Osprey Homes under $350,000

Osprey Homes under $350,000

Welcome to Osprey, Florida—a hidden gem nestled in the heart of Sarasota County. This charming community, located just south of the vibrant city of Sarasota and adjacent to Nokomis, offers a delightful blend of coastal living and suburban tranquility. Known for its stunning natural beauty, Osprey is bordered by the scenic waters of the Gulf of Mexico and the lush landscapes of the Oscar Scherer State Park, providing residents with endless opportunities for outdoor adventures.

Osprey is not just a paradise for nature lovers; it’s also a community that boasts a rich history and a vibrant local culture. The area is home to a variety of restaurants, shops, and art galleries, making it a perfect spot for those who enjoy both leisure and lifestyle. With its close-knit community feel and friendly atmosphere, Osprey is ideal for families, retirees, and everyone in between.

For those seeking affordable housing options, Osprey has a selection of charming homes priced under $350,000. These properties offer a fantastic opportunity for first-time buyers or anyone looking to invest in a slice of Florida paradise without breaking the bank. Whether you’re searching for a cozy single-family home or a low-maintenance condo, Osprey’s real estate market has something to suit every taste and budget.

Experience the best of Florida living in Osprey, where stunning landscapes, a welcoming community, and affordable homes await. Your dream home in this beautiful coastal town is just a visit away!

Newest Osprey Homes under $350,000

145 Edgewood Drive, Osprey
$175,000
2 Beds ⋅ 2 Baths ⋅ Arbors SubDv. ⋅ 34229 Zip Code
Discover comfortable Florida living in this charming 2-bedroom, 2-bath manufactured home ideally located in Osprey’s popular Arbors community. Positioned on a spacious corner lot, this inviting residence features a bright, open layout with the living room flowing naturally into the dining area and kitchen. A standout feature is the beautifully renovated enclosed front porch, complete with hurricane-impact windows—an ideal spot for morning coffee, relaxing, or enjoying the Florida sunshine year-round. The updated light and bright kitchen adds a fresh, clean feel, while a covered one-car carport and convenient storage shed provide practical storage and parking. Residents of The Arbors enjoy an active community lifestyle with a clubhouse, swimming pool, shuffleboard courts, outdoor fitness area, and a variety of social activities. Conveniently located between Sarasota and Venice, you’re close to shopping, dining, entertainment, performing arts, and the Gulf beaches. A great opportunity to enjoy an easygoing Florida lifestyle in a welcoming Osprey community!

145 Edgewood Drive, Osprey
717 Pine Run Dr. Unit 717, Osprey
$159,900
1 Beds ⋅ 1 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
Ready for your own slice of Florida paradise? This fully furnished, turnkey one-bedroom condo in Osprey’s Pine Run community is ready to welcome you home. Its second-floor setting offers a charming treehouse feel, surrounded by the community’s lush, natural landscape. Well cared for and thoughtfully updated, this condo features BRAND-NEW A/C (SEPTEMBER 2026), A NEW TANKLESS WATER HEATER (2025), AND A NEW HURRICANE-RATED SLIDING GLASS ENTRY DOOR (2022). Soaring ceilings and three sliding glass doors fill the open living and updated kitchen area with natural light, creating a bright, airy atmosphere. The screened balcony is an inviting spot for morning coffee or relaxing at the end of the day. A carport space directly below the condo provides convenient covered parking, along with an oversized storage closet. Whether you’re purchasing your first Florida home, downsizing, or looking for a winter retreat, this condo offers comfortable, easy living. Shopping and restaurants are within easy walking distance, with the local favorite Casey Key Fish House and Tiki Bar just down the street, along with the Intracoastal Waterway. Nearby Blackburn Point Park and its boat launch offer even more ways to enjoy the outdoors. Pine Runs’ amenities include pickleball and tennis courts, two pools, a community clubhouse, and a fitness area - all nestled within a lush, natural setting. Come take a look and picture yourself enjoying the Florida Lifestyle!

717 Pine Run Dr. Unit 717, Osprey
23 Siesta Circle W, Osprey
$165,000
2 Beds ⋅ 2 Baths ⋅ Arbors SubDv. ⋅ 34229 Zip Code
Welcome home to this charming fully furnished 2-bedroom, 2-bath mobile home, built in 2001 and located in the friendly and active Arbors Mobile Home Park in beautiful Osprey, Florida. Featuring an inviting open floor plan, this home offers comfortable living spaces filled with natural light from an abundance of windows. Luxury vinyl plank flooring flows throughout the living areas, creating a clean and cohesive look. The kitchen opens seamlessly to the living and dining areas, making entertaining and everyday living easy. The dining room features a built-in buffet with both lower and upper-glass-front cabinets, providing attractive display space and convenient storage. The primary suite includes a single vanity and walk-in shower, while cathedral ceilings add to the home's open and airy feel. An interior laundry area adds everyday convenience. Outside, a charming shed provides additional storage, and the newer carport, added in 2025, offers covered parking. The AC was replaced in 2024 for added peace of mind. Enjoy the Florida lifestyle in The Arbors, a welcoming 55+ community with a variety of amenities and an active social calendar offering plenty of opportunities to meet neighbors and stay involved. Enjoy the clubhouse, swimming pool, shuffleboard courts and fitness area. Ideally situated between Sarasota and Venice, you’ll have easy access to boutique stye shopping, multiple dining options, theaters, performing arts venues, and stunning Gulf beaches. Everything you love about the Florida lifestyle just minutes away. This is relaxed, low-maintenance living in a welcoming community. Come see why so many love calling The Arbors home!

