Osprey, FL Homes

/89
$1,825,000
- 4 Beds
- 3.5 Baths
- 4,388 Sq Ft
401 Walls Way, Osprey, FL 34229

Recently appraised for over 2 million, Seller relocating. Exquisite Executive Home in The Oaks Clubside, Step into elegance and luxury with this stunning two-story masterpiece. Perfectly situated to capture breathtaking views of the 9th Fairway on the Heron Course and a serene lake preserve, this home offers a rare combination of sophistication, comfort, and unparalleled design. Gourmet Kitchen:

Lee Brewer

RE/MAX ALLIANCE GROUP

(941) 207-3151

401 Walls Way, Osprey, FL 34229
/30
$10,050 per month
- 3 Beds
- 3.5 Baths
- 2,716 Sq Ft
- Condo for Rent
14021 Bellagio Way Unit 401, Osprey, FL 34229

2025 AVAILABLE: DEC.2026 AVAILABLE: MAR, APR.BOOK AT: $10,050/PER MONTH (SEASON IS DEC-APRIL, 1 MONTH MINIMUM)*PRICES MAY VARY DEPENDING ON NUMBER OF NIGHTS BOOKED*This is your chance to enjoy the Florida Coastal lifestyle that you've been dreaming about! This rarely available very quiet, 3 bedroom, 3 1/2 bath 2,700 square foot penthouse suite is the epitome of luxury. This

Jeremy Myers

COMPASS PROPERTY MANAGEMENT LLC

(941) 274-3817

14021 Bellagio Way Unit 401, Osprey, FL 34229
/2
$140,000 Sold May 02, 2025
- 1,173 Sq Ft
- $119/SF
- 9 Days On Market
- 3 Beds
- 1 Bath
- Built 1979
234 Patterson Ave, Osprey, FL 34229

Welcome to 234 Patterson Ave, a charming single-family home nestled in the heart of Osprey, Florida. This home went through a small fire in the living room and the ceilings and some walls need drywalled back in and it needs a new electric box to go with the new wiring installed this month for $5000. This owner has updated some much on this home and with not a ton of repairs left for someone to

Sean Seward KELLER WILLIAMS ISLAND LIFE REAL ESTATE

234 Patterson 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

/88
$1,200,000
- 4 Beds
- 3 Baths
- 3,379 Sq Ft
201 Eaglenook Way, Osprey, FL 34229

Nestled in the exclusive Pine Ranch community of Osprey, Florida, this 4-bedroom, 3-bath estate offers a rare opportunity for those seeking privacy, tranquility, and a healthier way of living. Situated on just over two acres of lush, tree-canopied land, this meticulously maintained home is designed for comfort, sustainability, and connection to nature. From the moment you enter the long private

Dawn Bear

WILLIAM RAVEIS REAL ESTATE

(941) 757-8209

201 Eaglenook Way, Osprey, FL 34229
/83
$2,200 per month
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Condo for Rent
129 Woodland Place, Osprey, FL 34229

One or more photo(s) has been virtually staged. AVAILABLE FURNISHED FOR $3,300. Step into the serene lifestyle at 129 Woodland Place, a charming 2-bedroom, 2-bathroom condo in the peaceful Pine Run community of Osprey, Florida. Spanning 1,223 square feet, this home boasts an open layout with soaring ceilings that invite natural light to fill the space. The living and dining areas seamlessly

Paulina Vasiliev

KELLER WILLIAMS ON THE WATER S

(941) 394-8767

129 Woodland Place, Osprey, FL 34229
/2
$1,600,000 Sold May 01, 2025
- 5,987 Sq Ft
- $267/SF
- 1 Day On Market
- 5 Beds
- 7.5 Baths
- Built 1991
916 MacEwen Dr, Osprey, FL 34229

Situated on a double lot behind the secure gates of The Oaks, this two story 5 bedroom home, with 7.5 bathrooms, boasts fantastic potential and excellent bones. The only thing it needs is for you to put your personal touch on it and make it your own. As you pull up to this home, using the front circular driveway, or the back driveway with access to the 4 CAR GARAGE, you will immediately be taken

