Winter Park Homes for Sale

Latest Winter Park Homes and Condos for Sale

1049 N Kentucky Avenue, Winter Park image

1049 N Kentucky Avenue, Winter Park — 1049 $685,000

European-designed, Modern Townhome in the Heart of Winter Park! Walking distance to Park Ave, minutes from all that greater Winter Park has to offer. This stunning 3 be...

3 Beds
2.5 Baths
Fairbanks Park SubDv.
32789 Zip Code

2813 Northwood Boulevard, Winter Park image

2813 Northwood Boulevard, Winter Park $1,650,000

Welcome home to this two-story contemporary pool home full of upgrades featuring four bedrooms plus a large sun-filled office, three-and-a-half baths and a two-car garage...

4 Beds
3.5 Baths
Northwood Terrace SubDv.
32789 Zip Code

444 Covey Cove, Winter Park $1,050,000

This wonderful five-bedroom pool home is located on a quiet cul-de-sac in the lovely Quail Hollow. This waterfront split-level home has been updated throughout the years ...

5 Beds
3.5 Baths
Quail Hollow SubDv.
32789 Zip Code

1552 Golfside Drive, Winter Park $559,500

The BEST of both worlds...Water and Golf! Situated on a beautiful pond overlooking the 3rd fairway of the 18-hole Winter Park Pines Golf Course, this three-bedroom, two-...

3 Beds
2 Baths
Greenview At Winter Pines SubDv.
32792 Zip Code

1911 Oglesby Avenue, Winter Park $284,000

This is a 3 bedroom 2 bath home with a large kitchen and family room. The large fenced in back yard is perfect for your pets or most any outdoor activity. The possibil...

3 Beds
2 Baths
Olympia Heights SubDv.
32789 Zip Code

1217 Carvell Drive, Winter Park $365,000

FANTASTIC OPPORTUNITY to put your personal touches on this 3 bedroom 2 bath POOL HOME in WINTER PARK ESTATES zoned for LAKEMONT, MAITLAND MIDDLE & WINTER PARK HIGH! Quiet...

3 Beds
2 Baths
Winter Park Estates SubDv.
32792 Zip Code

1841 W Fairbanks Avenue, Winter Park image

1841 W Fairbanks Avenue, Winter Park $1,495,000

This listing is for 2 parcels, 1841 & 1831 W Fairbanks Ave. with the total of 3 buildings. 1841 is 2,400 SF on a 7,921 SF lot, and 1831 is 1,322 SF (1st building) plus 47...

32789 Zip Code

1647 Berkshire Avenue, Winter Park image

1647 Berkshire Avenue, Winter Park $750,000

Orwin Manor STUNNER. This spacious 3 bed, 2 bath * Welcome Home * Live and Entertain in Comfort * This home features a wonderfully open and flowing floor plan that was ta...

3 Beds
2 Baths
Orwin Manor Westminster Sec SubDv.
32789 Zip Code

1791 Grinnell Terrace, Winter Park image

1791 Grinnell Terrace, Winter Park $1,950,000 ▼

Stunning Winter Park home freshly remodeled in 2021-2022. This home missed no details when it comes to finishes and using the highest quality products. All around the hom...

4 Beds
4 Baths
Fremar SubDv.
32789 Zip Code

1038 Fairway Drive, Winter Park $625,000

Welcome to this WINTER PARK split floorplan beauty! The home, located near the Winter Park Pines Golf Club with tree lined streets, has so much character. Walking up to ...

4 Beds
2 Baths
Golfside Sec 03 SubDv.
32792 Zip Code

2025 Strathaven Road, Winter Park $457,000

Welcome home to this Winter Park Charmer! This quaint 3 Bedroom 2 Bath home sits in the beautiful neighborhood of Kenilworth Shores - which has deeded access to skiable L...

3 Beds
2 Baths
Kenilworth Shores Sec 07 SubDv.
32792 Zip Code

1400 Clay Street, Winter Park $339,999

Location! Location! Location! This charming 2 bedroom 1 bath home is located in the highly desired Orwin Manor neighborhood. The driveway that leads to the 1 car garage i...

