Osprey/Nokomis Homes with Bay Front Water Frontage

3 Beds ⋅ 3 Baths ⋅ Matz Sub SubDv. ⋅ 34275 Zip Code

Experience the true Florida waterfront lifestyle on 1.6± acres along beautiful Roberts Bay in Nokomis. Freshly updated and move-in ready, this spacious bayfront home features new interior paint throughout, new carpet, and new flooring in the pool room, bedrooms and master bath. From peaceful mornings overlooking the water to evenings spent relaxing beside the oversized pool and spa, every day here feels like a getaway. Designed for both comfortable living and effortless entertaining, the property offers generous indoor and outdoor spaces framed by breathtaking water views. The oversized pool and spa feature both solar and electric heating, creating the perfect place to relax year round. A newly constructed wood dock with water, electric, and a boat lift puts boating, fishing, and Gulf adventures right outside your door. A pontoon boat currently on the lift may also be negotiated with the sale. The oversized two-car garage includes a built-in workshop with plenty of room for tools, recreational equipment, storage, and hobbies. With no HOA and no deed restrictions, the property offers exceptional flexibility for enjoying the waterfront lifestyle your way. Beyond its appeal as a private coastal retreat, the 1.6± acre property is zoned RMF-3, offering potential for up to 13 units an acre, subject to county approval and buyer verification. This creates a unique opportunity for builders, developers, and investors seeking a premier waterfront location. Conveniently located near Nokomis Beach, shopping, everyday amenities, and popular waterfront restaurants, with additional dining walking distance, this one-of-a-kind property offers privacy, versatility, and direct access to the best of coastal Florida living. Whether enjoyed as a personal waterfront estate or explored for its redevelopment potential, this is a rare opportunity on Roberts Bay.

102 Brenda Lane, Nokomis

$3,700,000

5 Beds ⋅ 5 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Welcome to extraordinary living! This completely private oasis is perfectly positioned along North Creek in The Oaks Bayside, one of the most sought-after communities in South Sarasota. Situated on a lot and a half, the view is peppered with lush foliage, creating total seclusion and the feel of a luxury retreat. One of the most desirable floor plans in the community, with open flow and complete separation from the master suite and guest accommodations, creates a comfortable and highly functional living space. The casita provides the perfect separate space for an office, a studio or long-term guest accommodations, with stunning views from the second floor. Fine finishes and quality craftsmanship are showcased throughout this home, custom built by renowned contractor Baron Construction. Features include French oak flooring, quartz countertops, premium appliances, and numerous custom details. The combined living and dining area provides an ideal setting for entertaining, opening directly to the outdoor pool and spa. For more casual gatherings, the spacious kitchen and breakfast nook flow seamlessly into the family room and out to the covered outdoor living space. This screened area is beautifully designed with a pool and spa, and grill. The covered areas and ceiling fans provide comfort for al fresco dining. The lots’ site is spectacular, with great water views, and areas to launch your kayak or paddleboard. Add in the practical features like a newer roof, oversized three car garage and huge pantry and you have found a home of distinction with no peer. The Oaks Bayside is a gated bayfront community within The Oaks. The distinguished private club offers 2 championship golf courses, pickleball and tennis courts, a state-of-the-art WellFit Center, exquisite dining options and a celebrated social calendar. The location provides convenient access to downtown Sarasota, dining, nightlife, and the cultural amenities of the Gulf Coast. Club membership is required with home ownership. There is currently no waiting list for either Golf or Sports/Social membership.

