Osprey, FL Homes

/74
$1,550,000
- 3 Beds
- 3.5 Baths
- 3,066 Sq Ft
25 Sugar Mill Dr, Osprey, FL 34229

METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESERVE VIEWS. Located in Flood Zone “X” (no flood insurance required), the home is tucked behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. The home offers 3 En Suite

Mark Lyda GENEROUS PROPERTY

25 Sugar Mill Dr, Osprey, FL 34229
/45
$4,500 Per Month
- 4 Beds
- 3 Baths
- 2,290 Sq Ft
- Annual Rental: Luxurious 4 Bedroom 3 bath POOL home in Woodlands of Rivendell! Just Blocks form P...
919 Scherer Way, Osprey, FL 34229

Perfect Family Pool Home in a Location you can't ignore. Just a few blocks from The Oaks, one of the most exclusives areas in Sarasota, this impeccable home has 4 bedrooms and 3 bathrooms, 3 car garage, with just under 2,300 square feet of living area for your quiet enjoyment or entertaining friends and family. The home offers a designer pool and spa with lake and preserve views, located in the

919 Scherer Way, Osprey, FL 34229
/2
$2,100,000 Sold Jan 30, 2026

889 MacEwen Dr, Osprey, FL 34229
- 4 Beds
- 4 Baths
- 3,235 Sq Ft
- Built 1994
Last Sold Summary
- 9% Below List Price
- $649/SF
- 41 Days On Market
Current Estimated Value $2,055,629

Last Listing Agent Mark Lyda GENEROUS PROPERTY

889 MacEwen Dr, Osprey, FL 34229

/2
Est $811,429 Not Listed For Sale

124 Tina Island Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,112 Sq Ft
- Built 1975
124 Tina Island Dr, Osprey, FL 34229

Last Sold Summary
- 1% Above List Price
- $382/SF
- 244 Days On Market
- Last Sold Price $807,000
- Apr 22, 2025
Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

/44
$999,500
- 3 Beds
- 2.5 Baths
- 2,502 Sq Ft
113 Burney Rd, Osprey, FL 34229

**DON’T WAIT TO BUILD!! NEWER, CUSTOM-BUILT HOME (2020) IS MOVE-IN READY AND PACKED WITH UPGRADES** Situated on a generous 0.52-acre lot near the end of a quiet cul-de-sac, the property offers a private backyard and NO HOA fees/restrictions. Bring Your Toys! Oversized circular driveway provides ample parking for a BOAT, RV, and additional vehicles. This Impressive Residence with 2502sf of heating

Mark Lyda GENEROUS PROPERTY

113 Burney Rd, Osprey, FL 34229
/74
$8,000 Per Month
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
- Condo for Rent
14041 Bellagio Way Unit 316, Osprey, FL 34229

AVAILABLE FOR SEASON 2027 - 2 MONTH MIN REQUIRED. MINUTES TO CASEY KEY & NOKOMIS BEACH! Welcome to BELLAGIO at Osprey Harbor Village, offering luxurious waterfront living! This turnkey direct waterfront condo has 3 beds/2 baths plus a den is the perfect place for your next Florida vacation, located in a private gated community. As you step off the elevator, you are basically outside this 3rd

Chrissie Cummings JENNETTE PROPERTIES INC

14041 Bellagio Way Unit 316, Osprey, FL 34229
/2
$1,405,000 Sold Jul 11, 2025

282 Shell Midden Ct, Osprey, FL 34229
- 3 Beds
- 4.5 Baths
- 3,699 Sq Ft
- Built 1992
Last Sold Summary
- 17% Below List Price
- $380/SF
- 128 Days On Market
Current Estimated Value $1,401,689

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

282 Shell Midden Ct, Osprey, FL 34229

/2
Est $273,910 Not Listed For Sale

153 Navigation Cir Unit 106, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Built 2014
153 Navigation Cir Unit 106, Osprey, FL 34229

Last Sold Summary
- 9% Below List Price
- $264/SF
- 150 Days On Market
- Last Sold Price $300,000
- Dec 13, 2024
Last Listing Agent Peggy Olson PREMIER SOTHEBYS INTL REALTY