2 Beds
1 Baths
Orwin Manor Westminster Sec SubDv.
32789 Zip Code

102 Bell Pl, Winter Park $400,000

Perfect place to build your dream home.

Eastgate Sub SubDv.
32792 Zip Code

1660 Woodland Avenue, Winter Park $3,250,000

Meticulously maintained by original owner, custom built on a lovely, quiet tree-lined brick street on an oversized 100x157 lot. Mature detailed landscaping greets you as ...

5 Beds
5.5 Baths
Comstock Park SubDv.
32789 Zip Code

2600 Euston Road, Winter Park $519,900

Location, location, location! Located in trendy Winter Park across from Lake Killarney. This is your opportunity to live the Winter Park lifestyle near Park Avenue and Do...

6 Beds
3 Baths
Glencoe Sub SubDv.
32789 Zip Code

281 Brewer Avenue, Winter Park $2,000,000

Gorgeous Contemporary Style Luxury Home minutes to Park Ave! This 5 Bedroom 4 and half bath home has an ideal floor plan with the Master, a guest room and an office on th...

5 Beds
4.5 Baths
Osceola Shores Sec 02 SubDv.
32789 Zip Code

1858 Barker Dr, Winter Park $625,900

A beautiful Winter Park TOTALLY RENOVATED 3BR/2BA home with 1,548 sq. ft. less than a mile away from the highly desirable Baldwin Park community. Features a grand front e...

3 Beds
2 Baths
South Lakemont Shores SubDv.
32789 Zip Code

1813 Gipson Green Lane, Winter Park image

1813 Gipson Green Lane, Winter Park $1,799,932

DREAM LOT IN A RARE LOCATION! This huge 99x231x100x218 (22,527 SqFt/.517 acre) is arguably a “lifetime opportunity” for your next Estate Home on a picturesque, sought-aft...

Boiley Green Sub SubDv.
32789 Zip Code

130 Killarney Bay Court Unit 5-3, Winter Park image

130 Killarney Bay Court Unit 5-3, Winter Park — 5-3 $399,000

Be prepared to be impressed with this delightful townhouse style condo located in Killarney Bay in Winter Park. This 2-bedroom 2.5 bath condo has much to offer. As you ...

2 Beds
2.5 Baths
Killarney Bay Condo SubDv.
32789 Zip Code

2843 Eastern Parkway, Winter Park $689,000

This beautiful fully renovated WINTER PARK POOL HOME will blow you away with its salt water lagoon style pool, open floor plan, and attention to detail in all aspects of ...

3 Beds
1.5 Baths
Orangewood Park SubDv.
32789 Zip Code

1130 Palmer Avenue, Winter Park $1,600,000

Looking for a large lot in Winter Park with deeded lake access to the chain of lakes? Consider this your opportunity to buy an almost 15,000 sf corner lot on one of the ...

3 Beds
3 Baths
Palmer Ave Lakeside Prop SubDv.
32789 Zip Code

1781 Goodrich Avenue, Winter Park $510,000

Are you ready to live in the epicenter and Heart of Central Florida's exclusive Winter Park 32789? Come inside and discover beautiful hardwood floors throughout that comp...

2 Beds
1 Baths
Sylvan Heights SubDv.
32789 Zip Code

912 Fairway Dr, Winter Park $485,900 ▼

A lovely 4 bedroom 2 bath home with lots of space for your family to live and play. The split plan provides the opportunity to get away and the indoor laundry room just o...

4 Beds
2 Baths
Golfside Sec 03 No Active Association SubDv.
32792 Zip Code

1414 Bessmor Road, Winter Park $430,000

Beautiful rehabbed Modern Bungalow in highly sought-after Winter Park. House has been completely updated with new flooring throughout, a brand new kitchen with all new Sa...

3 Beds
1 Baths
Winter Park Village SubDv.
32789 Zip Code

1514 Minnesota Ave, Winter Park $320,000 ▼

Location, Location, Location! Just located less than five minutes from Winter Park Village and 10 minutes from downtown Orlando. Quaint and cozy describes this great home...