Winter Park, FL homes for sale & real estate

337 homes

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ABOUT THIS HOME
Winter Park, FL Homes for Sale
Welcome to 1451 Cavendish Road, a beautifully renovated home in the heart of Orwin Manor, one of Winter Park's most desirable and family-friendly neighborhoods. Set on a large and prominent corner lot, this move-in-ready home perfectly balances charm, safety, and convenience just minutes from Park Avenue, Downtown Orlando, and the Mills District. Enjoy extensive upgrades including new AC, attic insulation, electrical panels, water lines, laundry closet, and outdoor ventilated bathroom fans and kitchen vent. Smart-home features include app-controlled lock, Rain Bird sprinklers with rain sensor, and optional security cameras. The exterior features new landscaping, EV charger, extended circula

$619,500

3 beds2 baths1,437 sq ft

1451 Cavendish Rd, Winter Park, FL 32789

Renovated home • New landscaping • Ev charger

ABOUT THIS HOME
Winter Park, FL Homes for Sale
Amazing Townhome! GATED Community of Aloma Trails Townhomes in a great Winter Park location and this 3 bedroom, 2.5 bathroom with features of spacious living and comfortability. This stunning Townhome has Ceramic Tile flooring throughout the first floor leads to a kitchen with all the upgrades including SS appliances. 42” Cabinets, upgraded granite countertops and backsplash, and an island with plenty of seating along with a carpet in the second floor and all bedrooms. The master suite is outfitted with large Walk-In closet, glass-enclosed shower with dual sinks, and oversized cabinets. The two additional bedrooms share a second full bath and there is a half bath on the main floor con

$359,500

3 beds3.5 baths1,872 sq ft

7580 Aloma Pines Ct, Winter Park, FL 32792

Gated community • Dual sinks • Walk-in closet

ABOUT THIS HOME
Winter Park, FL Homes for Sale
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
Winter Park, FL Homes for Sale
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

$3,499,000

5 beds6 baths4,143 sq ft

516 Henkel Cir, Winter Park, FL 32789

Solid wood flooring • 1.32 acre lot • Travertine flooring

ABOUT THIS HOME
Winter Park, FL Homes for Sale
Unlock potential in one of Central Florida’s most desirable pockets! This centrally located Winter Park home shines with major updates already completed including a 2018 roof, 2022 HVAC, and fresh interior paint. Just bring a little extra love to elevate the finishes and create instant equity. Perfect as a long-term rental, short-term investment, or a future flip with strong resale appeal. Live minutes from Winter Park shopping & dining, beautiful golf courses, and vibrant Downtown Orlando. Commuting stays easy with quick access to top employers, schools, and major roadways. Whether you’re crafting your next investment win or dreaming up a place of your own, this home deli

$269,000

2 beds1 bath762 sq ft

2009 Cornell Ave, Winter Park, FL 32789

2018 roof • 2022 hvac • Central location

Property at 550 Palmer Ave, Winter Park, FL 32789, 5 beds, 6.5 baths

$7,200,000

5 beds6.5 baths5,939 sq ft

550 Palmer Ave, Winter Park, FL 32789

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

$733,000

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 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 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 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

$635,000

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

$159,000

1 bed1 bath749 sq ft

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

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 607 Ellen Dr, Winter Park, FL 32789, 4 beds, 4 baths

$1,630,000

4 beds4 baths2,812 sq ft

607 Ellen Dr, 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

$1,875,000

4 beds2.5 baths2,674 sq ft

633 Balmoral Rd, Winter Park, FL 32789

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

$250,000

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 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 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 640 Park Ave N #26, Winter Park, FL 32789, 2 beds, 2 baths

$572,500

2 beds2 baths858 sq ft

640 Park Ave N #26, Winter Park, FL 32789

Property at 1302 Raintree Pl, Winter Park, FL 32789, 5 beds, 5.5 baths

$5,300,000

5 beds5.5 baths4,738 sq ft

1302 Raintree Pl, 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 457 E New England Ave, Winter Park, FL 32789, 5 beds, 4.5 baths

