110 PINE AVENUE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 2,058 SqFt · $340/SqFt
Days on Market: 243
County: Sarasota
Subdiv/Community Name: Osprey Avenue Sub
Legal Subdivision Name: SAUNDERS V A RESUB
Year built: 1977
Garage: Yes 2 vehicles
Private Pool: Yes
Heart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your RV and all your toys. Lots of room for storage. Enjoy sunsets, steps to fishing pier, kayak launch, Spanish Pointe, Oscar Scherer State Park, and Pine View School. No restrictions. Move-in ready enjoying the Florida lifestyle! For outdoor enthusiasts, this location is unbeatable. Launch your kayak or paddleboard from a few steps away into Sarasota Bay, explore Mid night pass, Siesta Beach, nearby Bay Preserve at Osprey and Historic Spanish Point, close to Oscar Scherer State Park, Casey Key, Nokomis Beach. The large backyard offers ... Read more....»
571 PINE RANCH EAST ROAD
OSPREY FL 34229
Residential / Single Family Residence
5 Bed · 2 Bath · 1 Half Bath · 2,746 SqFt · $237/SqFt
Days on Market: 154
County: Sarasota
Subdiv/Community Name: Bay Oaks Estates
Legal Subdivision Name: BAY OAKS ESTATES UNIT 1
Year built: 1995
Garage: Yes 2 vehicles
Private Pool: Yes
One of the largest homes in Bay Oaks Estates, with the second-largest floor plan in the community, this 5-bedroom, 2.5-bath single-story pool retreat delivers the best of indoor-outdoor Florida living with flexible spaces for guests, work, and play. Curb appeal pops with a brick paver circular drive, lush, well-established landscaping highlighted by a mature magnolia and fragrant gardenias, and a covered, columned entry with French double doors and an arched transom. Inside, high ceilings and an abundance of natural light set a welcoming tone. The formal living and dining rooms flow to the heart of the home – a well-appointed ... Read more....»
659 RIVENDELL BOULEVARD
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 1 Half Bath · 2,292 SqFt · $283/SqFt
Days on Market: 16
County: Sarasota
Subdiv/Community Name: Rivendell
Legal Subdivision Name: RIVENDELL, THE WOODLANDS AT RIVENDELL
Year built: 2001
Garage: Yes 3 vehicles
Private Pool: Yes
Located within The Woodlands at Rivendell, this meticulously maintained single-family residence offers a sophisticated balance of comfort, functionality, and tranquil natural surroundings. Backing to a serene lake and protected preserve, the home enjoys exceptional privacy and peaceful water views. Designed with an open, split-bedroom floor plan, the residence features three bedrooms, two full baths, a dedicated office, and an additional pool bath—well suited for both everyday living and gracious entertaining. The owner’s suite serves as a private retreat, highlighted by a tray ceiling, two walk-in closets, and a spa-inspired bath with dual vanities, a soaking tub, Roman shower, and private ... Read more....»
522 LUMINARY BOULEVARD
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 2,320 SqFt · $279/SqFt
Days on Market: 23
County: Sarasota
Subdiv/Community Name: Willowbend
Legal Subdivision Name: WILLOWBEND PH 3
Year built: 2005
Garage: Yes 2 vehicles
Waterfront: Yes
This exquisite three-bedroom, three-bath-plus-den, Lee Wetherington built home exemplifies intelligent design and beauty in the community of Willowbend. This Ashley floor plan is thoughtfully oriented to the south, allowing for abundant natural light and stunning lakefront views. The residence features inviting curb appeal with a paver-accented driveway and walkway, leading to an impressive custom double-door entry. Inside, high-end upgrades and recent enhancements contribute to the home's timeless character. The sophisticated interior showcases clean lines, intricate tray ceilings and tile flooring throughout main living areas. Crown molding and impressive lighting fixtures add elegance to the space. The gourmet kitchen is a ... Read more....»
