Osprey/Nokomis Homes with Tennis Court(s) Exterior Features

Osprey/Nokomis Homes with Tennis Court(s) Exterior Features

Welcome to the charming coastal communities of Osprey and Nokomis, nestled in the heart of Sarasota County, Florida. Known for their picturesque landscapes, stunning beaches, and vibrant local culture, these towns offer a unique blend of relaxation and recreation that is hard to resist. Osprey, with its lush greenery and serene waterways, serves as a gateway to the breathtaking beauty of the Gulf Coast. Just a stone's throw away, Nokomis boasts a laid-back atmosphere and some of the best sunsets you’ll ever witness.

For those who appreciate an active lifestyle, homes with tennis courts in this area provide the perfect opportunity to indulge in your favorite sport right at your doorstep. Imagine stepping outside to a private court, where you can practice your serve or challenge friends to a friendly match, all while soaking in the warm Florida sun. These exquisite properties not only offer tennis courts but often feature beautifully landscaped yards, spacious patios, and luxurious outdoor living spaces, making them ideal for both relaxation and entertainment.

Living in Osprey or Nokomis means enjoying the best of both worlds: the tranquility of suburban life combined with easy access to the vibrant arts and dining scene of Sarasota. With pristine beaches just minutes away, you can enjoy everything from sunbathing to paddleboarding. Whether you’re a tennis enthusiast or someone who simply enjoys the charm of these delightful communities, Osprey and Nokomis are the perfect places to call home. Come discover your dream property today!

Newest Osprey/Nokomis Homes with Tennis Court(s) Exterior Features

232 Hidden Bay Drive Unit 303, Osprey
$569,000
2 Beds ⋅ 2 Baths ⋅ Baypointe Vista SubDv. ⋅ 34229 Zip Code
Waterfront resort-style living is behind the gates of Hidden Bay, set along the shores of the Intracoastal Waterway, Little Sarasota Bay, and a tranquil preserve and park in the heart of Osprey. This third-floor residence, accessible by elevator, has been tastefully remodeled and offers two full bedrooms, each with en-suite baths, a spacious den and a three-car garage. The lanai’s exterior sliders open to an all-season, tiled living area where you can enjoy birdwatching and wildlife in the mangroves, observe passing boats, feel gentle bay breezes and take in spectacular sunsets. The wonderfully efficient kitchen features Corian countertops, a breakfast bar with seating for four, new (2025) LG stainless steel appliances and abundant pantry storage within newly outfitted cabinetry, complete with pullout drawers in the kitchen and baths. This beautifully appointed home showcases Acacia engineered flooring, high ceilings, a generous laundry room with newer GE appliances, a sink, tile flooring and ample storage, plus a den or office off the breakfast area. This condominium features a rare three-car garage which includes a private single garage, allowing this space to be used as art studio workshop, or the ever-elusive onsite storage unit along with a separate and spacious two-car garage on the first level. A new roof and updated elevator motor were added in 2025, along with completed Milestone and Reserve studies. Many of the attractive furnishings are available under a separate bill of sale. This exceptional gated waterfront community features a 1,500-foot elevated wooden boardwalk winding through lush landscaping and palm-lined grounds, leading to a private bay front fishing pier. Residents enjoy a renovated clubhouse offering a full kitchen, with granite bar and graciously appointed social area which can be used for private events. Owners also enjoy a fully stocked library, a professional fitness center, and an entertainment and media area. Outside the clubhouse, there is a heated pool, hot tub and tiki hut for additional social gatherings. Hidden Bay is conveniently near restaurants, shopping, Legacy Trail and Nokomis Beach. Osprey is a lovely area between Sarasota and Venice featuring old Florida vibes, peaceful surroundings, and an easy, quiet, lifestyle. Seller willing to lease back.

232 Hidden Bay Drive Unit 303, Osprey
2125 Muskogee Trail, Nokomis
$630,000
3 Beds ⋅ 2 Baths ⋅ Calusa Lakes SubDv. ⋅ 34275 Zip Code
Welcome to paradise in the prominent, gated community of Calusa Lakes! Situated on a private, wooded golf course lot, this spotless, move-in-ready 3-bedroom, 2-bathroom custom home plus dedicated office offers 2,596 sq. ft. of thoughtful living space. Step inside to high ceilings, tile flooring throughout the main living areas, and fresh new carpet in the bedrooms. The expansive great room and formal dining room flow seamlessly into a light-filled kitchen featuring stainless appliances, granite countertops, and a sunny breakfast nook. Your private outdoor oasis awaits! Relax in the resurfaced swimming pool and spa, surrounded by serene, wooded golf course views. The spacious lanai comes equipped with a mini outdoor kitchen with sink, and a convenient outdoor shower and closet. Notable updates and features include a newer tile roof, updated guest bath, a whole-house attic fan, and an oversized 2-car garage equipped with a dedicated workshop area and an 8-foot high double door. Calusa Lakes spans 460 lushly landscaped acres with mature oaks, pines, and 28 lakes. Residents enjoy an 18-hole semi-private golf course with optional membership (no forced dues!), tennis and pickleball courts, low quarterly HOA fees, and NO CDD fees. Just 2 stoplights from Nokomis Gulf beaches & boating, minutes to the Legacy Trail, Sarasota Memorial Hospital Venice Campus, and an easy drive to Venice Island and downtown Sarasota. Schedule your private tour today! Professional pictures coming soon.