/75
$1,950,000
- 4 Beds
- 5.5 Baths
- 4,346 Sq Ft
538 Dove Pointe, Osprey, FL 34229

**ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, this beautifully landscaped property offers the perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home

Mark Lyda GENEROUS PROPERTY

538 Dove Pointe, Osprey, FL 34229
/48
$5,000 Per Month
- 2 Beds
- 2.5 Baths
- 1,950 Sq Ft
- Annual Turnkey 3/3 penthouse on waterfront in Osprey
260 Hidden Bay Dr, Osprey, FL 34229

Annual Turnkey Furnished or seasonal Penthouse on the Bay! If you want mesmerizing views of intracoastal waterway, Little Sarasota Bay, Casey Key, and the Gulf of Mexico in a beautiful, comfortable and roomy penthouse, then this could be your next home. This natural light filled delight is 2 bedrooms, each with en suite bathroom, separate office with large closet and glass French doors, and

260 Hidden Bay Dr, Osprey, FL 34229
/2
$1,330,000 Sold Jan 07, 2026

401 N Point Rd Unit 901, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
- Built 2003
Last Sold Summary
- 24% Below List Price
- $513/SF
- 764 Days On Market
Current Estimated Value $1,294,963

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

401 N Point Rd Unit 901, Osprey, FL 34229

/2
Est $469,791 Not Listed For Sale

19 Westview Dr, Osprey, FL 34229
- 2 Beds
- Built 1990
19 Westview Dr, Osprey, FL 34229

Last Sold Summary
- 6% Below List Price
- $308/SF
- 114 Days On Market
- Last Sold Price $500,000
- Jul 11, 2024
Last Listing Agent Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

/52
$2,100,000
- 4 Beds
- 3.5 Baths
- 3,768 Sq Ft
448 E MacEwen Dr, Osprey, FL 34229

**IMPRESSIVE GOLF COURSE ESTATE IN THE HIGHLY SOUGHT-AFTER OAKS COUNTRY CLUB** Situated on an oversized 0.59-acre lot, this exceptional, meticulously-maintained residence features many upgrades and offers breathtaking garden and golf course views in a private, serene setting. Impressive curb appeal and beautifully manicured landscaping welcome you into a beautifully appointed home featuring 4

Mark Lyda GENEROUS PROPERTY

448 E MacEwen Dr, Osprey, FL 34229
/21
$1,695 Per Month
- 2 Beds
- 2 Baths
- 1,224 Sq Ft
- Condo for Rent
354 Pine Run Dr, Osprey, FL 34229

This is an unfurnished 2 bedroom, 2 bathroom condo located in the Pine Run community in Osprey! This upper-level unit features vaulted ceilings, a mix of hardwood and tile flooring, and a distinctive courtyard-style layout that brings the outdoors inside. The kitchen features granite countertops, maple shaker-style cabinets with glass-front uppers, stainless steel appliances, a tile backsplash,

Todd Roughton SARASOTA MANAGEMENT & LEASING

354 Pine Run Dr, Osprey, FL 34229
/2
$962,500 Sold Aug 07, 2025

742 Shadow Bay Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,321 Sq Ft
- Built 2002
Last Sold Summary
- 12% Below List Price
- $290/SF
- 115 Days On Market
Current Estimated Value $958,576

Last Listing Agent Reeny Kaney RE/MAX ALLIANCE GROUP

742 Shadow Bay Way, Osprey, FL 34229

/2
Est $298,663 Not Listed For Sale

76 Explorer Dr Unit 104, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,430 Sq Ft
- Built 2017
76 Explorer Dr Unit 104, Osprey, FL 34229

Last Sold Summary
- 8% Below List Price
- $227/SF
- 34 Days On Market
- Last Sold Price $324,000
- Mar 28, 2025
Last Listing Agent Pan Steele, GRI COLDWELL BANKER REALTY

