Siesta Key Homes with Deed Restrictions Community Features

Siesta Key Homes with Deed Restrictions Community Features

Welcome to Siesta Key, Florida – a slice of paradise nestled in Sarasota County, renowned for its stunning beaches, vibrant culture, and laid-back lifestyle. This idyllic barrier island is a haven for sun-seekers and nature enthusiasts alike, boasting powdery white sands that are consistently ranked among the best in the world. With its charming coastal vibe, Siesta Key invites you to explore its quaint shops, delightful eateries, and lively nightlife, all while basking in the warm Florida sun.

Siesta Key is not just a beautiful destination; it’s also a fantastic place to call home. The community features a range of homes with deed restrictions, ensuring a harmonious living environment that maintains the area’s charm and appeal. These thoughtfully designed neighborhoods often include amenities such as community pools, parks, and walking trails, fostering a sense of community while preserving the natural beauty of the surroundings.

Living in a deed-restricted community means you can enjoy peace of mind, knowing that the aesthetic and operational standards are upheld, making it an ideal choice for families, retirees, and anyone in between. The emphasis on community standards helps maintain property values, ensuring that your investment is safeguarded for years to come.

Whether you’re looking for a cozy beach cottage, a luxurious waterfront estate, or a modern condo with breathtaking views, Siesta Key has something for everyone. Embrace the coastal lifestyle and discover why so many are drawn to this enchanting island. Your dream home awaits in Siesta Key, where every day feels like a vacation!

Newest Siesta Key Homes with Deed Restrictions Community Features

757 Beach Road Unit 310, Sarasota
$950,000
2 Beds ⋅ 2 Baths ⋅ Crescent Royale SubDv. ⋅ 34242 Zip Code
Beautiful gulf views. This unit is situated right across from the public beach and is withing 0.9 miles/3 minutes to the village. This turnkey fully furnished and equipped unit is move in ready. Right thru the front door you are greeted with an open floor plan overlooking the beach and the gulf water views. Smell the salt air as you lounge or dine on your large private screen in patio. The unit offers a beach vibe paint palette well-appointed furnishing and shows ownership pride. As you enter you are greeted with a large kitchen with stainless steel appliances an abundance of cabinets and granite counter tops and a large island. The kitchen is fully stocked and ready for all your cooking needs. Next to the kitchen is a large dining area with a table for 6. The living room also overlooks the beach and water views. It has a large sectional and side chair plenty of room for all your guests. This unit offers a master suite overlooking the gulf with an ensuite full bathroom. The guest room is also a great size and has a full attached bathroom. Both bedrooms have oversized walk-in closets plus a separate owner's closet. The unit also offers luxury vinyl flooring, tile and carpet. Impact patio doors for a piece of mind. The community is gated, and you have an assigned carport for parking. Crescent Royal has a managed onsite weekly rental program. The site offers a heated pool, fitness center, shuffleboard, and a grilling area. Public beach is right across the street. Also, there is Trolley that gives you access to the village or take a short stroll to dining, entertainment, shopping and yes sand dollar picking on the sand bar. This unit is currently in the rental program and has an excellent rental history and future bookings. The gulf is calling don't miss this beautiful beach retreat.

757 Beach Road Unit 310, Sarasota
5860 Midnight Pass Road Unit 38, Sarasota
$650,000
1 Beds ⋅ 1 Baths ⋅ Gulf Haven SubDv. ⋅ 34242 Zip Code
Located in the highly sought-after Gulf Haven Community where residences rarely become available. This beautifully renovated beach getaway offers a rare opportunity to enjoy private beachfront living on the sugar-white sands of world-famous Siesta Key Beach, shared exclusively by just 50 owners. No crowds, no competition for space for your beach chair or blanket, just pure relaxation. With nearly 1,000 square feet of air-conditioned living area, the unit features a brand-new kitchen showcasing stainless steel appliances, shaker-style cabinetry, and elegant quartz countertops. The chef’s kitchen is complemented by an oversized living area with soaring vaulted ceilings and enlarged windows that flood the space with natural light. Porcelain tile runs throughout the residence providing a luxurious feel in every room. The fully renovated bathroom includes a custom glass-enclosed shower, new cabinets, and stunning countertops. Major upgrades such as a new HVAC system and water heater provide peace of mind and leave nothing for an owner to do but enjoy the beach. Additional features include a Florida room, a spacious bedroom with a walk-in closet, second closet, and attic storage. Additionally, there is a fully enclosed carport with ample attic storage, parking for two vehicles, and just a short stroll to the beach. Finally, there is an in-residence laundry room with a full sized washed and dryer, very rare for beach front condominiums. This ground floor residence is ideally located close to the sand while overlooking the lush grassy courtyard that leads directly to the beach. Residents enjoy access to a beachfront club room, community outdoor gathering area, and a sparkling community pool, delivering the ultimate Siesta Key lifestyle that you’ve been waiting for. A short ride to dining, shopping, and non-stop entertainment at either the north or south villages. Come and live the life you deserve in this ultimate beach getaway.

