Refine Search
Sort by
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

293 Daylily Boulevard, Nokomis
$538,000
4 Beds ⋅ 3 Baths ⋅ Venice Woodlands SubDv. ⋅ 34275 Zip Code
Four bedrooms plus a dedicated den, 2.5 baths, 2,333 square feet, a peaceful preserve view, and no CDD fee make this 2021 Meritage home in gated Venice Woodlands an exceptional opportunity for buyers looking for space, flexibility, and a newer home near Venice. The single story open concept floor plan features high ceilings and a spacious great room centered around a designer kitchen with a massive quartz island, breakfast bar seating, stainless steel appliances, subway tile backsplash, chic lighting, corner pantry, and abundant cabinet space. Luxury vinyl plank and tile flooring flow through the main living areas for a clean and cohesive look. The private owner's suite offers a huge walk in closet, dual vanities, and a beautifully tiled walk in shower. Three additional bedrooms provide plenty of space for family and guests, while the separate den is ideal for a home office, study, or hobby room. The split bedroom design provides additional privacy and flexibility. Outside, enjoy a spacious private backyard overlooking the peaceful preserve, with fencing permitted for pet owners. Additional features include a block stucco exterior, tile roof, paver driveway, irrigation system, rain gutters, interior laundry room, and two car garage. Venice Woodlands offers gated entry, a community pool, clubhouse, fitness center, pickleball courts, sidewalks, and maintenance grounds. The HOA fee is $280 per month and there is no CDD fee. The home is located in Flood Zone X and is conveniently located minutes from I 75, shopping, dining, Gulf beaches, Venice, and Nokomis. If you have been comparing newer homes and new construction, 293 Daylily offers something increasingly difficult to find at this price. Four true bedrooms plus a dedicated den, generous living space, an established gated community, preserve views, and convenient access to everything the Venice area has to offer.

293 Daylily Boulevard, Nokomis

360 N Point Road, Osprey
$1,445,000
3 Beds ⋅ 4 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Virtually Staged. A unique offering! This like-new, never lived in Spanish mission style home is a rare find. Move in ready and set on a private .63 acre lot in The Oaks Preserve, the open floor plan includes 3 en suite bedrooms and 3.5 baths. Thoughtfully designed, it welcomes you with a circular driveway, porte cochere, and a detached 2 car garage equipped with an electric vehicle charger. Inside, soaring ceilings, neutral tile and wood flooring, recessed lighting, and an electric fireplace create a warm, refined ambiance. Built to current codes with impact glass and a new roof, the home offers peace of mind and the efficiency of modern construction. The chef’s kitchen, with Bosch stainless appliances, a gas 5 burner cooktop, soft close cabinetry, a center island with wine storage, and stylish tile finishes, has a breakfast bar and opens to the dining room. The luxurious master suite features a vaulted ceiling, spacious walk-in closet, and a spa inspired bath complete with freestanding tub, glass enclosed shower, dual vanities, bidet, and exquisite tilework. A central brick paver courtyard provides a private tropical retreat with ample room to add a pool. Sarasota’s premier golf and country club, The Oaks Club’s unmatched amenities include two championship 18-holf golf courses, 12 tennis courts and 4 pickleball courts, the state-of-the-art WellFit Center, a junior Olympic pool, a celebrated social calendar, and a wide array of dining options and recreational activities. There is currently no waiting list for either Golf or Sports/Social membership

360 N Point Road, Osprey

216 Osprey Point Drive, Osprey
$695,000
Oaks The SubDv. ⋅ 34229 Zip Code
One of the last remaining opportunities to build a custom luxury estate in The Oaks Bayside, one of Sarasota’s distinguished private country club communities. Behind 24-hour staffed gates, this generous 25,735-square-foot homesite offers a rare chance to create a custom residence with the builder of your choice in a serene, established setting known for its stately oaks, winding streets, natural beauty and impressive estate homes. The Oaks Bayside is treasured for its peaceful, Old Florida character, with a neighborhood setting along Little Sarasota Bay and beautifully landscaped streets that reflect the elegance and privacy of this exclusive community. Design your dream home in a tranquil environment while enjoying access to the exceptional lifestyle The Oaks is known for. Club amenities include three restaurants, a ballroom, two 18-hole championship golf courses, award-winning racquet programs with 12 Har-Tru hydro-grid tennis courts, four pickleball courts, official croquet green, state-of-the-art fitness center, Junior Olympic heated community pool, bocce, basketball court and playground. The Oaks has earned recognition as a Platinum Club of America, Emerald Club of the World, Distinguished Club of the World and one of America’s Healthiest Clubs. Ideally near nationally ranked Pine View School, the Legacy Trail, world-famous Siesta Key, shopping, dining, cultural venues, entertainment and Gulf Coast beaches, this exceptional homesite offers a rare opportunity to enjoy privacy, prestige and the full country club lifestyle in one of Sarasota’s premier gated communities.

