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Overview

4 bd3 ba2,021 sqft2 car garageSingle Family
TypeSingle Family
HOA$305/yr
Built1984
Lot10,542 sqft
Living area2,021 sqft
Price / sqft$181
Garage2 car

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

High CeilingsPrimary Bedroom Main FloorThermostatPrivate YardSidewalkDeed RestrictionsSidewalksStreet Lights

2704 Winding Ridge Ave S is a 1984-built home in Shadow Bay Unit 2, Kissimmee. Inside you'll find 4 bedrooms, 3 bathrooms, and 2,021 square feet of living space. Listed at $365,000 (about $181/sqft), 5 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $305 annually.

From the listing

Not every house needs to be brand new to be the right house. Sitting on a quiet cul-de-sac in Shadow Bay, this 4-bedroom, 3-bath pool home has more than 2,000 square feet, a layout with personality, and plenty of room for the next owner to make it their own. Vaulted ceilings, exposed wood beams and an open staircase give the main living spaces architectural character you simply don’t find in every home. The first floor includes the primary suite plus an additional bedroom and full bath, while two more bedrooms and a third bath are upstairs, creating a flexible layout for family, guests or a home office. Out back, a large screened-in pool and covered patio take center stage, with a fenced backyard and plenty of space to enjoy Florida living. The home also offers a two-car garage, new fencing installed in 2022 and a new roof installed in 2020, taking two meaningful exterior items off the future to-do list. And a refreshingly low HOA of only $305 per year. The location puts you close to the best of Kissimmee, with easy access to US-192, shopping, dining, schools and major roadways, plus Walt Disney World and Orlando’s attractions within easy reach. This isn't a cookie-cutter renovation where someone else chose every finish for you. It's a home with good bones, real square footage and plenty of potential for someone ready to bring their own vision to it. Update a little at a time or come in with a plan and make it entirely your own. Either way, the space, pool, layout and location give you a solid place to start.

The essentials

Built
1984
Price / sqft
$181
On market
5 days
Annual tax
$5,759
HOA
$305/yr
Flood zone
X · Low risk
Lot
10,542 sqft
Type
Single Family Residence

At a glance

Single family
Built 1984
Private pool
Deck
2 car garage
Driveway
10,542 sqft lot
Lot size
2,021 sqft
Living area

Payment

Est. monthly payment
$2,592/mo
Down payment (20%)
$73,000
Property taxes
$480/mo
HOA
$305/yr
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1984
Lot
10,542 sqft
Cooling
Central Air
Heating
Central, Electric
Parking
Driveway, Garage Door Opener
Pool
Deck, In Ground, Screen Enclosure
Days on Market
5
High Ceilings
Primary Bedroom Main Floor
Thermostat
Private Yard
Sidewalk
Deed Restrictions
Sidewalks
Street Lights
Dishwasher
Microwave
Range
Refrigerator
Elementary
Kissimmee Elem
Middle
Kissimmee Middle
High
Osceola High School

Districts can re-zone, so verify directly with the district before relying on these.

Flood Zone X
Annual Tax (2025)
$5,759
Parcel #
17-25-29-2136-0001-0620

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Shadow Bay Unit 2
County
Osceola
MLS Area
34741 - Kissimmee (Downtown East)
Lot Size
10,542 sqft
In CountyLandscapedSidewalkPaved
HOA
$305/yr
Shadow Bay Community Association/Ms. Le Nguyen

Price history

Date
Event
Price
10/5/2026
Listed for sale
Source: Stellar MLS #O6447274
$365,000
$181/sqft

Neighborhood

2704 Winding Ridge Ave S
Kissimmee, FL, 34741 · 34741 - Kissimmee (Downtown East)

Market insights

Offer Insights

Choose an offer strength

List price: $365,000
$362,500 – $365,000
99.5% – 100% of listTops out right at the list price
80% of listList price
82 of the last 148 home closings in 34741 landed at this number or higher (55%). The median one sat 34 days before it went under contract, and this one is on day 5.

Sample: 148 closed home sales in 34741 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

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Calculator

Est. monthly payment
$2,591/mo
Principal & interest$1,904
Property taxes$480
Insurance$183
HOA$25
Down payment20% · $73,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA is the fee reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$365,000

$181 per sq ft

Beds and baths

4 beds, 3 baths

Size

2,021 sq ft

Time on market

5 days

Year built

1984

Monthly payment

About $2,592/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $5,759 annual tax bill, insurance, and the $305/yr HOA fee.

HOA fee

$305/yr

Managed by Shadow Bay Community Association/Ms. Le Nguyen.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

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Brokered byREAL BROKER, LLCListing agent: Chad VaughanListing data from Stellar MLS, MLS# O6447274.

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