Osprey, FL Homes

/49
$997,000
- 3 Beds
- 3 Baths
- 2,283 Sq Ft
172 Sea Anchor Dr, Osprey, FL 34229

Welcome to your dream home! This 3-bedroom, 3-Bath residence offers the perfect blend of comfort, style, and outdoor living. Step inside to an open floorplan featuring a spacious living area, modern kitchen with stainless steel appliances. The separate den allows the perfect place to work from home! The highlight of this home is the inviting saltwater pool and roomy screened lanai. New tile roof

Sharon Lewis GOLF & BAY PROPERTIES LLC

172 Sea Anchor Dr, Osprey, FL 34229
/15
$2,845 per month
- 3 Beds
- 2 Baths
- 1,650 Sq Ft
- House for Rent
124 Main St, Osprey, FL 34229

Furnished Seasonal or Annual Rental Steps from Water Access! Available April 20, 2025 | Pet-Friendly | Lawn Care IncludedRental Options:Peak Season (Jan Mar): $5,000/monthPre/Post Season (Dec & Apr): $4,000/monthOff-Peak (May Nov): $2,495/monthAnnual Lease: $2,845/month (12-month term)LOCATION, LOCATION, LOCATION Perfect for Outdoor

124 Main St, Osprey, FL 34229
/2
$880,000 Sold Apr 23, 2025
- 2,045 Sq Ft
- $430/SF
- 61 Days On Market
- 3 Beds
- 2 Baths
- Built 1978
1237 Flying Bridge Ln, Osprey, FL 34229

A Southbay Yacht & Racquet Club beauty! This home has been given meticulous care and offers an abundance of updates and upgrades. Popular Southbay community features a boating marina on the Inter coastal Waterway, making this one of the most sought after locations west of the trail! This airy and open floorplan is sure to please! There are so many delightful updates and improvements, I'll try to

Pat Williams PAT WILLIAMS REALTY, LLC

1237 Flying Bridge Ln, Osprey, FL 34229

/41
Est $1,233,678 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,416 Sq Ft
3932 Waypoint Ave, Osprey, FL 34229

3932 Waypoint Ave, Osprey, FL 34229

/37
$650,000
- 2 Beds
- 2 Baths
- 1,750 Sq Ft
242 Hidden Bay Dr Unit 603, Osprey, FL 34229

One of Sarasota’s Best-Kept Secrets! Top-Floor Bayfront Retreat in Hidden Bay. 2 Bed | 2 Bath + Den | Enclosed Lanai | 2-Car Garage | Offered Fully Furnished. Perched on the top floor of a premier building in the exclusive Hidden Bay gated community, this spacious and light-filled condo offers breathtaking, panoramic views of Sarasota Bay. A true diamond in the rough, this home is ready for your

Joy McGraw REAL ESTATE REFINED

242 Hidden Bay Dr Unit 603, Osprey, FL 34229
/41
$4,200 per month
- 4 Beds
- 3 Baths
- 2,077 Sq Ft
- House for Rent
534 Oak Bay Dr Unit 1, Osprey, FL 34229

New to the rental market, 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. Brand new interior paint and brand 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

Brian ODonnell,PLLC REALTY BY DESIGN LLC

534 Oak Bay Dr Unit 1, Osprey, FL 34229
/2
$807,000 Sold Apr 22, 2025
- 2,112 Sq Ft
- $382/SF
- 244 Days On Market
- 3 Beds
- 2 Baths
- Built 1975
124 Tina Island Dr, Osprey, FL 34229

***Amazing waterfront opportunity*** One of the lowest priced canal front properties between Sarasota and Venice*** This great waterfront location is in desirable Sorrento Shores with a new dock on a wide canal sitting on a large lot with great views This 3 bedroom 2 bath split plan has a large living/dining area and a separate office space. The kitchen area has a separate seating area with a

Glenn Davis COLDWELL BANKER SARASOTA CENT.

