Homes in ZIP Code 34229

/88
$2,700,000

$200K PRICE DROP
- 6 Beds
- 6.5 Baths
- 6,246 Sq Ft
236 Saint James Park, Osprey, FL 34229

Multigenerational living behind the gates of The Oaks Golf & Country Club. Set on a rare double lot at the end of a quiet cul-de-sac, this exceptional home is perfectly positioned on the 1st hole of the Heron Course, capturing sweeping golf course and clubhouse views—just minutes from Siesta Beach and Casey Key. The main residence offers 4,700+ square feet, complemented by a private 1,500+ square

Karin Watt MICHAEL SAUNDERS & COMPANY

236 Saint James Park, Osprey, FL 34229
/2
$715,000

Sold Mar 17, 2026

319 Park Trace Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,551 Sq Ft
- Built 2000
Last Sold Summary
- 5% Below List Price
- $280/SF
- 33 Days On Market
Current Estimated Value $724,631

Last Listing Agent Megan George PREMIER SOTHEBYS INTL REALTY

319 Park Trace Blvd, Osprey, FL 34229

/2
Est $702,866

Not Listed For Sale

1192 Mallard Marsh Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,695 Sq Ft
- Built 2002
1192 Mallard Marsh Dr, Osprey, FL 34229

Last Sold Summary
- 191 Days On Market
Last Listing Agent Marie Fogarty M H FOGARTY AND COMPANY LLC

/50
$285,000

$100K PRICE INCREASE Pending
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
108 Woodland Place Unit 108, Osprey, FL 34229

Bring your furniture and move right in to this popular Pine Run neighborhood. No need to worry about remodeling this condo! New coastal look ceramic tile throughout the entire home! New kitchen and appliances, new guest bathroom, new doors throughout, new light fixtures, and newly painted. Wow! First floor condo offers more outdoor living space. The patio off the main entry offers privacy and has

Pat Williams PAT WILLIAMS REALTY, LLC

108 Woodland Place Unit 108, Osprey, FL 34229
/2
$362,500

Sold Feb 23, 2026

291 Hidden Bay Dr Unit 101, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,599 Sq Ft
- Built 2000
Last Sold Summary
- 9% Below List Price
- $227/SF
- 58 Days On Market
Current Estimated Value $364,138

Last Listing Agent Stephanie Ham PARADISE EXCLUSIVE REAL ESTATE

291 Hidden Bay Dr Unit 101, Osprey, FL 34229

/2
Est $563,564

Not Listed For Sale

685 Clear Creek Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,204 Sq Ft
- Built 2002
685 Clear Creek Dr, Osprey, FL 34229

Last Sold Summary
- 10 Days On Market
Last Listing Agent Brian ODonnell,PLLC REALTY BY DESIGN LLC

/31
$695,000
- Land
- 25,700 Sq Ft
- $1,177,966 per Acre
216 Osprey Point Dr, Osprey, FL 34229

One of the last remaining opportunities to build a custom luxury estate in The Oaks Bayside, one of Sarasota’s distinguished private country club communities. Behind 24-hour staffed gates, this generous 25,735-square-foot homesite offers a rare chance to create a custom residence with the builder of your choice in a serene, established setting known for its stately oaks, winding streets, natural

Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

216 Osprey Point Dr, Osprey, FL 34229
/2
$2,300,000

Sold Apr 06, 2026

896 MacEwen Dr, Osprey, FL 34229
- 4 Beds
- 5.5 Baths
- 4,858 Sq Ft
- Built 1998
Last Sold Summary
- 6% Below List Price
- $473/SF
- 35 Days On Market
Current Estimated Value $2,277,620

Last Listing Agent Marisa Marino BRIGHT REALTY

896 MacEwen Dr, Osprey, FL 34229

/2
Est $886,357

Not Listed For Sale

1200 Mallard Marsh Dr, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,928 Sq Ft
- Built 2002
1200 Mallard Marsh Dr, Osprey, FL 34229

Last Sold Summary
- 118 Days On Market
Last Listing Agent Sharon Osborne, PA COLDWELL BANKER SARASOTA CENT.

