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1795 HIGHLAND RD,  OSPREY, FL 34229

MLS# A4684679.  3 beds.  3.0 baths.  Single Family Home.  Active

$150.00 Monthly Fees.  $2,809 in taxes (2025)

$385,000

 

Remarks:

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Perfectly positioned west of the Trail in the desirable coastal community of Towns-End Shores, this versatile property offers an exceptional opportunity to enjoy the Florida lifestyle while generating income. This home provides both peace of mind and outstanding value in one of Sarasota County’s most sought-after areas. Designed with flexibility in mind, the property features a unique two-level layout that allows you to live upstairs while renting the lower-level in-law suite, currently producing $1, 500 per month on a month-to-month lease. The private suite includes its own entrance, bedroom, bathroom, kitchen, and living area, creating an ideal setup for rental income, guests, or multigenerational living. Upstairs, the two bedroom and two bathroom primary residence offers an open and inviting layout filled with natural light. The kitchen features granite countertops, solid wood cabinetry, and a functional layout that flows easily into the living and dining areas. Crown molding, tray ceilings, wood flooring, and thoughtful design elements add character and comfort throughout the home. Recent updates provide valuable peace of mind, including a new air conditioning system and water heater installed in 2024, while the air-conditioned garage adds versatility for storage, hobbies, or a workshop. Plus, NEW ROOF 2026 with 10 year warranty! NO FLOOD ZONE — meaning flood insurance is not required. Outdoor living is just as appealing. Residents enjoy low HOA dues and access to the sunny community pool, along with the rare convenience of a private kayak launch, allowing you to explore nearby waterways and mangroves with ease. The location truly sets this property apart. Bike to the beach, explore nearby Oscar Scherer State Park, or access the Legacy Trail just minutes away for miles of scenic biking and walking. You are also conveniently located near South Bay and the beautiful beaches of Casey Key, along with local dining, shopping, and coastal attractions. Whether you are seeking a primary residence with income potential, a coastal retreat, or an investment property in a prime west-of-the-trail location, this home delivers flexibility, lifestyle, and value all in one. Schedule your private showing today and experience the possibilities this unique property offers.

Quick Info:

  • Listing is courtesy Of: RE/MAX ALLIANCE GROUP ((941-954-5454))
  • Listing Agent: Rachel Tritschler ((941-993-5892))
  • Days on yellowkey: 38
  • Property Type: Single Family Home
  • Beds: 3
  • Baths: 3.0
  • Living Area Square Feet: 1879
  • Built 1999
  • Taxes: $2,809 (2025)
  • Spa: No
  • 3 Days off yellowkey (back on 4/6/2026 )
  • Garage Spaces:1 ()
  • Square Feet: 2665
  • Fees: $150 Monthly
  • Sarasota County
  • Terms: Cash, Conventional, FHA, VA Loan
  • Subdivision Info:
  • Occupancy Information: Vacant
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  • Subdivision Name: TOWNS-END SHORES
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  • Interior Features: Ceiling Fans(s), Crown Molding, Eat-in Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, PrimaryBedroom Upstairs, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Tray Ceiling(s), Walk-In Closet(s), Window Treatments
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  • Carport Spaces: 1
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  • Parking Description: Oversized, Basement
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History:

DateListing TypeDays on yellowkeyMLS#EventPrice% Chg$/sqftSource
4/6/2026Sale29A4684679Back on yellowkey$385,000-144.4652MLS
3/7/2026Sale0A4684679listed for sale$375,000-144.4652MLS




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