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Sold for $375,000
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    • $375,000

    1795 Highland Rd, Osprey, FL 34229

    3beds
    1,879sqft
    Single Family Residence
    Built in 1999
    3,332 Square Feet Lot
    $375,000 Zestimate®
    $200/sqft
    $3,881 Estimated rent

    Home value

    $375,000

    $345,000 - $409,000

    $3,881/mo

    Zestimate® history
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    What's special

    Air-conditioned garagePrivate kayak launchUnique two-level layoutWood flooringTray ceilingsCrown molding
    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.

    Zillow last checked:

    Listing updated:

    Listed by:

    Rachel Tritschler 941-993-5892,

    RE/MAX ALLIANCE GROUP 941-954-5454,

    Rick Tritschler, Jr. 941-928-1292,

    RE/MAX ALLIANCE GROUP

    Bought with:

    McKenzie Weirich, 3450987

    THE SHORELINE FL REALTY LLC

    Source: Stellar MLS,MLS#: A4684679MLS LogoOriginating MLS: Sarasota - Manatee

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 3
    • Bathrooms: 3
    • Full bathrooms: 3
    Primary bedroom
    • Features: En Suite Bathroom, Walk-In Closet(s)
    • Level: Second
    • Area: 228 Square Feet
    • Dimensions: 19x12
    Bedroom 2
    • Features: En Suite Bathroom, Built-in Closet
    • Level: Second
    • Area: 140 Square Feet
    • Dimensions: 14x10
    Bathroom 3
    • Level: First
    Bathroom 3
    • Features: Built-in Closet
    • Level: First
    Balcony porch lanai
    • Level: Second
    • Area: 133 Square Feet
    • Dimensions: 19x7
    Dinette
    • Level: Second
    • Area: 49 Square Feet
    • Dimensions: 7x7
    Kitchen
    • Level: First
    Kitchen
    • Features: Granite Counters
    • Level: Second
    • Area: 110 Square Feet
    • Dimensions: 10x11
    Living room
    • Level: First
    Living room
    • Features: Ceiling Fan(s)
    • Level: Second
    • Area: 391 Square Feet
    • Dimensions: 23x17
    Heating
    • Central, Electric
    Cooling
    • Central Air
    Appliances
    • Included: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
    • Laundry: Laundry Room
    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)
    • Flooring: Carpet, Ceramic Tile, Hardwood
    • Doors: Outdoor Kitchen, Sliding Doors
    • Windows: Window Treatments
    • Basement: Other
    • Has fireplace: No
    Interior area
    • Total structure area: 2,665
    • Total interior livable area: 1,879 sqft

    Property

    Parking
    • Total spaces: 2
    • Parking features: Oversized, Under Building
    • Attached garage spaces: 1
    • Carport spaces: 1
    • Covered spaces: 2
    • Details: Garage Dimensions: 11x30
    Features
    • Levels: Two
    • Stories: 2
    • Patio & porch: Covered, Patio, Porch, Screened
    • Exterior features: Balcony, Lighting, Outdoor Kitchen, Private Mailbox, Rain Gutters
    • Fencing: Wood
    Lot
    • Size: 3,332 Square Feet
    • Features: In County
    • Residential vegetation: Mature Landscaping, Trees/Landscaped
    Details
    • Additional structures: Outdoor Kitchen
    • Parcel number: 0156120015
    • Zoning: RMF2
    • Special conditions: None

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Florida
    • Property subtype: Single Family Residence
    • Attached to another structure: Yes
    Materials
    • Vinyl Siding
    • Foundation: Pillar/Post/Pier
    • Roof: Metal
    Condition
    • New construction: No
    • Year built: 1999

    Utilities & green energy

    • Sewer: Public Sewer
    • Water: Public
    • Utilities for property: BB/HS Internet Available, Cable Available, Electricity Connected, Public, Sewer Connected, Water Connected

    Community & HOA

    Community
    • Features: Water Access, Pool
    • Pet fee: $0 monthly
    • Subdivision: TOWNS-END SHORES
    HOA
    • Has HOA: Yes
    • Amenities included: Playground, Pool
    • Services included: Community Pool, Maintenance Grounds, Maintenance Repairs, Pest Control, Pool Maintenance
    • HOA fee: $150 monthly
    • HOA name: Colleen Donlevy
    • HOA phone: 407-325-2873
    Location
    • Region: Osprey

