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Gulf Pines Houses Sold55+ Active Adult

Mid-Tier
Ultra Luxury — Above $1,000 per SqFt
High-End — $650 - $1,000 per SqFt
Mid-Tier — $400 - $650 per SqFt
Premium — $300 - $400 per SqFt
Entry-Level — Below $300 per SqFt
Rank (0)
Reviews ()
For Sale
2
$925K–$999K
For Rent
0
Avg. Price
$999K
Current Ask
Avg. Days
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Results 29 of 39
Sold - Oct 27, 2026
Gulf Pines, 4339 Gulf Pines Dr, Sanibel, Florida 33957, image 1
$875,000$74K
  • 3 Beds
  • 2 Baths
  • 1,473 SqFt
  • $594/SqFt
Mid-Tier
House sold in Gulf Pines
4339 Gulf Pines Dr, Sanibel, FL 33957
Listing Courtesy Of: Kingfisher Real Estate, Inc.
Sold - Jul 27, 2026
Gulf Pines, 928 Pepper Tree Pl, Sanibel, Florida 33957, image 1
$995,000$54K
  • 3 Beds
  • 2 Baths
  • 1,829 SqFt
  • $544/SqFt
  • $1,880/mo HOA
Mid-Tier
House sold in Gulf Pines
928 Pepper Tree Pl, Sanibel, FL 33957
Listing Courtesy Of: Pfeifer Realty Group LLC
Sold - Jun 2, 2026
Gulf Pines, 4383 Gulf Pines Dr, Sanibel, Florida 33957, image 1
$2,250,000$248K
  • 5 Beds
  • 41/2 Baths
  • 4,678 SqFt
  • $481/SqFt
Mid-Tier
House sold in Gulf Pines
4383 Gulf Pines Dr, Sanibel, FL 33957
Listing Courtesy Of: Kingfisher Real Estate, Inc.
Sold - May 29, 2026
Gulf Pines, 4353 Gulf Pines Dr, Sanibel, Florida 33957, image 1
$1,325,000$70K
  • 3 Beds
  • 21/2 Baths
  • 2,475 SqFt
  • $535/SqFt
  • $1,825/mo HOA
Mid-Tier
House sold in Gulf Pines
4353 Gulf Pines Dr, Sanibel, FL 33957
Listing Courtesy Of: John R. Wood Properties
Sold - Mar 19, 2026
Gulf Pines, 4245 Gulf Pines Dr, Sanibel, Florida 33957, image 1
$844,000$235K
  • 3 Beds
  • 2 Baths
  • 2,014 SqFt
  • $419/SqFt
  • $1,780/mo HOA
Mid-Tier
House sold in Gulf Pines
4245 Gulf Pines Dr, Sanibel, FL 33957
Listing Courtesy Of: Pfeifer Realty Group LLC
Sold - Feb 12, 2026
Gulf Pines, 931 Snowberry Ln, Sanibel, Florida 33957, image 1
$1,250,000$145K
  • 4 Beds
  • 4 Baths
  • 2,222 SqFt
  • $563/SqFt
Mid-Tier
House sold in Gulf Pines
931 Snowberry Ln, Sanibel, FL 33957
Listing Courtesy Of: Kingfisher Real Estate, Inc.
Sold - Dec 18, 2025
Gulf Pines, 4221 Old Banyan Way, Sanibel, Florida 33957, image 1
$980,000$395K
  • 3 Beds
  • 2 Baths
  • 1,511 SqFt
  • $649/SqFt
  • $1,696/mo HOA
Mid-Tier
House sold in Gulf Pines
4221 Old Banyan Way, Sanibel, FL 33957
Listing Courtesy Of: Berkshire Hathaway Florida
Sold - Nov 18, 2025
Gulf Pines, 984 Black Skimmer Way, Sanibel, Florida 33957, image 1
$800,000$38K
  • 3 Beds
  • 2 Baths
  • 1,503 SqFt
  • $532/SqFt
Mid-Tier
House sold in Gulf Pines
984 Black Skimmer Way, Sanibel, FL 33957
Listing Courtesy Of: Kingfisher Real Estate, Inc.
Sold - Jun 18, 2025
Gulf Pines, 1027 Bird Watch Way, Sanibel, Florida 33957, image 1
$750,000$75K
  • 3 Beds
  • 2 Baths
  • 1,308 SqFt
  • $573/SqFt
Mid-Tier
House for sale in Gulf Pines
1027 Bird Watch Way, Sanibel, FL 33957
Listing Courtesy Of: Kingfisher Real Estate, Inc.
Sold - May 9, 2025
Gulf Pines, 906 Snowberry Ln, Sanibel, Florida 33957, image 1
$3,950,000
  • 4 Beds
  • 41/2 Baths
  • 3,451 SqFt
  • $1,145/SqFt
