4280 Bear Gully Rd, Winter Park, FL 32792
OFF MARKET

$504,900

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 2,105 sqft (on 0.46 acres)

4280 Bear Gully Rd, Winter Park, FL 32792

Est. Refi. Payment $3,631/mo*
Refinance Your Home
Currently Off Market - Sold Feb 15, 2014 for $239,000

Home Value

Trulia Estimate
$505K
Since last month
Decreased$6K (-1.3%)
Since last year
Decreased$4K (-0.8%)
Since last sale
Increased$264K (+110.5%)
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 +76% in the last 10 years
MonthEstimated value
2026
September 2026$503K
August 2026$510K
July 2026$506K
June 2026$507K
May 2026$505K
April 2026$505K
March 2026$511K
February 2026$510K
January 2026$503K
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
4190 BEAR GULLY ROAD, Winter Park, FL
0.16
Single-Family Home
$465,000
07/07/26
4
2.5
2,058
8162 LAZY BEAR LANE, Winter Park, FL
0.32
Single-Family Home
$506,500
12/10/25
4
2
1,843
4649 CREEKVIEW LANE, Oviedo, FL
0.42
Single-Family Home
$368,100
04/28/26
4
2.5
2,069
4637 CREEKVIEW LANE, Oviedo, FL
0.41
Single-Family Home
$515,000
04/30/26
4
2
1,819
2507 CREEKVIEW CIRCLE, Oviedo, FL
0.54
Single-Family Home
$475,000
02/19/26
4
2
1,847
5530 S LAKE BURKETT LANE, Winter Park, FL
0.15
Single-Family Home
$451,000
08/17/26
3
2.5
1,669
8136 LAZY BEAR LANE, Winter Park, FL
0.38
Single-Family Home
$510,000
10/29/25
4
2
1,843
2530 CREEKVIEW CIRCLE, Oviedo, FL
0.54
Single-Family Home
$514,000
12/30/25
4
2.5
2,101
7864 PLEASANT PINE CIRCLE, Winter Park, FL
0.37
Single-Family Home
$550,000
10/23/25
4
2.5
2,182

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
5559 PATS POINT, Winter Park, FL 32792
0.09
$385,600
3
2
1,613
Off Market
5520 S LAKE BURKETT LANE, Winter Park, FL 32792
0.14
$497,800
3
3
1,990
Off Market
5530 S LAKE BURKETT LANE, Winter Park, FL 32792
0.15
$451,000
3
2.5
1,669
Recently Sold
5315 N LAKE BURKETT LANE, Winter Park, FL 32792
0.17
$549,500
4
2.5
2,188
Off Market
2832 BEAR ISLAND POINTE, Winter Park, FL 32792
0.14
$1,142,000
5
5
3,983
Off Market
2835 BEAR ISLAND POINTE, Winter Park, FL 32792
0.15
$733,900
4
3.5
2,902
Off Market
5285 N LAKE BURKETT LANE, Winter Park, FL 32792
0.19
$506,100
4
2.5
2,138
Off Market
4200 BEAR GULLY ROAD, Winter Park, FL 32792
0.14
$523,600
4
3
1,945
Off Market
5330 N LAKE BURKETT LANE, Winter Park, FL 32792
0.20
$545,900
4
2.5
2,130
Off Market
5332 CYPRESS RESERVE PLACE, Winter Park, FL 32792
0.18
$825,000
5
3.5
3,241
Off Market
8433 COMMANDER COVE, Winter Park, FL 32792
0.20
$455,000
4
2.5
1,903
For Sale
8413 COMMANDER COVE, Winter Park, FL 32792
0.19
$418,600
3
2.5
1,634
Off Market

Local Information

  • Map ViewExplore the area around 4280 Bear Gully Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2004
0.46 acre lot
2,105 sqft
$240/sqft
Garage

About this House

LOVELY, MOVE-IN READY CONTEMPORARY 4BR, 2BA home on almost ? ACRE lot with sought-after SEMINOLE COUNTY SCHOOLS and WINTER PARK ADDRESS! Enclosed Living Room could be used for an OFFICE OR 5TH BEDROOM! This WELL CONSTRUCTED CONCRETE BLOCK WITH METAL FRAME home has been lovingly maintained by the original owners. BRIGHT AND OPEN SPLIT FLOOR PLAN with VOLUME AND VAULTED CEILINGS and numerous decorator plant shelves. The kitchen features a breakfast bar as well as a bay window with a breakfast nook, and is open to the Family Room which has lovely architectural features. The MASTER BEDROOM is OVERSIZED and features a SPACIOUS Master BATH with a Garden Tub, Separate Shower and Dual Sinks! This inviting home features a covered patio, additional bricked patio area and the interior living areas were NEWLY PAINTED. This property also features an INSIDE UTILITY AREA; a security system; sprinkler system with a separate meter; an EXTENDED GARAGE; gutter system; AND an EXTRA LONG DRIVEWAY! A portion of the back yard is fenced in -- perfect for pets or little ones, but the entire yard is much larger and mostly open. This RARE, NEWER HOME in an established Winter Park neighborhood is ONE OF THE BEST VALUES AROUND & an easy conventional sale! Convenient location just minutes to Seminole County Bike Trail, 417, UCF, Research Park, Siemens, Full Sail & Valencia Community College; 10 MIN. TO DOWNTOWN WINTER PARK & 15 MIN. TO DOWNTOWN ORLANDO AND THE INTERNATIONAL AIRPORT! Includes a one-year home warranty.
4280 Bear Gully Rd, Winter Park, FL 32792 is a 4 bedroom, 2 bathroom, 2,105 sqft single-family home built in 2004. It last sold for $239,000 on Feb 15, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $504,900, with a rent estimate of $2,848/month.

Home Details for 4280 Bear Gully Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet
Interior Details
AtticTypes of Rooms: Dining Room, Family RoomCeiling Fan
Appliances & Utilities
DishwasherDisposalMicrowaveRefrigerator
Heating & Cooling
Air ConditioningCooling System: Central

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: Other, Stucco, MetalFoundation Type: FootingPatioPorchSprinkler System
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2004Year Updated: 2004
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.46 acres

Price and Tax history

DateEventPrice
Feb 15, 2014
Source: N/A
Sold
$239,000
Oct 5, 2013
Source: Agent Provided
Listed For Sale
$250,000
Jun 14, 2004
Source: N/A
Sold
$220,000

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
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  • 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
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  • 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
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  • 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
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  • 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 4280 Bear Gully Rd

  • What is 4280 Bear Gully Rd estimated to be worth?
    Trulia's estimated value for 4280 Bear Gully Rd in Winter Park, FL is $504,900.
  • What is the price history for 4280 Bear Gully Rd?
    4280 Bear Gully Rd in Winter Park, FL last sold for $239,000 in February 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 4280 Bear Gully Rd have air conditioning?
    Yes, 4280 Bear Gully Rd in Winter Park, FL has air conditioning.
  • How big is the lot at 4280 Bear Gully Rd?
    The lot at 4280 Bear Gully Rd in Winter Park, FL is about 0.46 acres (20,225 sq ft).

Explore by feature - Pet Friendly

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Off Market Homes Near 4280 Bear Gully Rd

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