472 PARK TRACE BOULEVARD
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 2 Bath · 2,217 SqFt · $291/SqFt
Days on Market: 5
County: Sarasota
Subdiv/Community Name: Park Trace Estates
Legal Subdivision Name: PARK TRACE ESTATES
Year built: 2002
Garage: Yes 2 vehicles
Private Pool: Yes
Located in the highly desired Park Trace Estates, this beautifully maintained 4-bedroom pool home sits on a premium corner lot and is truly move-in ready. Recent upgrades include a NEW TILE ROOF and IMPACT WINDOWS, offering peace of mind and energy efficiency. The entire house has a LEAFHOME WATER FILTRATION SYSTEM, ensuring clean, high-quality water throughout. The spacious layout is perfect for both everyday living and entertaining, with seamless indoor-outdoor flow to the private SALT WATER POOL. Enjoy mature landscaping on the large corner lot providing added space and privacy, with plenty of room to enjoy the beautiful surroundings. ... Read more....»
819 SHADOW BAY WAY
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 2 Bath · 2,145 SqFt · $298/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: Rivendell
Legal Subdivision Name: RIVENDELL
Year built: 2002
Garage: Yes 2 vehicles
Private Pool: Yes
Community Pool: Yes
Welcome to this stunning 2,145-square-foot pool home in the premier community of Rivendell where maintenance-free living meets tropical elegance. Perfectly positioned on a beautifully landscaped corner lot, this meticulously maintained residence offers timeless style and thoughtful updates throughout. Recent improvements include a 2026 irrigation valves, 2025 roof replacement, 2024 pool pump, and a 2017 AC system, providing peace of mind for years to come. Step onto the inviting front porch the perfect setting for morning coffee. Enter through the elegant glass front door into a bright, open foyer filled with natural light. The spacious split floor plan seamlessly connects the ... Read more....»
767 FORDINGBRIDGE WAY
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 2,162 SqFt · $289/SqFt
Days on Market: 12
County: Sarasota
Subdiv/Community Name: Rivendell The Woodlands
Legal Subdivision Name: RIVENDELL WOODLANDS
Year built: 2002
Garage: Yes 2 vehicles
Set on a quiet cul-de-sac in The Woodlands at Rivendell, this furnished and thoughtfully maintained residence offers a peaceful setting surrounded by mature landscaping and wooded views. The extended foyer welcomes you into an open great-room layout spanning nearly 2,200 square feet, where high tray ceilings, plantation shutters, and hardwood flooring create a cohesive flow throughout the main living areas. The great room features floating shelves, an electric fireplace, and walls of glass sliders that open to a serene, screen-enclosed pavered patio overlooking private natural surroundings—ideal for morning coffee or evening relaxation. The gourmet kitchen was completely updated in 2022 and ... Read more....»
4428 CONCHFISH LANE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 2 Bath · 1,861 SqFt · $322/SqFt
Days on Market: 256
County: Sarasota
Subdiv/Community Name: Not Applicable
Legal Subdivision Name: PALMS/CASEY KEY
Year built: 2018
Garage: Yes 2 vehicles
Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not considered a high-risk zone (Zone X) and features four spacious bedrooms and two full bathrooms, along with a two car garage and a large driveway for additional parking. Step into the kitchen, and you'll find elegant quartz countertops, upgraded 42" Timberlake latte cabinets, a stylish backsplash, a large walk-in pantry, and stainless-steel appliances. The master retreat offers a tranquil area with a spacious bedroom. Plantation shutters and 18x18 tiles complemented by hard floors throughout the entire house. ... Read more....»
