337 Gilbert Rd, Winter Park, FL 32792
Kitchen
Guest Bathroom
OFF MARKET

337 Gilbert Rd
Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 1,715 sqft

$596,900

Trulia Estimate
as of Aug 25, 2026
Est. Refi. Payment $4,193/mo*
Refinance Your Home

$596,900

Trulia Estimate
as of Aug 25, 2026
Est. Refi. Payment $4,193/mo*
Refinance Your Home
4 Beds
3 Baths
1,715 sqft

Home Value

Trulia Estimate
$597K
Since last month
Increased$2K (+0.4%)
Since last year
Increased$27K (+4.8%)
Since last sale
Increased$272K (+83.7%)
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 +68% in the last 10 years
MonthEstimated value
2026
August 2026$597K
July 2026$595K
June 2026$596K
May 2026$592K
April 2026$585K
March 2026$576K
February 2026$577K
January 2026$564K
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
0.07
Single-Family Home
$725,000
07/15/26
4
3
2,038
2833 PRINCE JOHN ROAD, Winter Park, FL
0.19
Single-Family Home
$400,000
02/13/26
4
2
1,605
2814 SHERIFF WAY, Winter Park, FL
0.09
Single-Family Home
$545,000
04/22/26
4
2
1,948
2756 SHERIFF WAY, Winter Park, FL
0.03
Single-Family Home
$588,000
07/08/26
3
2
1,812
2700 CADY WAY, Winter Park, FL
0.11
Single-Family Home
$610,000
07/24/26
4
2
1,876
422 S RANGER BOULEVARD, Winter Park, FL
0.26
Single-Family Home
$495,000
02/17/26
4
2
1,680
326 FITZHUGH ROAD, Winter Park, FL
0.36
Single-Family Home
$502,000
02/25/26
4
3
1,835
2748 LION HEART ROAD, Winter Park, FL
0.16
Single-Family Home
$475,000
03/16/26
3
2
1,502
2708 LION HEART ROAD, Winter Park, FL
0.17
Single-Family Home
$435,000
12/11/25
3
2
1,785
505 CORNWALL ROAD, Winter Park, FL
0.19
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
336 SAINT DUNSTAN WAY, Winter Park, FL 32792
0.03
$589,900
3
2
1,715
Off Market
313 GILBERT ROAD, Winter Park, FL 32792
0.04
-
3
2
1,642
Off Market
2756 SHERIFF WAY, Winter Park, FL 32792
0.03
$588,000
3
2
1,812
Recently Sold
350 CORNWALL RD, Winter Park, FL 32792
0.07
$725,000
4
3
2,038
Recently Sold
2712 CADY WAY, Winter Park, FL 32792
0.08
$608,100
4
3
2,197
Off Market
2758 CADY WAY, Winter Park, FL 32792
0.06
$526,700
3
2
1,560
Off Market
341 CORNWALL ROAD, Winter Park, FL 32792
0.10
$745,900
4
3
2,400
Off Market
333 CORNWALL ROAD, Winter Park, FL 32792
0.10
$549,900
4
2
1,660
For Sale
2700 CADY WAY, Winter Park, FL 32792
0.11
$610,000
4
2
1,876
Recently Sold
402 SAINT DUNSTAN WAY, Winter Park, FL 32792
0.09
$653,700
3
2
1,779
Off Market
2806 SHERIFF WAY, Winter Park, FL 32792
0.07
$519,600
3
2
1,598
Off Market
2814 SHERIFF WAY, Winter Park, FL 32792
0.09
$545,000
4
2
1,948
Recently Sold

Local Information

  • Map ViewExplore the area around 337 Gilbert Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1964
Living Area
1,715 sqft
Price/Sqft
$348
Parking
Garage

About this House

This Winter Park Pines Homes is located on a quiet tree lined street near the Cady Way Trail and the Winter Park/ Cady Way Pool on a quiet street. As you walk through the welcoming front doors of this 4 bedroom 3 bathroom home you will be greeted with a large formal living room with wood burning fireplace. The master bedroom is the perfect retreat with a view through the french doors to the large backyard and pool area. The separate dinning room is perfect for entertaining. The kitchen overlooks the family room. The other 3 bedrooms are off the family room. Two bedrooms share a jack and jill bathroom and the 4th bedroom has its own bathroom with a shower/tub that also serves as the pool bath. The 2 car garage is oversized with washer/dryer hook up. Come see this home today!!!
337 Gilbert Rd, Winter Park, FL 32792 is a 4 bedroom, 3 bathroom, 1,715 sqft single-family home built in 1964. It last sold for $325,000 on Sep 6, 2017. It is currently off market. The Trulia Estimate is $596,900, with a rent estimate of $4,032/month.

Home Details for 337 Gilbert Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Laminate
Interior Details
Additional StorageAtticTypes of Rooms: Walk In Closet, Family RoomStorage
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Heating & Cooling
Air ConditioningCooling System: Central
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: OtherPatio
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1964Year Updated: 1980
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 8276 sqft

Price and Tax history

DateEventPrice
Sep 6, 2017
Source: N/A
Sold
$325,000
Jun 17, 2017
Source: Agent Provided
Pending
$325,000
Jun 14, 2017
Source: Agent Provided
Listed For Sale
$325,000
Mar 6, 2006
Source: N/A
Sold
$320,000

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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 337 Gilbert Rd

  • What is 337 Gilbert Rd estimated to be worth?
    Trulia's estimated value for 337 Gilbert Rd in Winter Park, FL is $596,900.
  • What is the price history for 337 Gilbert Rd?
    337 Gilbert Rd in Winter Park, FL last sold for $325,000 in September 2017.
  • 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 337 Gilbert Rd have air conditioning?
    Yes, 337 Gilbert Rd in Winter Park, FL has air conditioning.
  • Does 337 Gilbert Rd have a pool?
    Yes, 337 Gilbert Rd in Winter Park, FL has a pool.

Explore by feature - Pet Friendly

146 pet-friendly rentals in Winter Park, FL

Explore by feature - Garage

65 rentals with a garage in Winter Park, FL

Explore by feature - Air Conditioning

158 rentals with air conditioning in Winter Park, FL

Explore by feature - Pool

135 rentals with a pool in Winter Park, FL

Explore by feature - Washer/dryer

158 rentals with a washer/dryer in Winter Park, FL

Explore by feature - Outdoor Space

59 rentals with an outdoor space in Winter Park, FL

Apartments for Rent

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Off Market Homes Near 337 Gilbert Rd

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