Osprey, FL Homes

/2
Est $523,553

Not Listed For Sale

502 Oak Bay Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,116 Sq Ft
- Built 1995
502 Oak Bay Dr, Osprey, FL 34229

Last Sold Summary
- 88 Days On Market

/48
$599,000

$86K PRICE DROP
- 3 Beds
- 3 Baths
- 2,055 Sq Ft
409 N Point Rd Unit 502, Osprey, FL 34229

**GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The coveted lifestyle of The Oaks Country Club with the convenience and amenities of maintenance-free condominium living come together at this Gorgeous Meridian 5th floor residence. Upon exiting the elevator into the private foyer, step inside and enjoy the breathtaking panoramic preserve, bay and Gulf of Mexico

Mark Lyda GENEROUS PROPERTY

409 N Point Rd Unit 502, Osprey, FL 34229
/2
$2,625,000

Sold Sep 16, 2025

478 Oriskany Ct, Osprey, FL 34229
- 4 Beds
- 7 Baths
- 5,778 Sq Ft
- Built 1999
Last Sold Summary
- 12% Below List Price
- $454/SF
- 10 Days On Market
Current Estimated Value $2,584,523

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

478 Oriskany Ct, Osprey, FL 34229

/65
Est $998,786

Not Listed For Sale

800 Eaglenook Way, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,632 Sq Ft
- Built 1978
800 Eaglenook Way, Osprey, FL 34229

Last Sold Summary
- 2 Days On Market

/3
$34,900
- 1 Bed
- 1 Bath
- 418 Sq Ft
124 Happy Haven Dr Unit 56, Osprey, FL 34229

Happy Haven, a professionally managed, well-maintained manufactured home community, currently has a 418 sq. ft. home with 1 bedrooms and 1 bathrooms for sale. Take advantage of this offer now and live in one of the state's most attractive areas. Call and schedule a viewing of this home and ask about our current promotions!

Tori Coil Happy Haven

124 Happy Haven Dr Unit 56, Osprey, FL 34229
/2
$1,325,000

Sold Nov 07, 2025

402 Walls Way, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 3,464 Sq Ft
- Built 2014
Last Sold Summary
- 22% Below List Price
- $383/SF
- 187 Days On Market
Current Estimated Value $1,454,248

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

402 Walls Way, Osprey, FL 34229

/2
Est $912,124

Not Listed For Sale

128 Sea Anchor Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,677 Sq Ft
- Built 1978
128 Sea Anchor Dr, Osprey, FL 34229

Last Sold Summary
- 4 Days On Market

/7
$3,000
- 1 Bed
- 1 Bath
- 310 Sq Ft
124 Happy Haven Dr Unit 28, Osprey, FL 34229

Calling all Investors! Huge opportunity to make a deal on this perfect renovation project. Quick Closing, Quick Renovation and Quick Profit! This home needs significant work and is priced accordingly. Given the amount of work necessary to bring this gem up to it's fiull potential, prospective investors must be licensed and experienced renovation specialists. Call today, we are currently

Tori Coil Happy Haven

124 Happy Haven Dr Unit 28, Osprey, FL 34229
/2
$260,000

Sold May 13, 2026

135 Woodland Place, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
- Built 1979
Last Sold Summary
- 3% Below List Price
- $198/SF
- 13 Days On Market
Current Estimated Value $266,383

Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

135 Woodland Place, Osprey, FL 34229

/2
Est $355,478

Not Listed For Sale

294 Hidden Bay Dr Unit 103, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,568 Sq Ft
- Built 2001
294 Hidden Bay Dr Unit 103, Osprey, FL 34229

Last Sold Summary
- 166 Days On Market

/73
$875,000

Pending
- 3 Beds
- 2 Baths
- 1,859 Sq Ft
157 Lookout Point Dr, Osprey, FL 34229

Under contract-accepting backup offers. This one is an impressive little gem located in sought after Southbay Yacht & Racquet Club. So many improvements, upgrades and updates all you need to do is bring your furniture and move right in. As we approach the hurricane season, you will enjoy the sense of security provided by the replacement of all windows, sliders and doors with hurricane impact

