Crestwynd Bay
Homes for Sale in Kissimmee, FL
All 3,084 homes for sale in Kissimmee, FL · median $375,000 · 772 townhomes for sale in Kissimmee · 938 homes for sale in 34747 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, Crestwynd Bay in Kissimmee, FL has 8 homes for sale, asking from $229,000 to $300,000 (median $255,500). Over the 12 months ending 2026-09-20, 6 recorded sales closed at a median of $247,450, $182 per square foot, a median 123 days on market, sellers accepting 88% of original asking (-12% versus the prior year). Homes listed or recently sold were built 2006 - 2007; 15 of 15 report an HOA (median $333/mo); none of the 15 geocoded homes sit in a FEMA special flood hazard zone (median elevation 117 ft). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $3,770 ($3,170 with the full homestead exemption).
Last 30 days in Crestwynd Bay: 1 new listing (median asking $300,000). As of October 16, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Homes For Sale Right Now in Crestwynd Bay
Live MLS inventory for Crestwynd Bay. 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 · 8 daysTop listing
Active · 90 days
Active · 104 days
Active · 56 days
Active · 204 days
Active · 258 days
Active · 40 days
Active · 95 daysActive and pending Crestwynd Bay listings as of 2026-10-15, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2009 through 2026. Tap any home to ask about it.
Crestwynd Bay right now
🟢 Buyer-leaning market. 13.7 months of supply and 0% of the inventory already under contract give buyers above-average negotiating leverage.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: Medium (8 active and pending listings, 6 closed sales in 12 months).
🔴 Off the recent peak. The trailing-12-month median ($247K) is down 11.6% from the prior 12 months ($280K). With about 5 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 (6 and 11 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 16, 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
Crestwynd Bay market snapshot (as of September 20, 2026): the median sale price is about $247K ($182 per sq ft over the trailing 12 months of closed sales), a median 124 days on market for closed sales, and 13.7 months of supply, a buyer-leaning market. The trailing-12-month median is down 12% from the prior 12 months, computed from record-level Stellar MLS closed sales (6 closings in the current window).
In ZIP 34747 (Kissimmee), 2,599 homes closed in the last 12 months at a median of $460K ($220/sq ft), down 3.8% year over year, with a median 75 days on market. Right now 581 active and 101 pending listings put supply at about 7.3 months - a buyer's market. See the live ZIP 34747 housing market and the Osceola County market.
County records show 14 qualified sales in Crestwynd Bay across 2024 - 2025 (7 in 2024, 7 in 2025), median $280,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Flood zones in Crestwynd Bay: of 14 listing addresses checked against the FEMA National Flood Hazard Layer, 100% sit outside the FEMA Special Flood Hazard Area (Zone X). Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Kissimmee.
Crestwynd Bay is a community of 184 homes in Kissimmee, Osceola County, built between 2006 and 2007 (median 2006.0), with a median living area of about 1,372 square feet. 9% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of Crestwynd Bay. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Crestwynd BayCrestwynd BayCrestwynd BayCrestwynd BayCrestwynd BayCrestwynd BayCrestwynd BayCrestwynd BayPhotos from Stellar MLS listings in Crestwynd Bay; content deemed reliable but not guaranteed.
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 ($247K) IS the median in the snapshot above, and the move from 2025 ($280K) IS the -11.6% one-year change.
Windows contain 0 to 14 sales each (6 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 2009 through 2026. Deemed reliable but not guaranteed.
11% of homes for sale in ZIP 34747 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-17).
Crestwynd Bay Market Scorecard
Crestwynd Bay is currently a strong buyer's market. About 13.7 months of supply, a median asking price of $255,500, and homes go under contract in about 97 days.
Typical home value in the 34747 ZIP is $399,304, about 3.0% below the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Crestwynd Bay 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 contributors.
