Osprey, FL Homes

/2
$285,000 Sold May 30, 2025
- 1,255 Sq Ft
- $227/SF
- 112 Days On Market
- 2 Beds
- 2 Baths
- Built 1985
7102 Jessie Harbor Dr, Osprey, FL 34229

Spectacular views in all directions at highly desired Blackburn Harbor in Osprey. Tucked back and surrounded by mature and well groomed grounds you’ll park in your private under building parking space near your own large secured storage unit. Elevators take you up to Unit 71 where you’ll immediately appreciate the opportunity to utilize the covered outdoor space at the condo entrance to enjoy

Chris Rankin RE/MAX PALM REALTY

7102 Jessie Harbor Dr, Osprey, FL 34229

/35
Est $364,746 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,430 Sq Ft
4242 Frontier Ln Unit 106, Osprey, FL 34229

4242 Frontier Ln Unit 106, Osprey, FL 34229

/6
$29,900
- 2 Beds
- 1 Bath
124 Happy Haven Dr Unit 8, Osprey, FL 34229

Make your new home in Happy Haven, a well-maintained, professionally managed manufactured home community! Own a 1966, 1bed/1bath, 564 sqft. home in a great neighborhood. This one won't be on the market for long! Take advantage of this offer now and live in one of the state's most attractive areas. Let us show you around the place! Call and schedule a viewing today! Financing information available.

Tori Coil Happy Haven

124 Happy Haven Dr Unit 8, Osprey, FL 34229
/2
$855,000 Sold May 30, 2025
- 2,235 Sq Ft
- $383/SF
- 211 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2006
14021 Bellagio Way Unit 311, Osprey, FL 34229

Immerse yourself in the incredible views of Little Sarasota Bay & the Intracoastal waterway from this 3rd floor beautiful & spacious condominium. This upgraded end unit features 3 ensuite bedrooms, plus den, half bath & interior laundry room. The kitchen is a cook's delight with premium granite, upgraded wood cabinets & stainless steel appliances. The Primary bedroom offers expansive bay views &

Kristin O'Connor GULF TO BAY SOTHEBY'S INTERNAT

14021 Bellagio Way Unit 311, Osprey, FL 34229

/31
Est $575,209 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,004 Sq Ft
4400 Conchfish Ln, Osprey, FL 34229

4400 Conchfish Ln, Osprey, FL 34229

/55
$675,000
- 3 Beds
- 2 Baths
- 2,346 Sq Ft
563 Pine Ranch Rd E, Osprey, FL 34229

Step into your dream home in the sought-after Bay Oaks Estates where comfort, functionality, and location come together in perfect harmony. From the moment you arrive, you'll be captivated by the curb appeal and the welcoming presence that instantly feels like home. Beautifully designed this split-plan residence offers space, style, and seamless flow. The double-door entry opens into a foyer,

Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

563 Pine Ranch Rd E, Osprey, FL 34229
/62
$560,000 Sold May 29, 2025
- 1,935 Sq Ft
- $289/SF
- 68 Days On Market
- 3 Beds
- 2 Baths
- Built 1984
221 Sorrento Dr, Osprey, FL 34229

Discover your slice of paradise in the highly sought-after boating community of Sorrento Shores. This meticulously maintained and updated 3 bedroom, 2 bath home offers an unapparelled blend of comfort, convenience, and outdoor living, all west of Hwy 41.Key Features. *** Prime location: Nestled in Sorrento Shores, just minutes from Nokomis Beach, Oscar Scherer State Park, and an array of dining

Glenn Davis COLDWELL BANKER SARASOTA CENT.

