Winter Springs
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22 Homes

Winter Springs, FL homes for sale under $300,000

In the last 30 days, Winter Springs home prices were up 7.5% compared to last year. The median price of a home was $429,900. View Winter Springs Market Insights

1 / 30
New 52 Minutes Ago
Winter Springs
418 San Gabriel St #418
418 San Gabriel St #418
  • 2 beds
  • 1 bath
  • 759 sqft
$219,000
1 / 36
Winter Springs
737 Sherwood Dr
737 Sherwood Dr
  • 2 beds
  • 2 baths
  • 1,248 sqft
$298,500
1 / 45
Winter Springs
4004 Garden Oak Ct
4004 Garden Oak Ct
  • 2 beds
  • 2.5 baths
  • 1,306 sqft
$300,000
1 / 30
Winter Springs
314 San Gabriel St
314 San Gabriel St
  • 3 beds
  • 2 baths
  • 1,091 sqft
$285,990
1 / 36
Price Drop
Winter Springs
1340 Delaney Dr
1340 Delaney Dr
  • 3 beds
  • 2 baths
  • 1,422 sqft
$276,400
$279,900
1 / 24
Price Drop
Winter Springs
346 Casa Grande Dr
346 Casa Grande Dr
  • 2 beds
  • 2 baths
  • 828 sqft
$42,000
$44,000
1 / 39
Price Drop
Winter Springs
Undisclosed
Undisclosed
  • 3 beds
  • 2 baths
  • 1,192 sqft
$299,000
$310,000
1 / 41
Winter Springs
505 Moree Loop
505 Moree Loop
  • 2 beds
  • 2.5 baths
  • 1,434 sqft
$249,900
1 / 15
Price Drop
Winter Springs
10 Sheoah Blvd #5
10 Sheoah Blvd #5
  • 2 beds
  • 2 baths
  • 972 sqft
$174,900
$184,900
1 / 35
Price Drop
Winter Springs
80 Moree Loop #10
80 Moree Loop #10
  • 3 beds
  • 2 baths
  • 1,187 sqft
$159,999
$175,000
1 / 26
Price Drop
Winter Springs
411 Green Spring Cir
411 Green Spring Cir
  • 3 beds
  • 1.5 baths
  • 1,130 sqft
$232,000
$239,900
1 / 32
Price Drop
Winter Springs
30 Moree Loop #39
30 Moree Loop #39
  • 3 beds
  • 2.5 baths
  • 1,400 sqft
$210,000
$219,000
1 / 7
Price Drop
Winter Springs
201 Bennett St
201 Bennett St
  • 4 beds
  • 2.5 baths
  • 1,405 sqft
$299,000
$310,000
1 / 50
Price Drop
Winter Springs
718 Lakeside Dr
718 Lakeside Dr
  • 2 beds
  • 2 baths
  • 1,166 sqft
$289,000
$298,900
1 / 24
Winter Springs
40 Moree Loop #11
40 Moree Loop #11
  • 3 beds
  • 2.5 baths
  • 1,400 sqft
$179,000
1 / 47
Winter Springs
600 Northern Way #502
600 Northern Way #502
  • 3 beds
  • 2 baths
  • 1,425 sqft
$284,900
1 / 23
Price Drop
Winter Springs
421 Tradition Ln
421 Tradition Ln
  • 2 beds
  • 2.5 baths
  • 1,275 sqft
$299,900
$304,900
1 / 27
Winter Springs
4522 Brook Hollow Cir
4522 Brook Hollow Cir
  • 2 beds
  • 1.5 baths
  • 1,108 sqft
$270,000
1 / 22
Price Drop
Winter Springs
294 San Gabriel St
294 San Gabriel St
  • 2 beds
  • 2 baths
  • 1,105 sqft
$255,000
$260,000
1 / 27
Winter Springs
498 Club Dr
498 Club Dr
  • 2 beds
  • 2 baths
  • 1,224 sqft
$250,000
1 / 42
Price Drop
Winter Springs
206 Charles St
206 Charles St
  • 4 beds
  • 1 bath
  • 1,120 sqft
$295,900
$299,900
1 / 28
Price Drop
Winter Springs
4113 Hedge Maple Pl #4113
4113 Hedge Maple Pl #4113
  • 2 beds
  • 2.5 baths
  • 1,330 sqft
$290,000
$295,000
Viewing 1-22 of 22 homes

Frequently Asked Questions

What is the median home sale price in Winter Springs, FL?
In the last 30 days, the median home sale price in Winter Springs was $429,900, up 7.5% compared to the same period last year. The "median" price is the middle price - half of the homes here were sold for less, the other half for more.
How many homes are for sale in Winter Springs, FL?
There were 123 homes for sale in Winter Springs as of November 02, 2025. There were 42 new listings within the last 30 days as well. The more homes on the market, the more choices buyers have.
How up-to-date are Orchard's new listings in Winter Springs, FL?
The new homes and houses for sale on Orchard's listings pages are updated hundreds of times each day, with listings in Winter Springs last seen updated at . New listings can appear every day, but many listings first appear on the market mid-week.
How much competition is there to buy a home in Winter Springs, FL?
In the last 30 days, the median number of days a home in Winter Springs remained on the market (DOM) was 42. In areas with a low DOM, homes are sold quickly and the competition is fierce; in areas with higher DOMs, you may have more options and more time to make an offer.