MLS Listings for Sale in Winter Park, FL

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ABOUT THIS HOME
MLS Listings for Sale in Winter Park, FL
Wonderful opportunity - homes rarely come available on this street! Located in the heart of Winter Park, this elegantly designed 3-bedroom, 2.5-bathroom residence offers 2,557 square feet of living space and a 2-car garage on a picturesque tree-lined brick street just minutes from Park Avenue. The first level features the living room, bonus/flex space, dining room, kitchen and laundry room with storage. The centrally located designer kitchen features a herringbone tile backsplash, custom wood-wrapped hood, decorative island, and an adjacent dining room with a built-in buffet. A double-sided wood-burning fireplace serves as a striking centerpiece, separating a flexible space with a wet bar f

$1,190,000

3 beds2.5 baths2,557 sq ft

1150 Kenwood Ave, Winter Park, FL 32789

Designer kitchen • Manicured backyard • Wet bar

ABOUT THIS HOME
MLS Listings for Sale in Winter Park, FL
This is a 3 bedroom and 2 bathroom condo. This condo has had everything replaced. Don't miss out on this opportunity. Call listing agent today for more information and to schedule a showing.

$179,900

3 beds2 baths— sq ft

7340 Daniel Webster Dr, Winter Park, FL 32792

$626 HOA • Parking • Community pool

(305) 914-7653

ABOUT THIS HOME
MLS Listings for Sale in Winter Park, FL
This beautiful Mediterranean style home offers a rare opportunity for prime waterfront living on Lake Mizell, part of the highly sought out after Winter Park Chain of Lakes. Situated on a 1.32 acre lot, the property is just a short walk or drive to Park Avenue’s restaurants, boutiques, and local attractions. The main home features three bedrooms and five bathrooms, each bedroom offering its own en suite bathroom. A separate guest house (ADU) provides an additional 932 square feet with two bedrooms, one bathroom, newly refinished original hardwood floors, fresh paint and a wood burning fireplace perfect for guests or extended family. Inside the main residence, you’ll find solid w

$3,795,000

5 beds6 baths4,143 sq ft

516 Henkel Cir, Winter Park, FL 32789

Solid wood flooring • 1.32 acre lot • Travertine flooring

3D WALKTHROUGH

ABOUT THIS HOME
MLS Listings for Sale in Winter Park, FL
One or more photo(s) has been virtually staged. Don’t miss out on this beautifully maintained, 2 bed, 2 bath, single story townhome in the sought after Winter Park Pines with a LOW HOA! As you make your way towards the entrance you have 2 private, fenced-in courtyard areas for sitting out for a morning coffee, home gardening, or just getting out to enjoy the weather. As you enter the home you see nicely updated kitchen with granite countertops, stainless steel appliances, and white cabinets. The great room is exactly that, with large vaulted ceilings and plenty of natural light. The spacious Owner’s Suite is complete with a gorgeous, recently renovated bathroom and walk-in close

$320,000

2 beds2 baths1,221 sq ft

615 Warrenton Rd, Winter Park, FL 32792

White cabinets • Updated kitchen • Granite countertops

3D & VIDEO TOUR

ABOUT THIS HOME
MLS Listings for Sale in Winter Park, FL
Waterfront dream home in the exclusive, gated community of Lakeside Estates on beautiful Garden Lake. This exquisite 7-bedroom plus office, 4-bath “Del Rio” model offers over 5,000 sq. ft. and has been COMPLETELY RENOVATED in 2025 with high-end finishes, designer lighting, and modern upgrades throughout. Situated in a gated, quiet cul-de-sac community, this property features the largest yard (. 5 ACRE) in the neighborhood and direct lakefront access, perfect for adding a dock, pool, or basketball court. Accordion doors lead to an expansive brick paver patio with a covered lanai, yard with fruit trees and breathtaking sunsets over Garden Lake High ceilings, all interiors painted

