3621 N POINT ROAD UNIT 301
OSPREY FL 34229
Residential / Condominium
3 Bed · 3 Bath · 2,680 SqFt · $233/SqFt
Days on Market: 2
County: Sarasota
Subdiv/Community Name: Meridian At The Oaks Preserve
Legal Subdivision Name: MERIDIAN AT THE OAKS PRESERVE
Year built: 2006
Garage: No
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, ... Read more....»
393 N POINT ROAD UNIT 301
OSPREY FL 34229
Residential / Condominium
3 Bed · 3 Bath · 2,594 SqFt · $241/SqFt
Days on Market: 9
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: MERIDIAN AT THE OAKS PRESERVE
Year built: 2001
Garage: Yes 2 vehicles
This end unit in The Meridian has been thoughtfully updated and carefully maintained. Offering 3 bedrooms and 3 full baths, it also has a dedicated study/den with pocket doors. Light and bright, this 2,594 square foot residence is spacious and offers room for comfortable and elegant living. The large master suite has a large bathroom with a walk-in shower, dual vanities and sinks and tons of cabinetry. The southern facing screened balcony, with electric Kelvin hurricane shutters, affords a lovely view of the Preserve. This unit has 2 parking spaces. Don’t pass up on the opportunity ... Read more....»
1140 BEACHCOMBER COURT UNIT 11
OSPREY FL 34229
Residential / Condominium
3 Bed · 2 Bath · 1 Half Bath · 2,040 SqFt · $294/SqFt
Days on Market: 10
County: Sarasota
Subdiv/Community Name: Blackburn Point Marina Village
Legal Subdivision Name: BLACKBURN POINT MARINA VILLAGE
Year built: 2005
Garage: Yes 1 vehicles
Community Pool: Yes
One or more photo(s) has been virtually staged. Welcome to Blackburn Point Marina Village, where coastal elegance meets maintenance-free living near Sarasota's desired waterfront. Enjoy the boating and waterfront lifestyle you've dreamed of without the million-dollar price tag. This beautifully upgraded townhome features a bright open floor plan with luxury vinyl flooring (2025), plantation shutters and 9-foot ceilings. The gourmet kitchen showcases granite countertops, Craft Maid cabinetry, a KitchenAid gas range, LG refrigerator (2023) and a wine refrigerator, ideal for entertaining. Highlights include a new roof (2025), enclosed sunroom, water filtration/softener system (2024), tankless water heater, motorized hurricane shutters, epoxy ... Read more....»
409 N POINT ROAD UNIT 502
OSPREY FL 34229
Residential / Condominium
3 Bed · 3 Bath · 2,055 SqFt · $291/SqFt
Days on Market: 520
County: Sarasota
Subdiv/Community Name: Meridian At The Oaks Preserve
Legal Subdivision Name: MERIDIAN AT THE OAKS PRESERVE
Year built: 2004
Garage: No
**GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The coveted lifestyle of The Oaks Country Club with the convenience and amenities of maintenance-free condominium living come together at this Gorgeous Meridian 5th floor residence. Upon exiting the elevator into the private foyer, step inside and enjoy the breathtaking panoramic preserve, bay and Gulf of Mexico views! The dramatic step ceiling defines the foyer space while leading into the expansive dining room, living room and open kitchen featuring Granite countertops and Stainless Steel appliances. Both the primary bedroom suite and living room open to the balcony ... Read more....»
242 HIDDEN BAY DRIVE UNIT 603
OSPREY FL 34229
Residential / Condominium
2 Bed · 2 Bath · 1,932 SqFt · $285/SqFt
Days on Market: 48
Cumulative Days on Market: 310
County: Sarasota
Complex/CommunityName: HIDDEN BAY
Subdiv/Community Name: Baypointe Vista
Legal Subdivision Name: BAYPOINTE VISTA 1
Year built: 1999
Garage: Yes 2 vehicles
Waterfront: Yes
Stunning, unobstructed views of the Intracoastal Waterway, Little Sarasota Bay, and the Gulf await from this beautiful Penthouse residence in Baypoint Vista, Osprey. Located within Hidden Bay, a gated and amenity rich community, this exceptional condo features 2 Bedrooms, 2 Bathrooms plus a versatile Den, an open floor plan, high ceilings, recessed lighting, a spacious kitchen, morning room, IMPACT WINDOWS AND SLIDERS, and a 2 Car Garage. The oversized primary suite is a private retreat with breath taking water views, complete with two walk-in closets, a linen closet, and a spa-like bathroom featuring a jetted soaking tub, walk-in shower, double ... Read more....»