324 Osprey Point Drive, Osprey

$3,695,000

3 Beds ⋅ 2 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

Gulf-to-bay on Casey Key. Wake up to golden sunrises over Blackburn Bay, spend your afternoons on your own private sandy beach and end the day surrounded by breathtaking views stretching from the Intracoastal Waterway to the turquoise waters on the Gulf. This exceptional Gulf-to-bay property offers a rare opportunity to experience the very best of waterfront living on Casey Key’s pristine eight-mile barrier island. Impeccably maintained, the charming vintage cottage is move-in ready and filled with coastal character. The inviting floor plan features a spacious living room, two bedrooms, an office that presently serves as a third bedroom and a dining area framed by beautiful bay views. Go outside and embrace the waterfront lifestyle with a peaceful deck, private dock, pool and a 10,000-pound boat lift installed in 2022. The property offers some of the deepest boating water in the area, making it ideal for boating, fishing, paddleboarding, kayaking and endless days on the water. Recent improvements include a new roof in 2023 and interior and exterior paint, allowing you to settle in and enjoy this special setting. For those dreaming of creating a new coastal residence, the property also presents an exceptional opportunity to build in the future while providing immediate use and enjoyment. Beyond the property, Casey Key offers an unparalleled sense of privacy and natural beauty while remaining conveniently close to everything you need. Private air travel is available at Venice Airport (within 15 minutes) and Sarasota-Bradenton International Airport (within 40 minutes). Shopping, dining, golf and other amenities are all within easy reach. Whether you envision preserving the charm of this beloved beach cottage or creating a spectacular new waterfront retreat, this extraordinary Gulf-to-bay property is a rare slice of paradise and an opportunity to call Casey Key home.

1604 Casey Key Road, Nokomis

$525,000

Bay Point SubDv. ⋅ 34275 Zip Code

Newly available 0.27-acre waterfront lot directly on Dona Bay, offering a rare opportunity to build your own custom home in beautiful Nokomis. Enjoy the best of Florida coastal living with convenient access to Nokomis Beach, Casey Key, and the Gulf of Mexico, along with waterfront dining, local restaurants, marinas, and outdoor recreation nearby. Ideally positioned between Venice and Sarasota, this property offers a peaceful waterfront setting while keeping shopping, dining, entertainment, and cultural attractions within easy reach. Build your dream home and enjoy breathtaking bayfront surroundings, coastal breezes, and the relaxed lifestyle that makes Nokomis such a sought-after destination.

114 Magnolia Avenue, Nokomis

$4,795,000

Casey Key SubDv. ⋅ 34275 Zip Code

A rare Gulf-to-Bay opportunity on Casey Key, where nearly an acre of land stretches from the turquoise waters of the Gulf of Mexico to the protected waters of the bay. With just over 100 feet of water frontage on both the Gulf and bay sides (and more than 400-feet of depth), this exceptional property presents an opportunity to create a custom waterfront retreat tailored entirely to your vision. Set along one of Sarasota’s most coveted barrier islands, the expansive homesite offers the extraordinary combination of a private Gulf beach, spectacular sunset views and direct boating access—all from one property. On the beach side, step directly onto your own stretch of walkable sandy shoreline and enjoy unobstructed views across the Gulf of Mexico. Approximately 104 feet of Gulf frontage and a newer seawall, completed in 2004, establish an impressive setting for a future coastal residence designed around the water, sunsets and relaxed Casey Key lifestyle. Mature tropical landscaping and the parcel’s generous proportions create a wonderful sense of privacy rarely found along the coast. Across the property, approximately 104 feet of bay frontage opens another dimension of waterfront living. The dock and boat lift, both added in 2022, provide convenient access to the Intracoastal Waterway and the exceptional boating, fishing and cruising opportunities of Southwest Florida. Spend the morning on the boat, return home by water and finish the day watching the sun disappear into the Gulf from your own backyard. The nearly one-acre parcel provides remarkable flexibility for designing a custom residence that takes full advantage of its Gulf-to-Bay orientation, with the potential to capture water views in both directions. Imagine expansive indoor-outdoor living spaces, elevated terraces, a resort-style pool environment and private gathering areas framed by tropical landscaping—all designed specifically around this extraordinary coastal setting. Casey Key remains one of the Gulf Coast’s most distinctive residential enclaves, prized for its natural beauty, privacy and laid-back character. Yet this secluded island setting is remarkably convenient to the restaurants, boutiques and waterfront charm of Nokomis and Venice, as well as nearby Nokomis Beach, the North Jetty, Venice Island and the Legacy Trail. Downtown Sarasota’s cultural attractions, dining and shopping are also within comfortable reach, while the Intracoastal and Gulf of Mexico are quite literally at your doorstep. 2417 Casey Key Road is more than a waterfront homesite—it is an opportunity to create a legacy property on one of Southwest Florida’s most treasured barrier islands, with the Gulf at one door and the bay at the other.

