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    1. *40 Hour Work Week*
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  • Buyer
    1. All Listings
    2. Featured Listings
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    25. New Homes vs Resale
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    1. Sell My Home
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    3. 10 Questions Agents Hate
    4. 27 Seller Tips
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    8. Buy This Home Ill Buy Yours
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    15. Get the Price You Want
    16. Guaranteed Offer
    17. How to Sell a Home that Didnt Sell
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157 Properties

157 Properties Available In Osprey

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FL >Osprey >
Market Insights
116 NAVIGATION CIR #106, Osprey, FL 34229
1/61 61

$325,000

Open Sun 12PM-2PM

Condo

3 Beds 2 Baths 1,430 SqFt

116 NAVIGATION CIR #106, Osprey, FL 34229

Location, Lifestyle, and Peace of Mind — All in One! <br> <br>Welcome home to this beautifully appointed 3-bedroom, 2-ba...

Listed by COLDWELL BANKER REALTY

Stellar MLS
238 PALM AIR DR, Osprey, FL 34229
1/25 25

$234,000

Open 7/26 11AM-2PM

Manufactured Home

2 Beds 2 Baths 1,152 SqFt

238 PALM AIR DR, Osprey, FL 34229

AN ARBORS BEAUTY in one of Florida's most-sought-after 55+ parks. You won't believe how BIG and BEAUTIFUL this home is ...

Listed by FINE PROPERTIES

Stellar MLS
523 HABITAT BLVD, Osprey, FL 34229
1/62 62

$785,500

Open Sun 1PM-3PM

Single Family Home

4 Beds 3 Baths 2,314 SqFt

523 HABITAT BLVD, Osprey, FL 34229

In the Lee Wetherington-built community of Willowbend is a stunning home. This enchanting residence borders a sparkling ...

Listed by PREMIER SOTHEBY'S INTERNATIONAL REALTY

Stellar MLS
250 HIDDEN BAY DR #302, Osprey, FL 34229
1/65 65

$710,000

Open Sun 1PM-4PM

Condo

3 Beds 2 Baths 1,937 SqFt

250 HIDDEN BAY DR #302, Osprey, FL 34229

WHAT A VIEW! Prepare to be captivated by jaw-dropping sunsets from your oversized, private, screened-in balcony, offerin...

Listed by COLDWELL BANKER REALTY

Stellar MLS
851 PLACID LAKE DR, Osprey, FL 34229
1/34 34

$800,000

Open Sun 8AM-7PM

Single Family Home

5 Beds 4 Baths 3,395 SqFt

851 PLACID LAKE DR, Osprey, FL 34229

One or more photo(s) has been virtually staged. Your dream home is waiting for you! This home has Fresh Interior Paint, ...

Listed by OPENDOOR BROKERAGE LLC

Stellar MLS
678 CRANE PRAIRIE WAY, Osprey, FL 34229
1/49 49

$897,000

Open 7/26 1PM-3PM

Single Family Home

3 Beds 2 Baths 2,483 SqFt

678 CRANE PRAIRIE WAY, Osprey, FL 34229

It's always about the view and the new tile roof in June 2025 plus the Tesla whole-house solar system comprising 26 roof...

Listed by PREMIER SOTHEBY'S INTERNATIONAL REALTY

Stellar MLS
4267 EXPEDITION WAY, Osprey, FL 34229
1/35 35

$310,000

Open Sun 12PM-2PM

Condo

2 Beds 2 Baths 1,135 SqFt

4267 EXPEDITION WAY, Osprey, FL 34229

Welcome to Bay Street Village, Osprey - Perfectly nestled between the vibrant cities of Sarasota and Venice - only minut...

Listed by COLDWELL BANKER REALTY

Stellar MLS
4428 CONCHFISH LN, Osprey, FL 34229
1/13 13

$599,000

Open Sun 1PM-3PM

Single Family Home

4 Beds 2 Baths 1,861 SqFt

4428 CONCHFISH LN, Osprey, FL 34229

Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not co...

