Cypress Fairway
Condos for Sale in Orlando, FL
All 4,092 homes for sale in Orlando, FL · median $380,000 · 1,242 condos for sale in Orlando · 163 homes for sale in 32811 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
Photo via Stellar MLS
As of September 2026, Cypress Fairway in Orlando, FL has 5 homes for sale. Over the 12 months ending 2026-09-20, 10 recorded sales closed at a median of $188,000, $179 per square foot, a median 60 days on market, sellers accepting 92% of original asking (-17% versus the prior year). Homes listed or recently sold were built 2000–2000; 10 of 16 report an HOA (median $408/mo); none of the 10 geocoded homes sit in a FEMA special flood hazard zone (median elevation 101 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $3,130 ($2,460 with the full homestead exemption).
| Location | Orlando, Orange County, FL · ZIP 32811 |
|---|---|
| Home types (current listings and sales) | condos 100% |
| Amenities listed by sellers | Pool, Clubhouse, Fitness Center, Playground, Community Mailbox, Tennis Court(s) |
| Sale prices, last 12 months | $188,000 median across 10 closed sales · $179 per sq ft · -17.2% vs the prior 12 months |
| Days on market (closed sales) | 60 median |
| For sale right now | 5 active, 1 pending · median asking $225,000 · 3.8 months of supply |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2014 through 2026. Market figures describe homes, not residents. Cite as: Momentum Realty, “Cypress Fairway key facts,” movewithmomentum.com/neighborhoods/cypress-fairway, data as of September 20, 2026.
Last 30 days in Cypress Fairway: 1 new listing (median asking $225,000), 1 under contract right now, 1 closed sale (median $230,000). As of September 29, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Homes For Sale Right Now in Cypress Fairway
Live MLS inventory for Cypress Fairway. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Cypress Fairway listings as of 2026-09-28, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2014 through 2026. Tap any home to ask about it.
Every Home for Sale in Cypress Fairway Right Now (4)
All 4 active and pending Cypress Fairway listings with a detail page, newest first, refreshed twice a day from the MLS.
- 5463 Vineland Road #5203 · $225,000 · 2 bd / 2 ba · listed Sep 10, 2026 · listed by Agent Trust Realty Corporation
- 5455 Vineland Road #3310 · $159,000 · 1 bd / 1 ba · pending · listed Aug 29, 2026 · listed by Exp Realty Llc
- 5447 Vineland Road #1210 · $155,000 · 1 bd / 1 ba · listed Jun 30, 2026 · listed by Alfano Property Management
- 5447 Vineland Road #1308 · $292,990 · 3 bd / 2 ba · listed Jun 30, 2026 · listed by Empire Network Realty
Price at Cypress Fairway sits at a median of $192,000, with a median around $187 per square foot. At that per-foot figure against that overall median, you're looking at compact, condition-sensitive product where what you pay tracks closely to what shape the unit is in rather than any headline dollar range.
The posture right now is soft. Prices are down 16.2% year over year, the heat score is a cool 33, and homes are taking about 37.5 days to sell. For a buyer, that means time to inspect, negotiate, and walk if the numbers don't work. For a seller, it means pricing to the current market from day one, because the market is not doing you any favors.
Cypress Fairway right now
🟡 Balanced market. 3.8 months of supply and 17% of the inventory already under contract put buyers and sellers on roughly even footing.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of September 20, 2026. Confidence: High (6 active and pending listings, 10 closed sales in 12 months).
🔴 Off the recent peak. The trailing-12-month median ($188K) is down 17.2% from the prior 12 months ($227K). With about 6 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 20. Confidence: Medium (10 and 8 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 29, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Cypress Fairway market snapshot (as of September 20, 2026): the median sale price is about $188K ($179 per sq ft over the trailing 12 months of closed sales), a median 61 days on market for closed sales, and 3.8 months of supply, a balanced market. The trailing-12-month median is down 17% from the prior 12 months, computed from record-level Stellar MLS closed sales (10 closings in the current window).
In ZIP 32811 (Orlando), 422 homes closed in the last 12 months at a median of $276K ($219/sq ft), down 8.3% year over year, with a median 48 days on market. Right now 130 active and 32 pending listings put supply at about 4.3 months — a balanced market. See the live ZIP 32811 housing market and the Orange County market.