/62
$850,000
- 2 Beds
- 2 Baths
- 2,310 Sq Ft
13 Bayhead Ln, Osprey, FL 34229

**IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent updates include a new kitchen, bathrooms, flooring, fans, a four-year-old roof, a newly pavered

Mark Lyda GENEROUS PROPERTY

13 Bayhead Ln, Osprey, FL 34229
/25
$4,500 Per Month
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
- Condo for Rent
152 Navigation Cir Unit 107, Osprey, FL 34229

BACIK ON THE MARKET HIGH SEASON NOW AVAILABLE!! Seasonal and short term rental Get out of the cold and into the sunshine in this newer 3/2 condo in the gated community of Bay Street Village in Osprey. This condo is an end unit with an open floor plan for ease of entertaining and family time. The extra windows flood the unit with natural sun light. The kitchen is a natural gathering point with

Cody Smith RENT SARASOTA

152 Navigation Cir Unit 107, Osprey, FL 34229
/2
$210,000 Sold Oct 22, 2025

480 Blackburn Point Rd Unit 4, Osprey, FL 34229
- Built 2006
Last Sold Summary
- 7% Below List Price
- 5 Days On Market
Current Estimated Value $211,163

Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

480 Blackburn Point Rd Unit 4, Osprey, FL 34229

/4
Not Listed For Sale

0 N Point Rd Unit MFRA4600038, Osprey, FL 34229
0 N Point Rd Unit MFRA4600038, Osprey, FL 34229

Last Sold Summary
- 52 Days On Market
- Last Sold Price $850,000
- Apr 24, 2024
Last Listing Agent Jennifer Arciniegas CUADRA GROUP LLC

/61
$1,395,000
- 3 Beds
- 3 Baths
- 2,545 Sq Ft
3603 N Point Rd Unit 702, Osprey, FL 34229

**MAGNIFICENT VIEW from this 7th FLOOR, PENTHOUSE CONDO** Offering 3 EN SUITE BEDROOMS, 3 FULL BATHS and a treasured PRIVATE 2-CAR GARAGE! Located behind the gates of the highly sought after Oaks-Preserve, country club neighborhood in the Newest Meridian Condo Tower (Built in 2007 and featuring Hurricane Impact rated Windows and Sliding Doors). As you emerge from your private elevator foyer

Mark Lyda GENEROUS PROPERTY

3603 N Point Rd Unit 702, Osprey, FL 34229
/31
$1,995 Per Month
- 3 Beds
- 2 Baths
- 1,334 Sq Ft
- Townhouse for Rent
1755 Highland Rd, Osprey, FL 34229

Spacious duplex in Osprey with a bonus room! This Townhouse boasts 2 bedrooms and a bonus room downstairs that can be used as an office, playroom or even additional bedroom. The unit features a single car garage, washer and dryer hook ups, a screened in patio out front, an oversized living room. This community is located off us highway 41 south, right across the street from beautiful Oscar

Jennifer . STOCKTON REALTY ADVISORS LLC

1755 Highland Rd, Osprey, FL 34229
/2
$980,000 Sold Dec 09, 2025

385 N Point Rd Unit 903, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
- Built 2000
Last Sold Summary
- 11% Below List Price
- $353/SF
- 41 Days On Market
Current Estimated Value $999,976

Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

385 N Point Rd Unit 903, Osprey, FL 34229

/2
Not Listed For Sale

570 Blackburn Point Rd Unit C2, Osprey, FL 34229
- Built 2005
570 Blackburn Point Rd Unit C2, Osprey, FL 34229

Last Sold Summary
- 234 Days On Market
- Last Sold Price $35,000
- Feb 17, 2025
Last Listing Agent David Babel BRIGHT REALTY

/63
$1,250,000
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
409 N Point Rd Unit 601, Osprey, FL 34229

**FANTASTIC GULF AND BAY VIEWS FROM THIS UPDATED 6TH-FLOOR CORNER RESIDENCE** This spacious, light-filled corner unit offers nearly 2,600 sq. ft. of living space and features 3 bedrooms plus a study/den, 3 full baths, two elevator banks, two assigned second-level parking spaces, and climate-controlled storage. Located behind the secure gates of The Oaks Preserve Country Club, this residence

