1980s bayfront condominium · Bay Isles, Longboat Key · Sarasota County · ZIP 34228
A bayfront Bay Isles condominium on Longboat Key, calmer water and a deeded private Gulf beach club, where the reserve, flood, and insurance math sets the price.
Bayfront in gated Bay IslesPrivate Gulf beach club1980s condo, read reserves
Live Market Pulse
50/100 Momentum
Buyer-Leaning Market (limited data)
Fairway Bay is a condominium, so the honest read is the association: the milestone inspection and reserve study, the insurance and flood picture, the leasing rules, and the deeded Bay Isles beach club access, all confirmed per unit and per association.
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Unlock Off-Market Fairway Bay
Listings before the portals, true comps, and the renovation and carrying-cost math, before you tour.
Built fromLive Stellar MLS data14 years of closingsLocal renovation analysisUpdated twice daily
LiveMarket PulseStellar MLS
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Median Price
0mo
Supply
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Avg DOM
Soft
Seller Leverage
n/a
Median $/Sqft
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1-Yr Price Change
0now
Distress
Jon's Current Read
"Fairway Bay is a 1980s bayfront condominium inside the gated Bay Isles enclave on the Sarasota County end of Longboat Key, and the read is a condo read, not a single-family one. You are buying calmer Sarasota Bay water, generous floor plans for the key, and the deeded Bay Isles private Gulf beach club, but the number is driven by the association: Florida now requires a milestone structural inspection and a structural integrity reserve study on older coastal condos, so the live questions are reserve funding, any special assessment, the post-Helene and Milton insurance posture, and the leasing rules. Your leverage is reading those association documents honestly before you fall for a bay view."
Jon Brooks, founder, Momentum Realty · Updated June 2026
The 60-Second Overview
Fairway Bay is a bayfront condominium community on Harbourside Drive inside Bay Isles, the gated master community on the bay side of Longboat Key, in the Sarasota County portion of the island (Bay Isles Association; Corcoran Dwellings community guide, 2026). It sits on Sarasota Bay rather than the Gulf, which buys calmer water, boating-friendly access, and typically more interior space for the money.
The community was built in the 1980s and combines midrise condominium buildings with townhouse residences on landscaped grounds along the bay, with units spanning a wide size range for the key (Corcoran Dwellings, 2026). Because the buildings date to the 1980s, condition varies by unit and renovation timeline, and the association documents matter as much as the floor plan.
The signature benefit of a Bay Isles address is the deeded private Gulf beach club: residents live on the bay yet have access to a private stretch of Gulf sand a short drive away. Confirm exactly how the beach club access conveys for any specific unit, since that deeded benefit is a real part of what you are buying.
The pitch is bayside space inside a gated community with a private Gulf beach, a short drive to St. Armands Circle and downtown Sarasota. The work is the condo diligence: the milestone inspection and reserve study, the insurance and flood posture after the 2024 storms, the dues and any assessment, and the leasing rules, all verified per association and per unit.
Quick Match
Who Fairway Bay is best for.
Best for
Buyers who want calmer bayfront living with generous condo floor plans
Buyers who value a gated Bay Isles setting and a deeded private Gulf beach club
Owner occupants comfortable reading condo reserves, insurance, and milestone reports
Buyers who want a short drive to St. Armands Circle and downtown Sarasota
Probably not for
Buyers who need to step from their door directly onto Gulf sand
Anyone unwilling to verify reserves, assessments, and insurance per association
Buyers seeking a transient nightly rental investment rather than a residence
Buyers who want brand new construction with no older-building reserve questions
Market Pulse
How Fairway Bay is performing right now
50/100 momentum
Buyer-Leaning Market (limited data)
Seller's marketBalancedBuyer's market
0Months of supplytight
24Median days on marketdays
0 : 0Under contract vs for salestrong demand
0Sold in last 12 monthsliquidity
+127%Median price since 2012appreciation
+0%Asking vs recent sold $/sqftroom to negotiate
Tight supply and strong demand favor sellers here. Homes still take about two months to sell, though, and with asking prices running above recent sales per square foot, a prepared buyer has room on anything overpriced. Reading each home against the real comps, not the headline trend, is where the edge is.