2125 Muskogee Trail, Nokomis
250 Hidden Bay Drive Unit 301, Osprey
$695,000
3 Beds ⋅ 3 Baths ⋅ Edgewater At Hidden Bay SubDv. ⋅ 34229 Zip Code
Enjoy sweeping water views and stunning sunsets over Little Sarasota Bay from this spacious third-floor corner residence in the gated waterfront community of Edgewater at Hidden Bay. Built in 2017 and moved into in January 2018, this three-bedroom plus den, 2.5-bath condominium offers nearly 2,200 square feet of living space with easy elevator access and one assigned parking space in the building. The attractive open floor plan features soaring ceilings, impact-rated windows and sliding doors, easy-to-maintain tile plank flooring and abundant natural light throughout. The kitchen includes granite countertops, solid wood cabinetry, stainless steel appliances and custom storage with pullout drawers. The living area opens to a large, screened-in terrace with privacy screens and expansive bay views. The primary suite includes dual walk-in closets and a luxurious bath with dual quartz vanities, decorative tile flooring, a makeup vanity and a walk-in shower. Additional features include a private den/office, an in-unit laundry room, two full baths and a powder room, and air conditioner from 2023. Edgewater at Hidden Bay is a gated, resort-style community set on 14 acres along Little Sarasota Bay and the Intracoastal Waterway, directly across from Casey Key. Community amenities include a waterfront clubhouse with a kitchen and quartz bar, a heated pool and spa, a fitness center, a library, a tiki hut with grilling stations, pickleball and tennis courts, a kayak launch, a fishing pier, a dog play area, and an elevated boardwalk through mangroves and palm-lined grounds. Hidden Bay is conveniently in Osprey, just south of Sarasota, near area beaches, shopping and dining and only minutes from Venice.

250 Hidden Bay Drive Unit 301, Osprey
33 Bishops Court Road Unit 118, Osprey
$679,000
2 Beds ⋅ 3 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
**EXPERIENCE EFFORTLESS LIVING in this BEAUTIFULLY UPDATED TOWNHOUSE with SERENE WATER VIEWS** Located behind the Secure Gates of The Oaks Preserve, Golf & Country Club neighborhood, this delightful residence features 2 En Suite Bedrooms on the 2nd Floor, 2 Full and 1 Half Baths, and offers a refined yet relaxed lifestyle surrounded by mature oak canopies and tranquil lake views. The main living area entails an inviting great room that opens to serene water views framed by palms and natural greenery while the European-style kitchen is thoughtfully designed with premium SubZero, Wolf and Bosch appliances, modern wood cabinetry, polished granite countertops, and durable ceramic tile flooring—ideal for both everyday living and entertaining. Architectural details add warmth and character throughout, including hand-plastered walls with art niches, graceful archways, plantation shutters, and sisal carpeting. Just off the entry foyer, you’ll find a convenient powder room and a separate laundry room. A private brick balcony provides ample space for outdoor dining or relaxing while enjoying the peaceful surroundings. The primary suite overlooks the lake and includes two walk-in closets and a spacious bathroom featuring dual vanities, walk-in shower, jacuzzi tub and appointed with upscale finishes. The guest suite is equally comfortable, complete with built-in shelving and ample storage. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts (4 lighted), 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership.

