Siesta Key Homes with Deed Restrictions Community Features

Siesta Key Homes with Deed Restrictions Community Features

Welcome to Siesta Key, Florida—a picturesque barrier island nestled in Sarasota County, renowned for its pristine beaches and vibrant community spirit. With its powdery white sands, Siesta Key Beach consistently ranks among the top beaches in the United States, attracting sun-seekers and nature enthusiasts alike. The island boasts a charming blend of laid-back coastal living and an array of recreational activities, from kayaking in the crystal-clear waters to enjoying sunset strolls along the shoreline.

Siesta Key is not just about stunning beaches; it’s a thriving community where residents enjoy a unique lifestyle enriched by local boutiques, delightful eateries, and an active arts scene. The island’s vibrant nightlife and cultural offerings ensure that there’s always something to do, whether you’re dining under the stars or attending a local festival.

For those considering a home in this idyllic setting, the homes with deed restrictions in Siesta Key offer a perfect blend of luxury and community standards. These thoughtfully designed neighborhoods prioritize aesthetics and maintain property values, ensuring that each residence complements the island’s natural beauty. Residents can enjoy well-maintained common areas, enhanced privacy, and a sense of belonging within a close-knit community.

Whether you’re looking for a cozy beach cottage or an upscale waterfront property, Siesta Key’s deed-restricted communities provide a secure and harmonious environment. Embrace the coastal lifestyle and discover your dream home in this enchanting paradise where the sun shines bright and the waves beckon.

Newest Siesta Key Homes with Deed Restrictions Community Features

40 Sandy Cove Road Unit 4C, Sarasota
$899,999
3 Beds ⋅ 2 Baths ⋅ Sandy Cove SubDv. ⋅ 34242 Zip Code
Private deeded beach access, peaceful pond views, and a location just a short distance from Siesta Key Village create an inviting island lifestyle. Set on a cul-de-sac, this three-bedroom, two-bath end-unit townhome pairs a secluded setting, generous outdoor living spaces, and extensive recent updates. An open-air atrium forms the heart of the home, bringing natural light into the surrounding interiors and creating a private setting for morning coffee or dinner beneath the stars. The galley kitchen, opened up in 2016, connects with this welcoming courtyard and features newer appliances. Beyond the living spaces, a covered lakeside terrace offers a beautiful place to unwind, with tropical landscaping and reflections across the water. The entire upper level is devoted to the primary suite, providing a spacious retreat with a redesigned bath featuring a freestanding soaking tub. Sliding glass doors from both the bedroom and bathroom open to outdoor decks, extending the suite into the island air. Multiple balconies and a sun deck offer additional spaces to relax and enjoy the surroundings. Recent improvements include a new roof in 2025; tile flooring, a four-ton HVAC system and air handler, a water heater, and a tankless hot-water unit serving the primary bathroom. Additional updates include recently replaced upstairs windows, hurricane-rated sliding glass doors installed approximately four years ago, new toilets, and a new downstairs bath vanity. In-unit laundry, ample storage, a one-car garage, and additional parking add everyday convenience, while beautiful landscaping, landscape lighting and irrigation complement the outdoor setting. Sandy Cove’s private deeded beach and fishing pier bring the waterfront experience close to home, while the restaurants, boutiques, and local flavor of Siesta Key Village are an easy walk away. From quiet mornings beside the pond to evenings in the Village, this residence offers a distinctive and personal way to experience life on Siesta Key. All information provided by the sellers is deemed reliable but is not guaranteed. Buyers are encouraged to verify all information independently.

