1795 HIGHLAND ROAD, Osprey, FL, 34229 | $385,000

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.

Features

  • Amenities: Playground, Pool
  • Rooms: 10
  • Bedrooms: 3
  • Baths: 3 full
  • Laundry: Laundry Room
  • Style: Florida
  • Year Built: 1999
  • Garage: 1-car Oversized, Under Building
  • Heating: Central, Electric
  • Cooling: Central Air
  • Approx Sq. Feet: 1,879
  • Acreage: 0.08
  • Est. Taxes: $2,809
  • HOA Fee: $150 Monthly
  • Lot Desc: In County
  • Elem. School: Laurel Nokomis Elementary
  • Middle School: Sarasota Middle
  • High School: Venice Senior High
  • Pet Policy: Yes
  • Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • MLS#: A4684679
  • Days on Market: 15 days
  • Website: https://www.raveis.com
    /prop/A4684679/1795highlandroad_osprey_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. (last updated 3/31/2026 1:47:07 PM)
Listing courtesy of RE/MAX ALLIANCE GROUP   Phone: 941-954-5454

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Melissa CohnRVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 16953

917.838.7300

Melissa.Cohn@raveis.com

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1795 HIGHLAND ROAD, Osprey, FL, 34229

$385,000

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Melissa Cohn

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 917.838.7300

Melissa.Cohn@raveis.com

NMLS Mortgage Loan Originator ID 16953

5/6 (30 Yr)
Adjustable Rate Conforming*
30 Year
Fixed-Rate Conforming
15 Year
Fixed-Rate Conforming
Loan Amount $308,000 $308,000 $308,000
Term 360 months 360 months 180 months
Initial Interest Rate** 6.000% 6.375% 5.625%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.395% 6.557% 5.990%
Monthly Tax Payment $234 $234 $234
H/O Insurance Payment $75 $75 $75
Initial Principal & Interest Pmt $1,847 $1,922 $2,537
Total Monthly Payment $2,156 $2,231 $2,846

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.  The Total Monthly Payment does not include the estimated HOA/Common Charge payment.