Osprey, FL Homes

/2
Est $1,023,092

Not Listed For Sale

84 Bishops Court Rd, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,573 Sq Ft
- Built 1989
84 Bishops Court Rd, Osprey, FL 34229

Last Sold Summary
- 35 Days On Market

/36
$299,000

$20K PRICE DROP
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
4226 Frontier Ln Unit 103, Osprey, FL 34229

Coastal convenience meets effortless living, just minutes from Siesta Key, America’s #1 beach. Welcome to 4226 Frontier Lane, a beautifully maintained 2-bedroom, 2-bath walk-up condo in the gated community of Bay Street Village, offering exceptional value and an easy Florida lifestyle. Built for peace of mind with hurricane impact windows concrete-block construction. A private ground-level garage

Kate Kwiecinski COLDWELL BANKER REALTY

4226 Frontier Ln Unit 103, Osprey, FL 34229
/2
$158,000

Sold May 05, 2026

166 Edgewood Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 959 Sq Ft
- Built 1977
Last Sold Summary
- 5% Below List Price
- $165/SF
- 17 Days On Market
Last Listing Agent Karen Geiger COLDWELL BANKER SARASOTA CENT.

166 Edgewood Dr, Osprey, FL 34229

/2
Est $541,016

Not Listed For Sale

619 Pine Ranch Rd E, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,222 Sq Ft
- Built 1994
619 Pine Ranch Rd E, Osprey, FL 34229

Last Sold Summary
- 47 Days On Market

/34
$427,000

Pending
- 3 Beds
- 2 Baths
- 1,478 Sq Ft
212 Washington Ave, Osprey, FL 34229

One or more photo(s) has been virtually staged. Welcome to your private poolside retreat in the desirable coastal community of Osprey—perfectly situated on a premium corner lot with NO HOA and NO CDD fees!This beautiful 3-bedroom, 2-bath home offers a bright, open-concept layout designed forboth everyday comfort and effortless entertaining. The spacious living area features

Jeff Jones MARK SPAIN REAL ESTATE

212 Washington Ave, Osprey, FL 34229
/2
$568,792

Sold Jun 30, 2025

393 N Point Rd Unit 503, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,203 Sq Ft
- Built 2001
Last Sold Summary
- 28% Below List Price
- $258/SF
- 296 Days On Market
Current Estimated Value $561,636

Last Listing Agent Mark Lyda GENEROUS PROPERTY

393 N Point Rd Unit 503, Osprey, FL 34229

/37
Est $342,797

Not Listed For Sale

117 Navigation Cir Unit 101, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Built 2014
117 Navigation Cir Unit 101, Osprey, FL 34229

Last Sold Summary
- 35 Days On Market

/4
$1,500
- 1 Bed
- 1 Bath
- 480 Sq Ft
124 Happy Haven Dr Unit 10, 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 10, Osprey, FL 34229
/2
$169,000

Sold Jan 09, 2026

218 Palm Air Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
- Built 1979
Last Sold Summary
- 11% Below List Price
- $151/SF
- 44 Days On Market
Last Listing Agent Carlos Saramago EXIT KING REALTY

218 Palm Air Dr, Osprey, FL 34229

/57
Est $658,318

Not Listed For Sale

6100 Jessie Harbor Dr Unit 503, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,630 Sq Ft
- Built 2005
6100 Jessie Harbor Dr Unit 503, Osprey, FL 34229

Last Sold Summary
- 48 Days On Market

/100
$1,185,000
- 3 Beds
- 3 Baths
- 3,180 Sq Ft
61 Bayhead Ln, Osprey, FL 34229

Thoughtfully Built MAINTENANCE-FREE Court Yard Life Style Home in Bishops Court in the Oaks Preserve Neighborhood. This Rare Unique Home Design Features: 3 Extra Large Bedrooms, 3 Full Baths, Oversized Main Floor Master Suite w/Sitting Room and Door to Private Back Patio, plus a Wall of Sliders Looking out to the Court Yard Pool Area, Tall Ceilings, Large Walk-in Closet w/Built-ins, Brand New