216 Osprey Point Drive, Osprey

211 Rubens Drive Unit E, Nokomis
$239,900
2 Beds ⋅ 2 Baths ⋅ Sorrento Park SubDv. ⋅ 34275 Zip Code
One or more photo(s) has been virtually staged. Welcome to endless sunshine, nature & Nokomis Beach, a coastal jewel in the middle of Sarasota County. This spacious second-floor corner-unit condominium offers a wonderful sense of openness with generous room sizes, split bedrooms, abundant windows throughout & excellent Outdoor Living space with two covered & screened lanais. The large 24’ x 18ft wide’ great room offers far more width & flexibility than a typical condominium floor plan. Sliding glass doors open directly to the expansive rear covered & screened lanai spanning 26 feet with amazing views of the Oscar Scherer State Park Preserve. The front covered & screened lanai is approximately 12’ x 12’ & includes a private laundry room. Both lanais have plenty of room for seating & dining areas! The primary suite includes its own private bathroom & a large walk-in closet. Both bedrooms enjoy views toward the pool area, adding to the light, cheerful, resort-style atmosphere. The kitchen offers newer appliances & a cozy breakfast nook, making this condominium equally suited for full-time living, seasonal use, or a Florida retreat. Low, affordable condo fees add to the appeal, with exterior maintenance & building/master insurance included through the association. The location is outstanding — right in Nokomis, where you can enjoy nearby shopping, grocery stores, pharmacy, dining, boutiques, Ace Hardware, & everyday conveniences. You are also super close to both bridges leading to renowned Casey Key, where waterfront dining, tiki bars, live music with dancing, boating, beaches, & the best of the coastal lifestyle await. The historic Island of Venice is just minutes away & offers something for everyone, including the popular weekly Farmers Market, art shows, boutique shopping, outdoor dining, live music, community events, & the charming walkable atmosphere that has made Venice one of Florida's most beloved coastal towns. The impressive Sarasota Memorial Hospital campus is close by, I-75 is convenient with no red light to the interstate via the expressway, & the location is well positioned for easy access to Sarasota, Tampa, Punta Gorda, & all area airports. Come live on vacation in this terrifically vibrant community & enjoy the lifestyle!

211 Rubens Drive Unit E, Nokomis

298 Holly Bank Avenue, Nokomis
$584,900
4 Beds ⋅ 3 Baths ⋅ Magnolia Bay SubDv. ⋅ 34275 Zip Code
Under Construction. The front porch opens into a welcoming entryway with an extended tray ceiling that embraces the main hallway. A bonus flex room overlooks the front yard right off the front door. A full guest suite with a private bathroom and ample closet space is off the main hallway. The kitchen features an island with built-in seating and walk-in pantry. The dining area flows from the kitchen to the connecting family room which offers plenty of natural light from its sliding glass doors and access to the backyard extended covered lanai. The primary bedroom has a wall of windows overlooking the backyard. Double doors lead into the bathroom which hosts dual vanities, a freestanding tub, glass enclosed shower, two walk-in closets and dual access to the laundry room. Two secondary bedrooms with a shared bathroom complete the home along with ample storage space throughout. The drop zone is located off the two-car garage.

298 Holly Bank Avenue, Nokomis

103 Bishops Court Road, Osprey
$699,000
3 Beds ⋅ 2 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
**LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY** this Charming and Cozy 3-Bedroom, 2-Full Bath home sits on a premium Corner Lot directly across from the Community Pool. Featuring a NEW ROOF, 2-Car Garage, and a Spacious and Private screened lanai perfect for relaxing or entertaining, this home offers comfort and convenience throughout. Situated in Flood Zone “X” for added peace of mind. 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 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.

103 Bishops Court Road, Osprey

702 Fair Winds Drive Unit 702, Nokomis
$309,500
2 Beds ⋅ 2 Baths ⋅ Fairwinds Village SubDv. ⋅ 34275 Zip Code
Hidden treasure in Nokomis just minutes from Nokomis Beach! Great location in the complex with private back yard area. Close to community docks and park facilities, including pool and clubhouse, pickle ball court, dog park, kayak storage and canal access to a saltwater canal just minutes from the Gulf of America's beautiful emerald waters. Fairwinds is so well located that you can walk, bicycle and drive to all the conveniences you may desire every day. This unit has been completely renovated with new kitchen bathrooms and appliances just last year in 2025 including the new barrel tile roof, the home is offered fully furnished and is ready for the discriminating new buyer. Your new home in Fairwinds is very close to the beach, a marina with dry storage slips available and even some for sale. You have two waterfront restaurants to choose from with great sunset views and live music. Pops Tropical Grill and Pelican Alley both with water views! Don't forget Briandi's Italian when you want pizza or pasta and the Paradise Bar & Grill. This is affordable living on the BEST Coast of Florida! All of this is located just about three miles from downtown Venice shops and great restaurants. Like live entertainment? Venice Theater produces some of the best live plays and more. Venice charm and more beaches to enjoy in a friendly neighborhood with regular planed activities. This is easy living where you can enjoy boating, dining and beaches all very close to home! Don't let this freshly remodeled home get away without a careful look see!