Pat Williams PAT WILLIAMS REALTY, LLC

157 Lookout Point Dr, Osprey, FL 34229
/2
$625,000

Sold Oct 10, 2025

644 Rivendell Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,298 Sq Ft
- Built 2001
Last Sold Summary
- 16% Below List Price
- $272/SF
- 260 Days On Market
Current Estimated Value $627,985

Last Listing Agent Veronica Manes MICHAEL SAUNDERS & COMPANY

644 Rivendell Blvd, Osprey, FL 34229

/9
Est $186,133

Not Listed For Sale

242 Washington Ave, Osprey, FL 34229
- 2 Beds
- 1 Bath
- 630 Sq Ft
- Built 1950
242 Washington Ave, Osprey, FL 34229

Last Sold Summary
- 162 Days On Market

/38
$899,995
- 3 Beds
- 2.5 Baths
- 2,199 Sq Ft
14021 Bellagio Way Unit 309, Osprey, FL 34229

Enjoy breathtaking sunset views overlooking the intercostal waterway in this boater's paradise, complete with an on-site marina. Discover coastal living in this beautifully updated 3-bedroom, 2.5-bath residence located in Bellagio Harbor Village. Ideally positioned between Sarasota Big Pass and the Venice Jetty, and just minutes from Midnight Pass and the Gulf of Mexico, this home offers easy

Tristin Hopler COMPASS FLORIDA, LLC

14021 Bellagio Way Unit 309, Osprey, FL 34229
/2
$675,000

Sold Jan 21, 2026

409 N Point Rd Unit 501, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
- Built 2004
Last Sold Summary
- 36% Below List Price
- $260/SF
- 575 Days On Market
Current Estimated Value $687,720

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

409 N Point Rd Unit 501, Osprey, FL 34229

/2
Est $638,512

Not Listed For Sale

385 N Point Rd Unit 602, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,055 Sq Ft
- Built 2000
385 N Point Rd Unit 602, Osprey, FL 34229

Last Sold Summary
- 174 Days On Market

/54
$880,000
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
401 N Point Rd Unit 504, Osprey, FL 34229

INCREDIBLE OPPORTUNITY AND A MUST SEE AT THE MERIDIAN AT THE OAKS - GREAT PRICE, BAY VIEW, UPDATED KITCHEN, PRIVATE 2 CAR GARAGE AND MORE! Beautifully updated and thoughtfully designed, this exceptional 5th floor residence in The Meridian at The Oaks Preserve offers tranquil water and preserve views, a fantastic floor plan, and the rare convenience of a private 2-car garage just steps to the

Lenore Treiman MICHAEL SAUNDERS & COMPANY

401 N Point Rd Unit 504, Osprey, FL 34229
/2
$375,000

Sold Jun 18, 2026

1795 Highland Rd, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 1,879 Sq Ft
- Built 1999
Last Sold Summary
- $200/SF
- 24 Days On Market
Current Estimated Value $378,877

Last Listing Agent Rachel Tritschler RE/MAX ALLIANCE GROUP

1795 Highland Rd, Osprey, FL 34229

/2
Est $516,045

Not Listed For Sale

515 Oak Bay Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,977 Sq Ft
- Built 1995
515 Oak Bay Dr, Osprey, FL 34229

Last Sold Summary
- 116 Days On Market

/41
$700,000

$19K PRICE DROP
- 2 Beds
- 2 Baths
- 1,932 Sq Ft
242 Hidden Bay Dr Unit 602, Osprey, FL 34229

Penthouse Waterfront Residence | Enclosed Sunroom | Private Two-Car Garage | Optional Furnishings | Gated Bayfront Community This 6th-floor penthouse waterfront condominium at Hidden Bay offers unobstructed views of Little Sarasota Bay, the Intracoastal Waterway, and the Gulf beyond Casey Key. Designed to capture light and water views throughout the main living areas, the open floor plan features