2417 Casey Key Road, Nokomis

$4,795,000

2 Beds ⋅ 2 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

A rare Gulf-to-Bay opportunity on Casey Key, where nearly an acre of land stretches from the turquoise waters of the Gulf of Mexico to the protected waters of the bay. With just over 100 feet of water frontage on both the Gulf and bay sides (and more than 400-feet of depth), this exceptional property presents an opportunity to create a custom waterfront retreat tailored entirely to your vision. Set along one of Sarasota’s most coveted barrier islands, the expansive homesite offers the extraordinary combination of a private Gulf beach, spectacular sunset views and direct boating access—all from one property. On the beach side, step directly onto your own stretch of walkable sandy shoreline and enjoy unobstructed views across the Gulf of Mexico. Approximately 104 feet of Gulf frontage and a newer seawall, completed in 2004, establish an impressive setting for a future coastal residence designed around the water, sunsets and relaxed Casey Key lifestyle. Mature tropical landscaping and the parcel’s generous proportions create a wonderful sense of privacy rarely found along the coast. Across the property, approximately 104 feet of bay frontage opens another dimension of waterfront living. The dock and boat lift, both added in 2022, provide convenient access to the Intracoastal Waterway and the exceptional boating, fishing and cruising opportunities of Southwest Florida. Spend the morning on the boat, return home by water and finish the day watching the sun disappear into the Gulf from your own backyard. The nearly one-acre parcel provides remarkable flexibility for designing a custom residence that takes full advantage of its Gulf-to-Bay orientation, with the potential to capture water views in both directions. Imagine expansive indoor-outdoor living spaces, elevated terraces, a resort-style pool environment and private gathering areas framed by tropical landscaping—all designed specifically around this extraordinary coastal setting. Casey Key remains one of the Gulf Coast’s most distinctive residential enclaves, prized for its natural beauty, privacy and laid-back character. Yet this secluded island setting is remarkably convenient to the restaurants, boutiques and waterfront charm of Nokomis and Venice, as well as nearby Nokomis Beach, the North Jetty, Venice Island and the Legacy Trail. Downtown Sarasota’s cultural attractions, dining and shopping are also within comfortable reach, while the Intracoastal and Gulf of Mexico are quite literally at your doorstep. 2417 Casey Key Road is more than a waterfront homesite—it is an opportunity to create a legacy property on one of Southwest Florida’s most treasured barrier islands, with the Gulf at one door and the bay at the other.

