Watermark Homes Under $500K for Sale

Every home priced under $500K currently for sale in Watermark — pulled live from the Stellar MLS and updated continuously. Pair this with the free Watermark market report to see what's actually selling, days on market, and sold-to-list ratios before you make an offer.

Watermark Market ReportCall 321.373.3536

8 Homes Under $500K in Watermark

9766 Amber Chestnut Way, FL9766 Amber Chestnut Way, FL
Stellar MLS
ActiveTownhouse360°

$429,900

9766 Amber Chestnut Way

Winter Garden, FL 34787

3 bd · 3 ba · 1,937 sqft

Watermark Ph 3

MLS ID #L4965505, LPT REALTY, LLC.

Listing provided by Stellar MLS

9231 Grand Island Way, FL9231 Grand Island Way, FL
Stellar MLS
ActiveSingle Family Residence360°

$449,000

9231 Grand Island Way

Winter Garden, FL 34787

4 bd · 3 ba · 2,060 sqft

Watermark Phase 2c

MLS ID #O6405710, ELITE INTERNATIONAL REALTY INC.

Listing provided by Stellar MLS

14031 Picard Aly, FL14031 Picard Aly, FL
Stellar MLS
ActiveTownhouse360°

$349,000

14031 Picard Aly

Winter Garden, FL 34787

3 bd · 3 ba · 1,789 sqft

Watermark Ph 3

MLS ID #O6421215, ELITE INTERNATIONAL REALTY INC.

Listing provided by Stellar MLS

9469 Meadow Hunt Way, FL9469 Meadow Hunt Way, FL
Stellar MLS
ActiveSingle Family Residence360°

$475,000

9469 Meadow Hunt Way

Winter Garden, FL 34787

4 bd · 3 ba · 1,868 sqft

Watermark At Horizon West

MLS ID #O6449072, HANG SENG REALTY , INC.

Listing provided by Stellar MLS

9936 Pallida Hickory Way, FL9936 Pallida Hickory Way, FL
Stellar MLS
ActiveSingle Family Residence360°

$468,000

9936 Pallida Hickory Way

Winter Garden, FL 34787

3 bd · 3 ba · 1,744 sqft

Watermark

MLS ID #O6447966, RC GROUP REALTY LLC.

Listing provided by Stellar MLS

14543 Golden Harbor Ln, FL14543 Golden Harbor Ln, FL
Stellar MLS
ActiveSingle Family Residence360°

$485,000

14543 Golden Harbor Ln

Winter Garden, FL 34787

3 bd · 3 ba · 2,039 sqft

Watermark

MLS ID #O6433451, PREFERRED REAL ESTATE BROKERS.

Listing provided by Stellar MLS

9356 Tyrella Pine Trl, FL9356 Tyrella Pine Trl, FL
Stellar MLS
ActiveSingle Family Residence360°

$495,000

9356 Tyrella Pine Trl

Winter Garden, FL 34787

4 bd · 3 ba · 1,838 sqft

Watermark Ph 2b

MLS ID #O6446296, POINTON REALTY INC.

Listing provided by Stellar MLS

9362 Woodcrane Dr, FL9362 Woodcrane Dr, FL
Stellar MLS
ActiveSingle Family Residence360°

$435,800

9362 Woodcrane Dr

Winter Garden, FL 34787

3 bd · 3 ba · 2,058 sqft

Watermark Ph 1b

MLS ID #O6417277, CENTURY 21 CARIOTI.

Listing provided by Stellar MLS

More Watermark Homes for Sale

MLS GRID

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 3:32 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