2159 Harbourside Dr, Longboat Key, FL 34228
OFF MARKET

2159 Harbourside Dr
Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 2,219 sqft

$973,200

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $6,047/mo*
Refinance Your Home

$973,200

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $6,047/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,219 sqft

Local Information

  • Map ViewExplore the area around 2159 Harbourside Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Condo
Year Built
1984
Living Area
2,219 sqft
Price/Sqft
$439
Parking
Garage

About this House

One of the prettiest villas in all of Harbour Oaks. This lovely three bedroom corner villa has a sunny west exposure with views of the island side golf course & lovely canopied trees. Many upgrades & features including an open kitchen with granite counters, white flat panel cabinets, upscale stainless appliances, cathedral ceilings & skylights, a new dual sink vanity, framed mirror & ceiling lights in the marble master bath plus all new air ducts & insulation. The living room has a corner marble fireplace shared with the family room, both with vaulted ceilings & ceilings fans. The formal dining room (furnished as den) has clerestory window & opens to an inner garden atrium creating another pretty setting to enjoy. The spacious master suite also has vaulted ceilings, seating area & three custom closets. The guest bedroom has a wall of custom closets & accesses an inner garden atrium. The third bedroom has built-in bookshelves & desk, currently doubling as an office/den. An exceptionally large open paver tiled garden patio offers an inviting newly resurfaced spa tub & electric retractable awnings to enjoy both shaded & sun filled days. There is a private two car garage with plenty of storage space. Harbour Oaks is located behind the private gates of Bay Isles & includes deeded beach access through the Beach Club. There is a community pool & spa, is pet friendly & is a wonderful place to call home. Turnkey designer furnishings per inventory are included.
2159 Harbourside Dr, Longboat Key, FL 34228 is a 3 bedroom, 3 bathroom, 2,219 sqft condo built in 1984. It last sold for $635,000 on Apr 11, 2017. It is currently off market. The Trulia Estimate is $973,200, with a rent estimate of $6,837/month.

Home Details for 2159 Harbourside Dr

Interior Features

Heating & Cooling
Heating: CentralAir ConditioningCooling System: CentralHeating Fuel: Central
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet
Interior Details
Number of Rooms: 7
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: StuccoFoundation Type: Concrete BlockPatio
Parking & Garage
GarageParking: Garage, Open

Property Information

Year Built
Year Built: 1984Year Updated: 1989
Property Type / Style
Property Type: Condo

Community

Units in Building: 1

Price History for 2159 Harbourside Dr

DatePriceEventSource
04/11/2017$635,000Sold
N/A
01/23/2017$679,000PendingAgent Provided
08/31/2016$679,000PriceChange
Agent Provided
05/27/2016$699,000Listed For SaleAgent Provided
02/26/2010$501,000Sold
N/A
05/13/2005$700,000Sold
N/A

Market trends in Longboat Key

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.04M
$23.5KMoM
Sale-to-List Price
93.7%
0.1%MoM
Price per sq ft
$651
$11MoM
Available listings
370
50MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$11,082
Assessment$845,300
Home facts updated by county records

Comparable Sales for 2159 Harbourside Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2181 HARBOURSIDE DRIVE #1403, Longboat Key, FL
0.00
Condo
$740,000
07/31/26
3
2.5
2,219
2141 HARBOURSIDE DRIVE #1203, Longboat Key, FL
0.00
Condo
$525,000
08/30/25
3
3
2,219
2155 HARBOURSIDE DRIVE #804, Longboat Key, FL
0.00
Condo
$740,000
04/28/26
3
2
2,119
2155 Harbourside Dr #8-804, Longboat Key, FL
0.00
Condo
$740,000
04/28/26
3
2
1,906
2321 Harbour Oaks Dr, Longboat Key, FL
0.16
Condo
$634,674
06/05/26
3
3
2,478
2195 HARBOURSIDE DRIVE #404, Longboat Key, FL
0.00
Condo
$850,000
04/09/26
3
2
1,906
2123 Harbourside Dr #9-903, Longboat Key, FL
0.00
Condo
$1,200,000
04/07/26
3
3
2,224
2103 Harbourside Dr, Longboat Key, FL
0.00
Condo
$1,100,000
10/06/25
3
2.5
2,448
2123 HARBOURSIDE DRIVE #903, Longboat Key, FL
0.00
Condo
$1,200,000
04/03/26
3
3
2,352
2120 HARBOURSIDE DRIVE #612, Longboat Key, FL
0.21
Condo
$655,000
03/06/26
3
2
2,039

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 2159 Harbourside Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Longboat Key

At least 28 Trulia users voted on each feature.