702 Fair Winds Drive Unit 702, Nokomis

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

216 Carriage House Lane Unit 216, Nokomis
$535,000
3 Beds ⋅ 2 Baths ⋅ Inlets SubDv. ⋅ 34275 Zip Code
Experience refined Florida living in this sought-after Catalina model within the desired gated community of The Inlets. Thoughtfully positioned on a premier homesite originally selected by the developer for its exceptional privacy and ideal proximity to clubhouse amenities, this residence offers an elegant blend of sophistication, comfort, and effortless indoor-outdoor living. From the moment you enter, soaring volume ceilings and an open-concept design create an inviting sense of space, while upgraded front doors along with expansive windows frame lush tropical landscaping and fill the home with natural light. Gracious formal living and dining rooms set a timeless tone with updated neutral flooring, refined finishes, modern lighting, and a clean, sophisticated aesthetic throughout. At the heart of the home, the beautifully redesigned kitchen showcases new cabinetry, quartz countertops, stainless steel appliances and a generous breakfast nook, all seamlessly opening to the spacious family room and oversized lanai, ideal for everyday living and entertaining. A private guest wing, tucked behind pocket doors, offers exceptional comfort for family and visitors alike, featuring spacious guest bedrooms and a stylishly renovated bath. The serene primary suite is ideally on opposite side of the home, creating a peaceful retreat with direct lanai access, dual walk-in closets, and a beautifully updated spa-inspired bath complete with dual vanities and an oversized walk-in shower adorned with elegant tilework. The tropical landscaping has been thoughtfully curated to enhance beauty and privacy while remaining just moments from the community’s impressive amenities, including a resort-style heated pool and spa, tennis and pickleball courts, bocce, shuffleboard, fitness center and vibrant social activities. Ideally just one mile from Nokomis Beach and only a short drive to charming downtown Venice with its boutiques, cafés, art festivals and year-round events, this exceptional property presents a rare opportunity to embrace the quintessential Florida lifestyle in one of the area’s desirable communities. BRAND NEW A/C 07/26. Schedule your private showing today.

216 Carriage House Lane Unit 216, Nokomis

506 Sun Chaser Drive, Nokomis
$550,000
5 Beds ⋅ 4 Baths ⋅ Magnolia Bay SubDv. ⋅ 34275 Zip Code
Better than brand new and only 2 years old, this energy-efficient San Marino floor plan by Meritage Homes is available now in the heart of Nokomis, located within a gated community for added privacy and peace of mind. What truly sets this home apart, and is rarely found in today’s market, is the combination of 5 true bedrooms, a spacious loft, and a dedicated flex room / home office, a layout that offers a level of space and flexibility most homes simply cannot match. Offering 5 bedrooms, 3.5 bathrooms, and a 2-car garage, this thoughtfully designed home features an open-concept layout with a highly desirable first-floor primary suite. As you enter, you’re welcomed by a versatile flex space and private office, leading into a beautifully appointed kitchen with 42-inch upper cabinets, quartz countertops, an under-mount sink, stainless steel appliances, and a corner pantry with custom wood shelving. The main living areas showcase modern tile flooring, while the primary suite offers plush carpeting, dual vanities, a spacious walk-in shower with seamless glass, and a large walk-in closet. Sliding glass doors open to a covered lanai overlooking a stunning water view with a preserve behind it, creating a private and peaceful setting. Upstairs, the rare layout continues with a large loft ideal for entertaining or additional living space, along with four spacious bedrooms, and two offering large walk-in closets, and two full bathrooms. Additional highlights include a large main-level laundry room, ample storage throughout, all appliances included, and full hurricane impact windows and doors for added peace of mind. Even better, this home is NOT located in a flood zone, meaning most lenders will not require flood insurance, a huge long-term savings. Current homeowner’s insurance is approximately $2,200 per year, which is extremely attractive for a home of this size and age. With an incredibly low HOA of just $150 per year, this home also offers convenient access to I-75 and is just minutes from shopping, dining, and the vibrant downtown areas of Sarasota and Venice. It is also ideally located near some of the area’s top-rated schools including Laurel Nokomis School, Venice High School, and the highly sought-after Gifted Pine View School. Residents of Magnolia Bay enjoy resort-style amenities including a clubhouse, pool, fitness center, pickleball courts, and more. This is your opportunity to own a like-new home with a floor plan and value that are truly hard to find.

