345 Gilbert Rd, Winter Park, FL 32792
Property image
Property image
OFF MARKET

$528,600

Trulia Estimate
as of Aug 30, 2026
  • 3 Beds
  • 2 Baths
  • 1,692 sqft
  • 3 Beds
  • 2 Baths
  • 1,692 sqft

345 Gilbert Rd, Winter Park, FL 32792

Home Highlights

Property Type
Single-Family Home
Living Area
1,692 sqft
Price/Sqft
$312
Parking
Attached Garage

Local Information

  • Map ViewExplore the area around 345 Gilbert Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Welcome to 345 Gilbert Rd, a beautifully maintained mid-century 3-bedroom, 2-bathroom home in the highly sought-after Winter Park Pines neighborhood, five minute walking distance to Cady Way trail, pickleball and tennis courts.

Perfect for a family, this home offers an ideal split-bedroom layout, with the master bedroom on one side and the two additional bedrooms on the other. The bright, modern interior features natural light, gleaming wood floors, comfortable living spaces, and classic mid-century charm with modern updates.

The casual dining area opens through sliding glass doors to a private fenced backyard with a sparkling swimming pool perfect for relaxing, entertaining, and enjoying Florida living.

The location is truly the highlight: close to excellent schools, zoned for Winter Park High School, and minutes from Park Avenue, Cady Way Trail, Winter Park Hospital, Winter Park Center for Health and Wellbeing, Winter Park Pines Golf Club, tennis and pickleball courts, community pool, shopping, dining, and everyday Winter Park amenities.

Additional highlights include a 2-car attached garage and a quiet, desirable neighborhood setting.

Available July 15. A 24-hour notice is required for tenant showings.
345 Gilbert Rd, Winter Park, FL 32792 is a 3 bedroom, 2 bathroom, 1,692 sqft single-family home. It last sold for $299,000 on Jul 29, 2019 (8,148% above the $3,625 asking price). More recently, it was listed as a rental in May 2026 with an asking price of $3,550 per month. That rental listing was removed on June 9, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $528,600, with a rent estimate of $3,591/month.

Home Details for 345 Gilbert Rd

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: Central AirHeating Fuel: Heat Pump
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Pool
Pool
Parking & Garage
Parking: Attached, On Site

Comparable Sales for 345 Gilbert Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2756 SHERIFF WAY, Winter Park, FL
0.04
Single-Family Home
$588,000
07/08/26
3
2
1,812 sqft
2708 LION HEART ROAD, Winter Park, FL
0.18
Single-Family Home
$435,000
12/11/25
3
2
1,785 sqft
402 SAINT DUNSTAN WAY, Winter Park, FL
0.08
Single-Family Home
$656,402
09/05/25
3
2
1,779 sqft
2748 LION HEART ROAD, Winter Park, FL
0.17
Single-Family Home
$475,000
03/16/26
3
2
1,502 sqft
528 SAINT DUNSTAN WAY, Winter Park, FL
0.20
Single-Family Home
$536,000
08/19/26
3
2
1,656 sqft
2833 PRINCE JOHN ROAD, Winter Park, FL
0.21
Single-Family Home
$400,000
02/13/26
4
2
1,605 sqft
2814 SHERIFF WAY, Winter Park, FL
0.09
Single-Family Home
$545,000
04/22/26
4
2
1,948 sqft
513 CORNWALL ROAD, Winter Park, FL
0.19
Single-Family Home
$629,000
04/03/26
3
2
1,735 sqft
2831 LION HEART ROAD, Winter Park, FL
0.25
Single-Family Home
$460,000
12/05/25
3
2
1,978 sqft
101 S RANGER BOULEVARD, Winter Park, FL
0.25
Single-Family Home
$515,000
10/06/25
3
2
1,600 sqft

Nearby homes

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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
    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
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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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LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Jun 9, 2026
Source: Zillow Rentals
ListingRemoved
$3,625
Jun 2, 2026
Source: Zillow Rentals
PriceChange
$3,625
Price increased by 2%
May 27, 2026
Source: Zillow Rentals
Listed For Rent
$3,550
Jun 23, 2025
Source: Stellar MLS #O6308417
ListingRemoved
$3,400
Jun 7, 2025
Source: Stellar MLS #O6308417
PriceChange
$3,400
Price decreased by 7%

Frequently asked questions about 345 Gilbert Rd

  • What is 345 Gilbert Rd estimated to be worth?
    Trulia's estimated value for 345 Gilbert Rd in Winter Park, FL is $528,600.
  • What is the price history for 345 Gilbert Rd?
    345 Gilbert Rd in Winter Park, FL last sold for $299,000 in July 2019.
  • 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 345 Gilbert Rd have air conditioning?
    Yes, 345 Gilbert Rd in Winter Park, FL has air conditioning.
  • Does 345 Gilbert Rd have a pool?
    Yes, 345 Gilbert Rd in Winter Park, FL has a pool.

Homes for rent near 345 Gilbert Rd

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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