Maitland Shores
Homes for Sale in Winter Park, FL
All 356 homes for sale in WINTER PARK, FL · median $697,000 · 167 homes for sale in 32789 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, Maitland Shores First Add in Winter Park, FL has 4 homes for sale. Homes listed or recently sold were built 1953 - 2025 with 1 new construction; none of the 7 geocoded homes sit in a FEMA special flood hazard zone (median elevation 80 ft).
| Location | WINTER PARK, Orange County, FL · ZIP 32789 |
|---|---|
| Homes in the community | 56 (FL DOR 2025 assessment roll) |
| Years built | 1925–2024 (median 2001.0) |
| Typical living area | 3,692 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Amenities listed by sellers | Closed Circuit Camera(s), Security System |
| For sale right now | 4 active, 1 pending · median asking $3,459,975 · 24.0 months of supply |
| Owner-occupied (homestead) share | 75% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2014 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Maitland Shores First Add key facts,” movewithmomentum.com/neighborhoods/maitland-shores-first-add-winter-park, data as of September 20, 2026.
Last 30 days in Maitland Shores: 2 new listings (median asking $3,474,995), 1 under contract right now, 1 closed sale (median $2,600,000). As of October 5, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Homes For Sale Right Now in Maitland Shores
Live MLS inventory for Maitland Shores. 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 Maitland Shores listings as of 2026-10-01, 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 Maitland Shores First Add Winter Park Right Now (4)
All 4 active and pending Maitland Shores First Add Winter Park listings with a detail page, newest first, refreshed twice a day from the MLS.
- 913 Moss Lane · $950,000 · 3 bd / 2 ba · listed Sep 15, 2026 · listed by Vector Realty
- 952 Moss Lane · $1,319,950 · 4 bd / 3.5 ba · pending · listed Sep 11, 2026 · listed by Meridian Reside
- 2661 Via Tuscany · $5,999,990 · 4 bd / 4.5 ba · listed Sep 9, 2026 · listed by Coldwell Banker Realty
- 2228 Azalea Place · $5,600,000 · 5 bd / 5.5 ba · listed Jul 15, 2026 · listed by Compass Florida Llc
Maitland Shores right now
🟢 Buyer-leaning market. 24.0 months of supply and 20% 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 (5 active and pending listings, 2 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 5, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
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.
The market around Maitland Shores
Maitland Shores is too small for its own price trend, so here is the market around it.
In ZIP 32789, 239 homes are on the market and 23% are under contract — a steady corner of Winter Park.
Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).
ZIP and county figures describe the wider market, not Maitland Shores specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in Maitland Shores First Add, 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.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Dommerich Elem · Elementary
- Maitland Middle · Middle
- Winter Park High · High
Zoned schools reflect the assignments reported on recent Maitland Shores 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 Maitland Shores address.
Shop the zone: Homes zoned for Winter Park High High School
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.
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 Maitland Shores.
A closer look at the Maitland Shores market
Inventory runs at 24.0 months of supply, a buyer-leaning market.
The housing stock is 56 homes built between 1925 and 2024, and 75% 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 Maitland Shores. The deal is won or lost on condition, the comps, and the renovation math.
HOA, CDD & Fees
- HOA dues reported around $10/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 $10 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 First Add
Homes in Maitland Shores First Add 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.
- 948 Poinciana Lane · off market
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.
25% of homes for sale in ZIP 32789 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 (2026-10-04).
Frequently Asked Questions
Is Maitland Shores a buyer's or seller's market right now?
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?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 1, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 32789)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2014 (21 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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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Maitland Shores First Add fits the bigger picture — live prices, inventory, and Momentum Scores:
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