2417 Casey Key Road, Nokomis

$9,750,000

5 Beds ⋅ 8 Baths ⋅ Casey Key SubDv. ⋅ 34229 Zip Code

At the northernmost point of Casey Key, where the Gulf meets the tranquil waters of Little Sarasota and Blackburn Bay, an extraordinary private estate unfolds between two worlds of water. Beyond a secluded entrance lies a residence of remarkable distinction, an Italianate architectural masterpiece spanning more than 8,000 square feet, with a private sandy beach on the Gulf and a rare, grandfathered covered boat lift on the bay. Designed by renowned architect Clifford A. Scholz and masterfully built by Delta Southern Construction, the estate was envisioned not simply as a home but as a setting for an exceptional life. Here, timeless architecture, impeccable craftsmanship and modern coastal luxury converge in a residence designed to bring family and guests together while preserving moments of treasured privacy. From the moment of arrival, the architecture reveals a quiet sense of grandeur. Cypress-beamed ceilings, graceful arches, French doors, handcrafted millwork, and luminous water views create a sequence of spaces that feel both magnificent and deeply welcoming. The living room commands a captivating panorama across the Bay, while walls of glass and elegantly framed openings blend the boundary between interior and landscape. The culinary spaces are equally impressive. A sophisticated kitchen is complemented by a dedicated wine cellar, butler’s pantry, and wet bar—an entertainer’s dream conceived for intimate dinners and spectacular gatherings alike. Beyond, a grand media room provides an elegant retreat for cinematic evenings, music, and cultural pursuits. The primary suite is a private sanctuary unto itself. A serene sitting room, sumptuous bath, dual closets, breakfast nook, and expansive water views create an atmosphere of effortless indulgence. Three additional bedroom suites offer luxurious accommodations for family and guests, while a fifth suite transforms into a private wellness retreat with a home gym, steam room, and sauna. A magnificent marble staircase leads to an office and library distinguished by leaded-glass doors, handcrafted built-in shelving, a coffered ceiling, and mesmerizing Gulf views. Throughout the residence, additional spaces for recreation, relaxation, and quiet spaces have been thoughtfully integrated, ensuring that every corner serves the extraordinary rhythm of life on the water. Outside, stone terraces cascade toward a shimmering infinity pool, where the architecture gives way to sky and water. Days unfold between the pool and the Gulf, afternoons drift toward the bay, and evenings become unforgettable beneath the coastal sky. For the boating enthusiast, the deep-water dock offers quick access with no bridges to the Gulf through Midnight Pass and features one of the area’s rare grandfathered covered boat lifts. For those drawn to the Gulf, a private sandy beach provides a front-row seat to spectacular sunsets and the timeless beauty of the sea. Yet perhaps the estate’s greatest luxury is its sense of place. North Casey Key remains one of Sarasota County’s most coveted enclaves—a sanctuary of quiet privacy and natural beauty, remarkably close to world-class golf, tennis, dining, shopping, and the cultural attractions of Sarasota. This is more than an exceptional residence. It is a private coastal world—an irreplaceable estate where architecture, water, nature, and the art of gracious living come together in extraordinary harmony.

1216 N Casey Key Road, Osprey

$599,000

2 Beds ⋅ 2 Baths ⋅ Blackburn Harbor SubDv. ⋅ 34229 Zip Code

Sweeping water views, beautiful updates and an enviable waterfront lifestyle come together in this exceptional fourth-floor residence at Blackburn Harbor. Docking available on the premises for a very reasonable quarterly fee. Set along South Creek with direct access via canal to the Intracoastal Waterway and the Gulf, this spacious 2-bedroom, 2-bath home with a versatile den captures the essence of coastal Florida living, from spectacular sunsets and gentle sea breezes to easy access for kayaking and boating. Thoughtfully renovated, the residence offers a fresh, modern feel with laminate wood flooring throughout, plantation-style window shutters, updated lighting and new vertical drapery on the sliding doors. The open living and dining areas flow seamlessly to the spacious screened lanai, where expansive water views create a beautiful setting for morning coffee, afternoon relaxation or sunset entertaining. The updated kitchen features quartz countertops and backsplash, stainless-steel appliances replaced in 2022, a new faucet and disposal, and thoughtfully added cabinet drawers for enhanced storage and functionality. Both bathrooms were beautifully updated in 2022 with new cabinetry, sinks, granite countertops, backsplashes, faucets, mirrors and fresh paint. The spacious primary suite enjoys tranquil water views, three closets—including two walk-ins—and a generous ensuite bath. The guest bedroom features a walk-in closet and convenient access to the second bath, creating a comfortable private suite for guests. The den adds valuable flexibility as a home office, reading room or occasional third bedroom. Additional improvements include a new HVAC system in 2023, water heater, washer and dryer in 2022, and a new metal community roof installed in 2025. HOA fees include water, sewer, cable and Wi-Fi, leaving electric as the primary utility expense. Blackburn Harbor is an inviting gated waterfront community surrounded by lush tropical grounds and an active social atmosphere. Residents enjoy a heated pool, fitness center, tennis, pickleball, shuffleboard, clubhouse, walking paths, waterside gathering areas, grills and a kayak launch. Boat dockage is available for approximately $252 per month, offering the rare opportunity to keep your boat close to home and enjoy the waterways at your leisure. Located minutes from Nokomis Beach, the Legacy Trail, Oscar Scherer State Park, shopping and dining, this is a wonderful opportunity to enjoy the best of the Sarasota-area waterfront lifestyle—with the updates already done and nothing left to do but settle in and enjoy.

