1795 Highland Rd

Osprey, FL 34229

$385,000
Price
3
Beds
1,879 Sq. Ft.
$205 / Sq. Ft.
1,879
Sq. Ft.
$205
per Sq. Ft.
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a living room with furniture and a large window
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a kitchen with stainless steel appliances granite countertop a stove a sink a refrigerator white cabinets and wooden floor next to a window
a kitchen with stainless steel appliances granite countertop a stove top oven a sink a dining table and chairs with wooden floor
a view of a dining room with furniture and wooden floor
a kitchen with stainless steel appliances white cabinets and a stove top oven
a bedroom with a bed and a window
a bathroom with a granite countertop sink a mirror and a shower
a bathroom with a shower
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Description

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...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.
  1. Listed by Rachel Tritschler • Brokerage DRE #1030924 • RE/MAX ALLIANCE GROUP
    P: (941)-993-5892 C: (941)-993-5892 Rachel@teamtritschler.com
  2. Listed by Rick Tritschler, Jr. • Brokerage DRE #1030924 • RE/MAX ALLIANCE GROUP
    P: (941)-928-1292 C: (941)-928-1292 Rick@teamtritschler.com

Property Details for 1795 Highland Road

Architectural Style
Florida
Subdivision Name
TOWNS-END SHORES
Township
38
Carport Spaces
1
Garage Spaces
1
Waterfront
No
Furnished
Negotiable
LISTING UPDATED: 03/25/2026 06:41 PM

Property Details for 1795 Highland Road

StatusActive
MLS #A4684679
Days on Market20
Taxes$2,809 / year
HOA Fees$1,800 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1999
Lot Size0.08 AC / 3,332 SF
CountySarasota County
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Location

Listing Courtesy of RE/MAX ALLIANCE GROUP, Rachel Tritschler; RE/MAX ALLIANCE GROUP, Rick Tritschler, Jr.
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Building Information for 1795 Highland Road

Stories2Year Built1999Building Size-Lot Size0.08 AC / 3,332 SF

Payment Calculator

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$2,253 per month

30 year fixed, 6.11% Interest

Principal and Interest

$1,868

Property Taxes

$234

HOA Dues

$150

The Payment Calculator is for illustrative purposes only.

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Property Information for 1795 Highland Road

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 2665.0
  • Building Area Units: Square Feet
  • Building Name Number: TOWNS-END SHORES
  • Community Features: Water Access, Pool
  • Direction Faces: Southwest
  • Directions: From US41 turn west onto North Lane then turn left onto Highland Road. The home will be on the left.
  • Elementary School: Laurel Nokomis Elementary
  • Middle Or Junior School: Sarasota Middle
  • High School: Venice Senior High
  • Mls Major Change Type: Price Increase
  • Listing Service: Full Service
  • Road Frontage Type: Street Paved
  • Senior Community: No
  • SW Subdiv Community Name: Towns-End Shores
  • Unit Number: No
  • Street Number: 1795
  • Street Name: HIGHLAND
  • Street Suffix: ROAD
  • State: FL
  • City: OSPREY
Parking
  • Attached Garage: Yes
  • Carport: Yes
  • Garage Dimensions: 11x30
  • Garage: Yes
  • Parking Features: Oversized, Under Building
Taxes and HOA Information
  • Association Approval Required: No
  • Association Fee Includes: Community Pool, Maintenance Grounds, Maintenance Repairs, Pest Control, Pool Maintenance
  • Association Fee Requirement: Required
  • Association Name: Colleen Donlevy
  • Association Phone: (407) 325-2873
  • Association: Yes
  • CDD: No
  • Pet Restrictions: Buyer and Buyer's agent to verify with association.
  • Tax Block: A
  • Tax Book Number: 5-28
  • Tax Legal Description: 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
  • Tax Lot: 17
  • Tax Year: 2025
Property
Lot Information
  • Additional Parcels: No
  • Lot Features: In County
  • Parcel Number: 0156120015
  • Total Acreage: 0 to less than 1/4
  • Water Access: No
  • Water Extras: No
  • Zoning: RMF2
  • Living Area: 1879
  • ILS Total SQFT: 679.0
  • ILS Under Air SQFT: 679.0
Property and Assessments
  • Year Built Numeric: 1999
  • Association Amenities: Playground, Pool
  • Flood Zone Code: X
  • Homestead: Yes
  • New Construction: No
  • Property Attached: Yes
  • Public Survey Range: 18
  • Public Survey Section: 14
  • Dock YN: No
Utilities
  • Sewer: Public Sewer
  • Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Public, Sewer Connected, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Vinyl Siding
  • Exterior Features: Balcony, Lighting, Outdoor Kitchen, Private Mailbox, Rain Gutters, Sliding Doors
  • Fencing: Wood
  • Foundation Details: Pillar/Post/Pier
  • Levels: Two
  • Other Structures: Outdoor Kitchen
  • Patio And Porch Features: Covered, Patio, Porch, Screened
  • Pool Private: No
  • Pool: Community
  • Pool Private: Yes
  • Roof: Metal
  • Spa: No
  • Vegetation: Mature Landscaping, Trees/Landscaped
  • Waterfront Feet Total: 0
  • Number Of Stories: 2
Interior Features
  • Bedrooms Total: 3
  • Bathrooms Full: 3
  • Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • Cooling: Central Air
  • Fireplace: No
  • Flooring: Carpet, Ceramic Tile, Hardwood
  • Heating: Central, Electric
  • Interior Features: Ceiling Fan(s), Crown Molding, Eating Space 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
  • Laundry Features: Laundry Room
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 10.0
  • Water View: No
  • Bathrooms Half: 0
Rental
Rental Information
  • Currency Monthly Rent Amt: $1,500.00
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 1795 Highland Road