23 Siesta Circle W, Osprey
109 Woodland Place, Osprey
$244,900
2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
TURNKEY Furnished 2 bed, 2 bath two story condo in the lifestyle rich community of Pine Run! Outdoor enthusiasts will love this 20 Acre mature landscaped neighborhood. Nearby, you will find nature parks, walking and biking trails, boat ramps, waterfront dining and minutes to beaches and downtown Venice! Within the community, you can enjoy TWO community pools, pickleball and tennis courts, clubhouse, fitness center and saunas in the community bathrooms. HOA includes Water, Sewer Trash and Pest control. Included with the unit is an assigned outdoor carport space and storage closet. Enjoy the natural lighting and privacy this unit greets you with as you walk through the door. The soaring ceilings bring in natural lighting all day. Updated kitchen with newer, barely used modern appliances and updated cabinetry and countertops. Reverse Osmosis Water softener has been installed to provide the top quality water. On the main floor, you will find a light and bright living room that leads to the oversized screened-in private lanai. Enjoy the wildlife whilst sitting up in the mature trees. The dining area also has a breakfast bar for additional entertaining space. Down the hallway you will find the primary bedroom with two closets, balcony access and entrance to the hallway renovated full bathroom. Also on the main floor is a stackable washer and dryer and large storage closet. Take the serial staircase to the secondary bedroom loft with full bathroom and two closets. The oversized closet is ideal for a walk-in or year round storage. The community is full of life and energy, especially in the winter seasons, and with all of the waterfront dining, parks and attractions nearby, you will always have something to do! Conveniently located near shopping, dining, downtown Venice, Sarasota, major roadways and schools.

109 Woodland Place, Osprey
1819 Highland Road, Osprey
$319,000
2 Beds ⋅ 3 Baths ⋅ Towns-End Shores SubDv. ⋅ 34229 Zip Code
This beautifully appointed 2-bedroom, 2-bath townhome offers a wonderful blend of comfort, privacy, and Florida living in "The Osprey", a community of just 12 residences. The open-concept floor plan features high ceilings, generous living spaces, and large windows that fill the home with an abundance of natural light. The spacious owner’s retreat provides a peaceful setting for relaxation, while the second bedroom offers flexibility for guests, an office, or additional living space. Located in flood zone X, the oversized garage offers the perfect opportunity to add to your living space or provides an abundance of storage. The private outdoor spaces are a true highlight of the home. The beautifully landscaped yard and garden create a peaceful retreat, while the private terrace provides an ideal setting for al fresco dining and entertaining. A mature specimen lemon tree serves as the star of the garden, providing fresh lemons for lemonade, cooking, or homemade limoncello. Residents also enjoy access to the community pool, adding to the relaxed, resort-like feel of the property. The location is equally appealing. Situated in Osprey, the property is conveniently located near the beaches of Casey Key, local shops, restaurants, and a variety of recreational amenities directly across the street from Oscar Scherer State Park, home to over 17 miles of trails and nearly 1400 acres of natural habitats, launch a kayak, or simply take in the peaceful surroundings along the water. The nearby Casey Key Resort offers the opportunity to enjoy its pool, facilities, and restaurant for the day, providing an additional resort-style experience close to home. Downtown Sarasota and downtown Venice are also easily accessible, offering an outstanding selection of dining, shopping, cultural attractions, and entertainment. With its private outdoor spaces, community pool, beautiful natural light, and convenient location, this exceptional townhome offers a refined yet relaxed approach to coastal Florida living. Whether enjoyed as a full-time residence or a seasonal retreat, this home offers an exceptional opportunity to embrace the Florida lifestyle.

1819 Highland Road, Osprey
570 Blackburn Point Road Unit 36, Osprey
$99,500
Osprey Avenue Sub SubDv. ⋅ 34229 Zip Code
This high end, hurricane rated building sits ideally located between Sarasota and Venice. It is just minutes away from Midnight Pass. This slip holds a boat 32.5' in length, 9' in height and 10' in width. The marina is professionally staffed and is opened 7 days a week. Amenities include outside service racks, wash down stations, pump out, 90 octane rec fuel, water and electric on the docks, fillet tables, outside patio area, fresh deli, drinks, ice, snacks, live and frozen bait. Enjoy your day out on the water and when you return, the staff will flush your engines, wash around the waterline and put your boat to bed, leaving you the freedom to just enjoy boating.