506 Sun Chaser Drive, Nokomis

101 Mestre Place, North Venice
$387,000
2 Beds ⋅ 2 Baths ⋅ Venetian Golf & River Club SubDv. ⋅ 34275 Zip Code
Experience the ideal blend of luxury, comfort and serene surroundings in this quality-built WCI Rosa model home, in a tropical setting with stunning water and golf course views. At the end of a quiet cul-de-sac, this maintenance-free home offers peace, privacy, and an exceptional lifestyle. Featuring two bedrooms plus a versatile den and two full baths, this home is designed for both relaxation and functionality. The spacious layout includes large side yards, providing added privacy. The expansive primary suite is a retreat, complete with a walk-in closet, dual sinks, a soaking tub and a separate shower. The beautifully appointed kitchen boasts granite countertops, a gas range, rich cherry cabinets and a charming eat-in area, ideal for casual dining. Throughout the home, you’ll find upgraded tile flooring in the living areas and baths, along with recessed lighting that adds a warm and inviting ambiance. The open great room floor plan is ideal for entertaining or simply enjoying everyday living, offering flexibility to suit any lifestyle. Residents of the Venetian Golf and River Club enjoy access to an array of resort-style amenities, including miles of scenic sidewalks, a nature trail, two pools, tennis courts, pickleball courts, a fitness center, exercise classes, dining options and a lively tiki bar. Golf enthusiasts will appreciate the 18-hole championship course and impressive clubhouse. This residence is conveniently near shopping, Interstate 75, beautiful Gulf beaches, charming Venice, Sarasota Memorial Hospital, Venice location and easy access to Sarasota. Don’t miss your opportunity to own a slice of paradise.

101 Mestre Place, North Venice

97 Sugar Mill Drive, Osprey
$1,950,000
5 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed floor plan with expansive living areas, soaring ceilings, and an abundance of natural light. At the heart of the home is a completely renovated chef’s kitchen, featuring high-end finishes, premium appliances, custom cabinetry, and a seamless flow into the main living and entertaining spaces, perfect for both everyday living and hosting guests in style. Each of the five spacious bedrooms offers comfort and privacy, while the six bathrooms provide ample convenience for family and guests. Recent updates include a brand-new roof, and renovated kitchen, offering peace of mind and long-term value for the next owner. Outdoor living is equally impressive, with tranquil surroundings that capture the essence of Florida living, ideal for relaxing, entertaining, or simply enjoying the natural beauty that defines The Oaks Bayside. Residents enjoy access to The Oaks Club, a private, member-owned country club offering championship golf, tennis, fitness, dining, and a vibrant social lifestyle. Conveniently located near top-rated schools, beaches, dining, and shopping, this home delivers the perfect balance of privacy and accessibility. Experience refined living in one of the area’s most sought after communities, this is more than a home, it’s a lifestyle.

97 Sugar Mill Drive, Osprey

4429 Conchfish Lane, Osprey
$499,999
3 Beds ⋅ 2 Baths ⋅ Casey Key SubDv. ⋅ 34229 Zip Code
Virtually Staged. MOTIVATED SELLER- SPACIOUS 2,000+ SQ FT HOME, UPDATED BEDROOM FLOORING, PRIVATE BACKYARD, COVERED LANAI & 2-CAR GARAGE in The Palms of Casey Key, offering a comfortable layout designed for both everyday living and entertaining. The inviting interior features UPDATED FLOORING THROUGHOUT THE BEDROOMS & CLOSETS with durable tile in the main living areas for easy maintenance. A spacious great room provides plenty of room to gather, while the private primary suite is tucked away at the rear and features DUAL SINKS, SOAKING TUB, WALK-IN SHOWER & GENEROUS CLOSET SPACE. Step outside to the COVERED LANAI & PRIVATE BACKYARD, perfect for enjoying your morning coffee or hosting friends and family. Additional highlights include a 2-CAR GARAGE and a well-maintained community with HOA oversight and nearby amenities. Located JUST STEPS FROM PINE VIEW SCHOOL with easy access to US-41 and I-75, this home puts TOP-RATED SCHOOLS, BEACHES, MARINAS, DINING & SHOPPING within minutes.

