Cinnamon Shores
Homes for Sale in Winter Park, FL
All 337 homes for sale in WINTER PARK, FL · median $664,900 · 150 homes for sale in 32789 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 6 closed sales in Cinnamon Shores in Winter Park, FL since 2007, the most recent in June 2026. Across Winter Park as a whole, 494 homes closed in the last 12 months at a median of $459,450, 34 median days on market, with 124 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $7,660 ($6,990 with the full homestead exemption).
Cinnamon Shores is a small, tightly held pocket of Winter Park - just 10 homes total, all built in a narrow window between 1981 and 1990, with a median build year of 1984. The homes themselves run large, with a median living area above 3,200 square feet, which puts this community in a different size category than most infill Winter Park product from the same era.
There are zero active listings as of this snapshot, and every home in the community carries homestead status, meaning the entire inventory is owner-occupied primary residences rather than rentals or investment holdings. That combination - small count, full homestead exemption, no listings on the market - tells you this is a community that turns over rarely. When something does list here, there is no comparable inventory sitting alongside it to anchor pricing, so each sale tends to get evaluated on its own terms.
Nearby homes for sale
No active listings inside Cinnamon Shores right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
A compact enclave of ten larger-format homes from the early-to-mid 1980s, Cinnamon Shores sits inside Winter Park with no current MLS-documented HOA amenities and no active listings at the moment - a community defined more by its scarcity than by any shared feature set.
Stellar MLS sales records identify 9 homes in Cinnamon Shores that have changed hands since 2014, built between 1981 and 2013 (median 1984), with a median living area of about 3,286 sq ft and a typical 4-bedroom, 3.5-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Cinnamon Shores is best for.
Best for
- A buyer who wants a larger 1980s-era home and is willing to wait for the rare listing to appear
- A long-term buyer planning to homestead the property, matching the community's ownership pattern
- A buyer prioritizing location within Winter Park over community amenities or a clubhouse package
Probably not for
- A buyer who wants to compare several active listings within the same community before making an offer
- A buyer specifically seeking HOA-run amenities like a pool, gym, or clubhouse
- An investor looking for rental turnover, given the community's full homestead occupancy pattern
The market around Cinnamon Shores
Cinnamon Shores is too small for its own price trend, so here is the market around it.
In ZIP 32789, 244 homes are on the market and 25% are under contract — a steady corner of Winter Park.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
In ZIP 32789 (WINTER PARK), 394 homes closed in the last 12 months at a median of $635K ($396/sq ft), up 7.4% year over year, with a median 40 days on market. Right now 88 active and 21 pending listings put supply at about 4.9 months - a balanced market. See the live ZIP 32789 housing market and the Orange County market.
ZIP and county figures describe the wider market, not Cinnamon Shores specifically. Momentum Research analysis of MLS records.
The Cinnamon Shores buying strategy.
If we were buying in Cinnamon Shores 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 Cinnamon Shores.
Ten homes, one era, no visible market
With only 10 homes in the entire community and zero currently active, Cinnamon Shores does not behave like a typical subdivision with a running inventory of comparable sales. Buyers interested in this pocket of Winter Park need to think in terms of years, not weeks, when it comes to opportunity - a listing here is an event, not a routine occurrence.
The homes themselves share a build era (1981 - 1990, median 1984) and a size profile well above the median for many nearby communities, with living areas centered around 3,252 square feet. That places Cinnamon Shores in the larger-home tier for its vintage. No community amenities are documented in current MLS listings, so whatever draws a buyer here is the home and the location itself, not a shared clubhouse, pool, or recreational package.
The location and the amenities are priced into every listing in Cinnamon Shores. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
A 10-home community with no active listings is not a place you can shop with typical search tools - there is nothing to browse. Momentum tracks ownership and homestead patterns in pockets like this specifically so we can reach out before a home is publicly marketed, and so a seller here understands they are not competing against a shelf of similar listings when they price a home.
Cinnamon Shores in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
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 Cinnamon Shores 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 Cinnamon Shores sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Cinnamon Shores, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Cinnamon Shores home worth?
Get a no-obligation home value based on real comparable sales in Cinnamon Shores, 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 Winter Park →
Should you buy in Cinnamon Shores?
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 12, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2007 (6 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 Cinnamon Shores fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Cinnamon Shores
Where is Cinnamon Shores?
Cinnamon Shores is a community in WINTER PARK, Orange County, Florida, ZIP 32789.
Are there homes for sale in Cinnamon Shores right now?
No active listings inside Cinnamon Shores at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Cinnamon Shores have an HOA or CDD?
No HOA is on record for Cinnamon Shores in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Nearby Communities
Explore more neighborhoods near Cinnamon Shores with Momentum Realty’s local guides.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Orange County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Orange County scorecard.
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.
CINNAMON SHORES Market Scorecard
CINNAMON SHORES is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 32789 ZIP is $809,773, about 61.9% above 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.