93 Results

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

Home For Sale $2,790,000

View 1540 Glencoe Rd Winter Park FL
View Details 40 Photos
View 1540 Glencoe Rd Winter Park FL
View 1540 Glencoe Rd Winter Park FL
View 1540 Glencoe Rd Winter Park FL
On Market For 2 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4905

  • Year Built

    1986

  • $/SqFt

    $569

Virginia Heights - *Walk-through video filmed before kitchen, bathrooms, and whole house repainted in 2022. MLS#U8240071. WWW.HOMEZU.COM.

Home For Sale $2,495,000

View 1161 Lincoln Cir Winter Park FL
View Details 48 Photos
View 1161 Lincoln Cir Winter Park FL
View 1161 Lincoln Cir Winter Park FL
View 1161 Lincoln Cir Winter Park FL
On Market For 3 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 $1,775,000

View 1333 Mayfield Ave Winter Park FL
View Details 54 Photos
View 1333 Mayfield Ave Winter Park FL
View 1333 Mayfield Ave Winter Park FL
View 1333 Mayfield Ave Winter Park FL
On Market For 3 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3159

  • Year Built

    2000

  • $/SqFt

    $562

Temple Heights - This ideal location is just a few blocks from the WP YMCA, grocery stores, restaurants and shopping off Aloma, and a mile or so from Park Ave! MLS#O6194759. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $4,250,000

View 985 Lincoln Cir Winter Park FL
View Details 19 Photos
View 985 Lincoln Cir Winter Park FL
View 985 Lincoln Cir Winter Park FL
View 985 Lincoln Cir Winter Park FL
On Market For 6 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 $1,895,000

View Details 52 Photos
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3504

  • Year Built

    1999

  • $/SqFt

    $541

Osceola Shores - 160 Trismen Terrace is truly a home for those who appreciate entertaining. MLS#O6197555. OLDE TOWN BROKERS INC.

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 - Just a short stroll to the Winter Park Park Racquet Club, this beautiful home is in the top-rated Dommerich Elementary, Maitland Middle, and Winter Park High School district. MLS#O6197726. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $3,095,000

View Details 61 Photos
On Market For 7 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4216

  • Year Built

    2020

  • $/SqFt

    $734

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 $1,792,000

View Details 59 Photos
On Market For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3330

  • Year Built

    2017

  • $/SqFt

    $538

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

MLS#O6194670. KELLY PRICE & COMPANY LLC.

Home For Sale $1,175,000

View Details 25 Photos
On Market For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2797

  • Year Built

    1980

  • $/SqFt

    $420

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 15 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 $6,995,000

View Details 52 Photos
On Market For 19 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4792

  • Year Built

    1998

  • $/SqFt

    $1,460

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

Home For Sale $1,988,700

View Details 26 Photos
On Market For 19 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2859

  • Year Built

    1948

  • $/SqFt

    $696

Kronenberger - Experience the best of Winter Park living with this exceptional property. MLS#O6193303. FLORIDA PROPERTY LLC.

Home For Sale $1,399,999

Reduced By $95,001
View Details 56 Photos
On Market For 17 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3074

  • Year Built

    2017

  • $/SqFt

    $455

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

Home For Sale $1,995,000

View Details 22 Photos
On Market For 21 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 20 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 $1,070,000

View Details 52 Photos
On Market For 20 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3057

  • Year Built

    2015

  • $/SqFt

    $350

Schedule a showing today and experience the beauty of this remarkable home! MLS#O6193168. VR HOMES LLC.

Home For Sale $2,199,999

View Details 67 Photos
On Market For 23 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 22 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4055

  • Year Built

    2025

  • $/SqFt

    $959

Price is subject to change through construction. MLS#O6191966. CORCORAN PREMIER REALTY.

Pended $2,200,000

View Details 54 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3276

  • Year Built

    1995

  • $/SqFt

    $672

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 29 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 $2,250,000

View Details 56 Photos
On Market For 31 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3102

  • Year Built

    1989

  • $/SqFt

    $725

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

Home For Sale $1,200,000

Reduced By $100,000
View Details 57 Photos
On Market For 34 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2752

  • Year Built

    1980

  • $/SqFt

    $436

Don't miss out on this rare opportunity—schedule your showing today! MLS#O6189285. COLDWELL BANKER REALTY.

Home For Sale $2,497,000

View Details 49 Photos
On Market For 39 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3507

  • Year Built

    2024

  • $/SqFt

    $712

Fontainebleau - Be the first to call this incredible home yours as you make your home in Winter Park! MLS#O6187963. KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $1,160,000

Reduced By $25,000
View Details 40 Photos
*POTENTIAL GREAT VALUE
On Market For 35 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3125

  • Year Built

    1954

  • $/SqFt

    $371

Conwill Estates - All this could be yours so schedule your private showing today! MLS#O6189298. CHARLES RUTENBERG REALTY ORLANDO.

