About The Highlands
Market Summary
Avg. List Price
Current Listings
Avg. Active Days on Market
Currently no active listings available that meet the criteria for market statistics calculations.
What Locals Say
Civic engagement
Healthy foods
Hard working
Luxury culture
Vehicle enthusiasts
Movie goers
Shopping
Homey & Leisurely
Into gardening
Fitness oriented
market snapshot
We’ve gathered the latest market data to help you better understand what’s happening in The Highlands.
active listings
Currently no active listings available that meet the criteria for market statistics calculations.
Recently Sold
Recently Sold Avg.
Avg. Days on Market
Recently Sold
Avg. Price/Area
Properties in The Highlands
All
Sold
New - 566 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
509 OSPREY LANE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: CENTURY 21 MCBRIDE REALTY GROUP, 386-866-1007, Tricia Daigle
Sold
New - 1,433 Hours
Open House
Price Drop
(Just Now)
View listing to see more images.
••••••
2 bd
2 ba
10 MOREE LOOP #1, WINTER SPRINGS, FL 32708
Listing Courtesy Of: ATIDOT INVESTMENT, LLC, Carla Morales
Sold
New - 134 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
429 SHEOAH BOULEVARD #3, WINTER SPRINGS, FL 32708
Listing Courtesy Of: COMPASS FLORIDA LLC, Marielle Parra
Sold
New - 161 Hours
Open House
View listing to see more images.
••••••
2 bd
3 ba
533 MOREE LOOP, WINTER SPRINGS, FL 32708
Listing Courtesy Of: HOMEVEST REALTY, 407-897-5400, Brad Young
Sold
New - 445 Hours
Open House
Price Drop
(1d)
View listing to see more images.
••••••
3 bd
3 ba
811 GATEHOUSE DRIVE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: LOVELAND PROPERTIES, 407-352-8118, Cleve Loveland
Sold
New - 830 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
425 SHEOAH BOULEVARD #29, WINTER SPRINGS, FL 32708
Listing Courtesy Of: KELLER WILLIAMS HERITAGE REALTY, 407-862-9700, David Miller
Sold
New - 715 Hours
Open House
View listing to see more images.
••••••
6 bd
4 ba
218 PERTH COURT #A, WINTER SPRINGS, FL 32708
Listing Courtesy Of: HOUSE HUNTING IN FLORIDA LLC, Jacqueline Chung
Sold
New - 1,050 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
230 MOREE LOOP #4, WINTER SPRINGS, FL 32708
Listing Courtesy Of: WEMERT GROUP REALTY LLC, 407-214-3967, Jenny Wemert
Sold
New - 765 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
629 NIGHTHAWK CIRCLE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: B & D FLORIDA REALTY, LLC, Brian Emmans
Sold
New - 2,319 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
10 MOREE LOOP #13, WINTER SPRINGS, FL 32708
Listing Courtesy Of: PAINE-ANDERSON PROPERTIES, INC, 407-695-7898, Joyce Gary
Sold
New - 282 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
450 DEWARS COURT, WINTER SPRINGS, FL 32708
Listing Courtesy Of: CHARISMA REALTY CORP, 321-430-7887, Charisma Marin
Sold
New - 2,996 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
411 SHEOAH BOULEVARD #37, WINTER SPRINGS, FL 32708
Listing Courtesy Of: CENTRAL FLORIDA REALTY MANAGEMENT LLC, 407-542-4403, Kevan Patel
Sold
New - 2,132 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
270 MOREE LOOP #5, WINTER SPRINGS, FL 32708
Listing Courtesy Of: OLYMPUS EXECUTIVE REALTY INC, 407-469-0090, Andre Hernandez
Sold
New - 677 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
621 DARON COURT, WINTER SPRINGS, FL 32708
Listing Courtesy Of: VENTURE HOME REALTY, 407-587-0076, Sheryl Webster
Sold
New - 2,363 Hours
Open House
View listing to see more images.