40 Sandy Cove Road Unit 4C, Sarasota

1001 Point Of Rocks Road Unit 207, Sarasota
$1,599,900
3 Beds ⋅ 2 Baths ⋅ Siesta Sands Resort (Timeshare) SubDv. ⋅ 34242 Zip Code
Gulf views from the primary bedroom, or step onto your attached patio with your morning coffee and watch the water come alive. This completely renovated 3 bedroom, 2 bath townhome style condo is turn key and furnished, with an open split floor plan and natural Florida sunlight throughout. The renovation is top to bottom: plank tile floors, solid wood cabinetry, marble countertops, upgraded backsplash, barely used appliances, fresh paint, fully renovated baths with custom tile, new hardware, and new lighting throughout. All windows, doors, and sliders are hurricane impact. Three patios let you soak up the Florida sunshine and Gulf breezes, with the residence facing the pool and open to full Gulf views. Extras include air conditioned storage off the patio, a large laundry room, and an assigned carport with storage and electric hookup. This gated resort offers private beach access, two heated pools, a poolside gazebo with BBQ grills, a lounge area, a fitness room, and high speed WiFi. Walk the sand to Point of Rocks to snorkel and fish, bike to nearby shops and restaurants, or hop the free island trolley to Siesta Key Village. One of the island’s top performing rental communities, with short term rentals allowed (3 day minimum), an on site office, or your own rental service. On site management reports that 3 bedroom units in the community rent for approximately $6,000 per week at the height of season. Rental rates are not guaranteed and are subject to change. A private beachside retreat, a seasonal escape, or a legacy asset to hold and pass down. Bring your flip flops.

1001 Point Of Rocks Road Unit 207, Sarasota

925 Beach Road Unit 208, Sarasota
$565,000
2 Beds ⋅ 1 Baths ⋅ La Siesta SubDv. ⋅ 34242 Zip Code
Enjoy the island lifestyle at La Siesta, ideally located directly across from world-famous Siesta Key Beach! This inviting, turnkey-furnished, two-bedroom, second-floor condominium is situated in highly desirable Building B, known for its close proximity to the beach. With a 7-day minimum rental policy and convenient on-site rental management, La Siesta offers the best of both worlds, your own beach getaway with the added benefit of generating rental income when you're not enjoying it yourself! Thoughtful recent improvements include new carpeting (2026), a beautifully resurfaced lanai (2026), a new air conditioning system and water heater (2025), an updated electrical panel (2024), and newer appliances (2024). The kitchen was also renovated by a previous owner. The private screened-in lanai provides a wonderful space to relax and unwind while enjoying the refreshing coastal breezes. Adding even more appeal, La Siesta has benefited from recent community-wide improvements, including exterior painting (2026), further enhancing this desirable beachside destination. Residents and guests enjoy an array of resort-style amenities, including a heated community pool, fitness center, clubhouse, grilling areas, and convenient on-site laundry facilities. In addition, the condominium includes one assigned carport parking space and a storage locker for your beach toys. Enjoy the ultimate peace of mind, whether you live near or far, with professional on-site management handling everything from cleaning and guest check-ins and check-outs to responsive maintenance and everyday needs, you can enjoy the benefits of ownership without the day-to-day responsibilities. Just across the street, you'll love the powdery white sands and breathtaking sunsets of Siesta Key Beach! You're also close to the charming boutiques, restaurants, and entertainment of Siesta Key Village, with convenient access to the mainland via the Stickney Point Bridge plus a free trolley that stops in front of La Siesta to get you anywhere on the island. This exceptional location puts the best of island living right at your fingertips. Whether you're seeking your own coastal escape or an opportunity to generate rental income, this well-maintained condominium offers the perfect combination. Your slice of Siesta Key paradise awaits!