  • $1,780/mo HOA
Mid-Tier
House for sale in Gulf Pines
906 Snowberry Ln, Sanibel, FL 33957
Listing Courtesy Of: Pfeifer Realty Group LLC
Sold - Mar 12, 2025
Gulf Pines, 4372 Gulf Pines Dr, Sanibel, Florida 33957, image 1
$810,000$175K
  • 3 Beds
  • 2 Baths
  • 1,271 SqFt
  • $637/SqFt
Mid-Tier
House for sale in Gulf Pines
4372 Gulf Pines Dr, Sanibel, FL 33957
Listing Courtesy Of: Kingfisher Real Estate, Inc.
Sold - Mar 3, 2025
Gulf Pines, 920 Snowberry Ln, Sanibel, Florida 33957, image 1
$1,190,000
  • 3 Beds
  • 31/2 Baths
  • 2,475 SqFt
  • $481/SqFt
  • $1,780/mo HOA
Mid-Tier
House for sale in Gulf Pines
920 Snowberry Ln, Sanibel, FL 33957
Listing Courtesy Of: Pfeifer Realty Group LLC
Sold - May 30, 2024
Gulf Pines, 930 Strangler Fig Ln, Sanibel, Florida 33957, image 1
$1,300,000
  • 5 Beds
  • 31/2 Baths
  • 3,150 SqFt
  • $413/SqFt
  • $1,696/mo HOA
Mid-Tier
House for sale in Gulf Pines
930 Strangler Fig Ln, Sanibel, FL 33957
Listing Courtesy Of: Pfeifer Realty Group LLC
Sold - Apr 18, 2024
Gulf Pines, 4269 Gulf Pines Dr, Sanibel, Florida 33957, image 1
$600,000
  • 2 Beds
  • 2 Baths
  • 1,424 SqFt
  • $421/SqFt
  • $1,615/mo HOA
Mid-Tier
House for sale in Gulf Pines
4269 Gulf Pines Dr, Sanibel, FL 33957
Listing Courtesy Of: Timbers FL Real Estate Company
Sold - Mar 26, 2024
Gulf Pines, 4279 Gulf Pines Dr, Sanibel, Florida 33957, image 1
$1,200,000
  • 4 Beds
  • 3 Baths
  • 2,109 SqFt
  • $569/SqFt
  • $1,696/mo HOA
Mid-Tier
House for sale in Gulf Pines
4279 Gulf Pines Dr, Sanibel, FL 33957
Listing Courtesy Of: Pfeifer Realty Group LLC
Sold - Mar 20, 2024
Gulf Pines, 4415 Gulf Pines Dr, Sanibel, Florida 33957, image 1
$1,675,000
  • 3 Beds
  • 3 Baths
  • 2,568 SqFt
  • $652/SqFt
Mid-Tier
House for sale in Gulf Pines
4415 Gulf Pines Dr, Sanibel, FL 33957
Listing Courtesy Of: Berkshire Hathaway Florida
Sold - Mar 6, 2024
Gulf Pines, 4263 Gulf Pines Dr, Sanibel, Florida 33957, image 1
$750,000
  • 3 Beds
  • 2 Baths
  • 1,220 SqFt
  • $615/SqFt
  • $1,696/mo HOA
Mid-Tier
House for sale in Gulf Pines
4263 Gulf Pines Dr, Sanibel, FL 33957
Listing Courtesy Of: John R. Wood Properties
Sold - Feb 20, 2024
Gulf Pines, 957 Cabbage Palm Ct, Sanibel, Florida 33957, image 1
$1,275,000
  • 3 Beds
  • 3 Baths
  • 1,889 SqFt
  • $675/SqFt
  • $1,696/mo HOA
Mid-Tier
House for sale in Gulf Pines
957 Cabbage Palm Ct, Sanibel, FL 33957
Listing Courtesy Of: Pfeifer Realty Group LLC
Sold - Feb 6, 2024
Gulf Pines, 923 Snowberry Ln, Sanibel, Florida 33957, image 1
$1,075,000
  • 3 Beds
  • 3 Baths
  • 2,100 SqFt
  • $512/SqFt
Mid-Tier
House for sale in Gulf Pines
923 Snowberry Ln, Sanibel, FL 33957
Listing Courtesy Of: Kingfisher Real Estate, Inc.
Sold - Dec 22, 2023
Gulf Pines, 4389 Gulf Pines Dr, Sanibel, Florida 33957, image 1
$1,550,000
  • 3 Beds
  • 32/2 Baths
  • 3,110 SqFt
  • $498/SqFt
  • $1,696/mo HOA
Mid-Tier
House for sale in Gulf Pines
4389 Gulf Pines Dr, Sanibel, FL 33957
Listing Courtesy Of: Pfeifer Realty Group LLC
Sold - Jul 20, 2023
Gulf Pines, 950 Cabbage Palm Ct, Sanibel, Florida 33957, image 1
$1,225,000
  • 3 Beds
  • 2 Baths
  • 2,797 SqFt