••••••
4 bd
3 ba
668 NIGHTHAWK CIRCLE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: AVENEW REALTY CORP, Desiree Rodriguez Silva
Sold
New - 4,963 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
40 SHEOAH BOULEVARD #28, WINTER SPRINGS, FL 32708
Listing Courtesy Of: DALTON WADE INC, 888-668-8283, Stephen Murphy
Sold
New - 1,470 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
701 GLASGOW COURT #701, WINTER SPRINGS, FL 32708
Listing Courtesy Of: CALL IT CLOSED INTL REALTY, 407-338-3339, Amy Phillips
Sold
New - 3,350 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
240 MOREE LOOP #2, WINTER SPRINGS, FL 32708
Listing Courtesy Of: PAINE-ANDERSON PROPERTIES, INC, 407-695-7898, Joyce Gary
Sold
New - 1,285 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
421 SHEOAH BOULEVARD #5, WINTER SPRINGS, FL 32708
Listing Courtesy Of: EXP REALTY LLC, 888-883-8509, Sascha Davis
Sold
New - 3,734 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
50 SHEOAH BOULEVARD #34, WINTER SPRINGS, FL 32708
Listing Courtesy Of: PAINE-ANDERSON PROPERTIES, INC, 407-695-7898, Joyce Gary
Log In / Sign Up
Log in or sign up for a Keller Williams account today and gain access to exclusive content and additional support from a local Keller Williams® agent!
Active
Sold
New - 566 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
509 OSPREY LANE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: CENTURY 21 MCBRIDE REALTY GROUP, 386-866-1007, Tricia Daigle
Sold
New - 1,433 Hours
Open House
Price Drop
(Just Now)
View listing to see more images.
••••••
2 bd
2 ba
10 MOREE LOOP #1, WINTER SPRINGS, FL 32708
Listing Courtesy Of: ATIDOT INVESTMENT, LLC, Carla Morales
Sold
New - 161 Hours
Open House
View listing to see more images.
••••••
2 bd
3 ba
533 MOREE LOOP, WINTER SPRINGS, FL 32708
Listing Courtesy Of: HOMEVEST REALTY, 407-897-5400, Brad Young
Sold
New - 445 Hours
Open House
Price Drop
(1d)
View listing to see more images.
••••••
3 bd
3 ba
811 GATEHOUSE DRIVE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: LOVELAND PROPERTIES, 407-352-8118, Cleve Loveland
Sold
New - 830 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
425 SHEOAH BOULEVARD #29, WINTER SPRINGS, FL 32708
Listing Courtesy Of: KELLER WILLIAMS HERITAGE REALTY, 407-862-9700, David Miller
Sold
New - 1,050 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
230 MOREE LOOP #4, WINTER SPRINGS, FL 32708
Listing Courtesy Of: WEMERT GROUP REALTY LLC, 407-214-3967, Jenny Wemert
Sold
New - 2,319 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
10 MOREE LOOP #13, WINTER SPRINGS, FL 32708
Listing Courtesy Of: PAINE-ANDERSON PROPERTIES, INC, 407-695-7898, Joyce Gary
Sold
New - 2,363 Hours
Open House
View listing to see more images.