4429 Conchfish Lane, Osprey

14021 Bellagio Way Unit 404, Osprey
$999,900
3 Beds ⋅ 3 Baths ⋅ The Villas At Bellagio Harbor Village SubDv. ⋅ 34229 Zip Code
This beautifully remodeled waterfront condominium in Osprey offers a blend of luxury, comfort and coastal living, set directly on Little Sarasota Bay with sweeping tranquil bay views from the fourth floor. Arrive in effortless luxury with an elevator that opens directly into this beautifully appointed condo, creating an exceptional sense of privacy and exclusivity. The residence features three spacious bedrooms and three baths all thoughtfully redesigned with high-end finishes. The modern kitchen has been completely renovated and outfitted with new appliances, Hickory cabinetry and elegant Cambria countertops ideal for everyday living and entertaining. Natural light fills the open living spaces, enhanced by hurricane-rated windows and doors throughout for peace of mind. Go onto the north-facing balcony, equipped with automatic hurricane screens and enjoy serene water views year round. A charming Juliet balcony off the guest bedroom adds an extra touch of architectural character and fresh air access. This unit includes two underground parking spaces, conveniently right outside the elevator for effortless access. Residents enjoy an array of resort-style amenities including a fully equipped fitness center, heated pool, hot tub, sauna and beautifully maintained outdoor spaces. Gather with friends at the outdoor cooking areas, relax by the fire pit, or take advantage of the kayak launch and sunset dock for unforgettable evenings on the water. A welcoming clubhouse provides additional space for socializing and events. Ideally between Sarasota and Venice, this property offers quick and easy access to pristine beaches, scenic parks, the Legacy Trail, top tier medical facilities, a wide selection of fine dining and shopping. This is a rare opportunity to own a move-in ready waterfront condominium that captures the essence of Florida Gulf Coast living. Schedule your private showing today!

14021 Bellagio Way Unit 404, 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

51 Macewen Drive Unit 5, Osprey
$235,000
1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.

51 Macewen Drive Unit 5, 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

14041 Bellagio Way Unit 214, Osprey
$700,000
3 Beds ⋅ 2 Baths ⋅ The Villas At Bellagio Harbor Village SubDv. ⋅ 34229 Zip Code
Waterfront Sanctuary-Boater's Paradise at the Osprey Harbor Village- 3 Bedrooms | 2 Bathrooms | Direct Intracoastal Frontage Rare opportunity for direct Intracoastal living at Villas at Osprey Harbor Village (formerly Bellagio Harbor Village). This 3 bedroom, 2 bath residence offers approximately 1,862 sq. ft. of light filled living space with views of the canal, Little Sarasota Bay and Intracoastal Waterway. The open concept design features 9’5” tray ceilings, impact windows and doors, and solid wood cabinetry, granite countertops, kitchen island, and kitchen island bar—ideal for entertaining, anchored by a neutral, airy palette with timeless finishes. The split bedroom layout provides privacy, with a spacious primary suite featuring a spa style bath, separate tub and shower, and direct access to an oversized 270 sq. ft. waterfront balcony from the bedroom. Each window is a curated lens, framing the hues of the Bay and the sculptural silhouettes of architectural lines of Mediterranean inspired Villas. Days here are defined by the rhythmic play of light reflecting across the water and the silent flight of ospreys, eagles, and pelicans—a true haven for the bird watcher seeking a quiet refuge. Whether you are hosting a sunset gathering on your private balcony or entertaining your guests at the community terrace, the club room or embarking on a day of boat excursion to the newly opened Midnight Pass, the lifestyle here is one of effortless coastal elegance. Community amenities include a deep water harbor marina with wet and dry slips, resort pool, clubhouse, fitness center, hot tubs, kayak storage, and launch. Centrally located between Sarasota and Venice, and minutes from Venice, Nokomis, Siesta Key, and Casey Key, Oscar Scherer State Park, Spanish Point, Legacy Trail, and cultural and retail amenities of Sarasota. With new metal roof, exterior and interior paint completed in 2025, this property stands as a resilient sanctuary of enduring value. For the resident who values privacy, prestige, and the restorative power of nature, this is the definitive Osprey address. Schedule your private tour today.

14041 Bellagio Way Unit 214, Osprey

1527 Buoy Lane, Osprey
$1,100,000
3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilings. 2026 AC unit, 2024 tile roof, 2023 driveway, cabinets, lighting, appliances, tile and carpet are just the beginning. 2023 pool and spa led lighting, Pentair controller, saltwater conversion, and owned 250 gallon propane. Dry bar with ice maker, wine fridge, and beverage fridge. Large covered outdoor living space overlooking the large lanai with tv, private tanning area, and room to entertain. A split bedroom design, game room with space for billiards table, and separate dining area, and great room surround the private courtyard layout designed to entertain. Ample storage throughout including an air conditioned, secure 12x7 storeroom. Southbay Yacht and Racquet Club offers a clubhouse, tennis, pickleball, basketball, shuffleboard, playground, and low fee, exclusive dockage for residents in the deep water marina. Frequent community activities provide opportunities for an active social atmosphere from cruises to sports.

