| Address | Price | Bed / Bths | Interior Space | $sf | WF / Pool | MLS |
|---|---|---|---|---|---|---|
| 3990 HIGEL AVENUE |
$29,995,000 | 7/8 |
13,035sf | $2,301 | Y / Y | A4680585 |
| 7366 POINT OF ROCKS ROAD |
$26,000,000 | 5/5 |
10,600sf | $2,453 | Y / Y | A4673754 |
| 8250 SANDERLING ROAD |
$18,900,000 | 5/5 |
7,756sf | $2,437 | Y / Y | A4660281 |
| 3799 FLAMINGO AVENUE |
$18,500,000 | 4/4 |
8,138sf | $2,273 | Y / Y | A4653658 |
| 7324 POINT OF ROCKS ROAD |
$16,000,000 | 5/5 |
5,524sf | $2,896 | Y / Y | A4643281 |
| 4315 MANGROVE PLACE |
$14,500,000 | 6/6 |
7,535sf | $1,924 | Y / Y | A4659292 |
| 3440 GULFMEAD DRIVE |
$13,950,000 | 5/4 |
6,596sf | $2,115 | Y / Y | A4679384 |
| 3750 BAYOU LOUISE LANE |
$12,900,000 | 5/6 |
5,273sf | $2,446 | N / Y | A4686535 |
| 546 FREELING DRIVE |
$12,500,000 | 5/5 |
4,353sf | $2,872 | Y / Y | A4687147 |
| 3550 BAYOU LOUISE LANE |
$12,195,000 | 5/5 |
4,325sf | $2,820 | Y / Y | A4682295 |
| 1290 HIDDEN HARBOR WAY |
$11,975,000 | 5/5 |
6,079sf | $1,970 | Y / Y | A4673273 |
| 3210 HIGEL AVENUE |
$11,950,000 | 4/4 |
3,884sf | $3,077 | Y / Y | A4676047 |
| 3441 GULFMEAD DRIVE |
$10,500,000 | 6/6 |
4,769sf | $2,202 | Y / Y | A4684918 |
| 684 FREELING DRIVE |
$9,900,000 | 3/3 |
2,548sf | $3,885 | Y / Y | A4675752 |
| 4317 MIDNIGHT PASS ROAD |
$9,500,000 | 5/5 |
7,116sf | $1,335 | Y / Y | A4690271 |
| 1249 S BASIN LANE |
$8,950,000 | 6/6 |
8,737sf | $1,024 | Y / Y | A4690355 |
| 648 BEACH ROAD |
$8,750,000 | 3/2 |
4,750sf | $1,842 | Y / Y | A4681541 |
| 4034 ROBERTS POINT ROAD |
$8,500,000 | 5/4 |
5,458sf | $1,557 | Y / Y | A4693305 |
| 3820 FLAMINGO AVENUE |
$8,395,000 | 4/4 |
4,775sf | $1,758 | Y / Y | A4673215 |
| 7007 POINT OF ROCKS ROAD |
$8,000,000 | 8/8 |
4,997sf | $1,601 | N / Y | A4635010 |
| 5215 HIDDEN HARBOR ROAD |
$7,900,000 | 5/5 |
4,863sf | $1,625 | Y / Y | A4669367 |
| 5179 HIDDEN HARBOR ROAD |
$7,500,000 | 6/6 |
4,900sf | $1,531 | Y / Y | A4669099 |
| 4205 HIGEL AVENUE |
$7,500,000 | 4/4 |
7,003sf | $1,071 | Y / Y | A4675182 |
| 4634 HIGEL AVENUE |
$7,500,000 | 5/5 |
3,875sf | $1,935 | Y / Y | A4689982 |
| 44 ROCKWELL LANE |
$6,800,000 | 6/6 |
5,400sf | $1,259 | N / Y | A4685222 |
| 7152 POINT OF ROCKS CIRCLE |
$6,750,000 | 6/5 |
4,561sf | $1,480 | Y / Y | A4676052 |
| 5610 AVENIDA DEL MARE |
$6,400,000 | 8/8 |
5,313sf | $1,205 | N / Y | A4683170 |
| 6548 SABAL DRIVE |
$6,295,000 | 9/9 |
4,944sf | $1,273 | N / Y | A4688728 |
| 5132 JUNGLE PLUM ROAD |
$5,985,000 | 5/5 |
6,928sf | $864 | Y / Y | A4651663 |
| 527 FREELING DRIVE |
$5,825,000 | 4/4 |
4,310sf | $1,352 | Y / Y | A4669657 |
| 119 AVENIDA MESSINA |
$5,699,000 | 7/7 |
3,600sf | $1,583 | N / Y | A4656843 |
| 6536 PEACOCK ROAD |
$5,650,000 | 7/7 |
4,697sf | $1,203 | Y / Y | A4688703 |
| 332 AVENIDA DE MAYO |
$5,595,000 | 9/8 |
4,055sf | $1,380 | N / Y | A4687188 |
| 336 AVENIDA DE MAYO |
$5,595,000 | 8/8 |
3,811sf | $1,468 | N / Y | A4687301 |
| 316 BEACH ROAD |
$5,499,000 | 8/8 |
4,681sf | $1,175 | N / Y | A4683801 |
| 4136 ROBERTS POINT CIRCLE |
$5,499,000 | 6/5 |
7,099sf | $775 | Y / Y | A4670896 |
| 539 AVENIDA DEL NORTE |
$5,499,000 | 5/5 |
4,195sf | $1,311 | Y / Y | A4679096 |
| 7233 MIDNIGHT PASS ROAD |
$5,450,000 | 6/5 |
4,250sf | $1,282 | Y / Y | A4671054 |
| 4819 HIGEL AVENUE |
$5,392,000 | 4/4 |
4,220sf | $1,278 | Y / Y | A4620571 |
| 85 AVENIDA MESSINA |
$5,390,000 | 6/6 |
3,504sf | $1,538 | N / Y | A4686937 |
| 9200 BLIND PASS ROAD |
$5,250,000 | 4/4 |
4,000sf | $1,312 | Y / N | A4692471 |
| 135 AVENIDA VENECCIA |
$4,990,000 | 8/8 |
4,380sf | $1,139 | N / Y | A4670533 |
| 527 VENICE LANE |
$4,950,000 | 4/5 |
4,158sf | $1,190 | Y / Y | A4676628 |
| 533 VENICE LANE |
$4,800,000 | 4/5 |
3,765sf | $1,275 | Y / Y | A4676632 |
| 558 VENICE LANE |
$4,649,900 | 5/4 |
4,132sf | $1,125 | Y / Y | A4689132 |
| 5309 HIDDEN HARBOR ROAD |
$4,500,000 | 6/5 |
6,655sf | $676 | Y / Y | A4668550 |
| 5569 CAPE LEYTE DRIVE |
$4,495,000 | 5/4 |
3,654sf | $1,230 | Y / Y | A4685577 |
| 5174 SANDY COVE AVENUE |
$4,350,000 | 5/4 |
3,723sf | $1,168 | Y / Y | A4631631 |
| 7233 PINE NEEDLE ROAD |
$4,300,000 | 3/3 |
4,294sf | $1,001 | Y / Y | A4688394 |
| 5727 RIEGELS POINT ROAD |
$4,295,000 | 3/2 |
3,616sf | $1,188 | Y / Y | A4618421 |
| 7108 MIDNIGHT PASS ROAD |
$4,219,000 | 7/5 |
4,697sf | $898 | Y / Y | A4685107 |
| 656 TROPICAL CIRCLE |
$4,195,000 | 4/4 |
5,238sf | $801 | N / Y | A4674326 |
| 5045 OXFORD DRIVE |
$3,999,000 | 3/4 |
3,850sf | $1,039 | Y / Y | A4681817 |
| 847 FREELING DRIVE |
$3,950,000 | 4/4 |
4,034sf | $979 | Y / Y | A4690268 |
| 5531 CALLE DEL VERANO |
$3,800,000 | 4/4 |
3,200sf | $1,188 | N / Y | A4681732 |
| 8008 MIDNIGHT PASS ROAD |
$3,750,000 | 5/5 |
4,190sf | $895 | Y / Y | A4672889 |
| 765 SIESTA KEY CIRCLE |
$3,700,000 | 5/3 |
3,446sf | $1,074 | Y / Y | C7525634 |
| 603 TREMONT STREET |
$3,690,000 | 4/4 |
3,996sf | $923 | N / Y | A4685407 |
| 5263 AVENIDA DE CORTEZ |
$3,690,000 | 4/3 |
3,122sf | $1,182 | Y / Y | A4678861 |
| 3939 HIGEL AVENUE |
$3,675,000 | 4/4 |
3,788sf | $970 | N / N | A4675610 |
| 5103 WINDWARD AVENUE |
$3,549,000 | 3/4 |
3,034sf | $1,170 | Y / Y | A4676707 |
| 7333 POINT OF ROCKS ROAD |
$3,495,000 | 4/3 |
4,566sf | $765 | N / Y | A4651061 |
| 8800 MIDNIGHT PASS ROAD |
$3,490,000 | 4/4 |
3,676sf | $949 | N / Y | A4691173 |
| 611 TREMONT STREET |
$3,399,000 | 4/5 |
4,194sf | $810 | Y / Y | A4678455 |
| 1253 N BASIN LANE |
$3,295,000 | 4/4 |
3,464sf | $951 | Y / Y | A4668457 |
| 4903 COMMONWEALTH DRIVE |
$3,250,000 | 4/4 |
3,146sf | $1,033 | N / Y | A4643229 |
| 671 AVENIDA DEL NORTE |
$3,200,000 | 4/4 |
2,875sf | $1,113 | Y / Y | A4687911 |
| 276 ISLAND CIRCLE |
$3,100,000 | 4/3 |
2,292sf | $1,353 | Y / Y | A4667090 |
| 339 TREASURE BOAT WAY |
$3,000,000 | 4/3 |
2,689sf | $1,116 | Y / Y | A4685922 |
| 300 GARDEN LANE |
$2,999,000 | 4/4 |
3,256sf | $921 | Y / Y | A4662830 |
| 7401-B MIDNIGHT PASS ROAD |
$2,999,000 | 4/4 |
2,735sf | $1,097 | N / Y | A4622370 |
| 7647 SANDERLING ROAD |
$2,998,000 | 4/3 |
4,006sf | $748 | Y / Y | TB8486392 |
| 732 SIESTA DRIVE |
$2,995,000 | 3/4 |
3,743sf | $800 | Y / Y | A4640849 |
| 62 SANDY HOOK ROAD S |
$2,995,000 | 5/3 |
2,658sf | $1,127 | Y / N | A4667491 |
| 238 ISLAND CIRCLE |
$2,900,000 | 4/4 |
2,854sf | $1,016 | Y / Y | A4650032 |
| 4938 COMMONWEALTH DRIVE |
$2,900,000 | 4/3 |
2,169sf | $1,337 | Y / Y | A4683758 |
| 126/128 AVENIDA VENECCIA |
$2,850,000 | 5/4 |
3,260sf | $874 | N / N | A4673661 |
| 8504 HERON LAGOON CIRCLE |
$2,800,000 | 4/4 |
2,675sf | $1,047 | N / Y | A4681098 |
| 8213 MIDNIGHT PASS ROAD |
$2,800,000 | 3/3 |
3,328sf | $841 | Y / Y | A4686208 |
| 6907 BOCHI CIRCLE |
$2,800,000 | 4/4 |
2,970sf | $943 | N / Y | A4692735 |
| 5303 HIDDEN HARBOR ROAD |
$2,795,000 | 3/2 |
3,201sf | $873 | Y / Y | N6143036 |
| 4839 GIVENS COURT |
$2,750,000 | 5/5 |
3,524sf | $780 | N / Y | A4683309 |
| 1267 STARBOARD LANE |
$2,750,000 | 2/2 |
2,510sf | $1,096 | Y / Y | A4685077 |
| 8555 HERON LAGOON CIRCLE |
$2,725,000 | 4/3 |
2,568sf | $1,061 | N / N | A4646820 |
| 8560 HERON LAGOON CIRCLE |
$2,695,000 | 4/3 |
3,956sf | $681 | N / Y | A4682353 |
| 6901 BOCHI CIRCLE |
$2,675,000 | 4/4 |
2,729sf | $980 | N / Y | A4692713 |
| 5331 SIESTA COVE DRIVE |
$2,600,000 | 3/3 |
3,795sf | $685 | N / Y | A4628363 |
| 3458 ANGLIN DRIVE |
$2,595,000 | 4/2 |
2,513sf | $1,033 | N / Y | A4683447 |
| 1248 NORTHPORT DRIVE |
$2,500,000 | 4/3 |
3,250sf | $769 | Y / Y | A4668459 |
| 4508 WOODSIDE ROAD |
$2,450,000 | 3/2 |
2,276sf | $1,076 | Y / Y | A4674684 |
| 7345 PINE NEEDLE ROAD |
$2,350,000 | 4/4 |
2,977sf | $789 | N / Y | A4690626 |
| 3508 LA PALOMA AVENUE |
$2,250,000 | 5/3 |
3,195sf | $704 | N / Y | A4686192 |
| 5361 SIESTA CT |
$2,249,000 | 4/2 |
2,774sf | $811 | N / Y | TB8455948 |
| 5012 HIGEL AVENUE |
$2,249,000 | 4/3 |
3,541sf | $635 | Y / Y | A4658844 |
| 462 ISLAND CIRCLE |
$2,240,000 | 3/2 |
1,670sf | $1,341 | Y / Y | A4641791 |
| 8456 MIDNIGHT PASS ROAD |
$2,200,000 | 2/1 |
966sf | $2,277 | Y / N | TB8497342 |
| 589 COMMONWEALTH LANE |
$2,200,000 | 4/2 |
2,073sf | $1,061 | N / Y | R4910990 |
| 5155 HIDDEN HARBOR ROAD |
$1,995,000 | 3/2 |
2,233sf | $893 | Y / Y | G5107159 |
| 814 PARADISE WAY |
$1,995,000 | 4/2 |
1,996sf | $999 | Y / Y | TB8483961 |
| 116 GARDEN LANE |
$1,995,000 | 4/3 |
2,971sf | $671 | N / N | A4671064 |
| 6962 BELGRAVE DRIVE |
$1,950,000 | 3/2 |
2,224sf | $877 | Y / Y | A4670404 |
| 5334 CALLE FLORIDA |
$1,870,000 | 4/3 |
2,838sf | $659 | N / Y | A4676260 |
| 3515 LA PALOMA AVENUE |
$1,800,000 | 4/3 |
2,233sf | $806 | N / Y | A4689037 |
| 7221 PLOVERS WAY |
$1,795,000 | 3/3 |
2,748sf | $653 | N / Y | A4675508 |
| 5507 CONTENTO DRIVE |
$1,775,000 | 3/3 |
1,788sf | $993 | Y / Y | A4683288 |
| 5569 CONTENTO DRIVE |
$1,749,000 | 2/2 |
1,772sf | $987 | Y / Y | A4670108 |
| 156 SIESTA DRIVE |
$1,649,000 | 5/3 |
2,901sf | $568 | N / Y | A4661717 |
| 5231 SIESTA COVE DRIVE |
$1,600,000 | 3/2 |
2,557sf | $626 | N / Y | A4686013 |
| 3360 HIGEL AVENUE |
$1,549,000 | 4/3 |
2,006sf | $772 | N / Y | A4682008 |
| 746 PLYMOUTH STREET |
$1,500,000 | 4/3 |
2,185sf | $686 | N / Y | A4639522 |
| 5560 SHADOW LAWN DRIVE |
$1,499,000 | 4/3 |
2,124sf | $706 | Y / Y | A4636955 |
| 5169 OXFORD DRIVE |
$1,498,800 | 3/3 |
1,658sf | $904 | Y / Y | V4948468 |
| 5201 AVENIDA DEL MARE |
$1,450,000 | 4/3 |
2,802sf | $517 | N / Y | A4680975 |
| 324 SIESTA DRIVE |
$1,400,000 | 5/4 |
2,510sf | $558 | N / Y | A4692790 |
| 854 NORSOTA WAY |
$1,399,000 | 2/2 |
1,667sf | $839 | N / Y | A4665123 |
| 4939 COMMONWEALTH DRIVE |
$1,390,000 | 3/3 |
2,090sf | $665 | N / Y | A4684397 |
| 4646 GLEASON AVENUE |
$1,350,000 | 4/4 |
2,927sf | $461 | N / Y | A4677470 |
| 445 REID STREET |
$1,340,000 | 3/2 |
1,750sf | $766 | N / Y | A4671563 |
| 8534 HERON LAGOON CIRCLE |
$1,299,000 | 2/2 |
1,153sf | $1,127 | N / Y | A4687653 |
| 5324 SIESTA COURT |
$1,250,000 | 3/4 |
3,050sf | $410 | N / N | A4682581 |
| 5569 SHADOW LAWN DRIVE |
$1,250,000 | 3/2 |
2,074sf | $603 | N / Y | A4691399 |
| 5107 SAINT ALBANS AVENUE |
$1,249,000 | 3/2 |
2,241sf | $557 | N / Y | A4678525 |
| 618 AVENIDA DE MAYO |
$1,200,000 | 5/4 |
2,961sf | $405 | N / N | A4692001 |
| 5345 SIESTA COURT |
$1,160,000 | 3/2 |
2,272sf | $511 | N / N | A4685607 |
| 5453 AVENIDA DEL MARE |
$1,150,000 | 3/3 |
1,510sf | $762 | N / N | A4669037 |
| 611 VENICE LANE |
$1,072,000 | 3/2 |
2,168sf | $494 | N / Y | A4686684 |
| 226 OGDEN STREET |
$1,000,000 | 2/2 |
1,559sf | $641 | N / Y | A4668141 |
Discover Siesta Key — Sarasota's Premier Island Paradise
Siesta Key is one of Southwest Florida’s most iconic barrier islands, renowned for its powdery white quartz sand beaches, turquoise waters, and vibrant island lifestyle. Just minutes from Downtown Sarasota and West of Trail neighborhoods, Siesta Key offers a rare combination of luxury real estate, outdoor recreation, and a welcoming community atmosphere. From luxury beachfront estates to modern condos, Siesta Key continues to attract buyers seeking primary residences, seasonal retreats, or high-performing investment properties.