••••••
4 bd
3 ba
668 NIGHTHAWK CIRCLE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: AVENEW REALTY CORP, Desiree Rodriguez Silva
Sold
New - 4,963 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
40 SHEOAH BOULEVARD #28, WINTER SPRINGS, FL 32708
Listing Courtesy Of: DALTON WADE INC, 888-668-8283, Stephen Murphy
Sold
New - 3,350 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
240 MOREE LOOP #2, WINTER SPRINGS, FL 32708
Listing Courtesy Of: PAINE-ANDERSON PROPERTIES, INC, 407-695-7898, Joyce Gary
Sold
New - 1,285 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
421 SHEOAH BOULEVARD #5, WINTER SPRINGS, FL 32708
Listing Courtesy Of: EXP REALTY LLC, 888-883-8509, Sascha Davis
Sold
New - 3,734 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
50 SHEOAH BOULEVARD #34, WINTER SPRINGS, FL 32708
Listing Courtesy Of: PAINE-ANDERSON PROPERTIES, INC, 407-695-7898, Joyce Gary
Sold
New - 286 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
429 SHEOAH BOULEVARD #8, WINTER SPRINGS, FL 32708
Listing Courtesy Of: UPZEL REALTY LLC, 407-430-2529, Elizabeth Dowell
Sold
New - 1,097 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
426 CLUB DRIVE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: PAINE-ANDERSON PROPERTIES, INC, 407-695-7898, Joyce Gary
Sold
New - 1,335 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
90 MOREE LOOP #15, WINTER SPRINGS, FL 32708
Listing Courtesy Of: FOLIO REALTY LLC, 407-352-4020, Preston McGann PA
Sold
New - 1,116 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
466 CLUB DRIVE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: LATIN CONNECTION REALTY GROUP, 407-344-5510, Claudia Martinez
Sold
New - 1,126 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
605 MARNI DRIVE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: RE/MAX TOWN CENTRE, 407-996-3200, Maria Shreve
Sold
New - 1,790 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
440 MACGREGOR RD, WINTER SPRINGS, FL 32708
Listing Courtesy Of: LA ROSA REALTY LLC, 321-939-3748, Tiffany Polite
Log In / Sign Up
Log in or sign up for a Keller Williams account today and gain access to exclusive content and additional support from a local Keller Williams® agent!
Pending
Sold
New - 134 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
429 SHEOAH BOULEVARD #3, WINTER SPRINGS, FL 32708
Listing Courtesy Of: COMPASS FLORIDA LLC, Marielle Parra
Sold
New - 715 Hours
Open House
View listing to see more images.
••••••
6 bd
4 ba
218 PERTH COURT #A, WINTER SPRINGS, FL 32708
Listing Courtesy Of: HOUSE HUNTING IN FLORIDA LLC, Jacqueline Chung
Sold
New - 765 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
629 NIGHTHAWK CIRCLE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: B & D FLORIDA REALTY, LLC, Brian Emmans
Sold
New - 282 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
450 DEWARS COURT, WINTER SPRINGS, FL 32708
Listing Courtesy Of: CHARISMA REALTY CORP, 321-430-7887, Charisma Marin
Sold
New - 2,996 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
411 SHEOAH BOULEVARD #37, WINTER SPRINGS, FL 32708
Listing Courtesy Of: CENTRAL FLORIDA REALTY MANAGEMENT LLC, 407-542-4403, Kevan Patel
Sold
New - 2,132 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
270 MOREE LOOP #5, WINTER SPRINGS, FL 32708
Listing Courtesy Of: OLYMPUS EXECUTIVE REALTY INC, 407-469-0090, Andre Hernandez
Sold
New - 677 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
621 DARON COURT, WINTER SPRINGS, FL 32708
Listing Courtesy Of: VENTURE HOME REALTY, 407-587-0076, Sheryl Webster
Sold
New - 1,470 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
701 GLASGOW COURT #701, WINTER SPRINGS, FL 32708
Listing Courtesy Of: CALL IT CLOSED INTL REALTY, 407-338-3339, Amy Phillips
Sold
New - 1,121 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
302 BRIDIE COURT, WINTER SPRINGS, FL 32708
Listing Courtesy Of: RE/MAX TOWN & COUNTRY REALTY, 407-695-2066, Dominick Florio
Sold
New - 1,280 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
40 MOREE LOOP #1, WINTER SPRINGS, FL 32708
Listing Courtesy Of: OLYMPUS EXECUTIVE REALTY INC, 407-469-0090, Andre Hernandez
Sold
New - 519 Hours
Open House
View listing to see more images.
