Is Longboat Key, FL quiet?

As of early 2026, 91% of users say it's quiet

Is a car needed in Longboat Key, FL?

As of early 2026, 88% of users say car is needed

Is Longboat Key, FL dog-friendly?

As of early 2026, 85% of users say it's dog friendly

Is parking easy in Longboat Key, FL?

As of early 2026, 84% of users say parking is easy

Would people walk alone at night in Longboat Key, FL?

As of early 2026, 81% of users say people would walk alone at night

Do residents of Longboat Key, FL plan to stay at least 5 years?

As of early 2026, 79% of users say they plan to stay for at least 5 years

Does Longboat Key, FL have sidewalks?

As of early 2026, 63% of users say there are sidewalks

Are the streets well-lit in Longboat Key, FL?

As of early 2026, 55% of users say streets are well-lit

Are neighbors friendly in Longboat Key, FL?

As of early 2026, 47% of users say neighbors are friendly

Is Longboat Key, FL walkable to grocery stores?

As of early 2026, 47% of users say it's walkable to grocery stores

Is Longboat Key, FL walkable to restaurants?

As of early 2026, 46% of users say it's walkable to restaurants

Does Longboat Key, FL show holiday spirit?

As of early 2026, 46% of users say there's holiday spirit

Are there community events in Longboat Key, FL?

As of early 2026, 46% of users say there are community events

Is there wildlife in Longboat Key, FL?

As of early 2026, 45% of users say there's wildlife

Are yards well-kept in Longboat Key, FL?

As of early 2026, 43% of users say yards are well-kept

Do kids play outside in Longboat Key, FL?

As of early 2026, 24% of users say kids play outside

What is 2159 Harbourside Dr estimated to be worth?

Trulia's estimated value for 2159 Harbourside Dr in Longboat Key, FL is $1,026,500 .

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 $947K. That is up $16.67K from the prior month.

Does 2159 Harbourside Dr have air conditioning?

Yes, 2159 Harbourside Dr in Longboat Key, FL has air conditioning.

2159 Harbourside Dr, Longboat Key, FL 34228

OFF MARKET

$1,026,500

Trulia Estimate

3 Beds
2.5 Baths
2,219 sqft

2159 Harbourside Dr, Longboat Key, FL 34228

Est. Refi. Payment $6,830/mo*

Refinance Your Home

Currently Off Market - Sold Apr 11, 2017 for $635,000

Home Value

Trulia Estimate

$1.03M

Since last month

$49K (+5%)

Since last year

$82K (+8.7%)

Since last sale

$392K (+61.7%)

Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +57% in the last 10 years

Month	Estimated value
2026
October 2026	$1.03M
September 2026	$1.03M
August 2026	$978K
July 2026	$973K
June 2026	$998K
May 2026	$987K
April 2026	$993K
March 2026	$990K
February 2026	$987K
January 2026	$958K
2025
December 2025	$962K
November 2025	$965K
October 2025	$952K
September 2025	$944K
August 2025	$937K
July 2025	$972K
June 2025	$977K
May 2025	$991K
April 2025	$1.02M
March 2025	$1.04M
February 2025	$1.05M
January 2025	$1.04M
2024
December 2024	$1.02M
November 2024	$1.02M
October 2024	$982K
September 2024	$993K
August 2024	$990K
July 2024	$991K
June 2024	$1.02M
May 2024	$1.05M
April 2024	$1.07M
March 2024	$1.08M
February 2024	$1.11M
January 2024	$1.13M
2023
December 2023	$1.09M
November 2023	$1.07M
October 2023	$1.09M
September 2023	$1.07M
August 2023	$1.08M
July 2023	$1.14M
June 2023	$1.16M
May 2023	$1.11M
April 2023	$1.12M
March 2023	$1.15M
February 2023	$1.22M
January 2023	$1.25M
2022
December 2022	$1.27M
November 2022	$1.27M
October 2022	$1.27M
September 2022	$1.25M
August 2022	$1.28M
July 2022	$1.31M
June 2022	$1.33M
May 2022	$1.32M
April 2022	$1.29M
March 2022	$1.24M
February 2022	$1.12M
January 2022	$1.08M
2021
December 2021	$1.07M
November 2021	$1.05M
October 2021	$1.03M
September 2021	$1.01M
August 2021	$986K
July 2021	$974K
June 2021	$933K
May 2021	$895K
April 2021	$774K
March 2021	$757K
February 2021	$753K
January 2021	$759K
2020
December 2020	$764K
November 2020	$760K
October 2020	$747K
September 2020	$717K
August 2020	$744K
July 2020	$750K
June 2020	$757K
May 2020	$737K
April 2020	$714K
March 2020	$692K
February 2020	$679K
January 2020	$682K
2019
December 2019	$680K
November 2019	$677K
October 2019	$673K
September 2019	$674K
August 2019	$669K
July 2019	$690K
June 2019	$678K
May 2019	$671K
April 2019	$675K
March 2019	$670K
February 2019	$674K
January 2019	$671K
2018
December 2018	$664K
November 2018	$666K
October 2018	$666K
September 2018	$669K
August 2018	$663K
July 2018	$653K
June 2018	$660K
May 2018	$663K
April 2018	$661K
March 2018	$653K
February 2018	$647K
January 2018	$640K
2017
December 2017	$644K
November 2017	$649K
October 2017	$644K
September 2017	$640K
August 2017	$652K
July 2017	$652K
June 2017	$644K
May 2017	$639K
April 2017	$636K
March 2017	$653K
February 2017	$649K
January 2017	$649K
2016
December 2016	$648K
November 2016	$652K
October 2016	$653K

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

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
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
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
2110 Harbourside Dr #522-5, Longboat Key, FL	0.20	Condo	$715,000	12/22/25	3	2	2,039
2110 HARBOURSIDE DRIVE #522, Longboat Key, FL	0.21	Condo	$715,000	12/18/25	3	2	2,039

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.

