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$529,000

1990 Main St

Sarasota, FL
Pending
2
Bedrooms
2
Bathrooms
1,747
Square Feet
0.55
Lot Size (acres)
2005
Year Built
61
Days On Market

Experience a distinctive downtown lifestyle from this rare two-story penthouse residence at Cityscape at Courthouse Centre. Offering two bedrooms, two baths, secure building access, elevator service, assigned under-building parking and a thoughtfully designed multi-level floor plan, this unique residence combines the character of an urban loft with the comfort and privacy of a traditional home. Exposed ductwork adds an industrial-chic aesthetic, while the private balcony offers city views and the ideal place to enjoy your morning coffee or unwind at the end of the day. The separation between the living areas and private bedroom level creates an ideal balance for everyday living, entertaining and hosting overnight guests. Ideally positioned above Main Street, you'll find yourself immersed in the energy of downtown Sarasota, where award-winning restaurants, sidewalk cafés, artisan coffee shops, boutiques, theaters, galleries, fitness studios and everyday conveniences are all near your front door. Whether enjoying a morning walk along Sarasota Bay, an evening performance at the Sarasota Opera House, cocktails overlooking the marina, or one of the city's many art festivals and cultural events, this location places the best of Sarasota within easy reach. Bayfront Park, Marina Jack, Marie Selby Botanical Gardens, Lido Beach, and the renowned shopping and dining of St. Armands Circle are all just minutes away. Thoughtfully maintained and ready for its next chapter, the residence offers timeless potential for personalization while preserving the distinctive architectural appeal of this rarely available floor plan. The air conditioning system was replaced in 2023, providing added peace of mind, while both bedrooms feature convenient motorized window shades for enhanced comfort and privacy. Whether you're seeking a full-time residence, a seasonal escape, or an elegant lock-and-leave retreat, this penthouse delivers an exceptional combination of location, style, comfort and value in the heart of one of Florida's desirable downtown destinations. Opportunities to own a two-story penthouse in Cityscape at Courthouse Centre are few and far between. Discover the possibilities, embrace Sarasota's vibrant urban lifestyle and make this exceptional residence your own.

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Listing Information

Listing Updated
24 days ago
Listed By
Chris Constantinou, 8602270044 · PREMIER SOTHEBY'S INTERNATIONAL REALTY, 9419079541
MLS#
A4701573
Source
Stellar MLS
Status
Pending

Facts & Features

Location

Community Information

Address
1990 Main St #4, Sarasota, FL 34236
City
Sarasota
County
Sarasota
Neighborhood
CITYSCAPE AT COURTHOUSE CENTRE
Zip Code
34236

Architecture

Bedrooms
2
Bathrooms
2
Stories
9
Year Built
2005
Construction Materials
Stucco
Building Area
1,747 sq. ft.
Roof
Concrete
Levels
Two
Garage
Yes
Garage Spaces
1
Parking Features
Covered, Basement, Assigned

Features & Amenities

Interior Features
Elevator, High Ceilings, Stone Counters
Appliances
Dryer, Microwave, Refrigerator, Washer, Range
Flooring
Tile, Carpet, Wood
Exterior Features
Storage, Balcony
Patio and Porch
Covered, Rear Porch
Community Features
Restaurant
Cooling
Central Air
Heating
Electric

Property Features

Lot Size
0.55 Acres
View
City
Water
Public
Sewer
Public Sewer
Utilities
Cable Available, Cable Connected, Electricity Connected, Sewer Connected, Water Connected

Square Footage

Total
1,453 sq. ft.

Tax & Financial Information

List Price
$529,000
Annual Taxes
$6,766
Fee Includes
Trash, Maintenance Grounds, Maintenance Structure, Water, Sewer, Security
Association Amenities
Maintenance, Other, Cable TV

Schools

76/100
Sarasota High School
High · Grades 09–12 · 0.9 mi
City
Sarasota
Students
2,509
Parent reviews
5.0★ avg · 2 reviews
Student body
56% White · 31% Hispanic / Latino · 6% Black
Free/reduced lunch
43%
Phone
(941) 955-0181
75/100
Bay Haven School Of Basics Plus
Elementary · Grades KG–05 · 2.2 mi
City
Sarasota
Students
582
Parent reviews
5.0★ avg · 4 reviews
Student body
49% White · 23% Hispanic / Latino · 19% Black
Free/reduced lunch
49%
Phone
(941) 359-5800
74/100
Emma E. Booker Elementary School
Elementary · Grades PK–05 · 1.6 mi
City
Sarasota
Students
516
Parent reviews
5.0★ avg · 2 reviews
Student body
55% Black · 25% Hispanic / Latino · 10% White
Free/reduced lunch
90%
Phone
(941) 361-6480
67/100
Booker Middle School
Middle · Grades 06–08 · 2.2 mi
City
Sarasota
Students
950
Parent reviews
4.0★ avg · 2 reviews
Student body
50% Hispanic / Latino · 25% Black · 19% White
Free/reduced lunch
76%
Phone
(941) 359-5824
63/100
Southside Elementary School
Elementary · Grades KG–05 · 1.9 mi
City
Sarasota
Students
729
Parent reviews
3.7★ avg · 6 reviews
Student body
78% White · 13% Hispanic / Latino · 6% Two or More Races
Free/reduced lunch
26%
Phone
(941) 361-6420
58/100
Booker High School
High · Grades 09–12 · 2 mi
City
Sarasota
Students
1,207
Parent reviews
3.0★ avg · 4 reviews
Student body
33% Hispanic / Latino · 32% White · 29% Black
Free/reduced lunch
62%
Phone
(941) 355-2967
57/100
Tuttle Elementary School
Elementary · Grades PK–05 · 1.3 mi
City
Sarasota
Students
735
Parent reviews
3.0★ avg · 8 reviews
Student body
65% Hispanic / Latino · 14% White · 14% Black
Free/reduced lunch
91%
Phone
(941) 361-6433
57/100
Sarasota County Acceleration Academies
High · Grades 09–12 · 2.1 mi
City
Sarasota
Students
145
Student body
46% White · 30% Hispanic / Latino · 17% Black
Free/reduced lunch
3%
Phone
(941) 315-2122

School ratings are provided for informational purposes only and are subject to change. Attendance boundaries are for reference only — contact the school or district directly to verify enrollment eligibility.

Historical Data

Price History

DateEventPrice
08/20/2026Price change$529,000
08/03/2026Listed for sale$547,500

Listed by Chris Constantinou · PREMIER SOTHEBY'S INTERNATIONAL REALTY · 9419079541

Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. Copyright 2026, Stellar MLS. All rights reserved.

Last Updated: September 9, 2026 at 3:42 PM | Source: Stellar MLS | MLS#: A4701573

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