Maitland Shores
Homes for Sale in Winter Park, FL
All 356 homes for sale in WINTER PARK, FL · median $697,000 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-09-20, 3 recorded sales closed at a median of $1,650,000, $508 per square foot, a median 160 days on market, sellers accepting 86% of original asking. Homes listed or recently sold were built 1953 - 1979; none of the 3 geocoded homes sit in a FEMA special flood hazard zone (median elevation 77 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $27,510 ($26,840 with the full homestead exemption).
| Location | WINTER PARK, Orange County, FL · ZIP 32751, 32789 |
|---|---|
| Homes in the community | 195 (FL DOR 2025 assessment roll) |
| Years built | 1919–2024 (median 1985) |
| Typical living area | 3,718 sq ft (median) |
| Amenities listed by sellers | Park, Playground, Tennis Court(s) |
| Sale prices, last 12 months | $1,650,000 median across 3 closed sales · $508 per sq ft |
| Days on market (closed sales) | 160 median |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 72% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2004 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Maitland Shores key facts,” movewithmomentum.com/neighborhoods/maitland-shores-winter-park, data as of September 20, 2026.
Maitland Shores sits on the Winter Park side of the county line, a small, established pocket of 195 homes with a median build year of 1985 and a wide age range that runs from 1919 to as new as 2024. That spread means condition, layout, and lot placement drive value far more than a single benchmark year - a rebuilt 1985 home and an original one can present very differently despite an identical age on paper.
There are zero active listings in this community as of this snapshot, which tells its own story: this is not a market with inventory sitting and waiting. When something here does list, it tends to move through a thin buyer pool watching this specific pocket rather than a broad open market. Sellers should expect to price against recent comparable closings rather than current competition, and buyers should be ready to act with pre-approval and a clear sense of what they want before a listing appears.
Nearby homes for sale
No active listings inside Maitland 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
Maitland Shores market snapshot (as of September 20, 2026): the median sale price is about $1.65M ($508 per sq ft over the trailing 12 months of closed sales), and a median 160 days on market for closed sales.
In ZIP 32751 (WINTER PARK), 301 homes closed in the last 12 months at a median of $470K ($261/sq ft), down 1.0% year over year, with a median 31 days on market. Right now 34 active and 17 pending listings put supply at about 3.4 months - a healthy market. See the live ZIP 32751 housing market and the Orange County market.
County records show 18 qualified sales in Maitland Shores across 2024 - 2025 (11 in 2024, 7 in 2025), median $1.09M - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Maitland Shores is a community of 195 homes in Winter Park, Orange County, built between 1919 and 2024 (median 1985), with a median living area of about 3,718 square feet. 72% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
A modest-sized, long-established community in Winter Park with a broad range of build years and a homestead share of about 72%, pointing to a base of owner-occupied homes rather than heavy investor or rental turnover.
The setting & the homes.
Aerial and on-site photos of Maitland Shores. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Photos from Stellar MLS listings in Maitland Shores; content deemed reliable but not guaranteed.
Who Maitland Shores is best for.
Best for
- Buyers who want a larger living footprint and are willing to wait for the right listing rather than choose from current inventory
- Buyers focused on a specific Winter Park location and comfortable evaluating homes on a case-by-case, condition-driven basis given the wide build-year range
- Buyers who move decisively once a home lists, since this community currently shows no active inventory to shop
Probably not for
- Buyers who want to compare several active listings side by side before committing
- Buyers seeking a uniform, single-era housing stock rather than a mix spanning 1919 to 2024
- Buyers who need firm, HOA-confirmed amenity details before making an offer, since current amenity notes are self-reported through listings
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 ($1.65M) IS the median in the snapshot above.
Windows contain 0 to 3 sales each (3 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 2004 through 2026. Deemed reliable but not guaranteed.
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.
32% of homes for sale in ZIP 32751 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 (2026-09-20).
Maitland Shores Market Scorecard
Maitland Shores is currently a balanced market..
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in Maitland Shores, WINTER PARK
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.
Maitland Shores 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.
Life at Maitland Shores
- Park · reported on 1 of 2 listings
- Playground · reported on 1 of 2 listings
- Tennis Court(s) · reported on 1 of 2 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.
The Maitland Shores buying strategy.
If we were buying in Maitland 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 Maitland Shores.
A community built in layers, not in one push
With homes dating from 1919 through 2024, Maitland Shores was not built out in a single development cycle. That layering shows up in the housing stock itself: a median living area of 3,718 square feet suggests larger footprints are common here, but the century-plus build range means square footage, renovation history, and lot configuration will vary meaningfully from one address to the next even within the same block.
The community amenities on record - a park, a playground, and tennis courts - are reported across MLS listings rather than confirmed through a current HOA document, so treat them as a starting point for questions rather than a guarantee. With zero active listings at this snapshot, there is no current inventory to walk and compare directly; anyone serious about this pocket should be working from recent sold data and be positioned to move quickly once something surfaces.
The location and the amenities are priced into every listing in Maitland Shores. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
A community with no active listings and a wide build-year range is not one you can price or evaluate from a portal search. We track closed activity in Maitland Shores directly, verify amenity and HOA details before they matter, and help buyers get positioned to move the moment something in this pocket does list.
Maitland Shores in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $8/month · median of 22 MLS listings, most billed annually
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $8 per month - the median AssociationFee across 22 MLS records, normalised to a monthly figure; most are billed annually. 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.
Tools for a Maitland 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 Maitland Shores sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Maitland 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 Maitland Shores home worth?
Get a no-obligation home value based on real comparable sales in Maitland 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 →
Recently off market in Maitland Shores
Homes in Maitland Shores 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.
- 2299 Via Tuscany · off market
Frequently Asked Questions
What is the median home price in Maitland Shores?
How long do homes in Maitland Shores take to sell?
How many homes are in Maitland Shores?
What share of Maitland Shores is owner-occupied?
When were the homes in Maitland Shores built?
Who is the best real estate agent for Maitland Shores?
How do I find a top Winter Park real estate agent who knows Maitland Shores?
Can Momentum Realty connect me with an agent for Maitland Shores?
Where is Maitland Shores, and what county is it in?
Should you buy in Maitland 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: October 1, 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 (6 streets, ZIP 32751/32789)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2004 (27 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 Maitland Shores fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Maitland Shores with Momentum Realty’s local guides.