Stellar MLS sales records identify 111 homes in Cypress Fairway that have changed hands since 2005, built between 2000 and 2000 (median 2000), with a median living area of about 1,043 sq ft and a typical 2-bedroom, 2-bath layout; 100% are condominiums. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Cypress Fairway is an entry-priced Orlando pocket in Orange County where the median lands at $192,000. The story here is affordability paired with a market that has cooled meaningfully over the past year, so both sides need to price and plan against real conditions, not last year's.
The setting & the homes.
Aerial and on-site photos of Cypress Fairway. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Photos from Stellar MLS listings in Cypress Fairway; content deemed reliable but not guaranteed.
Who Cypress Fairway is best for.
Best for
- First-time buyers targeting a sub-$200,000 entry point in Orlando
- Value buyers who can inspect thoroughly and negotiate on condition
- Long-hold buyers comfortable riding out a softer market
Probably not for
- Buyers counting on near-term price gains
- Sellers who need to exit quickly at last year's pricing
- Anyone wanting a high-turnover, competitive-bid market
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($188K) IS the median in the snapshot above, and the move from 2025 ($227K) IS the -17.2% one-year change.
Windows contain 0 to 21 sales each (10 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2014 through 2026. Deemed reliable but not guaranteed.
Cypress Fairway Market Scorecard
Cypress Fairway is currently a strong seller's market. About 2.2 months of supply, a median asking price of $225,000, and homes go under contract in about 129 days.
Typical home value in the 32811 ZIP is $190,171, about 26.4% below the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in Cypress Fairway, Orlando
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period September 2026 through September 2026. Deemed reliable but not guaranteed.
Cypress Fairway on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Millennia Elementary · Elementary
- Southwest Middle · Middle
- Dr. Phillips High · High
Zoned schools reflect the assignments reported on recent Cypress Fairway listings and can change; always confirm with Orange County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Cypress Fairway address.
Shop the zone: Homes zoned for Dr. Phillips High High School
Recent Developments in Cypress Fairway
Development, infrastructure, retail, and school activity affecting Cypress Fairway, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated August 2026.
- July 2026Development
Capstone begins construction on The Gateway luxury apartments
Capstone Building Corp began construction on The Gateway, a 270-unit apartment community at 7250 Shadowridge Drive in Orlando, developed by JBL Development. The five-story gated project spans more than 417,000 square feet and is expected to be completed in late 2027. Amenities include a saltwater pool, fitness center, pickleball court, and a clubhouse with a restaurant and bar.
What it may mean for the marketAdds 270 market rate apartments in a five story building with resort style amenities, expanding the local rental housing stock in the Airport Lakes area of south Orlando. The project is about 7 miles south of Cypress Fairway, elsewhere in Orange County.
Source: Construction Owners - July 2026Development
Orange County opens Enclave at Canopy Park with 104 affordable units
Orange County opened The Enclave at Canopy Park, a 104-unit affordable apartment community at 4440 Canopy Park Loop developed by Archway Partners. The county contributed 3 million dollars from its Affordable Housing Trust Fund. The community includes one and two bedroom homes plus a community center, fitness center, technology lab, and EV charging.
What it may mean for the marketAdds 104 income-restricted apartment homes to the local rental supply along with new community amenities and green-certified construction. The project is about 5 miles southwest of Cypress Fairway, elsewhere in Orange County.
Source: ClickOrlando - July 2026Civic
Orange County previews new Innovation Center on West Colonial Drive
Orange County previewed its new Innovation Center at 7149 West Colonial Drive, located within the county's Multicultural Center and Senior Center complex, with an official opening set for Fall 2026. The center will offer technology programs including 3D printing and makerspace prototyping through the Orange County Library System, plus career exploration and workforce training through CareerSource Central Florida.
What it may mean for the marketAdds a county operated civic and technology facility with library and workforce programming to the West Colonial corridor. The project is about 7 miles west of Cypress Fairway, elsewhere in Orange County.