/47
$3,295,000
- 3 Beds
- 4.5 Baths
- 2,572 Sq Ft
135 Tina Island Dr, Osprey, FL 34229

**EXCEPTIONAL WATERFRONT RESIDENCE with 210 ft CANAL FRONTAGE** in desirable Sorrento Shores, offering Deep Water access with No Bridges to the Bay/Gulf. Privately situated on a quiet cul-de-sac, the property enjoys tranquil water and palm views from nearly every room, with canals often visited by manatees and dolphins. Originally built in 1965, then Demolished and Re-Built in 2011 with solid

Mark Lyda GENEROUS PROPERTY

135 Tina Island Dr, Osprey, FL 34229
/2
$665,000

Sold Nov 06, 2025

563 Pine Ranch Rd E, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,346 Sq Ft
- Built 1997
Last Sold Summary
- 1% Below List Price
- $283/SF
- 5 Days On Market
Current Estimated Value $672,345

Last Listing Agent Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

563 Pine Ranch Rd E, Osprey, FL 34229

/2
Est $807,043

Not Listed For Sale

1030 Scherer Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,433 Sq Ft
- Built 2003
1030 Scherer Way, Osprey, FL 34229

Last Sold Summary
- 10 Days On Market
Last Listing Agent Kimberly Young BERKSHIRE HATHAWAY HOMESERVICE

/51
$700,000

$27K PRICE DROP
- 4 Beds
- 3.5 Baths
- 2,950 Sq Ft
759 Fordingbridge Way, Osprey, FL 34229

Discover this stunning home located in the heart of Osprey, FL. Featuring a spacious layout, this residence boasts elegant finishes and ample natural light throughout. The modern kitchen is equipped with top-of-the-line appliances and give plenty of storage space. Enjoy the serene outdoor area with a beautifully landscaped yard, appropriate for relaxation and entertainment. Situated in a

Steven Koleno BEYCOME OF FLORIDA LLC

759 Fordingbridge Way, Osprey, FL 34229
/2
$1,500,000

Sold Sep 19, 2025

462 E MacEwen Dr, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,611 Sq Ft
- Built 1998
Last Sold Summary
- 3% Below List Price
- $574/SF
- 29 Days On Market
Current Estimated Value $1,470,447

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

462 E MacEwen Dr, Osprey, FL 34229

/2
Est $653,155

Not Listed For Sale

1109 Scherer Way, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,125 Sq Ft
- Built 2002
1109 Scherer Way, Osprey, FL 34229

Last Sold Summary
- 61 Days On Market
Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

/83
$798,000

$52K PRICE DROP
- 3 Beds
- 3.5 Baths
- 3,771 Sq Ft
6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229

One or more photo(s) has been virtually staged. PRICE IMPROVED OVER $50K!!!! Experience elevated coastal living in this beautifully appointed waterfront residence, ideally located within the sought-after Blackburn Harbor community in Sarasota County.Situated on the second floor (building with elevator), this elegant and spacious 3BR + den / 3BA condominium offers over 3,700 SF of a harmonious

Angelic Tassos CORCORAN DWELLINGS REALTY

6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229
/2
$166,000

Sold May 21, 2026

238 Palm Air Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
- Built 1986
Last Sold Summary
- 8% Below List Price
- $144/SF
- 15 Days On Market
Last Listing Agent Susan Retzke RE/MAX PALM

238 Palm Air Dr, Osprey, FL 34229

/2
Est $277,297

Not Listed For Sale

234 Patterson Ave, Osprey, FL 34229
- 3 Beds
- 1 Bath
- 1,173 Sq Ft
- Built 1979
234 Patterson Ave, Osprey, FL 34229

Last Sold Summary
- 9 Days On Market
Last Listing Agent Sean Seward KELLER WILLIAMS ISLAND LIFE REAL ESTATE

/16
$1,350,000

$50K PRICE DROP
- Land
- 2.51 Acres
- $537,849 per Acre
2099 S Tamiami Trail, Osprey, FL 34229

NEW PRICE! Location! Location! This 2.51 Acre Lot is available for sale directly on South Tamiami Trail in Osprey - where Sarasota is growing and expanding! This property is zoned OPI and would be a good fit for a dental, veterinary, medical center or business offices with potential residential above. Great exposure with consistently heavy traffic from Sarasota to Naples on S. Tamiami Trail just

