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

7204 Jessie Harbor Drive Unit 7204, Osprey

215 Carriage House Lane Unit 215, Nokomis
$587,000
3 Beds ⋅ 2 Baths ⋅ Inlets SubDv. ⋅ 34275 Zip Code
Private heated pool • Southern exposure • New pool heater • New A/C • The Inlets gated community Enjoy Florida living at its best in this spacious 3-bedroom, 2-bath pool home located within the highly sought-after gated community of The Inlets. Offering over 2,000 square feet of living space, a 2-car garage, and a private backyard setting, this home is designed for both everyday comfort and effortless entertaining. Pocketing sliding glass doors open to an expansive screened lanai and heated pool, creating a seamless indoor-outdoor lifestyle enhanced by desirable southern exposure and abundant sunshine throughout the day. Inside, soaring cathedral ceilings, plantation shutters, and an open floor plan create a bright and inviting atmosphere. The generously sized kitchen features extensive custom wood cabinetry, stone countertops, a large center island, breakfast nook, and abundant storage and workspace. Travertine flooring flows throughout the main living areas, complementing the home's warm and comfortable design. The spacious primary suite offers private lanai access, dual walk-in closets, dual vanities, a soaking tub, and separate walk-in shower. A split-bedroom floor plan provides privacy for owners and guests alike. Recent improvements include a new A/C system and new pool heater, providing added value and peace of mind. Residents of The Inlets enjoy a vibrant lifestyle with a clubhouse, fitness center, community pool and spa, tennis courts, pickleball courts, shuffleboard, and a full calendar of social activities and events. Ideally located between Sarasota and Venice, this home is just minutes from Gulf beaches, boating, golf courses, the Legacy Trail, shopping, dining, and everything the Gulf Coast lifestyle has to offer.

215 Carriage House Lane Unit 215, Nokomis

116 Woodland Place Unit 116, Osprey
$242,900
2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
Ready to make the move to paradise? Here’s your new home! Adorable two bedroom condo refreshed and ready for a new owner to enjoy convenience living. Crisp and clean with new luxury vinyl in the living room, dining room, hallway and entry, plus just freshly painted! Enjoy a bit of character with the shiplap wood wall in the dining room. Bathrooms have been remodeled with upscale appointments such as cabinetry and showers. Enjoy the spacious rooms with the master bedroom having a walk in closet plus another closet. Each bedroom features its own small balcony - perfect for your morning coffee. The lanai off the livingroom will become a focal point for easy living offering a private wooded back yard area. Kitchen features white cabinets with quartz countertops, tile backsplash and stainless steel appliances. A carport plus two exterior storage closets are also nice benefits. The Pine Run neighborhood is an active community offering many activities including pickleball and tennis. There are two pools - the main pool by the club house and fitness center offers gas grills and a scenic view. The second pool is just a short walk from this condo. Kayak storage is available in the neighborhood with a boat and kayak launch just up the street at the Blackburn Point park. This location offers the best of everything. Located between Sarasota and Venice, you are within easy reach of both. Nokomis Beach is 5 miles away, Siesta Key Beach is 9 miles away! The intracoastal waterway is just up the road leading to the ever popular Casey Key Fish House and Tiki Bar. Many other restaurants, shopping and major roads are close at hand. Come see for yourself what makes this condo and Pine Run so special!