Live from Stellar MLS, as of June 30, 2026. Refreshed twice daily. Months of supply, days on market, and the contract-to-listing ratio are computed from current Fairway Bay listings and the trailing twelve months of closed sales.
8.6A- score
Momentum intelligence
Momentum buy score
Our proprietary read on how a home in Fairway Bay buys, holds, and resells. See the five factors.
Interactive Map
Fairway Bay on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers, color the dots by status or lot type, and tap a home for the details.
Two community pools plus spa and wellness facilities
Tennis and pickleball courts on site
Clubhouse with kitchen, fitness center, kayak launches
Longboat Key Club golf nearby, membership separate
Fairway Bay is a bayfront condominium community inside the gated Bay Isles enclave on Longboat Key, combining midrise and townhouse residences on landscaped grounds along Sarasota Bay. Amenities include community pools, a spa and wellness facilities, tennis and pickleball, a fitness center, a clubhouse with a kitchen, kayak launches, and a bayside walking path, plus the deeded Bay Isles private Gulf beach club (Bay Isles Association; Corcoran Dwellings, 2026). Because it is a 1980s condominium, confirm the association reserves, milestone status, insurance, and leasing rules, and how the beach club access conveys, for any specific unit before you buy.
Nearby & Commute
How far is everything?
The takeaway
Fairway Bay trades direct Gulf-front footing for calmer bay water, generous floor plans, and a gated Bay Isles setting, with a short drive to St. Armands Circle, the beach club, and downtown Sarasota.
Drive times from Fairway Bay. They are approximate and vary with traffic, the season, and your exact start point on the key.
St. Armands Circle~10 to 15 min · shops and dining
Longboat Key Club golf~5 min · membership separate
Downtown Sarasota~15 to 20 min · via St. Armands
Lido Key Beach~10 to 15 min · Gulf beach
Sarasota-Bradenton Airport~25 to 35 min · regional air
Sarasota Memorial Hospital~20 to 25 min · main hospital
Publix and island services~5 min · everyday errands
Distances and drive times are approximate and vary with traffic and your exact unit. Confirm your real commute at your real departure time.
Nearby Communities
Explore more neighborhoods near Fairway Bay with Momentum Realty’s local guides.
No CDD bond means thousands less per year than newer master plans.
Typical CDD community~$2,500/yr
Fairway Bay (no CDD)$0/yr
Roughly $25,000 saved over 10 years in carrying cost, before resale.
Illustrative. NE Florida CDD assessments commonly run $1,500-$3,500+/yr and vary by community; verify per property.
Schools
15-Second Take
Sarasota County Public Schools
Verify the zoned schools by address
Magnet and choice options may be available
Confirm current ratings before relying on them
Private and parochial options nearby
Fairway Bay is served by Sarasota County Public Schools. Assignment is by address and can change, so confirm the exact zoned elementary, middle, and high schools for any specific home, plus any magnet or choice options. Treat published ratings as a starting point, not the full story.
Public
Sarasota County Public Schools (verify by address)
What is actually shaping value at Fairway Bay: the post-Helene and Milton insurance and recovery picture on Longboat Key, Florida's condominium milestone and reserve requirements on older coastal buildings, and the steady appeal of a gated Bay Isles address with a private Gulf beach club. Each item is sourced and linked.
Recent Developments in Fairway Bay
Development Intelligence
Our read on what is being built around Fairway Bay, scored for direction, significance, and how close the effect lands. The full sourced timeline follows below.
Net OutlookBullishBay Isles location and the beach club benefit support steady demand, with the watch items being condo reserve funding, possible special assessments, and the coastal insurance market after the 2024 storms.
Post-Helene and Milton insurance and recovery
2025
NeutralMajor impact
SignificanceRadius: Island
The 2024 storms reshaped the insurance and recovery picture on Longboat Key, so a building's storm history, repairs, and coverage have to be verified.
Condo milestone and reserve study requirements
2024 to 2025
NeutralMajor impact
SignificanceRadius: Community
Florida requires milestone inspections and structural integrity reserve studies on older coastal condos, so reserve funding and assessments drive the buy.
