2020 HARBOURSIDE DRIVE UNIT 442 LONGBOAT KEY FL 34228 | MLS #A4705717

2020 HARBOURSIDE DRIVE UNIT 442
LONGBOAT KEY, FL, 34228
$699,000
2 Beds
2 Baths
1,192 SqFt
0 Acres
Add
MLS #A4705717 image #0
Enjoy direct Sarasota Bay views and deeded private beach access from this updated fourth-floor residence in Fairway Bay, an established gated Bay Isles community within the Longboat Key Club setting. Residence #442 at 2020 Harbourside Drive offers 1,312 square feet of bright, airy living space with two bedrooms and two bathrooms—an inviting coastal retreat where the bay becomes part of everyday life. Floor-to-ceiling views from the kitchen, dining area, and living room create a memorable backdrop for daily living and entertaining, while the private balcony is an ideal place to begin the day with a Sarasota Bay sunrise or settle in for the evening as the sky changes over the water. Keep watch for passing boats, coastal birds, and the occasional manatee in the bay below. The residence has been thoughtfully updated with a kitchen featuring granite countertops, a granite breakfast bar, stainless-steel appliances, and a newer microwave. A front-loading LG washer and dryer are included for everyday convenience. Ceramic tile flooring extends throughout the main living areas and guest spaces, while the primary bedroom features warm wood flooring. Fairway Bay offers a resort-inspired waterfront lifestyle with scenic walking paths, a heated swimming pool and spa, fitness facilities, social spaces, tennis courts, and paddle sports. Beyond the bayfront setting, owners enjoy deeded access to the Bay Isles Beach Club, providing a private connection to Longboat Key’s renowned Gulf beaches. It is the best of both waterfront worlds: tranquil Sarasota Bay just outside your door and the Gulf of Mexico’s white-sand shoreline close by. The community’s central island location makes it easy to walk or bike to nearby conveniences, including grocery shopping, pharmacy services, and tennis. For those who wish to expand their recreational options, membership opportunities may be available through the nearby Longboat Key Club, with its golf, tennis, dining, fitness, spa, and full-service deep-water marina amenities. St. Armands Circle is moments away for boutique shopping and acclaimed dining, while downtown Sarasota offers a vibrant extension of the island lifestyle with arts, culture, restaurants, and waterfront attractions. This is a rare opportunity to enjoy a beautifully updated fourth-floor bayfront residence where views, private beach access, resort-style amenities, and the effortless rhythm of Longboat Key living come together.

Property Details

Price:
$699,000
MLS #:
A4705717
Status:
Active
Beds:
2
Baths:
2
Type:
Condo
Subtype:
Condominium
Subdivision:
FAIRWAY BAY 2 PH 1
Neighborhood:
34228longboatkey
Listed Date:
Sep 17, 2026
Finished Sq Ft:
1,192
Total Sq Ft:
1,312
Year Built:
1984
WaterfrontCanalfrontPoolTennisCommunity GatedCommunity Club House34228 – Longboat Key34228longboatkeyFairway Bay 2 Ph 1Southside ElementaryBooker MiddleBooker HighSarasota Bay & Bay Isles CanalWaterSee Association Docs2 MonthsPets Allowed

Ask a Question

See this Listing

Send
  

Schools

Elementary School:
Southside Elementary
Middle School:
Booker Middle
High School:
Booker High

Interior

Appliances
Built-In Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Freezer, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Porcelain Tile
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Kitchen/Family Room Combo, Solid Surface Counters, Thermostat
Laundry Features
Laundry Closet
Levels
One

Exterior

Association Amenities
Clubhouse, Elevator(s), Fitness Center, Gated, Lobby Key Required, Pickleball Court(s), Pool, Recreation Facilities, Security, Tennis Court(s), Trail(s)
Attached Garage YN
1
Community Features
Bay/Harbor Front, Canal Front, Buyer Approval Required, Clubhouse, Fitness Center, Gated Community – Guard, Pool, Sidewalks, Tennis Court(s)
Construction Materials
Concrete, Stucco
Direction Faces
Southwest
Exterior Features
Balcony, Sidewalk, Sliding Doors
Open Parking YN
1
Parking Features
Circular Driveway, Common, Driveway, Ground Level, Guest, Off Street, Open
Roof
Built-Up, Concrete, Membrane
Security Features
Fire Sprinkler System, Gated Community, Security Gate, Smoke Detector(s)
View
Water
Waterfront Features
Bay/Harbor Front, Canal Front, Bay/Harbor
Window Features
Shades

Financial

HOA Fee
$1,379
HOA Fee 2
$1,379
HOA Fee 2 Frequency
Annually
HOA Fee Frequency
Annually
HOA Includes
24-Hour Guard, Common Area Taxes, Community Pool, Escrow Reserves Fund, Insurance, Maintenance Structure, Maintenance Grounds, Manager, Pool Maintenance, Private Road, Recreational Facilities, Security
HOA Name
Nat Veal
HOA Name 2
Bay Isles Master
HOA Phone
941-383-2701
Tax Year
2025
Taxes
$7,658

Map

Community

Subdivisions in LONGBOAT KEY

Market Summary

Current real estate data for Condo in LONGBOAT KEY as of Sep 17, 2026
164
Condo Listed
163
Avg DOM
728
Avg $ / SqFt
$1,251,875
Avg List Price

Property Summary

    Located in the FAIRWAY BAY 2 PH 1 subdivision, 2020 HARBOURSIDE DRIVE UNIT 442 LONGBOAT KEY FL is a Condo for sale in LONGBOAT KEY, FL, 34228. It is listed for $699,000 and features 2 beds, 2 baths, and has approximately 1,192 square feet of living space, and was originally constructed in 1984. The current price per square foot is $586. The average price per square foot for Condo listings in LONGBOAT KEY is $728. The average listing price for Condo in LONGBOAT KEY is $1,251,875. To schedule a showing of MLS#a4705717 at 2020 HARBOURSIDE DRIVE UNIT 442 in LONGBOAT KEY, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

Similar Listings Nearby

broker reciprocity
MLS# O6346773broker reciprocity
101 S GULFSTREAM AVENUE UNIT 10B
SARASOTA, FL

$899,999

4.6 miles away

broker reciprocity
MLS# A4694485broker reciprocity
100 CENTRAL AVENUE UNIT H716
SARASOTA, FL

$899,900

4.6 miles away

broker reciprocity
MLS# A4680085broker reciprocity
250 SANDS POINT ROAD UNIT 5203
LONGBOAT KEY, FL

$899,900

2.3 miles away

broker reciprocity
MLS# A4670726broker reciprocity
435 S GULFSTREAM AVENUE UNIT 1004
SARASOTA, FL

$895,000

4.8 miles away

broker reciprocity
MLS# A4686024broker reciprocity
3240 GULF OF MEXICO DRIVE UNIT B402
LONGBOAT KEY, FL

$880,000

1.6 miles away

broker reciprocity
MLS# A4670029broker reciprocity
1212 BENJAMIN FRANKLIN DRIVE UNIT 508
SARASOTA, FL

$875,000

4.4 miles away

2020 HARBOURSIDE DRIVE UNIT 442
LONGBOAT KEY, FL