1527 Buoy Lane, Osprey

140 Inlets Boulevard Unit 140, Nokomis
$450,000
2 Beds ⋅ 2 Baths ⋅ Inlets SubDv. ⋅ 34275 Zip Code
Bring your boat and enjoy the ultimate canal-front lifestyle. This well-maintained home, lovingly cared for by the same owners for 29 years, is located in the highly desirable community of The Inlets in Nokomis, just one mile to Nokomis Beach. Offering two spacious bedrooms, two baths and an open-concept layout, the home features soaring ceilings in the living and dining areas, creating a bright and airy feel. The kitchen is both functional and inviting, complete with Corian countertops, newer appliances and seamless flow into the dining room, family room and oversized lanai with floor to ceiling acrylic windows, perfect for entertaining while taking in peaceful canal views. The guest bedroom has been thoughtfully transformed into a flex space, with built in Murphy bed, desk and loads of cabinets providing ample storage in keeping with a clean aesthetic. Additional highlights include a new A/C installed in 2025, whole house surge protection, a durable metal roof with the look of tile, hurricane shutters and a whole-house generator with a buried 500-gallon propane tank for added peace of mind. Plantation shutters and neutral finishes throughout provide a wonderful opportunity to personalize the space to your own taste. Enjoy the convenience of taking your golf cart to head to the beach or nearby shopping and dining or taking your own boat out for a short sunset cruise to the Gulf. The Inlets is a gated, active and social community located close to beaches, dining, the new Sarasota Memorial Hospital and quaint downtown Venice. Community amenities include a resort-style pool and spa, tennis and pickleball courts, shuffleboard, bocce and a fitness center. Monthly fees cover ground maintenance, exterior insurance, cable and internet. Don’t miss this fantastic waterfront opportunity. Your Florida lifestyle awaits.

140 Inlets Boulevard Unit 140, Nokomis

133 Bella Vista Terrace Unit 32C, North Venice
$529,000
3 Beds ⋅ 2 Baths ⋅ Venetian Golf & River Club SubDv. ⋅ 34275 Zip Code
Virtually Staged. Impeccable Second-Floor Carriage Home in the Venetian Golf & River Club. Welcome to this beautifully maintained and lightly lived-in Monaco floor plan, offering 2,326 square feet of thoughtfully designed living space in the highly sought-after Venetian Golf & River Club. This second-floor carriage home showcases exceptional attention to detail with custom upgrades throughout. Enjoy modern tile flooring, new luxury vinyl flooring in bedrooms, elegant crown molding, plantation shutters on all windows, and stylish custom lighting and ceiling fans that enhance the home’s comfortable ambiance. The spacious split-bedroom layout features 3 bedrooms plus a versatile den, 2 full bathrooms, a separate laundry room, and multiple oversized closets. Storage is abundant, including generous interior space and a two-car attached garage with additional attic storage. At the heart of the home, the open-concept kitchen is perfect for entertaining, featuring granite countertops, wood cabinetry, and stainless-steel appliances. The seamless flow into the living and dining areas creates an inviting space for gatherings or relaxed everyday living. Embrace the ease of maintenance-free living, with the exterior of the home fully maintained by the association. Impact-resistant windows and sliding glass doors provide added peace of mind. For ultimate convenience, the home is equipped with a private elevator—making second floor living effortless and accessible. Step outside to your private screened lanai, where you’ll enjoy tranquil lake views with a fountain, breathtaking sunsets, and a peaceful, private setting—perfect for morning coffee or evening relaxation. Residents of the Venetian Golf & River Club enjoy a secure, gated lifestyle with an impressive array of amenities. The community borders the scenic Myakka River and features a 70-acre nature park. Optional membership is available for the 18-hole, par-72 championship golf course. Additional amenities include six Har-Tru tennis courts, 3 pickleball courts, a life-style director, a fitness center, exercise studio, resort-style pool and lap pool, the River Club, tiki bar, and a beautifully renovated full-service banquet facility. Ideally located near Sarasota Memorial Hospital, I-75, Gulf Coast beaches, and the charming downtown areas of Venice and Sarasota, this home offers both convenience and an exceptional Florida lifestyle. Schedule your private showing today—this one won’t last!