104 PARK TRACE BOULEVARD
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 2,557 SqFt · $233/SqFt
Days on Market: 76
County: Sarasota
Subdiv/Community Name: Park Trace Estates
Legal Subdivision Name: PARK TRACE ESTATES
Year built: 2002
Garage: Yes 2 vehicles
Private Pool: Yes
Welcome to this elegant and spacious luxury pool home offering over 2,500 square feet of refined living in one of the most desirable communities along the Gulf Coast. With a freshly painted exterior, stunning hardwood floors throughout, and an exceptional layout designed for both comfort and style, this residence is move-in ready and perfectly suited for modern living. Boasting four bedrooms, including a private guest suite area, and three beautifully appointed baths, the home offers flexible space ideal for hosting family and friends. Expansive living areas flow seamlessly to the outdoor oasis, where a sparkling pool creates the perfect backdrop ... Read more....»
711 SHADOW BAY WAY
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 2 Bath · 2,133 SqFt · $274/SqFt
Days on Market: 72
County: Sarasota
Subdiv/Community Name: Rivendell
Legal Subdivision Name: RIVENDELL
Year built: 2002
Garage: Yes 2 vehicles
Condition, Condition, Condition – AND Location, Location, Location!! This house is a real gem! Immaculate and beautifully updated, it features 4 bedrooms (or 3 plus a den with a closet) in a split plan that provides privacy for owners and guests. When you sit on the front porch of this contemporary style home, you’ll enjoy an uninterrupted front yard, since the garage opens to the rear of the lot. The inviting front porch and foyer lead you into an open floor plan with high ceilings and special decor touches. The dining room has space for an expanding table for large ... Read more....»
1337 COPPERWOOD DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 2,172 SqFt · $267/SqFt
Days on Market: 122
County: Sarasota
Subdiv/Community Name: Willowbend
Legal Subdivision Name: WILLOWBEND PHASE 3
Year built: 2004
Garage: Yes 2 vehicles
Private Pool: Yes
This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases meticulous attention to detail with features such as high ceilings, architectural details like arches and insets, sconce lighting, crown molding, tray ceilings and shutters. The layout promotes a refined atmosphere where the subtle color palette, which is newly painted, fosters a seamless transition between indoor and outdoor spaces, ideal for enjoying Florida's ... Read more....»
583 PINE RANCH EAST ROAD
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 2 Bath · 2,203 SqFt · $263/SqFt
Days on Market: 93
County: Sarasota
Subdiv/Community Name: Bay Oaks Estates
Legal Subdivision Name: BAY OAKS ESTATES
Year built: 1996
Garage: Yes 2 vehicles
Private Pool: Yes
Beautifully updated 4BR/2BA pool home in the sought-after Bay Oaks Estates community of Osprey. This single-story residence's backyard borders the Legacy Trail and includes a private gate for direct trail access. Inside, high ceilings and natural light complement luxury vinyl plank flooring, fresh paint, new doors, baseboards, and fixtures. The kitchen features quartz countertops, marble backsplash, recessed lighting, an undermount sink, and newer Whirlpool appliances. A split floor plan provides privacy with spacious bedrooms, including a primary suite with lanai access, two closets (one walk-in), and a spa-like bath with soaking tub, walk-in shower, and dual quartz vanities. The screened ... Read more....»
1036 OAK MEADOW LN
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 2 Bath · 2,186 SqFt · $247/SqFt
Days on Market: 125
County: Sarasota
Subdiv/Community Name: Rivendell
Legal Subdivision Name: RIVENDELL, UNIT 3-A
Year built: 2001
Garage: Yes 2 vehicles
Welcome to this attractive St. Charles floor plan found in the desirable Woodlands at Rivendell community! This charming home sits on a large corner lot directly across from the heated community pool and is within easy reach of the highly ranked Pine View School for the Gifted (Grades:2-12). Built in 2001, this well-maintained home features four bedrooms, or three bedrooms plus den with closet, and two full baths. The spacious great room includes living and dining areas, elegant crown moldings, tray ceilings, built-ins and plantation shutters for timeless style. The open kitchen offers a breakfast bar, Corian countertops, and a ... Read more....»
