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 are perfectly situated along the stunning Gulf Coast, offering residents a delightful blend of natural beauty, rich history, and a vibrant lifestyle.

Osprey, known for its lush landscapes and serene waterways, is a haven for nature lovers and outdoor enthusiasts. With its proximity to the breathtaking Oscar Scherer State Park and the tranquil shores of Casey Key, residents can indulge in a variety of recreational activities, from kayaking to hiking. Nokomis, on the other hand, boasts a quaint, small-town feel with beautiful beaches and a welcoming community atmosphere.

The real estate market here is equally captivating, particularly for those who appreciate traditional architectural styles. Homes in Osprey and Nokomis often feature classic designs that embody the charm of Florida’s coastal living. Picture yourself in a beautifully crafted home with elegant gabled roofs, spacious porches, and intricate woodwork, all set against the backdrop of swaying palm trees and vibrant gardens. These traditional homes not only exude character but also provide a warm and inviting atmosphere, perfect for families and individuals alike.

Whether you’re seeking a peaceful retreat or an active lifestyle, Osprey and Nokomis offer a unique blend of coastal charm and traditional elegance. Explore the possibilities of making this beautiful region your home, where every day feels like a vacation in paradise. With its rich history, stunning landscapes, and beautiful homes, Osprey and Nokomis are truly a slice of Florida heaven.

Newest Osprey/Nokomis Homes with Traditional Architectural style

$1,900,000
5 Beds ⋅ 8 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Virtually Staged. A rare canvas of luxury, positioned on a lush double lot within the sought-after, gated community of The Oaks, in Osprey, adjacent to stunning Sarasota, known for the arts. Bordering the Heron Course on the eighth fairway, this iconic two-story estate boasts incredible opportunity for limitless potential. The entire interior is freshly painted, to enhance vision of stateliness. With five bedrooms, 7.5 baths and a sprawling layout, this magnificent property is an exceptional backdrop, just waiting for your personal touch. Arrive in style via the elegant front circular driveway or utilize the private rear driveway leading to a rare four-car garage. Inside, the home is masterfully designed for grand entertaining and everyday comfort, with a sweeping curved stairway at the entrance, setting the stage to an exquisite residence. The first floor features a formal living room and a sun-drenched family room complete with a fireplace, custom built-ins and multiple French doors, leading to the outdoor bliss. A screened lanai lays the foundation for Florida living at its finest, showcasing an enormous 33-by-46-foot sparkling heated pool and spa, expansive patio and an outdoor kitchen. The expansive open kitchen is a chef's dream, flowing seamlessly into a casual breakfast nook. For formal affairs, the large dining room offers custom cabinetry and an adjacent wet bar. The main-floor primary retreat is a sanctuary, featuring a dedicated sitting area and luxurious dual en-suite baths. There is more closet space than a clothes diva could possibly desire. The first floor is completed by a handsome office/library with built-ins, a powder room and a guest bedroom. Upstairs, you will find three additional en-suite bedrooms, one of which benefits from private back-staircase access, ideal for an au pair, in-laws or VIP guests. With every bedroom featuring its private bath, privacy is guaranteed for all. Outdoors, the walled double lot provides a private tropical oasis, all with tranquil, serene views. On a practical note, roof was replaced in 2019, with hurricane shutters, for peace of mind. Two 18-hole championship golf courses, 12 Har-Tru tennis courts (four lighted), croquet and pickleball courts, a state-of-the art fitness center, fine and casual dining options and a calendar of social events, The Oaks is Sarasota’s leading golf and country club.

916 Macewen Drive, Osprey
$795,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
INCREDIBLE OPPORTUNITY AND A MUST SEE AT THE MERIDIAN AT THE OAKS - GREAT PRICE, BAY VIEW, UPDATED KITCHEN, PRIVATE 2 CAR GARAGE AND MORE! Beautifully updated and thoughtfully designed, this exceptional 5th floor residence in The Meridian at The Oaks Preserve offers tranquil water and preserve views, a fantastic floor plan, and the rare convenience of a private 2-car garage just steps to the elevator lobby. The expansive split-bedroom floor plan includes 3 bedrooms, 3 full baths, and a private den/study/office that can easily function as a 4th bedroom, providing exceptional flexibility for both everyday living and visiting guests. Filled with natural light, the spacious great room and dining areas flow seamlessly to the generous terrace with upgraded ceramic tile, where peaceful water and preserve views create a serene backdrop for relaxing or entertaining. The custom kitchen, redesigned in 2023, is both elegant and functional, featuring soapstone countertops, Bosch appliances, roll-out cabinetry, Everpure water filtration, a tray ceiling, and detailed crown molding. The primary suite is a private retreat, offering picturesque water views, a custom-designed walk-in closet, and a beautifully appointed bath with Italian tile, dual vanities, and stunning stone countertops. Custom built-ins, upgraded closet systems, and a thoughtfully designed laundry room further enhance the home's comfort and functionality. Residents of The Meridian enjoy lushly landscaped grounds, winding pathways, a community pool and spa, fitness center, and outdoor grilling area. Membership in The Oaks Club is required, providing access to one of Sarasota's most distinguished private club lifestyles, including two championship golf courses, 12 Har-Tru tennis courts, pickleball, croquet, a state-of-the-art wellness center, resort-style pool, multiple dining venues, a vibrant social calendar, and an elegant clubhouse. Ideally located near Historic Spanish Point, Pine View School, Siesta Key Beach, and downtown Sarasota, this exceptional residence offers a rare combination of luxury, privacy, natural beauty, and resort-inspired living.

