Location: Osprey
Keyword(s): Laurel Nokomis Middle
Keyword(s) Middle School: Laurel Nokomis Middle
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4219 FRONTIER WAY #105, OSPREY, FL 34229
$2,25066 Days on yellowkey MLS ID: N6144275
REDUCED by $50 (2.2%) on 06/29/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1244 Built: 2017Community: Bay Street VillageSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year:
Middle School: Laurel Nokomis Middle
Remarks: Welcome to this immaculate 2-bedroom, 2-bathroom condo with a private 1-car garage, offering beautiful pond views from every window and a peaceful, resort-style setting. Ideally located just minutes from some of Florida’s most beautiful Gulf Coast beaches: 10 minutes to Nokomis Beach and Casey Key 15 minutes to the world-famous Siesta Key Beach Outdoor enthusiasts will love the easy access to the Legacy Trail, perfect for biking, walking, and jogging. This maintenance-free, gated community offers exceptional amenities, including: Resort-style swimming pool with cabana Fitness center Clubhouse Built for quality and peace of mind, the condo features: Solid concrete block construction Impact-resistant windows Tile roof Paver driveway Enjoy a convenient location between Sarasota and Venice, just minutes from shopping, restaurants, parks, medical facilities, and the highly acclaimed Pine View School. Water, sewer, and trash service are included in the rent. Rent: $2,250 per month
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Tim Weller (941-221-0155)
534 OAK BAY DR, OSPREY, FL 34229
$3,8007 Days on yellowkey MLS ID: A4699469
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2077 Built: 1996Community: Bay Oaks Ests Unit 1Spa: NoSingle Family
Remarks: AVAILABLE AUGUST 25, 2026 AS UNFURNISHED RENTAL. Very nice light and bright 4 bedroom pool home with private secluded lot in the quaint community of Oak Bay Estates in Osprey. Great access to Sarasota and Venice without having to get on I-75. New interior paint and new ceiling fans throughout. Enjoy this great home and the private pool in your spare time as the pool care and lawn and landscaping are done for you and included in the rent. This home is located in a very nice neighborhood with easy access to many restaurants, shopping and the Florida lifestyle including the Legacy Trail for biking, walking or jogging. Only 10 minutes to two of the finest beaches on the Gulf Coast at Siesta key and Nokomis beach. First and last months rent and security deposit due upfront. pets are possible and are considered on a case by case basis.
Listing is courtesy of: REALTY BY DESIGN LLC (941-779-4509)
Listing Agent: Brian Odonnell (941-779-4509)
152 NAVIGATION CIR #107, OSPREY, FL 34229
$4,5001707 Days on yellowkey MLS ID: A4517611
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1528 Built: 2016 Tax: $3,006 (2021)Community: Bay Street VillageCondo
Taxes:$3,006
Tax Year: 2021
Remarks: BACIK ON THE MARKET HIGH SEASON NOW AVAILABLE!! Seasonal and short term rental Get out of the cold and into the sunshine in this newer 3/2 condo in the gated community of Bay Street Village in Osprey. This condo is an end unit with an open floor plan for ease of entertaining and family time. The extra windows flood the unit with natural sun light. The kitchen is a natural gathering point with solid wooden cabinetry, topped with slab granite counters and breakfast bar and complemented with stainless steel appliances. The master suite is spacious with a king bed, walk in closet and en suite bathroom with walk in shower and double vanity. There are two additional bedrooms-one with a queen size bed and one set up as a den with a pull out couch. The amenity package features a resort style heated pool, club room, fitness center and BBQ grills. Bay Street Park is right across the street and you'll find yourself close to the beach, downtown Sarasota or Venice, the Legacy Trail, shopping, dining and museums. RENTED FEB-MARCH 2027. This community is governed by a homeowners association. Approval may include an application, background screening, fees, and an approval process. Contact the agent for details. Call now for your next vacation in the Florida sunshine!