221 Sorrento Dr, Osprey, FL 34229

/43
Est $381,355 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
4317 Expedition Way Unit 101, Osprey, FL 34229

4317 Expedition Way Unit 101, Osprey, FL 34229

/48
$335,000
- 3 Beds
- 2 Baths
- 1,889 Sq Ft
4256 Expedition Way Unit 107, Osprey, FL 34229

Welcome to Bay Street. Step into the Florida lifestyle you've been dreaming of with this beautifully designed second-floor condo featuring 3 bedrooms and 2 full baths at 4256 Exhibition Way #107, Osprey, FL. Built just eight years ago, this home blends modern comfort with timeless appeal, offering a setting that feels both inviting and refined. From the moment you walk in, your eyes are drawn to

Geri Scheckner Bright Realty

4256 Expedition Way Unit 107, Osprey, FL 34229
/2
$1,150,000 Sold May 28, 2025
- 2,521 Sq Ft
- $456/SF
- 20 Days On Market
- 2 Beds
- 3 Baths
- Built 1981
327 Sea Anchor Dr, Osprey, FL 34229

In the sought-after Southbay Yacht & Racquet Club, one of the premier boating communities on the southwest coast of Florida, this stunning home offers the ultimate in luxury living. With a community-owned marina and an expansive open layout, this property creates an ideal setting for relaxation and entertaining. This updated residence boasts volume ceilings, two fireplaces, built-in cabinetry and

Lisa Napolitano PREMIER SOTHEBYS INTL REALTY

327 Sea Anchor Dr, Osprey, FL 34229

/31
Not Listed For Sale
0 Webb St Unit A4546155, Osprey, FL 34229

0 Webb St Unit A4546155, Osprey, FL 34229

/32
$3,450,000
- 3 Beds
- 4.5 Baths
- 2,572 Sq Ft
135 Tina Island Dr, Osprey, FL 34229

Retreat to paradise in this stunning waterfront home, built new in 2011, in highly sought-after Sorrento Shores, Osprey. Perfectly situated on 210 feet of wide canal frontage, this residence offers deep water access with no bridges to the bay—a dream for boaters. Nearly every room provides breathtaking views of the water and swaying palms. Constructed with concrete block on both floors and

Cliff Glansen FLATFEE.COM

135 Tina Island Dr, Osprey, FL 34229
/2
$85,000 Sold May 23, 2025
- 959 Sq Ft
- $89/SF
- 87 Days On Market
- 2 Beds
- 2 Baths
- Built 1978
199 Palm Air Dr, Osprey, FL 34229

MOTIVATED SELLER, BRING ALL OFFERS!!! Handyman special in a great location, the recent hurricane damaged the carport, shed, and Florida room. Priced for plenty of equity after repairs are made. The highly sought-after Arbors Mobile Home Park in Osprey is where location truly matters! This mobile home offers a perfect blend of comfort and convenience. With 2 bedrooms, 2 baths, and an inviting

Allison Bollero KELLER WILLIAMS ISLAND LIFE REAL ESTATE

199 Palm Air Dr, Osprey, FL 34229

/25
Est $243,430 Not Listed For Sale
13 Bay Ave, Osprey, FL 34229

13 Bay Ave, Osprey, FL 34229

/41
$350,000
- 2 Beds
- 2 Baths
- 1,165 Sq Ft
1801 Highland Rd, Osprey, FL 34229

One or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhome in the desirable Town-End Shores community of Osprey! This beautifully maintained home features an open-concept first floor with a spacious living room, dining area, and a Florida room with sliding glass doors for added natural light. The gorgeous kitchen boasts granite countertops, perfect for cooking and

Kimberly Werla RE/MAX ALLIANCE GROUP

1801 Highland Rd, Osprey, FL 34229
/2
$665,000 Sold May 23, 2025
- 1,922 Sq Ft
- $346/SF
- 125 Days On Market
- 3 Beds
- 3 Baths
- Built 1964
123 Tina Island Dr, Osprey, FL 34229

Spectacular lot and setting for home priced under county tax appraisal. This is your opportunity to own a waterfront property in the Sorrento Shores neighborhood in Osprey. This 3 bedroom, 3 bath pool home is ready for its new owners to renovate the property with cosmetic updates to create your new dream space. This property is a great investment for you to enjoy your future activities and

Glenn Davis COLDWELL BANKER SARASOTA CENT.