786 SARABAY ROAD UNIT 19
OSPREY FL 34229
Residential / Villa
2 Bed · 2 Bath · 1,555 SqFt · $334/SqFt
Days on Market: 49
County: Sarasota
Subdiv/Community Name: Heron Bay Club
Legal Subdivision Name: HERON BAY CLUB SEC I
Year built: 1981
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
Boat Slips included, Insurance included, Ground maintenance included!!Secluded waterfront community on Little Sarasota Bay with access to the Intracoastal Waterway and the Gulf. Heron Bay Club has boat slips available! This small community on Little Sarasota Bay offers striking sunsets. Across from the northern section of Casey Key, the 10-acre property features 26 villas. This complex is intimate, quiet and peaceful. Part of the reason for the relaxing atmosphere is that Heron Bay Club lies off the beaten track. All villas have a courtyard entry, which creates a big, sheltered outdoor living area. This home has unmatched waterfront views from ... Read more....»
120 VILLA DRIVE UNIT 120
OSPREY FL 34229
Residential / Villa
2 Bed · 2 Bath · 1,404 SqFt · $367/SqFt
Days on Market: 321
County: Sarasota
Subdiv/Community Name: Sorrento Villas
Legal Subdivision Name: SORRENTO VILLAS 1
Year built: 1978
Garage: Yes 1 vehicles
Community Pool: Yes
Waterfront: Yes
Waterfront with your own private dock with 10,000lb elevator lift. This home is being offered fully furnished from the inside out to the lanai and boat dock. The kitchen features raised wood cabinets and a large 10ft long breakfast bar. The kitchen has views of the canal and opens up to the dining room and living room. As you walk into the nicely appointed open floor plan, you immediately feel relaxed while enjoying the water views and fish jumping. There is nothing to do but move in and enjoy your new home. Taking the boat out is a breeze. Just ... Read more....»
7303 JESSIE HARBOR DRIVE UNIT 7303
OSPREY FL 34229
Residential / Condominium
3 Bed · 2 Bath · 1,883 SqFt · $252/SqFt
Days on Market: 182
County: Sarasota
Subdiv/Community Name: Heron House
Legal Subdivision Name: HERON HOUSE
Year built: 1985
Garage: No
PENTHOUSE CONDO IN WATERFRONT COMMUNITY! Experience luxury coastal living in this spacious 3-bedroom, 2-bath penthouse condo, perfectly situated on a tranquil canal with dockage and direct, bridge-free access to the Intracoastal Waterway and the Gulf. This impressive 3rd-floor residence features an open floor plan with expansive rooms, plantation shutters, and three private balconies—ideal for soaking up the Florida sunshine and enjoying great views. The gourmet kitchen is a chef’s dream, offering granite countertops, wood cabinetry, stainless steel appliances, and a cozy eat-in area for casual dining. The expansive master suite boasts a private balcony, two walk-in closets, double vanities, a soaking tub, ... Read more....»
764 SARABAY ROAD UNIT 8
OSPREY FL 34229
Residential / Villa
2 Bed · 2 Bath · 1,392 SqFt · $323/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: Heron Bay Club
Legal Subdivision Name: HERON BAY CLUB SEC I
Year built: 1981
Garage: No
Waterfront: Yes
One or more photo(s) has been virtually staged. Live the Florida dream on the water! Wake up to shimmering bay views, spend your days boating and fishing, and end every evening with breathtaking sunsets over Little Sarasota Bay, all from this rarely available, maintenance-free waterfront villa. In the exclusive Heron Bay Club, an intimate bayfront enclave of just 25 villas set across 10 beautifully manicured acres, this home offers the ultimate Florida lifestyle. Enjoy resort-style amenities including a heated waterfront pool, tennis courts, kayak launch, fishing pier, and community docks with water and electric. Best of all, there are 10 ... Read more....»
