Displaying: For Sale
Location: Osprey
Property Type(s): Condos
Living Area Square Feet: 1000 to 1499
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Osprey - 8 properties found
4271 EXPEDITION WAY #103, OSPREY, FL 34229
$290,00025 Days on yellowkey MLS ID: A4689541
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1135 Built: 2017 Tax: $3,507 (2025)Community: Bay Street VillageCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,507
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: One or more photo(s) has been virtually staged. Live where everyday life feels simple, connected, and close to everything you love. Located in the gated community of Bay Street Village in Osprey, this beautifully maintained second-floor condo offers the perfect blend of comfort, convenience, and a relaxed Florida lifestyle. Just minutes from Nokomis Beach, Siesta Key, the Legacy Trail, Oscar Scherer State Park, and an abundance of shopping and dining options, everything you need is right at your fingertips. This 2-bedroom, 2-bathroom condo welcomes you with a private entry and interior stairway leading to a bright and open main living space. Positioned on the second floor, the home enjoys added privacy along with elevated views and an abundance of natural light. The layout lives effortlessly, with high ceilings and neutral finishes creating an inviting and airy feel throughout. An attached garage with direct interior access adds everyday ease and practicality. The kitchen is both functional and stylish, featuring granite countertops, stainless steel appliances, a large island with seating, and a walk-in pantry. It opens seamlessly to the dining and living areas, making it easy to host, relax, or simply enjoy day-to-day living without feeling closed off. The spacious primary suite offers a comfortable retreat with a large walk-in closet and an en-suite bathroom complete with dual sinks and a walk-in shower. A second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Enjoy your morning coffee or unwind in the evening on the screened lanai, where you can take in the Florida breeze and peaceful surroundings from your elevated position. Whether you're heading out to the beach, meeting friends for dinner, or enjoying the nearby parks and trails, this location makes it all feel effortless. Bay Street Village enhances the lifestyle even further with resort-style amenities including a community pool, fitness center, scenic ponds, and beautifully landscaped grounds, all within a gated and well-maintained setting. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
232 WOODLAND DR #232, OSPREY, FL 34229
$259,900173 Days on yellowkey MLS ID: A4671600
0 Days Off yellowkey (back on 4/25/2026)
REDUCED by $5,000 (1.9%) on 04/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1980 Tax: $2,202 (2025)Community: Pine Run IiiCondo
Taxes:$2,202
Remarks: Under contract-accepting backup offers. 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 off the livingroom. You will feel like you are living in a tree house! This condo has had extensive work done in the last 6 years including ELECTRIC ON-DEMAND TANKLESS HOT WATER HEATER, NEW CUSTOM KITCHEN WITH DOVE TAIL DRAWER CHERRY CABINETS, FLOORING, PAINT, LIGHT FIXTURES, NEW BATHROOMS AND PLUMBING. Unique frosted glass sliding doors in the dinette area open to washer dryer combo plus a pantry area! Crown molding in the living and dining area give an elegant feel to the rooms, The roof, maintained by the HOA was replaced about 3 years ago. Pine run is an active, vibrant community with small clubhouse with fitness room, pickle ball, tennis and other activities just waiting for you. Come take a look! If you are comparing other condo's, this one has much to like!
