105 Results

Winter Park Homes For Sale & Winter Park FL Real Estate from $1 million and Up

Home For Sale $7,250,000

View 500 N Interlachen Ave Winter Park FL
View Details 72 Photos
View 500 N Interlachen Ave Winter Park FL
View 500 N Interlachen Ave Winter Park FL
View 500 N Interlachen Ave Winter Park FL
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4581

  • Year Built

    1934

  • $/SqFt

    $1,583

Located in charming Winter Park, FL, this magnificent estate is just a short walk to award-winning dining and boutique shops as well as the Alfond Inn, Rollins College, and many other nearby historic sites and attractions. MLS#O6206309. KELLY PRICE & COMPANY LLC.

Home For Sale $2,795,000

View 2412 Chantilly Ave Winter Park FL
View Details 63 Photos
View 2412 Chantilly Ave Winter Park FL
View 2412 Chantilly Ave Winter Park FL
View 2412 Chantilly Ave Winter Park FL
On Market For 2 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4500

  • Year Built

    2024

  • $/SqFt

    $621

Winter Park Village - Experience the pinnacle of luxury living with this exceptional new construction home. MLS#O6206511. COMPASS FLORIDA LLC.

Pended $5,500,000

View 75 Palmer Ave Winter Park FL
View Details 18 Photos
View 75 Palmer Ave Winter Park FL
View 75 Palmer Ave Winter Park FL
View 75 Palmer Ave Winter Park FL
On Market For 1 Day

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    3442

  • Year Built

    1940

  • $/SqFt

    $1,598

Don't miss this rare opportunity to experience the ultimate blend of luxury, convenience and natural beauty. MLS#O6195846. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,895,000

View 1540 Palm Ave Winter Park FL
View Details 64 Photos
View 1540 Palm Ave Winter Park FL
View 1540 Palm Ave Winter Park FL
View 1540 Palm Ave Winter Park FL
On Market For 3 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3423

  • Year Built

    2014

  • $/SqFt

    $554

Lake Knowles Terrace - Original Windsor Home-http://www.nicolegibbonsstyle.com/2012/07/magnificent-house-windsor-gwyneth-paltrow.html

MLS#O6205484. KELLY PRICE & COMPANY LLC.

Pended $1,495,000

View Details 1 Photo
On Market For 1 Day

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3272

  • Year Built

    1956

  • $/SqFt

    $457

Minutes to top-notch public and private schools. MLS#O6200361. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,350,000

View Details 71 Photos
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2688

  • Year Built

    2004

  • $/SqFt

    $502

Conveniently located just minutes away from Winter Park's upscale retail and dining options, don’t miss your opportunity to make this home yours today! MLS#O6195756. KELLY PRICE & COMPANY LLC.

Home For Sale $1,325,000

View Details 31 Photos
*POTENTIAL GREAT VALUE
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3834

  • Year Built

    1940

  • $/SqFt

    $346

Golfview - Schedule a showing today and make this your dream home! MLS#O6204804. COSTAL LIGHTHOUSE INVESTMENTS.

Home For Sale $1,089,000

View Details 38 Photos
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2267

  • Year Built

    1986

  • $/SqFt

    $480

Schedule a showing today and experience the allure 1621 Lasbury Avenue has to offer. MLS#O6202020. COMPASS FLORIDA LLC.

Home For Sale $5,200,000

View Details 32 Photos
On Market For 9 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5681

  • Year Built

    1985

  • $/SqFt

    $915

Virginia Heights - Don't miss your chance to own this exceptional lakefront estate property, where every day feels like a vacation. Schedule your private tour today! MLS#O6203847. PREMIER SOTHEBY'S INTL. REALTY.

Pended $1,895,000

View Details 47 Photos
On Market For 4 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3059

  • Year Built

    1989

  • $/SqFt

    $619

Comstock Park - Contact us today to schedule a private viewing and make this your dream home. MLS#O6203973. CORCORAN PREMIER REALTY.

Home For Sale $1,895,000

View Details 46 Photos
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3653

  • Year Built

    1951

  • $/SqFt

    $519

Cloister Grove - Do not miss the opportunity to live in one of Winter Park’s most sought after neighborhoods. MLS#O6203731. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,000,000

View Details 15 Photos
*POTENTIAL GREAT VALUE
On Market For 79 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3902

  • Year Built

    1969

  • $/SqFt

    $256

Just 4 miles to downtown Park Avenue shopping and dining district. MLS#O6202663. COLDWELL BANKER REALTY.