Pended $1,495,000

View Details 43 Photos
On Market For 4 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3630

  • Year Built

    2018

  • $/SqFt

    $412

Make this extraordinary Winter Park gem yours! MLS#O6186281. PALMANO GROUP RE BROKERAGE LLC.

Pended $2,575,000

View Details 55 Photos
*POTENTIAL GREAT VALUE
On Market For 37 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5429

  • Year Built

    1983

  • $/SqFt

    $474

Sevilla - You will fall in love with this absolutely spectacular home! ! MLS#O6187903. BEYCOME OF FLORIDA LLC.

Home For Sale $2,245,000

Reduced By $150,000
View Details 42 Photos
On Market For 41 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3897

  • Year Built

    2015

  • $/SqFt

    $576

Flora Park - Located a short golf cart ride from Park Ave’s incredible restaurants and shopping, and walking distance to Phelps Park and the YMCA, the location is impossible to beat. MLS#O6180741. COMPASS FLORIDA, LLC.

Pended $4,950,000

View Details 71 Photos
On Market For 29 Days

  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    4442

  • Year Built

    2024

  • $/SqFt

    $1,114

Sylvan Lake Shores - Welcome home to luxury living at its finest. MLS#O6187383. THE HOPE GROUP.

Home For Sale $3,141,000

View Details 8 Photos
On Market For 42 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4188

  • Year Built

    2024

  • $/SqFt

    $750

Charmont - Inquire with the listing agents for further details, and prepare to be captivated by a lifestyle beyond compare. MLS#O6187136. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $2,890,000

View Details 9 Photos
On Market For 42 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4770

  • Year Built

    2024

  • $/SqFt

    $606

Kenilworth Shores - Don’t miss your opportunity to own this stunning Winter Park home. MLS#O6185001. COMPASS FLORIDA, LLC.

Home For Sale $1,960,000

View Details 10 Photos
On Market For 42 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3499

  • Year Built

    2024

  • $/SqFt

    $560

Northwood Terrace - Please inquire with the listing agents for further details. MLS#O6187113. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,125,000

Reduced By $25,000
View Details 39 Photos
On Market For 43 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2507

  • Year Built

    1993

  • $/SqFt

    $449

Reach out today to schedule a tour on this one of a kind Winter Park charmer. MLS#O6187046. COMPASS FLORIDA LLC.

Home For Sale $7,370,000

View Details 27 Photos
*POTENTIAL GREAT VALUE
On Market For 48 Days

  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    6774

  • Year Built

    2024

  • $/SqFt

    $1,088

Cloister Grove - Please inquire with the list agent for further details. MLS#O6183317. PREMIER SOTHEBY'S INTL. REALTY.

Pended $2,395,000

View Details 42 Photos
On Market For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3910

  • Year Built

    1998

  • $/SqFt

    $613

Osceola Shores - You will feel like you are at a five-star resort! This is a gem! MLS#O6185665. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,050,000

Reduced By $145,000
View Details 46 Photos
On Market For 50 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2472

  • Year Built

    1947

  • $/SqFt

    $425

Virginia Heights - Includes deeded access to Dinky Dock near Rollins College. MLS#O6179037. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $3,499,000

View Details 54 Photos
On Market For 56 Days

  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    4551

  • Year Built

    1990

  • $/SqFt

    $769

Lugano Terrace - New Windows, both New Water Heaters, New Plumbing and many more. MLS#O6183188. CASTLE REALTY PROFESSIONAL GROUP LLC.

Home For Sale $2,299,900

Reduced By $195,100
View Details 45 Photos
On Market For 55 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2925

  • Year Built

    1925

  • $/SqFt

    $786

Virginia Heights - This is the perfect family or forever home. MLS#G5077473. POTOMAC LAND COMPANY.

Home For Sale $2,975,000

Reduced By $175,000
View Details 18 Photos
On Market For 57 Days

  • Bedrooms

    6

  • Full Bath(s)

    3

  • Sq. Ft.

    4522

  • Year Built

    2009

  • $/SqFt

    $658

Windsong - Your dream of owning a luxurious retreat in Winter Park awaits—schedule your private viewing today and elevate your lifestyle to new heights of splendor and distinction. MLS#O6182544. TRUVISION REAL ESTATE LLC.

Home For Sale $1,299,999

Reduced By $25,001
View Details 40 Photos
On Market For 63 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2100

  • Year Built

    1958

  • $/SqFt

    $619

Sells Terrace - This is a one of a kind property, you have to see to believe! MLS#O6181408. EXP REALTY LLC.