925 Beach Road Unit 208, Sarasota

84 Avenida Veneccia Unit 201, Sarasota
$5,995,000
3 Beds ⋅ 3 Baths ⋅ 89 Beach SubDv. ⋅ 34242 Zip Code
Set behind private entry gates and situated on one of the most beautiful beaches in the world, you will find the boutique building known as 89 Beach. A community of just six modern condominium residences, this building exudes style, chic architecture, and a unique and coveted location with easy beach access and proximity to all the amenities of Siesta Key Village. Unit 201 is a special offering- this two-story townhome lives almost like a single- family home paired with all the convenience of a condominium living. After entering onto the private gated property, residents will enjoy an oversized, enclosed two car garage with abundant storage located directly beneath the townhome and directly adjacent to the elevator which has a private secure entry to both townhome levels. Directly adjacent to the private garage is a deeded beach cabana for enjoying beach days in style and shade. This residence has been masterfully designed and furnished with every detail being taken into account to create a masterpiece ready for a new owner. Upon entering this residence you will notice superior detailing including tile floors throughout, recessed wood ceiling details, a magnificent floating staircase and wavy wall, and tons of natural light flowing in through the floor-to-ceiling impact glass windows and sliding doors. Each of the two levels has its own terrace with sights and sounds of the Gulf. This residence comes fully equipped with a smart home Control4 system, Lutron lighting system, built-in surround sound, automated recessed shades and so much more. The kitchen features custom wood cabinetry, Gaggenau appliances, natural gas range, and breakfast bar seating for entertaining. The main living area feels like you are sitting on the beach with a built-in fireplace for cool coastal nights and fantastic views. The second level contains all the bedrooms, and this primary bedroom is a true show-stopper! Imagine opening the black shades from your beachfront bed set in the middle of the room and watching the day come to life. The suite offers dual walk-in closets with built-ins, and spa like primary bath including a steam shower, and even a built-in coffee bar. Your guests will never want to leave the well-appointed guest bedrooms which offer great light and space- one of the guest bedrooms even has access the balcony. 89 Beach features an elevated resident’s heated pool with seating and fire pit for entertaining. This truly unique location differs from so many other barrier island condominiums due to its access to restaurants, nightlife, groceries, and shopping within a block or two. Come to enjoy 89 Beach, with the convenience of its location and luxury, you may never want to leave. Schedule your private showing today.

84 Avenida Veneccia Unit 201, Sarasota

8900 Blind Pass Road Unit A303, Sarasota
$799,900
1 Beds ⋅ 1 Baths ⋅ Fishermans Cove SubDv. ⋅ 34242 Zip Code
Top-floor, turnkey beachfront living with your own assigned boat slip—experience the best of both worlds on the quiet southern end of world-renowned Siesta Key in Sarasota, Florida. Breathtaking Gulf views greet you from every room of this beautifully remodeled 1-bedroom, 1-bathroom condo, where tranquil turquoise waters and a beachfront setting create an extraordinary coastal retreat. An enclosed patio with hurricane-impact windows offers a cruise-ship-like perspective over the Gulf. Open the windows to welcome coastal breezes and the soothing sound of waves along the shore. With the Gulf on one side and Blind Pass Lagoon on the other, enjoy both sunrise and sunset, sand between your toes, and boating adventures from your assigned slip. Launch a kayak or paddleboard to explore the waterways, or head out by boat toward Sarasota Bay and the open Gulf with no bridges along the way. Thoughtfully remodeled throughout, the interior features ceramic wood-look tile, soft coastal colors, updated fans and light fixtures, and an open floor plan designed to showcase the views. The beautifully renovated kitchen features granite countertops, custom wood cabinetry with soft-close doors, a tile backsplash, and stainless steel appliances. An opened kitchen wall enhances sightlines, while an additional glass door brings in views of Blind Pass Lagoon, where wildlife, kayakers, and boaters provide an ever-changing backdrop. Beautifully appointed furnishings complement inviting spaces for dining and entertaining, including a kitchen breakfast bar, a full dining area, and additional dining space on the enclosed patio. Thoughtful furniture with built-in storage and an additional interior closet provide room for beach essentials. Wake to water views in the primary bedroom, complete with an expansive walk-in closet housing a full-size washer and dryer—a rare convenience in this community for owners and renters alike. The thoughtfully renovated bathroom features a glass-enclosed walk-in shower, an updated vanity with a granite countertop, and updated lighting. Additional highlights include air conditioning updated in 2023 and a new building roof in 2025. Monthly fees include water, sewer, internet, and cable. Enjoy long beach walks, a heated community swimming pool, boating, kayaking, and fishing—all at your fingertips. Walk to waterfront dining at Turtles Restaurant and Ophelia’s on the Bay, or take the free trolley to Siesta Key Village for dining, live entertainment, and charming shops. Discover downtown Sarasota’s cultural offerings, including ballet, symphony performances, the Van Wezel Performing Arts Hall, and the farmers market, with convenient access to Sarasota Bradenton International Airport. Whether you seek a turnkey beachfront escape, an investment opportunity with one-week minimum rentals, or a full-time coastal residence, this exceptional Fishermans Cove condo brings together beachfront beauty and a bonus boating lifestyle if desired!