Cathy Rustin FIRST LIGHT REAL ESTATE

242 Hidden Bay Dr Unit 602, Osprey, FL 34229
/2
$3,650,000

Sold Apr 06, 2026

691 Eagle Watch Ln, Osprey, FL 34229
- 4 Beds
- 7 Baths
- 6,705 Sq Ft
- Built 1993
Last Sold Summary
- 9% Below List Price
- $544/SF
- 78 Days On Market
Current Estimated Value $3,580,483

Last Listing Agent Renee Preininger SARASOTA TRUST REALTY COMPANY

691 Eagle Watch Ln, Osprey, FL 34229

/2
Est $383,341

Not Listed For Sale

109 Burney Rd, Osprey, FL 34229
- 2 Beds
- Built 1959
109 Burney Rd, Osprey, FL 34229

Last Sold Summary
- 30 Days On Market

/2
$643,749

New Construction
- 3 Beds
- 2 Baths
- 1,356 Sq Ft
791 S Tamiami Trail Unit 303, Osprey, FL 34229

Under Construction. UNDER CONSTRUCTION-STARTING FROM THE MID $500,000'S. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOW AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 3 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (2 BEDROOM AND 2 BATH UNITS ALSO

Laurie Eshleman PRO GROUP REALTY & PROP MGT

791 S Tamiami Trail Unit 303, Osprey, FL 34229
/2
$318,000

Sold Mar 25, 2026

116 Navigation Cir Unit 106, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,430 Sq Ft
- Built 2016
Last Sold Summary
- 2% Below List Price
- $222/SF
- 220 Days On Market
Current Estimated Value $317,455

Last Listing Agent Pan Steele, GRI COLDWELL BANKER REALTY

116 Navigation Cir Unit 106, Osprey, FL 34229

/2
Est $190,503

Not Listed For Sale

235 Woodland Dr Unit 235, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,223 Sq Ft
- Built 1980
235 Woodland Dr Unit 235, Osprey, FL 34229

Last Sold Summary
- 53 Days On Market

/2
$514,999

New Construction
- 2 Beds
- 2 Baths
- 952 Sq Ft
791 S Tamiami Trail Unit 202, Osprey, FL 34229

Under Construction. UNDER CONSTRUCTION STARTING FROM THE UPPER $400,000. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOWN AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 2 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (3 BEDROOM AND 2 BATH UNITS ALSO

Laurie Eshleman PRO GROUP REALTY & PROP MGT

791 S Tamiami Trail Unit 202, Osprey, FL 34229
/2
$1,900,000

Sold Feb 10, 2026

340 Osprey Point Dr, Osprey, FL 34229
- 5 Beds
- 7 Baths
- 6,001 Sq Ft
- Built 1998
Last Sold Summary
- 24% Below List Price
- $317/SF
- 273 Days On Market
Current Estimated Value $1,952,250

Last Listing Agent Lee Brewer RE/MAX ALLIANCE GROUP

340 Osprey Point Dr, Osprey, FL 34229

/34
Est $563,512

Not Listed For Sale

1358 Thornapple Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,163 Sq Ft
- Built 2003
1358 Thornapple Dr, Osprey, FL 34229

Last Sold Summary
- 86 Days On Market

/69
$679,000

$19K PRICE DROP
- 2 Beds
- 2.5 Baths
- 1,890 Sq Ft
33 Bishops Court Rd Unit 118, Osprey, FL 34229

**EXPERIENCE EFFORTLESS LIVING in this BEAUTIFULLY UPDATED TOWNHOUSE with SERENE WATER VIEWS** Located behind the Secure Gates of The Oaks Preserve, Golf & Country Club neighborhood, this delightful residence features 2 En Suite Bedrooms on the 2nd Floor, 2 Full and 1 Half Baths, and offers a refined yet relaxed lifestyle surrounded by mature oak canopies and tranquil lake views. The main living

