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$1,395,000 Just Listed
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Property Description
Tucked just moments from Hudson Bayou and Sarasota Bay, this gated mid-century modern compound offers a rare opportunity to own a meaningful piece of Sarasota's architectural and artistic history while embracing a lifestyle that feels both inspired and entirely livable. Originally built in 1954 as a Ruth Richmond design and later reimagined by nationally recognized abstract artist Steve McCallum, the property blends authentic mid-century lines with bold creative character. Set behind walls and framed by lush tropical landscaping, the home unfolds as a private retreat within one of Sarasota's most desirable cultural corridors. A paver drive leads to the striking architectural facade, clerestory windows, and modern courtyard entry. Inside, natural light pours through high transom windows and expansive sliding glass doors, highlighting the openness and warmth that define true mid-century design. The main residence offers three bedrooms and two full baths, with an open living and dining layout that flows effortlessly to the courtyard pool. Clean lines, tile flooring throughout, and thoughtful updates create a space that feels timeless yet comfortable. The private courtyard pool anchors the compound, surrounded by palms, bamboo, and multiple seating areas designed for relaxed evenings or intimate gatherings. The setting offers privacy without sacrificing proximity to downtown and the bayfront. The studio structure truly elevates the estate. Measuring approximately 56 by 32 feet with soaring 16-foot ceilings, it was purpose-built for large-scale creative work and now offers remarkable flexibility. With its own private entrance and a dedicated bathroom, the studio can function independently as a guest retreat, executive workspace, gallery-style studio, or wellness space. An interior hallway also connects it to the main home, allowing seamless use for multigenerational living or extended guests while maintaining the option for complete privacy. For several years, the studio operated as a curated, owner-hosted guest experience, earning more than 200 five-star reviews and establishing itself among Sarasota's earliest luxury short-term stays. That history speaks to its design appeal, comfort, and versatility. Offering 2,278 square feet under air across both structures, this property delivers architectural authenticity, creative scale, and compound-style living just minutes from downtown dining, galleries, and Sarasota's renowned arts scene. This is a mid-century modern lifestyle property for those who value design, flexibility, and the freedom to shape a home around how they truly want to live. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Full Property Details
Full Property Details for 1939 High Point Dr
General
- Price: $1,395,000
- Taxes: $8,591 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: A4676860
- Updated: 2/26/2026
- Added to Site: 1 day(s) ago
Rental Information
- Min. Lease: 1 Week
Interior
- Number of Rooms: 9
- Interior Features: Built-in Features, Ceiling Fan(s), Window Treatments
- Appliances: Built-In Oven, Cooktop, Dryer, Microwave, Range, Refrigerator, Washer
- Furnishings: Unfurnished
- Flooring: Terrazzo, Tile
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Other
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Heated, In Ground, Salt Water
Exterior
- Exterior Features: French Doors, Lighting, Private Mailbox, Private Yard, Sliding Doors
- Deck/Patio: Patio
- Porch/Patio/Deck: Patio
Parking
- Parking Features: Driveway
Location
- Area: 34236 - Sarasota
- County: Sarasota
- Development Name: 34236 - Sarasota
- Subdivision: HIGH POINT CIRCLE
- Driving Directions: US 41 to West on High Point Dr, across from new modern museum/Old Sarasota High School.
- Direction Faces: Southwest
School Information
- Elementary School: Southside Elementary
- Middle School: Sarasota Middle
- High School: Sarasota High
Community
- Community Name: 34236 - Sarasota
Heating & Cooling
- Cooling Type: Central Air, Mini-Split Unit(s)
- Heating Type: Central, Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Available, Public, Sewer Available, Water Available
Structural Information
- Architectural Info: Mid-Century Modern
- Architectural Style: Mid-Century Modern
- Exterior Const.: Block, Stucco
- Roof: Shingle
- Windows: Window Treatments
- Stories/Levels: One
- Square Feet: 2,278
- Sq. Ft. Source: Public Records
- Year Built: 1954
Lot Features
- Lot Size (Acres): 0.23
- Lot Size (Sq. Ft.): 10,048
- Lot Size: 10048
- Frontage: Street Paved
- Street/Road Desc.: Paved
- Fencing (Description): Masonry
Financial Considerations
- Tax Amount: $8,591.51
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: LOT 22 HIGH POINT CIRCLE
- Flood Zone Info: X500*
- APN: 2036090049
- Property ID: 2036090049
Listed by Kw Coastal Living Iii
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Schools
Schools serving 1939 High Point Dr
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Southside Elementary School, Sarasota, FL 1901 Webber Street, Sarasota, FL 34239 | PK-5 | 1.2 mi |
Brookside Middle School 3636 South Shade Avenue, Sarasota, FL 34239 | 6-8 | 1.8 mi |
Sarasota High School 2155 Bahia Vista Street, Sarasota, FL 34239 | 9-12 | 0.3 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1939 High Point Dr
Date
Details
Price
Change
Source
2/26/2026
Listed
$1,395,000
207.07%
MLS
1/28/2015
Sold
$454,300
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 1939 High Point Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$8,004
12%
$606,896
23%
2024
$7,141
3%
$491,465
3%
2023
$6,918
3%
$477,150
6%
2021
$6,687
—
$449,759
-3%
2022
$6,713
—
$463,252
5%
2021
$6,687
-2%
$439,900
-2%
2019
$6,853
2%
$450,704
2%
2018
$6,738
-3%
$442,300
-2%
2017
$6,954
-5%
$451,600
5%
2016
$7,335
84%
$429,100
66%
2015
$3,985
—
$258,047
1%
2014
$3,977
—
$255,999
1%
2013
$3,965
—
$252,216
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 1939 High Point Dr
1939 High Point Drive, Sarasota, FL 34236 (MLS# A4676860) is a Single Family property with 3 bedrooms and 3 full bathrooms. 1939 High Point Drive is currently listed for $1,395,000 and was received on February 26, 2026. Want to learn more about 1939 High Point Drive? Do you have questions about finding other Single Family real estate for sale in Sarasota? You can browse all Sarasota real estate or contact a Coldwell Banker agent to request more information.

