Single family homes for sale in Winter Park, FL

206 Listings

ranch-style home featuring an attached garage, concrete driveway, and roof with shingles

single story home featuring concrete driveway, roof with shingles, an attached garage, a front yard, and brick siding

$6,975 Closing Credit¹

$587,400

4 beds • 2.5 baths • 2,260 sqft

3822 Kinsley Pl, Winter Park FL 32792

#A4641055, Donna Mink, Listing Office: MINK REALTY

single story home with a front yard, roof with shingles, and stucco siding

foyer with a textured ceiling, baseboards, and light tile patterned floors

entrance foyer featuring a textured ceiling, a notable chandelier, visible vents, and light wood-style floors

$5,522 Closing Credit¹

$465,000

4 beds • 2.5 baths • 1,948 sqft

7565 Dockside St, Winter Park FL 32792

#O6285857, Maurince Pierre, LLC, Listing Office: PREMIUM PROPERTIES REAL ESTATE

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ranch-style house featuring a garage, a front yard, decorative driveway, and central air condition unit

doorway with baseboards and light tile patterned floors

$6,174 Closing Credit¹

$519,900

3 beds • 2 baths • 1,630 sqft

519 Cornwall Rd, Winter Park FL 32792

#O6286218, Evelyn Pilchick, Listing Office: RE/MAX 200 REALTY

view of front of property with a garage, concrete driveway, roof with shingles, and stucco siding

ranch-style house featuring an attached garage, a front lawn, concrete driveway, and stucco siding

ranch-style home featuring driveway, a front yard, an attached garage, and stucco siding

Video tour

$4,156 Closing Credit¹

$350,000

3 beds • 2 baths • 1,114 sqft

3361 Hamlet Loop, Winter Park FL 32792

#O6286222, Annie Resto, Listing Office: EMPIRE NETWORK REALTY

exterior space featuring a yard, a chimney, a balcony, and stucco siding

exterior space featuring a balcony and stucco siding

exterior space featuring driveway, a chimney, and stucco siding

Video tour

$4,875,000

4 beds • 5 baths • 4,431 sqft

229 Alexander Pl, Winter Park FL 32789

#O6281892, Julie Bombardo, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

bungalow with roof with shingles, fence, a carport, and a front yard

view of front facade with driveway, a shingled roof, an attached garage, fence, and a front yard

living room with light wood finished floors, baseboards, visible vents, and a wealth of natural light

Video tour

$5,105 Closing Credit¹

$429,900

3 beds • 2 baths • 1,200 sqft

1975 Staunton Ave, Winter Park FL 32789

#O6285965, Marion McGrath, Listing Office: ABSOLUTE REALTY GROUP, LLC

ranch-style home with brick siding, a shingled roof, a garage, driveway, and a front lawn

single story home featuring a shingled roof and brick siding

foyer entrance with arched walkways, a textured ceiling, wood finished floors, baseboards, and wallpapered walls

$8,894 Closing Credit¹

$749,000

4 beds • 2 baths • 2,446 sqft

1321 Medinah Ct, Winter Park FL 32792

#O6285649, Courtney Pelfrey, Listing Office: MILLER GRANT AND COMPANY

Room to negotiate?

Median Sold Price

$469.6K

Avg. Sale Time

62 Days

Based on our February 2025 Market Report.

living area with a notable chandelier, crown molding, a glass covered fireplace, and a decorative wall

kitchen with a tray ceiling, open shelves, tasteful backsplash, oven, and under cabinet range hood

3D tour

$10,000 Closing Credit¹

$1,799,000

4 beds • 3.5 baths • 3,669 sqft

1731 Windsor Dr, Winter Park FL 32789

#O6285883, James Condino, Listing Office: CHARLES RUTENBERG REALTY ORLANDO

view of front of home featuring decorative driveway, an attached garage, fence, and stucco siding

view of front of home featuring a garage, fence, decorative driveway, and stucco siding

view of front of house featuring a garage, decorative driveway, fence, and stucco siding