Home For Sale $3,125,000

View Details 54 Photos
On Market For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3576

  • Year Built

    2007

  • $/SqFt

    $874

Of course, the location is one of the most outstanding features of this home- Walk to Farmers market, Park Avenue shoppes and restaurants and of course the Winter park 9 just one house away. MLS#O6203301. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,499,900

View Details 55 Photos
On Market For 19 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2846

  • Year Built

    2003

  • $/SqFt

    $527

Charmont - See links for WALKTHROUGH VIDEO and MATTERPORT TOUR. MLS#O6201138. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $1,895,000

View Details 35 Photos
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3217

  • Year Built

    1952

  • $/SqFt

    $589

Cloister Grove - An exclusive respite, this home represents the epitome of Winter Park living at its finest. MLS#O6202026. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,850,000

View Details 72 Photos
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3478

  • Year Built

    2003

  • $/SqFt

    $532

Dixie Terrace - Welcome to your new home in Winter Park, designed for those who desire the very best in life. MLS#O6200787. HOMEVEST REALTY.

Pended $1,099,000

View Details 35 Photos
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2169

  • Year Built

    1958

  • $/SqFt

    $507

With all these fabulous highlights combined, this home promises an exceptional living experience! MLS#O6200234. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,650,000

View Details 26 Photos
On Market For 15 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3731

  • Year Built

    2024

  • $/SqFt

    $710

View detailed design and inspiration deck at https://urbanperchhomes.com/1791-taylor-avenue-winter-park-fl-32789-custom-home/ MLS#O6202078. KELLER WILLIAMS WINTER PARK.

Pended $1,575,000

View Details 50 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3245

  • Year Built

    2016

  • $/SqFt

    $485

Brookshire Heights - * Video depicts yellow front door, this has been updated to Blue* MLS#O6199777. PREFERRED REAL ESTATE BROKERS.

Home For Sale $1,895,000

View Details 40 Photos
On Market For 16 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3361

  • Year Built

    2007

  • $/SqFt

    $564

Charmont - Discover the perfect blend of historic charm and modern luxury in this exquisite home—a true sanctuary in the heart of Winter Park. MLS#O6201554. PREMIER SOTHEBY'S INTL. REALTY.

Pended $1,649,000

View Details 78 Photos
On Market For 12 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3028

  • Year Built

    2006

  • $/SqFt

    $545

Don't miss your chance to experience the epitome of gracious living in one of Florida's most coveted neighborhoods. MLS#O6200815. EXP REALTY LLC.

Home For Sale $1,489,000

View Details 36 Photos
On Market For 17 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2812

  • Year Built

    2001

  • $/SqFt

    $530

Experience the epitome of lakeside living and make this dream home yours today. MLS#O6199613. SOTERA LIVING.

Home For Sale $1,590,000

Reduced By $60,000
View Details 61 Photos
On Market For 18 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3233

  • Year Built

    1953

  • $/SqFt

    $492

Maitland Shores - Experience the allure of Winter Park living at 940 Moss Lane, where each day unfolds with the promise of new adventures and endless possibilities. Schedule your private visit today. MLS#O6200641. MAINFRAME REAL ESTATE.

Pended $1,320,000

View Details 34 Photos
On Market For 2 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3248

  • Year Built

    2015

  • $/SqFt

    $406

Conveniently located, this community offers easy access to SR 417, UCF, Rollins College, downtown Winter Park and Orlando. MLS#O6198447. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,950,000

View Details 3 Photos
On Market For 20 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2701

  • Year Built

    2024

  • $/SqFt

    $722

Sylvan Heights - Completing this house is the clean outdoor living space with a custom detailed ceiling and flooring creating a seamless transition from the living space to the pool entertainment space. MLS#O6199494. THE HOPE GROUP.

Home For Sale $11,795,000

View Details 48 Photos
*POTENTIAL GREAT VALUE
On Market For 23 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    8188

  • Year Built

    2021

  • $/SqFt

    $1,441

Don't miss the opportunity to make this your own private paradise. MLS#O6199109. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $4,150,000

View Details 59 Photos
*POTENTIAL GREAT VALUE
On Market For 23 Days

  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    6939

  • Year Built

    1999

  • $/SqFt

    $598

Comstock Park - With its timeless elegance and modern amenities, this home offers a unique lifestyle of comfort and sophistication in the heart of Winter Park. MLS#O6199396. PALMANO GROUP RE BROKERAGE LLC.