••••••
3 bd
3 ba
509 SHANE CIRCLE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: COMPASS FLORIDA LLC, Jane Peterson
Log In / Sign Up
Log in or sign up for a Keller Williams account today and gain access to exclusive content and additional support from a local Keller Williams® agent!
Upcoming Open Houses
Log In / Sign Up
Log in or sign up for a Keller Williams account today and gain access to exclusive content and additional support from a local Keller Williams® agent!
Recently Sold
Sold
- Mar 18, 2025
New - 1,626 Hours
Open House
View listing to see more images.
••••••
1 bd
1 ba
30 SHEOAH BOULEVARD #22, WINTER SPRINGS, FL 32708
Listing Courtesy Of: CENTRAL FLORIDA REALTY MANAGEMENT LLC, 407-542-4403, Kevan Patel
Sold
- Mar 11, 2025
New - 484,163 Hours
Open House
View listing to see more images.
••••••
2 bd
2 ba
10 SHEOAH BOULEVARD #4, WINTER SPRINGS, FL 32708
Listing Courtesy Of: HD REALTY LLC, 407-260-8800, Nicole Anderson
Sold
- Feb 21, 2025
New - 1,685 Hours
Open House
View listing to see more images.
••••••
1 bd
1 ba
30 SHEOAH BLVD #18, WINTER SPRINGS, FL 32708
Listing Courtesy Of: INFINITY REAL ESTATE GROUP, 407-760-0835, Tamara Martin
Sold
- Feb 20, 2025
New - 1,685 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
717 GLASGOW COURT, WINTER SPRINGS, FL 32708
Listing Courtesy Of: GECKO REALTY, INC, 407-929-0264, Travis Lewis
Sold
- Feb 13, 2025
New - 2,353 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
314 MACGREGOR ROAD, WINTER SPRINGS, FL 32708
Listing Courtesy Of: PROPERTIES IN TOWN, 321-231-9843, Javier Paredes
Sold
- Feb 10, 2025
New - 2,289 Hours
Open House
View listing to see more images.
••••••
4 bd
2 ba
611 HUNTLY LANE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: INVESTOR'S REAL ESTATE LLC, 407-688-4355, Sarah Jones Jones
Sold
- Feb 4, 2025
New - 2,848 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
639 MARNI DRIVE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: MODERN WORLD REALTY LLC, 305-903-9158, Carla Cabrera
Sold
- Feb 3, 2025
New - 5,216 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
766 BLADES COURT, WINTER SPRINGS, FL 32708
Listing Courtesy Of: LOKATION, 954-545-5583, Gregory Buckley
Sold
- Jan 29, 2025
New - 2,224 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
615 NIGHTHAWK CIRCLE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: EXP REALTY LLC, 888-883-8509, Joshua Tirado
Sold
- Jan 29, 2025
New - 3,466 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
429 SHEOAH BOULEVARD #2, WINTER SPRINGS, FL 32708
Listing Courtesy Of: COMPASS FLORIDA LLC, Marielle Parra
Sold
- Jan 28, 2025
New - 4,317 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
817 DUNDEE DRIVE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: THE WILKINS WAY LLC, 407-874-0230, William Wygle
Sold
- Jan 28, 2025
New - 1,953 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
870 FALKIRK DRIVE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: LPT REALTY, 877-366-2213, Gea Gomez
Sold
- Jan 21, 2025
New - 3,907 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
718 GLASGOW COURT #718, WINTER SPRINGS, FL 32708
Listing Courtesy Of: KELLER WILLIAMS ADVANTAGE REALTY, 407-977-7600, Nicholas Kovats
Sold
- Jan 13, 2025
New - 3,547 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
423 SHEOAH BOULEVARD #11, WINTER SPRINGS, FL 32708
Listing Courtesy Of: PAINE-ANDERSON PROPERTIES, INC, 407-695-7898, Joyce Gary
Sold
- Dec 27, 2024
New - 5,671 Hours
Open House
View listing to see more images.