Life at Crestwynd Bay
- Pool · reported on 14 of 14 listings
- Gated Community - No Guard · reported on 10 of 14 listings
- Playground · reported on 8 of 14 listings
- Community Mailbox · reported on 5 of 14 listings
- Gated · reported on 4 of 14 listings
- Clubhouse · reported on 3 of 14 listings
- Deed Restrictions · reported on 2 of 14 listings
- Park · reported on 2 of 14 listings
- Cable TV · reported on 1 of 14 listings
- Association Recreation - Owned · reported on 1 of 14 listings
- Gated Community · reported on 1 of 14 listings
- Security Gate · reported on 1 of 14 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Osceola County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Island Village Elementary School · Elementary
- Celebration K-8 · Middle
- Celebration High · High
Zoned schools reflect the assignments reported on recent Crestwynd Bay listings and can change; always confirm with Osceola County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Crestwynd Bay address.
Shop the zone: Homes zoned for Celebration High High School
Recent Developments in Crestwynd Bay
Development, infrastructure, retail, and school activity affecting Crestwynd Bay, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- September 2026Development
Orange County commissioners approve Tuscana land use plan in Shingle Creek Basin on 4-3 vote
Commissioners voted 4-3 to approve the Tuscana land use application from Shingle Creek Co-Owners LLC and Geyer Development, reversing a unanimous rejection in May 2025. The plan includes more than 1,000 hotel rooms, about 4,000 apartments and commercial buildings, with conditions for a raised road, flood mitigation and wetland protection. The developer projects thousands of jobs at full build-out.
What it may mean for the marketThe approval could add substantial rental housing, hotel capacity and commercial space in the Shingle Creek area, while flood-mitigation conditions will shape how and when it is built. The site is about 9 miles northeast of Crestwynd Bay.
Source: Spectrum News 13 - September 2026Infrastructure
CFX holds public meetings on 14-mile toll road through part of Split Oak Forest
The Central Florida Expressway Authority held public meetings on Sept. 16 and 17 for a 14-mile road from State Road 417 near Boggy Creek Road in Orange County to Nova Road in Osceola County. CFX says portions could begin construction next year and that the road would ease traffic on Narcoossee Road. The agency faces a legal challenge from Orange County and is pursuing an eminent domain case.
What it may mean for the marketIf built, the road would add a new east-west route between Lake Nona and St. Cloud, changing commute options and access to east Orange and Osceola land. The project is about 24 miles east of Crestwynd Bay, elsewhere in Osceola County.
Source: Spectrum News 13 - September 2026Development
Lake County approves 2,241-acre Panther Run rezoning for up to 2,624 homes near Clermont
The Lake County Commission voted 3-1 on Sept. 1 to rezone about 2,241 acres in the Wellness Way area, north of Sawgrass Bay Boulevard, for GT Homes. The planned unit development allows up to 2,624 residential units and more than 1 million square feet of non-residential space, with sites reserved for a future public high school and public safety facilities. Plans include extending County Road 455 and about 11 miles of public trails.
What it may mean for the marketThe plan adds long-term housing supply, employment space and new connector roads in south Lake County, with infrastructure planned ahead of residential growth. The site is about 9 miles northwest of Crestwynd Bay.
Source: Clermont Sun - August 2026Retail & Dining
Plans for Mattel indoor water park near Lake Buena Vista Factory Stores expand to 13 acres
Updated plans for the site off State Road 535 show a 95,000-square-foot indoor water park designed by Martin Aquatic, a separate 45,000-square-foot entertainment building and nearly 900 parking spaces. The tower height rises to as much as 100 feet and still needs Orange County approval. About 200 jobs are expected, and no opening date has been announced.
What it may mean for the marketThe project would add visitor attractions, dining and roughly 200 jobs near the State Road 535 corridor, with added traffic and parking demand nearby. The site is about 7 miles northeast of Crestwynd Bay.