    Financial & listing details

    • Price per square foot: $200/sqft
    • Tax assessed value: $307,900
    • Annual tax amount: $2,808
    • Date on market: 3/10/2026
    • Cumulative days on market: 24 days
    • Listing terms: Cash,Conventional,FHA,VA Loan
    • Ownership: Fee Simple
    • Total actual rent: 18000
    • Electric utility on property: Yes
    • Road surface type: Paved, Asphalt

    Price history

    DateEventPrice
    6/18/2026Sold$375,000-2.6%$200/sqft
    Source: Stellar MLS #A4684679 Report a problem
    4/6/2026Pending sale$385,000$205/sqft
    Source: Stellar MLS #A4684679 Report a problem
    3/25/2026Price change$385,000+2.7%$205/sqft
    Source: Stellar MLS #A4684679 Report a problem
    3/10/2026Listed for sale$375,000+51.2%$200/sqft
    Source: Stellar MLS #A4684679 Report a problem
    12/27/2025Listing removed$1,500$1/sqft
    Source: Zillow Rentals Report a problem
    12/12/2025Price change$1,500-6.3%$1/sqft
    Source: Zillow Rentals Report a problem
    11/28/2025Listed for rent$1,600+14.3%$1/sqft
    Source: Zillow Rentals Report a problem
    7/3/2025Listing removed$1,400$1/sqft
    Source: Zillow Rentals Report a problem
    6/21/2025Listed for rent$1,400$1/sqft
    Source: Zillow Rentals Report a problem
    4/5/2025Listing removed$1,400$1/sqft
    Source: Zillow Rentals Report a problem
    3/17/2025Price change$1,400-6.7%$1/sqft
    Source: Zillow Rentals Report a problem
    3/13/2025Price change$1,500+15.4%$1/sqft
    Source: Zillow Rentals Report a problem
    3/12/2025Listed for rent$1,300$1/sqft
    Source: Zillow Rentals Report a problem
    10/12/2018Sold$248,000-3.9%$132/sqft
    Source: Public Record Report a problem
    9/15/2018Pending sale$258,000$137/sqft
    Source: Keller Williams Realty Select #A4408365 Report a problem
    6/17/2018Listed for sale$258,000+18.9%$137/sqft
    Source: Owner Report a problem
    5/23/2016Sold$217,000+65.6%$115/sqft
    Source: Public Record Report a problem
    5/23/2002Sold$131,000-0.8%$70/sqft
    Source: Public Record Report a problem
    12/30/1999Sold$132,000$70/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$2,809 +13.9%$223,129 +2.9%
    2024$2,465 +4.1%$216,841 +3%
    2023$2,369 +3%$210,525 +3%
    2022$2,299 +0.5%$204,393 +3%
    2021$2,288 +0%$198,440 +1.4%
    2020$2,288 +4.3%$195,700 +2.3%
    2019$2,194 $191,300 +7.3%
    2018$2,194 +9.1%$178,267 +2.1%
    2017$2,011 +492.6%$174,600 -0.7%
    2016$339 $175,900 +16.9%
    2015$339 $150,500 +34.8%
    2014$339 -71.9%$111,665
    2013$1,207 +3.2%$111,665 +1.7%
    2012$1,170 +5.3%$109,798 +3%
    2011$1,111 -7.8%$106,600 -4.4%
    2010$1,205 -45.6%$111,500 -19.3%
    2009$2,212 $138,100 -30.2%
    2008$2,212 -22.2%$197,900 -16.1%
    2007$2,843 $235,900 -5%
    2006-- $248,400 +30.2%
    2005-- $190,800 +10.5%
    2004$2,752 -2.8%$172,600 +0.2%
    2003$2,831 +28.3%$172,300 +33.8%
    2002$2,207 +12.2%$128,800 +7.9%
    2001$1,968 +4.9%$119,400 +7.3%
    2000$1,875 $111,300
    Find assessor info on the county website

    Neighborhood: 34229

    Nearby homes

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: Laurel Nokomis Elementary
    • Middle: Sarasota Middle
    • High: Venice Senior High

    Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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    Estimated market value
    $375,000
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    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $375,000

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