5100 Jessie Harbor Drive Unit 404, Osprey

$985,000

3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code

ENJOY BREATHTAKING SUNSET VIEWS ACROSS LITTLE SARASOTA BAY AND THE GULF FROM THIS STUNNING 8TH-FLOOR PENTHOUSE! This exceptional 2,203SF Condominium offers 3 Bedrooms, 3 Full Baths, a coveted Private 2-Car Garage, and the privacy of the highly sought-after, gated Oaks Preserve neighborhood. Arrive through your private elevator foyer and step into a home where panoramic, unobstructed views of Little Sarasota Bay and the Gulf immediately take center stage. Thoughtfully designed with an impressive array of upgrades, the residence features high ceilings, crown molding, hardwood and tile flooring, and a beautifully appointed kitchen with a large island and seating area, granite countertops, stainless steel appliances, solid-wood cabinetry, and ample storage. The spacious Owner’s Suite is a peaceful retreat, complete with a generous walk-in closet, custom-tiled shower, relaxing soaking tub, and dual vanities. Step outside onto the expansive balcony and enjoy a serene setting surrounded by spectacular water views, abundant wildlife, and unforgettable Gulf sunsets. Hurricane-impact windows and sliding doors provide added peace of mind. Climate-controlled storage is conveniently located on the second floor. Residents of Meridian enjoy an array of private amenities, including a heated pool and spa, fitness center, and outdoor grilling area, along with access to the exceptional amenities of The Oaks Club’s main campus. Experience elevated coastal living, spectacular views, privacy, and resort-style amenities—all from this remarkable penthouse at The Oaks. The Oaks Club is a member-owned private golf community with more than 40 years of excellence and is the only private residential golf club in the Sarasota, Bradenton, and Fort Myers region recognized by both Platinum Clubs of America and Distinguished Emerald Clubs of the World. Residents enjoy a magnificent 30,000-square-foot clubhouse, three exceptional dining venues, two championship 18-hole golf courses, outstanding golf instruction, a premier racquet program with 12 Har-Tru HydroGrid tennis courts and pickleball courts, croquet, bocce, basketball, a Junior Olympic swimming pool, and a newly expanded state-of-the-art wellness, fitness, and spa facility. Recognized as "The Healthiest Club" and an Audubon Society-certified community, The Oaks offers an unmatched lifestyle. Ideally located in one of Sarasota County's most sought-after communities, this exceptional residence is just minutes from world-renowned beaches, top-rated schools, fine dining, shopping, and Sarasota's vibrant arts and cultural attractions, making it a rare opportunity to enjoy luxury living in a truly prime location.

409 N Point Road Unit 803, Osprey

$28,900

Gulf Harbor Marina SubDv. ⋅ 34275 Zip Code

The industrious Gulf Harbor Marina is a very ideal spot to keep your best vessel high and dry until you are ready to splash in and go! N-60 is 9.8W X 25L X 8H, and can hold a vessel that is 8.8W, 24L and 7H, it is on the bottom rack and is easy for an owner to access their boat for quick maintenance needs and an even quicker drop in to your next water adventure. Gulf Harbor Marina is a perfect spot to keep your vessel in between uses that is next to fabulous water front restaurants, it has beautiful updated facilities, a bait shop with frozen or live bait (squid, shrimp, sardines and chum), fish cleaning tables with connected water, and a shaded gazebo for those to wait for their vessel in the shade. The marina also has a service center with lots of parts, they can order anything you need for your boat and even do repairs and installs, but if you are a do it yourself person, there are work racks where you can work on your own with day time use of electrical hook up. There is an easy phone app called speedy dock where you can schedule your splash times in advance 8:15AM-4pm, and you can have as many drop ins at no charge, just need to request it in the app. On site they carry diesel and Rec 90 fuels. There are multiple 30,000lb lifts to get boats in and out safely and quickly. There are 24/7, 365 security cameras. You will need to have 300k in liability insurance for your vessel with Gulf Harbor Marina as an intercept party. the rooftop of the storage building is open for great air flow. Plenty of parking on site for easy loading and unloading. The marina staff are extremely friendly and eager to help and provide excellent customer service.