Source: FOX 35 Orlando - August 2026Civic
St. Cloud council approves $6.7 million downtown apartment and parking garage agreement
The City Council unanimously approved an agreement with Atlantic Housing Partners for apartments and a parking garage next to City Hall. The Community Redevelopment Agency contributes $6.25 million and the city $460,000. The garage would hold 450 to 500 spaces, with 250 reserved for apartment residents.
What it may mean for the marketNew downtown rental housing and public parking would add residents and parking capacity to the St. Cloud core. The project is about 20 miles east of Crestwynd Bay, elsewhere in Osceola County.
Source: Spectrum News 13
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 the Orlando Metro.
The Crestwynd Bay buying strategy.
If we were buying in Crestwynd Bay 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.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
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 Crestwynd Bay.
A closer look at the Crestwynd Bay market
At a median of $182 per square foot, Crestwynd Bay prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 13.7 months of supply, a buyer-leaning market and the trailing-12-month median down 12% year over year. Homes that do trade take a median 124 days on market, useful leverage on any listing that has lingered.
The housing stock is 184 homes built between 2006 and 2007, and 9% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in Crestwynd Bay. 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 Crestwynd Bay 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 4 factors (1.5). Basis: Recent Direction -11.6% year-over-year; Liquidity & Demand 13.7 months of supply; Owner Commitment 9% owner-occupied; Pricing Power 87.9% sale-to-list. Refreshed with each data update.
What it really costs to own in Crestwynd Bay
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| HOA dues | Median $333/month across 489 MLS listings (most billed quarterly; 2026-10-15). Dues cover what the documents say they cover; ask for the budget and reserve study. |
|---|---|
| Home and flood insurance | The average Citizens Property Insurance premium in Osceola County is $1,735/yr (2,188 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. Flood: of 14 listing addresses checked against the FEMA flood map, 100% sit outside the high-risk zone. Statewide, a Zone X flood policy runs about $500-$700/yr and a high-risk zone $1,200-$2,500/yr (FEMA Risk Rating 2.0 averages, not quotes). |
| Roof and age | Median build year 2006 across 16 listings. An original roof here would be about 20 years old; under Florida's 2022 reform (SB 2-D) carriers may require an inspection past 15 years, so budget for a roof report, and for replacement where it fails. |
Email me new listings in Crestwynd Bay
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Crestwynd Bay
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Crestwynd Bay will answer, and the answer is published on this page for the next buyer.
HOA, CDD & Fees
- HOA dues reported around $333/month (about $3,996/yr) · median of 489 MLS listings, most billed quarterly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $333 per month ($3,996 a year) - the median AssociationFee across 489 MLS records, normalised to a monthly figure; most are billed quarterly. 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, 2026-10.
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Flood & Insurance Context
Of 15 sampled listing addresses in this community: 100% outside the FEMA Special Flood Hazard Area (Zone X/B/C).
Address-sampled; individual parcels vary - verify any specific address at msc.fema.gov. Check any address at FEMA's Flood Map Service Center, and see average home-insurance costs by Florida county.
Source: FEMA National Flood Hazard Layer, address-level lookups (n=15) · as of 2026-10
Tools for a Crestwynd Bay 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 Crestwynd Bay sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Crestwynd Bay, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Crestwynd Bay home worth?
Get a no-obligation home value based on real comparable sales in Crestwynd Bay, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Kissimmee →
Recently off market in Crestwynd Bay
Homes in Crestwynd Bay 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. 1 on record.
- 7646 Long Island Drive · off market
| Location | Kissimmee, Osceola County, FL · ZIP 34747 |
|---|---|
| Homes in the community | 184 (FL DOR 2025 assessment roll) |
| Years built | 2006–2007 (median 2006.0) |
| Typical living area | 1,372 sq ft (median) |
| Home types (current listings and sales) | townhouses 100% |
| Amenities listed by sellers | Pool, Gated Community - No Guard, Playground, Community Mailbox, Park, Gated |
| Sale prices, last 12 months | $247,450 median across 6 closed sales · $182 per sq ft · -11.6% vs the prior 12 months |
| Days on market (closed sales) | 123 median |
| For sale right now | 8 active, 0 pending · median asking $262,500 · 13.7 months of supply |
| Owner-occupied (homestead) share | 9% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2009 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Crestwynd Bay key facts,” movewithmomentum.com/neighborhoods/crestwynd-bay-kissimmee, data as of September 20, 2026.