  • 91 % Say it's quiet

  • 88 % Say car is needed

  • 85 % Say it's dog friendly

  • 84 % Say parking is easy

  • 81 % Say people would walk alone at night

  • 79 % Say they plan to stay for at least 5 years

  • 63 % Say there are sidewalks

  • 55 % Say streets are well-lit

  • 47 % Say neighbors are friendly

  • 47 % Say it's walkable to grocery stores

  • 46 % Say it's walkable to restaurants

  • 46 % Say there's holiday spirit

  • 46 % Say there are community events

  • 45 % Say there's wildlife

  • 43 % Say yards are well-kept

  • 24 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.
  • Gabriel Rodriguez
    "Quiet beach town that is a gem and well kept secret. We love to visit for the past 23 years and are planning to retire here. "
    0
    Flag
  • Dougtibbetts
    "My neighborhood is full of amenities. 27 holes of golf, 20 tennis courts, 8 -pickle ball courts, marina,restaurants, banks, pharmacy post office all within easy walking distance "
    1
    Flag
  • Trulia User
    "We have monthly concerts at our Town Center during season. We also have small town 4th of July and Christmas parades"
    0
    Flag
  • Jonettesullivan
    "Dogs are plentiful and welcomed up to 50lbs. Over half of the residents in the neighborhood have a pet. "
    0
    Flag
  • Dougtibbetts
    "Safe area with many amenities like tennis, golf, boating.. Publix, CVS, banking, post office and many restaurants in the area. St Armand’s is nearby"
    0
    Flag
  • Dogwooddesigns2
    "O It is a barrier island on the Gulf of Mexico, close to the sophisticated city of Sarasota for fine dining and the arts. "
    0
    Flag
  • Jeffrey D Carman
    "It is an Old Fishing Village and still has a quaint charm to it with Full time, part time, and short term renters inhabiting this neighborhood, with LOTS of Dogs and Peacocks."
    4
    Flag
  • Skisundance
    "A small condo community with very few renters. Owners are very friendly, but also allow you to have your own space. The pool is rarely used. Spring break sees more visitors, so that is the busiest time. You can walk for miles on the beach - or pop across the street for shopping and at least 3 restaurants."
    4
    Flag
  • Lawrence b.
    "I'm on vacation here. I plan to come here every year to the same place. We have a wonderful view of the Gulf."
    0
    Flag
  • Kristonlamb
    "We are a community of neighbors that regularly interact and look out for one another. We walk our dogs to the bay for sunrise, and ride our bikes to the beach at sunset."
    1
    Flag
  • tom_sweet
    "Beautiful place. It's only 5 minutes from St. Armands Circle where there are great restaurants and shops. "
    0
    Flag
  • tom_sweet
    "Only 5 minutes away from the restaurants in St. Armands Circle and Sarasota makes it so convenient to go out. "
    0
    Flag
  • Janet M.
    "Great place to live, a short stroll to either the gulf to swim or the pool to swim. If you have a boat, great place to dock it and enjoy the inner coastal waterway. "
    1
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

12 pet-friendly rentals in Longboat Key, FL

Explore by feature - Garage

46 rentals with a garage in Longboat Key, FL

Explore by feature - Air Conditioning

137 rentals with air conditioning in Longboat Key, FL

Explore by feature - Pool

136 rentals with a pool in Longboat Key, FL

Explore by feature - Washer/dryer

136 rentals with a washer/dryer in Longboat Key, FL

Explore by feature - Outdoor Space

9 rentals with an outdoor space in Longboat Key, FL

Homes for sale near 2159 Harbourside Dr

Skip to last item
Skip to first item

Off Market Homes Near 2159 Harbourside Dr

Skip to last item
Skip to first item

Frequently asked questions about 2159 Harbourside Dr

  • What is 2159 Harbourside Dr estimated to be worth?
    Trulia's estimated value for 2159 Harbourside Dr in Longboat Key, FL is $973,200.
  • What is the price history for 2159 Harbourside Dr?
    2159 Harbourside Dr in Longboat Key, FL last sold for $635,000 in April 2017.
  • Is Longboat Key a buyer's or seller's market?
    Longboat Key is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Longboat Key?
    The median sale price in Longboat Key is $1.04M. That is down $23.5K from the prior month.
  • Does 2159 Harbourside Dr have air conditioning?
    Yes, 2159 Harbourside Dr in Longboat Key, FL has air conditioning.