1811 HIGHLAND ROAD
OSPREY FL 34229
Residential / Townhouse
2 Bed · 2 Bath · 1,725 SqFt · $248/SqFt
Days on Market: 124
County: Sarasota
Subdiv/Community Name: Not Applicable
Legal Subdivision Name: TOWNS-END SHORES
Year built: 1997
Garage: Yes 2 vehicles
Community Pool: Yes
PRIVATE NEIGHBORHOOD - Fully Furnished 2 Bedroom Townhouse in the Casey Key area, QUAINT, SPACIOUS 2-CAR Tandem GARAGE + Carport, modern, high ceilings, kitchen upgrades, screened balcony, 2 beds + den; 2 baths; living area and kitchen open plan; community pool Conveniently located between Sarasota, Siesta Key, Venice, and the Gulf Beaches. Walking distance to Casey Key Mainland (Chef Rolfs), private community Shoreland Park & Oscar Scherer State Park. Minutes away from COSTCO, Publix, Target, Richard's, YMCA Potter Park, waterfront dining (Casey Key Fish House & Tiki bar - waterfront , Spanish Point restaurant & Tiki Bar. The townhouse is close ... Read more....»
1823 HIGHLAND ROAD
OSPREY FL 34229
Residential / Townhouse
2 Bed · 2 Bath · 1,725 SqFt · $231/SqFt
County: Sarasota
Subdiv/Community Name: Osprey Park
Legal Subdivision Name: TOWNS-END SHORES
Year built: 1998
Garage: Yes 1 vehicles
Community Pool: Yes
This beautiful 2-bedroom, 2-bathroom townhouse offers the perfect blend of comfort, convenience, and Florida lifestyle. The home features a one-car garage plus an additional carport, providing two covered parking spaces. The garage has extended depth, offering extra room for storage of your favorite items such as kayaks, golf carts, and more. The open floor plan creates a bright and inviting living space, with the kitchen overlooking the living room and extending to a private balcony through large sliding glass doors. On the first floor, just off the spacious bonus room, step outside to a cozy uncovered lanai, an ideal spot for ... Read more....»
291 HIDDEN BAY DRIVE UNIT 102
OSPREY FL 34229
Residential / Condominium
2 Bed · 2 Bath · 1,479 SqFt · $270/SqFt
Days on Market: 26
County: Sarasota
Subdiv/Community Name: Lake Vista
Legal Subdivision Name: HIDDEN BAY / LAKE VISTA
Year built: 2000
Garage: Yes 1 vehicles
In the lush and serene grounds of this private and peaceful community is a best-kept secret with a name that says it all. Within Hidden Bay, this condominium gem resides in a spot on the community lake with a stunning view and soothing sound of waterfalls from your own enclosed lanai. Fully furnished with mostly all new furniture in the owners’ suite, including a new king-size mattress, living room, guest bedroom and the office/den, this turnkey treasure is move-in ready! Loaded with many new upgrades which include new kitchen appliances such as refrigerator, microwave and dishwasher (2025), new laminate flooring ... Read more....»
2251 JESSIE HARBOR DRIVE UNIT 2101
OSPREY FL 34229
Residential / Villa
2 Bed · 2 Bath · 1,400 SqFt · $249/SqFt
Days on Market: 453
County: Sarasota
Complex/CommunityName: BLACKBURN HARBOR
Subdiv/Community Name: Blackburn Harbor Waterfront Villas
Legal Subdivision Name: BLACKBURN HARBOR WATERFRONT VILLAS
Year built: 2005
Garage: Yes 1 vehicles
Waterfront: Yes
**1ST FLOOR END UNIT CONDO with WATER VIEW and PRIVATE 1-CAR GARAGE, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO (No Bridges)** Featuring 2 BEDS and 2 FULL BATHS, this LIGHT AND BRIGHT, 1ST FLOOR END UNIT dwelling features an Impressive Kitchen with Granite counters, Stainless Steel appliances and solid wood cabinets while the Spacious Owner’s Suite boasts multiple walk-in closets, dual vanities, soaking tub and custom tiled shower. Tile Flooring Throughout. Enjoy the serene and natural surroundings from your sprawling and screened lanai which is accessible from multiple rooms ... Read more....»
