Osprey, FL Homes

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  /84

  $970,000

  • 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. Waterfront Elegance at Blackburn Harbor! Experience the comfort of a home with the convenience of condo living in this spacious 3-bedroom, 3.5-bath plus den residence offering 3,771 sq. ft. of beautifully designed space and 10-foot tray ceilings throughout and a new roof. Enjoy panoramic water views from the gourmet kitchen, featuring wood

  

  Cynthia Brock

  GULF SANDS REALTY, LLC

  (941) 698-6279

  6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229
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• 

  

  

  /18

  $1,850 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • House for Rent

  455 Pennsylvania Ave, Osprey, FL 34229

  Fully Furnished 2BR/1BA Turnkey Home in Osprey, FLUnique, peaceful property with native wildflower garden, beach gear, and old-Florida charm. Located in the quiet fishing village of Osprey, this FULLY FURNISHED home includes:•Upgraded kitchen with stainless steel appliances, granite counters, and all essentials•New washer/dryer•Enclosed lanai•High-speed WiFi, water, sewer,

  455 Pennsylvania Ave, Osprey, FL 34229
• 

  

  /2

  $250,000 Sold Oct 23, 2025

  • 1,325 Sq Ft
  • $189/SF
  • 491 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  207 Woodland Dr Unit 207, Osprey, FL 34229

  Welcome to this beautifully appointed, well-cared for and fully furnished 2-bedroom, 2-bath condo located in the sought-after Pine Run community. It is completely turnkey; all you need to bring are your clothes! This second-floor unit has been tastefully updated and comes equipped with everything you need to move right in, including all furniture, beds, bedding, all kitchenware, appliances, and

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  207 Woodland Dr Unit 207, Osprey, FL 34229
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  /2

  Est $236,458 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 595 Sq Ft

  51 MacEwen Dr Unit 13, Osprey, FL 34229

  51 MacEwen Dr Unit 13, Osprey, FL 34229
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  /73

  $2,550,000

  • 3 Beds
  • 3.5 Baths
  • 4,519 Sq Ft

  852 MacEwen Dr, Osprey, FL 34229

  **CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and

  Mark Lyda GENEROUS PROPERTY

  852 MacEwen Dr, Osprey, FL 34229
• 

  

  /25

  $3,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,064 Sq Ft
  • House for Rent

  554 Pine Ranch East Rd, Osprey, FL 34229

  ANNUAL/ GENTLY FURNISHED 4 BED/2.5 BATH. The home is gently furnished which will work perfectly for the family who has some furniture already.Available November1st - 9 month minimum - come stay here while your build your home.Master has a king bed with ensuite bathroom.- walk in shower, garden tub. Guest room has twin beds, 2nd guest room has a built in office and a Murphy bed. 4th

  Annabelle Newland STOCKTON REALTY ADVISORS LLC

  554 Pine Ranch East Rd, Osprey, FL 34229
• 

  /2

  $210,000 Sold Oct 22, 2025

  • 5 Days On Market

  • Built 2006

  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
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  /2

  Est $401,002 Not Listed For Sale

  • 2 Beds

  19 Westview Dr, Osprey, FL 34229

  19 Westview Dr, Osprey, FL 34229
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  /69

  $699,000

  • 4 Beds
  • 3 Baths
  • 2,267 Sq Ft

  471 Park Trace Blvd, Osprey, FL 34229

  SIGNIFICANT PRICE IMPROVEMENT!! Welcome to your dream home! This stunning, custom-built 4 bedroom, 3 bathroom residence perfectly blends luxury, comfort, and location for the ideal Florida lifestyle. This home is nestled in a highly sought-after neighborhood offering peace, privacy, and a vibrant community feel with low HOA fees. It is situated on an over-sized corner lot, with exceptional

  Bill Cantrell FLORIDA HOME TEAM LLC

  471 Park Trace Blvd, Osprey, FL 34229
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  /49

  $2,995 per month

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • Condo for Rent

  127 Explorer Dr Unit 127 Explorer Dr, Osprey, FL 34229

  Great location - short drive to the best Florida beaches, golf clubs, Oscar Schrer State park, Legacy trail, right between cultural and culinary wealth of downtown Sarasota and Venice. Walking distance to Pine View School, playground and dog park across the street. Gated community with heated pool, fitness center and club house, newer buildings with hurricane -withstand features. One car garage

  127 Explorer Dr Unit 127 Explorer Dr, Osprey, FL 34229
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  /2

  $350,000 Sold Oct 16, 2025

  • 1,360 Sq Ft
  • $257/SF
  • 157 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1982