Home For Sale $1,690,000

View Details 57 Photos
On Market For 23 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3518

  • Year Built

    1964

  • $/SqFt

    $480

Green Oaks - Schedule your private tour today and discover the luxury and sophistication of 1801 Legion Dr. MLS#O6199755. FANNIE HILLMAN & ASSOCIATES.

Pended $4,500,000

View Details 67 Photos
On Market For 18 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5320

  • Year Built

    2002

  • $/SqFt

    $846

Close to the charming boutiques and restaurants on Park Avenue. MLS#O6199601. FANNIE HILLMAN & ASSOCIATES.

Pended $2,100,000

View Details 82 Photos
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3300

  • Year Built

    1987

  • $/SqFt

    $636

Sylvan Lake Shores - Don't miss the opportunity to experience the captivating charm and natural beauty of this Winter Park gem.

MLS#O6199085. KELLY PRICE & COMPANY LLC.

Home For Sale $2,495,000

View Details 48 Photos
On Market For 27 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3154

  • Year Built

    1951

  • $/SqFt

    $791

Schedule you're showing today and experience the epitome of luxury living at 1161 Lincoln Circle." MLS#O6198338. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $4,250,000

View Details 19 Photos
On Market For 30 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3660

  • Year Built

    2024

  • $/SqFt

    $1,161

Call now to schedule your meeting with the Builder and get started on your new home! MLS#O6193386. UNITED REAL ESTATE PREFERRED.

Pended $1,800,000

View Details 55 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3404

  • Year Built

    1990

  • $/SqFt

    $529

Lugano Terrace - Bedroom Closet Type: Walk-in Closet (Primary Bedroom). MLS#O6197726. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,995,000

Reduced By $100,000
View Details 61 Photos
On Market For 31 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4216

  • Year Built

    2020

  • $/SqFt

    $710

Comstock Park - Don't miss your opportunity to own a piece of Winter Park's finest. Schedule your private showing today! MLS#O6196961. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,690,000

Reduced By $102,000
View Details 59 Photos
On Market For 34 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3330

  • Year Built

    2017

  • $/SqFt

    $508

Golf and tennis neighborhood Racquet Club, Interlachen Country Club, and Winter Park 9 Golf Course.

MLS#O6194670. KELLY PRICE & COMPANY LLC.

Pended $1,117,500

Reduced By $57,500
View Details 25 Photos
On Market For 21 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2797

  • Year Built

    1980

  • $/SqFt

    $400

Plus, with sought-after Winter Park schools just a stone's throw away, you'll enjoy peace of mind knowing your family is in a top-notch educational environment. MLS#O6195768. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,400,000

View Details 11 Photos
On Market For 39 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    1947

  • $/SqFt

    $972

Charmont - The last time a house sold on this street was four years ago. MLS#V4935671. GREENE REALTY OF FLORIDA LLC.

Home For Sale $6,650,000

Reduced By $345,000
View Details 52 Photos
On Market For 43 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4792

  • Year Built

    1998

  • $/SqFt

    $1,388

Sicilian Shores - Roof and boathouse roof updated 2022. MLS#O6195529. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $1,899,700

Reduced By $89,000
View Details 26 Photos
On Market For 43 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2859

  • Year Built

    1948

  • $/SqFt

    $664

Kronenberger - Bedroom Closet Type: Walk-in Closet (Primary Bedroom). MLS#O6193303. FLORIDA PROPERTY LLC.

Home For Sale $1,350,000

Reduced By $145,000
View Details 56 Photos
On Market For 41 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3074

  • Year Built

    2017

  • $/SqFt

    $439

Ideally situated near Lakemont Elementary, Publix, Advent Health, and mere minutes from Park Avenue. MLS#O6194226. THE HOPE GROUP.

Pended $1,995,000

View Details 22 Photos
On Market For 35 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4738

  • Year Built

    1948

  • $/SqFt

    $421

Woodmere Terrace - Experience the essence of timeless elegance and modern comfort at this remarkable address. MLS#O6193348. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,695,000

View Details 71 Photos
On Market For 44 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3150

  • Year Built

    2006

  • $/SqFt

    $538

Charmont - Schedule your private showing today before it's SOLD! MLS#O6193582. VOSS REALTY INC.