124 Tina Island Dr, Osprey, FL 34229

/47
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,261 Sq Ft
171 Edgewood Dr, Osprey, FL 34229

171 Edgewood Dr, Osprey, FL 34229

/72
$1,000,000
- 4 Beds
- 3 Baths
- 3,011 Sq Ft
1085 Mallard Marsh Dr, Osprey, FL 34229

Step into this beautifully renovated Rivendell home and discover a stunning pool and lanai area, thoughtfullydesigned for relaxation and enjoyment. Offering expansive lake views, this home provides a serene retreat in one ofthe area's most sought-after communities.Spanning over 3,000 square feet, this spacious residence features four bedrooms, three baths, and an upstairs bonusroom, making it a

Veronica Manes MICHAEL SAUNDERS & COMPANY

1085 Mallard Marsh Dr, Osprey, FL 34229
/18
$1,850 per month
- 2 Beds
- 1 Bath
- 950 Sq Ft
- House for Rent
455 Pennsylvania Ave, Osprey, FL 34229

Available mid APRIL 2025 NO PETS ~ NO SMOKING Unique property has a style all its own, including native wildflower/herbal garden and beach gear. Nestled away in the ole' Florida fishing Village of Osprey is this quaint quiet FULLY FURNISHED TURN KEY 2/1 offers:~Upgraded kitchen fully equipped with all the necessary essentials, ~Stainless steel appliances including

455 Pennsylvania Ave, Osprey, FL 34229
/2
$245,000 Sold Apr 21, 2025
- 1,316 Sq Ft
- $186/SF
- 103 Days On Market
- 2 Beds
- 2 Baths
- Built 1980
225 Woodland Dr, Osprey, FL 34229

This completely remodeled, GROUND LEVEL, 2/2 condo is available in a charming West of Trail community (but not in a flood zone) and is the hidden gem you've been looking for! Step inside and be captivated by artistic elegance. This home has been thoughtfully updated and features a new HVAC system in 2023, a kitchen remodel in 2023 including sleek new appliances (including an induction cooktop),

Priscilla Adams COMPASS FLORIDA LLC

225 Woodland Dr, Osprey, FL 34229

/28
Est $739,845 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,269 Sq Ft
127 Bishops Court Rd, Osprey, FL 34229

127 Bishops Court Rd, Osprey, FL 34229

/100
$1,595,000
- 3 Beds
- 2.5 Baths
- 2,425 Sq Ft
228 Saint James Park, Osprey, FL 34229

Experience the unparalleled charm and convenience of this golf course home in The Oaks Club, the country club community designed by noted Sarasota architect Bo MacEwen. 228 Saint James Park is an original Bo MacEwen design, is located on the leafy and quiet Saint James Park cul-de-sac, and directly overlooks the opening hole of the Heron golf course.This single-floor three-bedroom, two-and-a-half

Rosalie Phillips MICHAEL SAUNDERS & COMPANY

228 Saint James Park, Osprey, FL 34229
/23
$2,200 per month
- 3 Beds
- 2 Baths
- 1,430 Sq Ft
- Condo for Rent
137 Navigation Cir Unit 137, Osprey, FL 34229

Apply within 24 hours of your conducted showing and once approved you will be credited your application fees towards your first full month's rent! Don't miss this beautiful 3-bedroom, 2-bathroom fully furnished condo in Osprey! Complete with modern furniture, art, and fixtures that will make you feel like you're living the life of luxury. The state of the art kitchen is complete with granite

Christopher Plemenos

137 Navigation Cir Unit 137, Osprey, FL 34229
/2
$600,000 Sold Apr 18, 2025
- 2,887 Sq Ft
- $208/SF
- 24 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1995
402 Pine Ranch Rd E, Osprey, FL 34229

LLocated 1-2 mile from the legacy trail off Bay St. in Osprey. Built on one acre in 1995. This is a 3-bedroom 3.5 bath home that has a lot of potential. The large office in the front of the home could be made into a 4th bedroom. The family room has a fireplace, built-in shelving and has a view of the pool. The pool bath is behind the family room with direct access to the pool. The master suite

Ronnie Caron CARON REALTY INC

402 Pine Ranch Rd E, Osprey, FL 34229

/63
Est $1,047,913 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,115 Sq Ft
3929 Waypoint Ave, Osprey, FL 34229

3929 Waypoint Ave, Osprey, FL 34229

/80
$1,195,000
- 3 Beds
- 3 Baths
- 2,316 Sq Ft
3921 Waypoint Ave, Osprey, FL 34229

