Osprey/Nokomis Homes with Traditional Architectural style

Osprey/Nokomis Homes with Traditional Architectural style

Welcome to the enchanting communities of Osprey and Nokomis, nestled in the heart of Sarasota County, Florida. These charming towns offer a unique blend of coastal beauty, rich history, and vibrant community life, making them an ideal destination for homebuyers seeking a serene yet engaging lifestyle.

Osprey, known for its picturesque landscapes and proximity to the shimmering Gulf of Mexico, boasts a welcoming atmosphere and a tight-knit community. Here, you can explore the scenic trails of the Oscar Scherer State Park or enjoy the tranquil waters of the nearby Casey Key. Just a stone's throw away, Nokomis enchants with its pristine beaches and charming local shops. The area is rich in cultural offerings, with art galleries, seasonal festivals, and delightful dining options that cater to a variety of tastes.

For those captivated by traditional architectural styles, Osprey and Nokomis present an array of stunning homes that embody timeless elegance. These residences often feature classic elements such as gabled roofs, intricate moldings, and spacious porches that invite you to unwind and savor the warm Florida breeze. Whether you’re drawn to a cozy bungalow or a grand estate, the traditional homes in this region reflect the charm of yesteryear while offering modern comforts.

Living in Osprey and Nokomis means embracing a lifestyle filled with outdoor adventures, community spirit, and the beauty of coastal living. Discover your dream home in this idyllic corner of Florida, where tradition meets tranquility, and every day feels like a vacation.

Newest Osprey/Nokomis Homes with Traditional Architectural style

312 Yacht Harbor Drive, Osprey
$2,250,000
3 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Virtually Staged. Directly across the street from one of the most exceptional community-owned marinas on Florida’s west coast, this beautifully renovated waterfront residence offers remarkable views and an extraordinary boating lifestyle in Southbay Yacht and Racquet Club. Recent exterior enhancements include a brand-new tile roof, fresh exterior paint, a redesigned front vestibule with a more modern aesthetic, and updated outdoor lighting at the front of the home. Considered one of the region’s finest private residential marinas, Southbay’s seven-acre deep-water basin accommodates kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet. With six feet of water at mean low tide, the marina offers slips for 175 resident-owned boats. Southbay’s HOA fees are just $218.87 per month, and marina slips remain highly affordable, with water and electric included. With the marina quite literally in your front yard and the charming Southbay neighborhood stretching behind you, this fully renovated residence sits on one of only two waterfront streets in the community. It features three bedrooms, four full baths and a versatile flex space that can serve as an office or fourth bedroom, with beautiful water views from many rooms. Inside, an elegant tray-ceiling entry opens to porcelain plank tile flooring and expansive living spaces filled with natural light from abundant impact-rated windows and sliding glass doors. The beautifully designed entertainment kitchen and breakfast area flow seamlessly into the spacious family and dining rooms, creating a refined yet relaxed setting for everyday living and entertaining. The outdoor living space is equally impressive, with a custom-built pool and spa framed by a panoramic clear-span pool cage, an expansive stone-tile sun deck and generous covered areas for outdoor dining and entertaining. The private primary suite offers double-door access to the pool and spa, plus a luxurious bath with a deep soaking tub, frameless glass shower, dual vanities, large-format tile and two custom walk-in closets with built-in organization systems. Two guest suites each feature a private en-suite bath and custom closets; one enjoys marina views, while the other opens directly to the pool terrace. Additional features include a three-car garage, brick-paver driveway and mature tropical landscaping. Just steps away, the recently renovated Southbay Yacht and Racquet Club clubhouse overlooks the marina and offers a 99-person ballroom with catering kitchen and dance floor, community gathering room with piano and entertainment area, fitness center, card room, library and meeting room. Residents also enjoy a geothermal-heated pool, youth pool, covered waterfront patios, three tennis courts, four pickleball courts, bocce ball, shuffleboard, basketball court, kayak storage, waterfront park, 20 acres of common grounds and five miles of scenic sidewalks. Southbay is golf-cart friendly, with an active social calendar featuring weekly gatherings, seasonal events and a vibrant Power and Sail Club. This is a rare opportunity to enjoy marina views, waterfront living and one of the Gulf Coast’s most beloved boating communities.