Anne Thomas RE/MAX ALLIANCE GROUP

61 Bayhead Ln, Osprey, FL 34229
/2
$990,000

Sold Feb 10, 2026

820 Placid Lake Dr, Osprey, FL 34229
- 5 Beds
- 4 Baths
- 3,938 Sq Ft
- Built 2002
Last Sold Summary
- 29% Below List Price
- $251/SF
- 309 Days On Market
Current Estimated Value $977,845

Last Listing Agent Ali Marks LOYD ROBBINS & CO. LLC

820 Placid Lake Dr, Osprey, FL 34229

/13
Est $1,145,009

Not Listed For Sale

3603 N Point Rd Unit 603, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,680 Sq Ft
- Built 2007
3603 N Point Rd Unit 603, Osprey, FL 34229

Last Sold Summary
- 0 Days On Market

/95
$700,000

$200K PRICE DROP
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
401 N Point Rd Unit 304, Osprey, FL 34229

Give yourself the gift of refined living in this expansive 2,778 square foot residence—the largest non-penthouse floor plan available in Meridian at The Oaks Preserve. Every detail in this meticulously maintained, and beautifully updated condominium has been thoughtfully designed to offer comfort, sophistication, and versatility, making it the perfect sanctuary for luxury living every day! Step

Steve Abbe COLDWELL BANKER REALTY

401 N Point Rd Unit 304, Osprey, FL 34229
/2
$479,000

Sold Sep 10, 2025

26 Bay Acres Ave, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,904 Sq Ft
- Built 1971
Last Sold Summary
- $252/SF
- 6 Days On Market
Current Estimated Value $514,158

Last Listing Agent Erica Giesler COMPASS FLORIDA LLC

26 Bay Acres Ave, Osprey, FL 34229

/2
Est $1,428,760

Not Listed For Sale

639 Eagle Watch Ln, Osprey, FL 34229
- 4 Beds
- 5.5 Baths
- 3,906 Sq Ft
- Built 1989
639 Eagle Watch Ln, Osprey, FL 34229

Last Sold Summary
- 212 Days On Market

/54
$585,000

Open Fri 1PM - 3PM $30K PRICE DROP
- 4 Beds
- 3 Baths
- 2,370 Sq Ft
4424 Conchfish Ln, Osprey, FL 34229

Situated in the highly sought-after community of Palms at Casey Key, this beautifully maintained 2017-built home offers the perfect blend of comfort, style, and location. With low HOA fees and no CDD fees, this property delivers exceptional value in one of Osprey’s most desirable areas. From the moment you arrive, the paver driveway and lush tropical landscaping create a warm and welcoming first

Ashley Wallace COLDWELL BANKER REALTY

4424 Conchfish Ln, Osprey, FL 34229
/2
$492,500

Sold May 13, 2026

437 S Shore Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,947 Sq Ft
- Built 1976
Last Sold Summary
- 6% Below List Price
- $253/SF
- 15 Days On Market
Current Estimated Value $524,470

Last Listing Agent Dawn Barnett EXIT KING REALTY

437 S Shore Dr, Osprey, FL 34229

/25
Est $548,240

Not Listed For Sale

543 Meadow Sweet Cir, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,981 Sq Ft
- Built 2001
543 Meadow Sweet Cir, Osprey, FL 34229

Last Sold Summary
- 52 Days On Market

/97
$2,650,000

Pending
- 4 Beds
- 3.5 Baths
- 5,287 Sq Ft
449 Webbs Cove, Osprey, FL 34229

A custom-built Baron estate of timeless elegance, overlooking a tranquil lake from a quiet cul-de-sac within one of the region’s most coveted guard-gated communities. Located in Oaks Bayside, oak-canopied streets, private bay access, and a peaceful setting define everyday living—just steps from the community’s private day dock on Little Sarasota Bay for kayaking and sunset views.Offering

