Single family homes for sale in Winter Park, FL

206 Listings

mediterranean / spanish-style home with a balcony, a front lawn, and a garage

foyer featuring light hardwood / wood-style floors

dining area with hardwood / wood-style flooring

$2,999,900

4 beds • 4 baths • 4,875 sqft

2550 Venetian Way, Winter Park FL 32789

#O6258445, Brian Rotenberger, Listing Office: COMPASS FLORIDA LLC

mediterranean / spanish home featuring a garage

Video tour

$10,000 Closing Credit¹

$1,299,000

5 beds • 4.5 baths • 4,435 sqft

7440 Aloma Ave, Winter Park FL 32792

#O6258176, DeShawn Robinson, Listing Office: MARZUCCO REAL ESTATE

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front of property featuring a garage and a front yard

view of pool with an outdoor fire pit, a patio area, and a sunroom

Video tour

$9,678 Closing Credit¹

$815,000

4 beds • 3.5 baths • 2,823 sqft

1316 Fountain Hills Ct, Winter Park FL 32792

#O6257903, Alex Lamar, Listing Office: EMPIRE NETWORK REALTY

unfurnished living room with light tile patterned floors and ceiling fan

$10,000 Closing Credit¹

$1,649,000

4 beds • 4 baths • 3,116 sqft

1429 Chapman Cir, Winter Park FL 32789

#O6257912, Greg Martinez, Listing Office: CORCORAN PREMIER REALTY

single story home featuring a front lawn and a garage

ranch-style house with a garage and a front lawn

$6,886 Closing Credit¹

$579,900

4 beds • 2 baths • 2,205 sqft

2518 Sweetwater Trl, Winter Park FL 32789

#O6255305, Joseph Doher, Listing Office: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

view of front of property with a front yard

interior space featuring ceiling fan and light wood-type flooring

unfurnished living room featuring ceiling fan, a healthy amount of sunlight, and light hardwood / wood-style floors

Video tour

$5,639 Closing Credit¹

$474,900

3 beds • 2 baths • 1,773 sqft

2341 Devon Ct, Winter Park FL 32789

#O6257142, Bruce Winslow, Listing Office: UNITED REAL ESTATE PREFERRED

front facade with a garage and a front lawn

view of front facade with a garage and a front lawn

$5,938 Closing Credit¹

$500,000

4 beds • 2.5 baths • 2,290 sqft

5240 N Lake Burkett Ln, Winter Park FL 32792

#O6254524, Ashley Harper, Listing Office: COLDWELL BANKER REALTY

Room to negotiate?

Median Sold Price

$469.6K

Avg. Sale Time

62 Days

Based on our February 2025 Market Report.

back of house featuring a pool side deck and outdoor lounge area

$4,100,000

5 beds • 5.5 baths • 4,520 sqft

1751 Glencoe Rd, Winter Park FL 32789

#O6255877, Julie Christensen, Listing Office: COMPASS FLORIDA LLC

ranch-style home with a front yard and a carport

ranch-style home featuring a carport and a front lawn

unfurnished living room featuring a barn door, plenty of natural light, and light wood-type flooring

Video tour

$5,130 Closing Credit¹

$432,000

3 beds • 2 baths • 1,346 sqft

627 Carvell Dr, Winter Park FL 32792

#O6255765, Ray Al Malt, Listing Office: EXP REALTY LLC

view of front of house featuring a front yard

front facade featuring a garage and a front yard

$5,213 Closing Credit¹

$439,000

3 beds • 2.5 baths • 1,725 sqft

1820 Blaine Ter, Winter Park FL 32792

#O6254945, Melissa Gonzalez, Listing Office: LPT REALTY

view of front of property with a front yard, a porch, and a garage

dining space featuring light hardwood / wood-style flooring

dining space featuring light wood-type flooring

$10,000 Closing Credit¹

$869,000

5 beds • 3 baths • 1,813 sqft

1795 Walker Ave, Winter Park FL 32789

#O6254742, Tiffany Pantozzi, Listing Office: ALIGN REAL ESTATE LLC

view of front of property with a front yard and a garage

view of front of house with a front lawn and a garage

Video tour

$10,000 Closing Credit¹

$875,555

3 beds • 2 baths • 1,760 sqft

2128 Sycamore Dr, Winter Park FL 32789

#A11686489, Luis Perez Garcia, Listing Office: EXP Realty LLC

view of swimming pool with ceiling fan, an outdoor hangout area, glass enclosure, and a patio area