Source: Orange County Newsroom - June 2026Development
Mixed-use high-rise redesigned for 924 and 934 North Magnolia Avenue
A redesigned 17-story mixed-use high-rise was proposed for 924 and 934 North Magnolia Avenue in Orlando's North Quarter district by Acram Group. The project would include 350 residential units, about 3,300 square feet of ground-floor commercial space, and a parking garage with 510 spaces, replacing two 1972 office buildings. A public plaza is planned at the corner of Magnolia and Weber Street.
What it may mean for the marketWould replace two aging office buildings with 350 residences, ground floor retail, and structured parking, adding housing density and a public plaza along the Orlando Urban Trail. The site is about 2 miles northwest of Cypress Fairway.
Source: Florida YIMBY - June 2026Development
Planning board approves zoning for 37-story tower at 170 East Washington Street
Orlando's Municipal Planning Board voted to approve a Planned Development amendment for a 37-story, 425-foot mixed-use tower at 170 East Washington Street across from Lake Eola Park. The project would include 252 residential units, a 221-room hotel, a three-story restaurant, and structured parking. It still requires City Council consideration before construction.
What it may mean for the marketWould add a 37 story tower with 252 residences and a hotel to the downtown skyline, replacing a prior approval for a 7 story hotel and increasing high density housing and parking supply. The site is about 1 mile west of Cypress Fairway.
Source: Florida YIMBY - March 2026Development
Orlando approves the 380-acre Dowden Central Community Development District in Lake Nona
Orlando approved the Dowden Central Community Development District, a roughly 380-acre district in the Lake Nona area of southeast Orlando, in March 2026. The district provides the framework to build roads, drainage, utilities, and parks for future development phases.
What it may mean for the marketA new community development district lays the groundwork for large-scale growth in the Lake Nona area, a step that typically precedes new housing and commercial activity nearby. The site is about 12 miles south of Cypress Fairway.
Source: ClickOrlando
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 Cypress Fairway buying strategy.
If we were buying in Cypress Fairway today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Cypress Fairway.
A softening entry-price market
The 16.2% year-over-year decline is the number that shapes every decision here. Combined with a heat score of 33 and roughly 37.5 days on market, this is not a market rewarding urgency. Buyers who move deliberately, verify condition, and hold firm on price are the ones positioned to win.
Read the closings volume with care: this snapshot rests on just 8 recent closings. That's a thin sample, which means individual sales can swing the median and per-foot figures more than they would in a higher-turnover community. Treat the numbers as directional and lean on unit-level comps before committing to a price.
The location and the amenities are priced into every listing in Cypress Fairway. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Cypress Fairway buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (4.2). Basis: Recent Direction -17.2% year-over-year; Liquidity & Demand 3.8 months of supply; Pricing Power 92.2% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a thin, cooling market like this one, a handful of closings can distort the picture, and a median alone won't tell you whether a unit is priced right. We work the individual comps, weigh condition against that $187-per-foot reference, and tell you plainly when a listing is chasing last year's price. That candor matters more when the market is moving against the seller.
Cypress Fairway in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $389/month (about $4,668/yr) · median of 197 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $389 per month ($4,668 a year) — the median AssociationFee across 197 MLS records, normalised to a monthly figure; most are billed monthly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Cypress Fairway buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Cypress Fairway sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Cypress Fairway, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Cypress Fairway home worth?
Get a no-obligation home value based on real comparable sales in Cypress Fairway, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Recently off market in Cypress Fairway
Homes in Cypress Fairway that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 3 on record.
- 5455 Vineland Road #3303 · off market
- 5471 Vineland Road #7109 · off market
- 5479 Vineland Road #9213 · off market
Frequently Asked Questions
What is the median home price in Cypress Fairway?
How long do homes in Cypress Fairway take to sell?
Is Cypress Fairway a buyer's or seller's market right now?
Who is the best real estate agent for Cypress Fairway?
How do I find a top Orlando real estate agent who knows Cypress Fairway?
Can Momentum Realty connect me with an agent for Cypress Fairway?
Where is Cypress Fairway, and what county is it in?
Is Cypress Fairway a good place to live?
Should you buy in Cypress Fairway?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 28, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2014 (91 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
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 Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
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See how Cypress Fairway fits the bigger picture — live prices, inventory, and Momentum Scores:
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