROOF - 2024 ELECTRICAL PANELS - 2021
Full Property Details
Full Property Details for 433 Gilbert Rd
General
- Price: $675,000
- Taxes: $4,032 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6428430
- Updated: 7/28/2026
- Added to Site: 2 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 10
- Interior Features: Built-in Features, Ceiling Fan(s), Eating Space In Kitchen, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s)
- Appliances: Dishwasher, Disposal, Microwave, Range, Refrigerator
- Furnishings: Unfurnished
- Flooring: Ceramic Tile, Laminate, Terrazzo
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: In Garage
Additional Information
- Shared Amenities: Golf Course, Pickleball Court(s), Playground, Pool, Tennis Court(s), Trail(s)
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, In Ground, Screen Enclosure
- Security/Safety: Security System, Security System Owned
Exterior
- Exterior Features: French Doors, Irrigation System, Private Mailbox, Rain Gutters, Sidewalk
- Deck/Patio: Covered, Deck, Front Porch, Porch, Rear Porch, Screened
- Porch/Patio/Deck: Covered, Deck, Front Porch, Porch, Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Driveway, Garage Door Opener, On Street, Workshop in Garage
Location
- Area: 32792 - Winter Park/Aloma
- County: Orange
- Development Name: 32792 - Winter Park/Aloma
- Subdivision: WINTER PARK PINES
- Driving 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.
- Direction Faces: East
School Information
- Elementary School: Brookshire Elem
- Middle School: Glenridge Middle
- High School: Winter Park High
Community
- Community Name: 32792 - Winter Park/Aloma
- Community Features: Park, Playground, Pool, Sidewalks, Tennis Court(s)
- Optional Amenities: Golf Course, Pickleball Court(s), Playground, Pool, Tennis Court(s), Trail(s)
- Pet Restrictions: Buyer to verify pet restrictions with Orange County.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Electricity Connected, Sewer Connected, Water Connected
Structural Information
- Architectural Info: Ranch
- Architectural Style: Ranch
- Exterior Const.: Block
- Roof: Shingle
- Windows: Shutters
- Stories/Levels: One
- Square Feet: 1,770
- Sq. Ft. Source: Public Records
- Year Built: 1965
Lot Features
- Property View: Trees/Woods
- Lot Size (Acres): 0.21
- Lot Size (Sq. Ft.): 9,230
- Lot Size: 9230
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
- Fencing (Description): Fenced, Vinyl
Financial Considerations
- Tax Amount: $4,032
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: WINTER PARK PINES UNIT 5 Z/91 LOT 31 BLKD
- Flood Zone Info: X
- APN: 92230966404310
- Property ID: 92230966404310
- Block/Lot/Section: D
Listed by Keller Williams Winter Park
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Schools
Schools serving 433 Gilbert Rd
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Brookshire Elementary School 2500 Cady Way, Winter Park, FL 32792 | PK-5 | 0.3 mi |
Glenridge Middle School 2900 Upper Park Road, Orlando, FL 32814 | 6-8 | 1.6 mi |
Winter Park High School 2100 Summerfield Road, Winter Park, FL 32792 | 9-12 | 0.7 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 433 Gilbert Rd
Date
Details
Price
Change
Source
7/27/2026
Listed
$675,000
164.71%
MLS
7/14/2014
Sold
$255,000
—
Public Record
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
Tax History for 433 Gilbert Rd
Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,032
5%
$269,858
6%
2024
$3,823
7%
$255,358
3%
2023
$3,558
6%
$247,920
6%
2021
$3,357
-2%
$233,688
-3%
2022
$3,421
2%
$240,699
4%
2021
$3,357
2%
$230,462
2%
2019
$3,282
1%
$225,281
2%
2018
$3,254
2%
$221,080
2%
2017
$3,201
1%
$216,533
2%
2016
$3,172
-2%
$212,079
1%
2015
$3,225
-2%
$210,605
29%
2014
$3,287
15%
$162,824
10%
2013
$2,864
—
$148,022
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 433 Gilbert Rd
433 Gilbert Road, Winter Park, FL 32792 (MLS# O6428430) is a Single Family property with 3 bedrooms and 2 full bathrooms. 433 Gilbert Road is currently listed for $675,000 and was received on July 27, 2026. Want to learn more about 433 Gilbert Road? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