Listed by HORIZON REALTY INTERNATIONAL

Stellar MLS
766 SHADOW BAY WAY, Osprey, FL 34229
1/68 68

$998,000

Open Sun 2PM-4PM

Single Family Home

4 Beds 3 Baths 3,438 SqFt

766 SHADOW BAY WAY, Osprey, FL 34229

Nestled on a quiet street in the highly sought-after Rivendell community, this former Arthur Rutenberg model home featur...

Listed by COLDWELL BANKER SARASOTA CENT.

Stellar MLS
296 PINE RANCH TRL, Osprey, FL 34229
3D

$1,450,000

Open Sun 1PM-4PM

Single Family Home

5 Beds 4 Baths 3,481 SqFt

296 PINE RANCH TRL, Osprey, FL 34229

**THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** ...

Listed by ASHTON LAKES REALTY INC

Stellar MLS
1313 THORNAPPLE DR, Osprey, FL 34229
1/40 40

$549,000

Open 7/26 2PM-4PM

Single Family Home

3 Beds 3 Baths 2,082 SqFt

1313 THORNAPPLE DR, Osprey, FL 34229

Stunning finishes welcome you to this enchanting Lee Wetherington-built residence in Willowbend. Incredibly light and br...

Listed by PREMIER SOTHEBYS INTL REALTY

Stellar MLS
120 VILLA DR #120, Osprey, FL 34229
1/55 55

$550,000

Open Sun 12PM-3PM

Single Family Home

2 Beds 2 Baths 1,404 SqFt

120 VILLA DR #120, Osprey, FL 34229

Waterfront with your own private dock with 10,000lb elevator lift. This home is being offered fully furnished from the i...

Listed by COLDWELL BANKER SARASOTA CENT.

Stellar MLS
312 YACHT HARBOR DR, Osprey, FL 34229
1/69 69

$2,495,000

Open Sun 1PM-3PM

Single Family Home

4 Beds 4 Baths 2,572 SqFt

312 YACHT HARBOR DR, Osprey, FL 34229

One or more photo(s) has been virtually staged. Considered one of the finest community-owned marinas on the west coast o...

Listed by PREMIER SOTHEBYS INTL REALTY

Stellar MLS
191 PALM AIR DR, Osprey, FL 34229
1/45 45

$185,000

Open 7/26 2:30PM-5PM

Manufactured Home

2 Beds 2 Baths 1,376 SqFt

191 PALM AIR DR, Osprey, FL 34229

Come home to this tastefully-furnished, well-maintained spacious home in a top-of-the-line, perfectly located Co-Op park...

Listed by FINE PROPERTIES

Stellar MLS
607 OAK RIVER CT, Osprey, FL 34229
1/45 45

$2,695

New

Single Family Home

3 Beds 2 Baths 1,814 SqFt

607 OAK RIVER CT, Osprey, FL 34229

Don't miss out on this 3 bed/2bath with 2 car garage. Immaculate home. Light and bright. <br>Great floor plan includes a...

Listed by PMI SOUTHWEST FLORIDA

Stellar MLS
478 ORISKANY CT, Osprey, FL 34229
1/100 100

$2,999,000

New

Single Family Home

4 Beds 7 Baths 5,778 SqFt

478 ORISKANY CT, Osprey, FL 34229

Welcome to your dream home, a sanctuary of elegance and comfort nestled on an exclusive, private street with only nine r...

Listed by COLDWELL BANKER REALTY

Stellar MLS
Osprey, FL 34229
1/39 39

$4,200

New

Condo

3 Beds 2 Baths 1,937 SqFt

Osprey, FL 34229

NOW AVAILABLE FOR RENT – READY FOR IMMEDIATE OCCUPANCY <br>Modern Elegance at Edgewater | Stunning Condo with Bay Views ...