living room with lofted ceiling, ceiling fan, and light hardwood / wood-style floors

Video tour

$8,301 Closing Credit¹

$699,000

4 beds • 3.5 baths • 2,717 sqft

3136 Heartleaf Pl, Winter Park FL 32792

#O6253346, Erica Garcia, Listing Office: ALL REAL ESTATE & INVESTMENTS

rear view of property with a yard and a wooden deck

$10,000 Closing Credit¹

$995,000

3 beds • 3.5 baths • 1,844 sqft

870 Carver St, Winter Park FL 32789

#O6250529, Drew Henner, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

view of dock with a yard and a water view

single story home with a front yard and a garage

Video tour

$10,000 Closing Credit¹

$1,350,000

3 beds • 2 baths • 2,342 sqft

632 Country Club Dr, Winter Park FL 32789

#O6250417, Kristin Duncan, Listing Office: KELLER WILLIAMS ADVANTAGE REALTY

single story home featuring cooling unit, driveway, an attached garage, and a front yard

view of pool with a fenced in pool and a fenced backyard

living room featuring light tile patterned floors, high vaulted ceiling, and a ceiling fan

$4,749 Closing Credit¹

$399,900

3 beds • 2 baths • 1,301 sqft

5418 S Bracken Ct, Winter Park FL 32792

#O6251052, Chelsea Feinberg, Listing Office: EXP REALTY LLC

view of front facade featuring a front lawn and a garage

Video tour

$10,000 Closing Credit¹

$875,555

3 beds • 2 baths • 1,760 sqft

2128 Sycamore Dr, Winter Park FL 32789

#L4948316, Luis Perez Garcia, Listing Office: EXP REALTY LLC

ranch-style house with a carport and a front lawn

birds eye view of property featuring a water view

Video tour

$6,234 Closing Credit¹

$525,000

3 beds • 2 baths • 1,440 sqft

2821 Chantilly Ave, Winter Park FL 32789

#O6249965, Catherine D'Amico, Listing Office: FANNIE HILLMAN & ASSOCIATES

back of house featuring a patio, a balcony, a lawn, and a fenced in pool

view of front of property featuring a front yard and a garage

Video tour

$10,000 Closing Credit¹

$2,374,000

4 beds • 3.5 baths • 3,399 sqft

2522 Lafayette Ave, Winter Park FL 32789

#O6250342, Jude DeVito, Listing Office: COLDWELL BANKER RESIDENTIAL RE

mediterranean / spanish-style house featuring a front yard and a garage

Video tour

$5,400,000

5 beds • 5.5 baths • 5,072 sqft

2228 Azalea Pl, Winter Park FL 32789

#O6250411, Quentin Green, II, Listing Office: COMPASS FLORIDA LLC

view of front of home featuring a front yard

Video tour

$4,014 Closing Credit¹

$338,000

3 beds • 2 baths • 1,078 sqft

5080 Seminole Ave, Winter Park FL 32792

#O6249839, Vanessa Scotland, PA, Listing Office: SERHANT

view of front of home with a front yard and a carport

living room with a textured ceiling and hardwood / wood-style floors

Video tour

$5,166 Closing Credit¹

$435,000

3 beds • 2 baths • 1,540 sqft

920 Gloriosa Ave, Winter Park FL 32789

#G5088048, Marie Cameron, Listing Office: CHARLES RUTENBERG REALTY ORLANDO

view of front of house featuring a front lawn

view of front of property featuring a balcony and a garage

$3,892,000

4 beds • 5.5 baths • 4,635 sqft

1391 Richmond Rd, Winter Park FL 32789

