Winter Park FL Single Family Homes for Sale

4 Beds ⋅ 4 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code

Winter Park - Located in the gated community of Hawks Crest, this 4-bedroom, 3.5-bath home offers 2,589 square feet of well-designed living space on a premium pond-view lot. Built in 2020, the home features a downstairs primary suite, open-concept living area, and a versatile upstairs loft. Additional highlights include a tile roof, modern finishes, a screened-in patio for outdoor living, and access to community amenities. This home combines location, layout, and value in a beautiful Winter Park gated communities.

1131 Wildmeadow Run, Winter Park

$829,500

4 Beds ⋅ 2 Baths ⋅ 32792 Zip Code

A unique opportunity with two separate structures on one parcel! The main home provides comfortable living, while the second building was previously licensed and used as a daycare and still has many of the necessary features in place. The additional space could also be used for multigenerational living, an in-law suite, guesthouse, home office, potential ADU, or future daycare operation. The property is not currently licensed as a daycare, but it offers plenty of possibilities for the next owner. All future uses are subject to applicable approvals. Showings by appointment only.

1521 Heron Wood Place, Winter Park

$485,000

4 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 01 SubDv. ⋅ 32792 Zip Code

NEW FLOORS, POOL, NO HOA, 4-YEAR-OLD ROOF & NEWER A/C!** Move-in ready 4-bedroom + office home offering 2,092 SF in the desirable Winter Woods/Lake Howell area of Winter Park. This well-maintained home features **brand-new flooring**, an open floor plan, granite countertops, modern appliances, abundant cabinetry, and a wood-burning fireplace. Enjoy Florida living with an oversized enclosed Florida room overlooking the **private in-ground pool and fully fenced backyard**—perfect for entertaining, pets, and relaxing. The spacious primary suite offers pool views, while the additional office/bonus room provides flexibility for working from home or extra living space. Additional features include a **roof approximately 4 years old, newer A/C, irrigation system, attached 2-car garage, additional parking, and NO HOA**. Conveniently located near shopping, dining, parks, golf, SR-417, SR-436, I-4, UCF, Downtown Orlando, and Winter Park amenities. **Vacant and ready for immediate occupancy—schedule your showing today!**

2217 Sussex Road, Winter Park

$399,900

4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code

This beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright natural light highlights a brand-new kitchen with modern appliances, a waterfall countertop, and soft wood finishes. Both bathrooms have been transformed with elegant marble look tile and spa style showers. You’ll fall in love with the large private backyard, perfect for summer barbecues, outdoor entertaining, play space, or even adding your own backyard oasis. All of this with no HOA and close to top rated Winter Park schools, popular dining, shopping, and parks. This move-in ready home offers lifestyle, comfort, and value you have to see in person, so schedule your showing today before it’s gone! ***Seller offering a $10,000 credit toward the buyer’s allowable closing costs and prepaid expenses. ***

1849 Viburnum Lane, Winter Park

$460,000

3 Beds ⋅ 2 Baths ⋅ Wrenwood Heights Unit 2 SubDv. ⋅ 32792 Zip Code

Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to parks, shopping, dining and main highways. Seminole County schools! Call today to schedule your private showing!

5331 Oak Court, Winter Park

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Winter Park FL Single Family Homes for Sale

There are 56 single family homes for sale in Winter Park, Florida as of 2026-09-18, at a median list price of $457,500 and a median of 42 days on market. Detached houses on their own lot, which is the bulk of what trades here.

Winter Park single family homes for sale at a glance

Active single family homes	56
Share of the Winter Park market	65.9% of 85 listings
Median list price	$457,500
Median price per square foot	$277
Median size	1,751 square feet
Median year built	1980
Median days on market	42
On market 60+ days	22 (39.29%)

Source: Stellar MLS via the Bridge RESO feed, pulled 2026-09-18. Updated weekly.

How Winter Park single family homes compare to the rest of the city

The median single family home in Winter Park asks $457,500 against $419,000 for the city as a whole, and $277 per square foot against $249. Single Family Homes make up 65.9% of everything on the market here.

29 of them, 51.79%, are asking less than they did originally, at a median reduction of 4.65%. That is the size of a first concession, not a final one.

Winter Park single family homes by price range

Under $250,000	0	0.0%
$250,000 to $400,000	10	17.9%
$400,000 to $600,000	29	51.8%
$600,000 and up	17	30.4%

Winter Park single family homes by bedroom count

3 bedrooms	21
4 bedrooms	29
5 bedrooms+	6

Zip codes

32792 (56)

Frequently asked questions

How many single family homes are for sale in Winter Park, FL?

There were 56 active single family homes listed in Winter Park as of 2026-09-18, 65.9% of the 85 residential listings in the city. That count comes from the Stellar MLS feed and is refreshed weekly.

What is the median price of a single family home in Winter Park, FL?

The median asking price was $457,500 as of 2026-09-18, or about $277 per square foot. The median single family home on the market is 1,751 square feet and was built in 1980.

How long do single family homes take to sell in Winter Park?

Median days on market was 42 as of 2026-09-18. 22 of the 56 active single family homes, 39.29%, have been listed 60 days or longer, and that is usually where the negotiating room is.

Are Winter Park single family homes cheaper than houses in Winter Park?

The median single family home asks $457,500 against $419,000 for all Winter Park listings, and $277 per square foot against $249 citywide. Price per square foot is the fairer comparison, because single family homes are usually the smaller property.

The Homes In Orlando Team at NextHome Neighborhood Realty covers Orange, Seminole, Lake and Volusia counties. Call or text 407-616-9019 to see any Winter Park listing on this page.