Homes for Sale in Siesta Key

Aerial view of Siesta Key homes lining a turquoise waterway that opens to the Gulf.

Property Listings

Price

Living Area

3941 Hamilton Club Cir 9 Sarasota Fl Us 34242 Mfra4712215

$2,195,000

3941 HAMILTON CLUB CIR #9, SARASOTA, FL 34242

3 Beds 4 Baths 2,856 Sq.Ft.

6157 Midnight Pass Rd E75 Sarasota Fl Us 34242 Mfra4711406

$419,000

6157 MIDNIGHT PASS RD #E75, SARASOTA, FL 34242

1 Bed 1 Bath 748 Sq.Ft.

6154 Midnight Pass Rd B1 Sarasota Fl Us 34242 Mfra4696503

$595,000

6154 MIDNIGHT PASS RD #B1, SARASOTA, FL 34242

2 Beds 1 Bath 836 Sq.Ft.

757 Beach Rd 310

$950,000

757 BEACH RD #310, SARASOTA, FL 34242

2 Beds 2 Baths 1,122 Sq.Ft.

5860 Midnight Pass Rd 38

$650,000

5860 MIDNIGHT PASS RD #38, SARASOTA, FL 34242

1 Bed 1 Bath 960 Sq.Ft.

523 Beach Rd

$8,249,000

523 BEACH RD, SARASOTA, FL 34242

19 Beds 12 Baths 6,972 Sq.Ft.

5760 Midnight Pass Rd 109

$1,289,000

5760 MIDNIGHT PASS RD #109, SARASOTA, FL 34242

3 Beds 2 Baths 1,473 Sq.Ft.

3936 Hamilton Club Cir 6

$1,400,000

3936 HAMILTON CLUB CIR #6, SARASOTA, FL 34242

3 Beds 3.5 Baths 2,691 Sq.Ft.

4839 Primrose Path

$2,800,000

4839 PRIMROSE PATH, SARASOTA, FL 34242

4 Beds 3.5 Baths 3,074 Sq.Ft.

5880 Midnight Pass Rd 706

$1,250,000

5880 MIDNIGHT PASS RD #706, SARASOTA, FL 34242

2 Beds 2 Baths 1,642 Sq.Ft.

6157 Midnight Pass Rd E24

$474,000

6157 MIDNIGHT PASS RD #E24, SARASOTA, FL 34242

1 Bed 1 Bath 748 Sq.Ft.

1300 N Portofino Dr 102

$449,995

1300 N PORTOFINO DR #102, SARASOTA, FL 34242

2 Beds 2 Baths 929 Sq.Ft.

5215 Calle De Costa Rica

$1,175,000

5215 CALLE DE COSTA RICA, SARASOTA, FL 34242

4 Beds 3 Baths 1,762 Sq.Ft.

5174 Sandy Cove Ave

$1,975,990

5174 SANDY COVE AVE, SARASOTA, FL 34242

6287 Midnight Pass Rd 106

$630,000

6287 MIDNIGHT PASS RD #106, SARASOTA, FL 34242

2 Beds 2 Baths 1,498 Sq.Ft.

1200 Cove Ii Pl 832

$549,900

1200 COVE II PL #832, SARASOTA, FL 34242

2 Beds 1.5 Baths 860 Sq.Ft.

6415 Midnight Pass Rd P10

$850,000

6415 MIDNIGHT PASS RD #P10, SARASOTA, FL 34242

2 Beds 2 Baths 1,290 Sq.Ft.

5780 Midnight Pass Rd 301

$1,500,000

5780 MIDNIGHT PASS RD #301, SARASOTA, FL 34242

2 Beds 3 Baths 1,739 Sq.Ft.

5324 Siesta Ct

$1,250,000

5324 SIESTA CT, SARASOTA, FL 34242

4 Beds 4 Baths 3,050 Sq.Ft.

1140 Windsong Ln A

$3,995,000

1140 WINDSONG LN #A, SARASOTA, FL 34242

5 Beds 6 Baths 3,891 Sq.Ft.

6018 W Peppertree Way 231b C

$1,124,900

6018 W PEPPERTREE WAY #231B C, SARASOTA, FL 34242

2 Beds 2 Baths 1,180 Sq.Ft.

1142 Windsong Ln

$7,900,000

1142 WINDSONG LN, SARASOTA, FL 34242

10 Beds 14 Baths 7,782 Sq.Ft.

4644 Higel Ave

$6,300,000

4644 HIGEL AVE, SARASOTA, FL 34242

4 Beds 5 Baths 3,482 Sq.Ft.

618 Avenida De Mayo

$1,200,000

618 AVENIDA DE MAYO, SARASOTA, FL 34242

5 Beds 4 Baths 2,961 Sq.Ft.

310 Avenida Milano

$1,100,000

310 AVENIDA MILANO, SARASOTA, FL 34242

3 Beds 2 Baths 1,582 Sq.Ft.

6006 Midnight Pass Rd 48

$299,900

6006 MIDNIGHT PASS RD #48, SARASOTA, FL 34242

1 Bath 420 Sq.Ft.

316 Beach Rd

$5,199,000

316 BEACH RD, SARASOTA, FL 34242

8 Beds 9 Baths 4,681 Sq.Ft.

5830 Midnight Pass Rd 61

$560,000

5830 MIDNIGHT PASS RD #61, SARASOTA, FL 34242

1 Bed 1 Bath 728 Sq.Ft.

67 Avenida Messina B

$3,900,000