8900 Blind Pass Road Unit A303, Sarasota

5534 Cape Leyte Drive, Sarasota
$1,549,000
3 Beds ⋅ 4 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
LOCATION, LOCATION, LOCATION!!! STEPS TO THE BEACH....YOUR FURNISHED SIESTA KEY ESCAPE—BEAUTIFULLY REIMAGINED This extensively and tastefully renovated 3 bedroom, 3 and 1 half bath with quality finishes throughout has been meticulously maintained and is being offered furnished. This 2300 square feet under air, a 2 car garage and large pool with panoramic screened cage residence welcomes you with tropical landscaping, a circular paver driveway, and an inviting island style. Renovated in 2017–2018 this home offers a relaxed living space that with substantial improvements throughout. Each bedroom features its own private en suite bathroom, complemented by a separate guest half bath. All bathrooms were completely redone during the renovation. Improvements included a new metal roof, PGT WinGuard Aluminum 700 Series impact windows throughout, all new doors, plumbing, electrical, air-conditioning and ducts, drywall, lighting, insulation and tile flooring. The kitchen features white cabinetry, a contrasting island with seating, and an impressive appliance selection: a Thermador gas stove and oven/microwave combination, Bosch dishwasher, and Café refrigerator. A 250-gallon propane tank supplies the gas stove and tankless water heater. Open living and dining spaces provide a welcoming setting for entertaining, with warm-toned tile flooring and views of the surrounding greenery. Outside, the pool, paver deck, and lanai invite relaxed outdoor living. A Panoramic View pool enclosure enhances the outlook, creating a beautiful setting for morning coffee, poolside dining, and quiet afternoons. Additional conveniences include central vacuum throughout the home, wiring for ceiling fans in every room, and an oversized two-car garage. Thoughtfully updated with quality finishes throughout, this welcoming Siesta Key retreat is ready for your next chapter of island living.

5534 Cape Leyte Drive, Sarasota

1207 Sharswood Lane, Sarasota
$3,195,000
3 Beds ⋅ 4 Baths ⋅ Spice Bay SubDv. ⋅ 34242 Zip Code
LIVE THE SIESTA KEY LIFESTYLE IN SPICE BAY—an intimate, gated enclave of just 14 estate-sized homesites in one of Siesta Key’s most distinctive Intracoastal communities. Custom built by award-winning builder Ryan Perrone of Nautilus Homes, this sophisticated residence offers approximately 3,235 square feet of beautifully designed SINGLE-LEVEL LIVING with exceptional craftsmanship, privacy, and effortless indoor-outdoor entertaining. Offered FURNISHED, this exceptional home is ready for you to immediately begin enjoying the Siesta Key lifestyle. From the moment you enter through the impressive mahogany front door, a dramatic wall of glass sliders draws your eye to the lush tropical surroundings and expansive outdoor living areas beyond. Filled with NATURAL LIGHT, the home blends refined finishes with relaxed “barefoot elegance,” creating a coastal retreat that feels both luxurious and inviting. The thoughtfully designed floor plan features 3 BEDROOMS, EACH WITH ITS OWN ENSUITE BATH, providing exceptional privacy and comfort for family and guests. The spacious primary suite includes a private den/study and a luxurious spa-inspired bath, while the additional bedrooms are generously sized and beautifully appointed. A PRIVATE CASITA LOCATED JUST OFF THE PORCH adds even more flexibility—perfect for visiting guests, extended family, a private retreat, studio, or home office. Throughout the home, you’ll find wide-plank oil-finished wood flooring, handcrafted details, custom closets and built-ins that reflect the quality of this custom residence. At the heart of the home, the GOURMET CHEF’S KITCHEN was created for entertaining and features a 6-burner gas range, steam oven, two dishwashers, generous workspace and a large walk-in pantry. Open the sliders and embrace true Florida indoor-outdoor living. The extended courtyard and lanai enjoy DESIRABLE SOUTHERN EXPOSURE and a private tropical setting—perfect for morning coffee, entertaining friends, relaxing with an evening cocktail or unwinding in the spa. For boating enthusiasts, enjoy access to a DEEP-WATER BOAT DOCK WITH A 13,000-LB LIFT, making it easy to spend your days exploring Sarasota Bay and the surrounding waterways. An oversized THREE-CAR TANDEM GARAGE provides exceptional space for vehicles, storage and all your island toys. Spice Bay offers the rare combination of PRIVACY AND CONVENIENCE on Siesta Key. Walk or bike to the beach, nearby shops and restaurants, spend your days enjoying the world-famous quartz sands of Siesta Key Beach, then head downtown for Sarasota’s celebrated dining, arts and cultural scene. This exceptional TURNKEY FURNISHED custom residence captures the very best of luxury coastal living—private, refined and unmistakably Siesta Key.

