Homes for Sale $300K to $500K in St James City, FL

This page tracks every St James City listing with an asking price between $300,000 and $500,000, by community, with live counts and asking prices. Prices are asking prices from the MLS, not values, and the list changes with every refresh.

55 homes listed between $300,000 and $500,000 are for sale or pending in St James City, FL today across 19 communities. The median asking price is $369,900, from $300,000 to $499,000. Listings in St James City without that feature have a median of $559,900. Most listings right now: Cherry Estates (16), St James City (9), Gulfhaven (5). Updated October 2, 2026 from the MLS.

Live $300k–$500k homes in St. James City: the listings

52 active listings match today (52% of St. James City inventory), median asking $369,900, $289/sq ft, median 86 days on market. Photo cards link to the listing; refreshed nightly.

Newest $300k–$500k homes in St. James City

$499,000 New
2 bd · 2 ba · 1,152 sq ft · built 2024
2452 York Rd, 33956
Gulfhaven
Listing courtesy of Century 21 Sunbelt Realty
$374,900 New
2 bd · 2 ba · 960 sq ft · built 2024
2705 Patterson Ct, 33956
Gulf Haven
Listing courtesy of Century 21 Selling Paradise
$369,900 New
2 bd · 2 ba · 1,152 sq ft · built 2024
3076 Bowsprit Ln, 33956
Cherry Estates
Listing courtesy of Century 21 Selling Paradise
$365,000 New
2 bd · 2 ba · 1,400 sq ft · built 1987
3055 Harpoon Ln, 33956
Cherry Estates
Listing courtesy of Elite Edge Fl Realty
$325,900 New
2 bd · 2 ba · 1,053 sq ft · built 1981
2912 Oleander St B3, 33956
Fishermans Wharf Condo
Listing courtesy of Castaways Island Realty LLC
4507 Lake Heather Circle, $300k–$500k for sale in St. James City
$450,000 New
3 bd · 2 ba · 1,553 sq ft · built 2017
4507 Lake Heather Circle, 33956
Listing courtesy of THE KEYES COMPANY
$375,000 New
2 bd · 2 ba · 1,694 sq ft · built 1988
3121 Binnacle Ln, 33956
Cherry Estates
Listing courtesy of John R. Wood Properties
$300,000 New
2 bd · 2 ba · 872 sq ft · built 1973
3913 Dewberry Ln, 33956
Cherry Estates
Listing courtesy of LPT Realty, LLC
$399,000 New
2 bd · 3 ba · 1,014 sq ft · built 1991
2510 Rose Ave, 33956
Gulfhaven
Listing courtesy of John R. Wood Properties
$425,000
2 bd · 2 ba · 1,500 sq ft · built 1989
4472 Lake Heather Cir, 33956
Pine Island Village
Listing courtesy of Redfin Corporation
$325,000
3 bd · 2 ba · 1,288 sq ft · built 1974
3628 Tropical Point Dr, 33956
Pine Island Tropical Homesites
Listing courtesy of LPT Realty, LLC
$360,000
2 bd · 2 ba · 1,250 sq ft · built 2003
3064 Sloop Ln, 33956
Cherry Estates
Listing courtesy of Century 21 AllPoints Realty
$459,900
2 bd · 2 ba · 1,305 sq ft · built 2019
3400 Coquina Ln, 33956
St James City
Listing courtesy of Luxury Real Estate Group LLC
$350,000
2 bd · 2 ba · 1,387 sq ft · built 1987
3032 Bounty Ln, 33956
Cherry Estates
Listing courtesy of Compass Florida LLC
$339,000
3 bd · 3 ba · 1,753 sq ft · built 1972
3680 Mango St, 33956
Pine Island Tropical Homesites
Listing courtesy of Royal Shell Real Estate, Inc.
$320,000
2 bd · 2 ba · 1,726 sq ft · built 1995
3089 Skipper Ln, 33956
Cherry Estates
Listing courtesy of List In MLS Realty, LLC
$450,000
3 bd · 2 ba · 1,553 sq ft · built 2017
4507 Lake Heather Cir, 33956
Pine Island Village
Listing courtesy of The Keyes Company
$389,000
2 bd · 2 ba · 1,391 sq ft · built 2014
4826 Sandpiper Dr SW, 33956
Flamingo Bay
Listing courtesy of Realty One Group MVP
$380,000
4 bd · 2 ba · 1,527 sq ft · built 1973
3827 Coconut Dr, 33956
Trailerhaven
Listing courtesy of Realty 100
$300,000
3 bd · 2 ba · 1,917 sq ft · built 1990
8628 Yukon Ct, 33956
Kreamers Avocado
Listing courtesy of Marzucco Real Estate
$440,000
2 bd · 3 ba · 1,162 sq ft · built 2003
2551 Tamarind St, 33956
St James City
Listing courtesy of Century 21 Sunbelt Realty
$345,000
2 bd · 3 ba · 1,068 sq ft · built 1986
3660 Tropical Point Dr, 33956
Pine Island Tropical Homesites
Listing courtesy of Century 21 Sunbelt Realty
$320,000
2 bd · 2 ba · 960 sq ft · built 1975
3653 Dewberry Ln, 33956
Cherry Estates
Listing courtesy of John R. Wood Properties
3728 Gasparilla Street, $300k–$500k for sale in St. James City
$454,000
5 bd · 4 ba · 2,372 sq ft · built 1976
3728 Gasparilla Street, 33956
Listing courtesy of COLDWELL BANKER REALTY
$454,000
5 bd · 4 ba · 2,372 sq ft · built 1976
3728 Gasparilla St, 33956
Pine Island Tropical Homesites
Listing courtesy of Coldwell Banker Realty
$364,900
2 bd · 2 ba · 1,056 sq ft · built 2023
3822 Blueberry Ln, 33956
Cherry Estates
Listing courtesy of EXP Realty LLC
$424,900
2 bd · 2 ba · 1,499 sq ft · built 1977
3580 Gondola Ln, 33956
Gulfhaven
Listing courtesy of Century 21 Selling Paradise
$315,000
2 bd · 2 ba · 1,196 sq ft · built 2000
3056 Sloop Ln, 33956
Cherry Estates
Listing courtesy of LPT Realty, LLC
$379,000
3 bd · 2 ba · 1,770 sq ft · built 2026
3760 Gasparilla St, 33956
St James City
Listing courtesy of Legacy Premier Realty LLC
$364,900
3 bd · 2 ba · 1,549 sq ft · built 2026
3744 Gasparilla St, 33956
St James City
Listing courtesy of Legacy Premier Realty LLC