Video tour

$7,719 Closing Credit¹

$650,000

4 beds • 2.5 baths • 1,881 sqft

2739 Riddle Dr, Winter Park FL 32789

#TB8355970, JASON OLD, Listing Office: BRAINARD REALTY

ranch-style house featuring a front yard, covered porch, driveway, and an attached garage

entrance to property with covered porch and a garage

property entrance featuring covered porch and ceiling fan

Video tour

$10,000 Closing Credit¹

$1,580,000

4 beds • 3.5 baths • 2,637 sqft

1750 Winchester Dr, Winter Park FL 32789

#O6285335, Michael Ford, Listing Office: FANNIE HILLMAN & ASSOCIATES

contemporary home with a front lawn, decorative driveway, an attached garage, and stucco siding

view of front of house with stucco siding, fence, decorative driveway, and a front yard

hall featuring recessed lighting and baseboards

Video tour

$10,000 Closing Credit¹

$1,500,000

4 beds • 4 baths • 2,958 sqft

2015 Summerfield Rd, Winter Park FL 32792

#O6285086, Steven Koleno, Listing Office: BEYCOME OF FLORIDA LLC

ranch-style house featuring brick siding, driveway, and an attached garage

ranch-style home with concrete driveway, brick siding, and an attached garage

kitchen featuring appliances with stainless steel finishes, brown cabinets, light countertops, and a sink

Video tour

$4,418 Closing Credit¹

$372,000

4 beds • 2 baths • 1,782 sqft

5339 Cypress Dr, Winter Park FL 32792

#O6284337, Fredric Crawford, Listing Office: FUTURE HOME REALTY INC

traditional-style house featuring decorative driveway, a shingled roof, a garage, stone siding, and a front lawn

doorway to property featuring stucco siding

hallway featuring light wood-type flooring and wooden walls

3D tour

$9,738 Closing Credit¹

$820,000

5 beds • 4 baths • 2,866 sqft

5618 Winterbrook Way, Winter Park FL 32792

#TB8352579, Elizabeth Binder, Listing Office: REDFIN CORPORATION

view of front of property with a garage, stone siding, roof with shingles, decorative driveway, and a front lawn

french country style house featuring an attached garage, driveway, stone siding, stucco siding, and a front yard

bedroom featuring access to exterior, crown molding, visible vents, and wood finished floors

Video tour

$10,000 Closing Credit¹

$995,000

4 beds • 3 baths • 2,838 sqft

210 Laurel Park Ct, Winter Park FL 32792

#O6279127, Lizzie Beaudoin, Listing Office: PR REAL ESTATE SERVICES

view of front of house featuring stucco siding

tudor house featuring a tile roof and stucco siding

back of property featuring a tiled roof, a lawn, a patio area, and a fenced in pool

$4,500,000

4 beds • 4 baths • 3,181 sqft

1336 College Pt, Winter Park FL 32789

#O6277515, Mick Night, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

ranch-style house with decorative driveway, fence, and a front lawn

ranch-style house with an attached garage, fence, a front lawn, and decorative driveway

view of yard featuring a rural view and fence

Video tour

$4,976 Closing Credit¹

$419,000

3 beds • 2 baths • 1,214 sqft

3117 Shady Pine Ave, Winter Park FL 32792

#O6283862, Alistair Baxter, Listing Office: EXP REALTY LLC

view of front of property featuring a garage, decorative driveway, and stucco siding

property view of water with a residential view

view of front facade with decorative driveway, a tile roof, stucco siding, an attached garage, and a front lawn

Video tour

$8,906 Closing Credit¹

$750,000

4 beds • 2.5 baths • 2,197 sqft

1312 Blue Stem Ln, Winter Park FL 32792

#O6268066, Maggie Walas, Listing Office: FORTUNE INTERNATIONAL REALTY

view of front of house with an attached garage, driveway, a front lawn, and stucco siding

view of front of home with a front yard, an attached garage, and stucco siding

living area with visible vents, baseboards, light wood-style flooring, ornamental molding, and recessed lighting

Video tour

$2,990,000

8 beds • 6 baths • 7,000 sqft

1860 Via Contessa, Winter Park FL 32789

#O6210791, Sylvester Harding, Listing Office: SIERRA REALTY GROUP LLC

ranch-style house with driveway, stucco siding, and a front yard

kitchen with range, a breakfast bar, a peninsula, white cabinetry, and pendant lighting

kitchen with a breakfast bar, a peninsula, hanging light fixtures, black appliances, and white cabinetry