Bay Isles gated setting and private beach club
Ongoing
BullishNotable impact
SignificanceRadius: Community
The gated enclave and the deeded Gulf beach club remain a durable draw that supports demand for a bayfront address.
Coastal floodplain and elevation exposure
Ongoing
NeutralNotable impact
SignificanceRadius: Island
Longboat Key sits in the coastal floodplain, making the FEMA flood zone, elevation, and flood insurance essential diligence.
Proximity to St. Armands and downtown Sarasota
Ongoing
BullishNotable impact
SignificanceRadius: Area
A short drive to St. Armands Circle and downtown Sarasota underpins the convenience case that supports demand.
Older-building condition and reserves vary by association
Ongoing
NeutralMinor impact
SignificanceRadius: Community
Because the buildings date to the 1980s, condition and reserve posture differ, so each association and unit must be read on its own.
Direction, significance, and effect-radius ratings are Momentum's proprietary, qualitative read of the sourced items below, not investment advice or a prediction for any specific home.
Development, infrastructure, retail, and school activity affecting Fairway Bay, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated June 2026.
Showing the latest, scroll for all updates ↓
October 2025
Insurance
Longboat Key awaits insurance and FEMA funds after 2024 storm cleanup
Local reporting describes Longboat Key still working through insurance and FEMA reimbursement for cleanup costs in the wake of Hurricanes Helene and Milton, underscoring how the 2024 storms reshaped the island recovery and coverage picture. Why it matters: The post-storm insurance and recovery posture is now central to any older coastal condo buy on the island. Source
December 2024
Regulation
Florida condo milestone inspection and reserve study deadlines take effect
Florida law set a December 31, 2024 milestone inspection deadline for qualifying older three-story-plus buildings near the coast, and required associations to complete structural integrity reserve studies, with the practical effect of more scrutiny of reserves and potential special assessments. Why it matters: Reserve funding and possible assessments are now front-and-center diligence items for 1980s coastal condos like Fairway Bay. Source
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
The Strategy
The Fairway Bay buying strategy.
If we were buying in Fairway Bay, this is the order of operations we would run, and the one we run for our clients.
1
Read the association financials first. On a 1980s condo, the reserve study, the milestone inspection, and any special assessment drive the number more than the bay view.
2
Confirm the milestone and reserve status. Florida requires a structural milestone inspection and a structural integrity reserve study on older coastal condos, so ask for the latest reports and the funding plan.
3
Quote insurance and read the flood zone early. Longboat Key sits in the coastal floodplain, and the post-Helene and Milton market shapes premiums, so price the specific unit and association coverage.
4
Verify the leasing rules and the beach club access. Confirm the current leasing provisions and exactly how the deeded Bay Isles Gulf beach club conveys for the unit you are considering.
5
Use the bayside context, and cross-shop a barrier-island option such as Sarasota Beach on Siesta Key if you want to weigh bay against Gulf.
The Quick Decision
Best Buy
A renovated bay-facing unit in a well-reserved association with the beach club benefit confirmed
Biggest Risk
An underfunded reserve, a pending special assessment, or an uninsurable older building
Best Lot
A bay-facing position with the better water view, weighed against floor and elevation
Smart Timing
Confirm the milestone, reserve study, insurance, and leasing rules before you offer
Deep-Dive Intelligence
The full read, only if you want it.
The takeaway
On mobile, tap any heading below to open it. This is the home by home, lot by lot, club and renovation detail, organized so you can jump straight to what matters to you.
Community Details at a Glance
Fairway Bay is a bayfront condominium community inside the gated Bay Isles enclave on Longboat Key, combining midrise and townhouse residences on landscaped grounds along Sarasota Bay. Amenities include community pools, a spa and wellness facilities, tennis and pickleball, a fitness center, a clubhouse with a kitchen, kayak launches, and a bayside walking path, plus the deeded Bay Isles private Gulf beach club (Bay Isles Association; Corcoran Dwellings, 2026). Because it is a 1980s condominium, confirm the association reserves, milestone status, insurance, and leasing rules, and how the beach club access conveys, for any specific unit before you buy.
Fairway Bay Homes For Sale
What your money buys in Fairway Bay.
The takeaway
Three honest price bands. Condition and lot, not the square footage alone, decide where a home lands.