CASUAL, COASTAL ELEGANCE in this charming WATERFRONT community – BAYSIDE on LITTLE SARASOTA BAY! The Florida Lifestyle you’ve always dreamt of awaits you at Bayside on Little Sarasota Bay – a GATED ENCLAVE OF JUST 49 HOMES tucked away on the bay in Osprey Florida - one of our area’s best kept secrets ideally located between Sarasota & Venice! This delightful POOL HOME offers 3 BEDROOMS, 3 FULL

Julie Larson WHITE SANDS REALTY GROUP FL

3921 Waypoint Ave, Osprey, FL 34229
/49
$2,995 per month
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
- Condo for Rent
127 Explorer Dr Unit 127 Explorer Dr, Osprey, FL 34229

Great location - short drive to the best Florida beaches, golf clubs, Oscar Schrer State park, Legacy trail, right between cultural and culinary wealth of downtown Sarasota and Venice. Walking distance to Pine View School, playground and dog park across the street. Gated community with heated pool, fitness center and club house, newer buildings with hurricane -withstand features. One car garage

127 Explorer Dr Unit 127 Explorer Dr, Osprey, FL 34229
/2
$650,000 Sold Apr 18, 2025
- 2,431 Sq Ft
- $267/SF
- 113 Days On Market
- 3 Beds
- 2 Baths
- Built 1995
610 Pine Ranch Rd E, Osprey, FL 34229

Price Reduced on this Magnificent three bedroom, two bath home with den, heated pool, fenced yard for privacy in Bay Oaks Estates in Osprey. This fantastic, well maintained home has it all including a LOW annual fee of $270. Features include an updated kitchen with large farmer sink, quartz counters, Bosch Range with stainless hood, Bosch dishwasher, Samsung Refrigerator with plenty of storage,

Kim Klee COLDWELL BANKER REALTY

610 Pine Ranch Rd E, Osprey, FL 34229

/67
Est $569,433 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,890 Sq Ft
52 Bishops Court Rd Unit 113, Osprey, FL 34229

52 Bishops Court Rd Unit 113, Osprey, FL 34229

/48
$1,200,000
- 3 Beds
- 2 Baths
- 2,531 Sq Ft
142 Dory Ln, Osprey, FL 34229

Southbay Yacht & Racquet Club, The waterfront Community with Resort-Style Amenities. Welcome to this beautiful three-bedroom two-bathroom home featuring a private pool and spa, perfect for relaxing or entertaining year-round. Located in a highly sought-after waterfront community, this property offers access to a private marina, clubhouse, community pool and scenic park-ideal for enjoying the

Sharon Lewis GOLF & BAY PROPERTIES LLC

142 Dory Ln, Osprey, FL 34229
/51
$3,000 per month
- 2 Beds
- 2 Baths
- 1,857 Sq Ft
- House for Rent
531 Latitude Ln, Osprey, FL 34229

Annual unfurnished single-family home is available in the Willowbend community of Osprey! With some of the best lake views in Willowbend, this two-bedroom plus den, two-bath home features a large primary bedroom with dual sink main bath, walk-in shower and separate soaking tub. Additional features include stainless steel kitchen appliances, gas range, pantry and laundry room with utility sink.

Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

531 Latitude Ln, Osprey, FL 34229
/2
$26,000 Sold Apr 16, 2025
- 24 Days On Market
570 Blackburn Point Rd Unit 17, Osprey, FL 34229

New to the Osprey area and need to find a home for your boat? Or perhaps you already live in Sarasota County and are tired of the additional storm prep that is necessary to keep your boat safe and sound during Florida’s unpredictable weather…there is a solution! Consider this dry storage boat slip located just before the swing bridge to Casey Key (ICW Marker: 33 just north of Blackburn Point

Linda Williams GULF SHORES REALTY

570 Blackburn Point Rd Unit 17, Osprey, FL 34229

/39
Est $433,859 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
103 Explorer Dr Unit A-2, Osprey, FL 34229

103 Explorer Dr Unit A-2, Osprey, FL 34229

/79
$1,695,000
- 4 Beds
- 3.5 Baths
- 3,464 Sq Ft
402 Walls Way, Osprey, FL 34229

