Highland Lakes Homes Under $500K for Sale
Every home priced under $500K currently for sale in Highland Lakes — pulled live from the Stellar MLS and updated continuously. Pair this with the free Highland Lakes market report to see what's actually selling, days on market, and sold-to-list ratios before you make an offer.
24+ Homes Under $500K in Highland Lakes
$69,900
500 Newell Hill Rd #105b
Leesburg, FL 34748
2 bd · 2 ba · 1,134 sqft
Leesburg Chesterbrook 02 Condo Ph 01
MLS ID #G5118125, SUNBELT HOME REALTY, INC..
Listing provided by Stellar MLS
$320,000
5901 Candle Glow Pl
Leesburg, FL 34748
3 bd · 2 ba · 1,978 sqft
Legacy Of Leesburg
MLS ID #G5114312, PREMIER SOTHEBYS INT'L REALTY.
Listing provided by Stellar MLS
$349,000
5418 Barnwell Ct
Leesburg, FL 34748
2 bd · 3 ba · 2,188 sqft
Plantation At Leesburg Riverside Village
MLS ID #G5118405, BHHS FLORIDA REALTY.
Listing provided by Stellar MLS
$249,900
911 Grand Vista Trl
Leesburg, FL 34748
2 bd · 2 ba · 1,571 sqft
Pennbrooke Phase 1k Unit Iii Lot K187 Pb 40 Pgs 46
MLS ID #G5118392, RIGHT REALTY CONNECTION, INC..
Listing provided by Stellar MLS
$357,000
7733 Sloewood Dr
Leesburg, FL 34748
4 bd · 3 ba · 2,106 sqft
Park Hill Ph 02
MLS ID #G5114319, ALDEN REALTY LLC.
Listing provided by Stellar MLS
$160,000
902 Talladega St
Leesburg, FL 34748
3 bd · 1 ba · 966 sqft
Liberia
MLS ID #G5118080, ERA GRIZZARD REAL ESTATE.
Listing provided by Stellar MLS
$120,000
407 Palo Verde Dr
Leesburg, FL 34748
2 bd · 2 ba · 1,342 sqft
Hawthorne At Leesburg A Coop
MLS ID #R4910498, BLACK TIE REALTY, INC..
Listing provided by Stellar MLS
$229,500
25300 Hibiscus St
Leesburg, FL 34748
2 bd · 2 ba · 1,908 sqft
Plantation At Leesburg Greentree
MLS ID #TB8460495, HOMECOIN.COM.
Listing provided by Stellar MLS
$275,500
27001 White Plains Way
Leesburg, FL 34748
2 bd · 2 ba · 1,330 sqft
Leesburg Arlington Ridge Ph 1-C
MLS ID #G5117541, MORRIS REALTY AND INVESTMENTS.
Listing provided by Stellar MLS
$325,000
5336 Tidewater St
Leesburg, FL 34748
2 bd · 2 ba · 1,918 sqft
Plantation At Leesburg Riverside Village Lt
MLS ID #G5118569, DORAN REAL ESTATE COMPANY.
Listing provided by Stellar MLS
$299,999
925 Beverly Harbors Dr
Leesburg, FL 34748
3 bd · 2 ba · 1,842 sqft
Leesburg Beverly Harbors 02 Condo
MLS ID #G5115102, LPT REALTY, LLC.
Listing provided by Stellar MLS
$364,900
27118 Roanoke Dr
Leesburg, FL 34748
3 bd · 2 ba · 1,713 sqft
Arlington Ridge
MLS ID #G5110376, HARRISON REAL PROPERTY GROUP.
Listing provided by Stellar MLS
$449,000
4632 Nottoway
Leesburg, FL 34748
3 bd · 3 ba · 2,816 sqft
Plantation At Leesburg Nottoway Village
MLS ID #G5115838, CENTURY 21 MYERS ROSE REALTY.
Listing provided by Stellar MLS
$255,000
198 Jacaranda Dr
Leesburg, FL 34748
2 bd · 2 ba · 1,392 sqft
Hawthorne At Leesburg A Coop
MLS ID #G5118541, HAWTHORNE RESIDENTS COOPERATIVE ASSOCIATION INC..
Listing provided by Stellar MLS
$349,900
5729 King James Ave
Leesburg, FL 34748
3 bd · 3 ba · 2,402 sqft
Royal Highlands Ph 01b
MLS ID #TB8488786, HOMECOIN.COM.
Listing provided by Stellar MLS
$310,000
5322 Pond Crossing Pl
Leesburg, FL 34748
3 bd · 2 ba · 1,655 sqft
Legacy Leesburg Unit 06
MLS ID #G5117311, FLORIDA PLUS REALTY, LLC.
Listing provided by Stellar MLS
$222,900
509 Scenic St
Leesburg, FL 34748
3 bd · 2 ba · 1,632 sqft
Leesburg Stoer Island Add 01
MLS ID #O6437308, MAINSTAY BROKERAGE LLC.
Listing provided by Stellar MLS
$289,990
6712 Cedar Landing Cir
Leesburg, FL 34748
3 bd · 3 ba · 1,787 sqft
Cedar Landings Townhomes
MLS ID #W7888269, MALTBIE REALTY GROUP.
Listing provided by Stellar MLS
$289,990
6692 Cedar Landing Cir
Leesburg, FL 34748
3 bd · 3 ba · 1,787 sqft
Cedar Landings Townhomes
MLS ID #W7886881, MALTBIE REALTY GROUP.
Listing provided by Stellar MLS
$355,670
6374 Cedar Landing Cir
Leesburg, FL 34748
3 bd · 2 ba · 1,590 sqft
Cedar Landings
MLS ID #W7889607, MALTBIE REALTY GROUP.
Listing provided by Stellar MLS
$299,000
7238 Hillcrest St
Leesburg, FL 34748
4 bd · 2 ba · 1,903 sqft
Shady Dells
MLS ID #O6426650, MARK SPAIN REAL ESTATE.
Listing provided by Stellar MLS
$249,000
21212 Royal St Georges Ln
Leesburg, FL 34748
2 bd · 2 ba · 1,299 sqft
Royal Highlands Ph 01ca
MLS ID #O6443197, WEMERT GROUP REALTY LLC.
Listing provided by Stellar MLS
$385,170
22181 Pine Grove Loop
Leesburg, FL 34748
3 bd · 3 ba · 2,081 sqft
Cedar Landings
MLS ID #W7889257, MALTBIE REALTY GROUP.
Listing provided by Stellar MLS
$333,990
6378 Cedar Landing Cir
Leesburg, FL 34748
3 bd · 2 ba · 1,590 sqft
Cedar Landings
MLS ID #W7888709, MALTBIE REALTY GROUP.
Listing provided by Stellar MLS
More Highland Lakes Homes for Sale
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of October 2, 2026 at 4:36 PM ET. 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.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA