| Address | Price | Bed / Bths | Interior Space | $sf | WF / Pool | MLS |
|---|---|---|---|---|---|---|
| 7366 POINT OF ROCKS ROAD |
$26,000,000 | 5/5 |
10,600sf | $2,453 | Y / Y | A4673754 |
| 4050 HIGEL AVENUE |
$22,000,000 | 5/6 |
6,301sf | $3,492 | Y / Y | A4677328 |
| 8250 SANDERLING ROAD |
$18,900,000 | 5/5 |
7,756sf | $2,437 | Y / Y | A4660281 |
| 7324 POINT OF ROCKS ROAD |
$16,000,000 | 0/ |
5,524sf | $2,896 | Y / Y | A4643281 |
| 4315 MANGROVE PLACE |
$15,950,000 | 0/ |
7,535sf | $2,117 | Y / Y | A4659292 |
| 3200 HIGEL AVENUE |
$14,500,000 | 5/6 |
4,853sf | $2,988 | Y / Y | A4672890 |
| 1192 HORIZON VIEW DRIVE |
$13,900,000 | 6/6 |
8,358sf | $1,663 | Y / Y | A4652708 |
| 4046 HIGEL AVENUE |
$13,500,000 | 6/5 |
6,468sf | $2,087 | Y / Y | A4672518 |
| 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 | A4677349 |
| 684 FREELING DRIVE |
$9,900,000 | 3/3 |
2,548sf | $3,885 | Y / Y | A4675752 |
| 21 LANDS END LANE |
$9,900,000 | 6/7 |
5,060sf | $1,957 | N / Y | A4668017 |
| 3820 FLAMINGO AVENUE |
$8,395,000 | 4/4 |
4,775sf | $1,758 | Y / Y | A4673215 |
| 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 |
| 8585 MIDNIGHT PASS ROAD |
$7,390,000 | 4/5 |
5,727sf | $1,290 | Y / Y | A4660258 |
| 3550 FLAMINGO AVENUE |
$6,595,000 | 4/4 |
4,711sf | $1,400 | Y / Y | A4610537 |
| 5132 JUNGLE PLUM ROAD |
$6,400,000 | 5/5 |
6,928sf | $924 | Y / Y | A4651663 |
| 5507 CALLE DEL INVIERNO |
$6,000,000 | 5/5 |
4,496sf | $1,335 | N / Y | A4667675 |
| 538 CANAL ROAD |
$5,985,000 | 8/6 |
4,094sf | $1,462 | Y / Y | A4656047 |
| 7233 MIDNIGHT PASS ROAD |
$5,950,000 | 6/5 |
4,250sf | $1,400 | Y / Y | A4671054 |
| 119 AVENIDA MESSINA |
$5,900,000 | 7/7 |
3,600sf | $1,639 | N / Y | A4656843 |
| 527 FREELING DRIVE |
$5,825,000 | 4/4 |
4,310sf | $1,352 | Y / Y | A4669657 |
| 684 FREELING DRIVE |
$5,750,000 | 3/3 |
2,548sf | $2,257 | Y / Y | A4675757 |
| 4644 HIGEL AVENUE |
$5,500,000 | 4/4 |
3,482sf | $1,580 | Y / Y | A4676102 |
| 579 COMMONWEALTH LANE |
$5,500,000 | 5/5 |
4,508sf | $1,220 | Y / Y | A4672499 |
| 843 NORSOTA WAY |
$5,499,000 | 3/2 |
2,467sf | $2,229 | Y / Y | A4676472 |
| 4136 ROBERTS POINT CIRCLE |
$5,499,000 | 6/5 |
7,099sf | $775 | Y / Y | A4670896 |
| 4819 HIGEL ROAD |
$5,392,000 | 4/4 |
4,220sf | $1,278 | Y / Y | A4620571 |
| 5727 RIEGELS POINT ROAD |
$5,325,000 | 3/2 |
3,616sf | $1,473 | Y / Y | A4618421 |
| 7647 SANDERLING ROAD |
$5,300,000 | 4/3 |
4,006sf | $1,323 | Y / Y | A4653020 |
| 135 AVENIDA VENECCIA |
$5,290,000 | 8/8 |
4,380sf | $1,208 | N / Y | A4670533 |
| 831 SIESTA DRIVE |
$5,100,000 | 5/4 |
4,250sf | $1,200 | N / Y | A4674955 |
| 7340 PINE NEEDLE ROAD |
$4,995,000 | 4/4 |
3,780sf | $1,321 | N / Y | A4674568 |
| 749 FREELING DRIVE |
$4,995,000 | 4/4 |
6,827sf | $732 | N / Y | A4666354 |