  240 Patterson Ave, Osprey, FL 34229

  Charming 3-bedroom, 2-bath bungalow with no HOA or deed restrictions—perfect for boaters, RV owners, or anyone seeking freedom and flexibility. Situated in a prime location close to beaches, waterfront dining, the Legacy Trail, Selby Botanical Gardens, Pine View school is 1 mile away (this high school is ranked numbr 18 nationwide and number 1 in Florida), shopping (Walmart Super Center) and

  Janice Melzer Langa COLDWELL BANKER REALTY

  240 Patterson Ave, Osprey, FL 34229
• 

  /2

  Est $43,897 Not Listed For Sale

  • Studio

  570 Blackburn Point Rd Unit Siesta 26, Osprey, FL 34229

  570 Blackburn Point Rd Unit Siesta 26, Osprey, FL 34229
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  /68

  $1,970,000

  • 4 Beds
  • 4 Baths
  • 3,286 Sq Ft

  140 Sugar Mill Dr, Osprey, FL 34229

  **BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE ESTATE with Lush Garden Landscape** is located behind the Secure Gates of The Oaks Bayside, Country Club neighborhood. Featuring 4 BEDROOMS (2 En Suite) and 4 FULL BATHS, this Open Floorplan with Soaring Ceilings, Custom Built-Ins, Crown Moldings and refined details throughout is ideal for entertaining both inside and out! The Impressive

  Mark Lyda GENEROUS PROPERTY

  140 Sugar Mill Dr, Osprey, FL 34229
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  $3,550 per month

  • 3 Beds
  • 2 Baths
  • 2,225 Sq Ft
  • House for Rent

  603 Pine Ranch East Rd, Osprey, FL 34229

  *AVAILABLE NOVEMBER 15, 2025 — PREVIEW BY APPOINTMENT ONLY*Currently occupied — showings available by appointment only.This beautifully updated 3-bedroom, 2-bathroom home, features a desirable split floor plan and a spacious 2-car garage. Offered unfurnished, with pool and yard maintenance included in the rent.HIGHLIGHTS:Open-concept layout designed for comfort, entertaining,

  Marina Yanovskiy ALL SEASONS REALTY LLC

  603 Pine Ranch East Rd, Osprey, FL 34229
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  /2

  $625,000 Sold Oct 10, 2025

  • 2,298 Sq Ft
  • $272/SF
  • 260 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2001

  644 Rivendell Blvd, Osprey, FL 34229

  Built by Rutenberg Homes, this residence offers high tray ceilings and a smart, open layout. The formal living and family rooms, along with the en-suite primary bedroom, open to the lanai. The dining room features custom built-ins, two guest bedrooms share a bath, and a private in-law suite/office includes its own bath and lanai access. The kitchen, with newer appliances, a breakfast bar, and an

  Veronica Manes MICHAEL SAUNDERS & COMPANY

  644 Rivendell Blvd, Osprey, FL 34229
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  /4

  Not Listed For Sale

  0 N Point Rd Unit MFRA4600038, Osprey, FL 34229

  0 N Point Rd Unit MFRA4600038, Osprey, FL 34229
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  /82

  $1,350,000

  • 5 Beds
  • 3.5 Baths
  • 3,481 Sq Ft

  296 Pine Ranch Trail, Osprey, FL 34229

  **THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** & SELLER IS OFFERING A $25,000.00 CREDIT toward rate buy down/closing cost with acceptable contract. Welcome to your private retreat nestled in one of Osprey’s most desirable enclaves. This beautifully situated home rests on a lush greenbelt lot that borders the fairways of a

  Deborah Frederick ASHTON LAKES REALTY INC

  296 Pine Ranch Trail, Osprey, FL 34229
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  /56

  $4,900 per month

  • 3 Beds
  • 3 Baths
  • 2,981 Sq Ft
  • House for Rent

  140 Sea Anchor Dr, Osprey, FL 34229

  PREVIEW BY APPOINTMENT ONLY. This 3 bed, 3 bath, plus office and heated POOL home is located in the beautiful Southbay Yacht and Racquet Club community and within the Pineview School District (an A+ rated school). Southbay has its own deep water marina and offers 4 miles of walking trails throughout the neighborhood, lighted tennis courts, bocce ball, basketball courts, shuffle board courts, a

  Chantelle Edalgo EXIT KING REALTY

  140 Sea Anchor Dr, Osprey, FL 34229
• 

  /2

  $700,000 Sold Oct 08, 2025

  • 2,589 Sq Ft
  • $270/SF
  • 160 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2003

  826 Oak Briar Ln, Osprey, FL 34229

  Welcome to this MODERN 4-Bedroom, 3-Bath POOL HOME located in the highly desirable PARK TRACE ESTATES in Osprey, Florida — perfectly situated in a PRIME LOCATION between Sarasota, Nokomis, and Venice. Boasting over 3,000 sq. ft. under roof along with $110,000 of RECENT IMPROVEMENTS including: NEW TILE ROOF (’23), NEW impact windows (’23, partial), NEW front door (’23), NEW high-end air condition