5860 Midnight Pass Road Unit 38, Sarasota
5760 Midnight Pass Road Unit 109, Sarasota
$1,289,000
3 Beds ⋅ 2 Baths ⋅ Gulf N Bay SubDv. ⋅ 34242 Zip Code
Rarely available and highly sought after, this beautifully renovated 3-bedroom, 2-bath residence is one of only a handful of lobby-level condominiums within Gulf & Bay Club. Perfectly positioned to capture expansive water views, the home offers breathtaking vistas from nearly every room, overlooking lush manicured grounds, serene lakes, and beautiful Gulf views stretching toward the horizon. The ever-changing backdrop of water, tropical landscaping, and coastal skies creates a sense of tranquility that is uniquely Gulf & Bay. A comprehensive floor-to-ceiling renovation has transformed the residence into a sophisticated coastal retreat. The living area was thoughtfully expanded to maximize both space and scenery, creating an open, light-filled environment where the spectacular views remain the focal point. With no elevator required and convenient access to the beach, pools, and community amenities, this coveted ground-floor location offers a level of accessibility and ease rarely found on Siesta Key. Lovingly maintained by its owners and never rented, the residence reflects pride of ownership throughout. Behind the beautiful finishes lies an extensive list of meaningful improvements, including impact-resistant windows and doors, a new HVAC system, luxury vinyl plank flooring, custom shades, and newer appliances, including a washer, dryer, garbage disposal, and a beverage/wine cooler at the dining area's dry bar, the perfect spot to prepare sunset cocktails and appetizers before heading out to enjoy another beautiful evening on Siesta Key. Offered turnkey furnished, this condo is ready to be enjoyed from day one. Brand-new La-Z-Boy furnishings enhance the living room, while carefully selected Pottery Barn pieces create a bright, serene atmosphere in the primary suite. The third bedroom features custom built-in cabinetry and provides office space including a full-size bed for guests. The spacious second guest bedroom comfortably accommodates two queen-size beds and includes built-in storage designed to maximize both function and comfort. Gulf & Bay Club offers a true resort-style experience set along 800 feet of private beachfront on world-famous Siesta Key Beach. Residents enjoy a beautifully maintained, gated community with on-site maintenance and an exceptional array of amenities, including three heated swimming pools, tennis and pickleball courts, fitness facilities, saunas, two clubhouses, beach chair service, and recently updated landscaping, fencing, beach enhancements, electric charging stations and grilling areas. Surrounded by tropical landscaping, scenic lakes, fountains, and winding pathways, Gulf & Bay delivers the atmosphere of a luxury coastal resort while offering the comfort and convenience of home. Location is key here, so close to shopping, dining, downtown Sarasota, the airport, and so much more! Need to head to Siesta Key Village for some fun? Hop on the free trolley; your possibilities are endless! Whether you're seeking a full-time residence or a seasonal escape, this exceptional property offers a rare combination of panoramic water views, extensive upgrades, turnkey convenience, and an unmatched Siesta Key lifestyle.

