744 Bear Creek Cir, Winter Springs, FL 32708
OFF MARKET

744 Bear Creek Cir
Winter Springs, FL 32708

  • 4 Beds
  • 5 Baths
  • 5,160 sqft (on 0.96 acres)

$1,307,700

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $8,425/mo*
Refinance Your Home

$1,307,700

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $8,425/mo*
Refinance Your Home
4 Beds
5 Baths
5,160 sqft
(on 0.96 acres)

Home Value

Trulia Estimate
$1.31M
Since last month
Decreased$13K (-1%)
Since last year
Increased$81K (+6.6%)
Since last sale
Increased$418K (+46.9%)
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 +82% in the last 10 years
MonthEstimated value
2026
August 2026$1.31M
July 2026$1.32M
June 2026$1.33M
May 2026$1.34M
April 2026$1.32M
March 2026$1.26M
February 2026$1.23M
January 2026$1.2M
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
716 BEAR CREEK CIRCLE, Winter Springs, FL
0.05
Single-Family Home
$1,175,000
05/22/26
5
5
4,382
1502 BLACK BEAR COURT, Winter Springs, FL
0.15
Single-Family Home
$1,330,000
05/06/26
5
4.5
3,718
1513 BLACK BEAR COURT, Winter Springs, FL
0.19
Single-Family Home
$1,320,000
06/29/26
4
5
6,175
699 BEAR PAW COURT, Winter Springs, FL
0.23
Single-Family Home
$1,500,000
01/30/26
7
5
4,260
775 BEAR CREEK CIRCLE, Winter Springs, FL
0.18
Single-Family Home
$1,310,000
08/25/25
5
3
3,494
704 Forest View Ct, Winter Springs, FL
0.63
Single-Family Home
$920,000
02/13/26
4
4
3,068
1566 CARRINGTON AVENUE, Winter Springs, FL
0.30
Single-Family Home
$665,000
03/30/26
4
3.5
2,554
104 THUNBERG COVE, Winter Springs, FL
0.39
Single-Family Home
$855,000
03/24/26
6
3
3,702
1470 CONNORS LANE, Winter Springs, FL
0.25
Single-Family Home
$559,000
02/12/26
3
3
2,428
109 CHERRY CREEK CIRCLE, Winter Springs, FL
0.60
Single-Family Home
$1,010,000
08/06/26
5
4
3,440

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
740 BEAR CREEK CIRCLE, Winter Springs, FL 32708
0.06
$1,258,000
4
3.5
3,442
Off Market
716 BEAR CREEK CIRCLE, Winter Springs, FL 32708
0.05
$1,175,000
5
5
4,382
Recently Sold
772 BEAR CREEK CIRCLE, Winter Springs, FL 32708
0.12
$1,281,500
5
5.5
5,410
Off Market
776 BEAR CREEK CIRCLE, Winter Springs, FL 32708
0.12
$1,115,500
5
3.5
3,151
Off Market
1502 BLACK BEAR COURT, Winter Springs, FL 32708
0.15
$1,330,000
5
4.5
3,718
Recently Sold
1704 DAVENPORT COURT, Winter Springs, FL 32708
0.22
$562,800
3
2
2,101
Off Market
1703 STOCKPORT STREET, Winter Springs, FL 32708
0.23
$533,900
4
2
2,413
Off Market
1702 DAVENPORT COURT, Winter Springs, FL 32708
0.23
$570,000
3
2
2,101
Recently Sold
775 BEAR CREEK CIRCLE, Winter Springs, FL 32708
0.18
$1,294,400
5
3
3,494
Off Market
731 BEAR CREEK CIRCLE, Winter Springs, FL 32708
0.20
$1,398,300
4
3.5
3,722
Off Market
1551 WARRINGTON STREET, Winter Springs, FL 32708
0.25
$686,000
4
3
2,417
Recently Sold
1513 BLACK BEAR COURT, Winter Springs, FL 32708
0.19
$1,320,000
4
5
6,175
Recently Sold

Local Information

  • Map ViewExplore the area around 744 Bear Creek Cir.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1988
Lot Size
0.96 acres
Living Area
5,160 sqft
Price/Sqft
$253
Parking
Garage

About this House

This single-family home is located at 744 Bear Creek Cir, Winter Springs, FL. 744 Bear Creek Cir is in Winter Springs, FL and in ZIP code 32708. This property has 4 bedrooms, 5 bathrooms and approximately 5,160 sqft of floor space. This property has a lot size of 0.96 acres and was built in 1988.
744 Bear Creek Cir, Winter Springs, FL 32708 is a 4 bedroom, 5 bathroom, 5,160 sqft single-family home built in 1988. It last sold for $890,000 on Dec 9, 2021. It is currently off market. The Trulia Estimate is $1,307,700, with a rent estimate of $5,641/month.