DateEvent & SourcePriceAppreciation
Mar 25, 2026

Price Change

MFRMLS #A4684679

$385,000—
Mar 10, 2026

Listed (Active)

MFRMLS #A4684679

$375,000—
Oct 12, 2018

Sold

MFRMLS #A4408365

$248,000—
Oct 11, 2018

Sold (Public Record)

Public Record #632643840

$248,000

+5.7% / yr

Sep 15, 2018

Pending

MFRMLS #A4408365

—
Jul 23, 2018

Listed (Active)

MFRMLS #A4408365

$258,000—
May 18, 2016

Sold (Public Record)

Public Record #570994126

$217,000—
DateEvent & SourcePrice
03/25/2026

Price Change

MFRMLS #A4684679

$385,000
03/10/2026

Listed (Active)

MFRMLS #A4684679

$375,000
10/12/2018

Sold

MFRMLS #A4408365

$248,000
10/11/2018

Sold (Public Record)

Public Record #632643840

$248,000

+5.7% / yr

09/15/2018

Pending

MFRMLS #A4408365

—
07/23/2018

Listed (Active)

MFRMLS #A4408365

$258,000
05/18/2016

Sold (Public Record)

Public Record #570994126

$217,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 1795 Highland Road

Taxable ValueLand-Additions-Total-
Tax Record2025$2,136 ($178 / month)
Home Facts
Baths2Total Finished SqFt1,187 SqFtAbove Grade Finished SqFt1,187 SqFtStories2Lot Size3,332 SqFtStyleDuplexYear Built1999Year Renovated2009ZoningRMF2CountySARASOTAAPN0156-12-0015

Schools near 1795 Highland Road

This home is within Sarasota.
Rating
School
Type
Grades
Distance
Laurel Nokomis School
Public - PK to 8
Venice Senior High School
Public - 9 to 12
Pine View School
Public - 2 to 12
Island Village Montessori School
Charter - K to 8
Rating
School
Distance
Laurel Nokomis School
PublicPK to 8

Venice Senior High School
Public9 to 12

Pine View School
Public2 to 12

Island Village Montessori School
CharterK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 1795 Highland Road, Osprey, FL 34229

1795 Highland Road is a single family home for sale in Osprey, FL 34229. This property was listed for sale on March 10, 2026 by RE/MAX ALLIANCE GROUP, it's currently listed at $385,000. It has been on the market for a total of 20 days and was last sold on October 12, 2018. This listing's school district is Sarasota. Nearby schools include Laurel Nokomis School, Venice Senior High School and Pine View School. 1795 Highland Road is a 3-bed, 3-bath, 1,879 sqft single family home built in 1999.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of RE/MAX ALLIANCE GROUP, Rachel Tritschler; RE/MAX ALLIANCE GROUP, Rick Tritschler, Jr.

The information is being provided in part by Southwest Florida Multiple Listing Service, Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2, and MarcoMls. Information deemed reliable but not guaranteed. Information is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2026 Southwest Florida Multiple Listing Service and MarcoMls. All Rights Reserved. The data relating to real estate for sale displayed on this website comes in part from the Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2 and MarcoMls. Properties listed with brokerage firms other than Compass are marked with the "BR House" logo. Detailed information about such properties includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties listed with brokerage firms participating in the Naples MLS BR Program, or contained in the database compilation of Naples MLS.