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Highlands, Winter Springs, FL Homes for Sale | Realty.com

Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

Save search Advertise Sign In

Saved homes Saved searches Your tours Your inquiries Recently viewed Account settings

Registered offenders on the map

Show registered offenders (Florida and Texas)

Selling Options

What's my home worth?
Compare selling options
Get an instant cash offer
Buy before you sell

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

20 listings

Homes for Sale in Highlands, Winter Springs, FL

Homes for Sale in Highlands, Winter Springs, FL

20 Listings

Homes for Sale in Highlands, Winter Springs, FL

20 Listings

New26Active
$130,000
1 bd · 1 ba · 710 sqft
220 Moree Loop 1, Winter Springs, FL
Trace Christian, III · COLDWELL BANKER REALTY
28Active
$335,000
3 bd · 3 ba · 1,680 sqft
518 Harbor Winds Court, Winter Springs, FL
Michelle Richardson · KELLER WILLIAMS CLASSIC
42Active
$374,900
3 bd · 3 ba · 1,583 sqft
662 Nighthawk Circle, Winter Springs, FL
Carla Cabrera · MODERN WORLD REALTY LLC
36Active
$179,900
2 bd · 2 ba · 1,080 sqft
70 Moree Loop 61, Winter Springs, FL
Susan Schneider · COLDWELL BANKER REALTY
49Active
$350,000
2 bd · 2 ba · 1,502 sqft
321 Kirkcaldy Drive, Winter Springs, FL
Emily Halpern · COLDWELL BANKER REALTY
16Active
$329,000
3 bd · 3 ba · 1,680 sqft
472 Harbor Winds Court, Winter Springs, FL
Robert Arnold, Jr · SAND DOLLAR REALTY GROUP INC
Price Reduced39Active
$365,000
2 bd · 2 ba · 1,497 sqft
655 Nighthawk Circle, Winter Springs, FL
Bill Mauer · RE/MAX INNOVATION
Price Reduced58Active
$400,000
4 bd · 3 ba · 2,150 sqft
758 N Gretna Court, Winter Springs, FL
Nicholas Kovats · KELLER WILLIAMS ADVANTAGE REALTY
Price Reduced29Active
$140,000
1 bd · 1 ba · 710 sqft
220 Moree Loop 2, Winter Springs, FL
Patricia Woodhouse · RE/MAX CENTRAL REALTY
Price Reduced26Active
$354,000
3 bd · 3 ba · 1,792 sqft
830 Dunbar Terrace, Winter Springs, FL
Karen Albright · OPENDOOR BROKERAGE LLC
41Active
$199,000
3 bd · 2 ba · 1,187 sqft
429 Sheoah Boulevard 9, Winter Springs, FL
Freddy Escobar · LPT REALTY, LLC
Price Reduced35Active
$199,900
2 bd · 2 ba · 1,224 sqft
497 Club Drive, Winter Springs, FL
Edyta Olejnik · WATSON REALTY CORP
Price Reduced33Active
$475,000
3 bd · 2 ba · 1,857 sqft
629 Ryan Court, Winter Springs, FL
Lisa D'Orazio LLC · SOTERA LIVING
Price Reduced50Active
$329,900
3 bd · 2 ba · 1,178 sqft
335 Kirkcaldy Drive, Winter Springs, FL
Irina Carp · MILLENIUM REALTY GROUP
Price Reduced24Active
$176,000
3 bd · 2 ba · 1,187 sqft
240 Moree Loop 3, Winter Springs, FL
Christine Landrau · MARK SPAIN REAL ESTATE
Price Reduced33Active
$301,000
4 bd · 3 ba · 1,878 sqft
702 Glasgow Court, Winter Springs, FL
Carrie Sue Shawfield · SHAWFIELD REALTY GROUP
Price Reduced35Active
$272,500
3 bd · 2 ba · 1,460 sqft
476 Club Drive, Winter Springs, FL
Jeff Singletary · KELLER WILLIAMS HERITAGE REALTY
Price Reduced25Active
$210,000
2 bd · 2 ba · 1,224 sqft
499 Club Drive, Winter Springs, FL
Paul Buscemi · FLORIDA HOME TEAM REALTY LLC
Price Reduced43Active
$269,000
3 bd · 2 ba · 1,460 sqft
446 Club Drive, Winter Springs, FL
Hanoi Burgos · COLDWELL BANKER RESIDENTIAL RE
Price Reduced33Active
$215,000
2 bd · 2 ba · 1,002 sqft
506 Club Drive, Winter Springs, FL
Kathleen Harrison · CALL IT CLOSED INTL REALTY

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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Listing data & MLS disclosures

Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.