1207 Sharswood Lane, Sarasota

6157 Midnight Pass Road Unit E93, Sarasota
$475,000
2 Beds ⋅ 2 Baths ⋅ Siesta Plat SubDv. ⋅ 34242 Zip Code
Exceptional opportunity on SIESTA KEY! Whether you're searching for a vacation getaway, full-time island residence, or income-producing investment, this TURNKEY 2-bedroom, 2-bath condo at Bay Oaks offers an unbeatable combination of location, flexibility and value. With WEEKLY RENTALS ALLOWED, owners have the freedom to take advantage of Siesta Key's highly desirable vacation rental market while still enjoying the property themselves. Outside rental management and self-management is allowed, providing added flexibility for investors. Located on the third floor, this spacious 1,101 sq. ft. condo is being sold TURNKEY and ready to enjoy from day one. The kitchen has been beautifully renovated creating a fresh, updated space with stainless steel appliances, gorgeous quartz countertops, large island with seating, and coastal backsplash. The open living and dining areas flow onto a screened in balcony overlooking mature tropical landscaping—the perfect spot to enjoy your morning coffee or unwind after a day at the beach. A generous outdoor storage closet provides convenient space for beach chairs, umbrellas and all your island essentials. The split bedroom layout offers privacy for owners and guests, with two spacious bedrooms and two full bathrooms. An IN-UNIT WASHER AND DRYER adds another sought-after convenience for both personal use and vacation rentals. Bay Oaks provides an impressive collection of amenities including a heated community pool, fishing pier along the Intracoastal Waterway, tennis and pickleball courts, BBQ and picnic areas, and covered parking. Leave the car behind and embrace the island lifestyle with the Siesta Key trolley providing convenient transportation to Siesta Key Village, local restaurants, shops, entertainment and Siesta Key's world-famous white-sand beaches. With weekly rentals permitted, flexible management options, turnkey furnishings, a renovated kitchen and an outstanding Siesta Key location, this condo offers an incredible opportunity to own your own piece of paradise while enjoying the potential for vacation rental income. Bring you sunscreen and come experience everything that makes Siesta Key one of Florida's most sought-after island destinations!

6157 Midnight Pass Road Unit E93, Sarasota

8773 Midnight Pass Road Unit 504G, Sarasota
$615,000
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
Welcome home to your tropical retreat at Island Reef on south Siesta Key! Island Reef is a Gulf to Bay resort style community. Amenities include: 2 heated pools, private beach, pickleball, tennis, clubhouse and docks. There is an active social calendar and in-house rental management as well. This beautiful penthouse unit has a wonderful pool and courtyard view. 504G is being offered Turnkey Furnished. This beachy condo has been extensively upgraded including the kitchen, both bathrooms, a laundry with full-size washer and dryer, and a raised ceiling in the dining area. The knotty pine floors and doors are reminiscent of a coastal cottage. Indirect lighting can be dimmed to suite your needs. A new AC was installed in Oct 2026 and the warranty will be transferred to the new owners. The kitchen and bathrooms have solid wood paneled cabinets, granite countertops, and subway tile bath and shower surrounds. In the kitchen the lighted cabinets allow for a beautiful display of dishes, glassware, and favorite collectibles. The living room and dining area have comfortable coastal furniture. The large dining table holds 6-8. Glass sliding doors open to a garden style lanai with slate tile flooring. Enjoy the tropical breeze and pool view while sipping your morning coffee on this wonderful lanai. Throughout the condo there are several unique antique wood chests and other furniture pieces., which are perfect for additional storage. The coastal artwork and knick-knacks are included in the purchase of this home. From the primary bedroom, you can also access the lanai through sliding glass doors. There is a large walk-in closet and an ensuite bathroom with dual sinks and large shower. The guest bedroom has a three-piece full wall shelving /desk unit. There is also a full wall built-in closet. Across the hallway is a laundry and storage room. If you are ready to make a move to paradise, please call for a private showing. When you see 504G you will fall in love! Buy now and enjoy winter on Siesta Key!

