by Global Lifestyle Properties

See Home Value
$375,000
● House - Off Market

1795 HIGHLAND ROAD

OSPREY, FL 34229
bedrooms
3 Beds
bathrooms
3 Baths
square feet
1,879 Ft²
$2,275
Est. Monthly
$150
HOA / Fees

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.
Unit Size
1,879 Ft²
Days on Market
100 days
Land Size
0.08 acres
Price per sqft
$205
Property Type
House
Property Taxes
$234
HOA Dues
$150
Year Built
1999

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Last updated: 4 months ago (Stellar MLS #A4684679)

Price History

Date / Event Date Event Price
Jun 18, 2026 Sold
Sold
Apr 7, 2026 In contract -
In contract
Mar 26, 2026 Price Increased $385,000
↑ $10K (2.7%)
Price Increased
Mar 2, 2026 Listed by RE/MAX ALLIANCE GROUP $375,000
Listed by RE/MAX ALLIANCE GROUP
Oct 12, 2018 Sold
Sold
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Property Highlights

Garage
Air Conditioning

Building Info

Overview

    General

  • Year Built: 1999
  • Effective Year Built: 2009
  • Building Count: 1
  • Total Rooms: 9
  • Bedroom Count: 3
  • Bathroom Count: 3
  • Full Bathrooms: 3
  • Partial Bathrooms: 3
  • Bathroom Plumbing Fixtures: 2
  • Building Condition: 0
  • Building Quality: 9
  • Construction Type: 17
  • Building Style: 31
  • Exterior Walls Type: 19
  • Interior Walls Type: 3
  • Roof Shape Type: 8
  • Roof Cover Type: 5
  • Floor Count: 200
  • Living Units: 1
  • Floor Cover: 9
  • Basement Type: 0
  • Basement Area: 0
  • Garage Type: 1
  • Garage Square Area: 360
  • Parking Space Count: 1
  • Patio Type: 92
  • Porch Type: 111
  • Pool Type: 0
  • Location Influence Type: 125

    Dimensions

  • Lot Size Square Feet: 3,332
  • Lot Size Depth Feet: 10
  • Lot Size Frontage Feet: 10
  • Total Building Area: 2,239
  • Gross Building Area: 2,392
  • Building Area: 1,879
  • Building Area Measurement: L

    Heating and Cooling

  • Air Conditioning: 1
  • Heating: 3
  • Heated Square Feet: 1,879
  • Heating Fuel Type: 0

    Utilities

  • Sewer System: 1
  • Water Service: 2

Building

  • Building Type: 0
  • Property Class: R
  • Subdivision: TOWNS-END SHORES
  • Land Acres: 0000000077
  • Standard Land Use Code: 1001
  • County Land Use Code: 0101
  • State Land Use Code: 001
  • Legal Description 1: LOT 17, BLK A, LESS PORTION DESC AS BEG AT NW COR OF LOT 17 TH N-62-35-43-E 90.16 FT TH S-20-24-17-E 38.08 FT TH S-69-39-18-W 90.15 FT TH N-20-25-00-W 37.99 FT TO POB, TOWNS-END SHORES

Neighborhood

  • School District Name: Sarasota County School District
  • School Tax School District: A055 G054 W056
  • Census Tract: 002102

Zoning

  • Zoning: RMF2

Geography

  • Assessors Map Reference: 32D
  • Account Number: 0156120015
  • Subdivision Tract Number: 879
  • Parcel: 0156-12-0015
  • Block: A
  • Lot: 17
  • Meridian: SEC 14 TWN 38S RNG 18E
  • Municipality: SARASOTA COUNTY
  • Latitude: 27.1703
  • Longitude: -82.4789

    Address

  • Full Address: 1795 Highland Rd
  • Address - House Number: 1795
  • Address - Street Name: Highland
  • Address - Suffix Type: Rd
  • State: FL
  • City Name: Osprey
  • Carrier Code: R003
  • 4-Digit Zip Code: 9604
  • Zip Code: 34229

Valuation

    Tax

  • Total Area: 2,667
  • Tax Year: 2023
  • Tax Amount: $236,871
  • Tax Rate Code Area: 0100

    Appraisal Valuation

  • Standard Deviation: 0.1672
  • Valuation Date: Jan 10, 2024
  • Confidence Score: 78
  • Final Value: 421,148
  • High Value: 491,564
  • Low Value: 350,732

    Market Valuation

  • Market Total Value: $319,400
  • Market Land Value: $74,100
  • Market Improvement Value: $245,300

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $210,525

    Exemptions

  • Homeowner Exemption: Yes

    Sales

  • Current Sale Contract Date: Oct 11, 2018
  • Current Sale Recording Date: Oct 12, 2018
  • Current Sale Price:
  • Current Sale Document Type: 71
  • Current Sale Input Document Number: 2018135220
  • Previous Sale Recording Date: May 23, 2016
  • Previous Sale Contract Date: May 18, 2016
  • Previous Sale Amount: $217,000
  • Previous Sale Document Type: 71
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Towns-End Shores


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Frequently Asked Questions

When was property at 1795 Highland Road built and last sold?
The property at 1795 Highland Road was built in 1999 and last sold on Oct 11, 2018 for $248,000.
How much is this home worth?
The estimated value of the home located at 1795 Highland Road is $0.
What are some comparable homes to 1795 Highland Road?
There are currently no comparable homes to 1795 Highland Road.