Osprey/Nokomis Homes with Boatable Water Water Frontage

Osprey/Nokomis Homes with Boatable Water Water Frontage

Welcome to the enchanting communities of Osprey and Nokomis, nestled in the heart of Sarasota County, Florida. These picturesque towns, situated along the stunning Gulf Coast, offer a perfect blend of tranquility and vibrant coastal living. Known for their lush landscapes and warm, inviting atmosphere, Osprey and Nokomis are ideal for those seeking a peaceful retreat while still enjoying the conveniences of modern life.

One of the most alluring features of this region is its access to boatable waterfront properties. Imagine waking up to the gentle sounds of the water lapping against your dock, with the sun rising over the horizon, casting a golden glow across the tranquil waters. Homes with boatable water frontage in Osprey and Nokomis are not just residences; they are gateways to a lifestyle filled with adventure. From fishing and kayaking to leisurely boat rides along the Intracoastal Waterway, your days can be filled with sun-soaked exploration.

Osprey boasts rich history and culture, with attractions like the historic Spanish Point and the serene Legacy Trail. Meanwhile, Nokomis is known for its beautiful beaches and community spirit, making it a perfect spot for families and retirees alike. With a variety of dining options, boutique shops, and recreational parks, there’s always something to do.

Whether you're looking for a charming waterfront cottage or a luxurious estate, Osprey and Nokomis offer a diverse range of homes that cater to every lifestyle. Embrace the coastal charm and vibrant community spirit in these wonderful Florida towns, where your dream home awaits on the water's edge.

Newest Osprey/Nokomis Homes with Boatable Water Water Frontage

3718 Sandspur Lane, Nokomis
$5,750,000
4 Beds ⋅ 8 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code
At the water’s edge of Sandspur Lane sits one of Casey Key’s best-kept secrets: a stunning estate offering unmatched privacy, tranquility, protected waterfront, and bespoke contemporary coastal architecture. A multi-year renovation completed in 2024 reimagined the property, adding more than 2,000 square feet of interior and exterior living space and transforming an already exceptional waterfront home into a truly distinctive residence. Tucked at the end of this quiet, private lane, the home’s structural features and sheltered location provide proven storm-resilient advantages. Ownership of both sides of the canal protects the mature trees and vegetation along the opposite shoreline, preserving natural privacy. The main level features vaulted ceilings and an open floor plan connecting the modern kitchen with dining, living, and family rooms, while wraparound aquarium glass windows and sliding glass doors flood the space with natural light and offer views of the water and the parcel’s expansive waterfront setting. A floating staircase rises through a circular glass stair tower to the primary suite, featuring a spacious bath, sitting room, and a private balcony with long water views. An adjoining casita with its own private entrance and water views provides luxurious accommodations for family, guests, or in-home staff. Two dedicated offices with built-in cabinetry and granite desks offer long ICW views, creating an inspiring setting for work or personal pursuits. A new elevator connects every level, from the garage to the rooftop deck. Designed for recreation and entertaining, the property features a cabana with bar and outdoor kitchen, a new waterfall spa and remodeled pool with water features, a home gym, firepit, indoor-outdoor Sonos sound system, and multiple balconies, terraces, and decks. After sunset the extensive outdoor lighting, including dock and underwater fish lights, transforms the property. The long driveway and motor court accommodate parking for 12–15 vehicles— a rarity on Casey Key. The 200 feet of protected waterfront includes a newly added 45-foot dock, 20,000-lb. boat lift, and two PWC lifts. And when the Gulf beckons, deeded beach access leads to its warm waters and shoreline. From sunrises over the ICW to Gulf sunsets from the rooftop deck and illuminated evenings poolside, the home embraces its waterfront setting from virtually every angle. This residence offers a package increasingly hard to find: extraordinary privacy, tranquility, and protected waterfront living—all wrapped in a beautifully reimagined contemporary coastal estate on one of Florida’s most exclusive islands.

