Skip to content
Property for sale at 1795 HIGHLAND ROAD, OSPREY, FL, 34229

1795 Highland RoadOsprey, FL, 34229

3beds
3baths
1,879sqft
Single Family Residence
Built in 1999
$150 Monthly HOA Fee
$375,000
Sold
Price per sqft
$200
Sold on
Jun 18, 2026
MLS #A4684679Updated Jun 18, 2026

About this property

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.

Interested in this property?
Gaby, Property Specialist
Speak to GabyProperty Specialist, SerhantGaby can share what this home sold for, and find you comparable properties still on the market.
+1 (407) 490-0475
No pressure. Your details stay private.

Property details

Property type
Single Family Residence
Street address
1795 Highland Road
City
Osprey
State
FL
ZIP code
34229
Year built
1999
New construction
No
Attached property
Yes
Faces
Southwest
Rooms
10
Building stories
2
Living area
1,879 sqft
Total building area
2,665 sqft
Levels
Two

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at November 8, 2026 at 8:00 AM EST

Price & sale history

EventPrice
SoldMLS #A4684679$375,000
Price increasedMLS #A4684679$385,000Change: +2.7%+$10,000
Listed for saleMLS #A4684679$375,000
SoldMLS #A4408365$248,000
History may be incomplete.
Explore nearby sales

Location

Property for sale at 1795 HIGHLAND ROAD, OSPREY, FL, 34229
Learn more about this propertyGet in touch for more information
We will use your details to respond to this request and may share them with a suitable real estate professional when needed. Marketing is optional.