How can I find Winter Park townhomes for sale within my budget?

Use the price ranges above to browse current townhome listings under $500,000, from $500,000 to under $750,000, or $750,000 and above. Available listings can change. Alongside the asking price, review association dues, maintenance responsibilities and any special assessments before deciding which homes to shortlist.

Can a townhome also be a condominium?

Yes. Townhome describes a building form, while condominium describes an ownership arrangement. A multistory townhome can therefore be condominium-owned. Rather than treating the two labels as opposites, check the property's layout and ownership documents together. Those details establish what you would own and what is shared, helping you compare homes on their actual arrangements rather than relying on a listing category alone.

Does townhome ownership mean less exterior maintenance?

Not automatically. Exterior maintenance depends on the responsibilities assigned to you and the association in the relevant documents. An association may handle certain tasks, but the townhome label does not establish which ones. Before choosing a home, identify the work you would still need to arrange yourself. This is especially useful for second-home planning, when you may be away for periods of time.

Are HOA dues included in the mortgage payment?

Association dues are generally paid separately from your mortgage payment. Include them as a distinct recurring expense when comparing homes, and check the association documents for what they cover. Special assessments are separate from regular dues and can create additional obligations. Looking at dues, maintenance responsibilities and assessments together gives you a clearer picture than comparing the dues amount alone.

What should I check when buying a Winter Park townhome as a second home?

Check the property's location, layout and ownership documents against how you plan to use it. Confirm which maintenance tasks remain yours, what you would need to arrange while away and which rules apply to the home. We can help you compare listings and identify questions to resolve before you choose.

How can Gaby help with Winter Park townhomes for sale?

Share your budget, preferred layout and timing. Gaby can compare current homes, arrange viewings and help you assess condition, private space and ownership obligations.

Winter Park, Florida

Winter Park homes for sale: townhomes

Compare the actual layout and ownership obligations. Review Winter Park townhomes for sale.

Understand the Home and the Ownership

Winter Park homes for sale include different ownership choices; this page focuses on Winter Park townhomes for sale. We help you compare the actual layout, condition, private space and ongoing costs. Match each property's layout and legal ownership form; a townhome design can have different maintenance arrangements from a similar-looking home.

Townhomes for Sale in Winter Park, FL

16 listings

232 days on market
$1,550,000Price increased by $55,000 on Sep 11, 2026
901 Enclave PlaceWinter Park, FL, 32792
- 4 beds
- 4 baths
- 2,738 sqft
232 days on market
$1,550,000Price increased by $55,000 on Sep 11, 2026
905 Enclave PlaceWinter Park, FL, 32792
- 4 beds
- 4 baths
- 2,756 sqft
142 days on market
$1,375,000Price reduced by $24,000 on Nov 7, 2026
512 W Swoope AvenueWinter Park, FL, 32789
- 3 beds
- 3 baths
- 2,585 sqft
112 days on market
$915,000Price reduced by $10,000 on Sep 29, 2026
1927 S Lakemont AvenueWinter Park, FL, 32792
- 3 beds
- 4 baths
- 2,093 sqft
69 days on market
$575,000
1259 Indiana AvenueWinter Park, FL, 32789
- 2 beds
- 3 baths
- 1,648 sqft
5 days on market
$650,000
1261 Michigan AvenueWinter Park, FL, 32789
- 3 beds
- 3 baths
- 1,798 sqft
8 days on market
$3,995,000
125 S Interlachen Avenue Unit 4Winter Park, FL, 32789
- 3 beds
- 5 baths
- 3,885 sqft
164 days on market
$2,995,000Price reduced by $155,000 on Oct 10, 2026
125 S Interlachen Avenue Unit 2Winter Park, FL, 32789
- 3 beds
- 5 baths
- 3,244 sqft
18 days on market
$695,000
2887 Temple TrailWinter Park, FL, 32789
- 2 beds
- 3 baths
- 1,801 sqft
100 days on market
$3,645,000Price reduced by $50,000 on Oct 29, 2026
125 S Interlachen Avenue Unit 1Winter Park, FL, 32789
- 3 beds
- 5 baths
- 3,878 sqft
135 days on market
$2,695,000Price reduced by $105,000 on Oct 1, 2026
660 W Morse BoulevardWinter Park, FL, 32789
- 3 beds
- 4 baths
- 3,286 sqft
53 days on market
$1,300,000
504 W Swoope AvenueWinter Park, FL, 32789
- 3 beds
- 3 baths
- 2,563 sqft
149 days on market
$774,900Price reduced by $35,100 on Oct 7, 2026
1265 Arlington PlWinter Park, FL, 32789
- 3 beds
- 4 baths
- 2,030 sqft
290 days on market
$680,000Price reduced by $15,000 on Sep 17, 2026
432 W Swoope AvenueWinter Park, FL, 32789
- 4 beds
- 4 baths
- 2,664 sqft
154 days on market
$2,625,000Price reduced by $70,000 on Aug 29, 2026
413 W Morse BoulevardWinter Park, FL, 32789
- 3 beds
- 4 baths
- 3,048 sqft
95 days on market
$575,000
1071 Aragon AvenueWinter Park, FL, 32789
- 2 beds
- 3 baths
- 1,851 sqft
Browse all listings16 listings