Here are the broad resale bands in Fairway Bay today. The right home is the one matched to your budget and the renovation math, so seeing fitting listings early is the edge.
The Entry Unit
A smaller or original-condition condo where the renovation budget and the association reserves drive the real cost. The accessible way into Bay Isles.
Lowest entry
The Updated Bayfront
A renovated bay-facing unit with a strong water view in a well-reserved association, the heart of the resale market here.
Most inventory
The Top
A larger townhouse or top-tier bay-facing residence with the best views and finishes, the units that hold value best when the association is sound.
Strongest resale
Approximate 2026 resale bands from third-party listing data and public records, not NEFAR statistics. Confirm pricing for a specific home.
Three realistic price bands. Where a home lands comes down to condition and lot, not square footage alone.
The Entry Unit
A smaller or original-condition condo where the renovation budget and the association reserves drive the real cost. The accessible way into Bay Isles.
The Updated Bayfront
A renovated bay-facing unit with a strong water view in a well-reserved association, the heart of the resale market here.
The Top
A larger townhouse or top-tier bay-facing residence with the best views and finishes, the units that hold value best when the association is sound.
Approximate 2026 resale bands from third-party listing data and public records, not NEFAR statistics. Confirm pricing for a specific home.
Operator Intelligence
Renovation & Resale Intelligence
The factors that actually move value in Fairway Bay, condition, lot, and the renovation math, read from current listings and recent sales.
15-Second Take
Renovation math decides the deal
Golf and lake lots resell strongest
Roof and HVAC age drive the insurance quote
Interior lots are where buyers overpay
Proprietary Data
The renovation premium.
Renovated-listing inventory in Fairway Bay is too thin right now to compute a reliable renovation premium. We read condition home by home against real comps before you offer.
Lot Value
The lot premium.
On golf, lake, and preserve frontage, the homesite is the part of your money the market gives back at resale. The house can be renovated; the lot cannot, so premium lots hold their value better than interior ones. How much more they command varies by frontage, view, and condition, which is why we read it home by home against real comparable sales rather than a single headline figure.
Operator Note
Most buyers overpay on interior lots in the back half of the community. A sharp renovation can distract you, but the weaker resale position follows the lot, not the finishes. We read the homesite before the kitchen.
Resale Strength Scorecard
How well Fairway Bay holds value.
Our read on the factors that protect resale here, and the one to manage.
Bay Isles location and accessStrong
Private Gulf beach club benefitPositive
Association reserves and milestoneVerify per association
Insurance and flood postureVerify per unit
Unit condition and viewVerify per unit
Momentum analysis based on the no-CDD structure, central location, built-out lot scarcity, the funded club plan, and the all-resale 1990s housing stock. Not a guarantee of future value.
Operator Note
The strongest value pocket is usually a renovated golf or lake home priced just under the next tier up. Buyers chasing the single biggest estate often pay estate prices for what is really a renovation project.
5 Mistakes Buyers Make in Fairway Bay
15-Second Take
Calling the listing agent (who works for the seller)
Misjudging the renovation budget
Overpaying for an interior lot
Ignoring the optional club cost
Skipping the roof, HVAC, and systems check
In an all-resale, seven-figure, renovation-driven market, the same five mistakes cost buyers the most. Every one is avoidable with the right preparation before you tour.
1
Calling the listing agent
The agent on the sign works for the seller. In a market where condition swings price by hundreds of thousands, negotiating against that agent with no one in your corner is the costliest move of all.
2
Misjudging the renovation math
A dated home looks like a deal until you price the roof, HVAC, pool, and full modernization honestly. Underbudget the reno and the bargain becomes the expensive house.
3
Overpaying for an interior lot
Golf frontage, lakefront, and preserve lots carry real, durable premiums. Pay an estate price for an interior lot and you are buying the weakest version of the value.
4
Ignoring the club decision
The club is optional and separate, so two similar homes can cost very differently to own. Buyers who do not price the membership they will actually use misread their real monthly number.
5
Skipping the systems check
A 1990s home means 1990s-era systems unless updated. Roof age, HVAC age, pool equipment, and prior renovations drive both price and insurability, and a thorough inspection matters more here than in a new build.