742 HARMS DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 1,293 SqFt · $398/SqFt
Days on Market: 135
County: Sarasota
Subdiv/Community Name: Harms Sub
Legal Subdivision Name: HARMS SUB
Year built: 1981
Garage: Yes 2 vehicles
Private Pool: Yes
Beautifully renovated and now offered at a newly reduced price, this turnkey property is a fantastic opportunity with motivated sellers. Set on just over half an acre along a private, tree-lined street the home is surrounded by lush tropical landscaping that creates a peaceful and secluded feel. Inside you’ll find a spacious layout with modern finishes and seamless indoor-outdoor living with a heated pool and screened lanai. The home has been fully updated and has a strong history as a successful income-producing rental. Major improvements include a full interior renovation, new roof and pool cage rescreened (2021), pool pump (2022), ... Read more....»
508 MEADOW SWEET CIRCLE
OSPREY FL 34229
Residential / Single Family Residence
2 Bed · 2 Bath · 1,604 SqFt · $277/SqFt
Days on Market: 152
County: Sarasota
Subdiv/Community Name: Rivendell
Legal Subdivision Name: RIVENDELL
Year built: 2000
Garage: Yes 2 vehicles
PRICE IMPROVEMENT!! The Cottages of Rivendell are highly desirable residences, offering an exclusive community with only 84 homes. Each home is surrounded by lush landscaping and tree-lined streets, contributing to the area's charm and appeal. This home features 2 bedrooms and 2 bathrooms, as well as a versatile den or office space. It is an ideal choice for those seeking a seasonal residence in Florida, or for anyone looking to downsize without sacrificing comfort or style. Residents enjoy the best of the Florida lifestyle, with close proximity to beautiful beaches-just 2 stoplights away. Additionally, the community ... Read more....»
32 BAY AVENUE
OSPREY FL 34229
Residential / Single Family Residence
2 Bed · 2 Bath · 2,148 SqFt · $203/SqFt
Days on Market: 130
County: Sarasota
Subdiv/Community Name: Bay Acres Sub
Legal Subdivision Name: BAY ACRES - RESUB
Year built: 1962
Garage: Yes 2 vehicles
Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless steel appliances—all completed in 2022. Yard was completely fenced in 2024. With ample square footage, there’s even potential to add a third bedroom, offering flexibility for your needs. All major systems have been upgraded; now this home is waiting for your personal touch. ... Read more....»
352 GLENWOOD AVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 1,300 SqFt · $330/SqFt
Days on Market: 280
County: Sarasota
Subdiv/Community Name: Osprey Park
Legal Subdivision Name: SIESTA REV RESUB OF PT
Year built: 2021
Garage: Yes 1 vehicles
Beautifully Maintained 3-Bedroom Home with No HOA or Deed Restrictions Welcome to this immaculate 3-bedroom, 2-bath home, newly built in 2021 and perfectly located just minutes from top-rated beaches, shopping, dining, and entertainment. This move-in-ready home offers a clean, modern design with a spacious open floor plan that’s ideal for both relaxing and entertaining. Enjoy cooking in the stylish open kitchen, complete with granite countertops and ample cabinet space. Luxury vinyl flooring runs throughout the home, adding durability and a sleek, contemporary feel. With no HOA, CDD, or deed restrictions, this property provides true freedom and flexibility—bring your boat, RV, or other recreational ... Read more....»
524 SARABAY ROAD
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 1,760 SqFt · $238/SqFt
Days on Market: 64
County: Sarasota
Subdiv/Community Name: Bay Acres Sub
Legal Subdivision Name: BAY ACRES - RESUB
Year built: 1956
Garage: No
Location, Location. In the Heart of Osprey, centrally located in the highly sought-after well-established Bay Acres Community. Lowest priced home west of the Taril. These 3 bedrooms 2 bath ranch home is West of 41 within 10-minute commutes to downtown Sarasota and downtown Venice, Florida. Across the street from Walmart with bus transportation to Sarasota and Venice. You can walk to Walmart, the post office and two Tiki bars. You can launch your kayak from the private waterfront park on a protected bay with dockage for boats up to 22 feet. There is a waiting list for the dockage. Bay ... 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.