100 Circuit Road Unit N60, Nokomis

$575,000

2 Beds ⋅ 3 Baths ⋅ The Harbor Villas At Dona Bay SubDv. ⋅ 34275 Zip Code

Live the SALT LIFE! This unit is a BOATER'S DREAM! Enjoy breathtaking waterfront living in this beautifully updated 2-bedroom, 2.5-bath condo overlooking Dona Bay with direct access to the Intracoastal Waterway and Gulf of Mexico. This spacious 1,642 sq. ft. residence is sunny and bright, features an open floor plan with high ceilings, solid wood cabinetry, solid-surface countertops, and beautiful water views from the kitchen, living, dining areas, and expansive covered front porch. Step outside and enjoy your private waterfront lifestyle with a deeded dock and recently installed 10,000-lb. boat lift, providing convenient access to the Gulf with no bridges and approximately 5 minutes by boat to Venice Inlet. The unit also includes two deeded parking spaces in the enclosed first-floor garage, with private elevator access directly to the residence. Located in The Harbor Villas at Dona Bay, residents enjoy a waterfront community with a pool, fitness center, sidewalks, and water access. Conveniently located along Tamiami Trail in Nokomis, close to Venice, beaches, dining, shopping, and outdoor recreation. A rare opportunity to own a waterfront retreat designed for enjoying the Florida boating lifestyle!

516 Tamiami Trail S Unit 306, Nokomis

$550,000

3 Beds ⋅ 2 Baths ⋅ Venice By Way SubDv. ⋅ 34275 Zip Code

Virtually Staged. Discover the charm of Old Florida living with this unique Nokomis property, ideally situated on an oversized 12,000-square-foot homesite surrounded by mature tropical landscaping with beautiful views of Shakett Creek and Dona Bay. Several important improvements have already been completed, including a newer roof, septic system, and electrical panel, all updated in 2018. The HVAC system has been elevated, and the property is equipped with a generator hookup for added convenience. With no HOA or CDD, the property offers exceptional flexibility and a generous yard with plenty of room for your boat, RV, recreational toys, gardening, outdoor activities, or creating your own private backyard oasis. The west-facing setting provides the perfect backdrop for enjoying spectacular Florida sunsets, while nearby Loreto Court County Bay Access offers convenient water access for kayaking and other outdoor adventures. A County-maintained boat ramp and seawall are also just steps away, making this an appealing location for boating and waterfront enthusiasts. The main residence features 3 bedrooms and 2 bathrooms with distinctive Old Florida character and a comfortable, connected layout. The living room, dining area, and family room flow together to create an inviting space for everyday living and entertaining, with the centrally located cottage-style kitchen serving as the heart of the home and providing easy access to each gathering area. Tile flooring adds to the home's casual Florida feel, while a spacious screened lanai extends the living space outdoors, offering a comfortable place to relax, entertain, and enjoy the surrounding tropical setting. Adding to the property's unique appeal is a detached enclosed gazebo with an attached full bathroom, creating versatile bonus space ideal for a private guest retreat, lounge, home office, studio, hobby room, or entertaining area. A separate storage shed provides additional space for lawn equipment, tools, and outdoor essentials. Whether you choose to embrace the home's vintage coastal character, renovate and make it your own, or explore the possibilities for a future elevated residence designed to take greater advantage of the surrounding water views, this property offers exciting potential in a desirable Nokomis location. Enjoy easy access to the Legacy Trail, Nokomis Beach, boating, kayaking, dining, shopping, and everything that makes Florida's Gulf Coast lifestyle so appealing. With its generous homesite, water views, nearby bay access, mature tropical setting, and freedom from HOA and CDD restrictions, this distinctive property presents a wonderful opportunity to create your own piece of paradise in Nokomis. **PLEASE ENJOY THE 3D INTERACTIVE VIRTUAL TOUR ASSOCIATED WITH THIS LISTING**

807 Lucille Avenue, Nokomis

Osprey/Nokomis Homes with Bay Front Water Frontage

Newest Osprey/Nokomis Homes with Bay Front Water Frontage