Winter Park Homes for Sale

Latest Winter Park Homes and Condos for Sale

423 Warrenton Road Unit 423, Winter Park image

423 Warrenton Road Unit 423, Winter Park — 9 $293,500

Beautiful Condo in Winter Park. Cathedral ceilings, wood floors throughout with ceramic tile in wet areas, kitchen and dining room. Updated appliances, cabinets and quar...

2 Beds
2 Baths
Winter Park Pines Condo SubDv.
32792 Zip Code

2911 Antique Oaks Circle Unit GE, Winter Park image

2911 Antique Oaks Circle Unit GE, Winter Park — 2911 $199,000

WHAO LOCATION! GROUND FLOOR CONDO 1018 SQUARE FEET!. Two bedrooms and two full bathrooms with an open floor plan and walk-in closet in Master bedroom! Includes Fridge, Ra...

2 Beds
2 Baths
Parkview Village SubDv.
32792 Zip Code

600 Maiden Lane, Winter Park $1,575,000

Perched on a hill on a corner lot, nestled between Sylvan and Bonita along the brick streets of Winter Park, this home has so much to offer. With a privacy wall along Mai...

4 Beds
4.5 Baths
Comstock Park SubDv.
32789 Zip Code

234 Scottsdale Square Unit 234, Winter Park image

234 Scottsdale Square Unit 234, Winter Park — 234 $145,000

INCREDIBLE OPPORTUNITY to own an updated two-story condo with lush garden views from BOTH BALCONIES! The unit underwent an enormous upgrade overhaul just a few years ago ...

2 Beds
1.5 Baths
Winter Park Woods Condo SubDv.
32792 Zip Code

1769 Indiana Avenue Unit D, Winter Park image

1769 Indiana Avenue Unit D, Winter Park — Las Casas De Indiana $429,000

Mediterranean style Townhouse, granite counter tops, SS appliances, hardwood floors on first floor and carpet on second floor, private courtyard, detached one car garage ...

3 Beds
2.5 Baths
Las Casas De Indiana SubDv.
32789 Zip Code

4033 Tenita Drive, Winter Park $559,000

Cozy Winter Park Pool Home in Orange County - Move-in Ready! Experience the outdoor oasis by relaxing in your screened Lanai or take a dip in the private pool. Great for ...

4 Beds
2 Baths
Lake Waunatta Woods SubDv.
32792 Zip Code

1303 Alberta Drive, Winter Park $2,950,000

Welcome to this exquisite French Modern home that seamlessly blends classic architecture with modern amenities. With 4 bedrooms, 4.5 bathrooms, 4,055 s/f, and a detached...

4 Beds
4.5 Baths
Alberta Place SubDv.
32789 Zip Code

3173 Crown Jewel Court, Winter Park image

3173 Crown Jewel Court, Winter Park $375,000

Wanting to live in Winter Park in a newer and beautiful property? Here it is. This beautiful property is so centrally located that has it all near by within less than 10 ...

3 Beds
2.5 Baths
Coronado Twnhms SubDv.
32792 Zip Code

2827 Parkland Circle, Winter Park $1,995,000

Welcome home to this professionally decorated two-story custom French provincial pool home. No space or detail has been overlooked, and with an endless list of upgrades, ...

4 Beds
3.5 Baths
Lake Forest Park SubDv.
32789 Zip Code

1714 Westchester Avenue, Winter Park image

1714 Westchester Avenue, Winter Park $799,000

Welcome to Orwin Manor, a timeless Orlando-Winter Park neighborhood established in 1924, offering lifestyle and prime location. Come see this designer dream! Solidly buil...

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

1918 Summerfield Road, Winter Park image

1918 Summerfield Road, Winter Park $1,300,000

BETTER THAN NEW AND READY FOR YOU! BUILT IN 2021!! Designed and built by Winter Park architect and building contractor, Stevens, Inc., this CUSTOM CRAFTSMAN style home br...

5 Beds
4.5 Baths
Kenilworth Shores Section Seven SubDv.
32792 Zip Code

1554 Harris Circle, Winter Park $1,220,000

Pre-inspected. Offered for the first time in over 30 years! Winter Park’s only original, charming and completely remodeled historical farmhouse. Known as the “Harris-Edis...

