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About this home
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, resurfaced, 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
Winter Park Pines, located between Semoran Boulevard (SR 436) and Howell Branch Road, is a residential and suburban Winter Park neighborhood with mid-century ranch streetscapes and a canopy of mature oaks. The neighborhood’s character concentrates around the Howell Branch Road and Semoran Boulevard crossroads, where everyday errands cluster beside steady traffic and pocket plazas. Single-story homes, screened lanais, and generous lots set a low-slung architectural rhythm, with sidewalks and cul-de-sacs shaping a calm, lived-in feel. Cady Way Trail adds a linear green corridor for walking and cycling. Ward Park and the Winter Park Library bring courts, lawns, and civic programming into the weekly routine. Nearby, Winter Park Village supplies a modern retail-and-dining hub without shifting the neighborhood’s quiet tone.
Provided by Walk Score and Local Logic
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Dining
Interior features
Built-in features
Ceiling fans
Eat-in kitchen
Kitchen and family room combo
Living room and dining room combo
Stone counters
Thermostat
Walk-in closets
Shutters on windows
Bedrooms
3 bedrooms
Bathrooms
2 full bathrooms
Kitchen
Dishwasher
Disposal
Microwave
Range
Refrigerator
Laundry & utility
Laundry area in garage
Flooring
Ceramic tile
Laminate
Terrazzo
Heating & cooling
Electric heating
Central air conditioning
Exterior features
Covered patio/porch
Deck
Front porch
Rear porch
Screened porch
French doors
Private mailbox
Rain gutters
Sidewalks
Vinyl fencing
Mature landscaping and trees
Near golf course
Paved lot
Landscaped yard
Public boat ramp to Winter Park Chain of Lakes within a 10-minute drive
Home design
Single family residence
One level
Faces east
Residential zoning R-1A
Homestead property
Parking
Driveway
On-street parking
2-car garage with garage door opener and workshop space
Has attached garage
Security
Owned security system
Construction
Block construction
Shingle roof
Slab foundation
Built area and lot size recorded in public records
Utilities
Public water
Public sewer
Electricity connected
High-speed/BB internet available
Sewer connected
Water connected
Irrigation equipment installed
HOA & community
Community amenities include park, playground, pool, tennis courts, pickleball courts and trails
Pets allowed (cats and dogs)
Financial info
Lease restrictions apply
Other
No secondary association
Property listed unfurnished
Electricity and solar
View estimated energy costs and solar savings for this home
Lovingly maintained 3 bedroom, 2 bath pool home in sought after Winter Park Pines! Home is being sold "AS IS" but there are no known issues! The roof was replaced in 2006! The spacious eat-in kitchen was totally renovated in the past 5 years with new cabinetry & all stainless appliances. The ceramic tile floor extends to the light and bright 16x15 family room with a brick accent wall. Ceiling fans in kitchen eating area and family room! Sliding doors open to a 30x9 screened porch with a large grill w/ rotisserie & separate screen enclosed sparkling 35' free form pool & deck. Three citrus trees add to the Florida flavor. The large bedrooms are perfectly furnished with ample sized closets, storage & ceiling fans! Newer washer, dryer and laundry tub remain in the 2 car garage! The "tagged" T. V. and oil painting do not convey! Seller will dispose of furniture if buyer doesn't want it!!
Public Records
Jun 1, 1993
Sold
$122,000
$69/sq ft
Public Records
Jul 1, 1978
Sold
$59,900
$34/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$4,032 (+5.5%)
2024
$3,823 (+7.4%)
2023
$3,558 (+4.0%)
2022
$3,421 (+1.9%)
2021
$3,357 (+5.1%)
2020
$3,194 (−2.7%)
2019
$3,282 (+0.9%)
2018
$3,254 (+1.7%)
2017
$3,201 (+0.9%)
2016
$3,172 (−1.6%)
2015
$3,225 (−1.9%)
$90,000 + $120,605
$210,605
2014
$3,286 (+14.7%)
2013
$2,864 (−0.4%)
2012
$2,875
Public record
Public record
Zoning
Beds
3
Baths
2
Stories
1
Lot width
—
Lot depth
—
Lot size
9,230 Sq. Ft.
Year renovated
1970
Finished Sq. Ft.
1,770
Unfinished Sq. Ft.
—
Total Sq. Ft.
1,770
Year built
1965
Style
Single Family Residential
County
Orange County
APN
302209966404310
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 17, 2026.
R-1A
Single-Family Dwelling Districts
The areas included within R-1-A single-family dwelling districts are intended to be single-family residential areas with large lots and low population densities. Certain structures and uses required to serve educational, religious, utilities and noncommercial recreational needs of such areas are permitted within the districts as special exceptions.
Permitted uses
Include but are not limited to:
Livestock production
Housing-Single unit
Fire house
Police station
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
9/10 Heat Factor
7 days above 107° expected this year, 23 days in 30 years
9/10 Wind Factor
99% chance of strong winds in next 30 years
2/10 Air Factor
0 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Winter Park, FL • 32792
Average low and high temperatures (°F)
68
48
74
54
80
60
84
64
90
72
91
75
92
76
91
76
89
75
83
68
78
60
74
55
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
97/ 100
Exceptional sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
10.9 hrs
8 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 433 Gilbert Rd
We cannot show automated home-value estimates for this home.
Nearby homes have recently sold between $588,000 and $670,000.
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $588K to $670K.