133 Bella Vista Terrace Unit 32C, North Venice

216 Fair Winds Drive Unit 216, Nokomis
$250,000
2 Beds ⋅ 2 Baths ⋅ Fairwinds Village SubDv. ⋅ 34275 Zip Code
Located just ½ mile from the beautiful sands of Nokomis Beach, this villa offers an opportunity to enjoy the Florida coastal lifestyle in Fairwinds Village, a pet-friendly 55+ community. The home has been partially renovated and features spacious bedrooms, neutral finishes, a bright kitchen, and an open-concept living area. A standout feature is the private boat slip, offering convenient access to the water and adding to the appeal of this coastal location. Community amenities include a clubhouse, swimming pool, canoe launch, and spacious park-like grounds. With the beach, waterways, and local amenities nearby, this property offers a comfortable setting for full-time or seasonal living.

216 Fair Winds Drive Unit 216, Nokomis

243 Cassano Drive, Nokomis
$420,000
3 Beds ⋅ 2 Baths ⋅ Nokomis SubDv. ⋅ 34275 Zip Code
Short Sale. SHORT SALE - SOLD AS/IS - SUBJECT TO 3RD PARTY APPROVAL. This stunning water view home in the highly desirable Neal Community of Milano is a must see! The Anthem II is a well thought out floorplan consisting of 3 bedrooms, 2 full bathrooms and a den. The kitchen is highlighted by solid wood cabinets with crown molding, under cabinet lighting, tastefully tiled backsplash, stainless steel appliances, quartz countertops, closet pantry and a large island. The adjoining dining area and great room are perfect for entertaining or for quiet evenings at home. The den features recessed lights and large windows for a nice bright space that can be used for a variety of purposes. The owners suite showcases a large walk-in closet, ensuite bathroom with large glass enclosed walk-in shower and dual vanities. The two guest bedrooms share a guest bath which features a tub/shower combo. The extended covered lanai with long lake views is the perfect spot to enjoy your morning coffee or to wind down your day with an adult libation. Additional features of this home include; garage extension of 4 feet making it 24 feet deep, IMPACT RESISTANT WINDOWS AND DOORS, additional insulation in the walls, and crown molding in most rooms. Milano has low HOA fees and no CDD yet has an abundance of amenities for its residents to enjoy including; pickleball, bocce, pool, hot tub, dog park and a pool-side fire pit. Milano is centrally located with easy access to I-75, downtown Venice, the beautiful gulf beaches, the Atlanta Braves spring training facility and many dining and shopping options.

243 Cassano Drive, Nokomis

204 Crown Point Drive, Nokomis
$179,900
2 Beds ⋅ 2 Baths ⋅ Kings Gate Club SubDv. ⋅ 34275 Zip Code
Welcome to easy Florida living at 204 Crown Point in Nokomis! Located in a gated, amenity-rich community where the lifestyle truly shines. Bring your boat, RV, fishing pole, and flip-flops. Whether you’re escaping the cold or planning to enjoy Florida year-round, this is the perfect place to call home. You’ll own your own land with low HOA fees, a rare and valuable bonus. This 2-bedroom, 1.5-bath home features a 1989 mobile frame that was completely re-imagined, reconfigured, and rebuilt in 2023, you would think it was built new. Enjoy cathedral ceilings, an open floor plan, and a light, bright interior that feels modern and welcoming. Partially furnished for convenience and move-in ease. Don't miss out, now is the time.

204 Crown Point Drive, Nokomis

3621 N Point Road Unit 301, Osprey
$525,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Ready to live a stress-free luxury condo lifestyle? There is no place better to do it than this 3 bedroom, 3 bath residence in Meridian at The Oaks Preserve. Nestled among the treetops, this end unit has a split floor plan and absolutely breathtaking sunset views over the Preserve and out to Little Sarasota Bay. Natural light floods the interior, highlighting the beauty of the hand-rubbed walnut floors. The kitchen with high-end stainless-steel appliances including a subzero refrigerator, has a breakfast bar, room for a café table and overlooks the dining room. The master bedroom has two large walk-in closets, a spacious en suite bathroom with separate shower and soaker tub. A sliding door to the screened balcony allows you to enjoy your morning coffee as the soothing sounds of awaking nature surround you. The additional 2 en suite bedrooms allow for room and privacy for guests and your loved ones. This well maintained unit has many other features, a large laundry room with utility sink and a good number of cabinets for storage, electric hurricane shutters, ceiling fans, plantation shutters and more. The Meridian residents-only pool, spa and workout room are just steps away. The Oaks, Sarasota’s finest golf and country club, has 2 championship 18-hole golf courses, 12 HAR TRU tennis courts (4 lighted), 4 pickleball courts, a Wellfit Center, 3 onsite restaurants, and a wide variety of social and recreational activities. The location, in the heart of Osprey, is superb. Just a short drive to almost anything you would want or need while living a maintenance-free lifestyle on Florida’s beautiful Gulf Coast. There is currently no waiting list for either Golf or Sports/Social membership.

