4235 Bear Gully Rd, Winter Park, FL 32792
Property image
Property image
OFF MARKET

$2,776,300

Trulia Estimate
  • 5 Beds
  • 5 Baths
  • 6,001 sqft (on 0.91 acres)

4235 Bear Gully Rd, Winter Park, FL 32792

Est. Refi. Payment $19,631/mo*
Refinance Your Home
Currently Off Market - Sold May 30, 2018 for $1,650,000

Home Value

Trulia Estimate
$2.78M
Since last month
Decreased$37K (-1.3%)
Since last year
Increased$93K (+3.5%)
Since last sale
Increased$1M (+68.3%)
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 +67% in the last 10 years
MonthEstimated value
2026
September 2026$2.78M
August 2026$2.81M
July 2026$2.8M
June 2026$2.82M
May 2026$2.79M
April 2026$2.74M
March 2026$2.72M
February 2026$2.72M
January 2026$2.66M
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
2820 BEAR ISLAND POINTE, Winter Park, FL
0.18
Single-Family Home
$2,000,000
05/11/26
3
4.5
5,138
4469 OLD BEAR RUN, Winter Park, FL
0.39
Single-Family Home
$1,700,000
09/11/26
5
4.5
4,288
2880 OLD CASTLE DRIVE, Winter Park, FL
0.26
Single-Family Home
$1,010,000
09/30/25
5
4.5
3,839
4048 GILDER ROSE PLACE, Winter Park, FL
0.38
Single-Family Home
$1,206,400
10/15/25
4
3.5
3,321
2890 WILD GINGER COURT, Winter Park, FL
0.33
Single-Family Home
$893,000
10/09/25
4
4.5
3,408
5325 Cypress Reserve Pl, Winter Park, FL
0.23
Single-Family Home
$905,000
03/17/26
5
3.5
3,598
4190 BEAR GULLY ROAD, Winter Park, FL
0.11
Single-Family Home
$465,000
07/07/26
4
2.5
2,058
1460 VIA SANGRO PLACE, Winter Park, FL
0.81
Single-Family Home
$1,500,000
12/23/25
7
4
5,111
7895 PLEASANT PINE CIRCLE, Winter Park, FL
0.37
Single-Family Home
$719,000
11/19/25
5
3.5
3,568
4536 N LANDMARK DRIVE, Orlando, FL
0.84
Single-Family Home
$1,375,000
10/10/25
4
3.5
3,687

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
4200 BEAR GULLY ROAD, Winter Park, FL 32792
0.09
$523,600
4
3
1,945
Off Market
4190 BEAR GULLY ROAD, Winter Park, FL 32792
0.11
$465,000
4
2.5
2,058
Recently Sold
2832 BEAR ISLAND POINTE, Winter Park, FL 32792
0.13
$1,142,000
5
5
3,983
Off Market
5559 PATS POINT, Winter Park, FL 32792
0.17
$385,600
3
2
1,613
Off Market
2835 BEAR ISLAND POINTE, Winter Park, FL 32792
0.17
$733,900
4
3.5
2,902
Off Market
2820 BEAR ISLAND POINTE, Winter Park, FL 32792
0.18
$2,000,000
3
4.5
5,138
Recently Sold
5520 S LAKE BURKETT LANE, Winter Park, FL 32792
0.24
$497,800
3
3
1,990
Off Market
5530 S LAKE BURKETT LANE, Winter Park, FL 32792
0.25
$451,000
3
2.5
1,669
Recently Sold
8073 PLEASANT PINE CIRCLE, Winter Park, FL 32792
0.26
$620,600
4
3
2,319
Off Market
5332 CYPRESS RESERVE PLACE, Winter Park, FL 32792
0.24
$825,000
5
3.5
3,241
Off Market
8097 PLEASANT PINE CIRCLE, Winter Park, FL 32792
0.27
$542,900
4
2
2,003
Off Market
2884 OLD CASTLE DRIVE, Winter Park, FL 32792
0.27
$1,181,900
4
3.5
3,381
Off Market

Local Information

  • Map ViewExplore the area around 4235 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 2012
0.91 acre lot
6,001 sqft
$463/sqft
Garage

About this House

You can have it all in your Winter Park Lakefront Home on coveted spring fed BEAR GULLY LAKE! Elevate to an UNMATCHED LIFESTYLE filled with lake living. The impressive private gated entry welcomes you home to a true oasis. Worries melt away in your grand estate. Designed around the lake, all living spaces offer stunning panoramic views through walls of windows allowing for abundant natural light. Upon entry of your two story living and dining room, you'll fall in love with the soaring ceiling, dramatic curved iron staircase, impressive fireplace, built-in bar, gorgeous crystal chandelier, and sweeping view. Your friends will envy your kitchen equipped with WOLF and SUBZERO appliances and EXOTIC GRANITE. The first-floor private master retreat rivals even the most luxurious of resorts. Wake up every day to your beautiful serene view & personal coffee bar, and luxuriate in your spa-like master bath. Additional bedrooms are ensuites with unique COFFERED CEILINGS. Continuing quality spills from the inside out as you enjoy your spacious CABANA with an OUTDOOR KITCHEN, the heated private pool, spa and outdoor gas fireplace. Sunset cruises, skiing, paddle-boarding, fishing & more are just a few steps away! With highly desired SEMINOLE COUNTY SCHOOLS, close proximity to Trinity Preparatory and Master's Academy, you can enjoy the prestigious Winter Park lifestyle without the congestion. The ENERGY EFFICIENCY of this home makes this both a beautiful and smart choice. Enjoy the lake lifestyle & make this home yours!
4235 Bear Gully Rd, Winter Park, FL 32792 is a 5 bedroom, 6 bathroom, 6,001 sqft single-family home built in 2012. It last sold for $1,650,000 on May 30, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,776,300, with a rent estimate of $7,445/month.

Home Details for 4235 Bear Gully Rd

Interior Features

Interior Details
BasementTypes of Rooms: Walk In Closet, Dining RoomWet BarCeiling Fan
Heating & Cooling
Heating: Electric, GasAir ConditioningCooling System: CentralHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DishwasherMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: StuccoFoundation Type: FootingPatioPorch
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2012Year Updated: 2012
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.91 acres

Price and Tax history

DateEventPrice
May 30, 2018
Source: N/A
Sold
$1,650,000
Mar 19, 2018
Source: Agent Provided
PriceChange
$1,700,000
Price decreased by 6%
Feb 7, 2018
Source: Agent Provided
Listed For Sale
$1,800,000
Aug 31, 2016
Source: Agent Provided
ListingRemoved
$1,799,999
May 21, 2016
Source: Agent Provided
Pending
$1,799,999

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
    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
    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 4235 Bear Gully Rd

  • What is 4235 Bear Gully Rd estimated to be worth?
    Trulia's estimated value for 4235 Bear Gully Rd in Winter Park, FL is $2,776,300.
  • What is the price history for 4235 Bear Gully Rd?
    4235 Bear Gully Rd in Winter Park, FL last sold for $1,650,000 in May 2018.
  • 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 4235 Bear Gully Rd have air conditioning?
    Yes, 4235 Bear Gully Rd in Winter Park, FL has air conditioning.
  • Does 4235 Bear Gully Rd have a pool?
    Yes, 4235 Bear Gully Rd in Winter Park, FL has a pool.

Explore by feature - Pet Friendly

158 pet-friendly rentals in Winter Park, FL

Explore by feature - Garage

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

Explore by feature - Outdoor Space

57 rentals with an outdoor space in Winter Park, FL

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