8773 Midnight Pass Road Unit 504G, Sarasota

4712 Ocean Boulevard Unit W5, Sarasota
$1,359,000
2 Beds ⋅ 2 Baths ⋅ Windward Passage SubDv. ⋅ 34242 Zip Code
Virtually Staged - Perfectly positioned to capture the ever-changing beauty of the Gulf, this northwest-facing residence offers a front-row seat to nature’s daily masterpiece. From the lush green lawn and swaying palm fronds to the Gulf’s ever-changing shades of turquoise, blue, and emerald, the views unfold in layers of coastal color. As the day draws to a close, the western sky ignites in brilliant sunset hues, transforming the landscape into a breathtaking panorama that never looks quite the same twice. Here, the view isn’t just something you see—it’s an experience to savor. Welcome to Windward Passage, where the beauty of Siesta Key meets the comfort of an exceptionally spacious coastal retreat. Offering 1,626 square feet of living space, this two-bedroom, two-bath residence blends timeless Gulf views with thoughtful modern updates. Renovated kitchen and bathrooms, luxury vinyl plank flooring throughout, impact-resistant windows on the waterfront facing side, and a newer air-conditioner provide the perfect balance of style, comfort, and peace of mind. Situated on the third floor, the home enjoys an ideal elevation—high enough to embrace sweeping coastal scenery while maintaining a wonderful connection to the tropical landscape below. An oversized private garage adds a level of convenience and storage rarely found in condominium living. Beyond the residence, the best of Siesta Key is practically at your doorstep. Just a leisurely 10-minute stroll brings you to the heart of Siesta Key Village, where lively tiki bars, exceptional dining, boutique shops, and live music create an atmosphere that’s distinctly island. And when the beach calls, the nearest public beach access lies just beyond "The Village" or an even easier 5-minute bike ride away. Whether you’re seeking a full-time residence or a cherished coastal getaway, this is a place to slow down, settle in, and appreciate the extraordinary beauty of everyday life on Siesta Key. Some properties are defined by their features. Others are remembered for how they make you feel. This one offers both.

4712 Ocean Boulevard Unit W5, Sarasota

6310 Midnight Pass Road Unit 403N, Sarasota
$749,000
2 Beds ⋅ 2 Baths ⋅ Crescent Arms SubDv. ⋅ 34242 Zip Code
Dont Miss this one' beachfront Unit at Crescent Arms on beautiful Siesta Key. Wake up to the sound of gentle waves and step directly onto the powdery white sands of world-renowned Siesta Key Beach from this beautifully fourth floor unit. Perfectly positioned for effortless coastal living, this 2-bedroom, 2-bath unit offers Gulf views and a short walk-out to the beach. The open-concept layout is bathed in natural light, featuring a spacious living area that flows seamlessly to the screened lanai, you can enjoy sunsets over the Gulf . This unit was updated several years ago with solid-surface countertops, tiled floors through out and ample storage making it ideal for both full-time living and vacation stays. The primary suite boasts ample room for a king bed which will boost rental income and a private ensuite bath, while the guest bedroom and bath provides comfort and privacy for family or visitors. Crescent Arms offers resort-style amenities, including a heated beachside pool, private beach lounges, grilling area, and gated access for security and peace of mind. Located on Siesta Key, this community is within minutes of Siesta Key Village, shops, restaurants, and island nightlife. Whether you’re seeking a serene retreat, an investment property with excellent rental potential, or your forever beach home, this beachfront gem delivers the ultimate Siesta Key lifestyle. Recent upgrades include new AC system. This unit has a Strong rental history.

6310 Midnight Pass Road Unit 403N, Sarasota

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