570 Blackburn Point Road Unit 36, Osprey
570 Blackburn Point Road Unit 23, Osprey
$89,000
Dry Slips At Bellagio Village SubDv. ⋅ 34229 Zip Code
Extra-wide indoor boat rack accommodating vessels up to 33' L x 11.1' W x 9.3' H, with quick access to Midnight Pass and Venice Inlet. Marina amenities include call-ahead splash service, fuel, ice, bait and tackle, fish cleaning station, adjacent restaurant, maintenance racks, and wash-down service after each use. Condo fees cover in and outs, insurance, marina and building maintenance, staff, and equipment. Indoor storage offers year-round peace of mind and protection from the elements, while rental potential may make this an excellent Sarasota waterfront investment opportunity. Buyer to verify vessel fit and rental rules with the marina/association.

570 Blackburn Point Road Unit 23, Osprey
116 Woodland Place Unit 116, Osprey
$249,900
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
4296 Expedition Way Unit 104, Osprey
$289,000
2 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code
Welcome to Bay Street Village in Osprey, gorgeous gated community where maintenance-free living awaits. This immaculate end-unit condo freshly painted with new LVP stairs and flooring features 2 bedrooms, 2 bathrooms, garage, located beneath the unit and offers a private interior stairway leading to your second-floor residence. Open-concept living and dining area are perfect for entertaining beautiful kitchen with center island, walk-in pantry and stainless steel appliances. The 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 amenities, including a sparkling pool and a fitness center, along with plenty of guest parking. The community is dog-friendly, with a fantastic dog park just a short walk outside the gate. Outdoor enthusiasts will appreciate the easy access to the Legacy Trail right on Bay Street. Pine View School for the Gifted (grades 2-12) is conveniently located on the next street. Bay Street offers easy access to Nokomis Beach and the world-famous Siesta Key Beach. Close to shopping and restaurants.

4296 Expedition Way Unit 104, Osprey
320 Tropic Drive, Osprey
$185,000
2 Beds ⋅ 2 Baths ⋅ Arbors SubDv. ⋅ 34229 Zip Code
Virtually Staged. Welcome to this Partially Furnished home in the desirable 55+ cooperative community of The Arbors!This property in The Arbors stands out primarily for its rare inclusion of a separate adjacent lot, providing significant flexibility for either added privacy or future expansion. This is a very special property as it includes a second lot with an existing beautiful gazebo and lighting. The possibilities are endless as this space can be kept for leisure or used to build an additional home. The seller invested $28,000 in fundamental upgrades, includin g: New subflooring and moisture barrier, Laminate flooring throughout main living areas and bathrooms, and Fresh carpeting in bedrooms and the Florida Room. The interior features an open floor plan with two bedrooms. The primary suite includes dual walk-in closets and a ensuite bath. This home is light and bright with a comfortable Florida Room—perfect for morning coffee or evening relaxation. A large outdoor shed offers abundant storage and includes a washer and dryer. This desirable lot is located in the pet-friendly section of the park. Monthly dues include an impressive list of amenities: access to the clubhouse, heated community pool, lawn service, water, garbage pickup, sewer, cable TV, and internet. The Seller recently spent $28,000 on a new sub floor, new moisture barrier, New laminate flooring in kitchen, dining, great room, bathrooms, and hallway. New carpet in both bedrooms and Florida room. There’s even an on-site storage area for your boats, RVs, or kayaks for a small fee! The location is unbeatable—close to Casey Key, the Legacy Trail, Walmart, shopping, restaurants and the Nokomis and Siesta Key Beaches. You’re also just a short drive from historic downtown Venice and the lively attractions of downtown Sarasota. The community also offers an active clubhouse, heated pool, dog run, shuffleboard, exercise area, and regular social events.

320 Tropic Drive, Osprey
51 Macewen Drive Unit 12, Osprey
$275,000
1 Beds ⋅ 1 Baths ⋅ Windsor Lodge At The Oaks SubDv. ⋅ 34229 Zip Code
Situated in Windsor Lodge in The Oaks Clubside, this updated second floor condo has a kitchenette with quartz countertops, a modern bath, a bonus space set up as a small office area and in-unit laundry. An end unit, it has more windows than the typical interior location, filling the interior with wonderful natural light and offering sweeping views of Eagle #18 and lake. This immaculate condo is perfect for hosting out of town visitors, or for you to use as a weekend get-a-way. And, when you are not using it, the flexible rental policy allows you to easily lease the unit. Offered turnkey furnished and with the convenience of the Windsor Lodge pool and clubhouse just steps away, there is no better way to experience The Oaks with little effort and a lot of comfortable, maintenance-free enjoyment.

51 Macewen Drive Unit 12, 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
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