Steve Abbe COLDWELL BANKER REALTY

916 MacEwen Dr, Osprey, FL 34229

/30
Est $373,915 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
4202 Frontier Ln, Osprey, FL 34229

4202 Frontier Ln, Osprey, FL 34229

/100
$700,000 Open Sun 1PM - 4PM
- 3 Beds
- 2 Baths
- 1,736 Sq Ft
14041 Bellagio Way Unit 315, Osprey, FL 34229

SIGNIFICANT PRICE IMPROVEMENT! IF YOU HAVE BEEN WAITING FOR A FANTASTIC WATERFRONT PROPERTY AND PRICE.. THIS IS THE ONE! *No storm damage.* Step into waterfront luxury living at its finest in Osprey Harbor Village, a coastal gem perfectly situated between Sarasota and Venice, offering easy access to Siesta Key, Nokomis Beach, and Venice Beach. This sought-after marina community is the epitome of

Dawn Bear

WILLIAM RAVEIS REAL ESTATE

(941) 207-5944

14041 Bellagio Way Unit 315, Osprey, FL 34229
/18
$4,500 per month
- 3 Beds
- 2.5 Baths
- 1,937 Sq Ft
- Condo for Rent
260 Hidden Bay Dr Unit 204, Osprey, FL 34229

Property Id: 18124583 bedroom 2.5 bath waterfront condo is immaculate and the perfect place for a seasonal snow bird rental, annual rental or Florida vacation (1 month minimum). Lanai that reveals a view of the bay and AMAZING SUNSETS. The unit has laundry room with washer, dryer, sink. The kitchen has granite counter tops ,fully equipped. . The master suite has a king size bed, 2 large

260 Hidden Bay Dr Unit 204, Osprey, FL 34229
/2
$875,000 Sold May 01, 2025
- 2,329 Sq Ft
- $376/SF
- 8 Days On Market
- 3 Beds
- 2 Baths
- Built 2002
851 E Bay St, Osprey, FL 34229

**BEAUTIFULLY RENOVATED, PRIVATE OASIS AWAITS on this OVERSIZED 1.37 ACRE ESTATE with NO HOA** This GREEN BUILT (insulated concrete form constructed), Move-In Ready Residence offers 3-BEDS and 2-FULL BATHS, while Recent UPDATES include beautiful Flooring, Impressive Primary Bedroom Suite with walk-in closet and Stunning Primary Bath featuring dual vanities, custom-tiled shower and soaking tub, a

Mark Lyda GENEROUS PROPERTY

851 E Bay St, Osprey, FL 34229

/39
Est $430,226 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
4234 Frontier Ln Unit 101, Osprey, FL 34229

4234 Frontier Ln Unit 101, Osprey, FL 34229

/61
$550,000
- 4 Beds
- 2.5 Baths
- 2,045 Sq Ft
12689 Promenade Estates Blvd, Osprey, FL 34238

Stunning Newer Home in Promenade Estates, Palmer Ranch. Welcome to this immaculate 4-bedroom, 2.5-bathroom single-family home situated on a prime corner lot in the sought-after Promenade Estates community, located in the heart of Palmer Ranch, Sarasota. Built in 2021, this property offers contemporary design, thoughtful upgrades, and the perfect blend of comfort and style. This bright and

Lee Brewer

RE/MAX ALLIANCE GROUP

(941) 353-2706

12689 Promenade Estates Blvd, Osprey, FL 34238
/41
$2,400 per month
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Condo for Rent
4214 Frontier Ln Unit 102, 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! Welcome to this lovely, fully furnished, 2-bedroom, 2-bathroom condo in Osprey! This condo is ready to welcome your entire family, complete with bright and airy spaces, spacious bedrooms, and a coastal vibe perfect for the ideal Florida lifestyle! Not