$1,560,000

7 beds4 baths5,111 sq ft

1460 Via Sangro Pl, Winter Park, FL 32792

Gourmet kitchen • Largest yard • Custom wet bars

Property at 2009 Cornell Ave, Winter Park, FL 32789, 2 beds, 1 bath

$269,000

2 beds1 bath762 sq ft

2009 Cornell Ave, Winter Park, FL 32789

Property at 2381 Roxbury Rd, Winter Park, FL 32789, 3 beds, 2 baths

$499,900

3 beds2 baths1,785 sq ft

2381 Roxbury Rd, Winter Park, FL 32789

Property at 3018 Northwood Blvd, Winter Park, FL 32789, 3 beds, 2 baths

$749,700

3 beds2 baths1,761 sq ft

3018 Northwood Blvd, Winter Park, FL 32789

Property at 7309 Daniel Webster Dr Unit 0-2B, Winter Park, FL 32792, 1 bed, 1 bath

$109,999

1 bed1 bath— sq ft

7309 Daniel Webster Dr Unit 0-2B, Winter Park, FL 32792

(305) 914-7653

Property at 100 S Interlachen Ave #415, Winter Park, FL 32789, 2 beds, 2 baths

$1,195,000

2 beds2 baths1,267 sq ft

100 S Interlachen Ave #415, Winter Park, FL 32789

Property at 259 Blossom Ln, Winter Park, FL 32789, 3 beds, 2 baths

$499,000

3 beds2 baths1,354 sq ft

259 Blossom Ln, Winter Park, FL 32789

Property at 3319 Ellwood Ct, Winter Park, FL 32792, 5 beds, 3 baths

$480,000

5 beds3 baths1,546 sq ft

3319 Ellwood Ct, Winter Park, FL 32792

Property at 1822 Greenwich Ave, Winter Park, FL 32789, 3 beds, 2 baths

$1,199,900

3 beds2 baths1,627 sq ft

1822 Greenwich Ave, Winter Park, FL 32789

Property at 2580 Euston Rd, Winter Park, FL 32789, 3 beds, 2 baths

$425,000

3 beds2 baths1,158 sq ft

2580 Euston Rd, Winter Park, FL 32789

Property at 1250 S Denning #122 St #00122, Winter Park, FL 32789, 1 bed, 1 bath

$179,900

1 bed1 bath653 sq ft

1250 S Denning #122 St #00122, Winter Park, FL 32789

Property at 7502 Waunaqua Dr, Winter Park, FL 32792, 5 beds, 3 baths

$567,000

5 beds3 baths2,615 sq ft

7502 Waunaqua Dr, Winter Park, FL 32792

Property at 132 Burks Cir, Winter Park, FL 32789, 4 beds, 4.5 baths

$1,675,000

4 beds4.5 baths3,022 sq ft

132 Burks Cir, Winter Park, FL 32789

Property at 5201 Ardmore Dr, Winter Park, FL 32792, 3 beds, 2 baths

$428,900

3 beds2 baths1,640 sq ft

5201 Ardmore Dr, Winter Park, FL 32792

Property at 2920 Abbey Ct, Winter Park, FL 32792, 5 beds, 3 baths

$650,000

5 beds3 baths2,312 sq ft

2920 Abbey Ct, Winter Park, FL 32792

Property at 1267 Michigan Ave, Winter Park, FL 32789, 3 beds, 2.5 baths

$655,000

3 beds2.5 baths1,798 sq ft

1267 Michigan Ave, Winter Park, FL 32789

Property at 2905 Antique Oaks Cir #6, Winter Park, FL 32792, 1 bed, 1 bath

$165,000

1 bed1 bath749 sq ft

2905 Antique Oaks Cir #6, Winter Park, FL 32792

Property at 2955 Lolissa Ln, Winter Park, FL 32789, 4 beds, 3 baths

$749,000

4 beds3 baths3,538 sq ft

2955 Lolissa Ln, Winter Park, FL 32789

Property at 121 Stefanik Rd, Winter Park, FL 32792, 3 beds, 2 baths

$337,500

3 beds2 baths1,392 sq ft

121 Stefanik Rd, Winter Park, FL 32792

Property at 1016 Howell Branch Rd, Winter Park, FL 32789, 4 beds, 3 baths

$1,836,000

4 beds3 baths3,142 sq ft

1016 Howell Branch Rd, Winter Park, FL 32789

Property at 1507 Grove St #557, Maitland, FL 32751, 3 beds, 2 baths

$239,900

3 beds2 baths1,256 sq ft

1507 Grove St #557, Maitland, FL 32751

Property at 633 Balmoral Rd, Winter Park, FL 32789, 4 beds, 2.5 baths

$1,950,000

4 beds2.5 baths2,674 sq ft

633 Balmoral Rd, Winter Park, FL 32789

Property at 1509 Sugarwood Cir, Winter Park, FL 32792, 3 beds, 2 baths

$189,900

3 beds2 baths1,706 sq ft

1509 Sugarwood Cir, Winter Park, FL 32792

Property at 1601 Grove St #552, Maitland, FL 32751, 2 beds, 2 baths