123 Tina Island Dr, Osprey, FL 34229

/33
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,440 Sq Ft
155 Edgewood Dr, Osprey, FL 34229

155 Edgewood Dr, Osprey, FL 34229

/92
$925,000
- 3 Beds
- 2 Baths
- 2,216 Sq Ft
21 Bayhead Ln, Osprey, FL 34229

Looking for a home you can fall in love with? The search is over! Once you see this thoughtfully updated, impeccably maintained 3 bedroom, 2 bath home in The Oaks Preserve you will know you have found your home-sweet-home. From the moment you pull up to the pavered driveway, the care taken to maintain this property is evident. Walk past the two-car garage to the pretty, double front doors with

Steve Abbe COLDWELL BANKER REALTY

21 Bayhead Ln, Osprey, FL 34229
/2
$1,020,000 Sold May 22, 2025
- 2,909 Sq Ft
- $351/SF
- 14 Days On Market
- 3 Beds
- 3 Baths
- Built 1986
284 Lookout Point Dr, Osprey, FL 34229

Welcome to the much sought after Southbay Yacht and Racquet Club!!! You can be on vacation all year long with the private marina that has 172 boat slips that can accommodate yachts up to 55 feet. This one of a kind private marina will also accommodate personal water crafts and kayaks too!!. Our boat slip rentals are based on availability with a very attractive quarterly fee as compared to other

Carol Thompson ROYAL PALM REALTY

284 Lookout Point Dr, Osprey, FL 34229

/2
Est $1,125,298 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,573 Sq Ft
84 Bishops Court Rd, Osprey, FL 34229

84 Bishops Court Rd, Osprey, FL 34229

/2
$225,000
480 Blackburn Point Rd Unit 4, Osprey, FL 34229

A rare find in Sarasota, this covered 50 ft wet slip at Osprey Harbor Village offers the perfect blend of protection, convenience, and value. Located at 480 Blackburn Point Road in Osprey, just off the Intracoastal Waterway, this sheltered slip keeps your yacht out of the Florida sun with quick access north to Sarasota Bay or south to Venice, Midnight Pass, and no fixed bridges to the Gulf.

Daniel Treiman MICHAEL SAUNDERS & COMPANY

480 Blackburn Point Rd Unit 4, Osprey, FL 34229
/2
$835,000 Sold May 21, 2025
- 2,214 Sq Ft
- $377/SF
- 42 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2006
14021 Bellagio Way Unit 410, Osprey, FL 34229

Enjoy STUNNING sunsets 365 days a year in this LUXURIOUS WATERFRONT CONDO in Osprey, FL. From the moment you step out of your PRIVATE ELEVATOR and into this PENTHOUSE UNIT you’ll be amazed by the SPECTACULAR VIEWS overlooking Little Sarasota Bay and the Intracoastal Waterway (ICW). This 3 bed/3.5bath, TURNKEY FURNISHED unit, has been freshly painted inside and features newer flooring, crown

Adam Waxler UKEEPCOMMISSION REAL ESTATE

14021 Bellagio Way Unit 410, Osprey, FL 34229

/3
Est $217,500 Not Listed For Sale
436 Glenwood Ave, Osprey, FL 34229

436 Glenwood Ave, Osprey, FL 34229

/76
$499,900
- 2 Beds
- 2 Baths
- 1,604 Sq Ft
508 Meadow Sweet Cir, Osprey, FL 34229

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

Bill Cantrell FLORIDA HOME TEAM LLC

508 Meadow Sweet Cir, Osprey, FL 34229
/66
$155,000 Sold May 15, 2025
- 736 Sq Ft
- $211/SF
- 4 Days On Market
- 1 Bed
- 1 Bath
- Built 1973
767 Pine Run Dr, Osprey, FL 34229