Listing is courtesy of: PAT WILLIAMS REALTY, LLC (941-289-6231)
Listing Agent: Pat Williams (941-289-6231)
244 WOODLAND DR #244, OSPREY, FL 34229
$200,000201 Days on yellowkey MLS ID: A4667419
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1980 Tax: $2,685 (2025)Community: Pine Run IiiCondo
Taxes:$2,685
Elementary School: None
High School: None
Middle School: None
Remarks: One or more photo(s) has been virtually staged. Turnkey-Furnished & Best Value in Pine Run Now Offered at $200,000 (Recently Reduced $25,000). Move right in and start enjoying the Florida lifestyle with this beautifully updated 2-bedroom, 2-bath condo offering 1,325 square feet of bright, open living. Featuring vaulted ceilings and an airy layout, this residence feels spacious and inviting from the moment you walk in. The kitchen showcases stainless steel appliances, a sleek glass backsplash, and a sunlit breakfast nook perfect for everyday living or entertaining. The primary suite offers direct access to the screened lanai, creating a seamless indoor-outdoor flow with peaceful views of lush, private greenery. Being sold turnkey-furnished, this is a true move-in-ready opportunity just bring your suitcase. Located in the highly sought-after Pine Run community, residents enjoy resort-style amenities including two heated pools, tennis and pickleball courts, a fitness center, clubhouse, and over 20 acres of scenic walking trails. All just minutes from Nokomis Beach, Casey Key, dining, and shopping. Low-maintenance, turnkey living at an unbeatable price, ideal for full-time, seasonal, or investment use.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Derek Edwards (941-929-3183)
291 HIDDEN BAY DR #102, OSPREY, FL 34229
$399,00089 Days on yellowkey MLS ID: A4681398
5 Days Off yellowkey (back on 4/20/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1479 Built: 2000 Tax: $4,266 (2025)Community: Hidden Bay / Lake VistaCondo
Taxes:$4,266
Middle School: Sarasota Middle
Remarks: 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 in both bedrooms (2025), a new water heater (2024), new faucets and toilets (2025), new air conditioner (2020), all new screens (2025), all new slider wheels (2025) and interior painted (2025). The home offers two bedrooms, two baths and an office/den, a one- car detached garage and an etched glass front door. The flooring consists of new laminate in both bedrooms, laminate in the office/den and ceramic tile throughout the rest of the home. Beautiful lake views can be seen from the living room, kitchen and owner’s suite. The owner’s suite bath has dual vanities, a soaking tub and a walk-in shower while the guest bath has a soaking tub. This unique waterfront community exudes an awesome Florida lifestyle that boasts many amenities with a newly renovated heated pool and spa, a clubhouse with a full kitchen, a tiki bar, game rooms, a library, a fitness center, a large sundeck, grilling stations, two lit pickleball courts, tennis, a kayak launch, a dog park, a car wash area and a 500-yard elevated boardwalk that winds through mangroves and palms offering scenic sunset watching. And coming soon is a 150-foot fishing pier all for your enjoyment. HOA fees include exterior maintenance, water, sewer, trash and basic cable. Centrally located between Sarasota and Venice, Hidden Bay is on Little Sarasota Bay in Osprey, an ideal location just minutes from the award-winning beaches of Siesta Key and Venice Beach, Sarasota with its many cultural venues, golfing and a variety of casual and fine dining restaurants. Make this special home your own piece of paradise!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Pat Mcmillan (941-544-4538)
4284 EXPEDITION WAY #NA, OSPREY, FL 34229
$339,90081 Days on yellowkey MLS ID: A4681835
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1430 Built: 2017 Tax: $2,934 (2025)Community: Bay Street VillageCondo
Taxes:$2,934
Remarks: 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 is directly across the street and is walkable—includes a dog park for your furry friend. Water is included in the monthly fee. Conveniently located near Nokomis Beach, Oscar Scherer State Park, The Legacy Trail, Publix, restaurants, shopping, and both US-41 and I-75, this condo offers easy, low-maintenance Florida living in a central coastal location in a very nice community.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Grace Bonaccorso (941-580-1362)
4173 FRONTIER LN #4173, OSPREY, FL 34229
$289,00025 Days on yellowkey MLS ID: A4689582
2 Days Off yellowkey (back on 4/15/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1135 Built: 2019 Tax: $2,478 (2025)Community: Bay Street VillageCondo
Taxes:$2,478
Remarks: Under contract-accepting backup offers. INCREDIBLE CHARM!....INCREDIBLE LOCATION!.....You will be ENAMORED by this Highly Sought After (2) Bedroom (2) Bath Heron Floor Plan with PRIVATE GARAGE in the PET FRIENDLY Gated Community, Bay Street Village. This Meticulously Maintained One Owner corner unit residence features BRIGHT SPACIOUS INTERIORS; Hurricane Impact Windows and a Generous Screened Lanai---perfect for enjoying Morning Coffee while listening to your Favorite Podcast or just relaxing with Evening Cocktails.....Meal Prep is Easy with OVER-SIZED KITCHEN ISLAND; Stainless Steel Appliances and Pantry for Extra Storage....Bay Street is Conveniently Located to EVERYTHING: Shopping; Dining; Recreation; the New Sarasota Memorial Hospital; Legacy Bike Trail and just minutes to MULTIPLE BEACHES, including TOP RATED SIESTA KEY!.....Ideal as Year-Round, Vacation or Investment Property.
