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Active · Single Family

248 CHESHIRE COURT

KISSIMMEE, FL 34758

Beds
4 beds
Baths
2 baths
Area
1,695 sqft
Single FamilyBuilt 20227,710 sqft lot2-car garageCentral, ElectricCentral Air$177/sqft469 days on market

About this home

Virtually Staged. Spacious 4-Bedroom Retreat on a Quiet Cul-de-Sac – Your Kissimmee Dream Home Awaits! Welcome to 248 Cheshire Court, a beautifully maintained home nestled on a peaceful cul-de-sac in the heart of Kissimmee. This charming 4-bedroom, 2-bathroom property offers a spacious open layout with plenty of natural light, perfect for comfortable family living and entertaining. Enjoy a modern kitchen with ample cabinetry, a generous master suite with a private bath, and a large backyard — ideal for outdoor relaxation or weekend BBQs. Conveniently located near schools, shopping, dining, and major roadways for an easy commute to Orlando and nearby attractions. Don’t miss your chance to own this move-in-ready gem — schedule your private tour today! Photos are of a model home that is very similar. Not actual home.

Facts & features

Interior

Bedrooms
4
Bathrooms
2
Living area
1,695 sqft
Heating
Central, Electric
Cooling
Central Air
Flooring
Ceramic Tile
Features
Ceiling Fans(s), Living Room/Dining Room Combo, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Walk-In Closet(s)
Appliances
Dishwasher, Disposal, Electric Water Heater, Microwave, Range

Exterior & lot

Lot size
7,710 sqft (0.18 ac)
Roof
Shingle
Construction
Block
Exterior
Sliding Doors

Parking

Garage
2 spaces

Financial

HOA dues
$90 / annually
Annual tax
$4,038 (2024)
Price / sqft
$177/sqft

Utilities

Water
Public
Sewer
Private Sewer
Utilities
Cable Available, Electricity Available, Sewer Available, Water Available

Property

Property type
Single Family
Year built
2022
Subdivision
POINCIANA VILLAGE 02 NEIGHBORHOOD 01
County
Osceola

Listing

Status
Active
Days on market
329 days
MLS #
MFR758389131
Source
Stellar MLS

Listed by Jacob Hara · TRANSCEND REALTY

Listing data provided by Stellar MLS. Information deemed reliable but not guaranteed.

RRENA ValiQRENA ValiQ is an estimated value, blended from public sale comps, neighbourhood trend and this listing’s own metrics. It is a reference, not a guaranteed or asking price. The final number moves on diligence, terms and timing.Estimate

Sample estimate — not an appraisal

$305k
+1.8% vs asking
$287k low$323k high

Based on 20 comparable sales within 4 miles of KISSIMMEE, FL, this home is priced under RENA ValiQ.

Reference only. Estimates blend public sale comps, neighbourhood trend and the listing’s own metrics. Final price moves on diligence, terms and timing — RENA is your second read, not your agent.

Estimate your monthly cost

PITI + HOA
Estimated monthly payment$2,059/mo
Principal & interest
$1,514/mo
Property tax
$337/mo
Home insurance
$200/mo
HOA dues
$8/mo

Opens at 20% down over 30 years at 6.5%, the same assumptions as the answers below. Property tax is this listing's own bill; insurance is left out until you enter a quote, because Florida premiums turn on roof age, elevation and carrier. Every field is editable.

Ask about this property

Answered from this listing’s own figures and the sales around it.

Price history

From the property’s MLS record.

DateEventPriceChange
Jul 27, 2026Price reduced$299,500−$30,450
May 5, 2025Listed$329,950

NeighbourhoodSample data

Reference scores for KISSIMMEE, FL. Schools, mobility and amenities feed live data once the dedicated provider connection lands.

Walk Score
82/ 100
Very walkable
Transit Score
50/ 100
Good transit
Bike Score
65/ 100
Bikeable
Elementary school
Not listed
Not named in the MLS record for this home
Middle school
Not listed
Not named in the MLS record for this home
High school
Not listed
Not named in the MLS record for this home

Location

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