Home Details for 744 Bear Creek Cir

Interior Features

Interior Details
Basement
Levels, Entrance, & Accessibility
Stories: 2Floors: Other
Heating & Cooling
Air ConditioningCooling System: Central
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionExterior: Stucco, WoodFoundation Type: Footing
Pool
Pool
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 1988Year Updated: 1988
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.96 acres

Price and Tax history

DateEventPrice
Dec 4, 2024
Source: Stellar MLS #O5944611
ListingRemoved
$899,000
Dec 4, 2023
Source: Stellar MLS #O5944611
ListingRemoved
Dec 9, 2021
Source: N/A
Sold
$890,000
Oct 29, 2021
Source: Stellar MLS #O5944611
Pending
$899,000
Oct 11, 2021
Source: Stellar MLS #O5944611
PriceChange
$899,000
Price decreased by 5%

Market trends in Winter Springs

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$406K
$10.67KMoM
Sale-to-List Price
98.5%
0.2%MoM
Price per sq ft
$230
$6MoM
Available listings
191
9MoM

Around this home

What Locals Say about Winter Springs

At least 325 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 89 % Say car is needed

  • 87 % Say there are sidewalks

  • 85 % Say parking is easy

  • 76 % Say it's quiet

  • 76 % Say there's holiday spirit

  • 69 % Say kids play outside

  • 69 % Say yards are well-kept

  • 68 % Say people would walk alone at night

  • 66 % Say streets are well-lit

  • 55 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 48 % Say it's walkable to grocery stores

