Montego Bay
Homes for Sale in Kissimmee, FL
All 3,084 homes for sale in Kissimmee, FL · median $375,000 · 801 homes for sale in 34746 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
As of October 2026, Montego Bay in Kissimmee, FL has 1 home for sale. Over the 12 months ending 2026-08-02, 4 recorded sales closed at a median of $345,000, $226 per square foot, a median 37 days on market, sellers accepting 95% of original asking (-8% versus the prior year). Homes listed or recently sold were built 1989 - 1990; 8 of 8 report an HOA (median $38/mo); none of the 8 geocoded homes sit in a FEMA special flood hazard zone (median elevation 81 ft). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,260 ($4,650 with the full homestead exemption).
Last 30 days in Montego Bay: 2 new listings (median asking $359,450). As of October 17, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Homes For Sale Right Now in Montego Bay
Live MLS inventory for Montego 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 and pending Montego Bay listings as of 2026-10-17, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2004 through 2026. Tap any home to ask about it.
Montego Bay right now
🟡 Balanced market. 2.4 months of supply and 67% 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 August 2, 2026. Confidence: Medium (3 active and pending listings, 4 closed sales in 12 months).
🔴 Off the recent peak. The trailing-12-month median ($345K) is down 8.0% from the prior 12 months ($375K). 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 August 2. Confidence: Low (4 and 7 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 18, 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
Montego Bay market snapshot (as of August 2, 2026): the median sale price is about $345K ($226 per sq ft over the trailing 12 months of closed sales), a median 38 days on market for closed sales, and 2.4 months of supply, a balanced market. The trailing-12-month median is down 8% from the prior 12 months, computed from record-level Stellar MLS closed sales (4 closings in the current window).
In ZIP 34746 (Kissimmee), 1,623 homes closed in the last 12 months at a median of $405K ($199/sq ft), down 4.3% year over year, with a median 67 days on market. Right now 435 active and 80 pending listings put supply at about 6.7 months - a buyer's market. See the live ZIP 34746 housing market and the Osceola County market.
Montego Bay is a community of 207 homes in Kissimmee, Osceola County, built between 1989 and 1991 (median 1990), with a median living area of about 1,851 square feet. 57% 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 Montego Bay. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Montego BayPhotos from Stellar MLS listings in Montego 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 August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($345K) IS the median in the snapshot above, and the move from 2025 ($375K) IS the -8.0% one-year change.
Windows contain 0 to 14 sales each (4 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.
17% of homes for sale in ZIP 34746 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 (2026-10-18).
Montego Bay Market Scorecard
Montego Bay is currently a balanced market. About 2.4 months of supply, a median asking price of $354,900, and homes go under contract in about 19 days.
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.
Montego 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 Montego Bay
- Playground · reported on 5 of 5 listings
- Pool · reported on 5 of 5 listings
- Tennis Court(s) · reported on 5 of 5 listings
- Recreation Facilities · reported on 3 of 5 listings
- Park · reported on 3 of 5 listings
- Basketball Court · reported on 2 of 5 listings
- Pickleball Court(s) · reported on 1 of 5 listings
- Racquetball · reported on 1 of 5 listings
- Deed Restrictions · reported on 1 of 5 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
- Celebration K-8 · Elementary
- Celebration K-8 · Middle
- Poinciana High School · High
Zoned schools reflect the assignments reported on recent Montego 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 Montego Bay address.
Shop the zone: Homes zoned for Poinciana High School
Recent Developments in Montego Bay
Development, infrastructure, retail, and school activity affecting Montego 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 4 miles north of Montego 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 17 miles east of Montego Bay, elsewhere in Osceola County.
Source: Spectrum News 13 - 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 6 miles northwest of Montego 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 13 miles southeast of Montego 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 Montego Bay buying strategy.
If we were buying in Montego 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.
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 Montego Bay.
A closer look at the Montego Bay market
At a median of $226 per square foot, Montego 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 2.4 months of supply, a balanced market and the trailing-12-month median down 8% year over year. Homes that do trade take a median 38 days on market, useful leverage on any listing that has lingered.
The housing stock is 207 homes built between 1989 and 1991, and 57% 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 Montego 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 Montego 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 (6.1). Basis: Recent Direction -8.0% year-over-year; Liquidity & Demand 2.4 months of supply; Owner Commitment 57% owner-occupied; Pricing Power 95.5% sale-to-list. Refreshed with each data update.
What it really costs to own in Montego 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 $456/year (about $38/month) across 236 MLS listings (most billed annually; 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. |
| Roof and age | Median build year 1990 across 8 listings. An original roof here would be about 36 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 Montego 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 Montego Bay
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Montego Bay will answer, and the answer is published on this page for the next buyer.
HOA, CDD & Fees
- HOA dues reported around $456/year (about $38/month) · median of 236 MLS listings, most billed annually
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $456 a year ($38 a month) - the median AssociationFee across 236 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 Montego 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 Montego Bay sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Montego 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 Montego Bay home worth?
Get a no-obligation home value based on real comparable sales in Montego 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 MONTEGO BAY
Homes in MONTEGO 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. 2 on record.
- 4840 Kingston Circle · off market
- 4865 Kingston Circle · off market
| Location | Kissimmee, Osceola County, FL · ZIP 34746 |
|---|---|
| Homes in the community | 207 (FL DOR 2025 assessment roll) |
| Years built | 1989–1991 (median 1990) |
| Typical living area | 1,851 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Amenities listed by sellers | Playground, Pool, Tennis Court(s), Basketball Court, Park, Recreation Facilities |
| Sale prices, last 12 months | $345,000 median across 4 closed sales · $226 per sq ft · -8.0% vs the prior 12 months |
| Days on market (closed sales) | 37 median |
| For sale right now | 1 active, 2 pending · median asking $354,900 · 2.4 months of supply |
| Owner-occupied (homestead) share | 57% |
Data as of August 2, 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, “Montego Bay key facts,” movewithmomentum.com/neighborhoods/montego-bay-kissimmee, data as of August 2, 2026.
Housing distress & ownership in MONTEGO 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 Montego Bay
The newest homes for sale in Montego Bay right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 4858 Kingston Circle $359,000 · 3 bd · 2 ba · 1,611 sq ft · 14 days on market Courtesy of MY REALTY GROUP, LLC.
- 2504 Kingston Court $359,900 · 3 bd · 2 ba · 1,565 sq ft · 19 days on market Courtesy of REMAX PREMIER PROPERTIES
- 4805 Kingston Cir $350,000 · 3 bd · 2 ba · 1,381 sq ft · 126 days on market Courtesy of LPT REALTY, LLC
Checked against the MLS Oct 18, 2026. All new listings in this market.
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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.
- Montego Bay Boulevard (75 homes on record)
- Kingston Circle (27 homes on record)
Frequently Asked Questions
What is the median home price in Montego Bay?
How long do homes in Montego Bay take to sell?
Is Montego Bay a buyer's or seller's market right now?
How many homes are in Montego Bay?
What share of Montego Bay is owner-occupied?
When were the homes in Montego Bay built?
Do cash buyers compete in Montego Bay?
Who is the best real estate agent for Montego Bay?
How do I find a top Kissimmee real estate agent who knows Montego Bay?
Can Momentum Realty connect me with an agent for Montego Bay?
Where is Montego Bay, and what county is it in?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 17, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (3 streets, ZIP 34746)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2004 (86 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?
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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 MONTEGO BAY fits the bigger picture — live prices, inventory, and Momentum Scores:
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More on Montego Bay
- Home values · What homes in Montego Bay actually sell for