Homes for sale · Sarasota, FloridaFive Points
Downtown Sarasota living at the center of it all
43
Homes for sale
$1,300,000
Median list price
$882
Avg price / sqft
175
Median days on market
Five Points sits at the literal crossroads of downtown Sarasota, where the city's streets fan out from a historic intersection toward the bayfront. This is urban Sarasota at its most walkable — a neighborhood of condo towers, converted historic blocks, and nearby pockets like the Rosemary District and Golden Gate Point that trade the single-family lifestyle for culture, restaurants, and proximity to the water. It suits buyers who want to step out their door into the heart of things rather than drive to them.
The market here skews high and moves deliberately. With 43 active listings and a median list price of $1,300,000, Five Points is firmly in Sarasota's luxury tier — 27 of those homes are priced above $1M, and new construction accounts for 13 active listings. Homes take time to trade, with a median 172 days on market and sellers landing about 93% of asking, so a patient, well-advised buyer has real room to negotiate.
Five Points is a community in Sarasota, Florida.
Quick facts
$329,900 – $8.3M price range
1,822 sqft median home
$2,247/mo median HOA
$5,000/mo median rent
59 sold in 12 months
Drive times
Living in Five Points
Five Points takes its name from the historic downtown intersection where several of Sarasota's main streets meet, and that geography defines the lifestyle. This is the urban core of the city — a place of condo towers, restored commercial blocks, and ground-floor storefronts rather than lawns and cul-de-sacs. Residents trade square footage and yards for the ability to walk to dinner, culture, and the bayfront.
The area suits a specific buyer: someone who values proximity and walkability over space. Downsizers, professionals, and second-home owners who want to lock the door and travel all find the lifestyle appealing. The median home size of about 1,923 square feet reflects the condo-heavy character of the neighborhood.
What you get in return is being at the center of Sarasota rather than on its edges. The bayfront, the cultural institutions downtown, and the barrier islands beyond are all close at hand. It's a lifestyle built around the idea that the best amenities are the ones you can reach on foot.
Neighborhoods and communities in Five Points
Five Points anchors a cluster of distinctive downtown-adjacent pockets. The Rosemary District, just to the north, has become one of the most active areas for new condo and mixed-use development, drawing buyers who want modern construction within walking distance of the core. Golden Gate Point, the slim peninsula reaching toward the bay, offers a more exclusive, water-oriented enclave.
For buyers wanting a more traditional single-family feel nearby, Arlington Park offers an established residential neighborhood with its own character a short drive from the center. Further out, communities like Sky Ranch provide different options for those willing to leave the immediate downtown footprint.
The barrier islands are also part of the picture. Lido Key, with its Gulf beaches, sits a short drive across the bay and draws many of the same buyers considering a downtown condo. Together these areas give Five Points buyers a spectrum — from high-rise urban living to beachfront to leafy residential streets — all within the broader Sarasota market.
Homes for sale in Five Points: prices and housing
Five Points is a luxury submarket. The median list price sits at $1,300,000, with active listings ranging from $329,900 all the way up to $8,275,000. Of the 43 homes on the market, 27 are priced above $1M, and the average price per square foot is $882 — a figure that reflects the premium placed on downtown location and newer condo product.
The housing stock is condo-dominated, which shows in both the compact median size of 1,923 square feet and the elevated HOA costs. The median HOA runs about $2,271 per month, typical for buildings that cover maintenance, amenities, and reserves. The median annual property tax is $11,871, consistent with the area's price points. New construction is a meaningful part of the inventory, with 13 active listings — a reflection of ongoing development near the core.
The market moves at a measured pace. Homes sit a median of 172 days on market, and over the past 12 months 59 homes sold at a median price of $1,100,000. Sellers are averaging about 93% of asking, which signals a market where buyers have leverage and pricing discipline matters. For a well-prepared buyer, there is genuine room to negotiate, especially on listings that have lingered.