3718 Sandspur Lane, Nokomis
250 Hidden Bay Drive Unit 302, Osprey
$625,000
3 Beds ⋅ 2 Baths ⋅ Edgewater/Hidden Bay Ph 1 Bldg SubDv. ⋅ 34229 Zip Code
LOCATION, LOCATION, LOCATION! Experience waterfront living in this beautifully upgraded luxury condominium, ideally located in a gated, resort-style community nestled between US 41 and Little Sarasota Bay. The residence features 3 bedrooms, a den, and 2 full bathrooms. With no building or walkway directly behind the unit, the property also offers a peaceful sense of privacy. Step inside to an open-concept layout where the kitchen, dining, and living areas flow seamlessly together. High ceilings, elegant tray ceilings with crown molding, and hurricane-impact windows and sliding glass doors fill the home with natural light while creating a beautiful connection to the outdoors. Both the living area and primary suite open to an oversized screened balcony—an exceptional outdoor living space offering panoramic views of the bay, Casey Key, the Gulf, and surrounding preserves. Enjoy watching boats and wildlife while taking in spectacular sunsets from your own private outdoor retreat. The well-appointed kitchen features an expansive area of granite countertops, stainless steel appliances, and ample cabinetry. The spacious primary suite offers two walk-in closets and a large en-suite bathroom with dual split vanities. The second en-suite bedroom features a generous walk-in closet and a convenient pocket door providing access to the second bathroom. A full-size laundry room located inside the unit adds everyday convenience. Designed for easy living, the residence offers elevator access, two parking spaces including one assigned space, and a private storage room beneath the building. The condominium fee includes building and flood insurance, reserves, internet, cable TV, exterior maintenance, pest control, and water, providing convenient, low-maintenance ownership. The gated community offers a resort-style setting with a heated pool and spa, expansive sundeck, grilling area, pickleball and tennis courts, kayak storage and launch, and a scenic boardwalk through the mangroves leading to a fishing pier. The clubhouse features a catering kitchen, library, fitness room, and additional gathering spaces. The location is hard to beat, conveniently positioned between Sarasota and Venice, with approximately 6.5 miles to Siesta Key and Nokomis Beach, less than one mile to Bay Street Park and Osprey Dog Park, approximately 2 miles to the Legacy Trail Osprey Junction and Casey Key, and approximately 3 miles to Oscar Scherer State Park. An array of restaurants, shopping, marinas, golf, and medical services are also conveniently nearby. Whether you're looking for a full-time residence, vacation home, investment property, or a convenient lock-and-leave lifestyle, this waterfront condominium brings together privacy, exceptional water views, extensive upgrades, resort-style amenities, and a highly desirable location. Come experience the views and discover the possibilities this property offers.

