PROP_STATUS
PROP_ADDRESS
PROP_CITY, PROP_STATE
PROP_BEDS Beds / PROP_BATHS Baths
PROP_ACRES
PROP_PRICE
3 Beds /
2 Baths
/ 1,734 SqFt
On the first floor within The Cloisters, this three-bedroom, two-bath residence offers 1,734 square feet of renovated living space in one of Winter Pa...
4 Beds /
5 Baths
/ 3,971 SqFt
This is the kind of place you dream of, set on one of the most beautiful streets in Winter Park, Florida, the kind you can’t wait to come home t...
4 Beds /
3 Baths
/ 2,667 SqFt
Tucked away on a quiet circle in one of Winter Park''s most sought-after neighborhoods, this distinctive pool home offers a rare opportunity. S...
2 Beds /
3 Baths
/ 2,096 SqFt
Tucked along one of Winter Park’s charming brick streets and positioned directly across from Lake Sylvan, this recently renovated residence unfo...
3 Beds /
2.5 Baths
/ 2,426 SqFt
One or more photo(s) has been virtually staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neighborhood, 1651 Westchester Ave...
4 Beds /
3.5 Baths
/ 2,525 SqFt
Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood ...
4 Beds /
3.5 Baths
/ 2,936 SqFt
Pre-Construction. To be built. NEW CONSTRUCTION! Introducing an exquisite new construction home in Winter Park Grove, Winter Park''s newest com...
4 Beds /
3 Baths
/ 2,871 SqFt
This light and bright, single-story, almost 3,000 square foot pool home features a split plan with four full bedrooms and three full baths. Your guest...
6 Beds /
4 Baths
/ 2,282 SqFt
Opportunities like this don’t come around often, this is currently the only duplex available within walking distance of Park Avenue and just min...
4 Beds /
2 Baths
/ 2,750 SqFt
Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring an open floorplan, a generous family room, and a layout desi...
5 Beds /
3 Baths
/ 2,656 SqFt
Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park Hi...
4 Beds /
3 Baths
/ 2,597 SqFt
Step into the Winter Park lifestyle with a fully turnkey home designed to make daily living feel effortless. Set on an oversized corner lot, this full...
4 Beds /
4 Baths
/ 2,916 SqFt
Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this fully renovated 4-bedroom, 4-bath home delivers the r...
3 Beds /
3.5 Baths
/ 2,193 SqFt
One or more photo(s) has been virtually staged. Step into refined lakeside living at the exclusive Lake Killarney Townhomes, where contemporary elegan...
3 Beds /
2.5 Baths
/ 2,578 SqFt
Set on over half an acre in Winter Park’s coveted Orwin Manor, this 1935 French Provincial estate offers a rare blend of architectural character...
3 Beds /
2 Baths
/ 2,335 SqFt
Nestled in one of Winter Park’s most sought-after neighborhoods, this charming and meticulously maintained home offers three bedrooms, two baths...
4 Beds /
2.5 Baths
/ 2,431 SqFt
One or more photo(s) has been virtually staged. NEW PRICE! Experience refined living with NO HOA in this renovated custom designed home, positioned on...
Beds /
Baths
/ SqFt
Opportunity to build your dream home in gorgeous Winter Park. This large lot includes a 3 bedroom 2 bath updated home. With a lot comprising 140 x 78 ...
2 Beds /
1.5 Baths
/ 1,040 SqFt
Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tran...
3 Beds /
2 Baths
/ 2,114 SqFt
One or more photo(s) has been virtually staged. Introducing 250 Cortland Ave — a refined expression of Winter Park living, ideally positioned on...
4 Beds /
3.5 Baths
/ 2,662 SqFt
Pre-Construction. To be built. This is your final opportunity to build a custom home in one of Winter Park’s most sought-after pockets.
Set o...
4 Beds /
2 Baths
/ 3,950 SqFt
Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business c...
The data relating to real estate for sale on this site comes from Stellar MLS. All properties are subject to prior sale, changes, or withdrawal.
This site was last updated May-21-2026 4:39:43 pm.
This site was last updated May-21-2026 4:39:43 pm.
