433 GILBERT ROAD, Winter Park, FL 32792
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Property image
FOR SALE
OPEN SAT, 12-2PM
3D VIEW

$669,900

Original price: $675,000
  • 3 Beds
  • 2 Baths
  • 1,770 sqft

433 GILBERT ROAD, Winter Park, FL 32792

Est. Mortgage $4,808/mo*
Get Pre-Qualified
We estimate this home will sell faster than 95% nearby.

Home Highlights

Single-Family Home
Built in 1965
$378/sqft
2 Car Garage

Local Information

  • Map ViewExplore the area around 433 GILBERT ROAD.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

**DONT MISS OUT!** Welcome home 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 PANEL - 2021
Last check for updates: about 5 hours ago
Listing Provided by: Amy Turner, (407) 803-3885
KELLER WILLIAMS WINTER PARK, (407) 545-6430
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6428430
Also Listed on Stellar MLS.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
We estimate this home will sell faster than 95% nearby.

Open House

Saturday, September 19
12:00 PM to 2:00 PM

Home Details for 433 GILBERT ROAD

Interior Features

Interior Details
Number of Rooms: 10Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Primary Bathroom, Bathroom 2, Balcony Porch Lanai, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1770 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Electricity Connected, Sewer Connected, Water ConnectedAppliances: Dishwasher, Disposal, Microwave, Range, RefrigeratorDishwasherDisposalLaundry: In GarageMicrowaveRefrigerator
Heating & Cooling
Heating: ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Electric
Fireplace & Spa
No FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Door: French DoorsFlooring: Ceramic Tile, Laminate, Terrazzo
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Ceramic Tile, Laminate, Terrazzo
View
Has a ViewView: Trees/Woods
Security
Security: Security System, Security System Owned

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Deck, Front Porch, Porch, Rear Porch, ScreenedFencing: Fenced, VinylVegetation: Mature Landscaping, Trees/LandscapedExterior: Irrigation System, Private Mailbox, Rain Gutters, SidewalkFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Garage Door Opener,On Street,Workshop in Garage
Pool
Pool: Gunite, In Ground, Screen EnclosurePool
Frontage
Road Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 38Days on Market: 52

Property Information

Year Built
Year Built: 1965
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: BlockNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 092230966404310

Price & Status

Price
List Price: $669,900Price Per Sqft: $378
Status Change & Dates
Possession Timing: Close Of Escrow

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: WINTER PARKCommunity: WINTER PARK PINES
School Information
Elementary School: Brookshire ElemJr High / Middle School: Glenridge MiddleHigh School: Winter Park High

Agent Information

Listing Agent
Listing ID: O6428430

Building

Building Area
Building Area: 2754 Square Feet

Community

Community Features: Park, Playground, Pool, Sidewalks, Tennis Court(s)Not Senior Community
Other
Playground

HOA

Association for this Listing: Orlando RegionalNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 9230 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6428430Back On Market Date: Thu Sep 17 2026Showing Considerations: See RemarksShowing Requirements: Appointment Only, See Remarks, ShowingTimeUniversal Property Id: US-12095-N-092230966404310-R-N

Additional Information

HOA Amenities: Golf Course,Pickleball Court(s),Playground,Pool,Tennis Court(s),Trail(s)

Around this home

What Locals Say about Winter Park

At least 596 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say there are sidewalks