  Peter LaSalle PREFERRED SHORE LLC

  826 Oak Briar Ln, Osprey, FL 34229
• 

  

  /44

  Est $1,107,884 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,323 Sq Ft

  3925 Waypoint Ave, Osprey, FL 34229

  3925 Waypoint Ave, Osprey, FL 34229
• 

  

  /38

  $795,000

  • 3 Beds
  • 2 Baths
  • 2,443 Sq Ft

  901 Reflection Way, Osprey, FL 34229

  LOCATION! LOCATION! Tucked away on a quiet cul-de-sac and resting on a corner lot, this METICULOUSLY MAINTAINED, Custom-built, JOHN CANNON home in exclusive North Creek Estates offers the perfect blend of privacy, luxury, and convenience. With a NEW ROOF (2020), low HOA fees, and 2,443 sq. ft. of thoughtfully designed living space, this 3-Bedroom + Office/Den, 2-Bath residence is MOVE-IN READY

  Mark Lyda GENEROUS PROPERTY

  901 Reflection Way, Osprey, FL 34229
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  /41

  $2,350 per month

  • 2 Beds
  • 2 Baths
  • 1,391 Sq Ft
  • Condo for Rent

  2313 Jessie Harbor Dr Unit 2302, Osprey, FL 34229

  ANNUAL UNFURNISHED VILLA AVAILABLE FOR LEASE IN BLACKBURN HARBOR IN OSPREY! This beautiful 2BR 2BA villa has a large lanai with peaceful views over Blackburn Harbor and features Brazilian Cherry hardwood floors, stainless steel appliances and a private one car garage. The entire condo has been freshly painted. Blackburn Harbor is a gated community and offers many amenities, which include a heated

  Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

  2313 Jessie Harbor Dr Unit 2302, Osprey, FL 34229
• 

  /2

  $200,000 Sold Oct 06, 2025

  • 1,284 Sq Ft
  • $156/SF
  • 9 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1953

  444 Washington Ave, Osprey, FL 34229

  Handyman or tear down. Potential of 2 buildable lots. The carport area roof lifted in last hurricane.

  Hansel Pitts COLDWELL BANKER SARASOTA CENT.

  444 Washington Ave, Osprey, FL 34229
• 

  

  /65

  Est $1,094,565 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,314 Sq Ft

  3937 Waypoint Ave, Osprey, FL 34229

  3937 Waypoint Ave, Osprey, FL 34229
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  /62

  $965,000

  • 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
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  /36

  $2,500 per month

  • 2 Beds
  • 2 Baths
  • 1,069 Sq Ft
  • House for Rent

  305 Bay Vista Ave, Osprey, FL 34229

  Welcome to this stunning two-bedroom, two-bathroom retreat, perfectly designed for relaxation and entertainment!As you step inside, you'll notice the bright and airy open-plan living area, flooded with natural light pouring in through the large windows.But the true showstopper is the incredible backyard oasis! The expansive fenced yard beckons you to unwind and enjoy the fresh

  Jennifer . STOCKTON REALTY ADVISORS LLC

  305 Bay Vista Ave, Osprey, FL 34229
• 

  /2

  $1,275,000 Sold Sep 30, 2025

  • 3,241 Sq Ft
  • $393/SF
  • 7 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2003

  364 Renoir Dr, Osprey, FL 34229

  Welcome to your dream coastal retreat! This stunning waterfront home is perfectly situated on a saltwater canal with direct Gulf access and no bridges....a boater’s dream. Enjoy Florida living at its finest with luxurious indoor and outdoor features that truly set this property apart. A spacious paver driveway leads to this elegant residence, featuring a heated pool and spa, outdoor kitchen, and

  Lore Miller RESULTS REALTY GROUP LLC

  364 Renoir Dr, Osprey, FL 34229
• 

  

  /22

  Est $288,506 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft

  101 Navigation Cir Unit 101, Osprey, FL 34229

  101 Navigation Cir Unit 101, Osprey, FL 34229
• 

  

  /78

  $1,095,000

  • 5 Beds
  • 4 Baths
  • 3,938 Sq Ft

  820 Placid Lake Dr, Osprey, FL 34229

  Discover this expansive 5-bedroom, 4-bathroom home with an oversized bonus room and 3,938 sq. ft. of living space, perfectly situated on a 10,548 sq. ft. lakefront lot. Recent upgrades provide peace of mind and modern comfort, including a new tile roof (2024), new zoned HVAC units (2022), a new pool heater (2024), a new water heater (2025) with a 25-year whole-home water conditioner, fresh