33 Bishops Court Road Unit 118, Osprey
254 Vinadio Boulevard, Nokomis
$565,000
4 Beds ⋅ 2 Baths ⋅ Toscana Isles SubDv. ⋅ 34275 Zip Code
This gorgeous turn-key Delray model 4-bedroom, 2-bath home features over $85,000 in upgrades and showcases an open floor plan with 9’ ceilings, 8’ doors, elegant wood-look plank tile flooring throughout the entire house, hurricane-impact windows and plantation shutters. Recessed lighting and ceiling fans are found throughout the home. The home’s original skip-trowel textured walls have been professionally refinished to a smooth, seamless finish, creating a clean and updated look throughout the interior. The lanai is enclosed with upgraded no-see-um screens, along with an enclosure kickplate and two fans, making it perfect for entertaining Additionally, a house bib with storage container for a garden hose has also been added. At the heart of the home is the chef’s kitchen, featuring quartz countertops with a quartz full back-splash, added pendant lighting, soft-close cabinetry with roll-out shelves, under-cabinet lighting, and a spacious walk-in pantry with custom shelving— ideal for both everyday living and entertaining. The generous primary suite offers two walk-in closets equipped with custom shelving, an en-suite bath complete with a walk-in shower, dual sinks, custom lighting & mirrors. The countertops are quartz with an upgraded 8” backsplash in both bathrooms. An epoxy-finished garage floor includes custom cabinetry and abundant overhead storage space. Residents benefit from a low HOA that includes lawn and yard maintenance. Living here means embracing an active and vibrant lifestyle in this gated, resort-style, maintenance-free community where you can enjoy kayaking, canoeing, and fishing. The impressive 8,000-square-foot clubhouse serves as the community’s heart and features a state-of-the-art fitness center, a ballroom for social gatherings, and a billiard room equipped with a big-screen TV and an infinity-edge pool. Golf cart-friendly streets throughout the neighborhood. You’re just six miles — a quick 10-minute drive — from the stunning Nokomis Beach and conveniently close to the Legacy Bike Trail. Sarasota Memorial Hospital is only 5 minutes away. The lively downtown areas of Venice and Sarasota are nearby, offering cultural experiences, delightful shopping, and dining options Don’t let this incredible opportunity slip away. Call us today to schedule your private showing and take the first step toward making this dream home your reality.

254 Vinadio Boulevard, Nokomis
718 Sorrento Inlet Drive Unit 718, Nokomis
$335,000
2 Beds ⋅ 3 Baths ⋅ Sorrento Inlet SubDv. ⋅ 34275 Zip Code
BEST PRICE AROUND!!! Live by the WATER without paying the waterfront price! This beautiful, updated home in the sought-after Sorrento Inlet community is sure to please! The 2-story 2225 total sqft town home has been recently renovated to provide modern upgrades. Freshly painted and featuring Brand new Luxury vinyl flooring, stainless steel appliances, and modern cabinetry. New Bathroom updates, fixtures and more! Sorrento Inlet is a low-maintenance community that’s loaded with amenities, including a heated swimming pool with shaded lounge areas, pickleball, tennis, and shuffleboard courts, and onsite restrooms. There are no special assessments and some extremely affrodable dock fees. This is one of the best ways to enjoy true "Boats down the street" living. Located between Venice and Sarasota, the quick access to I-75, local beaches via scenic back roads, and all the shopping, dining, and coastal charm are just a short drive away! This is Low- Maintenace/ Peaceful lifestyle living. Schedule your showing today! DOCK FEES SOME OF THE LOWEST ANYWHERE!

718 Sorrento Inlet Drive Unit 718, Nokomis
5100 Jessie Harbor Drive Unit 404, 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
7204 Jessie Harbor Drive Unit 7204, Osprey
$395,000
2 Beds ⋅ 2 Baths ⋅ Heron House SubDv. ⋅ 34229 Zip Code
**BEAUTIFULLY UPDATED WATERFRONT CONDO WEST OF THE TRAIL! BRING YOUR BOAT & KAYAK FOR DIRECT ACCESS TO THE INTRACOASTAL WATERWAY AND GULF OF MEXICO.** Unlike many Blackburn Harbor residences, this thoughtfully renovated 2-bedroom, 2-bath, second-floor condo is move-in ready, allowing the next owner to immediately enjoy the coveted waterfront lifestyle without the time or expense of major updates. The fully renovated interior showcases an impressive kitchen with quartz countertops, solid wood cabinetry, stainless steel appliances, and CoreTec luxury vinyl flooring throughout (except the guest bedroom). The spacious owner's suite features custom built-in closets and cabinetry, complemented by an elegantly updated en-suite bath. Multiple sliding glass doors open to an expansive screened balcony, where peaceful Florida nature views create the perfect setting to relax and unwind. Located within the secure, gated community of Blackburn Harbor, residents enjoy an exceptional waterfront lifestyle with boat docks (subject to availability), kayak launch and storage, direct Intracoastal access, a community pool, tennis and pickleball courts, fitness center, clubhouse, gazebo with BBQ area, and abundant natural surroundings. Private covered parking and ground-level storage are also included. Ideally situated in Osprey between Sarasota and Venice, Blackburn Harbor is just minutes from nationally ranked Pine View School, the Legacy Trail, Gulf beaches, shopping, dining, and everything the Gulf Coast lifestyle has to offer. RECENT COMMUNITY IMPROVEMENTS INCLUDE: Asphalt paving, irrigation, walkways, walkway lighting, and upgraded lighting for the tennis and pickleball courts.