4284 EXPEDITION WAY UNIT NA
OSPREY FL 34229
Residential / Condominium
3 Bed · 2 Bath · 1,430 SqFt · $238/SqFt
Days on Market: 18
County: Sarasota
Subdiv/Community Name: Not Applicable
Legal Subdivision Name: BAY STREET VILLAGE
Year built: 2017
Garage: Yes 1 vehicles
Community Pool: Yes
Welcome to Bay Street Village, a gated, maintenance-free community in Osprey between Sarasota and Venice. The tile roofs and paver driveway provide Florida charm. This move-in-ready 3-bed, 2-bath condo features an open layout, IMPACT glass, and a private screened balcony with a pond view. The kitchen offers a large granite counter with seating and a newer refrigerator. The primary suite includes a walk-in closet and an en-suite bath with dual sinks and a step-in shower. A split floorplan adds privacy, and the attached one-car garage provides extra storage. Community amenities include a heated pool, fitness center, and clubhouse. Bay Street Park ... Read more....»
4304 EXPEDITION WAY WAY UNIT 105
OSPREY FL 34229
Residential / Condominium
3 Bed · 2 Bath · 1,528 SqFt · $222/SqFt
Days on Market: 7
County: Sarasota
Subdiv/Community Name: Bay Street Village & Towncenter Land Condo
Legal Subdivision Name: BAY STREET VILLAGE
Year built: 2018
Garage: Yes 1 vehicles
Spectacular water views from most windows in this immaculate, lightly used 3BR/2BA condo, built in 2018 and located in the gated community of Bay Street Villages. The popular Ibis floor plan offers an open-concept kitchen, dining, and great room with designer finishes, including white 42” cabinetry, light granite countertops, and stainless-steel appliances. Enjoy peaceful pond views with birds and wildlife from the screened lanai. Quality construction and peace of mind are provided by hurricane-impact windows and doors, concrete block construction, tile roof, and a paver driveway. The primary suite features plantation shutters, a custom ceiling fan with light, custom closet system, linen ... Read more....»
1801 HIGHLAND ROAD
OSPREY FL 34229
Residential / Townhouse
2 Bed · 2 Bath · 1,165 SqFt · $279/SqFt
Days on Market: 171
Cumulative Days on Market: 236
County: Sarasota
Subdiv/Community Name: Towns-End Shores
Legal Subdivision Name: TOWNS-END SHORES
Year built: 1999
Garage: Yes 2 vehicles
Community Pool: Yes
One or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhome in the desirable Town-End Shores community of Osprey! This beautifully maintained home features an open-concept first floor with a spacious living room, dining area, and a Florida room with sliding glass doors for added natural light. The gorgeous kitchen boasts granite countertops, perfect for cooking and entertaining. Elegant tray ceilings, crown molding, and 9-foot ceilings enhance the first floor living space. The flooring is a beautiful wood look tile and LVP throughout the home. Upstairs, you’ll find both bedrooms, including the primary suite with a ... Read more....»
51 MACEWEN DRIVE UNIT 11
OSPREY FL 34229
Residential / Condominium
1 Bed · 1 Bath · 623 SqFt · $441/SqFt
Days on Market: 46
County: Sarasota
Complex/CommunityName: THE OAKS CLUB
Subdiv/Community Name: The Oaks
Legal Subdivision Name: WINDSOR LODGE AT THE OAKS
Year built: 1990
Garage: No
Waterfront: Yes
Rarely available Windsor Lodge efficiency condominium located within The Oaks Club. This second-floor, maintenance-free, lakeside unit features a covered balcony with views of the lake, pool, and golf course. Elevator access to the second floor. Short-term rentals permitted. Enjoy the country club lifestyle at The Oaks Club, a private, member-owned club in Osprey, Florida. Mandatory membership required with purchase. Amenities include two championship 18-hole golf courses, twelve tennis courts, four pickleball courts, a state-of-the-art Fitness/WellFit Center, croquet courts, clubhouse with three restaurants, banquet facilities, and an active social calendar.