Schools in Five Points
The current data does not list specific assigned schools for Five Points, which is common for a dense downtown area where the household mix skews toward professionals, downsizers, and second-home owners rather than families with school-age children. That doesn't mean the area isn't zoned — it means you should verify the specific assignment for any address you're considering.
Sarasota County operates a public school choice and zoning system, so the right step is to check the district's official school locator using the exact property address. Attendance boundaries can shift from year to year, and two listings a few blocks apart may fall into different zones.
If schools are a priority, have your agent confirm the current assignment in writing before you make an offer, and look into any magnet or choice options the district offers. Never rely on a listing's informal claim about schools — always confirm with the county directly.
Getting around Five Points
The defining feature of getting around Five Points is that you often don't need to drive. As the historic hub of downtown Sarasota, the neighborhood puts dining, culture, and the bayfront within walking distance, which is a large part of its appeal. Many residents keep a car for errands and trips but handle daily life on foot.
When you do drive, the downtown street grid and nearby arterials connect quickly to the rest of the region. The barrier islands and the beaches are a short drive across the bay, and the broader Sarasota area is easily reachable.
For regional trips, I-75 is the main north-south artery. Expect roughly 69 minutes to downtown Tampa, which puts Tampa's airport and employment centers within reach for occasional commutes or travel, even if the daily rhythm of Five Points is decidedly local.
Is Five Points a good place to live?
Five Points is an excellent choice for a particular kind of buyer — one who wants to live at the center of downtown Sarasota, with walkability, culture, and the bayfront close at hand. The lifestyle is urban and condo-oriented, which is a feature for downsizers, professionals, and second-home owners, but a trade-off for anyone wanting a yard or a quiet residential street.
The honest financial picture is that this is a luxury market. With a median list price of $1,300,000, average $/sqft of $882, HOA dues around $2,271 per month, and median taxes near $11,871 a year, carrying costs are significant. The upside for buyers is a measured market: a 172-day median time on market and sellers averaging 93% of asking mean you can negotiate rather than overpay.
If downtown, walkable living is what you're after, Five Points delivers it as well as anywhere in Sarasota. Go in clear-eyed about the price point and the condo-ownership costs, verify school zoning and association finances for any specific building, and you'll have a realistic view of what life here looks like.
On the market now
Homes for sale in Five Points
View all 43 →
$1,450,000
1233 N GULFSTREAM AVENUE UNIT 401, SARASOTA
2 bd · 2.5 ba · 1,940 sqft
$1,150,000
200 COCOANUT AVENUE UNIT 2, SARASOTA
2 bd · 2.5 ba · 1,721 sqft
$949,990
200 COCOANUT AVENUE UNIT 4, SARASOTA
2 bd · 2.5 ba · 1,721 sqft
$559,999
101 S GULFSTREAM AVENUE UNIT 5G, SARASOTA
1 bd · 2 ba · 965 sqft
$515,000
1350 MAIN STREET UNIT 1409, SARASOTA
1 bd · 1 ba · 900 sqft
$399,000$399,900
33 S GULFSTREAM AVENUE UNIT 702, SARASOTA
1 bd · 1 ba · 820 sqft
$329,900
33 S GULFSTREAM AVENUE UNIT 307, SARASOTA
1 bd · 1 ba · 820 sqft
$1,250,000
111 S PINEAPPLE AVENUE UNIT 1103, SARASOTA
2 bd · 2.5 ba · 1,600 sqft
$865,000
1350 MAIN STREET UNIT 704, SARASOTA
2 bd · 2 ba · 1,336 sqft
$435,000
101 S GULFSTREAM AVENUE UNIT 12C, SARASOTA
1 bd · 2 ba · 985 sqft
$895,000
1255 N GULFSTREAM AVENUE UNIT 204, SARASOTA
2 bd · 2 ba · 1,822 sqft
$2,700,000
1233 N GULFSTREAM AVENUE UNIT 1404, SARASOTA
3 bd · 4.5 ba · 2,906 sqft
Every active listing inside the Five Points boundary
Open full map search →Find your fit
Browse Five Points
By feature — on the live map
Where the market lives
The numbers that matter
The Five Points market
59
Sold, last 12 months
$1,100,000
Median sold price
93%
Sale-to-list ratio
What sellers actually get vs asking
74 days
Median time to sell
Five Points vs Sarasota
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 25.9% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Five Points boundary. Rolling medians smooth single-month swings in small communities.
