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

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32 listings

Homes for Sale in Highlands, Winter Springs, FL

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24 of 32 Listings

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24 of 32 Listings

38Active
$500,000
3 bd · 2 ba · 2,181 sqft
615 Anhinga Road, Winter Springs, FL
Steven Koleno · BEYCOME OF FLORIDA LLC
38Active
$500,000
3 bd · 2 ba · 2,181 sqft
615 Anhinga Rd, Winter Springs, FL
Steven Koleno · BEYCOME OF FLORIDA LLC
21Active
$170,000
2 bd · 2 ba · 936 sqft
417 Sheoah Blvd #17, Winter Springs, FL
Valerie Casals · INVESTOR'S REAL ESTATE LLC
21Active
$170,000
2 bd · 2 ba · 936 sqft
417 Sheoah Boulevard 17, Winter Springs, FL
Valerie Casals · INVESTOR'S REAL ESTATE LLC
Price Reduced42Active
$374,400
3 bd · 3 ba · 1,583 sqft
662 Nighthawk Circle, Winter Springs, FL
Carla Cabrera · MODERN WORLD REALTY LLC
Price Reduced42Active
$374,400
3 bd · 3 ba · 1,583 sqft
662 Nighthawk Cir, Winter Springs, FL
Carla Cabrera · MODERN WORLD REALTY LLC
49Active
$350,000
2 bd · 2 ba · 1,502 sqft
321 Kirkcaldy Drive, Winter Springs, FL
Emily Halpern · COLDWELL BANKER REALTY
49Active
$350,000
2 bd · 2 ba · 1,502 sqft
321 Kirkcaldy Dr, Winter Springs, FL
Emily Halpern · COLDWELL BANKER REALTY
16Active
$329,000
3 bd · 3 ba · 1,680 sqft
472 Harbor Winds Ct, Winter Springs, FL
Robert Arnold, Jr · SAND DOLLAR REALTY GROUP INC
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 Reduced63Active
$390,000
4 bd · 3 ba · 2,150 sqft
758 N Gretna Court, Winter Springs, FL
Nicholas Kovats · KELLER WILLIAMS ADVANTAGE REALTY
Price Reduced63Active
$390,000
4 bd · 3 ba · 2,150 sqft
758 N Gretna Ct, 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 Reduced29Active
$140,000
1 bd · 1 ba · 710 sqft
220 Moree Loop 2, Winter Springs, FL
Patricia Woodhouse · RE/MAX CENTRAL REALTY
Price Reduced26Active
$344,000
3 bd · 3 ba · 1,792 sqft
830 Dunbar Terrace, Winter Springs, FL
Karen Albright · OPENDOOR BROKERAGE LLC
Price Reduced26Active
$344,000
3 bd · 3 ba · 1,792 sqft
830 Dunbar Ter, 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
41Active
$199,000
3 bd · 2 ba · 1,187 sqft
429 Sheoah Blvd #9, Winter Springs, FL
Freddy Escobar · LPT REALTY, LLC
Price Reduced50Active
$324,900
3 bd · 2 ba · 1,178 sqft
335 Kirkcaldy Drive, Winter Springs, FL
Irina Carp · MILLENIUM REALTY GROUP
Price Reduced50Active
$324,900
3 bd · 2 ba · 1,178 sqft
335 Kirkcaldy Dr, Winter Springs, FL
Irina Carp · MILLENIUM REALTY GROUP
Price Reduced38Active
$167,777
2 bd · 2 ba · 972 sqft
50 Sheoah Boulevard 33, Winter Springs, FL
Fanny Stollmeyer · LIFESTYLE INTERNATIONAL REALTY
Price Reduced38Active
$167,777
2 bd · 2 ba · 972 sqft
50 Sheoah Blvd #33, Winter Springs, FL
Fanny Stollmeyer · LIFESTYLE INTERNATIONAL REALTY
Price Reduced24Active
$170,000
3 bd · 2 ba · 1,187 sqft
240 Moree Loop 3, Winter Springs, FL
Christine Landrau · MARK SPAIN REAL ESTATE
Price Reduced24Active
$170,000
3 bd · 2 ba · 1,187 sqft
240 Moree Loop #3, Winter Springs, FL
Christine Landrau · MARK SPAIN REAL ESTATE

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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.

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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.

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.