“
Fairway Bay sells calmer bay water and a private Gulf beach club, but it is a 1980s condominium. The deal is won or lost on the reserves, the milestone inspection, the insurance, and the leasing rules.
Jon Brooks · Founder, Momentum Realty
Momentum Intelligence
Momentum Buy Score.
Our proprietary 0 to 10 read across the five factors that decide how a home here buys, holds, and resells.
7.3B · Buy Score
Resale Strength7.4/10
Renovation Risk5.0/10
Location Efficiency8.4/10
Long-Term Defensibility7.2/10
Carrying Cost Advantage5.5/10
Momentum Intelligence Scores are our proprietary, qualitative assessment based on the analysis on this page, on a 0 to 10 scale. They are a framework for comparing communities, not a guarantee of future value or advice on a specific home.
Momentum Housing Intelligence
Why our read on Fairway Bay is different.
Most pages on this community are an automated estimate wrapped in stock copy. This one is built from the live Stellar MLS feed, fourteen years of closed sales, and a renovation-by-renovation read of what actually moves value here, lot by lot. No Zestimate, no guesswork.
Live Stellar MLS feed14 years of closed salesRenovation-premium analysisLot-by-lot, no automated estimates
Jon Brooks, founder of Momentum Realty. A housing economist with a background in real estate investment banking at Deutsche Bank and consulting at Ernst & Young, who has built and analyzed Northeast Florida real estate from the ground up.
Where the value actually sits. Each home is shaded by its price per square foot (a value read, not just a price) and ringed by lot type, so you can see at a glance which pockets carry a real, durable premium and where a renovation play makes sense.
Value ($/sqft)
$261 value$401 premium
Lake / waterPreserveInterior
Fill = price per square foot; ring = lot type, inferred from listing descriptions. Sold homes are shown by realized $/sqft (lot type not always recorded). Asking and recent-sold figures from Stellar MLS; for orientation, not an appraisal.
15-Second Take
Bay-facing positions with the better water view hold value
Confirm the FEMA flood zone and the building elevation
Reserve funding and assessments shape the carrying cost
Master and flood insurance are association level, verify both
Read the association and the reserves before the finishes
In a coastal condominium like Fairway Bay, the equivalent of the lot is the unit's position and the association behind it. Bay-facing positions with the better water views, in well-reserved associations, hold value better than weaker views or underfunded buildings. The interior can be renovated; the flood zone, the building, and the reserve posture cannot be changed by one owner. Read the association financials and the flood and elevation picture first, then price the condition of the unit against them.
The 15-Second Verdict
Fairway Bay in 15 seconds.
Best forBuyers who want calmer bayfront condo living in gated Bay Isles with a private Gulf beach club.
Biggest advantageBayside space plus a deeded Gulf beach club, a short drive to St. Armands and downtown Sarasota.
Biggest riskReserves, special assessments, and insurance on a 1980s coastal condo after the 2024 storms.
Sweet spotA renovated bay-facing unit in a well-reserved association with the beach club benefit confirmed.
Avoid ifYou need to step onto Gulf sand from your door or want new construction with no reserve questions.
Condo Dues, Reserves & Assessments
15-Second Take
Condo dues plus the Bay Isles master assessment, confirm both
Ask for the reserve study and current funding level
Confirm whether any special assessment is pending
Master insurance and flood are association level, verify coverage
Confirm how the Gulf beach club access conveys
Fairway Bay is a condominium, so you pay condo association dues plus the Bay Isles master assessment, and dues fund building maintenance, insurance, amenities, and reserves. On a 1980s building, the live questions are the reserve funding level and any special assessment, so confirm the exact figures and the current budget for the specific association.
Dues typically cover building exterior and common-area maintenance, the pools and amenities, master insurance on the structure, and grounds, while the Bay Isles master tier funds the gated entrance and the deeded private Gulf beach club. Confirm what conveys for the specific unit and whether any assessment is pending.
Run Your Numbers
Tools for a Fairway Bay buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and view, not the Zestimate. The right number comes from closed comps matched to your renovation level and lot.
Selling in Fairway Bay
Price it to the association, the reserves, and the renovation, not a Longboat Key average.
