What should I set aside besides the down payment?

Allow for closing costs, inspections, moving and urgent repairs. If you’re financing the purchase, ask your lender for an estimate of the cash you’ll need at closing and decide how much you want to keep in reserve.

How can I compare homes with similar asking prices?

Use a monthly estimate for each address. Add any mortgage payment, estimated property taxes, insurance, utilities and association dues. Set aside an amount for upkeep based on what you would be responsible for maintaining.

What if I can’t find a home within my budget?

Decide what you could trade, such as a larger yard, extra storage or a shorter commute. Compare the options against the same monthly budget, including dues, upkeep and regular travel costs.

What should I check when a home has low association dues?

Ask what the dues cover, who pays for major repairs and whether any special assessments have been approved or discussed. Review the association budget and recent meeting minutes for planned work that could affect your costs.

How can I tell if a fixer-upper fits my budget?

Use the inspection report and written repair estimates to separate urgent work from upgrades you can defer. Compare the asking price plus urgent repairs with the price of a home that needs less work, and leave room for unexpected costs.

Can I budget using the seller’s tax and insurance bills?

Use them as a starting point. Ask for a property tax estimate based on your purchase and get an insurance quote for the address. Compare homes using those figures.

Illustrative Central Florida home exterior with pale stucco walls, a covered entrance, a paved walkway and mature trees surrounding a landscaped lawn.

Winter Garden, Florida

Winter Garden Homes for Sale by Lowest Asking Price

Start with Winter Garden's lowest asking prices. Compare homes, ownership arrangements and the practical costs of your shortlist.

Winter Garden homes: lowest asking prices first

186 listings

4 days on market
$163,000
Bank owned (REO)
373 Eron Way Unit 47Winter Garden, FL, 34787
- 2 beds
- 2 baths
- 840 sqft
107 days on market
$188,000Price reduced by $11,999 on Oct 21, 2026
93 Windtree Lane Unit 102Winter Garden, FL, 34787
- 2 beds
- 2 baths
- 918 sqft
17 days on market
$189,000
87 Windtree Lane Unit KWinter Garden, FL, 34787
- 2 beds
- 2 baths
- 918 sqft
136 days on market
$199,999Price reduced by $15,001 on Sep 18, 2026
397 Eron Way Unit 42Winter Garden, FL, 34787
- 3 beds
- 2 baths
- 930 sqft
87 days on market
$199,999
844 Klondike StreetWinter Garden, FL, 34787
- 1 bed
- 1 bath
- 1,300 sqft
176 days on market
$204,900
170 Windtree LaneWinter Garden, FL, 34787
- 2 beds
- 2 baths
- 918 sqft
66 days on market
$204,900Price reduced by $7,100 on Sep 13, 2026
1315 Eastern Pecan Place Unit 202Winter Garden, FL, 34787
- 1 bed
- 1 bath
- 942 sqft
129 days on market
$214,000Price reduced by $10,000 on Aug 13, 2026
Short sale
359 Douglas Way Unit 54Winter Garden, FL, 34787
- 2 beds
- 2 baths
- 930 sqft
306 days on market
$218,000
92 Windtree Lane Unit 201Winter Garden, FL, 34787
- 2 beds
- 2 baths
- 918 sqft
59 days on market
$230,000
988 Stucki TerraceWinter Garden, FL, 34787
- 3 beds
- 3 baths
- 1,216 sqft
158 days on market
$239,000Price reduced by $3,000 on Oct 22, 2026
200 Southern Pecan Circle Unit 206Winter Garden, FL, 34787
- 2 beds
- 2 baths
- 1,276 sqft
81 days on market
$254,000Price increased by $30,000 on Oct 31, 2026
300 Eron Way Unit 1Winter Garden, FL, 34787
- 2 beds
- 2 baths
- 840 sqft
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Gross rental revenue

$118,400

74% projected occupancy

Breaks even at 27% occupancy

Annual income and costs

Gross rental revenue$118,400
Booking commission (18%)−$21,300
HOA and CDD fees−$9,800
Property tax−$11,200
Insurance−$6,400
Utilities and upkeep−$7,800
Operating income$61,900

Price per sq ft against nearby sales

8% below nearby sales

MedianThis home

$240$340

Operating income

$61,900

Operating yield

7.2%

Operating income

$61,900

per year

This home

$268 /sq ft

High confidence

Fixed ownership costs

$35,200

Nearby median

$292 /sq ft

What this search includes

Winter Garden homes for sale are ordered from lowest to highest asking price in this search, with no fixed price ceiling. We help you compare the layout, condition and ownership obligations behind each asking price. Matching homes use the saved Winter Garden area and require at least one listed bedroom; the search can include condos, townhomes and detached homes.

Use all Winter Garden homes for sale to return to the main area hub. A mailing address alone does not define this saved map.

Find the lowest asking prices first

This page orders matching Winter Garden homes from lowest to highest asking price without imposing a fixed price ceiling. It includes homes with at least one listed bedroom across property types, so compare ownership form as well as the headline price.

Four checks for your Winter Garden shortlist

Usable rooms and storage
Check room dimensions, bedroom placement and storage against the way you plan to live.
Parking and daily routes
Check parking arrangements and test journeys from the exact address to your regular destinations.
Condition and upkeep
Review the property's condition and distinguish essential work from changes you would simply prefer.
Ownership commitments
Request the association information and compare recurring charges and maintenance responsibilities.

Compare affordability beyond the asking price

Start with the least expensive homes, then review their usable space, condition and ongoing commitments. A lower-priced condo and a detached home may have very different maintenance arrangements. If you have a firm maximum, use a budget search to narrow the list.

Compare the commitments for each address

Ask which parts of the property you would maintain and which are managed through an association. Request the relevant documents and clarify any separate charges or restrictions before choosing a home. The asking-price filter does not establish rental permission or amenity access.

Our Winter Garden HOA fees and ownership costs guide offers a useful place to continue your comparison.