  Ali Marks LOYD ROBBINS & CO. LLC

  820 Placid Lake Dr, Osprey, FL 34229
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  /44

  $3,950 per month

  • 3 Beds
  • 3 Baths
  • 1,781 Sq Ft
  • House for Rent

  451 N Shore Dr, Osprey, FL 34229

  Welcome to your new spacious home in the beautiful waterfront neighborhood of Sorrento Shores. As you approach this three bedroom, three bath POOL house you will notice the quiet charm that this highly sought-after neighborhood provides. The streets are lined with tropical fruit trees, palms, and plants that create a tranquil atmosphere. The open concept, split floor plan, and wonderfully updated

  Justin Ulrich ZACHOS REALTY & DESIGN GROUP

  451 N Shore Dr, Osprey, FL 34229
• 

  /2

  $525,000 Sold Sep 30, 2025

  • 1,221 Sq Ft
  • $430/SF
  • 2 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1968

  116 Villa Dr Unit 116, Osprey, FL 34229

  Bring your boat and move right in! This home has been completely gutted and rebuilt from the ground up with nothing left untouched. Every finish, fixture, and feature has been carefully chosen with quality in mind. Offering a direct canal view, and just steps from the heated community pool, this property blends luxury living with a relaxed coastal lifestyle.Inside, enjoy the peace of mind

  Marco Guadagnini PREFERRED SHORE LLC

  116 Villa Dr Unit 116, Osprey, FL 34229
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  /40

  Est $296,744 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,244 Sq Ft

  163 Explorer Dr Unit 103, Osprey, FL 34229

  163 Explorer Dr Unit 103, Osprey, FL 34229
• 

  

  /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
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  /9

  $2,395 per month

  • 2 Beds
  • 2 Baths
  • 1,145 Sq Ft
  • Townhouse for Rent

  1817 Highland Rd, Osprey, FL 34229

  Lovely 2 bed/2 bth well maintained townhouse with a 2 car garage Set in a private enclave in the desirable West of Trail Osprey location with a Community pool. Close to beaches, restaurants and shopping.

  Steven Koleno BEYCOME OF FLORIDA LLC

  1817 Highland Rd, Osprey, FL 34229
• 

  /2

  $410,000 Sold Sep 30, 2025

  • 1,541 Sq Ft
  • $266/SF
  • 98 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  321 Sorrento Dr, Osprey, FL 34229

  Welcome to this beautifully maintained Sorrento Shores pool home, exuding timeless Mediterranean charm. Built in 1988, this residence offers a warm, inviting atmosphere with classic architectural details such as a tile roof, stucco exterior, and arched entryways.Inside, you'll find a spacious and functional layout ideal for both everyday living and entertaining. The sunlit living areas

  Jim Comly EXIT KING REALTY

  321 Sorrento Dr, Osprey, FL 34229
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  /34

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 959 Sq Ft

  201 Palm Air Dr, Osprey, FL 34229

  201 Palm Air Dr, Osprey, FL 34229
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  /62

  $1,695,000

  • 3 Beds
  • 3.5 Baths
  • 4,241 Sq Ft

  909 MacEwen Dr, Osprey, FL 34229

  **STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace,

  Mark Lyda GENEROUS PROPERTY

  909 MacEwen Dr, Osprey, FL 34229
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  /38

  $6,000 per month

  • 3 Beds
  • 3 Baths
  • 2,055 Sq Ft
  • Condo for Rent

  409 N Point Rd Unit 802, Osprey, FL 34229

  **TURNKEY FURNISHED, PENTHOUSE Condo Unit has been FULLY RENOVATED** This 8TH FLOOR, Light and Bright, 3-BEDROOM plus 3 FULL BATH dwelling with screened balcony is available beginning in September, 2025. The 2055sf floorplan is tastefully furnished and offers superb views of the Intracoastal Waterway and Gulf. This unit was fully renovated in 2023 with updated oak hardwood flooring, new kitchen

  Mark Lyda GENEROUS PROPERTY

  409 N Point Rd Unit 802, Osprey, FL 34229
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  /2

  $640,000 Sold Sep 25, 2025

  • 1,887 Sq Ft
  • $339/SF
  • 48 Days On Market

  • Built 1997

  6 Bay Acres Ave, Osprey, FL 34229

  Exceptional Investment Opportunity – Profitable Remodeled Duplex in Prime Osprey Location! Updated in 2021 with a new roof, modern kitchens, contemporary appliances, stylish flooring, and upgraded electrical systems. This income-producing gem is currently generating $112,000 in gross annual short-term rental income, making it an unbeatable addition to your investment portfolio.Nestled on

  Bogdan Osipov OSIPOV GROUP REAL ESTATE

  6 Bay Acres Ave, Osprey, FL 34229
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  /46

  Est $600,273 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,004 Sq Ft

  2007 Cordes St, Osprey, FL 34229

  2007 Cordes St, Osprey, FL 34229

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