Mark Lyda GENEROUS PROPERTY

33 Bishops Court Rd Unit 118, Osprey, FL 34229
/2
$550,000

Sold Feb 19, 2026

494 Meadow Sweet Cir, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,791 Sq Ft
- Built 1997
Last Sold Summary
- 8% Below List Price
- $307/SF
- 7 Days On Market
Current Estimated Value $556,113

Last Listing Agent Carlos Saramago EXIT KING REALTY

494 Meadow Sweet Cir, Osprey, FL 34229

/42
Est $558,294

Not Listed For Sale

564 Crane Prairie Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,079 Sq Ft
- Built 2005
564 Crane Prairie Way, Osprey, FL 34229

Last Sold Summary
- 69 Days On Market

/71
$275,000
- 1 Bed
- 1 Bath
- 623 Sq Ft
51 MacEwen Dr Unit 12, Osprey, FL 34229

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

Steve Abbe COLDWELL BANKER REALTY

51 MacEwen Dr Unit 12, Osprey, FL 34229
/2
$520,000

Sold Dec 30, 2025

447 Oak Point Rd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,688 Sq Ft
- Built 1994
Last Sold Summary
- 5% Below List Price
- $193/SF
- 49 Days On Market
Current Estimated Value $514,636

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

447 Oak Point Rd, Osprey, FL 34229

/3
Est $636,541

Not Listed For Sale

6100 Jessie Harbor Dr Unit 403, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,630 Sq Ft
- Built 2005
6100 Jessie Harbor Dr Unit 403, Osprey, FL 34229

Last Sold Summary
- 108 Days On Market

/70
$694,000

$5K PRICE DROP
- 2 Beds
- 2.5 Baths
- 1,950 Sq Ft
260 Hidden Bay Dr Unit B-304, Osprey, FL 34229

The Boca Residence: Spacious Living & Resort StyleDiscover a condominium that offers the true scale and functionality of a private home. The Boca floor plan features a thoughtfully designed two-bedroom plus den, two-and-a-half-bathroom layout, perfect for those who want the ease of condo living without sacrificing space. Whether you are looking for a full-time residence or a spacious seasonal

Janice Martin ENGEL & VOELKERS VENICE DOWNTOWN

260 Hidden Bay Dr Unit B-304, Osprey, FL 34229
/2
$155,000

Sold Feb 24, 2026

300 Tropic Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,031 Sq Ft
- Built 1986
Last Sold Summary
- 3% Below List Price
- $150/SF
- 54 Days On Market
Last Listing Agent Heidi Lionetti WHITE SANDS REALTY GROUP FL

300 Tropic Dr, Osprey, FL 34229

/42
Est $878,620

Not Listed For Sale

172 Sea Anchor Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,283 Sq Ft
- Built 1977
172 Sea Anchor Dr, Osprey, FL 34229

Last Sold Summary
- 61 Days On Market

/52
$1,165,000

$34K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,830 Sq Ft
1527 Buoy Ln, Osprey, FL 34229

Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilings. 2026 AC unit, 2024 tile roof, 2023 driveway, cabinets, lighting, appliances, tile and carpet are just the beginning. 2023 pool and spa led lighting, Pentair controller, saltwater conversion, and owned 250 gallon propane. Dry bar with ice maker, wine fridge, and beverage

Matthew Lewis BRIGHT REALTY

1527 Buoy Ln, Osprey, FL 34229
/2
$1,001,000

Sold Apr 27, 2026

3936 Waypoint Ave, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,323 Sq Ft
- Built 2016
Last Sold Summary
- 4% Below List Price
- $431/SF
- 3 Days On Market
Current Estimated Value $1,019,400

Last Listing Agent Larry Brzostek RE/MAX ALLIANCE GROUP

3936 Waypoint Ave, Osprey, FL 34229

/85
Est $936,048

Not Listed For Sale

184 Park Trace Blvd, Osprey, FL 34229
- 5 Beds
- 4.5 Baths
- 3,420 Sq Ft
- Built 2003
184 Park Trace Blvd, Osprey, FL 34229

Last Sold Summary
- 52 Days On Market

Showing Results 441 - 480, Page 12 of 18

Florida Sarasota County Osprey

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