5760 Midnight Pass Road Unit 109, Sarasota
3936 Hamilton Club Circle Unit 6, Sarasota
$1,400,000
3 Beds ⋅ 4 Baths ⋅ Hamilton Club SubDv. ⋅ 34242 Zip Code
Siesta Key,exclusive gated community of only 18 homes with deep water marina,pool, and tennis court all within a private, lush, tropical paradise . Walking paths around a central lagoon , as well as a beautifully maintained boardwalk of Ipe wood bordered with mangroves , are among the things that make Hamilton Club so very special . Inspired by the architecture of Bermuda with its close ties to 17th Century Great Britian is recognized by its striking pastel colored walls and "welcoming arms"staircases . Very close to the Village and Crescent Beach yet equally convenient to Downtown Sarasota. This sophisticated townhome has been renovated with fine finishes , wood and stone are incorporated in a wonderfully artistic way. Soaring ceilings and a Southern exposure provide amazing ,cheerful lighting . Fabulous center island in a truly stunning kitchen with expansive counter space, premium appliances and elegant custom cabinetry .Large walk in pantry .

3936 Hamilton Club Circle Unit 6, Sarasota
6157 Midnight Pass Road Unit E24, Sarasota
$474,000
1 Beds ⋅ 1 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code
Elevated living awaits in this beautifully appointed 4th-floor condo, located just minutes from the quartz sands of Siesta Key Beach. This turn-key residence offers a seamless blend of relaxed Florida style and incredible investment potential. The bright, airy interior is flooded with natural light, leading out to an east-facing screened balcony that overlooks lush, tropical landscaping. This condo features durable ceramic tile flooring throughout the main living areas, a well-equipped kitchen with stainless steel appliances, and a generous walk-in pantry. Storage is effortless thanks to a separate large closet designed to house all your beach and pool gear. Recent mechanical updates, including a brand-new water heater and a newer A/C system, for greater peace of mind. Positioned as a premier vacation destination, this property allows for weekly rentals, offering a fantastic opportunity to offset ownership costs with gross rental income ranging from $30,000 to $40,000 annually. Residents enjoy access to a resort-style community pool, tennis courts, a social room, and a fishing pier. The unit includes one assigned covered parking space along with ample guest parking. Whether you are looking for a personal getaway or a high-performing rental, this condo delivers the ultimate coastal lifestyle.

6157 Midnight Pass Road Unit E24, Sarasota
8773 Midnight Pass Road Unit 302G, Sarasota
$500,000
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
WELCOME TO PARADISE AT ISLAND REEF! This beautiful condo at 8773 Midnight Pass Road, Unit 302-G, is your opportunity to experience the ultimate Siesta Key lifestyle! Located in the desirable Island Reef community, this incredible Gulf-to-Bay property offers the perfect combination of island charm, relaxation, and resort-style living. Enjoy an amazing selection of community amenities, including two heated swimming pools, private beach access, tennis and pickleball courts, a fitness center, clubhouse, game room, library, shuffleboard, boat docks, fishing pier, kayak launch, and grilling areas! There's always something to enjoy, whether you're soaking up the Florida sunshine, getting out on the water, staying active, or simply relaxing with friends and neighbors. And the location? Absolutely fantastic! Just moments from beautiful beaches, wonderful restaurants, shopping, parks, and everything that makes Siesta Key one of Florida's most desirable destinations. Whether you're searching for your forever home, a seasonal escape, or your own tropical getaway, this is an opportunity to make those Florida dreams come true. At Island Reef, every day feels like a vacation! Come see why you'll want to call this incredible community HOME!