Rosalie Phillips MICHAEL SAUNDERS & COMPANY

449 Webbs Cove, Osprey, FL 34229
/2
$625,000

Sold Nov 07, 2025

594 Pine Ranch Rd E, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,298 Sq Ft
- Built 1997
Last Sold Summary
- 4% Below List Price
- $272/SF
- 51 Days On Market
Current Estimated Value $615,079

Last Listing Agent Dan Henson DALTON WADE INC

594 Pine Ranch Rd E, Osprey, FL 34229

/64
Est $245,126

Not Listed For Sale

224 Woodland Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,325 Sq Ft
- Built 1980
224 Woodland Dr, Osprey, FL 34229

Last Sold Summary
- 133 Days On Market

/26
$1,500,000

Pending
- Land
- 28,749 Sq Ft
- $2,272,727 per Acre
893 MacEwen Dr, Osprey, FL 34229

Under contract-accepting backup offers. Exceptional opportunity to secure a rarely available 0.66-acre vacant lot in the esteemed Oaks Country Club community. Bring your vision to life and build a custom luxury estate with renowned builder Henson Construction. Surrounded by stunning natural beauty and upscale amenities, this prime homesite offers the ideal setting for refined country club living.

Mark Lyda GENEROUS PROPERTY

893 MacEwen Dr, Osprey, FL 34229
/2
$160,000

Sold Mar 03, 2026

216 Palm Air Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,055 Sq Ft
- Built 1983
Last Sold Summary
- 2% Below List Price
- $152/SF
- 71 Days On Market
Last Listing Agent Todd Goodman KELLER WILLIAMS ON THE WATER S

216 Palm Air Dr, Osprey, FL 34229

/59
Est $1,174,587

Not Listed For Sale

384 S Creek Ct, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 3,811 Sq Ft
- Built 1982
384 S Creek Ct, Osprey, FL 34229

Last Sold Summary
- 71 Days On Market

/11
$649,000

$80K PRICE DROP
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
110 Pine Ave, Osprey, FL 34229

Heart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your RV and all your toys. Lots of room for storage. Enjoy sunsets, steps to fishing pier, kayak launch, Spanish Pointe, Oscar Scherer State Park, and Pine View School. No restrictions. Move-in ready enjoying the Florida lifestyle! For outdoor enthusiasts, this location is unbeatable. Launch your kayak or

Marisa Marino BRIGHT REALTY

110 Pine Ave, Osprey, FL 34229
/2
$745,000

Sold Jan 16, 2026

640 Crane Prairie Way, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,534 Sq Ft
- Built 2005
Last Sold Summary
- 3% Below List Price
- $294/SF
- 23 Days On Market
Current Estimated Value $746,722

Last Listing Agent Jay Mitchell COLDWELL BANKER REALTY

640 Crane Prairie Way, Osprey, FL 34229

/99
Est $657,353

Not Listed For Sale

801 Oak Briar Ln, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,330 Sq Ft
- Built 2004
801 Oak Briar Ln, Osprey, FL 34229

Last Sold Summary
- 6 Days On Market

/47
$550,000

$100K PRICE DROP Pending
- 4 Beds
- 3 Baths
- 2,557 Sq Ft
104 Park Trace Blvd, Osprey, FL 34229

Under contract-accepting backup offers. Welcome to this elegant and spacious luxury pool home offering over 2,500 square feet of refined living in one of the most desirable communities along the Gulf Coast. With a freshly painted exterior, stunning hardwood floors throughout, and an exceptional layout designed for both comfort and style, this residence is move-in ready and perfectly suited for

Lisa Morreale PREMIER SOTHEBY'S INTERNATIONAL REALTY

104 Park Trace Blvd, Osprey, FL 34229
/2
$95,000

Sold Apr 30, 2026

570 Blackburn Point Rd Unit 35, Osprey, FL 34229
Last Sold Summary
- 4% Below List Price
- 17 Days On Market
Last Listing Agent David Babel BRIGHT REALTY

570 Blackburn Point Rd Unit 35, Osprey, FL 34229

/57
Est $645,429

Not Listed For Sale

6100 Jessie Harbor Dr Unit 201, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,630 Sq Ft
- Built 2005
6100 Jessie Harbor Dr Unit 201, Osprey, FL 34229

