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....»
1811 HIGHLAND ROAD
OSPREY FL 34229
Residential / Townhouse
2 Bed · 2 Bath · 1,725 SqFt · $251/SqFt
Days on Market: 90
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....»
124 REVOLUTION WAY
OSPREY FL 34229
Residential / Condominium
2 Bed · 2 Bath · 1,574 SqFt · $253/SqFt
Days on Market: 7
County: Sarasota
Subdiv/Community Name: Bay Street Village & Towncenter Land Condo
Legal Subdivision Name: BAY STREET VILLAGE
Year built: 2016
Garage: Yes 2 vehicles
Community Pool: Yes
Waterfront: Yes
The only available home in the community with a 2 Car Garage! Welcome to Bay Street Village, a charming, beach-close, gated community in sought-after Osprey. This rarely available First-Floor residence features an oversized two-car garage with exceptional space for vehicles, bikes, kayaks, and all your Florida adventure gear. Ideally situated on a quiet cul-de-sac with peaceful pond views, this light-filled, move-in-ready home offers tranquil water vistas from both the interior and the screened lanai. The open-concept floor plan flows effortlessly, creating a comfortable and inviting living space. The owner’s suite enjoys serene pond views, while the guest bedroom is thoughtfully positioned on ... Read more....»
2251 JESSIE HARBOR DRIVE UNIT 2101
OSPREY FL 34229
Residential / Villa
2 Bed · 2 Bath · 1,400 SqFt · $282/SqFt
Days on Market: 355
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....»
401 N POINT ROAD UNIT 301
OSPREY FL 34229
Residential / Condominium
3 Bed · 3 Bath · 2,594 SqFt · $152/SqFt
Days on Market: 564
County: Sarasota
Subdiv/Community Name: Meridian At The Oaks Preserve
Legal Subdivision Name: MERIDIAN AT THE OAKS PRESERVE
Year built: 2003
Garage: No
One or more photo(s) has been virtually staged. Enter through the secure foyer and take the private elevator to the third floor where you will find this charming 3 bedroom, 3 bath residence. Situated at treetop level, overlooking the preserve and surrounding lush foliage, the interior is open and neutral, with lots of natural light. This unit is waiting for you to come and put your decorating touches on it and make it uniquely your own. Check out the virtually staged photos to help you imagine what you could do with this great floor plan. This condo offers space for ... Read more....»
1801 HIGHLAND ROAD
OSPREY FL 34229
Residential / Townhouse
2 Bed · 2 Bath · 1,165 SqFt · $283/SqFt
Days on Market: 134
Cumulative Days on Market: 199
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....»
116 NAVIGATION CIRCLE UNIT 106
OSPREY FL 34229
Residential / Condominium
3 Bed · 2 Bath · 1,430 SqFt · $227/SqFt
Days on Market: 89
Cumulative Days on Market: 421
County: Sarasota
Subdiv/Community Name: Bay Street Village & Towncenter Land Condo
Legal Subdivision Name: BAY STREET VILLAGE
Year built: 2016
Garage: Yes 1 vehicles
Community Pool: Yes
Location, Lifestyle, and Peace of Mind — All in One! Welcome home to this beautifully appointed 3-bedroom, 2-bath end-unit condo in one of the area's most desirable pet-friendly gated communities. Built with lasting quality in mind, this home offers solid block stucco construction paired with hurricane-impact windows and doors — giving you the comfort of security and the ease of low maintenance living. Step inside and be greeted by an inviting open-concept floor plan designed for modern living. Soaring ceilings, abundant natural light, and a thoughtful split-bedroom layout create the perfect blend of spaciousness and privacy. The heart of the home — ... Read more....»
100 NAVIGATION CIRCLE UNIT NA
OSPREY FL 34229
Residential / Condominium
2 Bed · 2 Bath · 1,135 SqFt · $269/SqFt
Days on Market: 23
County: Sarasota
Subdiv/Community Name: Bay Street Village & Towncenter Land Condo
Legal Subdivision Name: BAY STREET VILLAGES
Year built: 2018
Garage: Yes 1 vehicles
Community Pool: Yes
Welcome to Bay Street Village in Osprey, where maintenance-free Florida living awaits in this gorgeous gated community. This immaculate end-unit condo features 2 bedrooms, 2 bathrooms, and a 1-car garage. The garage is located beneath the unit and offers a private interior stairway leading to your second-floor residence. Enjoy an open-concept living and dining area perfect for entertaining that flows seamlessly into the beautiful kitchen, complete with a walk-in pantry, stainless steel appliances, and ample seating around a center island. The peaceful primary suite offers a walk-in closet and an ensuite bathroom with dual sinks, a makeup vanity, and a walk-in shower. Bay Street Village provides resort-style ... Read more....»
51 MACEWEN DRIVE UNIT 11
OSPREY FL 34229
Residential / Condominium
1 Bed · 1 Bath · 623 SqFt · $482/SqFt
Days on Market: 5
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: 76
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....»
362 PINE RUN DRIVE
OSPREY FL 34229
Residential / Condominium
2 Bed · 2 Bath · 1,224 SqFt · $192/SqFt
Days on Market: 27
County: Sarasota
Subdiv/Community Name: Pine Run
Legal Subdivision Name: PINE RUN I
Year built: 1973
Garage: No
One or more photo(s) has been virtually staged. Welcome to 362 Pine Run Drive, a move-in ready, modern retreat nestled in the heart of Osprey, FL. This stunning 2-bedroom, 2-bathroom home offers 1,224 square feet of thoughtfully designed living space, set on an expansive 20-acre property. Revel in the tranquility of garden views and the glow of sunsets in the distance off the rear facing deck. Looking for a little more privacy? Access a large, private outdoor area from the kitchen or off of the main hallway. Soaring ceilings and abundant natural light fill the living areas and each room ... Read more....»
244 WOODLAND DRIVE UNIT 244
OSPREY FL 34229
Residential / Condominium
2 Bed · 2 Bath · 1,325 SqFt · $162/SqFt
Days on Market: 102
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....»
238 WOODLAND DRIVE UNIT 238
OSPREY FL 34229
Residential / Condominium
1 Bed · 1 Bath · 1 Half Bath · 865 SqFt · $214/SqFt
Days on Market: 108
County: Sarasota
Subdiv/Community Name: Pine Run
Legal Subdivision Name: PINE RUN III
Year built: 1980
Garage: No
GREAT NEW PRICE to live like you're on vacation every day in this beautiful one bedroom, one and a half bath, FIRST FLOOR condo in the popular community of Pine Run! Step inside and you'll find a welcoming, well-designed, floor plan that is beautifully decorated throughout. The primary bedroom has a beautiful UPDATED ensuite bathroom with a new hurricane window, dual closets and a private sliding patio door to the back lanai that lets the natural light in. The half bath is also UPDATED and has granite countertops. The UPDATED kitchen has plenty of cabinets for storage, beautiful granite countertops, ... 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.