$260,000

2 beds2 baths1,087 sq ft

1601 Grove St #552, Maitland, FL 32751

Property at Undisclosed address, Winter Park, FL 32792, 4 beds, 3 baths

$599,000

4 beds3 baths2,878 sq ft

Undisclosed address, Winter Park, FL 32792

Property at 1655 Sunnyside Dr, Maitland, FL 32751, 3 beds, 2 baths

$725,000

3 beds2 baths1,418 sq ft

1655 Sunnyside Dr, Maitland, FL 32751

Property at 614 Grenadine Ct N #614, Winter Park, FL 32792, 1 bed, 1 bath

$158,000

1 bed1 bath759 sq ft

614 Grenadine Ct N #614, Winter Park, FL 32792

Property at 1861 Taylor Ave, Winter Park, FL 32789, 5 beds, 6 baths

$1,975,000

5 beds6 baths3,116 sq ft

1861 Taylor Ave, Winter Park, FL 32789

Property at 1007 Early Ave, Winter Park, FL 32789, 3 beds, 2 baths

$425,000

3 beds2 baths1,721 sq ft

1007 Early Ave, Winter Park, FL 32789

Property at 740 Baffie Ave, Winter Park, FL 32789, 3 beds, 2 baths

$445,000

3 beds2 baths1,456 sq ft

740 Baffie Ave, Winter Park, FL 32789

Property at 428 Selkirk Dr, Winter Park, FL 32792, 4 beds, 3 baths

$650,000

4 beds3 baths1,782 sq ft

428 Selkirk Dr, Winter Park, FL 32792

Property at 2152 Conifer Ave, Winter Park, FL 32792, 3 beds, 2 baths

$460,000

3 beds2 baths1,694 sq ft

2152 Conifer Ave, Winter Park, FL 32792

Property at 3028 George Mason Ave #7, Winter Park, FL 32792, 2 beds, 2 baths

$40,000

2 beds2 baths1,088 sq ft

3028 George Mason Ave #7, Winter Park, FL 32792

Property at 107 Scottsdale Sq #107, Winter Park, FL 32792, 1 bed, 1 bath

$100,000

1 bed1 bath756 sq ft

107 Scottsdale Sq #107, Winter Park, FL 32792

Property at 265 E Canton Ave Unit GE, Winter Park, FL 32789, 2 beds, 2 baths

$631,400

2 beds2 baths1,057 sq ft

265 E Canton Ave Unit GE, Winter Park, FL 32789

Property at 1581 Forest Ave, Winter Park, FL 32789, 4 beds, 5 baths

$3,775,000

4 beds5 baths4,683 sq ft

1581 Forest Ave, Winter Park, FL 32789

Property at 1306 Lindenwood Ln, Winter Park, FL 32792, 4 beds, 4.5 baths

$1,499,000

4 beds4.5 baths3,726 sq ft

1306 Lindenwood Ln, Winter Park, FL 32792

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Based on information submitted to the MLS GRID as of Mon Nov 17 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

MLS Listings for Sale in Winter Park

There are currently 294 mls listings for sale in Winter Park at a median listing price of $864K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winter Park stay on the market for 94 days and receive 5 offers. Popular neighborhoods include Audubon Park, College Park, Winter Park Pines, Baldwin Park, and Downtown Maitland. This map is refreshed with the newest listings in Winter Park every 15 minutes.

In the past month, 50 homes have been sold in Winter Park. In addition to houses in Winter Park, there were also 66 condos, 15 townhouses, and 2 multi-family units for sale in Winter Park last month. Winter Park is a minimally walkable city in Orange County with a Walk Score of 44. Winter Park is home to approximately 27,958 people and 25,253 jobs. Find your dream home in Winter Park using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winter Park are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winter Park. Our Winter Park real estate stats and trends will give you more information about home buying and selling trends in Winter Park. If you're looking to sell your home in the Winter Park area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winter Park with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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