312 Yacht Harbor Drive, Osprey
1346 Thornapple Drive, Osprey
$540,000
3 Beds ⋅ 2 Baths ⋅ Willow Bend SubDv. ⋅ 34229 Zip Code
Welcome to Willowbend, where quiet meandering streets of manicured lawns live, and so can you! Well respected Builder, Lee Wetheringon built sturdy homes and this one will not disappoint! Every bell and whistle upgrade! Open your double stained glass front door to the foyer. Views of a peaceful lake and enormous great room greet you! Double tray ceiling has optional lighting feature and adds layers to the already extra, high quality custom built-ins. Taller doors grace the rooms throughout... Dining room is spacious enough for a large dining table. Convenient custom built-in sideboard for seasonal storage or serving pieces! Great room is 'just that', it's big! Sliding doors open to caged lanai and lakeside views. Kitchen is expansive and has a broom closet and pantry! Southern exposure and extremely high ceilings keep this house light and bright. Breakfast area has 3 panels of aquarium glass windows. Take a peek! But wait, there's much more! The master suite is substantial! More than spacious, it offers a peaceful sitting area also overlooking the lake and lanai. There are two walk-in closets! Double sinks in the master bath, along with a garden tub and water closet. Once again, light and bright! The 3rd bedroom, (has a closet), has been turned into an office! Get a lot of work done here! State of art custom cabinetry! Lovely... Bedroom #2 has its own wing with a full bath. This home has gas in place for the water heater, laundry, etc. The laundry room features a gas Fisher-Paykel laundry set and deep sink! Garage also has lots of storage! Community pool and small clubhouse close by! HOA provides all lawn services, to include care of shrubbery. Conveniently located close to both Sarasota and Venice. Willowbend is a short distance to Nokomis Beach, the wonderful waterfront restaurants off Blackburn Point and Laurel Road, Legacy Bike Trail and Historic Marie Selby Spanish Point! Costco is close and so will be the Trader Joes and Whole Market, both of which are being built! This home is special...

1346 Thornapple Drive, 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
256 Sugar Mill, Osprey
$1,399,000
3 Beds ⋅ 3 Baths ⋅ Oaks The SubDv. ⋅ 34229 Zip Code
This beautifully appointed residence sits on a private, well-maintained lot surrounded by grand, colossal oaks and palm trees, delivering the privacy and curb appeal today's buyers are searching for. Step through the front door and feel the difference - soaring tray ceilings, rich crown molding, and tons of natural sunlight set an elegant tone throughout. The gourmet kitchen is the true showstopper, with gleaming stone countertops, solid wood cabinetry, and an open flow into the living and dining areas — perfect for entertaining or unwinding after a day at the club. Retreat to the luxurious owner's suite complete with dual walk-in closets and a private sitting area, while two additional bedrooms offer guests or family their own well-appointed space. Move-in ready and meticulously maintained, this home features updated salt pool equipment, a refreshed kitchen area, and an updated 3-car garage with maintenance-free epoxy flooring. The compulsory membership in The Oaks Club unlocks an unbeatable lineup of amenities. Schedule a viewing today!

256 Sugar Mill, Osprey
17 Bayhead Lane, Osprey
$1,245,000
3 Beds ⋅ 2 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Impeccable is the only way to describe this charming property! This stunning 3 bedroom, 2 bathroom residence has been completely remodeled to create a luxurious yet comfortable, livable home. No detail has been overlooked in the complete renovation, making it truly gorgeous and unique. The interior is incredible and has so many high-end features; tile flooring designed to look like wood, quartzite countertops, a stylish coffee bar, and a beautifully crafted hood vent. The recent addition of an entire deck off to the side of the home enhances the outdoor living space. The deck includes a canopy that extends to cover part of the area, providing shade for the dining table, swinging chair, and grill. Additionally, a hot tub has been added for your relaxation. The home boasts three bedrooms, with one currently being used as an office. The previously enclosed Florida room has been transformed into a spacious family room, perfect for gatherings. The interior design, crafted by a professional, ensures that no detail no matter how big or small has been missed. The property also features a huge yard, the largest in the neighborhood, providing ample space for outdoor activities, and the pièce de résistance, a dreamy view of the pond. Residents enjoy access to a community pool and clubhouse, both within walking distance from the house. Plus, landscape maintenance is included, making it a hassle-free living experience. With mandatory membership, residents can enjoy all the amenities The Oaks offers. There is currently no waiting list for either Golf or Sports/Social membership.

17 Bayhead Lane, Osprey
15336 Isla Palma Lane, Nokomis
$550,000
4 Beds ⋅ 4 Baths ⋅ Palmero/Sorrento Ph I SubDv. ⋅ 34275 Zip Code
Welcome to the intelligently designed, Taylor Morrison-built, four-bedroom, 3 ½-bath, two-story home in the sought-after, gated community of Palmero. The Santa Rosa model boasts soaring ceilings, desirable open concept living, 8-foot doors and an expansive transom window that casts an abundance of natural light throughout the home. The gourmet kitchen is a chef’s dream, showcasing a gas range, quartz countertops, stainless steel appliances and breakfast bar. The dining room position adds to the functionality of daily living, keeping in line with the modern aesthetic, transitioning seamlessly to the great room. Pocketing glass sliding doors lead to the screen-enclosed lanai, inviting the opportunity to entertain alfresco or relax in tranquility. Main level owner’s suite serves as a private retreat featuring a generously sized walk-in closet, en-suite bath with dual vanities, illuminated mirror, frameless walk-in shower and private water closet. The three additional upper-level bedrooms and two baths flank the lofty 14-by-10-foot bonus/entertainment room. This premier community's appealing amenities include a community pool and spa with pavilion and grilling area, basketball court, beach volleyball, nature trail, fire pit, playground and dog park. Conveniently near world-class beaches, downtown Venice, shopping, restaurants, A-rated schools and nearby Legacy Bike Trail. Toss aside the notion of new construction as this meticulously maintained home is move-in ready.