116 Woodland Place Unit 116, Osprey

194 Bella Vista Terrace Unit 26A, North Venice
$479,000
3 Beds ⋅ 2 Baths ⋅ Venetian Golf And River Club SubDv. ⋅ 34275 Zip Code
Welcome to your own slice of paradise in sought-after Venetian Golf & River Club. Ideally on the first floor, this beautifully maintained residence is filled with natural light and enjoys refreshing afternoon breezes, spectacular sunsets and sweeping panoramic views of the golf course, the 14th hole and serene natural preserves. One of the newer buildings (2018) it is designed for comfortable Florida living, the spacious three-bedroom, two-bath floor plan offers a seamless blend of elegance and functionality. The bright kitchen has been thoughtfully updated with freshly painted cabinetry, convenient pullout drawers, a newly tiled island backsplash, upgraded appliances and abundant workspace for entertaining family and friends. The primary suite is a peaceful retreat featuring updated vanity mirrors and light fixtures, while most closets throughout the home have been enhanced with custom closet systems that provide exceptional organization and storage. Additional highlights include a private two-car garage, dedicated laundry room and a layout that lives like a single-family home without maintenance. Beyond your front door awaits one of Southwest Florida's desirable lifestyle communities. Residents enjoy an impressive array of amenities including a private clubhouse with restaurant, six Har-Tru tennis courts, three pickleball courts, a state-of-the-art fitness center, aerobics studio, resort-style pool, separate lap pool, and a popular tiki bar serving food and drinks. Nature lovers will appreciate the scenic boardwalk winding through protected preserves to the Myakka River. Ideally just minutes from Interstate 75, a new state-of-the-art hospital, Gulf beaches, shopping, dining and charming downtown Venice, this exceptional home offers a combination of luxury, convenience and carefree Florida lifestyle you've been dreaming of. Call now to see this wonderful home!

194 Bella Vista Terrace Unit 26A, North Venice

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

289 Holly Bank Avenue, Nokomis
$649,900
4 Beds ⋅ 4 Baths ⋅ Magnolia Bay South Phase 1 SubDv. ⋅ 34275 Zip Code
Under Construction. The two-story front porch welcomes you into the entryway. A secluded guest suite with full bathroom and large walk-in closet is off the main entrance. French doors lead into the home office that offers plenty of natural light. The kitchen features a large island with built-in seating and corner walk-in pantry. The dining area is embraced by a corner of windows and allows access to the backyard covered lanai. The family room boasts tall ceilings. The primary bedroom has three large windows and a tray ceiling. Double doors lead to the bathroom which has dual vanities, a garden tub, glass enclosed shower, and oversized walk-in closet. Upstairs you are greeted by the game room which is surrounded by windows on two sides. Two secondary bedrooms each with walk-in closets and a shared bathroom complete the second level. The home offers ample storage throughout. The laundry room is located off the three-car garage that opens into the drop zone area.

289 Holly Bank Avenue, 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

294 Holly Bank Avenue, Nokomis
$639,900
4 Beds ⋅ 3 Baths ⋅ Magnolia Bay SubDv. ⋅ 34275 Zip Code
Under Construction. Welcoming entryway is embraced by a private guest suite with a full bathroom and a home office with French doors. As you enter the kitchen, you will see a large island with built-in seating space and a corner walk-in pantry. The dining area is embraced by a corner of windows. The family room boasts ample natural light from sliding glass doors that lead to the extended covered lanai. The primary bedroom hosts three large windows. Double doors lead into the primary bathroom, which features dual vanities, a freestanding tub, glass enclosed shower, and an oversized walk-in closet. Upstairs, you are greeted by a game room that overlooks the family room below. Two secondary bedrooms with additional storage and a full bathroom complete the second level. The laundry room is located off the family room. Two-car garage.

294 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

352 Toscavilla Boulevard, Nokomis
$559,000
4 Beds ⋅ 4 Baths ⋅ Toscana Isles SubDv. ⋅ 34275 Zip Code
Experience refined Florida living in this beautifully designed 4-bedroom + den, 3.5-bath home, thoughtfully appointed with upscale finishes and set within a gated community with guard just 5–10 minutes from the beach, where endless sunsets await. Inside, enjoy tall 10-foot ceilings accented with crown molding and tray ceilings, creating a light, open, and elegant atmosphere throughout. Ceramic plank flooring flows through the main living areas, while plush carpeting in the bedrooms adds comfort and warmth. The flexible den is perfect for a home office, media room, or guest space. Designed for seamless indoor–outdoor living, the home features large three-panel sliding glass doors and a screened front entry, allowing refreshing tropical breezes to flow through the house year-round down the wide long main hallway. The layout includes a dedicated pool bath, already in place for your future pool dreams. Step outside of the screened lanai with specialty insect-resistant screens and plumbing for an outdoor kitchen, and become surrounded by lush tropical landscaping on your extended patio with space for grilling—perfect for relaxing, dining, or hosting guests. The home backs up to a dense, exceptionally quiet preserve, offering rare privacy and a tranquil setting where you can still hear birds and frogs, creating a true natural retreat. A whole-home surge protector adds peace of mind. Residents enjoy resort-style amenities including a newly renovated infinity-edge community pool and scenic community lakes perfect for fishing and kayaking for hours of outdoor enjoyment.