8773 Midnight Pass Road Unit 302G, Sarasota
1300 N Portofino Drive Unit 102, Sarasota
$449,995
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
THE SIESTA KEY LIFESTYLE, ALL IN ONE EXCEPTIONAL WATERFRONT COMMUNITY! Imagine starting your day with coffee overlooking a picturesque harbor, spending the afternoon with your toes in Siesta Key’s powdery white sand, and gathering with friends for sunset cocktails as another spectacular Florida day draws to a close. Welcome to Siesta Harbor Condominiums Association, a vibrant 55+ community where boating, beach days, and an inviting social scene come together in one extraordinary island setting. DIRECT WATERFRONT LIVING! Perfectly positioned on the ground floor, this beautifully updated, fully furnished 2-bedroom, 2-bath residence feels more like a private coastal home than a condo. Forget elevators and stairs - simply walk through your front door with groceries or beach bags and you’re home! Inside, a bright, breezy interior features attractive tile floors throughout and an open layout designed for easy entertaining. The remodeled kitchen is a showpiece, with gorgeous granite countertops, crisp white cabinetry, stainless steel appliances, a stylish glass backsplash, a generous breakfast bar opening to the living room, and the everyday luxury of a KITCHEN PANTRY—all with gorgeous views of the harbor! The living room flows into a spectacular glass-enclosed lanai, where walls of impact-resistant glass sliders frame intimate views of the harbor, lush tropical grounds, and boats gently resting along the waterway just beyond your windows. Imagine lingering here with a good book, watching the boats drift by, or savoring an evening cocktail in your own waterfront retreat. Two welcoming bedrooms include a flexible guest room with a Murphy bed, ideal for visitors or a home office. Updated bathrooms include a bidet toilet in the primary suite. Impact glass, tasteful furnishings, a private LOCKED STORAGE CAGE just down the hall, and on-site laundry and covered parking are welcome perks. Beyond your front door, the Florida lifestyle unfolds! Boaters will love the harbor's DIRECT INTRACOASTAL WATERWAY ACCESS WITH NO BRIDGES, situated just north of the South Bridge no-wake zone for convenient cruises south toward Venice. Imagine stepping aboard your boat just outside your home and setting off for a day on the water (slips subject to availability). Beach lovers will treasure DEEDED BEACH ACCESS directly across the street at Crescent Arms, opening the door to Siesta Key’s world-famous white quartz sand and sparkling Gulf waters. Spend sun-drenched afternoons by the community pool, relax in the hot tub, or enjoy the clubhouse, fitness center, library, billiards, and lively social activities. One of Siesta Harbor’s most cherished traditions is sunset happy hour on the waterfront sunset deck, where neighbors gather to toast another beautiful evening in paradise. Tucked into a peaceful waterfront setting, Siesta Harbor is just moments from South Siesta Key Village, with its grocery store, restaurants, bars, and charming boutiques. The nearby South Bridge makes mainland Sarasota wonderfully accessible, while the Breeze transit stops right in front of the clubhouse for a convenient way to explore the island. Whether your perfect day means cruising the Intracoastal, strolling the beach, sharing sunset cocktails, or simply relaxing beside the water, this is more than a condominium—it’s your invitation to live the SIESTA KEY LIFESTYLE you’ve always imagined! WHERE ELSE can you enjoy waterfront living and resort-style amenities under $500K on Siesta Key?

1300 N Portofino Drive Unit 102, Sarasota
6287 Midnight Pass Road Unit 106, Sarasota
$630,000
2 Beds ⋅ 2 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code
PRICED $30,000 LESS THAN LAST APPRAISAL REPORT (May 2026). Enjoy the best of the Siesta Key lifestyle at Excelsior Beach to Bay! This beautifully appointed 2-bedroom, 2-bath condominium features new plank tile flooring throughout the main living areas, with traditional tile flooring in both bathrooms. Hurricane-impact windows provide additional piece of mind. Residents enjoy deeded access to world-famous Siesta Key Beach, along with beautifully maintained tropical grounds and an impressive array of resort-style amenities. Relax by either of the two community pools, stay active on the tennis and pickleball courts, or take advantage of the fitness center, shuffleboard and outdoor grilling stations. Additional amenities include a community room, library and convenient on-site management. Each building offers assigned covered parking with ample additional parking for guests. An additional storage unity provides convenient space for beach chairs, bicycles, and all you beach essentials. Whether you're looking for a full time residence, a seasonal getaway, or an investment opportunity, Excelsior offers exceptional flexibility. Ideally located near Siesta Key's beautiful beaches, popular restaurants, shopping and entertainment, this is an opportunity to enjoy the very best of coastal Florida living!