••••••
3 bd
2 ba
502 OSPREY LANE, WINTER SPRINGS, FL 32708
Listing Courtesy Of: LPT REALTY, LLC, 877-366-2213, Debra Hutto
Log In / Sign Up
Log in or sign up for a Keller Williams account today and gain access to exclusive content and additional support from a local Keller Williams® agent!
Nearby Schools
Public
Private
No data to show right now.
N/A
Grade
Student-Teacher Ratio:
No data to show right now.
No data to show right now.
N/A
Grade
Student-Teacher Ratio:
No data to show right now.
Disclaimer: This information is provided by
Precisely
and subject to change.
Please check the applicable school district.
Transit & Commute
Estimated commute times from The Highlands
Car-Dependent
Walkable
Very Walkable
Nearby Neighborhoods
Hidden Oak
3
Current Listings
Seville Chase
3
Current Listings
The Ranchlands
Osprey Landing
Longwood Hills/Lake Emma
Tiberon Cove
Woldunn
1
Current Listings
Legacy Park
4
Current Listings
Triplet Lake
2
Current Listings
Remington Oaks
Eagles Crossing
1
Current Listings
Lake Jesup Woods
1
Current Listings
Heritage Park Townhomes
2
Current Listings
Lake Mary Landings
4
Current Listings
Sanford
3
Current Listings
Longwood Park
1
Current Listings
Hensons Acres
Winding Hollow
1
Current Listings
Longwood Plantation
1
Current Listings
Cardinal Oaks Phase II
Lake Bingham/L Mary Woods
Columbus Harbor
1
Current Listings
Castlewood
1
Current Listings
Spicewood
Wynnwood
2
Current Listings
Jesups Reserve Townhomes
6
Current Listings
Lake Jessup
3
Current Listings
Ruskin Street
Osprey Pointe
Danbury Mill
Sandalwood
1
Current Listings
Crystal Bowl
13
Current Listings
Lucky Trail
1
Current Listings
Vienna Woods
2
Current Listings
Highland Hills
1
Current Listings
Meadow Brooke
Crossings Lakewood
6
Current Listings
Tuskawilla Trails
Lotus Ln
5
Current Listings
Banyan Pointe
Evansdale Estates
11
Current Listings
Crossings Silver Lakes East
1
Current Listings
The Landings
2
Current Listings
Lake Searcy Shores
2
Current Listings
Park Ave
Brentwood
The Springs
1
Current Listings
Casselberry Estates
North Orlando Terrace
Wayman St
1
Current Listings
Chelsea Place
Brookside
Sky Lark
2
Current Listings
Mosswood
Lake Kathryn
2
Current Listings
Candyland Park
3
Current Listings
Reserves at Lake Irene
Hacienda Village
Mt Greenwood
4
Current Listings
Hanover Place
2
Current Listings
Big Tree Park
Lake Glen Dr
1
Current Listings
Candyland
2
Current Listings
Moss Cove
6
Current Listings
Harbor Winds
2
Current Listings
Deersong
1
Current Listings
Williamson Heights
2
Current Listings
Edgemon
Seven Oaks
North Orlando Estates
8
Current Listings
Wyndham Woods/Wil O Wik
4
Current Listings
Autumn Chase
Wildmere Manor
5
Current Listings
Longwood Green
2
Current Listings
Parkstone
5
Current Listings
S Country Club Road
1
Current Listings
The Ranchlands
4
Current Listings
The Landings At Parkst
Hanover Point
2
Current Listings
Lake Kathren
Wildwood
1
Current Listings
Orange Ave
3
Current Listings
Stone Gable
1
Current Listings
Crystal Creek
2
Current Listings
Countryclub Heights
Longwood
2
Current Listings
Oak/E Jessup
Seminole Heights
Winding Oak
2
Current Listings
Silhouette Ct
3
Current Listings
Hampton Park
1
Current Listings