  • 84 % Say car is needed

  • 80 % Say parking is easy

  • 74 % Say there's holiday spirit

  • 70 % Say yards are well-kept

  • 68 % Say it's quiet

  • 67 % Say streets are well-lit

  • 65 % Say people would walk alone at night

  • 62 % Say it's walkable to restaurants

  • 62 % Say kids play outside

  • 57 % Say it's walkable to grocery stores

  • 52 % Say they plan to stay for at least 5 years

  • 51 % Say neighbors are friendly

  • 39 % Say there's wildlife

  • 29 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "We are retired, so we do not need public transportation. I see many buses around the area, and there is a light rail train."
    0
    Flag
  • Giannina Munoz
    "All of them they are so family friendly especially around Halloween they have a haunted trail so cute "
    0
    Flag
  • Jasmine Miller
    "I see dogs everywhere. People often do meet and greets between dogs. There are always bowls of water as well as jars of dog treats often seen. "
    0
    Flag
  • Ed Agudelo
    "It is a nice neighborhood with lots to do locally and easy to walk to parks, restaurants and shops. "
    0
    Flag
  • Trulia User
    "Some people are great some aren’t great but close to shops and grocery stores sports cooking cleaning"
    0
    Flag
  • Heidiromy
    "The mature landscape, is safe and family friendly, pet friendly, quiet, beautiful, community oriented. "
    0
    Flag
  • Timothyjohnson
    "Winter park art festivals and Farmers Market are always a good time. There lots of great restaurants. "
    0
    Flag
  • andrea brewer
    "It’s a quiet and beautiful area that’s perfect for families and single professionals alike. Lots of great small businesses that thrive regardless of the time of year."
    0
    Flag
  • Paul Swain
    "Holidays are dull here. People keep to themselves. Everything is close by. Things are in good condition. Driving down town is a little hectic but worth it "
    0
    Flag
  • Gabrielcoello094
    "It’s a great place to live and raise your kids, I love it here, lot of things to do, good public schools around and safe."
    2
    Flag
  • Timothyjohnson
    "We used to have an annual parade for Goldenrod, but has not occurred in many years. There is a lack a “center” specifically for Goldenrod. "
    0
    Flag
  • Trulia User
    "I would say the only community events in this area are hosted by the elementary schools and those are okay but not enough "
    0
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  • Trulia User
    "It’s always traffic on Semoran. This area is just BUSY!! Early morning, all times of the day and late nights. "
    2
    Flag
  • Trulia User
    "You would need a car to get to most things, but there are a lot of little restaurants nearby if you like. "
    0
    Flag
  • Trulia User
    "everything is close buy like supermarkets post office and fat food places. it's a safe neighborhood. I have had no incidents since I moved here. it has that family feel to it as the people are friendly and look out for each other"
    3
    Flag
  • David S.
    "Very pet friendly. Lots of fellow dog owners in the area. Just make sure to clean up after your fur buddy"
    0
    Flag
  • Monique J.
    "Close to everything, 15 minutes to everything from downtown to schools. This neighborhood has a lot of good and is close to food and shopping. The neighborhood is kept clean with very little trash."
    8
    Flag
  • A R. S.
    "Rollins College and UCF colleges with events like sports close by. AmWay center and Campers World Stadium only 6 miles away for NBA , Football (Citrus Bowl) and Major music concerts. Park Ave beautiful shops, beautiful landscapes and beautiful people - - young and some what older."
    4
    Flag
  • Holly A. C.
    "No public transportation thats convenient.i drive a car and plenty Of parking lots and street parking "
    5
    Flag
  • Ross H.
    "I love winter Park have lived here for about 7 years and hope to live here longer. the people are nice and the area is clean "
    0
    Flag
  • Winterparkhomes
    "I have lived in Winter Park since 1988 and I Love it! It’s close proximity to groceries, hospital, restaurants and shopping is awesome !"
    2
    Flag
  • Messagedrop
    "Great place to live if you like to walk or ride bicycles. Close to shopping, entertainment, restaurants, college sports venues."
    0
    Flag
  • Francois B.
    "Most dog owners don’t pick up after them selfs and even when the park provides bags to clean the dogs needs"
    0
    Flag
  • Donna G.
    "Very trendy area! Family oriented! Grocery stores and great schools! A nice beautiful landscaped place to work and raise your family!"
    0
    Flag
  • Daylen C.
    "It’s historic and it’s established. Lots of charm and mature trees. You rarely see trash and the roads are lost. It’s very easy to grab a great bite to eat everywhere. My favorite place is the mead botanical gardens. A little escape in the middle of the city. "
    0
    Flag
  • Luna M.
    "It’s a safe and friendly neighborhood. Not really any crime, lots of people outside walking their dogs and parents feel safe enough to let their kids ride around on their bikes to the store or the parks or what have you. Great place to live all around. Highly recommend."
    6
    Flag
  • David C.
    "I just moved here last week and it seems like a nice area. There is a lot of traffic and it’s been warmer then up north."
    3
    Flag
  • George P.
    "right off a preserve and Lake Howell so lots of wildlife like turkeys, bald Eagles, hawks, herons, egrets, ibis and sandhill cranes always around. close to shopping restaurants and the gym"
    0
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  • Daniel V.
    "It’s a great and safe area, you’re in walking distances from lakes, parks, etc. you have a great shopping center and restaurants. "
    0
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  • Ross H.
    "area is amazing close to everything I've live around winter Park for about 7 years and can't find anything really wrong with it"
    0
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  • Heidi W.
    "Winter Park is a safe and happy place to raise a family. I have lived here since Kindergarten and I’m 33 now, raising my own family. "
    3
    Flag
  • Luna M.
    "I love it here. Can't go wrong living here. It's friendly, safe, quiet. I can't say enough good things about this neighborhood."
    2
    Flag
  • Nicole B.
    "Beautiful and very safe best place to raise a family. Lots of people go outdoors and exercise. Good for walking dogs and going to parks"
    2
    Flag
  • Elizabeth C.
    "Many restaurants are pet friendly. Park Ave is a great place to spend time at. Many public events are held there. On Saturday’s there’s the farmers market. "
    1
    Flag
  • Sarah S.
    "We have Cady way trail which is great for dogs and plenty of sidewalks and dog waste bag reciprocals. "
    1
    Flag
  • Blanca V.
    "I love this area. we moved here years ago. My children grew up here, went schools here and now they're in college. I wouldn't have it any other. Winter park has been good to us."
    3
    Flag
  • Joenaijah.sam
    "My neighbor has various restaurants to eat at all really good food. I truly enjoy cuban cafes and Japanese dishes. "
    0
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  • Jonvaden
    "I see people walking their dogs all the time on the sidewalks under streetlights so I think they are happy. I myself am not a pet owner."
    0
    Flag
  • Thompson C.
    "Perfect area to live. Close proximity to everything. Golfing, jogging, walks and casual stroll around the neighborhood is encouraged. Close access to major highways like I-4, 408 414. Plenty of restaurants to choose from Mexican, Thai, Indian, Italian etc. "
    1
    Flag
  • Blanca V.
    "There are many families living in this neighborhood and we have great parks and schools in the are. I love this place I've been living here for 7 years with my family and been happy to be in that one of the most beautiful cities in Florida. . Our schools are a plus schools in RL parks are amazingly beautiful the lakes are nice to be and spend an evening with your family or your couple "
    0
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Market trends in Winter Park