The most expensive $300k–$500k homes in St. James City

ListingAskingSq ftCommunity
2452 York Rd$499,0001,152Gulfhaven
3551 Heron Landing Cir$485,0001,645Eagle Lake Estates
5209 Western Drive$480,0001,512—
3524 5Th Ave$475,0001,518St James City
3400 Coquina Ln$459,9001,305St James City
3728 Gasparilla St$454,0002,372Pine Island Tropical Homesites
3728 Gasparilla Street$454,0002,372—
4507 Lake Heather Cir$450,0001,553Pine Island Village
4507 Lake Heather Circle$450,0001,553—
3435 Sea Holly Ln$449,9991,125St James City

$300K–$500K Homes by price

BandFor saleShare
$300K–$500K52100%

St James City homes $300K–$500K by community

Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.

CommunityHomes $300K–$500KNew buildMedian listFrom
Cherry Estates160$354,950$300,000
St James City90$439,000$335,000
Gulfhaven50$424,900$399,000
Pine Island Tropical Homesites50$345,000$325,000
Fishermans Wharf Condo30$325,900$305,000
Pine Island Village20$437,500$425,000
Gulf Haven20$382,400$374,900
Eagle Lake Estates11$485,000$485,000
P I Tropical Homesites10$454,000$454,000
Pine Island Village10$450,000$450,000
Gulfhaven10$450,000$450,000
St Jude Harbors10$449,999$449,999
St Jude Harbors10$409,900$409,900
St James City10$399,900$399,900
Flamingo Bay10$389,000$389,000
Trailerhaven10$380,000$380,000
Pine Island Shores Unit 210$359,000$359,000
Gulf Shores Estates10$344,000$344,000
Kreamers Avocado Subd10$300,000$300,000

Where this band sits in the market

The answer block above shows how the median of this band compares with the rest of the city’s listings, which tells you whether $300,000–$500,000 is the middle of the market here or the top of it. Within the band, compare on price per square foot and year built: newer subdivisions usually price higher per foot with lower expected maintenance, older ones the reverse. Each community page carries the HOA and CDD picture, the year-built range and the sales history, so two homes at the same price can be told apart in a few minutes.

Questions to ask about any listing in this band

What are the total monthly carrying costs (taxes, insurance, HOA, CDD) and how do they compare with a similar home two communities over? What is the age of the roof, HVAC and water heater? Is the community’s HOA financially healthy (reserves, no pending assessment)? How many days has the listing been on the market and has the price moved? A local agent who works the area will know which communities in this band are trading at asking and which are negotiating.

Common questions

How many homes listed between $300,000 and $500,000 are for sale in St James City?
As of October 2, 2026, 55 St James City, FL listings whose MLS record reports an asking price between $300,000 and $500,000 are active or pending, across 19 communities. The count updates with every MLS refresh.
What do homes $300K–$500K cost in St James City?
The median asking price today is $369,900, with listings from $300,000 to $499,000. St James City listings without that feature have a median of $559,900.
Which St James City community has the most homes $300K–$500K for sale?
Cherry Estates has the most right now (16), followed by St James City (9), Gulfhaven (5), Pine Island Tropical Homesites (5).
What is the monthly payment on a $400,000 home?
At today’s rates with 20% down, principal and interest on a $400,000 purchase runs roughly $2,000–$2,300 a month before taxes, insurance and any HOA; each listing page shows the property tax and fees for that home, and the true-cost calculator turns them into one monthly figure.

Keep exploring St James City

Homes $300K–$500K in nearby Lee County cities

Live data: Florida Gulf Coast MLS, Stellar MLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in St James City, FL whose MLS record reports an asking price between $300,000 and $500,000. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.

Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Listings courtesy of Stellar MLS as distributed by MLS GRID.

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