This captivating 4 bedroom (plus den/office), 3.5 bathroom home is ready to welcome you into its charm and warmth. Built in 2014 by Todd Johnson Homes, this courtyard-style residence effortlessly blends country modern flair with timeless elegance. Situated on an oversized, .64 acre corner lot in The Oaks Clubside, this home is made for Florida living with tile and hardwood floors, hurricane

Steve Abbe COLDWELL BANKER REALTY

402 Walls Way, Osprey, FL 34229
/25
$2,000 per month
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Townhouse for Rent
184 Explorer Dr, Osprey, FL 34229

FULLY FURNISHED Property available for $2000 from May 1, 2025 till December 15 ,2025. Tenant pays electricity and internet. INCLUDED IN THE LEASE :Water, sewer. If you are looking for the perfect Florida lifestyle, this is it. Conveniently located between Sarasota and Venice with #1 Siesta Key beach close by, this darling two-bedroom, two-bath, impeccably maintained, property move-in ready.

Claudia Dybala DALTON WADE INC

184 Explorer Dr, Osprey, FL 34229
/2
$1,050,000 Sold Apr 16, 2025
- 2,871 Sq Ft
- $366/SF
- 70 Days On Market
- 3 Beds
- 2 Baths
- Built 1979
247 Keel Way, Osprey, FL 34229

No hurricane problems here! impact windows and storm curtains on the lanai helped to keep this home safe. Also located in an X flood zone! This beautiful home located in "west of the trail", Southbay Yacht and Racquet Club is a very sought after location. One of the few communities with it's own marina and very reasonable dock rental fees only available to homeowners in the community. This home

Pat Williams PAT WILLIAMS REALTY, LLC

247 Keel Way, Osprey, FL 34229

/4
Not Listed For Sale
0 N Point Rd Unit MFRA4600038, Osprey, FL 34229

0 N Point Rd Unit MFRA4600038, Osprey, FL 34229

/40
$799,999
- 2 Beds
- 2 Baths
- 2,032 Sq Ft
242 Hidden Bay Dr Unit 302, Osprey, FL 34229

Spectacular water views. This two-bedroom condominium with den/office offers breathtaking views and amazing sunsets over little Sarasota Bay. This spacious unit is on the third level with elevator access and is part of the 12-plus-resort-style community. Features include high interior ceilings, PGT impact windows, new 2025 AC system and sliding glass doors, plantation shutter, Cortex luxury plank

Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

242 Hidden Bay Dr Unit 302, Osprey, FL 34229
/33
$3,695 per month
- 2 Beds
- 3.5 Baths
- 1,890 Sq Ft
- Townhouse for Rent
60 Bishops Court Rd Unit 114, Osprey, FL 34229

This is a rare opportunity to rent a luxury, unfurnished townhome located in the heart of the Oaks Preserve. Showcasing charming architectural details and quality finishes, this traditional-style home offers an inviting floor plan with two bedrooms, each featuring its own en-suite bath. The gracious living and dining areas flow seamlessly into a spacious and private outdoor living space that

Heidi Thompson STRINGER MANAGEMENT INC

60 Bishops Court Rd Unit 114, Osprey, FL 34229
/2
$385,000 Sold Apr 16, 2025
- 1,346 Sq Ft
- $286/SF
- 244 Days On Market
- 2 Beds
- 2 Baths
- Built 1963
329 Bay Vista Ave, Osprey, FL 34229

One or more photo(s) has been virtually staged. Come see this charming house in Osprey It features 2 bedrooms , 2 baths and a 2 car garage .The main bedroom has a sitting room. The kitchen has been updated with white cabinets with soft close drawers, granite countertops, stainless steel refrigerator and dishwasher. Save on electricity with the fully owned solar panel system. The entire yard is

Colette Jay HORIZON REALTY INTERNATIONAL

329 Bay Vista Ave, Osprey, FL 34229

/65
Est $1,151,131 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,314 Sq Ft
3937 Waypoint Ave, Osprey, FL 34229

3937 Waypoint Ave, Osprey, FL 34229

/61
$1,100,000
- 4 Beds
- 3 Baths
- 3,321 Sq Ft
742 Shadow Bay Way, Osprey, FL 34229