Explore townhomes for sale

Top Villas Intelligence

Review available property reports, ownership costs and nearby-sale comparisons. Report availability varies by home.

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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

Winter Park area-wide market snapshot

All property types in this area. Inventory and asking prices are area-wide; the property searches above may use narrower criteria.

For sale now: 199
Median asking price: $1,299,000

Recent sales near Winter Park

39 properties sold within half a mile in the last 12 months · median $1,100,000

See all sold

1818 Dover Road
3 bed · 2 bath · 1,873 sqft
$439,900
Sold Nov 6, 2026
1592 Arbor Park Drive
4 bed · 3 bath · 2,016 sqft
$700,000
Sold Oct 30, 2026
2015 Taylor Avenue
3 bed · 2 bath · 1,439 sqft
$401,200
Sold Oct 2, 2026
1597 Oakhurst Avenue
5 bed · 5 bath · 4,410 sqft
$2,925,000
Sold Sep 16, 2026

Winter Park Townhomes for Sale by Price

Browse townhomes under $500,000, $500,000 to under $750,000, or $750,000 and above. Compare association costs alongside asking prices.

Explore Everyday Life in Winter Park

These are public local facilities, not amenities included with a home. Check each property's location to see how they fit your routines.

Central Park: 11 Acres Downtown
On Park Avenue, oak canopy, fountains, a rose garden and community events offer reasons to spend time outdoors in the downtown shopping district.
Mead Botanical Garden: 47.6 Acres
A butterfly garden, boardwalk, bike trail and picnic tables offer options for outdoor time at this city park on South Denning Drive.
SunRail on West Morse Boulevard
Near Park Avenue and Central Park, the station offers Amtrak and bus connections for travel choices. Parking depends on city rules and availability.

Explore Winter Park on the Map

Use the area map to orient your search, then check each townhome's location against the places that matter to your daily routine.

Look Beyond the Asking Price

The asking price is only one part of comparing ownership costs. Association dues are generally paid separately from your mortgage payment, so consider them as a distinct recurring expense. Read the relevant documents to understand what those dues cover and which maintenance obligations remain yours. Review reserve funds and any information about special assessments, too. Regular dues and additional assessments are different obligations, and a lower dues figure alone does not tell you which home will cost less to own. Comparing the responsibilities alongside the charges gives each figure context. Before narrowing your shortlist, ask for clarification on any expense or maintenance duty that is unclear rather than assuming it is included.

What to Check Before Choosing a Townhome

Resolve these questions for each home on your shortlist. The answers shape daily living and second-home ownership, and can differ between properties.

How Is the Home Arranged?
Confirm the floor plan and shared-wall configuration from property-specific information. Does the arrangement suit how you expect to use the home?
Who Handles Maintenance?
Establish which maintenance tasks belong to you and which belong to the association. What would you need to arrange while away from a second home?
What Exterior Changes Are Allowed?
Review restrictions on exterior changes before planning improvements. Do the documented rules fit the ways you want to personalize your home?
Which Facilities Are Shared?
Confirm which shared facilities exist and the association's responsibilities for them. Would you use those spaces as part of your everyday routine?

Winter Park Townhomes for Sale: FAQs

Connect your Winter Park shortlist

Compare Winter Park condos by legal ownership, shared obligations and maintenance rather than the exterior alone. Winter Park new construction offers a separate construction-stage search. Our Winter Park neighborhood comparison and Winter Park homes for sale hub help you weigh the location alongside the home format.

Gaby Sadler

Property Specialist, Serhant

Find Winter Park townhomes for sale with Gaby

Tell me your budget and plans. I'll help compare Winter Park homes for sale that match this townhome search, including layout, condition and ownership costs.

+1 (407) 490-0475 realty@thetopvillas.com

Find a Townhome That Fits Your Plans

Compare Winter Park condos for another attached-home option, or new construction homes if you prefer a newly built property. The Winter Park neighborhood comparison helps you weigh locations alongside ownership and maintenance arrangements.

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