Listed by BERKSHIRE HATHAWAY HOMESERVICE

Stellar MLS
385 N POINT RD #404, Osprey, FL 34229
3D

$925,000

New

Condo

3 Beds 3 Baths 2,778 SqFt

385 N POINT RD #404, Osprey, FL 34229

**STUNNINGLY UPDATED CONDO with Breathtaking Water & Preserve Views that rival those of higher floors!** This LARGE, COR...

Listed by GENEROUS PROPERTY

Stellar MLS
852 MACEWEN DR, Osprey, FL 34229
3D

$2,550,000

New

Single Family Home

3 Beds 4 Baths 4,519 SqFt

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 ...

Listed by GENEROUS PROPERTY

Stellar MLS
385 N POINT RD #701, Osprey, FL 34229
3D

$1,499,500

New

Condo

3 Beds 3 Baths 2,594 SqFt

385 N POINT RD #701, Osprey, FL 34229

**INCOMPARABLE VIEW! 7th FLOOR, CORNER CONDO UNIT WITH UNOBSTRUCTED SOUTH AND WEST PANORAMA. This Spacious unit of near...

Listed by GENEROUS PROPERTY

Stellar MLS
594 PINE RANCH EAST RD, Osprey, FL 34229
3D

$649,995

New

Single Family Home

3 Beds 3 Baths 2,298 SqFt

594 PINE RANCH EAST RD, Osprey, FL 34229

Discover this beautifully maintained 3-bedroom, 2-bathroom home nestled in a peaceful, private community just steps from...

Listed by DALTON WADE INC

Stellar MLS
462 E MACEWEN DR, Osprey, FL 34229
1/100 100

$1,550,000

Active

Single Family Home

3 Beds 3 Baths 2,611 SqFt

462 E MACEWEN DR, Osprey, FL 34229

This completely remodeled home in The Oaks Clubside, set on nearly an acre of mature, meticulously landscaped grounds, i...

Listed by COLDWELL BANKER REALTY

Stellar MLS
650 CRANE PRAIRIE WAY, Osprey, FL 34229
1/100 100

$3,750

Active

Single Family Home

4 Beds 4 Baths 3,183 SqFt

650 CRANE PRAIRIE WAY, Osprey, FL 34229

Now Available – Lease Option or Lease Purchase Opportunity in Willowbend! <br> Lease Option: Lease now with the option—b...

Listed by KELLER WILLIAMS ON THE WATER

Stellar MLS
5100 JESSIE HARBOR DR #701, Osprey, FL 34229
1/47 47

$725,000

Active

Condo

3 Beds 3 Baths 2,484 SqFt

5100 JESSIE HARBOR DR #701, Osprey, FL 34229

Perched on the top floor of Blackburn Harbor Residences, this 3-bedroom, 3-bath end unit is just under 2500 square feet ...