Christopher Plemenos

4214 Frontier Ln Unit 102, Osprey, FL 34229
/2
$395,000 Sold Apr 30, 2025
- 1,767 Sq Ft
- $224/SF
- 81 Days On Market
- 3 Beds
- 2 Baths
- Built 1960
418 Sarabay Rd, Osprey, FL 34229

One or more photo(s) has been virtually staged. NEW PRICE IMPROVEMENT! Welcome to 418 Sarabay Rd, a lovely old-Florida home "West of Trail" in the charming community of Osprey, exuding a small-town feel, but just minutes away from all the conveniences and excitement of Sarasota and Venice! You and your guests will be drawn to spend lots of time in this fully fenced private oasis with its large

Tracey Fiedler DALTON WADE INC

418 Sarabay Rd, Osprey, FL 34229

/51
Est $432,281 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
96 Navigation Cir Unit 101, Osprey, FL 34229

96 Navigation Cir Unit 101, Osprey, FL 34229

/65
$449,000
- 2 Beds
- 2 Baths
- 1,411 Sq Ft
117 Villa Dr Unit 117, Osprey, FL 34229

LET'S GO FISHING! / BEST PRICE IN SARASOTA COUNTY / SALTWATER CANAL VILLA AND YOU OWN THE DOCK! The Gulf is your new backyard with this best priced waterfront villa in Osprey, FL. If you love fishing, diving, sailing, or cruising on your boat, this wonderful 2 Bed Villa with a deeded dock could be for you. This is the Easy Florida Lifestyle you have dreamed about. Your boat dock features a

Bill Garrison

RE/MAX PLATINUM

(941) 352-8392

117 Villa Dr Unit 117, Osprey, FL 34229
/23
$2,000 per month
- 2 Beds
- 2 Baths
- 1,325 Sq Ft
- Condo for Rent
236 Woodland Dr, Osprey, FL 34229

Property Id: 310276AVAILABLE MAY 15 to SEPTEMBER 15: Light, airy home in Pine Run overlooks established native landscaping. Copious sliding doors, windows & high ceilings. Beautifully updated kitchen offer views to outdoors. A nature lovers paradise, this laid-back, quiet & desirable community is close to Casey Key, Blackburn Point Park & Intracoastal Waterway. A rare find & well-kept

236 Woodland Dr, Osprey, FL 34229
/2
$318,000 Sold Apr 30, 2025
- 1,411 Sq Ft
- $225/SF
- 125 Days On Market
- 2 Beds
- 2 Baths
- Built 1972
115 Villa Dr Unit 115, Osprey, FL 34229

Welcome to your future waterfront retreat in the heart of Osprey, where coastal living meets convenience. This beautifully appointed villa offers 1,411 square feet of thoughtfully designed living space, featuring two bedrooms and two bathrooms in a flowing, open-concept layout.The primary bedroom suite provides a peaceful sanctuary with an ensuite bathroom and generous closet space. Throughout

EJ Stukenborg KELLER WILLIAMS ON THE WATER S

115 Villa Dr Unit 115, Osprey, FL 34229

/82
Est $772,705 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,168 Sq Ft
250 Hidden Bay Dr Unit A-201, Osprey, FL 34229

250 Hidden Bay Dr Unit A-201, Osprey, FL 34229

/45
$679,600
- 3 Beds
- 2 Baths
- 2,302 Sq Ft
622 Pine Ranch Rd E, Osprey, FL 34229

This fabulous Turnkey, Tastefully Decorated Florida Pool home has everything you need to enjoy the Gulf Coast lifestyle.This three bedroom two bath home (plus a Den) sits on an oversized corner lot with a vinyl privacy fence and a side gate where you can store your water toys for your adventures on the Intercoastal Waterway. Lounge by the pool in your screened Lanai, cookout and listen to the

Terri Persing

PARADISE EXCLUSIVE INC

(941) 206-3903

622 Pine Ranch Rd E, Osprey, FL 34229
/56
$2,950 per month
- 2 Beds
- 2 Baths
- 1,850 Sq Ft
- House for Rent
574 Crane Prairie Way, Osprey, FL 34229