What it really costs
Owning here
Owning the median Five Points home
≈ $10,258/mo
$1,300,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$2,247/mo
Median HOA
From current listings inside the boundary
$5,000/mo
Median rent
Homes for rent inside the boundary
Population
1,389
Median age
69
Median income
$87,843
Median home value
$1,075,031
Beyond the listings
Living in Five Points
Lifestyles
Top 2% in the U.S.Wealth Signaling
Interested in the finer things life has to offer, this population wants to display their lifestyle by discussing luxury products. Often references jewelry, cars, and home features.
Relationships
Top 4% in the U.S.Networking
Driven to succeed in the business world, this population seeks to progress in their career through networking happy hours, summits, and connecting with other professionals online.
Relationships
Top 6% in the U.S.Love & Romance
Love is in the air when this population is present. Includes people expressing their feelings for significant others in special ways. Common activities include anniversaries and date nights.
Entertainment
Top 7% in the U.S.Film Lovers
Movie buffs and binge watchers expressing their love for movies, storytelling, and the film making process.
Culture
Top 7% in the U.S.Dance Devotion
Some dance for fitness, others for fun, and a few turn it into a profession. No matter how these people groove to the music, their love for dance is what bonds them.
Pieces of History
You can find these people researching an upcoming exhibit at the natural history museum or learning about a famous monument. This population enjoys learning about the past.
Straight answers
Five Points FAQs
Is Five Points a good place to live?+
It's a strong fit if you want walkable, downtown Sarasota living with restaurants, culture, and the bayfront at your doorstep. It's less suited to buyers wanting a yard or a quiet suburban street. The trade-off is urban density and a luxury price point in exchange for being at the center of everything.
Is Five Points expensive?+
Yes — it's one of Sarasota's higher-priced areas, with a median list price of $1,300,000 and an average of $882 per square foot. Of the 43 active listings, 27 are priced above $1M. Prices range widely, from $329,900 up to $8,275,000, so there is some entry at the lower end.
What do homes cost in Five Points?+
Active listings run from $329,900 to $8,275,000 with a median list price of $1,300,000. Over the past 12 months, 59 homes sold at a median price of $1,100,000. The median home size is about 1,923 square feet, consistent with a condo-heavy downtown market.
How is the market in Five Points right now?+
It's a deliberate market that favors prepared buyers. Homes sit a median of 172 days on market, and sellers are getting about 93% of asking on average. With 43 active listings and 59 sales in the past year, there's steady inventory and real room to negotiate.
What are HOA fees and property taxes like?+
Because this is a condo-dominated area, HOA fees run higher than in single-family neighborhoods — the median is about $2,271 per month, which typically covers building amenities and maintenance. The median annual property tax is $11,871, in line with the area's luxury price points. Always confirm the specific association budget and reserves before you buy.
What about schools in Five Points?+
Specific assigned schools aren't listed in the current data for this neighborhood, so verify any address directly with the Sarasota County Schools zone locator. Attendance zones can change year to year, and downtown addresses may feed different schools than nearby areas. Your agent can pull the exact zoning for any listing you're considering.
Is there new construction in Five Points?+
Yes — 13 of the 43 active listings are new construction, reflecting ongoing condo development near the city center and in adjacent pockets like the Rosemary District. New product tends to command the higher end of the price range. If a new building matters to you, it's worth watching pre-construction releases closely.
What's the commute like from Five Points?+
Five Points is built for a short, walkable daily routine rather than a long commute, with downtown Sarasota amenities right at hand. If you work in the Tampa area, expect roughly 69 minutes to downtown Tampa via I-75 and I-275. For most residents, the appeal is leaving the car parked and walking.
Keep exploring
More Sarasota neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. IDX information is 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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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