6287 Midnight Pass Road Unit 106, Sarasota
1200 Cove Ii Place Unit 832, Sarasota
$549,900
2 Beds ⋅ 2 Baths ⋅ Midnight Cove Ii SubDv. ⋅ 34242 Zip Code
Turnkey 2BR/1.5BA Condo with Stunning Water Views – Steps from Crescent & Siesta Beaches! Welcome to your slice of paradise! This beautifully maintained 2-bedroom, 1.5-bath condo sits on the 3rd floor, directly across from the sugar sands of Crescent Beach and just a short stroll to world-famous Siesta Beach. Enjoy breathtaking views overlooking the marina and Intracoastal Waterway from your private balcony—perfect for morning coffee or sunset cocktails. Located in the highly sought-after Midnight Cove II, this community offers a vibrant coastal lifestyle with low maintenance fees that include Cable TV and Fiber Internet. No special assessments or surprises here as the community maintains fully funded reserves and passed the milestone inspection without missing a beat. Whether you're lounging at the heated pool, hitting the tennis, pickleball, or basketball courts, or simply soaking up the community vibe, there's something for everyone here. Offered turnkey furnished and priced to sell, this is a rare opportunity to own in one of the area's most desirable waterfront communities. Don't miss your chance to live the beach life or invest in a prime rental property!

1200 Cove Ii Place Unit 832, Sarasota
9203 Midnight Pass Road Unit 2, Sarasota
$1,895,000
3 Beds ⋅ 3 Baths ⋅ Siesta Bayside SubDv. ⋅ 34242 Zip Code
SIESTA KEY WATERFRONT LIVING WITH BRAND-NEW PRIVATE DOCK, 16,000-LB BOAT LIFT, AND INTRACOASTAL WATERWAY VIEWS! Discover the ultimate coastal lifestyle at 9203 Midnight Pass Road, a beautifully renovated three-bedroom, two-and-a-half-bath waterfront residence ideally situated on the peaceful southern end of Siesta Key, just a short walk from Turtle Beach. Combining stylish interiors, exceptional boating amenities, and an unbeatable island location, this inviting retreat offers the perfect blend of comfort, convenience, and waterfront living. Thoughtfully updated throughout, the residence features a beautifully remodeled kitchen with contemporary finishes, renovated bathrooms, and comfortable living spaces designed for both everyday enjoyment and effortless entertaining. Two enclosed lanais provide an additional 356 square feet of versatile space, creating inviting areas to relax, entertain, or simply take in the tranquil Intracoastal Waterway views. For boating enthusiasts, this property truly shines. A brand-new private deep-water dock and newly installed 16,000-pound boat lift offer outstanding convenience and direct access to the Intracoastal Waterway and Sarasota's spectacular boating destinations. Whether spending the day fishing, cruising Sarasota Bay, or exploring the Gulf waters, the boating lifestyle is right outside your door. With these substantial waterfront improvements already completed, you can begin enjoying the freedom of waterfront living from day one. Additional highlights include a waterfront community swimming pool, convenient ground-level lanai access, and a pet-friendly community. With a three-month minimum rental period, this residence offers flexibility for year-round living, a seasonal Siesta Key getaway, or potential rental income. Most furnishings are also available separately, offering an opportunity for a convenient transition to island living. Ideally positioned near Turtle Beach, residents can enjoy beautiful Gulf sunsets, beachcombing, and leisurely shoreline strolls, while nearby waterfront restaurants, shopping, and the vibrant attractions of Siesta Key Village complete the coastal experience. Whether you're searching for a Siesta Key waterfront home, a boating retreat, or a seasonal Florida escape, 9203 Midnight Pass Road delivers an exceptional opportunity to enjoy the very best of waterfront living on Siesta Key.