Annual unfurnished single-family pool home available in the Willowbend community of Osprey! This beautiful two-bedroom plus den, two-bath home is thoughtfully designed with a split floor plan surrounded by a center great room. The home features stainless steel appliances, gas range, beautiful wood flooring and built-in shelving in the den. The primary bedroom suite features dual walk-in closets,

Alex Lane PREMIER SOTHEBY'S INTERNATIONAL

574 Crane Prairie Way, Osprey, FL 34229
/2
$950,000 Sold Apr 29, 2025
- 2,570 Sq Ft
- $370/SF
- 82 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1993
32 Bayhead Ln, Osprey, FL 34229

Divine is in the details of this lovely 3 bedroom, 3 bath professionally redesigned home in the Oaks Preserve. No need to be concerned with remodeling, as this home underwent a complete renovation in 2023. This exceptional property meets the demands of today’s discriminating buyer, with a spacious chef’s gourmet kitchen featuring top of the line stainless appliances, a large prep island, quartz

Rosalie Phillips MICHAEL SAUNDERS & COMPANY

32 Bayhead Ln, Osprey, FL 34229

/98
Est $846,245 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,168 Sq Ft
250 Hidden Bay Dr Unit A504, Osprey, FL 34229

250 Hidden Bay Dr Unit A504, Osprey, FL 34229

/85
$2,390,000
- 3 Beds
- 3 Baths
- 3,681 Sq Ft
600 Eagle Watch Ln, Osprey, FL 34229

Located on one of the most desirable streets in The Oaks Clubside, this completely renovated pool home sits on a generous 0.71-acre lot with wide views of the third hole of the Heron Golf Course. Nearly every aspect of the property has been updated—new roof, impact-rated windows and doors, flooring, trim, countertops, appliances, resurfaced pool and spa, new pool cage, and a resurfaced

Joe Murphy

COLDWELL BANKER REALTY

(941) 274-4697

600 Eagle Watch Ln, Osprey, FL 34229
/10
$3,600 per month
- 2 Beds
- 2 Baths
- 1,604 Sq Ft
- House for Rent
508 Meadow Sweet Cir, Osprey, FL 34229

Property Id: 1775840Welcome to 508 Meadow Sweet Cir, Ospery - an elegantly furnished home with brand new Room and Board pieces. This stunning residence offers a bright, open floor plan with 2 bedrooms, 2 bathrooms and a study room. Conveniently located 5 MINUTES walking distance to the prestigious Pine View school, this home is also near pristine beaches, shopping, and dinning,

508 Meadow Sweet Cir, Osprey, FL 34229
/2
$165,000 Sold Apr 28, 2025
- 1,223 Sq Ft
- $135/SF
- 53 Days On Market
- 2 Beds
- 2 Baths
- Built 1980
235 Woodland Dr Unit 235, Osprey, FL 34229

Welcome to 235 Woodland Drive in sunny Osprey, FL—located between Sarasota and Venice so you can easily enjoy the beaches, shopping, arts and entertainment of both towns. This 1,223 square-foot home is all about easy living, featuring an open floor plan and soaring ceilings that let in tons of natural light. You’ll love the sun-drenched living and dining areas, with huge sliding doors that open

Priscilla Adams COMPASS FLORIDA LLC

235 Woodland Dr Unit 235, Osprey, FL 34229

/50
Est $1,134,348 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,377 Sq Ft
3973 Waypoint Ave, Osprey, FL 34229

3973 Waypoint Ave, Osprey, FL 34229

/72
$2,500,000
- 5 Beds
- 7 Baths
- 6,001 Sq Ft
340 Osprey Point Dr, Osprey, FL 34229

Introducing The Grand Estate at The Oaks Bayside—a true masterpiece of refined living within one of Sarasota’s most prestigious gated communities. Surrounded by majestic oak trees and lush tropical landscaping, this extraordinary residence offers the perfect blend of elegance, comfort, and privacy. A brand-new roof (2024) crowns this sprawling estate, while a pavered circular driveway leads to a

