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.

Highland Lakes Market ReportCall 321.373.3536

21 Homes Under $500K in Highland Lakes

ActiveSingle Family Residence360°

$329,000

5523 Rosewall Cir

Leesburg, FL 34748

3 bd · 3 ba · 2,283 sqft

Highland Lakes Ph 01

MLS ID #OM735143, LPT REALTY, LLC.

Listing provided by Stellar MLS

ActiveSingle Family Residence360°

$307,500

5606 Rosewall Cir

Leesburg, FL 34748

3 bd · 2 ba · 2,040 sqft

Highland Lakes Ph 01

MLS ID #G5116293, FLORIDA PLUS REALTY, LLC.

Listing provided by Stellar MLS

ActiveVilla360°

$229,900

5440 Rosewall Cir

Leesburg, FL 34748

2 bd · 2 ba · 1,210 sqft

Highland Lakes Ph 01

MLS ID #G5118163, VANGIE BERRY SIGNATURE REALTY.

Listing provided by Stellar MLS

ActiveSingle Family Residence360°

$240,000

26118 Newcombe Cir

Leesburg, FL 34748

2 bd · 2 ba · 2,216 sqft

Highland Lakes

MLS ID #O6454186, MARK SPAIN REAL ESTATE.

Listing provided by Stellar MLS

ActiveVilla360°

$219,000

26627 Racquet Cir

Leesburg, FL 34748

2 bd · 2 ba · 1,120 sqft

Highland Lakes Ph 02a

MLS ID #G5110237, BHHS FLORIDA REALTY.

Listing provided by Stellar MLS

ActiveVilla360°

$229,900

5546 Rosewall

Leesburg, FL 34748

2 bd · 2 ba · 1,120 sqft

Highland Lakes

MLS ID #G5119574, FLORIDA PLUS REALTY, LLC.

Listing provided by Stellar MLS

ActiveSingle Family Residence

$243,900

26233 Newcombe Cir

Leesburg, FL 34748

2 bd · 2 ba · 1,323 sqft

Highland Lakes Ph 01b

MLS ID #G5119344, COLDWELL BANKER REALTY.

Listing provided by Stellar MLS

ActiveSingle Family Residence360°

$329,900

26949 Racquet Cir

Leesburg, FL 34748

3 bd · 2 ba · 2,159 sqft

Highland Lakes Ph 03 Tr A-G

MLS ID #G5119396, COLDWELL BANKER REALTY.

Listing provided by Stellar MLS

ActiveSingle Family Residence360°

$269,000

26744 Racquet Cir

Leesburg, FL 34748

3 bd · 2 ba · 2,017 sqft

Highland Lakes

MLS ID #G5116861, FLORIDA PLUS REALTY, LLC.

Listing provided by Stellar MLS

ActiveVilla360°

$199,500

5536 Rosewall Cir

Leesburg, FL 34748

2 bd · 2 ba · 1,350 sqft

Highland Lakes Ph 01

MLS ID #G5116626, EXP REALTY LLC.

Listing provided by Stellar MLS

ActiveSingle Family Residence360°

$238,000

5622 Rosewall Cir

Leesburg, FL 34748

2 bd · 2 ba · 1,368 sqft

Highland Lakes Ph 01

MLS ID #G5117872, RE/MAX PREMIER REALTY.

Listing provided by Stellar MLS

ActiveSingle Family Residence360°

$232,000

5641 Laver St

Leesburg, FL 34748

2 bd · 2 ba · 1,060 sqft

Highland Lakes Ph 02a

MLS ID #G5118932, DOWN HOME REALTY, LLLP.

Listing provided by Stellar MLS

ActiveSingle Family Residence360°

$345,000

5606 Laver St

Leesburg, FL 34748

3 bd · 2 ba · 1,919 sqft

Highland Lakes Ph 2-A

MLS ID #G5117292, COLDWELL BANKER REALTY.

Listing provided by Stellar MLS

ActiveSingle Family Residence360°

$275,000

6523 Wilander St

Leesburg, FL 34748

3 bd · 2 ba · 1,545 sqft

Highland Lakes Sub

MLS ID #G5119002, CARLINO REAL ESTATE GROUP INC.

Listing provided by Stellar MLS

ActiveSingle Family Residence360°

$355,000

26912 Becker Ct

Leesburg, FL 34748

3 bd · 2 ba · 2,498 sqft

Highland Lakes Ph 02c

MLS ID #S5150365, PARTNERSHIP REALTY INC..

Listing provided by Stellar MLS

ActiveSingle Family Residence360°

$225,000

5500 Laver St

Leesburg, FL 34748

3 bd · 2 ba · 1,591 sqft

Highland Lakes Ph 02d Tr A-D

MLS ID #GC543618, EXP REALTY LLC.

Listing provided by Stellar MLS

ActiveSingle Family Residence

$219,900

5503 Laver St

Leesburg, FL 34748

2 bd · 2 ba · 1,332 sqft

Highland Lakes Ph 02d Tr A-D

MLS ID #G5112726, COLDWELL BANKER REALTY.

Listing provided by Stellar MLS

ActiveSingle Family Residence360°

$329,900

27138 Racquet Cir

Leesburg, FL 34748

3 bd · 2 ba · 2,025 sqft

Highland Lakes Ph 03 Tr A-G

MLS ID #G5117456, COLDWELL BANKER REALTY.

Listing provided by Stellar MLS

ActiveSingle Family Residence360°

$339,900

6631 Borg St

Leesburg, FL 34748

3 bd · 3 ba · 2,302 sqft

Highland Lakes Sub

MLS ID #G5117293, COLDWELL BANKER REALTY.

Listing provided by Stellar MLS

ActiveSingle Family Residence360°

$360,000

26245 Newcombe Cir

Leesburg, FL 34748

3 bd · 3 ba · 2,377 sqft

Highland Lakes Ph 01b

MLS ID #S5156558, GLOVEN REALTY.

Listing provided by Stellar MLS

ActiveSingle Family Residence360°

$325,000

27305 Racquet Cir

Leesburg, FL 34748

3 bd · 2 ba · 2,886 sqft

Highland Lakes Sub

MLS ID #O6423691, MARK SPAIN REAL ESTATE.

Listing provided by Stellar MLS

More Highland Lakes Homes for Sale

Homes $500K–$750K Homes $750K–$1M Pool Homes Full Highland Lakes Market Report →

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 November 5, 2026 at 6:48 AM 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