Osprey/Nokomis Homes with Traditional Architectural style

Osprey/Nokomis Homes with Traditional Architectural style

Welcome to Osprey and Nokomis, two charming communities nestled in the heart of Sarasota County, Florida. Known for their picturesque landscapes, friendly neighborhoods, and proximity to stunning Gulf Coast beaches, Osprey and Nokomis offer the perfect blend of small-town charm and modern conveniences. With a rich history that dates back to the late 1800s, these areas boast a vibrant cultural scene, abundant outdoor activities, and an inviting atmosphere that makes residents feel right at home.

Osprey is renowned for its lush parks, scenic waterfront views, and historic sites, such as the famous Oscar Scherer State Park, which provides opportunities for hiking, biking, and birdwatching. Just a stone's throw away, Nokomis enchants with its pristine beaches, including the beloved Nokomis Beach, perfect for sunbathing, swimming, and enjoying breathtaking sunsets.

For those captivated by traditional architectural styles, Osprey and Nokomis present a delightful selection of homes that echo the charm of classic design. From elegant Mediterranean villas to cozy craftsman bungalows, these residences embody timeless beauty and craftsmanship. Many homes feature inviting front porches, intricate woodwork, and lush landscaping, creating a warm and welcoming atmosphere.

Living in Osprey and Nokomis means enjoying a laid-back lifestyle with access to local boutiques, delightful dining options, and vibrant community events. Whether you’re strolling along the waterfront, exploring nearby nature trails, or relaxing at a local café, you’ll find that life here is as enchanting as the homes themselves. Discover your dream home in this idyllic slice of Florida, where tradition meets tranquility!

Newest Osprey/Nokomis Homes with Traditional Architectural style

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
$1,270,000
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
101 Osprey Point Drive, Osprey
$4,790,000
4 Beds ⋅ 6 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.

101 Osprey Point Drive, Osprey
4678 Silent Creek Way, Nokomis
$3,995,000
5 Beds ⋅ 4 Baths ⋅ Sorrento East SubDv. ⋅ 34275 Zip Code
Tucked away at the end of a quiet road on a breathtakingly private one-acre homesite, this extraordinary luxury gated estate overlooks the serene waters of South Creek with the untouched natural beauty of Oscar Scherer State Park creating an incomparable backdrop. Completely reimagined with a sophisticated contemporary aesthetic, this custom-built residence blends timeless architecture with high-end designer finishes and luxurious modern upgrades throughout. From the moment you arrive, the home makes a striking impression with its expansive front porch, lush new landscaping, updated driveway and beautiful natural surroundings. Inside, every space has been thoughtfully transformed with premium materials, stylish finishes, and exceptional attention to detail. The result is a home that feels luxurious and inviting with a chic contemporary style rarely found. Featuring five bedrooms and 3.5 baths, the expansive floor plan is designed for both elegant entertaining and comfortable everyday living. Upon entering, stunning views of South Creek immediately draw your attention through the open living spaces and out toward the resort-style outdoor setting. The completely redesigned gourmet kitchen is the centerpiece of the home, showcasing KitchenAid® professional appliances, custom cabinetry, designer lighting, and luxurious finishes throughout. The spacious family room with a built-in electric fireplace flows seamlessly from the kitchen, while the formal dining room, butler’s galley and large walk-in pantry create the perfect setting for upscale gatherings and entertaining. Additional bonus spaces include a large media/game room with flexibility for a home theater, fitness space, billiards room or lounge area. Throughout the home, every detail has been elevated, including new flooring, custom wall accents, designer paint selections, premium fixtures, sophisticated lighting and beautifully renovated baths and living spaces. Anderson windows further enhance the quality and craftsmanship found throughout the residence. Upstairs, two oversized guest bedrooms feature walk-in closets connected by a Jack-and-Jill bath, while built-in desk spaces create ideal work-from-home or study area flexibility. Outdoor living is equally spectacular and has been totally reimagined. The new covered and screened lanai with outdoor kitchen overlooks the newly enhanced pool and spa area featuring a brand-new picture-frame pool cage and elegant paver deck. Beyond the pool, a dock extends toward the peaceful waters of South Creek, where panoramic natural views and complete privacy create a truly breathtaking setting. The dock and creek can accommodate a boat up to approximately 24 feet with direct access to the Intracoastal Waterway and beyond, offering an exceptional opportunity to enjoy boating, waterfront dining, and the waterfront lifestyle directly from your backyard. Completing the property is an oversized three-car garage with abundant space for vehicles and recreational storage along with an additional shed for tools and equipment. A one-year home warranty is included. The home features 69 solar panels that provide electrical service to the entire home and heated saltwater pool. This system is not financed. Private, stylish, luxurious and surrounded by nature, this exceptional waterfront estate offers a rare opportunity to own a fully transformed retreat in one of Nokomis’ scenic and secluded locations.

4678 Silent Creek Way, Nokomis
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
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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