401 N Point Road Unit 504, 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
$644,900
3 Beds ⋅ 2 Baths ⋅ Toscana Isles SubDv. ⋅ 34275 Zip Code
**Move in Ready! Being Sold Fully Furnished!!** COMPLETELY BRAND NEW HVAC SYSTEM OVER $10K, JUST INSTALLED! ** This bright, open-concept home offers stunning water views from the moment you walk through the door! Nestled within the serene, picturesque community of Toscana Isles, this beautifully appointed 3-bedroom, 2-bathroom single-family home with a versatile den offers the kind of Florida lifestyle most only dream about! Sweeping panoramic lake views greet you from the moment you step inside, where soaring high ceilings and oversized windows flood the spacious living room with warm, natural light — creating an atmosphere that feels both grand and instantly inviting. The modern kitchen is thoughtfully equipped with contemporary appliances and generous counter space, flowing seamlessly into a warm dining area perfectly sized for family gatherings and entertaining guests. The primary suite is a true retreat, featuring an en-suite bathroom complete with a luxurious soaking tub that makes unwinding at the end of the day feel effortless. Both guest bedrooms are comfortably spacious, each outfitted with trundle beds to accommodate extra guests with ease, while smart televisions — installed throughout the home and even outdoors — add a polished, connected touch to everyday living. The flexible den, currently configured as a fourth bedroom, gives you options that most comparable homes simply don't offer, and plentiful built-in storage throughout means every inch of this home works as hard as it impresses. Step outside and Toscana Isles delivers resort-style living right at your doorstep — a sparkling infinity pool, a stunning lakeside clubhouse, tennis courts and fully equipped fitness center. And when the beach calls, you're less than 15 minutes from the soft, sandy shores of Florida's coastline, giving you the rare combination of peaceful lakefront serenity and effortless coastal access. This is the home who want it all — space, style, community, and location — without compromise!

228 Maraviya Boulevard, Nokomis
$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
$839,000
3 Beds ⋅ 2 Baths ⋅ Calusa Lakes SubDv. ⋅ 34275 Zip Code
On the largest homesite within the Calusa Lakes community, this residence captures serene preserve, water and golf course views from a private setting designed for everyday comfort and entertaining. Beyond the double-door entry, expansive arched picture windows, French doors and elevated ceilings fill the interior with natural light. Crown molding and chair rail detailing enhance the formal living and dining rooms, while the open-concept kitchen flows seamlessly into the family room and breakfast area featuring an aquarium window overlooking the outdoor living space. The multi-level screened lanai offers a pool, spa, outdoor shower and generous areas for relaxation surrounded by mature landscaping and tranquil scenery. The primary suite is privately positioned apart from the guest wing and includes an en-suite, two walk-in closets an adjoining office, creating a peaceful retreat for work and relaxation. The elegant gated entrance and mature landscaping enhance the atmosphere of Calusa Lakes with it's golf course, pickleball/tennis and casual clubhouse dinning. This meticulously maintained home is an exceptional opportunity within the sought-after community

2120 Muskogee Trail, Nokomis
$4,795,000
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
$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
$549,000
3 Beds ⋅ 2 Baths ⋅ Calusa Lakes SubDv. ⋅ 34275 Zip Code
Beautiful Calusa Lakes home with a tranquil setting with an open greenbelt area with the 16th fairway of the popular golf course behind. The sought-after gated golf community of Calusa Lakes is a beautiful neighborhood to call home. The home has three bedrooms, two baths and a den off the primary bedroom with a split plan for the bedrooms. The den could be used as a fourth bedroom and has a closet. THE TILE ROOF WAS JUST REPLACED IN 2026 FOR PEACE OF MIND. The home has 2,505 square feet of living area and the ceilings are high with a lot of windows for natural light and enjoying the views. The large primary bedroom has two walk-in closets and a spacious en-suite bath with dual vanities, and Roman tub with a separate walk-in shower. Both guest bedrooms have walk-in closets for added storage. The kitchen is spacious with lots of cabinets and counterspace with a built-in desk area. There is a dinette with a large aquarium window bringing in the outside. There is a welcoming lanai off the back of the home for relaxing. The garage is big, boasting width of 27 feet for extra storage and to accommodate a golf cart. Calusa Lakes offers many social activities, golf, tennis and clubhouse with pro-shop and restaurant. The lots are large compared to most subdivisions and there are extensive landscaped and natural common areas throughout. Calusa Lakes golf membership (optional) also includes options to have privileges to play Capri Isles and Waterford courses. The popular Nokomis Beach is less than a 15-minute drive as well as many restaurants and shops.

2139 Calusa Lakes Boulevard, Nokomis
$479,900
2 Beds ⋅ 2 Baths ⋅ Waterfront Estates SubDv. ⋅ 34275 Zip Code
Enjoy serene waterfront living with 72 feet of canal frontage, Gulf access, and an existing dock, with room for a boat lift (buyer to verify). With easy access to the Intracoastal Waterway and the Gulf, this property is a dream for boating enthusiasts. The spacious home features a family room overlooking scenic Shakett Creek, offering a peaceful, ever-changing water view. An open floor plan with dual master suites provides flexibility for guests or multigenerational living. The kitchen includes an eat-in space, complemented by a formal dining area ideal for entertaining. Recent updates include a new roof (2023), new HVAC (2024), new water heater (2024), refrigerator (2024), and stove (2022). Conveniently located near the hospital, shopping, and many restaurants. Waterfront homes like this are hard to find—bring your decorating touches and create the waterfront lifestyle you’ve been dreaming of. Schedule your private showing today and experience the beautiful, relaxing water views for yourself.

602 Portia Street N, Nokomis
Start Your Search