  • $438/SqFt
  • $1,615/mo HOA
Mid-Tier
House for sale in Gulf Pines
950 Cabbage Palm Ct, Sanibel, FL 33957
Listing Courtesy Of: Kingfisher Real Estate, Inc.
Sold - Feb 28, 2023
Gulf Pines, 4427 Gulf Pines Dr, Sanibel, Florida 33957, image 1
$675,000
  • 3 Beds
  • 21/2 Baths
  • 2,224 SqFt
  • $304/SqFt
  • $1,615/mo HOA
Mid-Tier
House for sale in Gulf Pines
4427 Gulf Pines Dr, Sanibel, FL 33957
Listing Courtesy Of: John R. Wood Properties
Sold - Feb 28, 2023
Gulf Pines, 1031 Bird Watch Way, Sanibel, Florida 33957, image 1
$800,000
  • 3 Beds
  • 2 Baths
  • 1,911 SqFt
  • $419/SqFt
Mid-Tier
House for sale in Gulf Pines
1031 Bird Watch Way, Sanibel, FL 33957
Listing Courtesy Of: John R. Wood Properties
Sold - Jan 23, 2023
Gulf Pines, 921 Strangler Fig Ln, Sanibel, Florida 33957, image 1
$750,000
  • 3 Beds
  • 21/2 Baths
  • 2,556 SqFt
  • $293/SqFt
  • $1,615/mo HOA
Mid-Tier
House for sale in Gulf Pines
921 Strangler Fig Ln, Sanibel, FL 33957
Listing Courtesy Of: McCallion & McCallion
Gulf Pines, 917 Pepper Tree Pl, Sanibel, Florida 33957, image 1
$1,436,000
  • 4 Beds
  • 3 Baths
  • 2,732 SqFt
  • $526/SqFt
  • $1,465/mo HOA
Mid-Tier
House for sale in Gulf Pines
917 Pepper Tree Pl, Sanibel, FL 33957
Listing Courtesy Of: RE/MAX of The Islands
Gulf Pines, 4202 Old Banyan Way, Sanibel, Florida 33957, image 1
$1,525,000
  • 3 Beds
  • 21/2 Baths
  • 1,745 SqFt
  • $874/SqFt
  • $1,538/mo HOA
Mid-Tier
House for sale in Gulf Pines
4202 Old Banyan Way, Sanibel, FL 33957
Listing Courtesy Of: John Naumann & Associates
Gulf Pines, 4239 Gulf Pines Dr, Sanibel, Florida 33957, image 1
$939,000
  • 3 Beds
  • 2 Baths
  • 1,559 SqFt
  • $602/SqFt
  • $1,538/mo HOA
Mid-Tier
House for sale in Gulf Pines
4239 Gulf Pines Dr, Sanibel, FL 33957
Listing Courtesy Of: McCallion & McCallion
Gulf Pines, 4285 Gulf Pines Dr, Sanibel, Florida 33957, image 1
$900,000
  • 3 Beds
  • 2 Baths
  • 1,740 SqFt
  • $517/SqFt
Mid-Tier
House for sale in Gulf Pines
4285 Gulf Pines Dr, Sanibel, FL 33957
Listing Courtesy Of: John R. Wood Properties
Gulf Pines, 4452 Gulf Pines Dr, Sanibel, Florida 33957, image 1
$899,900
  • 3 Beds
  • 2 Baths
  • 2,084 SqFt
  • $432/SqFt
Mid-Tier
House for sale in Gulf Pines
4452 Gulf Pines Dr, Sanibel, FL 33957
Listing Courtesy Of: RE/MAX Trend

Subdivision Amenities

Beach Access
Clubhouse
Community Room
Guest Room
Internet Access
Pool
See Remarks
Tennis Court(s)
Barbecue
Beach Access
Pool

Frequently Asked Questions

Nearby Subdivisions

Entry-Level
0.26 miles
Mid-Tier
0.28 miles
For Sale (3)
$1.3M - $6.3M
For Rent (1)
$15K - $15K
Entry-Level
0.51 miles
Premium
0.53 miles
For Sale (3)
$789K - $1.4M
Mid-Tier
0.59 miles
For Sale (1)
$6.5M - $6.5M

Scores

Walk Score®
Car-Dependent. Almost all errands require a car
2

100
Bike Score®
Somewhat Bikeable. Minimal bike infrastructure
44

100
Sound Score®
Bearable noise
80

100
Airport Score
Close to airports. Noticeable airport activity
0

100
Traffic Score
Congested area. Frequent traffic delays
24

100
Local Score
Limited local amenities nearby
0

100

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