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
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
Property Details
Price:
$669,900
MLS #:
O6428430
Status:
Active
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINTER PARK PINES
Neighborhood:
32792winterparkaloma
Listed Date:
Jul 27, 2026
Finished Sq Ft:
1,770
Total Sq Ft:
2,754
Lot Size:
9,230 sqft / 0.21 acres (approx)
Year Built:
1965
See this Listing
Schools
Elementary School:
Brookshire Elem
Middle School:
Glenridge Middle
High School:
Winter Park High
Interior
Appliances
Dishwasher, Disposal, Microwave, Range, Refrigerator
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Ceramic Tile, Laminate, Terrazzo
Heating
Electric
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)
Laundry Features
In Garage
Levels
One
Exterior
Architectural Style
Ranch
Association Amenities
Golf Course, Pickleball Court(s), Playground, Pool, Tennis Court(s), Trail(s)
Attached Garage YN
1
Community Features
Park, Playground, Pool, Sidewalks, Tennis Court(s)
Construction Materials
Block
Covered Spaces
2
Direction Faces
East
Exterior Features
French Doors, Irrigation System, Private Mailbox, Rain Gutters, Sidewalk
Fencing
Fenced, Vinyl
Garage Spaces
2
Lot Features
Landscaped, Near Golf Course, Sidewalk, Unincorporated
Open Parking YN
1
Parking Features
Driveway, Garage Door Opener, On Street, Workshop in Garage
Patio And Porch Features
Covered, Deck, Front Porch, Porch, Rear Porch, Screened
Roof
Shingle
Security Features
Security System, Security System Owned
View
Trees/Woods
Window Features
Shutters
Financial
Tax Year
2025
Taxes
$4,032
Map
Community
- Address433 GILBERT ROAD WINTER PARK FL
- SubdivisionWINTER PARK PINES
- CityWINTER PARK
- CountyOrange
- Zip Code32792
Subdivisions in WINTER PARK
Market Summary
Current real estate data for Single Family in WINTER PARK as of Aug 29, 2026
302
Single Family Listed
85
Avg DOM
468
Avg $ / SqFt
$1,281,345
Avg List Price
Property Summary
- Located in the WINTER PARK PINES subdivision, 433 GILBERT ROAD WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32792. It is listed for $669,900 and features 3 beds, 2 baths, and has approximately 1,770 square feet of living space, and was originally constructed in 1965. The current price per square foot is $378. The average price per square foot for Single Family listings in WINTER PARK is $468. The average listing price for Single Family in WINTER PARK is $1,281,345. To schedule a showing of MLS#o6428430 at 433 GILBERT ROAD in WINTER PARK, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of KELLER WILLIAMS WINTER PARK. 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. 433 GILBERT ROAD
WINTER PARK, FL