Video tour

$8,657 Closing Credit¹

$729,000

3 beds • 2 baths • 1,527 sqft

2812 Mulford Ave, Winter Park FL 32789

#O6282074, Haley Young, Listing Office: SYNCHRONICITY REAL ESTATE SOLUTIONS

neoclassical / greek revival house featuring a shingled roof, a lawn, a balcony, a porch, and stucco siding

greek revival house with a porch, a front lawn, a balcony, and stucco siding

exterior space featuring ceiling fan, a patio, a fenced backyard, an outdoor living space, and a fenced in pool

$10,000 Closing Credit¹

$2,500,000

5 beds • 5 baths • 4,676 sqft

450 Lakewood Dr, Winter Park FL 32789

#O6279653, Vonda Fields, Listing Office: CHARLES RUTENBERG REALTY ORLANDO

view of front facade featuring stucco siding

$10,000 Closing Credit¹

$975,000

3 beds • 1 bath • 1,045 sqft

674 W Comstock Ave, Winter Park FL 32789

#O6282808, Frank Baker, Jr, Listing Office: KELLER WILLIAMS WINTER PARK

single story home with a garage, a shingled roof, concrete driveway, fence, and a front lawn

ranch-style home featuring driveway, a garage, a gate, and fence

ranch-style home with concrete driveway, a front lawn, and an attached garage

Video tour

$4,394 Closing Credit¹

$370,000

3 beds • 2 baths • 1,106 sqft

3047 Riverbrook Dr, Winter Park FL 32792

#O6282580, Kristin Duncan, Listing Office: KELLER WILLIAMS ADVANTAGE REAL

modern inspired farmhouse featuring a fenced front yard, a front yard, and driveway

view of dock featuring a yard, a water view, fence, and boat lift

rear view of property with a lawn, a fenced in pool, a patio, fence, and stucco siding

Video tour

$10,000 Closing Credit¹

$2,399,900

4 beds • 5 baths • 3,694 sqft

301 Rippling Ln, Winter Park FL 32789

#A4637563, Cynthia Fernandez, Listing Office: XCLUSIVE HOMES LLC

ranch-style house featuring a front lawn

single story home with a garage, concrete driveway, and a front yard

Video tour

$10,000 Closing Credit¹

$925,000

4 beds • 2 baths • 2,133 sqft

625 Worthington Dr, Winter Park FL 32789

#O6282822, Jennifer Sloan, Listing Office: KELLY PRICE & COMPANY LLC

view of front of property featuring driveway, fence, and stucco siding

traditional style home featuring a tiled roof and a fenced front yard

Video tour

$5,700,000

5 beds • 6.5 baths • 6,406 sqft

1660 Palmer Ave, Winter Park FL 32789

#O6282425, Mick Night, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

view of front of house with driveway and fence

view of pool featuring a fenced in pool, a patio area, a fenced backyard, and an outdoor hangout area

pool at dusk with french doors, a pool with connected hot tub, a patio area, fence, and an outdoor living space

Video tour

$7,362 Closing Credit¹

$619,999

3 beds • 2 baths • 2,268 sqft

701 Denton Rd, Winter Park FL 32792

#O6282779, Kristan Hayden, Listing Office: ATRIUM REALTY, LLC

ranch-style house featuring a garage, concrete driveway, fence, and stucco siding

Video tour

$5,938 Closing Credit¹

$500,000

5 beds • 2.5 baths • 2,158 sqft

7448 Grand Ct, Winter Park FL 32792

#O6281379, Amaal Barakat, Listing Office: KELLER WILLIAMS ADVANTAGE III

ranch-style house featuring a front lawn and a garage

single story home with a front yard and a garage

ranch-style house with a yard and a garage

$6,472 Closing Credit¹

$545,000

4 beds • 3 baths • 1,945 sqft

4200 Bear Gully Rd, Winter Park FL 32792

#O6280157, Renee Killiri, Listing Office: RED BIRD REALTY OF FLORIDA INC

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

$6,531 Closing Credit¹

$550,000

3 beds • 2 baths • 1,115 sqft

720 N Pennsylvania Ave, Winter Park FL 32789

#O6281659, Dominick Florio, Listing Office: RE/MAX TOWN & COUNTRY REALTY

kitchen featuring dark stone countertops, light hardwood / wood-style flooring, appliances with stainless steel finishes, a kitchen breakfast bar, and decorative backsplash