250 Hidden Bay Drive Unit 302, Osprey
275 Lookout Point Drive, Osprey
$4,590,000
5 Beds ⋅ 5 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Experience exceptional waterfront living in Southbay Yacht & Racquet Club at this expansive custom John Cannon residence offering more than 5,200 square feet, 5 bedrooms, 5 baths and sweeping panoramic water views from both levels. Set along more than 135 feet of waterfront, the home was thoughtfully designed to embrace its remarkable setting, with soaring ceilings, generous expanses of glass and beautifully proportioned indoor and outdoor living spaces overlooking the bay and Intracoastal Waterway. A completely reimagined front drive and all-new landscaping create a striking first impression and a fresh, refined coastal presence. Beyond the grand double-door entry, the home immediately opens to dramatic water views, drawing the eye through the interior and out toward the horizon. Ceilings rising to approximately 21 feet enhance the sense of scale, while a series of inviting living and entertaining spaces allow the home to feel equally suited for intimate evenings or larger gatherings. The kitchen serves as the heart of the residence, anchored by a substantial granite island and complemented by a gas cooktop with pot filler, while views stretch beyond the pool to the water. A full bar and dedicated wine room enhance the main level, with an additional wet bar upstairs for effortless entertaining throughout the home. Privately positioned on the main level, the primary suite is a serene waterfront retreat with a sitting area, two generous closets and an expansive bath. Additional downstairs bedrooms are thoughtfully located on the opposite side of the residence, creating privacy and separation for family and guests. Upstairs, either an office or a fifth bedroom offers an elevated and inspiring setting for work or quiet retreat, with access to the upper terrace and its sweeping water views. From both floors, the landscape of water and sky becomes part of the experience of the home. Outdoor living is equally memorable. A heated pool and spa, covered and screened entertaining areas, outdoor kitchen, fireplace, expansive terraces and private dock create a seamless connection between the residence and the waterfront. Mornings begin with peaceful views across the water, afternoons unfold poolside, and evenings are defined by the colors of sunset. Southbay Yacht & Racquet Club offers one of the area's most distinctive boating lifestyles. Its community-owned deep-water marina accommodates vessels up to 55 feet, allowing residents to walk or take a golf cart from home to their boat. Community amenities include a renovated clubhouse, geothermal pool, fitness center overlooking the marina, tennis and pickleball courts, bocce, shuffleboard, basketball, kayak storage, a waterfront park, approximately 20 acres of common grounds and miles of walking trails. Perfectly positioned between Sarasota and Venice and convenient to Siesta Key, Nokomis Beach, the Legacy Trail, Pine View School, waterfront dining, shopping and Oscar Scherer State Park, 275 Lookout Point is a compelling blend of scale, setting and lifestyle—a substantial waterfront residence with panoramic views, private outdoor living and direct access to the heart of Southbay’s boating community.

275 Lookout Point Drive, Osprey
1101 Kings Way Drive, Nokomis
$925,000
4 Beds ⋅ 4 Baths ⋅ Laurel Landings Estates SubDv. ⋅ 34275 Zip Code
Welcome to your ultimate Florida oasis with access to the Intracoastal Waterway! This exquisite 4-bedroom, 3.5-bath home was thoughtfully renovated in 2022 with a focus on comfort, style, and modern living. A metal roof installed in 2024 provides added peace of mind. Inside, enjoy the contemporary elegance of luxury vinyl flooring, modern tile accents, and high-end ceiling fans throughout. The beautifully appointed kitchen features soft-close cabinetry, a custom quartzite countertop and island, and a custom walk-in pantry, creating a stylish and functional space for everyday living and entertaining. The kitchen also features quality appliances, including a washer and dryer, while two water heaters and two AC units provide year-round comfort. The spacious primary suite offers a private retreat with an ensuite bathroom featuring dual vanities, a walk-in shower, and an oversized soaking tub. The home's exceptional indoor-outdoor design makes Florida living effortless, with sliding glass doors from the living room, kitchen, family room, primary bedroom, and fourth bedroom opening directly to the screened pool area. Pool equipment was upgraded in 2024, screened lanai repainted in 2025, with screws replaced and upgraded to specialty fine-mesh screening designed to keep out even tiny insects, while lush landscaping and a custom fire pit create the perfect setting for relaxing evenings overlooking the water. The three-car garage offers epoxy flooring and custom storage solutions, along with a refrigerator and standalone freezer, included in the sale as-is. Ideally located near schools, shopping, Sarasota Memorial Hospital, and just 3.3 miles from Nokomis Beach, this home offers the perfect blend of convenience and coastal living. Residents also enjoy gated private community boat storage and dock access to the Intracoastal Waterway, along with a gated community RV and boat storage lot for vacation and work vehicles. Beautifully renovated, thoughtfully designed, and ideally situated to enjoy everything the Florida lifestyle has to offer, this exceptional Nokomis home is ready to welcome its next owner.