Address	Price	Bed	Bath	Sqft	Status
2245 Harbourside Dr #1-101, Longboat Key, FL 34228	$946,700	2	3	2,219	Off Market
2243 Harbourside Dr #1-102, Longboat Key, FL 34228	$763,000	3	2	2,224	Off Market
2241 Harbourside Dr, Longboat Key, FL 34228	$949,100	3	3	2,219	Off Market
2239 Harbourside Dr, Longboat Key, FL 34228	$948,000	3	2.5	2,428	Off Market
2237 Harbourside Dr, Longboat Key, FL 34228	$1,153,200	3	2.5	2,352	Off Market
2233 Harbourside Dr, Longboat Key, FL 34228	$865,100	3	3	2,224	Off Market
2235 Harbourside Dr, Longboat Key, FL 34228	$536,700	3	2	1,800	Off Market
2219 Harbourside Dr #3-301, Longboat Key, FL 34228	$892,000	3	4	2,219	Off Market
2217 HARBOURSIDE DRIVE #302, Longboat Key, FL 34228	$1,338,300	3	3	2,448	Off Market
2213 HARBOURSIDE DRIVE #303, Longboat Key, FL 34228	$829,900	3	2.5	2,224	Off Market
2215 Harbourside Dr #3-304, Longboat Key, FL 34228	$636,900	3	2	2,050	Off Market
2211 HARBOURSIDE DR UNIT 305 BLDG 3 #305, Longboat Key, FL 34228	$1,050,000	3	2.5	2,219	Off Market
2199 Harbourside Dr #4-401, Longboat Key, FL 34228	$990,200	3	3	2,219	Off Market
2197 Harbourside Dr #4-402, Longboat Key, FL 34228	$983,300	2	4	2,448	Off Market
2193 Harbourside Dr #4-403, Longboat Key, FL 34228	$725,000	3	2	2,224	Off Market
2195 HARBOURSIDE DRIVE #404, Longboat Key, FL 34228	$850,000	3	2	1,906	Recently Sold
2191 Harbourside Dr #4-405, Longboat Key, FL 34228	$1,057,300	3	2.5	2,219	Off Market
2179 HARBOURSIDE DRIVE #501, Longboat Key, FL 34228	$1,332,200	3	3	2,219	Off Market
2177 Harbourside Dr #5-502, Longboat Key, FL 34228	$826,400	3	3	2,352	Off Market
2173 Harbourside Dr, Longboat Key, FL 34228	$789,500	3	2	2,224	Off Market

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

Condo

Built in 1984

2,219 sqft

$463/sqft

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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,026,500, with a rent estimate of $9,392/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 and Tax history

Date	Event	Price
Apr 11, 2017 Source: N/A	Sold	$635,000
Jan 23, 2017 Source: Agent Provided	Pending	$679,000
Aug 31, 2016 Source: Agent Provided	PriceChange	$679,000 Price decreased by 3%
May 27, 2016 Source: Agent Provided	Listed For Sale	$699,000
Feb 26, 2010 Source: N/A	Sold	$501,000
May 13, 2005 Source: N/A	Sold	$700,000

Year	Property tax	Tax assessment
2025	$11,082	$845,300

Additional Cost

Market trends in Longboat Key

Last updated August 2026

Avg. sale price

$947K

$16.67KMoM

Sale-to-List Price

94.2%

0.3%MoM

Price per sq ft

$569

$43MoM

Available listings

294

31MoM

Around this home

Southside Elementary School
K-5
Public
680 Students
Sarasota County Schools
10/10
GreatSchools Rating
Parent Rating Average
Love this school, feel so lucky to have our children here. Great teachers who love what they do, amazing parent engagement and PTO support for learning benefits like Spanish, science and the arts. Kind and mindful kids and parents in our experience. The only negative I can see is the amount of sugar/candy given out, but hey, it seems to work if you look at test scores… Blown away by this school.
Parent Review
2y ago
12 Reviews

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
Visitor
2y ago
"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
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Dougtibbetts
Resident
2y ago
"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
Resident
2y ago
"We have monthly concerts at our Town Center during season. We also have small town 4th of July and Christmas parades"
0
Flag
Jonettesullivan
Resident
2y ago
"Dogs are plentiful and welcomed up to 50lbs. Over half of the residents in the neighborhood have a pet. "
0
Flag
Dougtibbetts
Resident
2y ago
"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
Resident
6y ago
"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
Resident
7y ago
"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
Resident
7y ago
"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.
Visitor
8y ago
"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
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Kristonlamb
Resident
8y ago
"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
11y ago
"Beautiful place. It's only 5 minutes from St. Armands Circle where there are great restaurants and shops. "
0
Flag
tom_sweet
12y ago
"Only 5 minutes away from the restaurants in St. Armands Circle and Sarasota makes it so convenient to go out. "
0
Flag
Janet M.
12y ago
"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

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 $1,026,500.
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 $947K. That is up $16.67K from the prior month.
Does 2159 Harbourside Dr have air conditioning?
Yes, 2159 Harbourside Dr in Longboat Key, FL has air conditioning.