Last Sold Summary
- 222 Days On Market

/47
$1,295,000

$5K PRICE DROP
- 3 Beds
- 2 Baths
- 2,850 Sq Ft
17 Bayhead Ln, Osprey, FL 34229

Impeccable is the only way to describe this charming, completely remodeled 3-bedroom, 2-bath residence that blends luxury with everyday comfort. No detail was overlooked in the renovation, resulting in a truly beautiful and thoughtfully designed home. The interior showcases high-end finishes throughout, including wood-look tile flooring, quartzite countertops, a stylish coffee bar, and a custom

Steve Abbe COLDWELL BANKER REALTY

17 Bayhead Ln, Osprey, FL 34229
/2
$215,000

Sold Nov 12, 2025

158 Edgewood Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,480 Sq Ft
- Built 2014
Last Sold Summary
- 9% Below List Price
- $145/SF
- 12 Days On Market
Last Listing Agent Renee Marquiss NEXTHOME IN THE SUN

158 Edgewood Dr, Osprey, FL 34229

/2
Est $749,717

Not Listed For Sale

401 N Point Rd Unit 401, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
- Built 2003
401 N Point Rd Unit 401, Osprey, FL 34229

Last Sold Summary
- 17 Days On Market

/45
$259,000

Open Sat 12PM - 3PM $10K PRICE DROP
- 2 Beds
- 2 Baths
- 1,379 Sq Ft
754 Pine Run Dr Unit 754, Osprey, FL 34229

Virtually Staged. Rarely available and truly one-of-a-kind, this beautifully updated ground-floor 2-bedroom, 2-bath residence offers an exceptional combination of privacy, architectural character, and an unbeatable location. Designed around a stunning private open-air atrium, the home features 8-foot glass doors on three sides, flooding the interior with natural light and creating a seamless

Sasha Volosevych CALL IT CLOSED INTL REALTY

754 Pine Run Dr Unit 754, Osprey, FL 34229
/2
$730,000

Sold May 13, 2026

1019 Scherer Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,498 Sq Ft
- Built 2004
Last Sold Summary
- 1% Below List Price
- $292/SF
- 10 Days On Market
Current Estimated Value $731,837

Last Listing Agent Christine Appice CENTURY 21 SCHMIDT REAL ESTATE

1019 Scherer Way, Osprey, FL 34229

/96
Est $979,934

Not Listed For Sale

385 N Point Rd Unit 501, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
- Built 2000
385 N Point Rd Unit 501, Osprey, FL 34229

Last Sold Summary
- 0 Days On Market

/37
$195,000
- 2 Beds
- 2 Baths
- 1,199 Sq Ft
320 Tropic Dr, Osprey, FL 34229

One or more photo(s) has been virtually staged. Welcome to this Partially Furnished home in the desirable 55+ cooperative community of The Arbors!This property in The Arbors stands out primarily for its rare inclusion of a separate adjacent lot, providing significant flexibility for either added privacy or future expansion. This is a very special property as it includes a second lot with an

Susan Retzke RE/MAX PALM

320 Tropic Dr, Osprey, FL 34229
/2
$4,700,000

Sold Jun 17, 2026

730 Sarabay Rd, Osprey, FL 34229
- 4 Beds
- 5.5 Baths
- 6,308 Sq Ft
- Built 2011
Last Sold Summary
- 14% Below List Price
- $745/SF
- 174 Days On Market
Current Estimated Value $4,899,586

Last Listing Agent Debbie Baraona ROBERT SLACK LLC

730 Sarabay Rd, Osprey, FL 34229

/73
Est $388,831

Not Listed For Sale

291 Hidden Bay Dr Unit 201, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,599 Sq Ft
- Built 2000
291 Hidden Bay Dr Unit 201, Osprey, FL 34229

Last Sold Summary
- 7 Days On Market

Showing Results 201 - 240, Page 6 of 18

Florida Sarasota County Osprey

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Osprey, FL Homes

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