1101 Kings Way Drive, Nokomis
107 Sunset Drive, Nokomis
$3,875,000
3 Beds ⋅ 5 Baths ⋅ Nokomis SubDv. ⋅ 34275 Zip Code
"Selling Sunset Dr” FURNISHED AND TURNKEY. Positioned 15 feet above sea level and built to 2019 hurricane standards with solid block construction and a clay tile roof, this coastal Mediterranean estate on Dona Bay offers a rare combination of newer construction, direct no-fixed-bridge access to the Gulf via Venice Jetty (5 minutes to the jetty), and a garage built for serious car collectors and RV enthusiasts. The 6-car garage with 50-amp RV hookup and parking for 10 vehicles, make this home one of the few on the market at this scale. Inside, three ensuite bedrooms and a private office are finished with solid custom cabinetry with granite and Cambria quartz counters, and engineered hardwood floors. You will appreciate the newly remodeled culinarian inspired kitchen with upmarket appliances, central vac, and whole-house sound system. A Generac 22kW generator and an elevator shaft prepped for future installation add further peace of mind and flexibility. Step outside to a raised infinity-edge pool and spa, two outdoor kitchens, three fire pits, a golf putting green, a tool shed and an extended entertainment lanai with an upper sun deck, frame exquisite water views. A private 100-ft dock with a 16,000 lb lift that includes approval for a second lift.

107 Sunset Drive, Nokomis
7303 Jessie Harbor Drive Unit 7303, Osprey
$449,000
3 Beds ⋅ 2 Baths ⋅ Heron House SubDv. ⋅ 34229 Zip Code
Welcome to luxury coastal living in this exceptional 3rd-floor penthouse condo nestled in the secluded, resort-style waterfront community of Heron House in Osprey. Offering 1,883 sq. ft. of beautifully light-filled, fully furnished living space, this impressive 3-bedroom, 2-bathroom residence features high-end finishes, warm hardwood floors, plantation shutters, a decorative wood-burning fireplace, and a built-in wet bar perfect for entertaining. The gourmet kitchen is equipped with rich wood cabinetry, granite countertops, stainless steel appliances, and a cozy eat-in breakfast area. Unwind in the expansive primary suite boasting two walk-in closets, a spa-like bath with double vanities, a deep soaking tub, and a separate shower. Step outside onto multiple private balconies to take in tranquil views of lush tropical greenery and calm canal waters—an idyllic setting for outdoor dining or evening cocktails. Located directly on Jessie Harbor with bridge-free, direct access to the Intracoastal Waterway and the Gulf, this gated community offers extraordinary waterfront amenities, including a kayak launch, boat slips (available on a first-come, first-served basis), and frequent visits from local wildlife like otters and dolphins. Residents enjoy a highly active, beautifully maintained HOA complete with a newly installed entrance security gate, heated pool, water aerobics, tennis and pickleball courts, shuffleboard, clubhouse, fitness center, walking trails, locked storage, bike storage, and two assigned covered parking spaces under the building with elevator access. Situated just 10 minutes from Venice Beach, Nokomis Beach, and Casey Key, 20 minutes from world-famous Siesta Key, and minutes from I-75, Oscar Scherer State Park, the Legacy Trail, and Sarasota’s vibrant cultural hub, this hidden gem combines peaceful privacy with unbeatable access to Florida’s finest coastal living.

7303 Jessie Harbor Drive Unit 7303, Osprey
100 Circuit Road Unit S-7, Nokomis
$37,000
Gulf Harbor Marina SubDv. ⋅ 34275 Zip Code
This premium marina dock slip offers the ultimate combination of convenience, top-tier service, and immediate deep-water access. Slip S-7 is 40L x 10W X 8.5H, and can suit a vessel that is 39L X 9W X 7.5H and is located on the top middle rack in the South building. Gulf Harbor Marina is situated in a prime location just 10 minutes from the Venice Jetty and the I-75 corridor, this full-service marina boasts No Fixed Bridges to the Gulf pathway, making it a boater's dream. Environmental excellence and peace of mind come standard, as the facility proudly holds both Clean Marina and Clean Boatyard Designations. Property management is highly cost-effective with low monthly administrative charges, while the facility stays open 7 days a week to serve you. Your boating lifestyle is fully supported by an impressive suite of on-site amenities and professional care. Unmatched Convenience: Enjoy unlimited splashes a month powered by large capacity fork trucks, alongside dedicated boat wash racks, a fish station, and a flush service. Fuel & Supplies: Access discounted fuel sales for owners and tenants, with ice, live shrimp, and frozen bait available right at the fuel dock. There are several covered self service bays to work on your vessel with water and electric provided. Attached to the marina is a service shop if you choose to hire a technician to work on your boat as well as a parts supply shop to prick up any boat or motor parts you might need. Gulf Harbor Marina is located adjacent to two waterfront restaurants and just moments from a county park, public beach, and a public boat ramp. Experience stress-free boating backed by award-winning service in a location that puts the open ocean minutes from your slip.