67 AVENIDA MESSINA #B, SARASOTA, FL 34242

5 Beds 5 Baths 3,824 Sq.Ft.

40 Sandy Cove Rd 4c

$899,999

40 SANDY COVE RD #4C, SARASOTA, FL 34242

3 Beds 2 Baths 1,765 Sq.Ft.

5780 Midnight Pass Rd 210

$999,000

5780 MIDNIGHT PASS RD #210, SARASOTA, FL 34242

2 Beds 2 Baths 1,361 Sq.Ft.

4938 Commonwealth Dr

$2,650,000

4938 COMMONWEALTH DR, SARASOTA, FL 34242

4 Beds 3.5 Baths 2,169 Sq.Ft.

4026 Roberts Point Rd

$3,900,000

4026 ROBERTS POINT RD, SARASOTA, FL 34242

3 Beds 4.5 Baths 2,962 Sq.Ft.

925 Beach Rd 208

$565,000

925 BEACH RD #208, SARASOTA, FL 34242

2 Beds 1 Bath 753 Sq.Ft.

84 Avenida Veneccia 201

$5,995,000

84 AVENIDA VENECCIA #201, SARASOTA, FL 34242

3 Beds 2.5 Baths 3,118 Sq.Ft.

5858 Midnight Pass Rd 11

$749,900

5858 MIDNIGHT PASS RD #11, SARASOTA, FL 34242

3 Beds 2.5 Baths 1,104 Sq.Ft.

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Neighborhood Guides

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Our Blog

Late-afternoon light on pale jetty rocks beside calm turquoise inlet water on Florida’s Gulf Coast.

Friday Nights at North Jetty, and the Federal Report That Decides the Inlet's Edge

November 12, 2026

Cream-stucco home with a terracotta tile roof, recessed timber entry, limestone landing and a palm beside a curved garden approach.

Whole Foods Comes to State Road 64, and Lakewood Ranch's North-End Errand Run Gets Redrawn

November 5, 2026

Sunlit condominium terrace with limestone paving, closed white-framed glass doors, a weathered teak chair and a sea-grape specimen in a ceramic planter.

Downtown Sarasota's New Restaurants Are Mostly in Old Rooms. Caragiulos Built a New One.

October 29, 2026

Cream stucco home's recessed glazed entry and limestone approach beside a curved planting island with a coconut palm and three coonties after rain.

Venice Beach Has New Sand This Fall. So Where Did the Shark Teeth Go?

October 22, 2026

Cream stucco home with a clay-tile roof, arched glazed entry, worn pale limestone steps and one sculptural sea-grape tree.

Five Saturdays in a Row on St. Armands Circle, and the Longer Clock Running Underneath

October 15, 2026

Cream stucco home entrance with a tiled eave, closed bronze-framed glass door, limestone steps and a specimen palm.

Longboat Key's Town Center Green Has a Library on the Way. Here's What Has to Happen First.

October 8, 2026

Limestone kitchen island and teak cabinets beside glass doors overlooking a courtyard palm.

Why Siesta Key's Priciest Sale of 2026 Was Priced Three Times Before It Closed

October 1, 2026

Curved sand bunker edged by green grass on a golf course, with tracks across the sand.

7 Best Golf Clubs in Sarasota

Taylor Thompson | September 29, 2026

Discover seven of the best private and semi-private golf clubs in the Sarasota area, with course highlights, membership details and local links.

Pickleball paddle and green balls on a blue and green court.

Your Guide to Pickleball: 7 Best Places to Play Pickleball in Sarasota

Jennifer Thompson | September 29, 2026

Explore seven of the best places to play pickleball in Sarasota, including indoor courts, lighted parks and options on Siesta Key and Longboat Key.

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