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$455K
$4.03KMoM
Sale-to-List Price
98.1%
0.1%MoM
Price per sq ft
$281
$6MoM
Available listings
382
13MoM

Home Value

Trulia Estimate
$656K
Since last month
Increased$3K (+0.5%)
Since last year
Increased$123K (+23%)
Since last sale
Increased$401K (+157.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +128% in the last 10 years
MonthEstimated value
2026
September 2026$656K
August 2026$653K
July 2026$673K
June 2026$557K
May 2026$555K
April 2026$546K
March 2026$541K
February 2026$539K
January 2026$530K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
528 SAINT DUNSTAN WAY, Winter Park, FL
0.07
Single-Family Home
$536,000
08/19/26
3
2
1,656
2817 FITZOOTH DRIVE, Winter Park, FL
0.11
Single-Family Home
$600,000
01/23/26
3
2
1,619
513 CORNWALL ROAD, Winter Park, FL
0.12
Single-Family Home
$629,000
04/03/26
3
2
1,735
2756 SHERIFF WAY, Winter Park, FL
0.16
Single-Family Home
$588,000
07/08/26
3
2
1,812
2485 MIDDLETON AVENUE, Winter Park, FL
0.25
Single-Family Home
$450,000
10/27/25
3
2
1,515
2774 BANCHORY ROAD, Winter Park, FL
0.15
Single-Family Home
$645,000
07/21/26
3
2
1,560
517 ROUGHBEARD ROAD, Winter Park, FL
0.22
Single-Family Home
$576,000
07/17/26
3
2
1,873
2708 LION HEART ROAD, Winter Park, FL
0.33
Single-Family Home
$435,000
12/11/25
3
2
1,785
2552 BROOKSHIRE AVENUE, Winter Park, FL
0.20
Single-Family Home
$530,000
08/31/26
3
1.5
1,314
505 CORNWALL ROAD, Winter Park, FL
0.12
Single-Family Home
$670,000
07/22/26
4
2
1,813