9203 Midnight Pass Road Unit 2, Sarasota
5324 Siesta Court, Sarasota
$1,250,000
4 Beds ⋅ 4 Baths ⋅ Siesta Cove Sub SubDv. ⋅ 34242 Zip Code
Virtually Staged. Set in desirable Siesta Cove, 5324 Siesta Court pairs inviting indoor and outdoor living with the charm of an established neighborhood known for its quiet, tree-lined streets and proximity to Siesta Beach. Step through the front door into a bright foyer that opens to the dining area and vaulted living room, where a fireplace with a white mantel and raised brick hearth creates a welcoming focal point. Large-format tile flows throughout the main living spaces, while an open staircase with wood treads leads to the loft above. The adjoining kitchen features white cabinetry, stainless steel appliances and a generous island with a veined countertop and seating. A sunny breakfast nook overlooks tropical greenery, and a separate wet bar with glass-front cabinetry keeps beverages and serving pieces conveniently close at hand. The first-floor family room provides another comfortable gathering space, with warm-toned flooring and sliding glass doors opening to the screened deck. The 4-bedroom, 4-bathroom split floor plan includes two first-floor primary suites, each with its own renovated ensuite bath and views of tropical greenery. One features a freestanding soaking tub and large, separate glass-enclosed shower, while the other offers a long dual-sink vanity and direct access from the bath to the screened deck. A generously sized 3rd bedroom is complemented by an updated bathroom with glass and tile finishes. Bright and inviting, the fourth bedroom features a private exterior entrance, offering added flexibility for guests. A 4th bathroom features classic beadboard wainscoting. A dedicated laundry area accommodates a full-size washer and dryer and includes a utility sink and open shelving. Upstairs, the large open loft overlooks the living room and offers versatile space for a home office, bonus room or playroom. An exposed wood beam adds warmth and character, while sliding glass doors lead to a private screened balcony with room for loungers and a bistro table. A spiral staircase connects the balcony to the multilevel screened deck below. Outside, expansive new front landscaping frames the paver approach and front entry beneath mature shade trees. An attached two-car garage provides additional storage, while the home's elevated design, brand-new 2026 roof and no history of 2024 storm damage offer added peace of mind. In the backyard, tropical greenery surrounds a shaded lounge area with new white crushed shell and a separate sunlit space for outdoor dining. Multiple sliding glass doors create an easy connection between the interior and screened deck, and the large lot offers room to envision a future pool. Enjoy morning walks and evening strolls through Siesta Cove, with the white quartz sands of Siesta Beach just a short walk away. Take a street-legal golf cart to the shops and restaurants of Siesta Key Village, then return home for dinner on the screened deck. With Siesta Key named the No. 1 Best Beach in the U.S. in U.S. News & World Report's 2026 rankings, this home offers a welcoming setting to enjoy the island lifestyle.

5324 Siesta Court, Sarasota
9000 Blind Pass Road Unit B307, Sarasota
$895,000
2 Beds ⋅ 2 Baths ⋅ Fishermans Cove SubDv. ⋅ 34242 Zip Code
Come and see why Fisherman’s Cove is one of the most highly desirable communities on Siesta Key! This is one of the only complexes in which direct beachfront living also offers the boating lifestyle right out the back door! Discover an exceptional opportunity to own a top-floor 2-bedroom, 2-bath condominium offering 1090 square feet of coastal living, complete with an enclosed lanai showcasing breathtaking direct Gulf views and spectacular sunsets. One of the residence’s stunning features are new impact resistant glass sliders with in the lanai, an upgrade that beautifully captures the panoramic water views while allowing abundant natural light to fill the living space. Inside, the residence features attractive laminate flooring with sound-buffered installation throughout, light and bright colors and a spacious walk-in closet with a washer and dryer- very rare for a condominium. Offered turnkey furnished, this condominium is ready to enjoy as a full-time residence, private beach retreat, or investment property as WEEKLY RENTALS ARE ALLOWED! Newer HVAC and water heater are also a huge bonus. Beyond its incredible beachfront setting, Fisherman’s Cove offers a unique combination of Gulf-front living and boating convenience, featuring direct Gulf frontage and access to the Intracoastal Waterway. Residents enjoy approximately 900 feet of beautiful sandy beach, gated access, a heated community pool, kayak storage and dock, fishing from the community docks, and 40 boat slips available to owners and renters at no additional charge. Additional conveniences include elevator access, assigned parking, ample guest parking, storage, on-site management and rental office, and gas grilling areas along the picturesque lagoon. Experience the best of Siesta Key living with breathtaking Gulf sunsets, private beachfront access, exceptional boating amenities, and a welcoming waterfront community. An outstanding opportunity to own your very own piece of paradise!

9000 Blind Pass Road Unit B307, Sarasota
Start Your Search

How much is your home worth?

Get instant property value now!