Gabriella Massaro

Gabriella Massaro Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

$675,000.00
433 GILBERT ROAD, WINTER PARK, FL - 32792
3 beds
2.0 baths
1,770 sqft
$675,000.00
433 GILBERT ROAD, WINTER PARK, FL - 32792
Gabriella Massaro
$675,000.00
3 beds
2.0 baths
1,770 sqft
433 GILBERT ROAD, WINTER PARK, FL - 32792
For Sale
Photo 1
  • Built in 1965
  • 2 garage spaces
  • $381.36/sqft
  • Lot size: 9,230 sqft
  • 1 days on market

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, beam, resurfacing, and 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

  • 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.
  • County: Orange
  • Geo subdivision: WINTER PARK PINES

Nearby Schools

Brookshire Elem

Glenridge Middle

Winter Park High

Features

Financial

Let's get in touch!

Gabriella Massaro

Gabriella Massaro

Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

See also

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37 E VANDERBILT STREET, ORLANDO, FL - 32804
$699,900.00
3 bds
3.0 ba
2,000 sqft
37 E VANDERBILT STREET, ORLANDO, FL - 32804
For Sale
2692 CAVANAUGH DRIVE, ORLANDO, FL - 32817
$650,000.00
4 bds
3.5 ba
2,560 sqft
2692 CAVANAUGH DRIVE, ORLANDO, FL - 32817
For Sale
741 BROOKSIDE ROAD, MAITLAND, FL - 32751
$615,000.00
4 bds
2.0 ba
1,975 sqft
741 BROOKSIDE ROAD, MAITLAND, FL - 32751
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6428430
Listing updated: July 28, 2026 at 10:47AM
Listing provided by: Amy Turner, KELLER WILLIAMS WINTER PARK
Last checked 46 minutes ago
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