Welcome to 767 Pine Run 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 736 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 to

Priscilla Adams COMPASS FLORIDA LLC

767 Pine Run Dr, Osprey, FL 34229

/37
Est $369,914 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
117 Navigation Cir Unit 101, Osprey, FL 34229

117 Navigation Cir Unit 101, Osprey, FL 34229

/50
$659,000
- 3 Beds
- 3 Baths
- 2,320 Sq Ft
522 Luminary Blvd, Osprey, FL 34229

This highly sought-after Ashley II model is situated with rear yard southern exposure on the community lake within the beautiful Willowbend neighborhood. The residence encompasses 2,320 square feet of open living space, including three bedrooms, three bathrooms, formal living and dining rooms, and an additional office or den. The kitchen is equipped with a full island, generous cabinetry,

Ray Nesci REALTY MARK ASSOCIATES

522 Luminary Blvd, Osprey, FL 34229
/69
$265,000 Sold May 15, 2025
- 1,379 Sq Ft
- $192/SF
- 74 Days On Market
- 2 Beds
- 2 Baths
- Built 1973
360 Pine Run Dr Unit 360, Osprey, FL 34229

Welcome to 360 Pine Run Drive, a stunning residence nestled in the heart of Osprey, FL. This beautifully updated 2-bedroom, 2-bathroom condo spans 1,379 square feet and is the largest of its kind in the community. Designed by the renowned architect Frank Folsom Smith, this home is a masterpiece of the Sarasota School of Architecture, offering a seamless blend of style and functionality.As you

Priscilla Adams COMPASS FLORIDA LLC

360 Pine Run Dr Unit 360, Osprey, FL 34229

/57
Est $667,494 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,630 Sq Ft
6100 Jessie Harbor Dr Unit 503, Osprey, FL 34229

6100 Jessie Harbor Dr Unit 503, Osprey, FL 34229

/6
$145,000
570 Blackburn Point Rd Unit 19, Osprey, FL 34229

Highly desirable floor-level T-Top boat rack at Osprey Harbor Village with 12 ft of height! This XL rack accommodates vessels up to 30.5L x 10W x 12H and offers quick access to Midnight Pass and Venice Inlet. Marina amenities include call-ahead splash, fuel, ice, bait and tackle, fish cleaning station, adjacent restaurant, maintenance racks, and wash-down service after each use. Monthly condo

Daniel Treiman MICHAEL SAUNDERS & COMPANY

570 Blackburn Point Rd Unit 19, Osprey, FL 34229
/2
$520,000 Sold May 14, 2025
- 1,700 Sq Ft
- $306/SF
- 7 Days On Market
- 3 Beds
- 2 Baths
- Built 2001
544 Meadow Sweet Cir, Osprey, FL 34229

Welcome to this charming 3-bedroom, 2-bathroom, maintenance-free single-family home in Osprey, Florida!Located in the unique Cottages of Rivendell Community, this neighborhood offers a warm and welcomingenvironment where neighbors become friends from day one. Under the mature trees, you can walk in the shadeeven the warmest day of the year.As you step through the beautiful double doors, you'll be

Zita Bowers MICHAEL SAUNDERS & COMPANY

544 Meadow Sweet Cir, Osprey, FL 34229

/37
Est $592,476 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,846 Sq Ft
514 Oak Bay Dr, Osprey, FL 34229

514 Oak Bay Dr, Osprey, FL 34229

/94
$245,000
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
111 Woodland Place, Osprey, FL 34229

Hidden away in Osprey is the private oasis of Pine Run. You could not find a more natural setting and fantastic location, convenient to Sarasota, Venice and Gulf beaches. This immaculate, ground floor condo is being sold furnished so settling in will be easy. The updated kitchen with stainless appliances is large enough to incorporate dine-in eating, and a laundry closet with full size washer and