Pended $1,200,000

View Details 26 Photos
On Market For 25 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2395

  • Year Built

    1950

  • $/SqFt

    $501

Forrest Hills - Call now to schedule a private showing! Location, Location, Location! MLS#O6179505. PALM PROPERTIES OF CF, INC..

Home For Sale $1,980,000

View Details 50 Photos
On Market For 63 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2857

  • Year Built

    2024

  • $/SqFt

    $693

Lake Killarney Shores - Experience the epitome of luxury living in Winter Park with this exceptional home. MLS#O6181258. SOTERA LIVING.

Home For Sale $1,750,000

View Details 53 Photos
On Market For 63 Days

  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    4173

  • Year Built

    2019

  • $/SqFt

    $419

Roof - 2018, Hvac (2) - 2018, Plumbing - 2018, Electric - 2018. MLS#O6180799. KELLER WILLIAMS WINTER PARK.

Pended $1,595,000

Reduced By $135,000
View Details 91 Photos
On Market For 44 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3151

  • Year Built

    1978

  • $/SqFt

    $506

Recognized design firm PHIL KEAN has produce an Architectural design for this property that would increase the value of the property, current owner are including the drawings as part of the package. SEE RENDERINGS ATTACHED. MLS#O6178427. FORTUNE INTERNATIONAL REALTY.

Home For Sale $1,500,000

Reduced By $99,000
View Details 73 Photos
*POTENTIAL GREAT VALUE
On Market For 64 Days

  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    6252

  • Year Built

    1994

  • $/SqFt

    $240

You will want to show this beauty to your most discriminating Buyers. MLS#O6180611. KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $2,250,000

Reduced By $50,000
View Details 58 Photos
On Market For 69 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4312

  • Year Built

    2004

  • $/SqFt

    $522

Sylvan Park - Ideal for family living, walkability and entertaining. MLS#O6179257. PREMIER SOTHEBY'S INTL. REALTY.

Pended $1,349,000

Reduced By $51,000
View Details 35 Photos
On Market For 50 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2894

  • Year Built

    1998

  • $/SqFt

    $466

Enjoy peace, serenity, and the ultimate feeling of old Winter Park in this stately home, located in the Audubon K-8 school district and minutes away from the best Orlando has to offer. MLS#O6179374. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,950,000

Reduced By $200,000
View Details 40 Photos
On Market For 70 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3924

  • Year Built

    2020

  • $/SqFt

    $752

Tuscany Terrace - The Vias is an unsurpassed Winter Park neighborhood, just a few minutes away from downtown Winter Park/Park Avenue, A-rated schools, Winter Park Racquet Club, Interlachen Country Club and much more. MLS#O6178928. PREMIER SOTHEBY'S INTL. REALTY.

Viewing HOMES 1 to 50 of 93

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
$586,134
$439,900
97
2.1%
35.1%
79

Apopka
$506,870
$464,950
470
1.5%
42.6%
81

Belle Isle
$861,382
$699,990
23
4.3%
65.2%
66

Casselberry
$443,292
$425,000
82
4.9%
41.5%
67

Celebration
$1,371,983
$1,150,000
61
0.0%
47.5%
103

Champions Gate
$661,210
$667,500
28
0.0%
35.7%
158

Chuluota
$1,389,355
$591,250
18
0.0%
44.4%
60

Clermont
$572,809
$498,800
579
0.7%
43.4%
93

Gotha
$1,030,573
$529,000
15
0.0%
66.7%
53

Groveland
$478,039
$421,800
193
1.6%
45.6%
74

Harmony
$440,011
$420,000
57
0.0%
45.6%
85

Kissimmee
$538,563
$464,500
1843
0.7%
44.3%
102

Longwood
$778,162
$570,000
173
1.2%
38.2%
61

Maitland
$1,139,229
$675,000
63
0.0%
49.2%
87

Minneola
$545,508
$533,918
116
0.0%
25.9%
78

Montverde
$1,577,148
$1,136,034
55
0.0%
36.4%
127

Ocoee
$563,382
$527,000
121
1.7%
46.3%
74

Orlando
$684,937
$492,990
2259
1.7%
40.8%
91

Oviedo
$691,278
$609,000
153
0.0%
38.6%
54

Poinciana
$334,284
$320,000
478
0.8%
49.6%
117

Reunion
$1,664,305
$1,199,000
97
0.0%
58.8%
172

Saint Cloud
$519,529
$452,145
826
0.2%
43.1%
101

Sanford
$507,840
$424,870
381
0.8%
51.4%
88

Sorrento
$641,555
$467,290
82
0.0%
53.7%
83

Windermere
$2,409,351
$1,467,500
222
1.4%
44.6%
99

Winter Garden
$853,152
$710,950
508
0.2%
36.8%
81

Winter Springs
$551,359
$496,750
116
0.0%
39.7%
60

EasyStreet

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