417 GILBERT ROAD, Winter Park, FL 32792
OFF MARKET

$660,600

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,231 sqft

417 GILBERT ROAD, Winter Park, FL 32792

Est. Refi. Payment $4,623/mo*
Refinance Your Home
Currently Off Market - Sold Jan 21, 2025 for $650,000

Home Value

Trulia Estimate
$661K
Since last month
Increased$19K (+3%)
Since last year
Increased$20K (+3.1%)
Since last sale
Increased$13K (+2%)
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 +79% in the last 10 years
MonthEstimated value
2026
August 2026$663K
August 2026$661K
July 2026$644K
June 2026$641K
May 2026$639K
April 2026$632K
March 2026$625K
February 2026$630K
January 2026$632K
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
350 CORNWALL RD, Winter Park, FL
0.14
Single-Family Home
$725,000
07/15/26
4
3
2,038
2700 CADY WAY, Winter Park, FL
0.14
Single-Family Home
$610,000
07/24/26
4
2
1,876
505 CORNWALL ROAD, Winter Park, FL
0.12
Single-Family Home
$670,000
07/22/26
4
2
1,813
639 FRIAR ROAD, Winter Park, FL
0.27
Single-Family Home
$795,000
05/08/26
4
3
1,950
2814 SHERIFF WAY, Winter Park, FL
0.15
Single-Family Home
$545,000
04/22/26
4
2
1,948
2756 SHERIFF WAY, Winter Park, FL
0.13
Single-Family Home
$588,000
07/08/26
3
2
1,812
513 CORNWALL ROAD, Winter Park, FL
0.13
Single-Family Home
$629,000
04/03/26
3
2
1,735
528 SAINT DUNSTAN WAY, Winter Park, FL
0.09
Single-Family Home
$536,000
08/19/26
3
2
1,656
630 SAINT DUNSTAN WAY, Winter Park, FL
0.23
Single-Family Home
$710,000
04/01/26
5
2
2,240
2817 FITZOOTH DRIVE, Winter Park, FL
0.13
Single-Family Home
$600,000
01/23/26
3
2
1,619

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
0.03
$691,300
3
3
1,680
Off Market
423 LONDON ROAD, Winter Park, FL 32792
0.06
$804,400
4
3
3,072
Off Market
410 SAINT DUNSTAN WAY, Winter Park, FL 32792
0.04
$500,000
3
2
1,512
For Sale
402 SAINT DUNSTAN WAY, Winter Park, FL 32792
0.05
$651,500
3
2
1,779
Off Market
2758 CADY WAY, Winter Park, FL 32792
0.08
$524,600
3
2
1,560
Off Market
528 SAINT DUNSTAN WAY, Winter Park, FL 32792
0.09
$536,000
3
2
1,656
Recently Sold
2817 FITZOOTH DRIVE, Winter Park, FL 32792
0.13
$600,000
3
2
1,619
Recently Sold
541 LONDON ROAD, Winter Park, FL 32792
0.13
$464,200
3
2
1,899
Off Market
2765 BANCHORY ROAD, Winter Park, FL 32792
0.14
$610,100
3
2
1,551
Off Market
2840 CADY WAY, Winter Park, FL 32792
0.15
$496,400
3
2
1,407
Off Market
2712 CADY WAY, Winter Park, FL 32792
0.12
$606,200
4
3
2,197
Off Market

Local Information

  • Map ViewExplore the area around 417 GILBERT ROAD.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1964
2,231 sqft
$296/sqft
2 Car Garage