Housing distress & ownership in Crestwynd Bay, Kissimmee
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 October 2026 through October 2026. Deemed reliable but not guaranteed.
Just listed in Crestwynd Bay
The newest homes for sale in Crestwynd Bay right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 2693 Andros Lane $300,000 · 3 bd · 3 ba · 1,187 sq ft · 8 days on market Courtesy of AURA HOMES, LLC.
- 2685 Andros Lane $234,000 · 3 bd · 3 ba · 1,187 sq ft · 40 days on market Courtesy of REAL BROKER, LLC
- 2691 Andros Lane $259,000 · 3 bd · 2.5 ba · 1,595 sq ft · 56 days on market Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
- 2682 Mayaguana Street $290,000 · 3 bd · 2.5 ba · 1,595 sq ft · 90 days on market Courtesy of FLORIDA HOMES REALTY & MORTGAGE
- 7601 Acklins Road $269,000 · 3 bd · 2.5 ba · 1,595 sq ft · 104 days on market Courtesy of LPT REALTY, LLC
- 7631 Long Island Dr $229,000 · 3 bd · 3 ba · 1,187 sq ft · 106 days on market Courtesy of ORCHARD BROKERAGE, LLC
Checked against the MLS Oct 16, 2026. All new listings in this market.
Every Home for Sale in Crestwynd Bay Kissimmee Right Now (8)
All 8 active and pending Crestwynd Bay Kissimmee listings with a detail page, newest first, refreshed twice a day from the MLS.
- 2693 Andros Lane · $300,000 · 3 bd / 3 ba · listed Oct 6, 2026 · listed by Aura Homes, Llc.
- 2685 Andros Lane · $234,000 · 3 bd / 3 ba · listed Sep 5, 2026 · listed by Real Broker, Llc
- 2691 Andros Lane · $259,000 · 3 bd / 2.5 ba · listed Aug 15, 2026 · listed by Keller Williams Realty At The Parks
- 7601 Acklins Road · $269,000 · 3 bd / 2.5 ba · listed Aug 2, 2026 · listed by Lpt Realty, Llc
- 2682 Mayaguana Street · $290,000 · 3 bd / 2.5 ba · listed Jul 16, 2026 · listed by Florida Homes Realty & Mortgage
- 7631 Long Island Dr · $229,000 · 3 bd / 3 ba · listed Jul 16, 2026 · listed by Orchard Brokerage, Llc
- 2680 Mayaguana Street · $252,000 · 3 bd / 3 ba · listed Jul 16, 2026 · listed by Lpt Realty, Llc
- 2626 Andros Lane · $245,900 · 3 bd / 3 ba · listed Jul 16, 2026 · listed by Turnkey Homes Real Estate Corp
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Andros Lane (62 homes on record)
- Long Island Drive (29 homes on record)
Frequently Asked Questions
What is the median home price in Crestwynd Bay?
How long do homes in Crestwynd Bay take to sell?
Is Crestwynd Bay a buyer's or seller's market right now?
How many homes are in Crestwynd Bay?
What share of Crestwynd Bay is owner-occupied?
When were the homes in Crestwynd Bay built?
Who is the best real estate agent for Crestwynd Bay?
How do I find a top Kissimmee real estate agent who knows Crestwynd Bay?
Can Momentum Realty connect me with an agent for Crestwynd Bay?
Where is Crestwynd Bay, and what county is it in?
Is Crestwynd Bay in a flood zone?
Is Crestwynd Bay a good place to live?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 15, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (4 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2009 (74 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.
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More on Crestwynd Bay
- Home values · What homes in Crestwynd Bay actually sell for
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