| 3607 FLAMINGO AVENUE |
$4,950,000 | 4/4 |
3,876sf | $1,277 | Y / Y | A4662402 |
| 527 VENICE LANE |
$4,950,000 | 4/5 |
4,158sf | $1,190 | Y / Y | A4676628 |
| 5309 HIDDEN HARBOR ROAD |
$4,900,000 | 6/5 |
6,655sf | $736 | Y / Y | A4668550 |
| 8592 HIDDEN LAGOON ROAD |
$4,900,000 | 4/4 |
3,632sf | $1,349 | Y / N | A4648285 |
| 750 SIESTA KEY CIRCLE |
$4,850,000 | 4/4 |
4,213sf | $1,151 | Y / Y | A4676958 |
| 533 VENICE LANE |
$4,800,000 | 4/5 |
3,765sf | $1,275 | Y / Y | A4676632 |
| 558 VENICE LANE |
$4,799,000 | 4/4 |
4,132sf | $1,161 | Y / Y | A4589732 |
| 878 FREELING DRIVE |
$4,795,000 | 4/4 |
3,866sf | $1,240 | Y / Y | A4673685 |
| 225 LITTLE POND LANE |
$4,450,000 | 5/4 |
3,867sf | $1,151 | Y / Y | A4668094 |
| 262 ISLAND CIRCLE |
$4,195,000 | 4/4 |
3,455sf | $1,214 | Y / Y | A4668568 |
| 656 TROPICAL CIRCLE |
$4,195,000 | 4/4 |
5,238sf | $801 | N / Y | A4674326 |
| 7314 POINT OF ROCKS ROAD |
$3,999,995 | 4/4 |
2,977sf | $1,344 | Y / N | A4668466 |
| 5174 SANDY COVE AVENUE |
$3,999,995 | 5/4 |
3,723sf | $1,074 | Y / Y | A4631631 |
| 7333 POINT OF ROCKS ROAD |
$3,995,000 | 4/3 |
4,566sf | $875 | N / Y | A4651061 |
| 603 TREMONT STREET |
$3,990,000 | 4/4 |
3,996sf | $998 | N / Y | A4666753 |
| 8800 MIDNIGHT PASS ROAD |
$3,990,000 | 4/4 |
3,676sf | $1,085 | N / Y | A4677232 |
| 1364 POINT CRISP ROAD |
$3,975,000 | 4/5 |
4,562sf | $871 | Y / Y | A4643388 |
| 4129 ROBERTS POINT CIRCLE |
$3,950,000 | 3/3 |
4,484sf | $881 | N / Y | A4642942 |
| 8008 MIDNIGHT PASS ROAD |
$3,950,000 | 5/5 |
4,190sf | $943 | Y / Y | A4672889 |
| 3939 HIGEL AVENUE |
$3,775,000 | 4/4 |
3,788sf | $997 | N / N | A4675610 |
| 5103 WINDWARD AVENUE |
$3,657,625 | 3/4 |
3,034sf | $1,206 | Y / Y | A4676707 |
| 838 NORSOTA WAY |
$3,650,000 | 5/5 |
3,001sf | $1,216 | N / Y | A4677343 |
| 732 SIESTA DRIVE |
$3,500,000 | 3/4 |
3,743sf | $935 | Y / Y | A4640849 |
| 5058 WINDWARD AVENUE |
$3,500,000 | 3/3 |
3,471sf | $1,008 | Y / Y | A4667422 |
| 160 GARDEN LANE |
$3,500,000 | 5/4 |
4,086sf | $857 | N / Y | A4663247 |
| 1240 SOLITUDE LANE |
$3,500,000 | 6/4 |
4,699sf | $745 | Y / Y | A4655955 |
| 1253 N BASIN LANE |
$3,499,000 | 4/4 |
3,464sf | $1,010 | Y / Y | A4668457 |
| 4185 ROBERTS POINT LOT 18 CIRC |
$3,400,000 | 5/5 |
3,200sf | $1,062 | N / Y | A4669711 |
| 6532 PEACOCK ROAD |
$3,295,000 | 4/4 |
2,645sf | $1,246 | Y / Y | A4660324 |
| 300 GARDEN LANE |
$3,250,000 | 4/4 |
3,256sf | $998 | Y / Y | A4662830 |
| 7401-B MIDNIGHT PASS ROAD |
$3,250,000 | 4/4 |
2,735sf | $1,188 | N / Y | A4622370 |
| 4903 COMMONWEALTH DRIVE |
$3,250,000 | 4/4 |
3,146sf | $1,033 | N / Y | A4643229 |
| 428 SIESTA DRIVE |
$3,200,000 | 2/2 |
2,163sf | $1,479 | Y / N | A4661294 |
| 276 ISLAND CIRCLE |
$3,100,000 | 4/3 |
2,292sf | $1,353 | Y / Y | A4667090 |