#O6246352, Julie Bettosini, PA, Listing Office: STOCKWORTH REALTY GROUP

ranch-style house featuring a front lawn

view of front of home with a front lawn and a carport

3D tour

$4,738 Closing Credit¹

$399,000

4 beds • 2 baths • 1,554 sqft

2140 Ridge Dr, Winter Park FL 32792

#O6244737, Chad Vaughan, Listing Office: REAL BROKER, LLC

view of front facade featuring a front lawn

Video tour

$10,000 Closing Credit¹

$1,445,000

4 beds • 2.5 baths • 2,739 sqft

1371 Lyndale Blvd, Winter Park FL 32789

#O6245047, Jeffery Reupert, Listing Office: COLDWELL BANKER RESIDENTIAL RE

single story home featuring a front yard and a garage

single story home featuring a garage, cooling unit, and a front lawn

Video tour

$6,353 Closing Credit¹

$535,000

4 beds • 3 baths • 2,327 sqft

4013 Quenita Dr, Winter Park FL 32792

#O6243744, Sean Notice, Listing Office: CHARLES RUTENBERG REALTY ORLANDO

Video tour

$4,987 Closing Credit¹

$419,999

3 beds • 2 baths • 1,476 sqft

5210 Poinsetta Ave, Winter Park FL 32792

#O6240219, Kevin Wilhelm, Listing Office: MLSB THE BUREAU POWERED BY CAROM REALTY

view of front of property featuring a yard and a garage

pool at dusk featuring a patio and french doors

Video tour

$10,000 Closing Credit¹

$1,999,993

6 beds • 4 baths • 3,853 sqft

1451 Lyndale Blvd, Winter Park FL 32789

#O6237975, Chris Soucy, Listing Office: REALTY ONE GROUP MVP

view of front of house with a front lawn and an attached garage

exterior space featuring decorative driveway, fence, and an attached garage

view of front of property featuring brick siding, a chimney, a front yard, and fence

$7,481 Closing Credit¹

$630,000

2 beds • 2 baths • 1,162 sqft

1848 Mizell Ave, Winter Park FL 32789

#O6236639, Jorge Zea, Listing Office: BLUE LIGHTHOUSE REALTY INC

view of front of house featuring a garage and a yard

view of patio / terrace featuring an outdoor stone fireplace

stairs featuring hardwood / wood-style floors

Video tour

$3,295,000

5 beds • 5.5 baths • 4,080 sqft

1730 Winchester Dr, Winter Park FL 32789

#O6235073, Nick McKee, Listing Office: KELLER WILLIAMS WINTER PARK

ranch-style house featuring a front lawn and a carport

Video tour

$10,000 Closing Credit¹

$995,000

2 beds • 1.5 baths • 1,374 sqft

2260 Hawick Ln, Winter Park FL 32792

#O6232951, Michael Rasmussen, Listing Office: DAVEN REAL ESTATE INC

ranch-style house featuring a porch, a garage, an outdoor structure, and a front yard

Video tour

$9,499 Closing Credit¹

$799,900

2 beds • 1 bath • 960 sqft

731 Midget Dr, Winter Park FL 32789

#O6232383, Laura Lane Heidrich, Listing Office: COLDWELL BANKER RESIDENTIAL RE

ranch-style home featuring a garage and a front lawn

Video tour

$10,000 Closing Credit¹

$1,795,000

4 beds • 3 baths • 3,472 sqft

279 Rippling Ln, Winter Park FL 32789

#O6230955, John McDade, Listing Office: FANNIE HILLMAN & ASSOCIATES

corridor featuring light hardwood / wood-style floors

sitting room featuring hardwood / wood-style floors and a healthy amount of sunlight