About this House

Welcome to this spacious and charming home located in the sought-after Winter Park Pines neighborhood! As you approach the property, a covered porch invites you to relax before stepping inside. The entryway greets you with a functional hallway featuring hanging hooks, perfect for backpacks and coats. To the right, you'll find a cozy family room, complete with a wood-burning fireplace and built-in shelving. The open flow leads to the dining room, adjacent to a massive kitchen boasting granite countertops, two dishwashers, a double oven, and even a built-in office nook—perfect for today’s modern lifestyle. The split floor plan ensures privacy, with the primary retreat nestled off the family room. This retreat features a walk-in closet, and an en suite bath with a walk-in shower. On the opposite side of the house, three additional bedrooms await. Two of these bedrooms share a Jack-and-Jill bathroom, beautifully updated with quartz countertops, dual sinks, and a walk-in shower. The third bedroom is conveniently located next to a full bathroom with granite countertops and a shower-tub combo. One of the home’s highlights is the large Florida room, providing additional living space with endless possibilities. Outside, the backyard is a true oasis, featuring a large pool with a child safety fence, lush grass, and a fully fenced yard—ideal for both relaxation and play. This home is perfectly situated near Winter Park Pines Golf Course, highly rated schools, shopping, and dining options, offering the best of Winter Park living.
417 GILBERT ROAD, Winter Park, FL 32792 is a 4 bedroom, 3 bathroom, 2,231 sqft single-family home built in 1964. It last sold for $650,000 on Jan 21, 2025 (4% below the $675,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $660,600, with a rent estimate of $4,112/month.
Last check for updates: about 22 hours ago
Listed by Jenny Lake, (407) 607-4878
FANNIE HILLMAN & ASSOCIATES, (407) 644-1234
Bought with: Jenny Lake, (407) 607-4878, FANNIE HILLMAN & ASSOCIATES, (407) 644-1234
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6242880
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

Home Details for 417 GILBERT ROAD

Interior Features

Interior Details
Number of Rooms: 8Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Florida Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2231 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Phone Available, Public, Sewer Connected, Sprinkler Recycled, Street Lights, Water ConnectedAppliances: Oven, Cooktop, Dishwasher, Electric Water Heater, Freezer, Ice Maker, Kitchen Reverse Osmosis System, Microwave, RefrigeratorDishwasherLaundry: Electric Dryer Hookup,In Garage,Washer HookupMicrowaveRefrigerator
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Living Room, Wood BurningHas a FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Blinds, Drapes, Rods, Window TreatmentsFlooring: Terrazzo, Tile
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Terrazzo, Tile
View
No View
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Deck, Front Porch, PatioFencing: VinylVegetation: Mature Landscaping, Trees/LandscapedExterior: Irrigation System, 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 Faces Rear,On Street
Pool
Pool: Child Safety Fence, Gunite, In GroundPool
Frontage
Responsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Asphalt, PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 92

Property Information

Year Built
Year Built: 1964
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Bungalow
Building
Construction Materials: Block, BrickNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 302209966404290

Price & Status

Price
List Price: $675,000
Status Change & Dates
Off Market Date: Fri Dec 20 2024

Active Status

MLS Status: Sold

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

Building

Building Area
Building Area: 2873 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 9196 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6242880Showing AttendedShowing Requirements: Appointment Only, Call Before Showing, Call Listing Agent, Listing Agent Must Accompany, See Remarks, ShowingTimeUniversal Property Id: US-12095-N-302209966404290-R-N

Price and Tax history

DateEventPrice
Jan 21, 2025
Source: Stellar MLS #O6242880
Sold
$650,000
Dec 21, 2024
Source: Stellar MLS #O6242880
Pending
$675,000
Nov 20, 2024
Source: Stellar MLS #O6242880
PriceChange
$675,000
Price decreased by 3%
Nov 13, 2024
Source: Stellar MLS #O6242880
PriceChange
$694,000
Price decreased by 1%
Oct 14, 2024
Source: Stellar MLS #O6242880
PriceChange
$699,000
Price decreased by 4%

Market trends in Winter Park

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$451K
$833MoM
Sale-to-List Price
98.0%
0.3%MoM
Price per sq ft
$287
$0MoM
Available listings
368
12MoM

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
    Flag
  • 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
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  • 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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LGBTQ Local Legal Protections

Frequently asked questions about 417 GILBERT ROAD

  • What is 417 GILBERT ROAD estimated to be worth?
    Trulia's estimated value for 417 GILBERT ROAD in Winter Park, FL is $660,600.
  • What is the price history for 417 GILBERT ROAD?
    417 GILBERT ROAD in Winter Park, FL last sold for $650,000 in January 2025.
  • Is Winter Park a buyer's or seller's market?
    Winter Park is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Park?
    The median sale price in Winter Park is $451K. That is down $833 from the prior month.
  • Does 417 GILBERT ROAD have air conditioning?
    Yes, 417 GILBERT ROAD in Winter Park, FL has air conditioning.
  • Does 417 GILBERT ROAD have a pool?
    Yes, 417 GILBERT ROAD in Winter Park, FL has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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