ARTHUR RUTENBERG HOME . . . FORMER MODEL . . . NEW ROOF . . . NEW INTERIOR AND EXTERIOR PAINT . . . HURRICANE DOUBLE-LAYER IMPACT WINDOWS . . . NEW OVEN . . . NEW BAMBOO FLOORING IN GUEST BEDROOMS . . . NEW PRIMARY AREA AC . . . Discover luxury in this Arthur Rutenberg former model home, located in the highly sought-after Woodlands at Rivendell community and award winning Pine View school

Reeny Kaney RE/MAX ALLIANCE GROUP

742 Shadow Bay Way, Osprey, FL 34229
/58
$4,800 per month
- 4 Beds
- 3 Baths
- 2,290 Sq Ft
- House for Rent
956 Scherer Way, Osprey, FL 34229

This luxuriously FULLY furnished 4 Bedroom Pool home is available starting April 15, 2025! It backs right onto the tropical preserves of Oscar Scherer Park and nestled in the sought-after community of The Woodlands at Rivendell providing the perfect blend of comfort, convenience, and natural beauty. Within the 400+ acres of lush landscapes in the neighborhood, enjoy the numerous scenic lakes,

Chantelle Edalgo KELLER WILLIAMS ON THE WATER S

956 Scherer Way, Osprey, FL 34229
/2
$945,000 Sold Apr 15, 2025
- 2,677 Sq Ft
- $353/SF
- 4 Days On Market
- 3 Beds
- 3 Baths
- Built 1978
128 Sea Anchor Dr, Osprey, FL 34229

New to the market, your dream home awaits in the exclusive private marina community of Southbay Yacht and Racquet Club. For boating enthusiasts, this is the opportunity you’ve been waiting for! In the sought-after Southbay Yacht and Racquet Club, this stunning residence combines spacious design with the best of Florida living, just steps from your boat. Imagine waking up and stepping out onto

Lisa Napolitano PREMIER SOTHEBYS INTL REALTY

128 Sea Anchor Dr, Osprey, FL 34229

/22
Est $310,281 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
101 Navigation Cir Unit 101, Osprey, FL 34229

101 Navigation Cir Unit 101, Osprey, FL 34229

/69
$1,100,000 Open House 5/17
- 5 Beds
- 4 Baths
- 3,938 Sq Ft
820 Placid Lake Dr, Osprey, FL 34229

HUGE PRICE IMPROVEMENT ***carpet was professionally cleaned 3/26/25*** Discover this beautiful, expansive 5-bedroom, 4-bathroom home offering 3,938 sq. ft. of living space on a 10,548 sq. ft. lot. Designed for both comfort and elegance, this residence features an open-concept floor plan with crown molding throughout, custom solid wood-designed cabinets, induction oven, a glass tile backsplash,

Ali Marks LOYD ROBBINS & CO. LLC

820 Placid Lake Dr, Osprey, FL 34229
/10
$1,750 per month
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
- Townhouse for Rent
1835 Highland Rd, Osprey, FL 34229

Charming 2 bedroom 2 bathroom villa in GREAT location just across the street from Oscar Scherer Park in Osprey! Nice and Bright with lovely open floor plan, ceiling fans, spacious eat-in kitchen, plenty of cabinet space, large kitchen island and washer & dryer in the unit. Tile flooring in main living space, carpet in both the bedrooms. Master Bedroom has ensuite bath with double sinks and

Roxanne Klopp JENNETTE PROPERTIES, INC.

1835 Highland Rd, Osprey, FL 34229
/2
$390,000 Sold Apr 15, 2025
- 1,334 Sq Ft
- $292/SF
- 21 Days On Market
- 2 Beds
- 2 Baths
- Built 1970
441 N Shore Dr, Osprey, FL 34229

Bring your BOAT or RV and store ON YOUR LOT. West of the Trail! Welcome home to Sorrento Shores, nestled perfectly between the vibrant communities of Sarasota and Venice, yet tucked away from the hustle and bustle of city life in the charming town of Osprey. This sought-after neighborhood offers spacious lots, a relaxed atmosphere, and the added bonus of low HOA fees and no CDD to worry

Dawn Barnett EXIT KING REALTY

441 N Shore Dr, Osprey, FL 34229

/40
Est $354,232 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
163 Explorer Dr Unit 103, Osprey, FL 34229

163 Explorer Dr Unit 103, Osprey, FL 34229

Showing Results 41 - 80, Page 2 of 18

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