Video tour

$10,000 Closing Credit¹

$1,099,900

5 beds • 3 baths • 2,641 sqft

1840 Biscayne Dr, Winter Park FL 32789

#O6226190, Laura Hope, Listing Office: COMPASS FLORIDA LLC

foyer entrance featuring ornamental molding, hardwood / wood-style floors, and a notable chandelier

$10,000 Closing Credit¹

$1,625,000

4 beds • 4 baths • 3,777 sqft

1650 Lakehurst Ave, Winter Park FL 32789

#O6225250, Kelly Price, Listing Office: KELLY PRICE & COMPANY LLC

back of house at dusk with a yard, a patio, stone siding, and a balcony

back of property at dusk with a patio area, a lawn, a balcony, and stucco siding

Video tour

$4,200,000

7 beds • 5 baths • 5,500 sqft

571 Lake Front Blvd, Winter Park FL 32789

#O6220284, Harif Hazera, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

exterior space featuring a front lawn and solar panels

$9,499 Closing Credit¹

$799,900

4 beds • 3 baths • 2,503 sqft

2804 Dike Rd, Winter Park FL 32792

#O6220247, Barrett Spray, Listing Office: KELLER WILLIAMS ADVANTAGE REALTY

view of front of house featuring brick siding, a shingled roof, and a front lawn

living area featuring wood finished floors, french doors, visible vents, and a wealth of natural light

view of front facade featuring brick siding and a front lawn

Video tour

$10,000 Closing Credit¹

$2,160,000

6 beds • 3.5 baths • 3,554 sqft

2234 Via Luna, Winter Park FL 32789

#O6217019, Iram Hashmi, Listing Office: LOKATION

single story home featuring a front lawn

dining area featuring plenty of natural light, light hardwood / wood-style floors, a brick fireplace, and a textured ceiling

living room with ceiling fan, a textured ceiling, and light wood-type flooring

Video tour

$10,000 Closing Credit¹

$849,000

4 beds • 3 baths • 3,902 sqft

2955 Lolissa Ln, Winter Park FL 32789

#O6202663, Cathy Sawruk Williams, Listing Office: COLDWELL BANKER REALTY

front of property featuring a front lawn

view of swimming pool featuring french doors, a lanai, ceiling fan, and a patio area

3D tour

$10,000 Closing Credit¹

$1,750,000

4 beds • 4 baths • 3,478 sqft

1350 Lyndale Blvd, Winter Park FL 32789

#O6200787, Brad Young, Listing Office: HOMEVEST REALTY

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161-200 of 206 Results

Explore popular home types in Winter Park, FL

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Schools near Winter Park, FL

Elementary Schools

Brookshire Elementary School
2500 Cady Way
Public District PK-5
Aloma Elementary School
2949 Scarlet Rd
Public District KG-5
Hungerford Elementary School
230 S College Ave
Public District PK-5

Middle Schools

Glenridge Middle School
2900 Upper Park Rd
Public District 6-8

High Schools

Winter Park High School
2100 Summerfield Rd
Public Magnet 9-12

Data provided by Great Schools

Housing market reports in Orange County

Homes for sale near Winter Park, FL

Real estate in Winter Park neighborhoods

Top real estate cities in Florida

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Last updated on: 3/15/2025, 12:20:49 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.

IDX Copyright © 2025 Multiple Listing Service of South Brevard, Inc. and Space Coast Association of REALTORS, Inc. All rights reserved. The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity™ Program of Space Coast Multiple Listing Service. IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information Deemed Reliable But Not Guaranteed. Real estate listings held by brokerage firms other this broker are marked with the Broker Reciprocity™ logo or the Broker Reciprocity™ thumbnail logo (a little black house) and detailed information about them includes the name of the listing brokers. Some properties which appear for sale on this web site may subsequently have sold and may no longer be available.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 3/15/2025, 12:20:56 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.