Priscilla Adams COMPASS FLORIDA LLC

111 Woodland Place, Osprey, FL 34229
/55
$480,000 Sold May 14, 2025
- 1,808 Sq Ft
- $265/SF
- 57 Days On Market
- 3 Beds
- 2 Baths
- Built 2003
564 Meadow Sweet Cir, Osprey, FL 34229

Discover serenity and peace of mind in this idyllic property in the sought after Cottages of Rivendell. Close to breathtaking Casey Key, Siesta Key Beach, Nokomis Beach and the crystal blue waters of the Gulf of Mexico. This home offers an excellent location with convenient access to all modern amenities. Enjoy the luxury of being short distance to the nationally acclaimed Pine View School. The

Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

564 Meadow Sweet Cir, Osprey, FL 34229

/63
Est $1,225,719 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,048 Sq Ft
113 Harbor House Dr, Osprey, FL 34229

113 Harbor House Dr, Osprey, FL 34229

/44
$299,000
- 2 Beds
- 2 Baths
- 1,379 Sq Ft
707 Pine Run Dr, Osprey, FL 34229

Nestled in a nature enthusiast’s haven is an architecturally stunning community. Located halfway between the cultural, shopping & culinary meccas of Sarasota & Venice you find the uniquely contemporary community of Pine Run. The community offers Tennis & Pickleball courts, Fitness center, two heated pools, Saunas and an exquisite club house. This ground floor unit offers dual zone A/C, in unit

James Rightmyer RESULTS REALTY GROUP LLC

707 Pine Run Dr, Osprey, FL 34229
/2
$710,000 Sold May 09, 2025
- 2,533 Sq Ft
- $280/SF
- 117 Days On Market
- 3 Beds
- 3 Baths
- Built 2002
710 Shadow Bay Way, Osprey, FL 34229

Florida’s perfect floor plan! Built in 2002, this home features soaring ceilings, engineered hardwood maple floors that are softer and warmer underfoot than tile, and a thoughtfully designed layout for both living and entertaining. The great room, complete with a cozy wood-burning fireplace, flows seamlessly into a formal dining room, a spacious eat-in kitchen, and a versatile office. The serene

Veronica Manes MICHAEL SAUNDERS & COMPANY

710 Shadow Bay Way, Osprey, FL 34229

/18
Est $273,326 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 996 Sq Ft
248 Washington Ave, Osprey, FL 34229

248 Washington Ave, Osprey, FL 34229

/33
$177,000
- 1 Bed
- 1 Bath
- 886 Sq Ft
310 Pine Run Dr, Osprey, FL 34229

SELLER OFFERING 1 YEAR HOME WARRANTY! Seller did $20,000 of upgrades. Welcome to 310 Pine Run Dr a charming and thoughtfully designed 1-bedroom, 1-bath condominium with an additional open loft space, nestled in the serene, amenity-rich Pine Run community. This unit blends comfort and functionality with a bright, open layout, perfect for seasonal or year-round living. Have peace of mind with 2022

Krystina Londeree COMPASS FLORIDA LLC

310 Pine Run Dr, Osprey, FL 34229
/2
$780,000 Sold May 08, 2025
- 2,154 Sq Ft
- $362/SF
- 6 Days On Market
- 3 Beds
- 2 Baths
- Built 2002
779 Fordingbridge Way, Osprey, FL 34229

Discover the park like unhurried living of Rivendell, known for its tree lined streets, friendly neighbors. Residents enjoy 380 acres with 200 acres as preserves, lakes, open spaces, and trails. Fully remodeled one owner home meticulously maintained, new tile roof Jan 2025, impact glass windows all around, fully remodeled 2154 sqft in a great room design. All on a 0.46-acre private preserve view

Leonard Giarrano RE/MAX ALLIANCE GROUP

779 Fordingbridge Way, Osprey, FL 34229

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