$3,100,000

5 beds4.5 baths3,847 sq ft

457 E New England Ave, Winter Park, FL 32789

Property at 2420 Firstlight Way, Winter Park, FL 32792, 3 beds, 2.5 baths

$460,000

3 beds2.5 baths2,312 sq ft

2420 Firstlight Way, Winter Park, FL 32792

Property at 668 Overspin Dr, Winter Park, FL 32789, 4 beds, 3 baths

$950,000

4 beds3 baths2,509 sq ft

668 Overspin Dr, Winter Park, FL 32789

Property at 1695 Lee Rd Unit C214, Winter Park, FL 32789, 2 beds, 1 bath

$123,000

2 beds1 bath881 sq ft

1695 Lee Rd Unit C214, Winter Park, FL 32789

Property at 5275 Pine Lily Cir, Winter Park, FL 32792, 5 beds, 3.5 baths

$709,000

5 beds3.5 baths3,152 sq ft

5275 Pine Lily Cir, Winter Park, FL 32792

Property at 1540 Miller Ave, Winter Park, FL 32789, 4 beds, 3.5 baths

$1,399,900

4 beds3.5 baths2,984 sq ft

1540 Miller Ave, Winter Park, FL 32789

Property at 1510 Miller Ave, Winter Park, FL 32789, 5 beds, 4.5 baths

$1,634,900

5 beds4.5 baths3,252 sq ft

1510 Miller Ave, Winter Park, FL 32789

Property at 7326 Swallow Run #7326, Winter Park, FL 32792, 2 beds, 2 baths

$136,000

2 beds2 baths800 sq ft

7326 Swallow Run #7326, Winter Park, FL 32792

Property at 1120 Preserve Point Dr, Winter Park, FL 32789, 7 beds, 10 baths

$8,950,000

7 beds10 baths11,255 sq ft

1120 Preserve Point Dr, Winter Park, FL 32789

Property at 1422 Tierra Cir, Winter Park, FL 32792, 4 beds, 2 baths

$499,000

4 beds2 baths1,827 sq ft

1422 Tierra Cir, Winter Park, FL 32792

Property at 1816 Ivy Ln, Winter Park, FL 32792, 4 beds, 2 baths

$425,000

4 beds2 baths1,725 sq ft

1816 Ivy Ln, Winter Park, FL 32792

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Based on information submitted to the MLS GRID as of Sun Dec 21 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.

Average home prices near Winter Park, FL

Cities

Clermont homes for sale
$451,975
Altamonte Springs homes for sale
$199,393
Windermere homes for sale
$1,717,500
Longwood homes for sale
$395,000
Ocoee homes for sale
$473,990
Mount Dora homes for sale
$437,000
Maitland homes for sale
$354,950
Sanford homes for sale
$359,000
Orlando homes for sale
$329,000
Kissimmee homes for sale
$340,000
Oviedo homes for sale
$460,100
Winter Garden homes for sale
$632,400
Apopka homes for sale
$450,000
Lake Mary homes for sale
$569,900
Deltona homes for sale
$325,000

Neighborhoods
Zip Codes

Audubon Park homes for sale
$641,400
Virginia Heights homes for sale
$3,142,500
Winter Park Downtown Historic District homes for sale
College Park homes for sale
$792,450
Winter Park Pines homes for sale
$564,000
Windsong homes for sale
$3,499,000
Baldwin Park homes for sale
$705,000
Downtown Maitland homes for sale
$525,000
Orwin Manor homes for sale
$880,000
North Orange homes for sale
$259,500

Winter Park, FL real estate trends

All Home Types trends in Winter Park, FL

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$765,000

-9.47% YoY | Nov 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Nov 2025

Growth

% YoY

Winter Park, FL

$765,000

-9.47%

See more Winter Park, FL market insights

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