| 910 SIESTA KEY PLACE |
$3,000,000 | 5/4 |
4,201sf | $714 | Y / Y | A4670452 |
| 5246 AVENIDA DEL MARE |
$2,995,000 | 0/ |
3,206sf | $934 | Y / Y | A4668272 |
| 126/128 AVENIDA VENECCIA |
$2,950,000 | 5/4 |
3,260sf | $905 | N / N | A4673661 |
| 5236 SIESTA COVE DRIVE |
$2,950,000 | 4/4 |
4,254sf | $693 | Y / Y | A4640398 |
| 238 ISLAND CIRCLE |
$2,900,000 | 4/4 |
2,854sf | $1,016 | Y / Y | A4650032 |
| 5331 SIESTA COVE DRIVE |
$2,850,000 | 3/3 |
3,795sf | $751 | N / Y | A4628363 |
| 6924 BOCHI CIRCLE |
$2,800,000 | 4/4 |
2,970sf | $943 | N / Y | A4643560 |
| 4757 HIGEL AVENUE |
$2,750,000 | 4/3 |
3,232sf | $851 | Y / Y | A4669548 |
| 105 ISLAND CIRCLE |
$2,730,950 | 4/3 |
2,750sf | $993 | N / Y | A4647817 |
| 430 ISLAND CIRCLE |
$2,695,000 | 5/3 |
3,205sf | $841 | N / Y | A4660296 |
| 4508 WOODSIDE ROAD |
$2,690,000 | 3/2 |
2,238sf | $1,202 | Y / Y | A4674684 |
| 6913 BOCHI CIRCLE |
$2,675,000 | 0/ |
2,729sf | $980 | N / Y | A4668440 |
| 5019 COMMONWEALTH DRIVE |
$2,554,250 | 4/4 |
2,735sf | $934 | N / N | A4630299 |
| 5012 HIGEL AVENUE |
$2,550,000 | 4/3 |
3,541sf | $720 | Y / Y | A4658844 |
| 5024 COMMONWEALTH DRIVE |
$2,500,000 | 3/3 |
2,468sf | $1,013 | Y / Y | A4649919 |
| 1248 NORTHPORT DRIVE |
$2,500,000 | 4/3 |
3,250sf | $769 | Y / Y | A4668459 |
| 25 LANDS END LANE |
$2,500,000 | 0/ |
2,620sf | $954 | N / Y | A4668034 |
| 7665 SANDERLING ROAD |
$2,447,000 | 3/3 |
2,766sf | $885 | Y / Y | A4622464 |
| 6937 MIDNIGHT PASS ROAD |
$2,300,000 | 4/3 |
2,941sf | $782 | Y / Y | A4662450 |
| 518 VENICE LANE |
$2,295,000 | 3/3 |
2,676sf | $858 | Y / Y | A4672419 |
| 5624 CAPE LEYTE DRIVE |
$2,249,000 | 5/5 |
3,126sf | $719 | N / Y | A4670620 |
| 5361 SIESTA CT |
$2,249,000 | 4/2 |
2,774sf | $811 | N / Y | TB8455948 |
| 462 ISLAND CIRCLE |
$2,240,000 | 3/2 |
1,670sf | $1,341 | Y / Y | A4641791 |
| 513 VENICE LANE |
$2,199,000 | 5/3 |
3,009sf | $731 | Y / Y | A4671178 |
| 5334 CALLE FLORIDA |
$2,170,000 | 4/3 |
2,838sf | $765 | N / Y | A4676260 |
| 116 GARDEN LANE |
$2,150,000 | 4/3 |
2,971sf | $724 | N / N | A4671064 |
| 4817 OCEAN BOULEVARD |
$2,149,000 | 4/3 |
2,657sf | $809 | Y / Y | A4671593 |
| 5569 CONTENTO DRIVE |
$2,099,000 | 2/2 |
1,772sf | $1,185 | Y / Y | A4670108 |
| 7221 PLOVERS WAY |
$2,000,000 | 3/3 |
2,748sf | $728 | N / Y | A4675508 |
| 2 ISLAND CIRCLE |
$1,999,999 | 5/4 |
3,855sf | $519 | Y / Y | A4662842 |
| 681 AVENIDA DE MAYO |
$1,999,900 | 3/3 |
3,324sf | $602 | Y / Y | A4652166 |
| 746 PLYMOUTH STREET |
$1,800,000 | 0/ |
2,185sf | $824 | N / Y | A4639522 |
| 4922 COMMONWEALTH DRIVE |
$1,795,000 | 0/ |
2,767sf | $649 | Y / Y | A4666313 |
| 5348 SHADOW LAWN DRIVE |
$1,795,000 | 3/3 |
2,477sf | $725 | Y / Y | A4676391 |
| 4931 OXFORD DRIVE |
$1,725,000 | 3/3 |