  • 47 % Say there's wildlife

  • 46 % Say it's walkable to restaurants

  • 31 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Fnybound
    "Great area to raise a Family "
    0
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  • Trulia User
    "Winter Springs is a beautiful and family-friendly community known for its peaceful neighborhoods, great schools, parks, and strong local connections. The city offers a perfect balance of nature and modern living, with walking trails, community events, and local businesses that make residents feel at home. Winter Springs continues to grow while maintaining its welcoming small-town atmosphere and community pride."
    0
    Flag
  • Jacinda.de_jesus
    "People here are usually very friendly. I’ve met a lot of nice neighbors while on walks and they always say hello, sometimes even hold full conversations about my dogs. My neighbors look out for me and I do the same for them. "
    0
    Flag
  • heisa pulgarin
    "Is a very safe and clean area to live in, very green and peaceful, if you’re looking for a place close to stores , and with variety this is the place , all the stores are around winter springs , schools,churches and grocery stores are literally minutes :)"
    0
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  • Ismel
    "Great neighborhood, very quiet place to live, is near to a lot of markets very secure, a dog friendly neighborhood "
    0
    Flag
  • Jayme Messana
    "Lots of parks; great neighborhood! Very friendly people in the area Some neighborhoods do not have sidewalks. But that is okay for us. Just be careful crossing streets of course. "
    0
    Flag
  • Trulia User
    "Neighborhood is quite well maintained and is safer than most locations. Stores are nearby , supermarkets etc.. "
    0
    Flag
  • Kbarontini
    "The people that complain about dogs being walked and owners not picking up after them. Also dogs urinatiing in the grass. Dogs must be on leash always. No where for them to run."
    1
    Flag
  • Jhxr74
    "There are many areas to walk dogs. We are happy that owners police the area when the dog does it's business."
    3
    Flag
  • Emelinda10
    "The area is very clean, great parks, easy traffic. Close to major stores. The whole are is new a lot of restaurants and green areas. "
    2
    Flag
  • Kimberly_Vach
    "It’s a great place to raise kids and the county is an A+ school district! You are far enough away for privacy, but close enough to be involved in whatever your family chooses."
    0
    Flag
  • Christine
    "Dogs are on leash at all times. When meeting other dogs, owners are good about asking for pet introductions."
    0
    Flag
  • Erica G.
    "My mother lives in the area and has been for the last 10yrs. We have always felt very safe and it’s always clean."
    2
    Flag
  • Tina B.
    "quarterly neighborhood parties, great schools, safe and good neighbors of all backgrounds get along "
    0
    Flag
  • Laxsurfer1117
    "I’ve lived here since I was a kid and I’m 28 now, never had any huge issues wherever I’ve lived. Overall winter springs is very community driven and that’s what makes it unique."
    1
    Flag
  • Bobbie V.
    "Winter springs, in general, is fine. Nothing really going on here, but it is not a bad place to live. My street and the area surrounding me are not great, but to be fair, I only the people living next to us (fairly social guy, myself) and they ARE nice and cool. I have heard so many bad things, the police are ALWAYS in and out of my neighborhood AND held my girlfriend up for questioning as she walked out of our back door because they thought I was somebody else. We’re trying to move out of here. TL;DR: Winter Springs: Nothing going on, Not an awful spot, stay off Lori Anne Ln and maybe the block or two around it."
    0
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  • Darren J. W.
    "Living at the apartments is always going to be tricky but for the most part the leasing offices do an amazing job; when it comes to the people living there, just be aware that some care and some don’t. "
    0
    Flag
  • Angeltillis
    "The neighborhood is very family friendly and the public areas are beautiful. It is a very safe and nice neighborhood."
    0
    Flag
  • Nellieroth
    "You can walk your dog, seems like most people have a dog in this neighborhood, so don’t think you’ll have a problem feeling welcomed. "
    0
    Flag
  • Shelby S.
    "No dog park or large area for them to run and play. Not many other dogs in the neighborhood.. not many big back yards either"
    0
    Flag
  • Joelchoate5
    "I have lived in the neighborhood for 5 years And it's a nice place to raise your children It's generally a quiet and peaceful place"
    0
    Flag
  • Jrutherf32708
    "I have lived in Winter Springs / Tuskawilla area over 25 years. It’s been an excellent place to live and raise 3 children. We have never any problems with crime or neighbors. Great public schools here ; all “A” rated. I highly recommend this area !"
    0
    Flag
  • Abdul I.
    "Diversity and everyone is polite. People mind their own business but also friendly. Affordable rent and education in local school is relatively high standards. "
    0
    Flag
  • Robin M.
    "There are great spaces and wide sidewalks with lots of green area. Plus a huge dog park right in the middle of the town"
    5
    Flag
  • Kimberly P.
    "Close to 417 and main highways for easy travel. Near Orlando for attractions and fun. Schools are rated A. "
    1
    Flag
  • Miketabo
    "good, safe. the school system is great just have to travel to oviedo for shopping and restaurants. but it is very family friendly in winter springs"
    0
    Flag
  • Pam
    "Annual Family Picnic. Very neighborly neighborhood. Lots of children and activities for them through out the year. "
    0
    Flag
  • Cindysnead28
    "No sidewalks kids ride bikes in streets not safe the kids need to watch out for cars and trucks sidewalks are needed badl"
    0
    Flag
  • Shirley R.
    "I love this neighborhood it’s safe and secluded but still close enough to all the action. Great schools "
    0
    Flag
  • Arniearmadillo
    "Plenty of public transportation options and access to multiple highway options. Great restaurants and shopping options."
    0
    Flag
  • Signupzachary
    "Great place to raise a family or for new home owners. Close to a lot but also very quiet. The city is growing and has lot to offer but it’s also close to a main highway that can cause working in a different part of ORLANDO much easier "
    0
    Flag
  • Marie B.
    "Heavy traffic at peak hours but not outrageous. Not too bad. Traffic is thick around schools. Toll roads help. "
    0
    Flag
  • Colleen J.
    "Right off of numerous major roads, but also tucked back away from the chaos. Close to I4 making for a easy commute in multiple directions "
    0
    Flag
  • Nancyn425
    "Our neighbors care about each other and go out of their way to help each other. We make meals for each other, talk often, have get togethers for Halloween, 4th of July, Super Bowl, etc."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 744 Bear Creek Cir

  • What is 744 Bear Creek Cir estimated to be worth?
    Trulia's estimated value for 744 Bear Creek Cir in Winter Springs, FL is $1,307,700.
  • What is the price history for 744 Bear Creek Cir?
    744 Bear Creek Cir in Winter Springs, FL last sold for $890,000 in December 2021.
  • Is Winter Springs a buyer's or seller's market?
    Winter Springs is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Springs?
    The median sale price in Winter Springs is $406K. That is down $10.67K from the prior month.
  • Does 744 Bear Creek Cir have air conditioning?
    Yes, 744 Bear Creek Cir in Winter Springs, FL has air conditioning.
  • Does 744 Bear Creek Cir have a pool?
    Yes, 744 Bear Creek Cir in Winter Springs, FL has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Outdoor Space

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Off Market Homes Near 744 Bear Creek Cir

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