Listing Agent: Mike Martino (773-619-8593)
135 WOODLAND PL, OSPREY, FL 34229
$269,00036 Days on yellowkey MLS ID: A4687664
1 Days Off yellowkey (back on 4/13/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1316 Built: 1979 Tax: $2,660 (2025)Community: Pine Run IiCondo
Taxes:$2,660
Remarks: Ideally located in the heart of Osprey, this private corner, first floor condo offers effortless Florida living just minutes from pristine Gulf beaches and less than half a mile from the Intracoastal Waterway. The sought after community at the entrance to Casey Key was designed to live in harmony with nature by Frank Folsum Smith of the Sarasota School of Architecture. This unit features a garden view with four patios that includes a rear lanai enclosed with sliding vinyl windows. A unique inner atrium with aquarium style glass windows adds architectural interest and abundant natural light while maintaining privacy. The unit features easy to maintain custom tile floors on the diagonal throughout with wood floor inspired ceramic tiles in the bedrooms. Since 2023, unit updates include all new kitchen appliances, new faucets, new PEX water lines, a new water heater as well as new paint inside and out. The unit also includes a deeded carport parking space and two storage closets. Onsite resort style amenities include two heated pools (one overlooking a lagoon), two cedar saunas, a fitness room, Florida style clubhouse, walking trails, BBQ gas grill, outdoor gas fireplace, kayak storage, pickleball and tennis courts. Within a mile is the Pine View School (the only standalone public gifted school in the state), Oscar Scherer State Park, 2 kayak launches, a public boat ramp, Casey Key Fish House, Walmart and a Post Office. Easily walk to Publix, Ace Hardware, CVS, shops and restaurants or bike to the Legacy Trail and Nokomis Beach. Exceptional privacy, easy access, and a premier location make this residence an outstanding opportunity. Priced to sell!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Kim Azar-Calka (239-216-6205)
4226 FRONTIER LN #103, OSPREY, FL 34229
$319,00028 Days on yellowkey MLS ID: A4687965
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1135 Built: 2018Monthly Fee: $475 Tax: $3,542 (2025)Community: Bay Street VillageCondo
Taxes:$3,542
Remarks: Coastal convenience meets effortless living, just minutes from Siesta Key, America’s #1 beach. Welcome to 4226 Frontier Lane, a beautifully maintained 2-bedroom, 2-bath walk-up condo in the gated community of Bay Street Village, offering exceptional value and an easy Florida lifestyle. Built for peace of mind with hurricane impact windows concrete-block construction. A private ground-level garage provides added convenience and storage. Upstairs, the bright, open-concept floor plan is filled with natural light, creating an inviting space for both everyday living and entertaining. The well-appointed kitchen features 42" cabinetry, granite countertops, stainless steel appliances, and a spacious walk-in pantry, seamlessly flowing into the dining and living areas. Step out onto your large, screened-in lanai to enjoy peaceful mornings or evening cocktails. The generously sized primary suite offers a walk-in closet and an ensuite bath with dual vanities and a tiled walk-in shower. A second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Ideally located in Osprey, between Sarasota and Venice, you’ll enjoy a quiet, tucked-away setting with shopping, dining, and daily conveniences just minutes away. Bay Street Village residents enjoy resort-style amenities including a heated pool, fitness center, and clubhouse. With reasonable HOA fees covering exterior maintenance, roof, water, sewer, and gated access (and no flood insurance required) this is truly low-maintenance ownership at its best. Perfect as a full-time residence, seasonal escape, or investment opportunity this is Florida living, simplified.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Kate Kwiecinski (412-477-9720)
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