Selling a Fairway Bay condo means pricing to your specific association and your unit's condition and view, not to a townwide Longboat Key average. The reserve study, any assessment, the insurance posture, and your renovation level are what set the number for an informed buyer.
Momentum listings (YTD)
97.98%
Sold-to-list ratio across our market for our agents, sellers keeping more of their price.
Market average (YTD)
96.73%
The broader metro average sold-to-list ratio over the same period.
Momentum days on market
64 days
Median days on market for our listings, faster sales mean less carrying cost and stronger leverage.
Market days on market
72 days
The broader metro median over the same period.
Sold-to-list and days-on-market figures reflect Momentum Realty listings versus our market average, year to date. Your home's result depends on pricing, condition, lot, view, and preparation.
In Fairway Bay, condition and view decide your number
Because buyers here are weighing your home against renovated comps and cross-shopping Sarasota Beach, a home priced to the community average instead of its true condition and view either leaves money on the table or sits. A renovated kitchen, newer roof and HVAC, and a golf or lake view all deserve to show up in your price, and a buyer pool reading renovation math needs to be shown why your home is worth it. We build that case with real comps and a pricing strategy for the current market.
What is your Fairway Bay home worth?
Get a no-obligation home value based on real comparable sales in Fairway Bay matched to your condition, lot, and view, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
Price History: What Homes Here Have Actually Sold For
Median sale prices in Fairway Bay year by year since 2012, from closed MLS sales. A long track record beats a single estimate, showing what this community has really done through rate cycles rather than what a model predicts.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Sarasota County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
Fairway Bay Market Scorecard
Strong seller's market
Fairway Bay is currently a strong seller's market. About 1.8 months of supply, a median asking price of $1,019,500, and homes go under contract in about 58 days.
1.8
Months supply
$1,019,500
Median list
$847,500
Median sold
$313
Per sqft
58
Days on mkt
6/8/41
Active/Pend/Sold
Typical home value in the 32224 ZIP is $456,759, about 13.7% above the Florida norm (Zillow Home Value Index).
Live data: Stellar MLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Frequently Asked Questions
Where is Fairway Bay located?
Fairway Bay is a bayfront condominium community on Harbourside Drive inside the gated Bay Isles enclave, on the south, Sarasota County, end of Longboat Key, in ZIP 34228 (Bay Isles Association; Corcoran Dwellings, 2026).
Is Fairway Bay on the Gulf or the bay?
It sits on Sarasota Bay, not the Gulf, which buys calmer water and generally larger floor plans. As a Bay Isles community it also includes access to a deeded private Gulf beach club, so you get a private Gulf beach a short drive away. Confirm how the access conveys for a specific unit.
When was Fairway Bay built?
Fairway Bay was built in the 1980s, with development across the decade (Corcoran Dwellings, 2026). Because the buildings are from that era, condition varies by unit and renovation timeline, and the association reserves matter to the buy.
Is Fairway Bay gated and part of Bay Isles?
Yes. Fairway Bay is a community within Bay Isles, the gated master community on the bay side of Longboat Key along Harbourside Drive, so there is a guarded entrance to the larger enclave in addition to the condo association (Bay Isles Association, 2026).
What does the Bay Isles beach club include?
Bay Isles residents have access to a deeded private Gulf beach club, a private stretch of Gulf sand, which is a signature benefit of the address (Corcoran Dwellings, 2026). Confirm exactly how the access conveys for the specific unit you are considering.
What are the condo dues at Fairway Bay?
You pay condo association dues plus the Bay Isles master assessment, funding maintenance, insurance, amenities, and reserves. Figures vary, so confirm the exact current dues, the reserve funding level, and any pending special assessment for the specific association.
Does Fairway Bay require a milestone inspection?
Florida law requires a structural milestone inspection and a structural integrity reserve study on qualifying older condominium buildings, including coastal buildings of three stories or more. Ask for the latest milestone report, the reserve study, and the funding plan during diligence.
How did the 2024 hurricanes affect Longboat Key condos?
Hurricanes Helene and Milton in 2024 caused widespread damage on Longboat Key and have shaped the insurance and recovery picture across the island (Town of Longboat Key; Your Observer, 2025). Always confirm a building's storm history, repairs, and current insurance posture.
