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

$564,500

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 1,848 sqft

345 Fleet Rd, Winter Park, FL 32792

Est. Refi. Payment $4,088/mo*
Refinance Your Home
Currently Off Market - Sold Aug 4, 2014 for $272,000

Home Value

Trulia Estimate
$565K
Since last month
Decreased$4K (-0.7%)
Since last year
Increased$25K (+4.6%)
Since last sale
Increased$291K (+106.9%)
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 +84% in the last 10 years
MonthEstimated value
2026
September 2026$563K
August 2026$565K
July 2026$567K
June 2026$571K
May 2026$570K
April 2026$565K
March 2026$558K
February 2026$556K
January 2026$543K
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
326 FITZHUGH ROAD, Winter Park, FL
0.10
Single-Family Home
$502,000
02/25/26
4
3
1,835
2681 FITZHUGH ROAD, Winter Park, FL
0.08
Single-Family Home
$765,000
05/20/26
4
2.5
2,375
2652 ABBEY ROAD, Winter Park, FL
0.02
Single-Family Home
$625,000
07/30/26
5
2
1,938
332 FLEET ROAD, Winter Park, FL
0.04
Single-Family Home
$600,000
07/21/26
4
2
2,355
2648 AMSDEN ROAD, Winter Park, FL
0.09
Single-Family Home
$450,000
10/31/25
3
2
1,623
2743 MERRIE OAKS ROAD, Winter Park, FL
0.15
Single-Family Home
$445,000
01/22/26
3
2
1,661
324 Beckett Ct, Winter Park, FL
0.25
Single-Family Home
$244,000
12/31/25
3
2
1,957
308 Beckett Ct, Winter Park, FL
0.25
Single-Family Home
$490,000
10/29/25
4
2
1,912
2708 LION HEART ROAD, Winter Park, FL
0.25
Single-Family Home
$435,000
12/11/25
3
2
1,785
275 N RANGER BOULEVARD, Winter Park, FL
0.27
Single-Family Home
$759,000
08/27/26
4
3
1,950

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
2652 ABBEY ROAD, Winter Park, FL 32792
0.02
$625,000
5
2
1,938
Recently Sold
232 BALFOUR DRIVE #19, Winter Park, FL 32792
0.04
$317,600
2
2
1,287
Off Market
332 FLEET ROAD, Winter Park, FL 32792
0.04
$600,000
4
2
2,355
Recently Sold
264 BALFOUR DRIVE, Winter Park, FL 32792
0.06
$384,500
3
2.5
1,727
Off Market
228 BALFOUR DRIVE #17, Winter Park, FL 32792
0.05
$302,600
2
2
1,287
Off Market
2630 AMSDEN ROAD, Winter Park, FL 32792
0.07
$471,000
3
2
1,800
Off Market
218 BALFOUR DRIVE #12, Winter Park, FL 32792
0.07
$289,500
2
2
1,256
Off Market
222 BALFOUR DRIVE #14, Winter Park, FL 32792
0.07
$292,300
2
2
1,256
Off Market
2648 AMSDEN ROAD, Winter Park, FL 32792
0.09
$448,600
3
2
1,623
Off Market
2681 FITZHUGH ROAD, Winter Park, FL 32792
0.08
$765,000
4
2.5
2,375
Recently Sold
2667 FITZHUGH ROAD, Winter Park, FL 32792
0.08
$642,200
5
3
2,812
Off Market
326 FITZHUGH ROAD, Winter Park, FL 32792
0.10
$502,000
4
3
1,835
Recently Sold

Local Information

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

Home Highlights

Single-Family Home
Built in 1967
1,848 sqft
$305/sqft
Garage

About this House

TRADITIONAL SALE. Original Owner. This is your OPPORTUNITY to buy in the established and sought-after community of WINTER PARK PINES!!! SPACIOUS 4 Bdrm/3 Bath POOL HOME, w/SPLIT FLOOR PLAN and PLENTY of CLOSET/STORAGE. Situated on a large FENCED lot, on a QUIET, TREE LINED street OFF the MAIN ROAD. Among the home's features: a FRONT PORCH shelters the Main Entry and takes visitors to the FOYER and large LIVING RM and DINING RM area. The Living Room's large windows bring loads of natural light into the room. The KITCHEN opens to the FAMILY ROOM and has views to the LARGE POOL and BACKYARD. Near the Family Rm, there are 3 LARGE BEDROOMS plus 2 FULL BATHS (one is a pool bath and the other a Jack & Jill bath). The OTHER SIDE of the HOUSE contains the MASTER BATHROOM and BEDROOM which also overlooks the pool/backyard. Both, Family Rm and Master Bedroom have sliding glass doors into a large SCREENED PORCH (32' x 14') that leads to the POOL and NEW DECK area. The Pool was completely UPDATED and RESURFACED in 2012; a brand new DECK was done at that time. There is terrazzo floor throughout. A NEW ROOF just installed in July 2013. House completely re-plumbed a few years back. HOA is Optional. Highly rated Winter Park Schools! Near Cady Way, Ward Memorial Park with playgrounds, sports fields and YMCA pool, etc. It's less than a mile to Winter Park Golf Course. HOME needs some TLC & UPDATING...WHAT A GREAT OPPORTUNITY TO MAKE IT YOUR STYLE! Come and see TODAY all this house offers.
345 Fleet Rd, Winter Park, FL 32792 is a 4 bedroom, 3 bathroom, 1,848 sqft single-family home built in 1967. It last sold for $272,000 on Aug 4, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $564,500, with a rent estimate of $2,936/month.

Home Details for 345 Fleet Rd

Interior Features

Heating & Cooling
Heating: Forced AirCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1

Exterior Features

Exterior Home Features
Roof: Other
Pool
Pool
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 1967Year Updated: 1977
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 10413 sqft

Price and Tax history

DateEventPrice
Aug 4, 2014
Source: N/A
Sold
$272,000
Oct 2, 2013
Source: N/A
Sold
$220,000
Jul 24, 2013
Source: Agent Provided
Listed For Sale
$245,000

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

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
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  • 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
    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
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LGBTQ Local Legal Protections

Frequently asked questions about 345 Fleet Rd

  • What is 345 Fleet Rd estimated to be worth?
    Trulia's estimated value for 345 Fleet Rd in Winter Park, FL is $564,500.
  • What is the price history for 345 Fleet Rd?
    345 Fleet Rd in Winter Park, FL last sold for $272,000 in August 2014.
  • 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 $455K. That is up $4.03K from the prior month.
  • Does 345 Fleet Rd have air conditioning?
    Yes, 345 Fleet Rd in Winter Park, FL has air conditioning.
  • Does 345 Fleet Rd have a pool?
    Yes, 345 Fleet Rd in Winter Park, FL has a pool.

Explore by feature - Pet Friendly

156 pet-friendly rentals in Winter Park, FL

Explore by feature - Garage

70 rentals with a garage in Winter Park, FL

Explore by feature - Air Conditioning

168 rentals with air conditioning in Winter Park, FL

Explore by feature - Pool

142 rentals with a pool in Winter Park, FL

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

Explore by feature - Outdoor Space

58 rentals with an outdoor space in Winter Park, FL

Apartments for Rent

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Off Market Homes Near 345 Fleet Rd

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