Siesta Key Real Estate Overview
The Siesta Key real estate market offers a diverse range of properties, catering to every lifestyle and investment goal. Whether you’re searching for a waterfront mansion, a contemporary condo with sweeping Gulf views, or a charming island cottage, Siesta Key delivers exceptional options.
- Waterfront Homes: Gulf-front and canal-front residences offer private docks, boat lifts, and seamless access to Sarasota Bay and the Gulf of Mexico.
- Luxury Condos & Villas: High-end towers and boutique complexes provide maintenance-free living with resort-style amenities and panoramic views.
- Single-Family Residences: From Old Florida-style cottages to new custom-built homes, the island features a mix of architectural styles suited for full-time or seasonal living.
- Investment Properties: Short-term rental-friendly units offer strong ROI due to high tourist demand and peak-season occupancy.
Why Buy in Siesta Key?
1. Award-Winning Beaches & Natural Beauty: Siesta Key Beach is consistently ranked among the top beaches in the U.S., famed for its soft quartz sand and clear waters. Crescent Beach and Turtle Beach provide more secluded experiences with excellent snorkeling, shelling, and kayaking.
2. Active Coastal Lifestyle: Residents enjoy year-round outdoor activities including boating, paddleboarding, fishing, beach yoga, and cycling along the island’s scenic paths and nature preserves.
3. Strong Rental Income Potential: With a high influx of visitors, properties suitable for weekly or short-term rentals offer excellent investment opportunities.
4. Community & Safety: Siesta Key maintains a safe, family-friendly environment with a tight-knit community ideal for retirees, young families, and seasonal homeowners.
5. Proximity to Downtown Sarasota: Only 15 minutes from the city, residents enjoy access to cultural attractions, fine dining, shopping, top-rated schools, and healthcare facilities.
Local Attractions & Amenities
Siesta Key Village: The island’s social and cultural hub, featuring restaurants, boutique shops, coffee houses, and live music venues. Popular spots include The Cottage, Gilligan’s Island Bar, and Big Olaf Creamery.
Outdoor Recreation: Kayaking, sailing, paddleboarding, and nature trails abound, including launches at Turtle Beach Park and scenic sunset cruises.
Festivals & Events: Seasonal events like the Siesta Key Crystal Classic sand sculpting competition and Sunday Drum Circles create a vibrant island culture.
Dining & Nightlife: Fresh seafood, tropical cocktails, and beachfront views are highlights at Ophelia’s on the Bay, Daiquiri Deck, and Summer House Steak & Seafood.
Shopping: Coastal boutiques, local galleries, and beach gear shops are complemented by upscale retail options at St. Armands Circle and downtown Sarasota.
Architectural Styles & Home Features
Siesta Key homes range from Mediterranean-inspired villas and Key West-style cottages to modern beachfront estates. Open-plan layouts, indoor-outdoor living spaces, hurricane-resistant construction, smart home technology, and energy-efficient features cater to contemporary buyers while embracing the island’s coastal charm.
Market Trends & Real Estate Tips
Inventory: Limited buildable land contributes to high property values and competitive demand.
Appreciation: Long-term historical growth makes Siesta Key an excellent investment choice.
Rental Regulations: Zoning and HOA rules vary, so understanding restrictions is key for short-term rentals.
Local Expertise: Working with a Sarasota real estate professional provides access to off-market properties, seasonal pricing insights, and investment guidance.
Nearby Communities & Comparisons
Compared with neighboring Lido Key and Longboat Key, Siesta Key offers a more relaxed, walkable beach-town lifestyle. Lido Key is known for proximity to St. Armands Circle, and Longboat Key emphasizes exclusivity and golf communities. Siesta Key combines natural beauty, vibrant island life, and high rental potential for a truly unique Sarasota experience.
Experience Siesta Key Living
From sunrise walks along Crescent Beach to evening cocktails in the Village, Siesta Key provides a lifestyle defined by sun, sea, and sophistication. Luxury real estate, outdoor activities, and community charm make the island one of Florida’s most desirable coastal destinations.
Explore elevated living at Siesta Key — where luxury, location, and lifestyle meet seamlessly. I am Sarasota’s leading Sales expert. Contact me at 941.281.5472 or email lisa@sarasotaluxurycondos.com.
Available Properties in Siesta Key
Siesta Key Location
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