232 WOODLAND DRIVE UNIT 232
OSPREY FL 34229
Residential / Condominium
2 Bed · 2 Bath · 1,325 SqFt · $200/SqFt
Days on Market: 115
County: Sarasota
Subdiv/Community Name: Pine Run
Legal Subdivision Name: PINE RUN III
Year built: 1980
Garage: No
This condo has the 3 L's! Location Location Location! Located in the central area of Osprey making it an easy drive to area beaches, downtown Venice or Sarasota. Located about a half mile to the Inter Coastal, making for a great walking area on Casey Key. Located close to the well known Casey Key Fish House and Tiki Bar. Shopping and restaurants are all nearby! The location of this condo within the Pine Run community is also good with an abundance of trees and landscaping creating a private setting from your lanai ... Read more....»
244 WOODLAND DRIVE UNIT 244
OSPREY FL 34229
Residential / Condominium
2 Bed · 2 Bath · 1,325 SqFt · $151/SqFt
Days on Market: 142
County: Sarasota
Subdiv/Community Name: Pine Run
Legal Subdivision Name: PINE RUN III
Year built: 1980
Garage: No
Tranquil Coastal Living in Pine Run 244 Woodland Dr, Osprey, FL 34229 Tucked beneath a canopy of mature oaks and palms, this beautifully updated 2-bedroom, 2-bath condo captures the easy, natural rhythm of coastal Florida living. Nestled within the sought-after Pine Run community, it offers both peace and connection just minutes from the beaches of Casey Key, charming Venice, and downtown Sarasota. Step inside to discover light-filled spaces, a warm neutral palette, and a welcoming open layout. The kitchen stands out with stainless-steel appliances, a stylish glass backsplash, and playful custom cabinetry that adds personality and character. A cozy breakfast nook sits beside ... Read more....»
354 PINE RUN DRIVE
OSPREY FL 34229
Residential / Condominium
2 Bed · 2 Bath · 1,224 SqFt · $163/SqFt
Days on Market: 12
County: Sarasota
Subdiv/Community Name: Pine Run
Legal Subdivision Name: PINE RUN I
Year built: 1973
Garage: No
Live among the trees! This condo is nestled in one of the most desirable areas of Pine Run. Outside your living room/kitchen sliders, all you see are a greenbelt and trees, creating a sense of ultimate privacy. The property has been updated, and some of the many special features include: soaring ceilings, outdoor spaces off of the living room, kitchen & bedrooms, stainless appliances, wood flooring, blackout shades for all sliders, and so much more. Whether you are looking to live here full-time or seasonally, Pine Run is a community of friendly, active, pet-loving residents! Regular activities include tennis, pickle ... Read more....»
211 WOODLAND DRIVE UNIT 211
OSPREY FL 34229
Residential / Condominium
2 Bed · 2 Bath · 1,223 SqFt · $164/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: Pine Run
Legal Subdivision Name: PINE RUN III
Year built: 1980
Garage: No
Community Pool: Yes
Tucked away in the charming community of Pine Run, this uniquely designed two-story condo offers the perfect blend of privacy, comfort, and Florida lifestyle living in the heart of Osprey. This spacious 2-bedroom, 2-bath residence features a layout offering the primary suite on the first floor—ideal for ease of living and added privacy. The main level offers an inviting living and dining area filled with natural light, creating a warm and welcoming space for both relaxing and entertaining. The primary bedroom retreat provides generous space, ample closet storage, and a well-appointed en-suite bath. Upstairs, you’ll find a loft that is ... Read more....»
200 WOODLAND DRIVE
OSPREY FL 34229
Residential / Condominium
1 Bed · 1 Bath · 1 Half Bath · 865 SqFt · $202/SqFt
Days on Market: 37
County: Sarasota
Subdiv/Community Name: Pine Run
Legal Subdivision Name: PINE RUN III
Year built: 1980
Garage: No
One or more photo(s) has been virtually staged. Welcome to Pine Run in Osprey! Half-way between Sarasota and Venice, convenient to both with ample shopping and dining close by. Your 1 bedroom one and a half bath oasis is nestled on 20+ acres of lush native Florida landscape. This popular ground floor unit features large glass sliders and your own private courtyard in the front of the unit where you can enjoy your morning coffee and a screen enclosed covered rear porch where you can enjoy your evening with a beautiful sunset glow. New interior paint and baseboards surround ... Read more....»
The information relating to real estate for sale on this website comes in part from the My Florida Regional MLS DBA Stellar MLS. This information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS.