Mark Lyda GENEROUS PROPERTY

409 N Point Rd Unit 601, Osprey, FL 34229
/46
$4,500 Per Month
- 5 Beds
- 4.5 Baths
- 3,050 Sq Ft
- House for Rent
246 Burney Rd, Osprey, FL 34229

Brand-new construction single-family home available for rent in a prime Osprey location! This spacious residence offers 5 bedrooms + 2 dedicated office/study rooms + 4.5 bathrooms + a 2-car garage, also All windows are impact-rated, eliminating the hassle of putting up hurricane shutters while providing extra security, energy efficiency, and storm protection. and ideal for large families or those

xiaoying zhang FLORIDA MORNING REALTY LLC

246 Burney Rd, Osprey, FL 34229
/2
$235,000 Sold Jun 13, 2025

109 Woodland Place, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,223 Sq Ft
- Built 1979
Last Sold Summary
- 6% Below List Price
- $192/SF
- 144 Days On Market
Current Estimated Value $217,992

Last Listing Agent Derek Edwards KELLER WILLIAMS ON THE WATER S

109 Woodland Place, Osprey, FL 34229

/44
Est $1,095,666 Not Listed For Sale

3925 Waypoint Ave, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,323 Sq Ft
- Built 2016
3925 Waypoint Ave, Osprey, FL 34229

Last Sold Summary
- 7% Below List Price
- $508/SF
- 42 Days On Market
- Last Sold Price $1,180,000
- May 07, 2024
Last Listing Agent Barry Bright BRIGHT REALTY

/43
$875,000
- 3 Beds
- 2 Baths
- 2,188 Sq Ft
599 Pine Ranch Rd E, Osprey, FL 34229

**EXQUISITELY UPDATED, TURNKEY FURNISHED, POOL HOME** in Popular BAY OAKS ESTATES. This Stunning Residence is MOVE-IN READY (just Bring Your Suitcase!) and features a LIGHT and BRIGHT, OPEN FLOORPLAN including 3 BEDS plus STUDY/DEN and 2 FULL BATHS. The Gourmet Kitchen boasts a modern, European design with premium appliance package and counter sitting area while the primary bedroom suite offers

Mark Lyda GENEROUS PROPERTY

599 Pine Ranch Rd E, Osprey, FL 34229
/36
$2,500 Per Month
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
- Townhouse for Rent
80 Navigation Cir, Osprey, FL 34229

Turnkey fully furnished newer built 3 bedroom 2 bathroom one car garage townhouse on the second floor. Hurricane windows, gated community, with community pool, club house and gym room. 15-20 minutes to Siesta Key and about 10-15 to Nokomis Beach, Legacy Trail at the end of the street, Dogpark across the street. Walking distance to 4-5 Restaurants. Walmart across the street 3 Publixes and a Target

Krisztian Kecskes M&M PROPERTY MANAGEMENT GROUP

80 Navigation Cir, Osprey, FL 34229
/55
$480,000 Sold May 14, 2025

564 Meadow Sweet Cir, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,808 Sq Ft
- Built 2003
Last Sold Summary
- 15% Below List Price
- $265/SF
- 57 Days On Market
Current Estimated Value $490,194

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

564 Meadow Sweet Cir, Osprey, FL 34229

/65
Est $1,085,707 Not Listed For Sale

3937 Waypoint Ave, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,314 Sq Ft
- Built 2016
3937 Waypoint Ave, Osprey, FL 34229

Last Sold Summary
- 10% Below List Price
- $519/SF
- 63 Days On Market
- Last Sold Price $1,200,000
- Apr 24, 2024
Last Listing Agent Toni Turner Michael Saunders

/57
$1,499,000 New Construction
- 3 Beds
- 3.5 Baths
- 2,913 Sq Ft
360 N Point Rd, Osprey, FL 34229