352 Toscavilla Boulevard, 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

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
$375,000
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 impact glass windows, 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

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

6100 Jessie Harbor Drive Unit 202, Osprey

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

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

409 North Point Road Unit 401, Osprey
$560,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Nestled at treetop level, in Meridian behind the gates of The Oaks Preserve, you will find this elegant residence waiting for you to make it your own. With a spacious master suite, two guest bedrooms (one en suite) and a den, this condo lives large, with room for comfortable, gracious living. Beautifully appointed, every special touch you would want can be found here, Italian ceramic tile, crown molding, ceiling fans and custom lighting. The expansive kitchen features granite countertops and stainless-steel appliances and has a cozy breakfast nook. Practical concerns are addressed by things like electric hurricane shutters in addition to impact windows and doors, and a large laundry room. Meridian residents have use of their own pool, spa and workout room. And can take advantage of all the Oaks Club has to offer, two championship golf courses, a world-class tennis facility, a state-of-the art wellness center and a wide variety of club amenities, including dining options and social offerings. There is currently no waiting list for either Golf or Sports/Social membership.

409 North Point Road Unit 401, 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

188 Daylily Boulevard, Nokomis
$512,000
4 Beds ⋅ 2 Baths ⋅ Nokomis SubDv. ⋅ 34275 Zip Code
4 Bedrooms and a DEN with Waterview! Tucked away in a private community in Nokomis, this spacious 4-bedroom plus den home offers a thoughtfully designed floor plan that seems to go on and on, creating an open, airy feel far larger than expected. Perfect for both everyday living and entertaining, the layout provides flexibility and comfort in every corner. Step outside to your backyard oasis overlooking a serene pond, where you can relax and take in the natural beauty—including visits from graceful sandhill cranes. Whether enjoying your morning coffee or unwinding at sunset, this setting captures the essence of the Florida lifestyle. With its combination of space, privacy, and picturesque surroundings, this home is a rare opportunity to experience peaceful living just moments from everything Nokomis has to ofer.

188 Daylily Boulevard, Nokomis

14021 Bellagio Way Unit 309, Osprey
$879,000
3 Beds ⋅ 3 Baths ⋅ Villas At Osprey Harbor Village SubDv. ⋅ 34229 Zip Code
Enjoy breathtaking sunset views overlooking the intercostal waterway in this boater's paradise, complete with an on-site marina. Discover coastal living in this beautifully updated 3-bedroom, 2.5-bath residence located in Bellagio Harbor Village. Ideally positioned between Sarasota Big Pass and the Venice Jetty, and just minutes from Midnight Pass and the Gulf of Mexico, this home offers easy access to pristine beaches, fine dining, and boutique shopping. Walkable to local restaurants and boat docks, the community is both conveniently located and peacefully serene. Offering 2,199 square feet of thoughtfully designed living space, this residence has been enhanced for comfort and style. Updates include new lighting throughout, featuring four coastal ceiling fans and elegant Caprice chandeliers. The spacious primary suite and two additional bedrooms feature new cordless blinds and window treatments, creating private and tranquil retreats. Bathrooms have been refreshed with new toilets, fresh paint, and an updated vanity in the powder room. The well-appointed kitchen showcases shaker-style cabinetry and enjoys stunning Intracoastal and sunset views. Step onto the private lanai and enjoy seamless indoor-outdoor living with direct access to the pool area. Newly installed retractable screens provide shade and privacy when desired while preserving expansive water views. Outdoor enthusiasts will appreciate the on-site kayak storage and launch area, perfect for exploring the surrounding waterways. Located in southwest Osprey, this exceptional residence offers both a beautiful home and a vibrant waterfront community. Residents enjoy access to a resort-style pool, hot tub, sauna, and open-concept gathering spaces—creating a lifestyle where every day feels like a vacation.

14021 Bellagio Way Unit 309, Osprey

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

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