3 Beds
2.5 Baths
Sylvan Lake Shores SubDv.
32789 Zip Code

1740 Via Palermo, Winter Park $4,200,000

Nestled near the heart of Winter Park, this modern masterpiece exudes elegance and superb attention to detail throughout. This home was a Parade of Homes collaboration be...

5 Beds
5.5 Baths
Sicilian Shores Rep 02 SubDv.
32789 Zip Code

656 Randy Lane, Winter Park $795,000

Located on a quiet, tree lined street in Timberlane, a neighborhood in Winter Park that is known for its beautiful homes and excellent proximity to great schools, amazing...

3 Beds
2 Baths
Timberlane SubDv.
32789 Zip Code

3651 N Goldenrod Road Unit F207, Winter Park image

3651 N Goldenrod Road Unit F207, Winter Park — 207 $210,000

Live in desirable Winter Park in this cute renovated 2/2 condo. This unit is ideal whether you are an investor or an owner-occupant. This is an opportunity to live in a c...

2 Beds
2 Baths
Lancelot At Winter Park SubDv.
32792 Zip Code

2680 Oglesby Avenue, Winter Park $949,900

Dreams do come true! 2019 Newer Build Winter Park and College Park Adjacent Paradiso! No HOA! Modern Farmhouse style with almost 2600 sqft of spacious floorplan featurin...

4 Beds
2.5 Baths
Dubsdread Heights SubDv.
32789 Zip Code

316 Scottsdale Square Unit 316, Winter Park image

316 Scottsdale Square Unit 316, Winter Park — 316 $145,000

Welcome to your new cozy and charming 2-story condo at Winter Park Woods! Tucked away just off SR-436, this delightful 2-bedroom, 1.5-bathroom home is perfectly situated ...

2 Beds
1.5 Baths
Winter Park Woods Condo SubDv.
32792 Zip Code

526 Genius Drive, Winter Park $4,150,000

Magnificent lakeview estate in Windsong – 526 Genius Drive, Winter Park – Offered at $4,150,000! For the first time, this stately residence is on the market and available...

4 Beds
4.5 Baths
Windsong North Shore 43/74 SubDv.
32789 Zip Code

110 Orlando Unit Suite 4, Winter Park image

110 Orlando Unit Suite 4, Winter Park $120,000

GREAT BUSINESS OPPORTUNITY! - Excellent location, in the heart of Winter Park. Beautiful cafeteria, with highly qualified personnel to offer the public an experience of i...

32789 Zip Code

195 Cortland Avenue, Winter Park $1,475,000

This fabulous home is on one of Winter Park’s most charming brick streets and a short stroll leads you to Lake Mizell. It features an abundance of natural light and blend...

3 Beds
3.5 Baths
Cortland Park SubDv.
32789 Zip Code

698 N New York Avenue, Winter Park image

698 N New York Avenue, Winter Park $1,800,000

Just Listed!! Impeccable location a half block off Park Avenue with incredible views of the golf course. Listed $130,000.00 below appraised value as of Oct 2022. This won...

32789 Zip Code

250 Cortland Avenue, Winter Park $1,000,000

250 Cortland is nestled among million-dollar homes on one of the nicest brick, tree lined streets in Winter Park. This 3bedroom, 2 bath split bedroom home plan has low ma...

3 Beds
2 Baths
Cortland Park SubDv.
32789 Zip Code

206 Balfour Drive Unit 6, Winter Park image

206 Balfour Drive Unit 6, Winter Park — 206 $370,000

Beautiful ONE STORY Winter Park Condo with attached 2 car GARAGE!! Need to downsize? You won't have to give up everything! 2 Bedroom, 2 Baths PLUS a Den/Office. Eat i...

2 Beds
2 Baths
Winter Park Pointe 02 Ph 02 SubDv.
32792 Zip Code

2461 Salisbury Boulevard, Winter Park image

2461 Salisbury Boulevard, Winter Park $400,000

LOCATION AND SPACE! Everyone would love that without a doubt! And this fabulous Winter Park/College Park bungalow can offer you both. Plus! This home is in great conditio...

3 Beds
2 Baths
Glencoe Sub SubDv.
32789 Zip Code

2337 Summerfield Road, Winter Park image

2337 Summerfield Road, Winter Park $675,000

Beautiful family home for sale! 5 Bedrooms, 2 Bathrooms, 2 car garage, formal living and dining rooms, a family room attached to the eat in kitchen, and a screened back p...