Listing is courtesy of: RENT SARASOTA (941-328-8999)
Listing Agent: Cody Smith (404-991-0209)
293 HIDDEN BAY DR #203, OSPREY, FL 34229
$5,0002894 Days on yellowkey MLS ID: A4410764
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1568 Built: 2000 Tax: $3,620 (2021)Community: Hidden BayCondo
Taxes:$3,620
Remarks: AVAILABLE 2027 SEASON. TURNKEY FURNISHED RENTAL! GATED, WATER VIEWS! WATERFRONT COMMUNITY IN OSPREY! 2 Bedroom 2 bath plus den. Den has French doors. Lots of light from this second-floor end unit condo. Front door has disappearing screen for fresh Air. TURNKEY FURNISHED. Completely renovated. NO CARPET. Porcelain tile thru out. Granite counters and high ceilings. Front loading washer & dryer inside unit. Nicely renovated with closet barn doors. Stainless appliances. Detached one car garage immediately in front of condo and plenty of parking. PET OKAY with owner approval and nonrefundable pet fee. Resort style community pool, heated spa, fitness room, tennis courts, reading room, BBQ area with covered bar for guests, community clubhouse with kitchen. Short distance to shores of Little Sarasota Bay, Casey Key, Siesta Key. Fishing pier. Easy commute to shopping, restaurants and more. NO CATS. OWNER HAS ALLERGIES. CALL AGENT FOR MORE INFORMATION. Rentals under 6 months are subject to Sales and Tourist tax(13%). Note that rates are subject to change without notice and reservations are not guaranteed until initial reservation deposit is received.
Listing is courtesy of: WAGNER REALTY (941-756-7800)
Listing Agent: Alba Lange (941-704-3026)
852 MACEWEN DR, OSPREY, FL 34229
$7,000360 Days on yellowkey MLS ID: A4659277
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4519 Built: 1992Community: Oaks 2 Ph 2Spa: YesSingle Family
Remarks: **CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and Wetbar, 3-CAR GARAGE, etc. Premium features abound including Crown moldings, Marble and wood floors, Coffered ceiling, Custom built-ins, a well-equipped kitchen with Granite countertops, Stainless Steel Appliances including KitchenAid and Fisher & Paykel, and much more! An Expansive Primary Bedroom Suite features a Bonus Room, Walk-In Closet, dual vanities, soaking tub and custom-tiled shower. Enjoy OUTDOOR LIVING at its FINEST in an Expansive, Screened Lanai with PEBBLETEC Pool & Spa and Outdoor Kitchen in a serene setting. NEW HURRICANE IMPACT SLIDING DOORS and WINDOWS; ROOF (2015). THE OAKS is a distinguished country club community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World. 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. **ENJOY VIEWING THE 3D VIRTUAL TOUR**
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
293 TURQUOISE LN, OSPREY, FL 34229
$5,750917 Days on yellowkey MLS ID: A4594860
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2271 Built: 2001Community: OaksSpa: NoSingle Family
Remarks: **RARE RENTAL OPPORTUNITY (UNFURNISHED)** This STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the SECURE GATES of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank, Plantation Shutters, an Oversized, Owner’s Bedroom Suite with Multiple walk-in closets and sitting area and much more! Enjoy the expansive and private outdoor living area in a screened lanai with wet bar and southern exposure overlooking a Garden and Tranquil Preserve. Mostly NEW Hurricane Impact Windows/Door. 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.
51 MACEWEN DR #12, OSPREY, FL 34229
$2,250124 Days on yellowkey MLS ID: A4686127
REDUCED by $150 (6.3%) on 04/01/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 623 Built: 1990Community: OaksCondo
Remarks: For Lease at THE OAKS CLUB WINDSOR LODGE. Private sanctuary rarely available for rent at one of Sarasota's most exclusive private country clubs. This lovely sunny Second floor end unit is fully turnkey furnished and ready for MOVE IN. Completely updated one bedroom, resort suite style studio, condominium with sweeping Water Views of the Lakefront of the 18th fairway on the Eagle Course. A combined bedroom/living room, new kitchenette with quartz countertop, dining nook, office/dressing room, well designed bathroom with walk-in shower, office/dressing room, and stacked washer/dryer. Lobby elevator provides access to the second floor. Windsor Lodge Residents have their own private swimming pool and club house. Centrally located and 15 minutes to Siesta Key Beach. Note: Residents of Windsor Lodge do not have access to The Oak Club amenities. Available now for an seven plus month lease at $2250 month.
Listing is courtesy of: WAGNER REALTY (941-955-1500)
Listing Agent: Patrice Ivan (941-993-0823)
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