3621 N Point Road Unit 301, Osprey

401 N Point Road Unit 1001, Osprey
$1,995,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
**Rarely available 10th-floor penthouse corner residence offering 3,029 square feet with sweeping Gulf and Bay views.** Ideally situated behind the secure gates of the highly sought-after Preserve neighborhood within The Oaks Country Club, this exceptional condo features 3 Bedrooms plus Den, 3 Full Baths, Private 2-Car Garage, and climate-controlled storage. The open-concept floor plan is designed to maximize the breathtaking vistas, with panoramic views from the great room, dining area, kitchen, owner’s suite, and expansive balcony. Interior highlights include 10ft ceilings, crown molding, engineered hardwood and tile flooring throughout, and plantation shutters. The well-appointed kitchen offers newer Cambria quartz countertops (2022), solid wood cabinetry, counter seating, and newer stainless-steel appliances (2023). The spacious primary suite features walk-in closets and a luxurious bath with dual vanities, a custom-tiled shower, and a soaking tub. Residents enjoy private amenities including a heated pool and spa, fitness center, and outdoor grilling area, along with full access to The Oaks Club’s renowned lifestyle amenities. Meridian Tower #3 also features a new roof (2025). 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 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. **Please Enjoy Viewing the 3D VIRTUAL TOUR**

401 N Point Road Unit 1001, Osprey

229 Laurel Hollow Drive Unit 83, Nokomis
$415,000
3 Beds ⋅ 2 Baths ⋅ Laurel Hollow SubDv. ⋅ 34275 Zip Code
One of the largest square foot properties in Laurel Hollow sitting directly on the lake with nature preserve views and overlooking the fountains and waterfront gazebo. Approximately 80 ft of lakefront for your private enjoyment. Sitting in the oversize 28 x 17 Florida room (with hurricane windows} makes it feel like you’re sitting over the water. This 3-bedroom 2 bath 2 car garage property has 2000 sq ft of living area under roof. Entering the property there is a large paver patio with a screened lanai entry. As you come into the home there is the main living area / dining room combo which connects you to the kitchen and Florida room. There are wood floors throughout most of the home. In the kitchen there is even room for a breakfast table, the window over the sink allows natural light and views of the lake. The primary suite (17 x 12) has a large walk-in closet, and a walk-in shower. Two additional bedrooms are both (12 x 11) with a shared bath. The 2-car garage has extra storage closets, a work bench and a sliding screen garage door panel. The lakefront Clubhouse has a beautiful heated pool, entertaining areas and a kitchen space, and it is just a great place to meet your neighbors and enjoy the views. This is a great community for a golf cart, you can easily travel to beautiful Nokomis Beach, Casey Key, the Venice Jetty and many restaurants, such as Pop’s tiki bar, Pelican Alley, Paradise Grill and many others. Also, there is a Publix, Aldi, CVS, and banking close by. Easy access to interstate 75 and the new Sarasota Memorial Hospital, 10 minutes to Downtown Venice with it's many shops, theater, beaches and private airport. 25 Minutes up to Sarasota. Great location for whatever you need. You won't be disappointed..

229 Laurel Hollow Drive Unit 83, Nokomis

385 N Point Road Unit 304, Osprey
$1,100,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
**MAGNIFICENTLY UPDATED, EXPANSIVE CORNER CONDO RESIDENCE OFFERING NEARLY 2,800 SQ FT OF REFINED LIVING SPACE** features 3 Bedrooms, 3 Full Baths, PLUS a Study/Den (or optional 4th bedroom with walk-in closet), all nestled behind the secure gates of the highly sought-after Oaks Preserve Country Club community. Step off your private elevator foyer into a brilliantly renovated, light-filled interior designed to impress. Premium upgrades include engineered hardwood and tile flooring, a spectacular chef’s kitchen with quartz countertops and high-end appliances, crown molding, and beautifully updated bathrooms throughout. The owner’s suite showcases serene views, private balcony access, a spacious walk-in closet, and a stunningly redesigned spa-inspired primary bath. Enjoy breathtaking western sunset views from the oversized balcony—perfect for relaxing or entertaining. Additional highlights include a climate-controlled storage unit and one covered parking space. Meridian I offers exceptional value with a new roof (2024) and new elevators (2025/2026 – in progress). Residents enjoy private amenities including a heated pool and spa, fitness center, and outdoor grilling area, plus full access to The Oaks Club’s renowned amenities. A must-see residence combining luxury, space, and lifestyle. 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.

385 N Point Road Unit 304, Osprey

How much is your home worth?

Get instant property value now!