Lee Brewer

RE/MAX ALLIANCE GROUP

(941) 390-3295

340 Osprey Point Dr, 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
$179,000 Sold Apr 28, 2025
- 1,119 Sq Ft
- $160/SF
- 57 Days On Market
- 2 Beds
- 2 Baths
- Built 1979
312 Tropic Dr, Osprey, FL 34229

Welcome to your dream home in a vibrant 55+ community! This charming residence offers 2 spacious bedrooms and 2 full bathrooms, perfect for comfortable living. Enjoy the Florida lifestyle with two screened-in porches, ideal for relaxing or entertaining. The home features a convenient laundry room and ample storage space. Equipped with hurricane windows, this home provides peace of mind. The roof

Michelle Ward COMPASS FLORIDA LLC

312 Tropic Dr, Osprey, FL 34229

/53
Est $602,282 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,133 Sq Ft
4421 Conchfish Ln, Osprey, FL 34229

4421 Conchfish Ln, Osprey, FL 34229

/37
$878,000 Open Sun 1PM - 4PM
- 3 Beds
- 2.5 Baths
- 2,168 Sq Ft
260 Hidden Bay Dr Unit B 305, Osprey, FL 34229

3 Bed | 2.5 Bath | Den w/ Murphy Bed | Gulf & Bay Views | Screened Lanai | Impact Glass | Pool | Tennis | Pickleball | Gated Waterfront CommunityWelcome to Edgewater at Hidden Bay, where stunning Gulf and Bay views set the stage for serene coastal living. This beautifully maintained, turnkey end unit offers 3 bedrooms, 2.5 baths, and a flexible den with a custom Murphy bed—perfect for hosting

Cathy Rustin FIRST LIGHT REAL ESTATE

260 Hidden Bay Dr Unit B 305, Osprey, FL 34229
/34
$1,850 per month
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
- Condo for Rent
1847 Highland Rd Unit 1859, Osprey, FL 34229

Beautiful Duplex Villa with community pool in a great area. Close to beaches, shopping & restaurants.

1847 Highland Rd Unit 1859, Osprey, FL 34229
/2
$744,800 Sold Apr 24, 2025
- 3,060 Sq Ft
- $243/SF
- 145 Days On Market
- 4 Beds
- 3 Baths
- Built 2002
448 Park Trace Blvd, Osprey, FL 34229

**MOTIVATED SELLERS – WILL OFFER CREDIT TOWARD A NEW ROOF WITH ACCEPTABLE OFFER!** Experience the ideal combination of elegance, comfort, and functionality in this custom-built pool home, thoughtfully crafted with premium upgrades and meticulously maintained over the years. Set on a spacious lot, this home boasts 4 bedrooms, 3 baths, a dedicated office, and an impressive array of features

Toni Zarghami KW COASTAL LIVING III

448 Park Trace Blvd, Osprey, FL 34229

/78
Est $570,933 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,678 Sq Ft
36 Bishops Court Rd Unit 111, Osprey, FL 34229

36 Bishops Court Rd Unit 111, Osprey, FL 34229

/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
/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
$315,000 Sold Apr 24, 2025
- 1,092 Sq Ft
- $288/SF
- 147 Days On Market
- 3 Beds
- 2 Baths
- Built 2004
214 Patterson Ave, Osprey, FL 34229

Welcome to your dream home in the enchanting village of Osprey! This inviting 3-bedroom, 2-bathroom block home is nestled on a tranquil street, surrounded by lush landscaped gardens. Designed with comfort and functionality in mind, the open-plan living and dining area provides an ideal space for gatherings, with a clear view into the fully remodeled kitchen. Whether cooking or entertaining, the

Lisa Bouck, PA RE/MAX ALLIANCE GROUP

214 Patterson Ave, Osprey, FL 34229

/13
Est $26,074 Not Listed For Sale
- Studio
570 Blackburn Point Rd Unit 33, Osprey, FL 34229

570 Blackburn Point Rd Unit 33, Osprey, FL 34229

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