100 Circuit Road Unit S-7, Nokomis
102 Brenda Lane, Nokomis
$1,890,145
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. A new survey confirms the property is 1.6 acres. The acreage currently shown by the Sarasota County Property Appraiser is incorrect. Survey available upon request.

102 Brenda Lane, Nokomis
324 Osprey Point Drive, Osprey
$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
1604 Casey Key Road, Nokomis
$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
100 Circuit Road Unit N116, Nokomis
$68,500
Gulf Harbor Marina SubDv. ⋅ 34275 Zip Code
Rarely available oversized indoor, 1st level hurricane-protected boat slip at Gulf Harbor Marina in Venice! Measuring an impressive 32Lx9.5Wx11H, this slip accommodates vessels up to 31x8.5x10 offering exceptional space for larger boats that can be difficult to accommodate in traditional dry storage. Located just minutes from the Venice Jetty and Gulf of Mexico with no bridges to navigate, Gulf Harbor provides outstanding convenience and quick access to open water. Enjoy remarkably low HOA fees of just $399 per month, the same fee charged for every slip in the marina, regardless of size, making this oversized slip an exceptional value. A rare opportunity to own secure, protected boat storage with generous dimensions and an ideal Gulf access location. Currently houses a Robalo 245 which is also available for sale.

100 Circuit Road Unit N116, Nokomis
18050 Wooden Skiff Court, Nokomis
$599,000
2 Beds ⋅ 2 Baths ⋅ Nokomis Sub SubDv. ⋅ 34275 Zip Code
Virtually Staged. Your own private dock, boat lift and Gulf access right in your backyard. Built in 2018, this Key West-style home brings together everything you want in Florida living: newer construction, a peaceful waterfront setting and the freedom to be on the water whenever you want. A private 25-foot dock and 7,000-pound boat lift make it easy to enjoy boating, jet skis, kayaks or paddleboards right from home. From Curry Creek, cruise into Roberts Bay and out to the Gulf of Mexico through the Venice Jetties. Native mangroves create a peaceful and private Old Florida setting along the water. With 1,952 square feet of living space, the home feels open and comfortable throughout. The open floor plan is perfect for relaxed Florida living and entertaining. The kitchen features granite countertops, KitchenAid stainless steel appliances, a breakfast bar and plenty of cabinetry, all open to the great room. Large sliders open fully to the covered lanai, bringing the indoor and outdoor living spaces together. The generous 14' x 11' den gives the floor plan the flexibility of a three-bedroom home, with plenty of room for guests, a home office or additional living space. The split floor plan offers privacy between the primary and guest bedrooms. The primary suite features a large bath with dual sinks, a soaking tub and separate shower, while the guest bedroom offers a comfortable and private space for family and friends. Quality construction sets this home apart, with concrete-block construction, fiber-cement siding, PGT hurricane-impact windows, a metal roof, reinforced two-car garage door and extensive foam insulation throughout the attic and walls. The home is elevated and has never experienced flooding. Located in Cottages on Curry Creek, a gated enclave of just 12 Key West-style homes, lawn care and irrigation are included for easy, maintenance-free living. Whether you're looking for a full-time residence, second home or Florida getaway, this home makes it easy to enjoy the Florida lifestyle. Located in a small gated community, the Legacy Trail is less than half a mile away, with Oscar Scherer State Park, Nokomis Beach, Venice Beach and historic downtown Venice all nearby. Schedule your private showing and come see what makes this home and its waterfront setting so special.

18050 Wooden Skiff Court, Nokomis
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