$8,906 Closing Credit¹

$750,000

3 beds • 2 baths • 1,167 sqft

726 N Pennsylvania Ave, Winter Park FL 32789

#O6281654, Dominick Florio, Listing Office: RE/MAX TOWN & COUNTRY REALTY

$10,000 Closing Credit¹

$1,275,000

6 beds • 4 baths • 2,284 sqft

726/720 N Pennsylvania Ave, Winter Park FL 32789

#O6282473, Dominick Florio, Listing Office: RE/MAX TOWN & COUNTRY REALTY

view of front of home featuring a balcony

empty room with light hardwood / wood-style floors

Video tour

$6,412 Closing Credit¹

$539,990

3 beds • 3 baths • 1,920 sqft

423 Ololu Dr, Winter Park FL 32789

#O6281902, tanya Fei, Listing Office: AAA GLOBAL VENTURES PA

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

kitchen with light tile patterned floors, stainless steel appliances, and white cabinetry

kitchen featuring stainless steel appliances, white cabinets, a breakfast bar, a center island, and light tile patterned floors

Video tour

$3,754 Closing Credit¹

$316,090

5 beds • 2.5 baths • 2,112 sqft

1946 Sarah St, Winter Haven FL 33884

#TB8352550, Ben Goldstein, Listing Office: LENNAR REALTY

doorway to property featuring ceiling fan

Video tour

$10,000 Closing Credit¹

$1,350,000

4 beds • 4 baths • 3,000 sqft

181 N Phelps Ave, Winter Park FL 32789

#O6278498, Iluska Kruse, Listing Office: ORLANDO BROTHERS REAL ESTATE LLC

ranch-style home featuring a front lawn and a garage

Video tour

$8,894 Closing Credit¹

$749,000

3 beds • 1.5 baths • 2,108 sqft

5150 Old Howell Branch Rd, Winter Park FL 32792

#O6282162, Sanya Avazpour, Listing Office: COMPASS FLORIDA, LLC

view of front of home with decorative driveway, an attached garage, fence, and stucco siding

Video tour

$10,000 Closing Credit¹

$1,295,000

4 beds • 4 baths • 2,916 sqft

1611 Chestnut Ave, Winter Park FL 32789

#O6281275, Didem Isik-Widener, Listing Office: PARK AVENUE REALTY LLC

contemporary home with a garage and a front lawn

$10,000 Closing Credit¹

$1,675,000

4 beds • 4 baths • 2,812 sqft

607 Ellen Dr, Winter Park FL 32789

#TB8350945, Douglas Addeo, Listing Office: COMMUNITY REALTY ASSOCIATES

ranch-style home featuring a garage and a front yard

single story home with a garage and a front yard

view of front of home featuring a garage and a front lawn

Video tour

$5,225 Closing Credit¹

$439,990

3 beds • 2 baths • 1,326 sqft

7427 Houston Ct E, Winter Park FL 32792

#O6280901, Constantin Florean, Listing Office: FUTURE HOME REALTY INC

view of front facade with driveway, a garage, fence, and a front lawn

kitchen with white cabinetry, stainless steel appliances, light countertops, and open floor plan

interior space with white cabinets, visible vents, light countertops, and pendant lighting

Video tour

$4,976 Closing Credit¹

$419,000

3 beds • 2 baths • 1,581 sqft

7331 Blue Jacket Pl W, Winter Park FL 32792

#O6279146, Cheyanne MacNeill, Listing Office: NETWORTH REALTY OF ORLANDO, LLC

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

ranch-style house with a garage and a front lawn

Video tour

$9,726 Closing Credit¹

$819,000

3 beds • 2 baths • 1,827 sqft

625 Brechin Dr, Winter Park FL 32792

#O6280564, Kelly Price, Listing Office: KELLY PRICE & COMPANY LLC

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41-80 of 206 Results

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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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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, 9:19:53 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.

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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, 9:20:49 AM 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, 9:20:57 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.