Pended $1,325,000

View Details 66 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2942

  • Year Built

    2006

  • $/SqFt

    $450

Windsong Elizabeths Walk - Central Florida living at its best in one of Winter Park's most sought-after communities. MLS#O6192936. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $2,199,999

View Details 67 Photos
On Market For 47 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3971

  • Year Built

    1990

  • $/SqFt

    $554

College Place - With its architectural integrity, handcrafted details, central location, enchanting central skylight, and minutes’ walk to Lake Virginia and Park Avenue, it is a rare find that epitomizes the art of living in sunny Florida. MLS#O6190102. NEXTHOME MY WAY.

Pended $1,374,900

View Details 89 Photos
On Market For 15 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3252

  • Year Built

    2024

  • $/SqFt

    $423

Golfview - Make an appointment to see this beautiful home today. MLS#O6193452. RE/MAX EXCLUSIVE COLLECTION.

Home For Sale $3,890,000

View Details 3 Photos
On Market For 46 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4055

  • Year Built

    2025

  • $/SqFt

    $959

Room Feature: Linen Closet In Bath (Primary Bedroom). MLS#O6191966. CORCORAN PREMIER REALTY.

Home For Sale $2,250,000

View Details 54 Photos
On Market For 46 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3276

  • Year Built

    1995

  • $/SqFt

    $687

Don't miss your chance to make this exquisite property your own and enjoy the epitome of Florida luxury living. MLS#O6192372. KELLER WILLIAMS WINTER PARK.

Pended $2,200,000

View Details 100 Photos
On Market For 19 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4176

  • Year Built

    2004

  • $/SqFt

    $527

Windsong Lookout Landing - Schedule your showing today and envision your lifestyle in this remarkable sanctuary.

MLS#O6181952. KELLY PRICE & COMPANY LLC.

Home For Sale $2,749,000

View Details 61 Photos
On Market For 53 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4692

  • Year Built

    2007

  • $/SqFt

    $586

Zoned for Audubon K-8 and WP High School. MLS#O6190641. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $2,150,000

Reduced By $100,000
View Details 48 Photos
On Market For 55 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3102

  • Year Built

    1989

  • $/SqFt

    $693

Kronenberger - WELCOME HOME to the the Winter Park lifestyle at its finest! MLS#O6181050. FANNIE HILLMAN & ASSOCIATES.

Viewing HOMES 1 to 50 of 105

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 407-278-2057 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$577,014
$445,000
93
1.1%
37.6%
79

Apopka
$511,793
$471,045
506
1.6%
43.3%
78

Belle Isle
$872,141
$725,000
27
3.7%
55.6%
67

Casselberry
$446,043
$447,000
68
4.4%
44.1%
74

Celebration
$1,409,400
$1,237,450
54
0.0%
51.9%
110

Champions Gate
$664,542
$694,500
28
0.0%
42.9%
175

Chuluota
$1,193,392
$578,700
26
3.8%
53.8%
68

Clermont
$581,440
$499,000
567
0.7%
45.5%
88

Gotha
$938,269
$582,450
16
0.0%
43.8%
58

Groveland
$460,794
$413,285
203
1.5%
42.4%
73

Harmony
$440,904
$424,945
52
1.9%
55.8%
99

Kissimmee
$536,798
$459,900
1908
0.7%
45.1%
99

Longwood
$770,727
$619,900
181
1.1%
42.5%
65

Maitland
$1,176,559
$650,000
70
0.0%
35.7%
85

Minneola
$567,527
$528,495
110
0.0%
23.6%
84

Montverde
$1,668,066
$1,190,999
57
0.0%
35.1%
135

Ocoee
$547,006
$489,450
124
1.6%
41.1%
64

Orlando
$690,305
$499,000
2314
1.5%
40.5%
85

Oviedo
$682,426
$599,000
171
0.6%
34.5%
52

Poinciana
$330,468
$319,900
433
0.7%
53.6%
127

Reunion
$1,641,983
$1,200,000
87
0.0%
55.2%
168

Saint Cloud
$529,031
$458,750
882
0.1%
43.8%
92

Sanford
$520,727
$427,000
368
0.3%
53.5%
90

Sorrento
$651,626
$489,900
100
0.0%
53.0%
78

Windermere
$2,352,916
$1,485,000
238
0.8%
45.0%
93

Winter Garden
$839,407
$699,900
563
0.0%
38.2%
80

Winter Springs
$558,182
$510,000
124
1.6%
44.4%
60

EasyStreet

Call to Schedule a Showing

(407) 278-2057

(407) 278-2057