Trailmark Homes For Sale

Searching for Trailmark homes for sale in St. Augustine, FL. If you’re interested in any of the Trailmark home listings that you see below, just click the "Ask a Question" button when viewing the details of that property. Our St. Augustine real estate team is able to provide you with disclosures, past sales history, dates and prices of homes recently sold nearby, and other details related to the Trailmark home market.

And if you're interested in Trailmark homes for sale, we also invite you to register for a free account so that you can receive email alerts whenever new Trailmark St. Augustine homes hit the market, allowing you to stay one-step ahead of other buyers in the area. And remember to call or text us directly with any additional questions you have about buying or selling a home in St. Augustine, Florida. 

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New Pending
243 Bluegrass Way, St. Augustine

$409,990

243 Bluegrass Way, St. Augustine

3 Beds 2 Baths 1,864 SqFt Residential MLS® # 2144954
52 Crosswood Court, St. Augustine

$775,000

52 Crosswood Court, St. Augustine

5 Beds 4 Baths 3,531 SqFt Residential MLS® # 2162665
Under Contract
105 Bloomfield Way, St. Augustine

$474,900

105 Bloomfield Way, St. Augustine

4 Beds 4 Baths 2,270 SqFt Residential MLS® # 2161778
Open House
775 Farmfield Drive, St. Augustine

$399,990

775 Farmfield Drive, St. Augustine

3 Beds 2 Baths 1,622 SqFt Residential
Fri, Sep 11th, 2026 @ 1pm - 5pm
MLS® # 2161699
Open House
782 Farmfield Drive, St. Augustine

$469,990

782 Farmfield Drive, St. Augustine

4 Beds 3 Baths 2,190 SqFt Residential
Fri, Sep 11th, 2026 @ 1pm - 5pm
MLS® # 2161691
Open House
643 Farmfield Drive, St. Augustine

$479,990

643 Farmfield Drive, St. Augustine

3 Beds 3 Baths 2,316 SqFt Residential
Fri, Sep 11th, 2026 @ 1pm - 5pm
MLS® # 2161681
Under Contract
98 Ferndale Way, St. Augustine

$419,900

98 Ferndale Way, St. Augustine

3 Beds 2 Baths 1,893 SqFt Residential MLS® # 2160318
75 Crossfield Place, St. Augustine

$1,054,000

↓ $25,000

75 Crossfield Place, St. Augustine

5 Beds 5 Baths 3,648 SqFt Residential MLS® # 2160062
Pending
107 Providence Drive, St. Augustine

$524,900

107 Providence Drive, St. Augustine

4 Beds 3 Baths 2,325 SqFt Residential MLS® # 2160023
Under Contract
255 Split Oak Road, St. Augustine

$638,000

255 Split Oak Road, St. Augustine

4 Beds 4 Baths 2,800 SqFt Residential MLS® # 2157575
Under Contract
785 Back Creek Drive, St. Augustine

$949,900

785 Back Creek Drive, St. Augustine

4 Beds 3 Baths 2,936 SqFt Residential MLS® # 2156969
289 Weathered Edge Drive, St. Augustine

$575,000

↓ $14,900

289 Weathered Edge Drive, St. Augustine

4 Beds 3 Baths 2,491 SqFt Residential MLS® # 2153167
Open House
722 Farmfield Drive, St. Augustine

$439,990

↑ $40,000

722 Farmfield Drive, St. Augustine

4 Beds 3 Baths 1,968 SqFt Residential
Fri, Sep 11th, 2026 @ 1pm - 5pm
MLS® # 2152008
Open House
760 Farmfield Drive, St. Augustine

$479,990

760 Farmfield Drive, St. Augustine

4 Beds 3 Baths 1,968 SqFt Residential
Fri, Sep 11th, 2026 @ 1pm - 5pm
MLS® # 2152007
Open House
754 Farmfield Drive, St. Augustine

$499,990

↑ $35,000

754 Farmfield Drive, St. Augustine

4 Beds 3 Baths 2,190 SqFt Residential
Fri, Sep 11th, 2026 @ 1pm - 5pm
MLS® # 2152006
Pending
530 Farmfield Drive, St. Augustine

$395,382

530 Farmfield Drive, St. Augustine

3 Beds 2 Baths 1,622 SqFt Residential MLS® # 2152002
Under Contract
165 Bluegrass Way, St. Augustine

$469,999

↓ $5,000

165 Bluegrass Way, St. Augustine

4 Beds 3 Baths 2,503 SqFt Residential MLS® # 2150834
210 Wineberry Lane, St. Augustine

$404,990

↓ $3,000

210 Wineberry Lane, St. Augustine

3 Beds 3 Baths 2,048 SqFt Residential MLS® # 2149430
520 Back Creek Drive, St. Augustine

$835,000

520 Back Creek Drive, St. Augustine

5 Beds 3 Baths 3,516 SqFt Residential MLS® # 2113803
522 White Rabbit Run, St. Augustine

$476,997

↑ $12,000

522 White Rabbit Run, St. Augustine

3 Beds 3 Baths 2,414 SqFt Residential MLS® # 2098835
184 Wineberry Lane, St. Johns

$389,000

↓ $10,000

184 Wineberry Lane, St. Johns

3 Beds 2 Baths 1,864 SqFt Residential MLS® # 2149567

Trailmark Community Current Market Data

Trailmark Community housing market statistics: As of September 8, 2026 there are currently 36 properties for sale in Trailmark Community, with an average asking price of $518,708. The highest-priced property is $1,054,000 and the lowest-priced property can be purchased for $389,000. Trailmark Community listings have an average price of $225 per square feet, based on listings with 4 beds, 3 baths, and 2,289 square feet of living space.