Listed by WILLIAM RAVEIS REAL ESTATE

Stellar MLS
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Buy With Boland

Whitney Boland

+1(727) 657-1265 whitney@buywithboland.com

2234 Lithia Center Lane, Valrico, Florida, 33596, USA
    • Home
      Seller
      1. Sell My Home
      2. Home Estimate
      3. 10 Questions Agents Hate
      4. 27 Seller Tips
      5. Avoid Legal Mistakes
      6. Avoid these mistakes
      7. Become a VIP Seller
      8. Buy This Home Ill Buy Yours
      9. Cash For your Home
      10. Divorce
      11. Empty Nesting
      12. Find Out What This Home Is Sold For
      13. For Sale By Owner
      14. Getting Best Price
      15. Get the Price You Want
      16. Guaranteed Offer
      17. How to Sell a Home that Didnt Sell
      18. How to Sell Your Home for More
      19. Kids and Moving
      20. Pets and Moving
      21. Pass Your Inspection
      22. Why Didnt My Home Sell
    • General
      1. *40 Hour Work Week*
      2. *Ambitious Real Estate Agent Wanted NOW*
      3. *Your Referrals Help The Kids
      4. Join Us Agents
      5. Local Real Estate Information
      6. Our Team
      7. Refer a Friend
      8. Save on Expenses
      About
      1. My Team
      2. About Us
      3. Contact Us
      4. Reviews
      5. Blogs
    • Buyer
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      4. 50 Homes For 50 Fallen
      5. 10 Best Buy Hotlist
      6. 13 Extra Cost
      7. 6 Buyer Mistakes
      8. 9 Common Buyer Traps
      9. Ask a Real Estate Expert
      10. Best Financing Rate
      11. Buy With Zero Down
      12. First Time Buyer Hotlist
      13. Exclusive Fixer Upper Hotlist
      14. Fixer Uppers: Myths and Facts
      15. Foreclosures Hotlist
      16. Get New Listings
      17. Home Warranty
      18. Homes with Land Hotlist
      19. Homes with Pools Hotlist
      20. Hotlist of Upscale Homes
      21. Mortgage Pre-Approval
      22. Moving Company
      23. Moving Up
      24. Multiple Listing
      25. New Homes vs Resale
      26. No Money Down Hotlist
      27. Open House
      28. Our Homes for Sale
      29. Real Estate Lawyer
      30. Save $5000 Guaranteed
      31. Save Thousands
      32. Stop Paying Rent
      33. Sunday Tour of Homes
      34. VIP INSIDER ACCESS
      Market Snapshot

Get My App

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.
site logo
Buy With Boland

Whitney Boland

+1(727) 657-1265 whitney@buywithboland.com

2234 Lithia Center Lane, Valrico, Florida, 33596, USA
    • Home
      Seller
      1. Sell My Home
      2. Home Estimate
      3. 10 Questions Agents Hate
      4. 27 Seller Tips
      5. Avoid Legal Mistakes
      6. Avoid these mistakes
      7. Become a VIP Seller
      8. Buy This Home Ill Buy Yours
      9. Cash For your Home
      10. Divorce
      11. Empty Nesting
      12. Find Out What This Home Is Sold For
      13. For Sale By Owner
      14. Getting Best Price
      15. Get the Price You Want
      16. Guaranteed Offer
      17. How to Sell a Home that Didnt Sell
      18. How to Sell Your Home for More
      19. Kids and Moving
      20. Pets and Moving
      21. Pass Your Inspection
      22. Why Didnt My Home Sell
    • General
      1. *40 Hour Work Week*
      2. *Ambitious Real Estate Agent Wanted NOW*
      3. *Your Referrals Help The Kids
      4. Join Us Agents
      5. Local Real Estate Information
      6. Our Team
      7. Refer a Friend
      8. Save on Expenses
      About
      1. My Team
      2. About Us
      3. Contact Us
      4. Reviews
      5. Blogs
    • Buyer
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      4. 50 Homes For 50 Fallen
      5. 10 Best Buy Hotlist
      6. 13 Extra Cost
      7. 6 Buyer Mistakes
      8. 9 Common Buyer Traps
      9. Ask a Real Estate Expert
      10. Best Financing Rate
      11. Buy With Zero Down
      12. First Time Buyer Hotlist
      13. Exclusive Fixer Upper Hotlist
      14. Fixer Uppers: Myths and Facts
      15. Foreclosures Hotlist
      16. Get New Listings
      17. Home Warranty
      18. Homes with Land Hotlist
      19. Homes with Pools Hotlist
      20. Hotlist of Upscale Homes
      21. Mortgage Pre-Approval
      22. Moving Company
      23. Moving Up
      24. Multiple Listing
      25. New Homes vs Resale
      26. No Money Down Hotlist
      27. Open House
      28. Our Homes for Sale
      29. Real Estate Lawyer
      30. Save $5000 Guaranteed
      31. Save Thousands
      32. Stop Paying Rent
      33. Sunday Tour of Homes
      34. VIP INSIDER ACCESS
      Market Snapshot

Get My App

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.