3,357sf | $514 | Y / Y | A4620752 |
| 5512 AVENIDA DEL MARE |
$1,695,000 | 4/5 |
3,680sf | $461 | N / N | A4671246 |
| 156 SIESTA DRIVE |
$1,649,000 | 0/ |
2,901sf | $568 | N / Y | A4661717 |
| 763 SIESTA DRIVE |
$1,599,000 | 4/3 |
2,294sf | $697 | N / N | A4648764 |
| 3455 ANGLIN DRIVE |
$1,589,900 | 3/3 |
2,558sf | $622 | N / Y | A4673758 |
| 749 TROPICAL CIRCLE |
$1,575,000 | 4/2 |
2,598sf | $606 | N / Y | A4673529 |
| 111 FAUBEL STREET |
$1,575,000 | 3/3 |
2,214sf | $711 | Y / N | A4669276 |
| 5560 SHADOW LAWN DRIVE |
$1,549,000 | 4/3 |
2,124sf | $729 | Y / Y | A4636955 |
| 5169 OXFORD DRIVE |
$1,500,000 | 3/3 |
1,658sf | $905 | N / Y | V4943078 |
| 854 NORSOTA WAY |
$1,499,000 | 2/2 |
1,667sf | $899 | N / Y | A4665123 |
| 521 CUMMINGS STREET |
$1,495,000 | 3/2 |
2,500sf | $598 | Y / Y | A4667165 |
| 4114 ROBERTS POINT CIRCLE |
$1,495,000 | 4/3 |
2,165sf | $691 | Y / N | A4661864 |
| 1136 SEASIDE DRIVE |
$1,495,000 | 4/2 |
1,249sf | $1,197 | N / N | A4675912 |
| 5341 SIESTA COURT |
$1,450,000 | 3/2 |
1,902sf | $762 | N / Y | A4671562 |
| 3721 FLAMINGO AVENUE |
$1,395,000 | 3/3 |
2,628sf | $531 | Y / N | A4667437 |
| 627 AVENIDA DEL NORTE |
$1,379,000 | 3/4 |
1,713sf | $805 | N / Y | A4655676 |
| 8555 HERON LAGOON CIRCLE |
$1,375,000 | 3/3 |
1,783sf | $771 | N / N | A4646820 |
| 445 REID STREET |
$1,365,000 | 3/2 |
1,750sf | $780 | N / Y | A4671563 |
| 5502 SHADOW LAWN DRIVE |
$1,295,000 | 0/ |
2,337sf | $554 | Y / N | A4649470 |
| 5354 CALLE FLORIDA |
$1,250,000 | 4/3 |
2,659sf | $470 | N / N | A4664418 |
| 5244 WINDING WAY |
$1,250,000 | 4/4 |
2,100sf | $595 | N / Y | A4669581 |
| 5432 CAPE LEYTE DRIVE |
$1,199,000 | 3/2 |
1,659sf | $723 | N / N | A4649500 |
| 4830 ESTRADA DE COSTA |
$1,180,000 | 3/3 |
2,522sf | $468 | Y / Y | A4666867 |
| 5453 AVENIDA DEL MARE |
$1,150,000 | 3/3 |
1,510sf | $762 | N / N | A4669037 |
| 783 BIRDSONG LANE |
$1,150,000 | 0/ |
1,905sf | $604 | N / Y | A4670796 |
| 567 VENICE LANE |
$1,150,000 | 4/2 |
1,915sf | $601 | N / Y | A4670981 |
| 5385 AVENIDA DEL MARE |
$1,100,000 | 4/3 |
2,956sf | $372 | N / Y | A4676293 |
| 310 AVENIDA MILANO |
$1,100,000 | 3/2 |
1,582sf | $695 | Y / N | A4653913 |
| 8234 MIDNIGHT PASS ROAD |
$1,100,000 | 3/2 |
1,758sf | $626 | Y / Y | A4654399 |
| 5036 HIGEL AVENUE |
$1,100,000 | 3/2 |
1,898sf | $580 | Y / N | TB8459412 |
| 4117 ROBERTS POINT CIRCLE |
$1,099,000 | 3/2 |
2,168sf | $507 | N / N | A4640938 |
| 5151 SAINT ALBANS AVENUE |
$1,095,000 | 4/3 |
2,314sf | $473 | N / Y | A4666929 |
| 630 VENICE LANE |
$1,000,000 | 4/2 |
1,859sf | $538 | N / N | A4669940 |
| 226 OGDEN STREET |
$1,000,000 | 2/2 |
1,559sf | $641 | N / Y | A4668141 |
Siesta Key Homes for Sale | Luxury Real Estate in Sarasota
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.