What are the leasing rules at Fairway Bay?
Leasing terms at a condominium can vary and change, so verify them rather than assume. Check the current leasing provisions in the association documents and any applicable local short-term-rental rules before counting on any rental plan.
What schools serve Longboat Key in Sarasota County?
The Sarasota County portion of Longboat Key is part of Sarasota County Schools, with assignment by address through schools such as Southside Elementary, Booker Middle, and Sarasota High. Assignment is by address and can change, so confirm the zoned schools for any specific unit.
How far is Fairway Bay from St. Armands and downtown Sarasota?
Fairway Bay is a short drive south to St. Armands Circle and on to downtown Sarasota, with drive times that vary by traffic and the time of day. Confirm your real route and timing from the specific building.
Should I worry about flood zones at Fairway Bay?
Longboat Key sits in the coastal floodplain, so flood exposure and elevation are central to the buy. Run the FEMA flood zone, the building's elevation and flood history, and an insurance quote, at both the unit and association level, during diligence.
Is Fairway Bay a good place for full-time living?
Many units span generous floor plans for the key, so the community suits full-time owner occupants as well as seasonal residents. As with any older coastal condo, the reserves, insurance, and milestone status drive the long-term picture, so read them before you buy.
Why does pricing vary so much within Fairway Bay?
Because the community mixes midrise and townhouse units across a wide size range, with different views, floors, and renovation levels, and because the association's reserve and assessment posture affects value. The unit, the view, and the association, not a townwide average, set the price.
Who is the best real estate agent for Fairway Bay?
The best agent for Fairway Bay is one who actively works Longboat Key and knows the community's pricing, HOA and CDD details, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Fairway Bay.
How do I find a top Longboat Key real estate agent who knows Fairway Bay?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Fairway Bay and the wider Longboat Key area.
Can Momentum Realty connect me with an agent for Fairway Bay?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Fairway Bay purchase or sale - no call center and no pressure.
The Verdict
Should you buy in Fairway Bay?
An honest fit check. We will tell you when it is not your community.
Buyers who want calmer bayfront condo living with generous floor plansExcellent fit
Buyers who value a gated Bay Isles setting and a deeded private Gulf beach clubExcellent fit
Owner occupants comfortable reading reserves, insurance, and milestone reportsExcellent fit
Buyers who want a short drive to St. Armands Circle and downtown SarasotaExcellent fit
Buyers who will verify dues, assessments, and leasing rules per associationExcellent fit
Buyers who need to step from their door directly onto Gulf sandProbably not
Anyone unwilling to read reserves, assessments, and insurance per associationProbably not
Buyers seeking a transient nightly rental rather than a residenceProbably not
Buyers who want new construction with no older-building reserve questionsProbably not
Buyers unwilling to budget for coastal insurance and possible assessmentsProbably not
Get the inside read on Fairway Bay
Whether you are buying a renovation project, comparing the lots and views, weighing the optional club, or selling your Fairway Bay home, tell us what you need. Every inquiry comes straight to us. We represent you, not the seller, and what your agent is paid is negotiable and set in a written buyer agreement up front. No obligation, no spam, no high-pressure follow-up.
You are all set.
A Momentum Realty Fairway Bay specialist will reach out personally, usually the same day.
Thinking about hiring an agent here? How to find the best real estate agent in Fairway Bay - what to look for, questions to ask, and your local expert.Median sale price in Fairway Bay, Florida by year (2012 to 2026). Source: Momentum Realty.
Photography on this page is sourced from active and recently sold MLS listings in this community and remains the property of the listing brokerage and/or photographer. Listings courtesy of Stellar MLS as distributed by MLS GRID. 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; deemed reliable but not guaranteed by MLS GRID.
Get a real cash offer on your Fairway Bay home in 24 hours and close in as little as 7 days, as-is. Because Momentum is a licensed RealTrends-500 brokerage, we'll also show you what listing would net - so you choose with both numbers.
Buying or researching Sarasota County? See the full Sarasota County real estate market report - prices, inventory, schools, taxes, and every Sarasota County neighborhood.
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You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the local market average and 8 days faster, and we’ll price yours against live your area comps.