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
418 GILBERT ROAD, Winter Park, FL 32792
0.05
$691,300
3
3
1,680
Off Market
417 GILBERT ROAD, Winter Park, FL 32792
0.03
$670,100
4
3
2,231
Off Market
423 LONDON ROAD, Winter Park, FL 32792
0.06
$815,800
4
3
3,072
Off Market
402 SAINT DUNSTAN WAY, Winter Park, FL 32792
0.08
$649,100
3
2
1,779
Off Market
2758 CADY WAY, Winter Park, FL 32792
0.11
$530,200
3
2
1,560
Off Market
528 SAINT DUNSTAN WAY, Winter Park, FL 32792
0.07
$536,000
3
2
1,656
Recently Sold
2817 FITZOOTH DRIVE, Winter Park, FL 32792
0.11
$600,000
3
2
1,619
Recently Sold
541 LONDON ROAD, Winter Park, FL 32792
0.11
$462,600
3
2
1,899
Off Market
2765 BANCHORY ROAD, Winter Park, FL 32792
0.12
$615,300
3
2
1,551
Off Market
2840 CADY WAY, Winter Park, FL 32792
0.17
$501,900
3
2
1,407
Off Market
2712 CADY WAY, Winter Park, FL 32792
0.14
$606,200
4
3
2,197
Off Market

Price and Tax history

DateEventPrice
Aug 21, 2026
Source: Stellar MLS #O6428430
PriceChange
$669,900
Price decreased by 1%
Jul 27, 2026
Source: Stellar MLS #O6428430
Listed For Sale
$675,000
Aug 12, 2014
Source: N/A
Sold
$255,000
May 15, 2014
Source: Agent Provided
PriceChange
$279,000
Price decreased by 3%
Mar 27, 2014
Source: Agent Provided
PriceChange
$289,000
Price decreased by 2%

LGBTQ Local Legal Protections

Amy Turner, KELLER WILLIAMS WINTER PARK, (407) 545-6430
Agent Phone: (407) 803-3885

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Frequently asked questions about 433 GILBERT ROAD

  • What is the estimated monthly payment for 433 GILBERT ROAD?
    Based on a $669,900 list price with 20% down at today's rates, the estimated monthly payment for 433 GILBERT ROAD in Winter Park, FL is approximately $4,889 (about $3,625 principal & interest, $1,189 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 433 GILBERT ROAD compare to homes in Winter Park?
    433 GILBERT ROAD in Winter Park, FL is listed at $669,900, about 47% above the $455K median sale price in Winter Park.
  • What do residents say about Winter Park?
    Residents describe Winter Park, FL as dog-friendly, pedestrian-friendly, and easy to park in. See homes for sale in Winter Park, FL.
  • What are the closest schools to 433 GILBERT ROAD?
    The closest schools to 433 GILBERT ROAD in Winter Park, FL are Brookshire Elementary School (Pre-K, rated 4/10), Glenridge Middle School (rated 7/10), Winter Park High School (rated 7/10).
  • Does 433 GILBERT ROAD have air conditioning?
    Yes, 433 GILBERT ROAD in Winter Park, FL has air conditioning.
  • Does 433 GILBERT ROAD have a pool?
    Yes, 433 GILBERT ROAD in Winter Park, FL has a pool.
433 GILBERT ROAD, Winter Park, FL 32792 is a 3 bedroom, 2 bathroom, 1,770 sqft single-family home built in 1965. This property is currently available for sale and was listed by Stellar MLS on Jul 27, 2026. The MLS # for this home is MLS# O6428430.