**DON’T WAIT TO BUILD!** EXQUISITE, NEWLY-CONSTRUCTED and NEVER LIVED-IN, SPANISH MISSION STYLE home behind the Secure Gates of the COVETED, OAKS PRESERVE Country Club Neighborhood on Sarasota Bay waters offers superb attention to detail. This Custom-Built residence boasts 3 EN SUITE BEDROOMS + 3 FULL and 1 HALF BATHS and a desirable Open Floorplan concept. A well-equipped Chef’s Kitchen features

Mark Lyda GENEROUS PROPERTY

360 N Point Rd, Osprey, FL 34229
/46
$4,500 Per Month
- 5 Beds
- 4.5 Baths
- 3,050 Sq Ft
- House for Rent
254 Burney Rd, Osprey, FL 34229

Brand-new construction single-family home available for rent in a prime Osprey location! This spacious residence offers 5 bedrooms + 2 dedicated office/study rooms + 4.5 bathrooms + a 2-car garage, also All windows are impact-rated, eliminating the hassle of putting up hurricane shutters while providing extra security, energy efficiency, and storm protection. and ideal for large families or those

xiaoying zhang FLORIDA MORNING REALTY LLC

254 Burney Rd, Osprey, FL 34229
/2
$350,000 Sold Oct 16, 2025

240 Patterson Ave, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,360 Sq Ft
- Built 1982
Last Sold Summary
- 7% Below List Price
- $257/SF
- 157 Days On Market
Current Estimated Value $345,874

Last Listing Agent Janice Melzer Langa COLDWELL BANKER REALTY

240 Patterson Ave, Osprey, FL 34229

/22
Est $278,456 Not Listed For Sale

101 Navigation Cir Unit 101, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Built 2014
101 Navigation Cir Unit 101, Osprey, FL 34229

Last Sold Summary
- 12% Below List Price
- $278/SF
- 80 Days On Market
- Last Sold Price $315,000
- Apr 30, 2024
Last Listing Agent Kimberly Stanford REALNET FLORIDA REAL ESTATE

/79
$530,000
- 3 Beds
- 2.5 Baths
- 2,414 Sq Ft
562 Oak Bay Dr, Osprey, FL 34229

One or more photo(s) has been virtually staged. Beautiful home in the desirable Bay Oaks neighborhood, known for its winding roads, mature landscaping, and minimal traffic. Perfectly situated between The Oaks Golf Course and Stoneybrook Golf & Country Club, this home offers the lifestyle and views without the high price tag or association fees.The property welcomes you with a circular

Julianna Burns BERKSHIRE HATHAWAY HOMESERVICE

562 Oak Bay Dr, Osprey, FL 34229
/15
$3,500 Per Month
- 3 Beds
- 2 Baths
- 1,648 Sq Ft
- House for Rent
2068 Preymore St, Osprey, FL 34229

Welcome home to this charming and beautifully maintained 3-bedroom, 2-bath residence located on a great community. Step inside to a spacious open floor plan featuring a generous great room, a dedicated dining area, and a large primary suite. Cathedral ceilings, pocket sliding doors, and fluid room transitions create an airy atmosphere perfect for easy living and entertaining. The bright, eat-in

Kenia Rivas PREFERRED SHORE LLC

2068 Preymore St, Osprey, FL 34229
/2
$1,285,000 Sold Jun 30, 2025

393 N Point Rd Unit 801, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 3,029 Sq Ft
- Built 2001
Last Sold Summary
- 22% Below List Price
- $424/SF
- 204 Days On Market
Current Estimated Value $1,230,624

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

393 N Point Rd Unit 801, Osprey, FL 34229

/40
Est $296,351 Not Listed For Sale

163 Explorer Dr Unit 103, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
- Built 2014
163 Explorer Dr Unit 103, Osprey, FL 34229

Last Sold Summary
- 14% Below List Price
- $276/SF
- 28 Days On Market
- Last Sold Price $343,000
- Jan 24, 2024
Last Listing Agent Lita Sciturro Smith LITA SCITURRO-SMITH LIC. REAL ESTATE BROKER

Showing Results 81 - 120, Page 3 of 18

Florida Sarasota County Osprey

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