15336 Isla Palma Lane, Nokomis
75 Osprey Point Drive, Osprey
$1,595,000
4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting. A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout. The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer. Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community. Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

75 Osprey Point Drive, Osprey
51 Mac Ewen Drive Unit 14, Osprey
$285,000
1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options.

51 Mac Ewen Drive Unit 14, Osprey
61 Bayhead Lane, Osprey
$1,050,000
3 Beds ⋅ 3 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Thoughtfully Built MAINTENANCE-FREE Court Yard Life Style Home in Bishops Court in the Oaks Preserve Neighborhood. This Rare Unique Home Design Features: 3 Extra Large Bedrooms, 3 Full Baths, Oversized Main Floor Master Suite w/Sitting Room and Door to Private Back Patio, plus a Wall of Sliders Looking out to the Court Yard Pool Area, Tall Ceilings, Large Walk-in Closet w/Built-ins, Brand New Carpeting plus a 5-Piece Master Bath w/Soaking Tub; Formal Living and Dining Room are Open w/Tall Ceilings, Slider to Pool plus a Den/Library Room off the Living Room and Solid Wood Plank Flooring throughout; Open Kitchen w/Granite Counters and Breakfast Room w/Slider to Pool joined by a Family Room w/Fire Place and Solid Wood Plank Flooring; Pool Bath w/French Door, Main Floor Laundry Room w/Sink, Fabulous Upstairs Suite perfect for Guests or Extended Family w/Bonus Room, 2 Guest Bed Rooms w/Jack and Jill Bath; Extensive Crown Molding, Plantation Shutters throughout, (2026) New Interior Paint, Central Vac, Large Side Load 2 Car Garage w/Storage, Newly Resurfaced Pool and Spa in the Screened-in Court Yard Entertaining Area, Court Yard Entry Gate, (2025) Brand New Designer Flat Tile Roof, (2026) NEW Upstairs AC, (2026) New AC Duct Work, (2026) Painted Pool Deck, (2026) Brand New Paver Driveway. WITH A FEW SIMPLE TOUCHES YOU CAN MAKE THIS HOME ABSOLUTELY FABULOUS! Have VISITORS Coming? NO PROBLEM. THIS HOME MAKES THE PERFECT ENTERTAINING OR SEASONAL FLOOR PLAN OFFERING A PRIVATE UPSTAIRS GUEST SUITE! Neighborhood Community Features: Local Community Pool, 24-Hour Secured Guard Gate, Lush Florida Landscaping and Irrigation are all included in the Maintenance Free Living. The OAKS GOLF & COUNTRY CLUB IS ONE OF SARASOTA'S PREMIER EQUITY "Creme de la Creme" GOLF COMMUNITIES! This amazing COUNTRY CLUB Features: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World Golfing (One of America’s Healthiest Clubs), Three Restaurants, Ballroom, Two 18-Hole Championship GOLF Courses, Award-Winning RACQUET Program w/12 HAR-TRU Hydro-Grid TENNIS COURTS, 4 PICKLE-BALL Courts, CROQUET, State of the Art FITNESS Center, Junior Olympic Heated Pool, Bocce Ball and Basketball Court, Playground Area plus so much more! Located just Minutes to the Top Rated Pine View School, Legacy Bike Trail, Florida's Best Coastal Beaches, Restaurants, Shopping and Costco. THE OAKS CLUB MEMBERSHIP IS REQUIRED w/NO WAIT-LIST for SOCIAL or GOLF Memberships. BUYER BONUS: Seller is Offering $80,000 towards Buyer's Capital Contribution Fee for Club Membership Option!!! ***Most Furnishings are Available Under a Separate Contract.

61 Bayhead Lane, Osprey
602 Portia Street N, Nokomis
$439,000
2 Beds ⋅ 2 Baths ⋅ Waterfront Estates SubDv. ⋅ 34275 Zip Code
Waterfront Living with Intracoastal & Gulf Access Discover an exceptional opportunity to create your own waterfront retreat in one of the area’s most desirable coastal settings. Offering 72 feet of canal frontage with Intracoastal and Gulf access, this property presents a rare combination of location, lifestyle, and potential, with room for a boat lift (buyer to verify). Inside, a generous open-concept living area provides an expansive canvas for your vision. Whether you envision a sophisticated coastal retreat, a contemporary sanctuary, or a timeless Florida-inspired residence, the possibilities are truly endless. The thoughtfully designed split-bedroom floor plan offers privacy and comfort, with both bedrooms featuring en-suite bathrooms. Significant improvements provide an excellent foundation for your future plans, including a new roof in 2023, HVAC in 2024, re-piping in 2005, and dock in 2007. Ideally positioned just minutes from Nokomis Beach, shopping, dining, and the new Sarasota Memorial Hospital, this property places the best of coastal living right at your fingertips. A rare opportunity to create a truly personalized waterfront residence with direct access to the waterways and the Gulf beyond. Bring your vision, embrace the possibilities, and make this exceptional waterfront property your own. Seller is ready to consider offers.

602 Portia Street N, Nokomis
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