433 Gilbert Rd

Winter Park, FL 32792

$675,000
Price
3
Beds
1,770 Sq. Ft.
$381 / Sq. Ft.
1,770
Sq. Ft.
$381
per Sq. Ft.
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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...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
  1. Listed by Amy Turner • Brokerage DRE #1047416 • KELLER WILLIAMS WINTER PARK
    P: (407)-803-3885 C: (407)-803-3885 Offers@theturnergroup.com

Property Details for 433 Gilbert Road

Architectural Style
Ranch
Subdivision Name
WINTER PARK PINES
Township
22
Garage Spaces
2
View
Trees/Woods
Waterfront
No
Furnished
Unfurnished

Open Houses

Saturday, Aug 1st12:00 PM - 2:00 PM
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LISTING UPDATED: 07/28/2026 03:46 PM

Property Details for 433 Gilbert Road

StatusActive
MLS #O6428430
Days on Market2
Taxes$4,032 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1965
Lot Size0.21 AC / 9,230 SF
CountyOrange County
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Location

Listing Courtesy of KELLER WILLIAMS WINTER PARK, Amy Turner
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Building Information for 433 Gilbert Road

Stories-Year Built1965Building Size-Lot Size0.21 AC / 9,230 SF

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$3,767 per month

30 year fixed, 6.55% Interest

Principal and Interest

$3,431

Property Taxes

$336

HOA Dues

$0

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Property Information for 433 Gilbert Road

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 2754.0
  • Building Area Units: Square Feet
  • Community Features: Park, Playground, Pool, Sidewalks, Tennis Court(s)
  • Direction Faces: East
  • 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.
  • Elementary School: Brookshire Elem
  • Middle Or Junior School: Glenridge Middle
  • High School: Winter Park High
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Listing Service: Full Service
  • Road Frontage Type: Street Paved
  • Senior Community: No
  • Unit Number: No
  • Street Number: 433
  • Street Name: GILBERT
  • Street Suffix: ROAD
  • State: FL
  • City: WINTER PARK
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Driveway, Garage Door Opener, On Street, Workshop in Garage
Taxes and HOA Information
  • Association: No
  • CDD: No
  • Pet Restrictions: Buyer to verify pet restrictions with Orange County.
  • Tax Block: D
  • Tax Book Number: Z-91
  • Tax Legal Description: WINTER PARK PINES UNIT 5 Z/91 LOT 31 BLKD
  • Tax Lot: 31
  • Tax Year: 2025
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Property
Lot Information
  • Additional Parcels: No
  • Additional Water Information: Public Boat Ramp to Winter Park Chain of Lakes located less than 10 minutes drive.
  • Lot Features: Landscaped, Near Golf Course, Sidewalk, Unincorporated
  • Parcel Number: 092230966404310
  • Total Acreage: 0 to less than 1/4
  • Water Access: No
  • Water Extras: No
  • Zoning: R-1A
  • Living Area: 1770
Property and Assessments
  • Year Built Numeric: 1965
  • Amenities Additional Fees: Winter Park Pines 18 is a Public Golf Course, membership not required. Cady Way Pool also has membership availability.
  • Association Amenities: Golf Course, Pickleball Court(s), Playground, Pool, Tennis Court(s), Trail(s)
  • Flood Zone Code: X
  • Flood Zone Date: 09-25-2009
  • Flood Zone Panel: 12095C0255F
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 30
  • Public Survey Section: 09
Utilities
  • Sewer: Public Sewer
  • Utilities: BB/HS Internet Available, Electricity Connected, Sewer Connected, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block
  • Exterior Features: French Doors, Irrigation System, Private Mailbox, Rain Gutters, Sidewalk
  • Fencing: Fenced, Vinyl
  • Foundation Details: Slab
  • Levels: One
  • Patio And Porch Features: Covered, Deck, Front Porch, Porch, Rear Porch, Screened
  • Pool Features: Gunite, In Ground, Screen Enclosure
  • Pool Private: Yes
  • Pool: Private, Community
  • Pool Private: Yes
  • Roof: Shingle
  • Security Features: Security System, Security System Owned
  • Spa: No
  • Vegetation: Mature Landscaping, Trees/Landscaped
  • Waterfront Feet Total: 0
Interior Features
  • Bedrooms Total: 3
  • Bathrooms Full: 2
  • Additional Rooms: Family Room
  • Appliances: Dishwasher, Disposal, Microwave, Range, Refrigerator
  • Cooling: Central Air
  • Fireplace: No
  • 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
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 10.0
  • Water View: No
  • Window Features: Shutters
  • Bathrooms Half: 0
Rental
Rental Information
  • Pets Allowed: Cats OK, Dogs OK, Yes

Property History for 433 Gilbert Road

DateEvent & SourcePriceAppreciation
Jul 27, 2026

Listed (Active)

MFRMLS #O6428430

$675,000—
Aug 1, 2014

Sold

MFRMLS #O5206261

$255,000—
Jul 14, 2014

Sold (Public Record)

Public Record #432312308

$255,000—
DateEvent & SourcePrice
07/27/2026

Listed (Active)

MFRMLS #O6428430

$675,000
08/01/2014

Sold

MFRMLS #O5206261

$255,000
07/14/2014

Sold (Public Record)

Public Record #432312308

$255,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 433 Gilbert Road

Taxable ValueLand-Additions-Total-
Tax Record2024$3,823 ($319 / month)
Home Facts
Beds3Total Finished SqFt1,770 SqFtAbove Grade Finished SqFt1,770 SqFtStories1Lot Size9,230 SqFtStyleSingle Family ResidenceYear Built1965Year Renovated1970ZoningR-1ACountyORANGEAPN09-22-30-9664-04-310

Schools near 433 Gilbert Road

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Brookshire Elementary School
Public - PK to 5
Cornerstone Academy Charter
Charter - K to 8
Glenridge Middle School
Public - 6 to 8
Cornerstone Charter Academy High School
Charter - 9 to 12
Rating
School
Distance
Brookshire Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Glenridge Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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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 27, 2026 by KELLER WILLIAMS WINTER PARK, it's currently listed at $675,000. It has been on the market for a total of 2 days and was last sold on August 1, 2014. This listing's school district is Orange County Public Schools. Nearby schools include Brookshire Elementary School, Cornerstone Academy Charter and Glenridge Middle School. 433 Gilbert Road is a 3-bed, 2-bath, 1,770 sqft single family home built in 1965.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of KELLER WILLIAMS WINTER PARK, Amy Turner

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 07/28/2026 03:46 PM