433 GILBERT ROAD, WINTER PARK, FL 32792

$675,0003 Beds2 Baths1,770 Sq. Ft.$381 / sq. ft.

WINTER PARK, FL 32792 · MLS# O6428430 · Active · WINTER PARK PINES

Status
Active
Type
Single Family Residence
Year Built
1965
Days on Market
9
Lot Size
9,230 sqft
MLS #
O6428430
County
Orange

Description of 433 GILBERT ROAD, WINTER PARK, FL 32792

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

Property Details for 433 GILBERT ROAD, WINTER PARK, FL 32792

Bathrooms Full
2
Bathrooms Half
0
Interior Features
Built-in Features, Ceiling Fan(s), Eating Space In Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s)
Appliances
Dishwasher, Disposal, Microwave, Range, Refrigerator
Flooring
Ceramic Tile, Laminate, Terrazzo
Heating
Electric
Cooling
Central Air
Furnished
Unfurnished
Architectural Style
Ranch
Garage Spaces
2
Attached Garage
Yes
Parking Features
Driveway, Garage Door Opener, On Street, Workshop in Garage
Pool Features
Gunite, In Ground, Screen Enclosure
Pool Private
Yes
Direction Faces
East

Building Information for 433 GILBERT ROAD, WINTER PARK, FL 32792

Building Area Total
2754
Building Area Units
Square Feet
Association
No
Association Amenities
Golf Course, Pickleball Court(s), Playground, Pool, Tennis Court(s), Trail(s)
Pets Allowed
Cats OK, Dogs OK, Yes
Security Features
Security System, Security System Owned

Property Information for 433 GILBERT ROAD, WINTER PARK, FL 32792

Lot Features
Landscaped, Near Golf Course, Sidewalk, Unincorporated
Lot Size Square Feet
9,230
Waterfront
No
View
Trees/Woods
Construction Materials
Block
Roof
Shingle
Exterior Features
French Doors, Irrigation System, Private Mailbox, Rain Gutters, Sidewalk
Sewer
Public Sewer
Water Source
Public
New Construction
No

Public Records for 433 GILBERT ROAD, WINTER PARK, FL 32792

Parcel Number
092230966404310
Tax Annual Amount
$4,032
Tax Year
2025
Tax Legal Description
WINTER PARK PINES UNIT 5 Z/91 LOT 31 BLKD
Zoning
R-1A
County Or Parish
Orange

Schools Near 433 GILBERT ROAD, WINTER PARK, FL 32792

Elementary School
Brookshire Elem
Middle School
Glenridge Middle
High School
Winter Park High

School assignments are provided by the listing and should be independently verified.

Payment Calculator

Estimated Payment
$4,087/mo
Principal & Interest
$3,413
Property Taxes
$336
Home Insurance
$338

Estimate only — actual rates, taxes and insurance vary. Not a loan offer or financial advice. Financing through Matthew Gromadzki, NMLS #2560919 · Innovative Mortgage Services, Inc., NMLS #250769.

Location

433 GILBERT ROAD, WINTER PARK, FL 32792 · See all Winter Park homes for sale

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More information about 433 GILBERT ROAD, WINTER PARK, FL 32792

433 GILBERT ROAD is a single family home for sale in WINTER PARK, FL 32792. This property was listed for sale on July 25, 2026 by KELLER WILLIAMS WINTER PARK, it's currently listed at $675,000. This listing's school district is Orange Public Schools. Nearby schools include Brookshire Elem, Glenridge Middle and Winter Park High. 433 GILBERT ROAD is a 3-bed, 2-bath, 1,770 sqft single family home built in 1965.