7204 Jessie Harbor Drive Unit 7204, Osprey
280 Hidden Bay Drive Unit 302, Osprey
$745,000
3 Beds ⋅ 2 Baths ⋅ Edgewater At Hidden Bay SubDv. ⋅ 34229 Zip Code
Move right in and enjoy refined coastal living in this brand-new condominium at Edgewater at Hidden Bay. Offering 1,937 square feet, this thoughtfully designed home features three spacious bedrooms, two stylish bathrooms, and a versatile office—perfect for work or creativity. The sleek kitchen is the heart of the home, complete with premium LG appliances, solid wood cabinetry, and elegant quartz countertops. Sun-filled living spaces are enhanced by large windows with partial views of Little Sarasota Bay, creating a calm and inviting atmosphere. Well-appointed bedrooms and beautifully finished bathrooms provide comfort and style throughout, with high-end details and a seamless, modern layout. Set in the desirable Edgewater community, this home combines upscale living with easy access to scenic waterways and green spaces—offering the perfect balance of luxury and relaxation.

280 Hidden Bay Drive Unit 302, Osprey
51 Macewen Drive Unit 12, Osprey
$275,000
1 Beds ⋅ 1 Baths ⋅ Windsor Lodge At The Oaks SubDv. ⋅ 34229 Zip Code
Situated in Windsor Lodge in The Oaks Clubside, this updated second floor condo has a kitchenette with quartz countertops, a modern bath, a bonus space set up as a small office area and in-unit laundry. An end unit, it has more windows than the typical interior location, filling the interior with wonderful natural light and offering sweeping views of Eagle #18 and lake. This immaculate condo is perfect for hosting out of town visitors, or for you to use as a weekend get-a-way. And, when you are not using it, the flexible rental policy allows you to easily lease the unit. Offered turnkey furnished and with the convenience of the Windsor Lodge pool and clubhouse just steps away, there is no better way to experience The Oaks with little effort and a lot of comfortable, maintenance-free enjoyment.

51 Macewen Drive Unit 12, Osprey
6100 Jessie Harbor Drive Unit 202, Osprey
$798,000
3 Beds ⋅ 4 Baths ⋅ Blackburn Harbor SubDv. ⋅ 34229 Zip Code
One or more photo(s) has been virtually staged. PRICE IMPROVED OVER $50K!!!! Experience elevated coastal living in this beautifully appointed waterfront residence, ideally located within the sought-after Blackburn Harbor community in Sarasota County. Situated on the second floor (building with elevator), this elegant and spacious 3BR + den / 3BA condominium offers over 3,700 SF of a harmonious blend of style and comfort, complemented by serene water views. The open-concept layout features expansive living and dining spaces bathed in natural light, perfect for both everyday living and effortless entertaining. Sliding glass doors lead to a generous wrap-around lanai, creating a seamless indoor-outdoor setting to relax and enjoy tranquil water views, refreshing coastal breezes and spectacular sunsets. The gourmet kitchen is as functional as it is inviting, showcasing rich wood cabinetry, granite countertops, stainless steel appliances, a center island for culinary enthusiasts, and a cozy dinette. A convenient breakfast bar opens to the main living area, ideal for casual dining and social gatherings. The primary suite serves as a peaceful retreat, complete with ample closet space and a well-appointed en-suite bath. Each additional bedroom features its own en-suite bathroom and walk-in closets, offering comfort and privacy for guests or versatility for a home office. Residents of Blackburn Harbor enjoy an array of resort-style amenities, including a heated pool, fitness center, clubhouse, tennis and pickleball courts, kayak storage and launch, and a gazebo with grilling areas. Boating enthusiasts will appreciate the protected deep-water dockage with power and water, and direct access to the Intracoastal Waterway with no bridges. Surrounded by natural beauty, the community provides a front-row seat to Florida’s coastal wildlife, including dolphins and manatees. Just across the street, Oscar Scherer State Park offers scenic trails and outdoor recreation, while nearby waterways invite kayaking adventures to local favorites like Casey Key. Perfectly positioned between Venice (10 minutes) and Sarasota (25 minutes), this location offers convenient access to shopping, dining, and cultural attractions, as well as world-renowned Gulf beaches, including Siesta Key Beach just 15 minutes away. Whether you’re seeking a seasonal escape or a year-round residence, this exceptional property captures the essence of Florida waterfront living.

6100 Jessie Harbor Drive Unit 202, Osprey
Start Your Search

How much is your home worth?

Get instant property value now!