Back 1795 Highland Rd
Off Market

1795 Highland Rd

Osprey FL 34229

3
3
2
2665 sq. ft.
3332 sq. ft.
Single-Family
Last sold for $375,000
Rachel TritschlerRachel Tritschler, last sold this property on 18 June 2026 after 99 days on market.

Overview

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

3 bedrooms
3 bathrooms
2 carspaces
1 carport space
1 garage space
2665 sq. ft. floor area
3332 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Osprey over the last 12 months, the estimated median property value of 1795 Highland Rd is $660k.

Median value
$660k
Estimated value range
$200k - $4.04m
Median days on market
32
Estimated value trend
-11%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Osprey. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 1795 Highland Rd

2026
Sold
$375,000
18 Jun 2026 by Rachel Tritschler, of REMAX Alliance Group | Riverview
2018
Sold
$248,000
12 Oct 2018 by Jamie Foster, of Keller Williams Realty Select

Happy sellers in Osprey

<50%
Less than 50% of sellers in Osprey reported that their sale price either exceeded or met their price expectations.

Osprey stands out as a desirable suburb for sellers, consistently delivering great customer service and strong market results for homeowners.

This is based on voluntary sentiment collected from 11 reviews in Osprey over the last 12 months.

Local market activity for 3 bedroom single-family properties in Osprey

In the last 12 months, 63 three-bedroom single-family properties similar to 1795 Highland Rd, have been sold.

This represents a 18% increase in three-bedroom single-family properties sales when compared to the previous 12 months.

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