Susan Repp COLDWELL BANKER REALTY

2099 S Tamiami Trail, Osprey, FL 34229
/66
$654,000

Sold Apr 16, 2026

1303 Thornapple Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,929 Sq Ft
- Built 2003
Last Sold Summary
- 6% Below List Price
- $339/SF
- 93 Days On Market
Current Estimated Value $640,828

Last Listing Agent Michael A Martino KELLER WILLIAMS ON THE WATER S

1303 Thornapple Dr, Osprey, FL 34229

/2
Est $565,169

Not Listed For Sale

825 Oak Pond Dr, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,229 Sq Ft
- Built 1996
825 Oak Pond Dr, Osprey, FL 34229

Last Sold Summary
- 25 Days On Market
Last Listing Agent Magda Cetta Whelton DOUGLAS ELLIMAN

/91
$459,900

$215K PRICE DROP
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
401 N Point Rd Unit 301, Osprey, FL 34229

Virtually Staged. Short Sale. Enter through the secure foyer and take the private elevator to the third floor where you will find this charming 3 bedroom, 3 bath residence. Situated at treetop level, overlooking the preserve and surrounding lush foliage, the interior is open and neutral, with lots of natural light. This unit is waiting for you to come and put your decorating touches on it and

Steve Abbe COLDWELL BANKER REALTY

401 N Point Rd Unit 301, Osprey, FL 34229
/2
$241,000

Sold May 28, 2026

0 Sarabay Rd, Osprey, FL 34229
- Land
- 13,939 Sq Ft
- $753,125 per Acre
Last Sold Summary
- 7% Above List Price
- 3 Days On Market
Last Listing Agent Cheri Castro MICHAEL SAUNDERS & COMPANY

0 Sarabay Rd, Osprey, FL 34229

/48
Est $590,891

Not Listed For Sale

522 Meadow Sweet Cir, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 2,424 Sq Ft
- Built 1998
522 Meadow Sweet Cir, Osprey, FL 34229

Last Sold Summary
- 145 Days On Market
Last Listing Agent Sandi Tresh RE/MAX PALM REALTY OF VENICE

/95
$525,000

$100K PRICE DROP
- 3 Beds
- 3 Baths
- 2,680 Sq Ft
3621 N Point Rd Unit 301, Osprey, FL 34229

Ready to live a stress-free luxury condo lifestyle? There is no place better to do it than this 3 bedroom, 3 bath residence in Meridian at The Oaks Preserve. Nestled among the treetops, this end unit has a split floor plan and absolutely breathtaking sunset views over the Preserve and out to Little Sarasota Bay. Natural light floods the interior, highlighting the beauty of the hand-rubbed walnut

Steve Abbe COLDWELL BANKER REALTY

3621 N Point Rd Unit 301, Osprey, FL 34229
/2
$925,000

Sold Jul 15, 2026

1602 Southbay Dr, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 2,980 Sq Ft
- Built 1986
Last Sold Summary
- 7% Below List Price
- $310/SF
- 198 Days On Market
Current Estimated Value $950,105

Last Listing Agent Thomas Kiessling COMPASS FLORIDA LLC

1602 Southbay Dr, Osprey, FL 34229

/2
Est $806,873

Not Listed For Sale

790 Shadow Bay Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,091 Sq Ft
- Built 2002
790 Shadow Bay Way, Osprey, FL 34229

Last Sold Summary
- 158 Days On Market
Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

/14
$1,150,000

Pre-Foreclosure
- 3 Beds
- 1.5 Baths
- 2,084 Sq Ft
210 Patterson Ave, Osprey, FL 34229

Huge Opportunity – Three Homes – Motivated Seller!Outstanding opportunity to acquire three homes in one transaction in a rapidly developing Osprey area. The properties are located close to the proposed Margaritaville Resort, which is expected to become a major destination in the area and has been proposed to include ferry service providing access to Siesta Key. This location is already

Troy Funk REALTY ONE GROUP MVP

210 Patterson Ave, Osprey, FL 34229
/2
$520,000

Sold Jun 17, 2026

1337 Copperwood Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,172 Sq Ft
- Built 2004
Last Sold Summary
- 13% Below List Price
- $239/SF
- 199 Days On Market
Current Estimated Value $536,729

Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

1337 Copperwood Dr, Osprey, FL 34229

/2
Est $236,081

Not Listed For Sale

225 Woodland Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
- Built 1980
225 Woodland Dr, Osprey, FL 34229

Last Sold Summary
- 103 Days On Market
Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

/58
$775,000
- 3 Beds
- 2.5 Baths
- 1,950 Sq Ft
260 Hidden Bay Dr Unit B-402, Osprey, FL 34229

Semi-furnished three-bedroom, 2.5-bath unit with elevator access. This fourth-floor residence offers beautiful panoramic intracoastal water views. Centrally between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay, a gated, 12-acre resort-style community on the water's edge of Little Sarasota Bay in Osprey. The building is designed in the architectural style of Key West.

Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

260 Hidden Bay Dr Unit B-402, Osprey, FL 34229
/2
$570,000

Sold Apr 03, 2026

51 Webb St, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,130 Sq Ft
- Built 1978
Last Sold Summary
- 5% Below List Price
- $268/SF
- 6 Days On Market
Current Estimated Value $571,136

Last Listing Agent Marina Myers FINE PROPERTIES

51 Webb St, Osprey, FL 34229

/2
Est $928,185

Not Listed For Sale

32 Bayhead Ln, Osprey, FL 34229
- 3 Beds
- 3.5 Baths
- 2,570 Sq Ft
- Built 1993
32 Bayhead Ln, Osprey, FL 34229

Last Sold Summary
- 82 Days On Market
Last Listing Agent Rosalie Phillips MICHAEL SAUNDERS & COMPANY

/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
$1,700,000

Sold Sep 18, 2025

898 MacEwen Dr, Osprey, FL 34229
- 4 Beds
- 4 Baths
- 4,132 Sq Ft
- Built 1997
Last Sold Summary
- 13% Below List Price
- $411/SF
- 0 Days On Market
Current Estimated Value $1,807,892

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

898 MacEwen Dr, Osprey, FL 34229

/48
Est $745,966

Not Listed For Sale

763 Shadow Bay Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,093 Sq Ft
- Built 1998
763 Shadow Bay Way, Osprey, FL 34229

Last Sold Summary
- 22 Days On Market
Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.

/32
$649,000

Under Contract
- 3 Beds
- 2 Baths
- 2,084 Sq Ft
586 Oak Bay Dr, Osprey, FL 34229

Under contract-accepting backup offers. Welcome to Bay Oaks Estates, where spacious living, thoughtful design, and an ideal Osprey location come together in this beautifully maintained three-bedroom, two-bath home. With an open great room floor plan, a den, a separate private office, and a rare three-car garage, this home offers space and flexibility. The heart of the home is the inviting great

Mary Jo Violett WHITE SANDS REALTY GROUP FL

586 Oak Bay Dr, Osprey, FL 34229
/2
$329,000

Sold Jan 14, 2026

85 Navigation Cir, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,430 Sq Ft
- Built 2014
Last Sold Summary
- 3% Below List Price
- $230/SF
- 8 Days On Market
Current Estimated Value $321,130

Last Listing Agent Kate Kwiecinski COLDWELL BANKER REALTY

85 Navigation Cir, Osprey, FL 34229

/69
Est $243,060

Not Listed For Sale

360 Pine Run Dr Unit 360, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,379 Sq Ft
- Built 1973
360 Pine Run Dr Unit 360, Osprey, FL 34229

Last Sold Summary
- 74 Days On Market
Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

/85
$480,000

Open House 9/26 $17K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,006 Sq Ft
2309 Jessie Harbor Dr Unit 2402, Osprey, FL 34229

West-Facing Canal Views in Gated Blackburn Harbor. This second-floor, 3-bedroom, 2.5-bath condo in Blackburn Harbor Waterfront Villas puts you directly on the canal with west-facing views that make sunsets a daily event worth watching. At 2,006 square feet, the layout is spacious and light-filled — vaulted ceilings in the living, dining, primary suite and kitchen areas, two sets of sliding glass

Christine Pope MICHAEL SAUNDERS & COMPANY

2309 Jessie Harbor Dr Unit 2402, Osprey, FL 34229

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Florida Sarasota County Osprey

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