Winter Park, FL homes for sale & real estate

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ABOUT THIS HOME
Winter Park, FL Homes for Sale
Luxurious waterfront estate in one of Winter Park’s most prestigious neighborhoods, offering 7,278 SF of elegant living with direct canal access to Lake Maitland. This 5-bedroom, 6.5-bath home features all en-suite bedrooms, including two on the main floor, a gourmet kitchen with Viking appliances, three fireplaces, a theater room, a game room, an office, dual laundry rooms, and dual staircases. Enjoy a heated saltwater pool and spa, summer kitchen, and pool bath. Boathouse, dock with lift, and jet ski dock included. Recent upgrades: all new AC units, pool equipment, landscaping, fencing, and gates. Fully fenced with a security system and a rare 5-car garage, this property offers priv

$5,495,000

5 beds6.5 baths7,278 sq ft

2211 Azalea Pl, Winter Park, FL 32789

Waterfront estate • Theater room • Dual laundry rooms

(305) 400-6393

ABOUT THIS HOME
Winter Park, FL Homes for Sale
Back on market at no fault of the seller! Brand new Roof and HVAC systems 2025. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and modern comfort. This captivating 4-bedroom, 3-bathroom home exudes warmth and sophistication, creating an inviting haven for discerning buyers. Sunlight floods every room, highlighting the home’s refined details and creating a luminous, welcoming atmosphere. Step inside to find luxurious plank flooring flowing through the entryway, family room, and guest bedrooms, complemented by polished marble in the formal living room and opulent primary suite. The interior showcases meticulous crafts

$1,369,950

4 beds3 baths3,474 sq ft

952 Moss Ln, Winter Park, FL 32789

Custom cabinetry • Tranquil waterfall • Covered lanai

ABOUT THIS HOME
Winter Park, FL Homes for Sale
Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community for its location and tranquil setting on Lake Killarney. Add to that the brand new air conditioning system (2025), hot water heater (2025) and fresh paint throughout (2025) and you'll see why this unit is for you. Step into the unit through the brand new front door (2025) and you are in the generous living room with dining space. The tidy kitchen with matching all white appliances is clean as a whistle. You'll love the large utility is where you'll find the air conditioner, hot water heater and plenty of shelving. The bathroom has new vanity (2025), mirror and light fixture (2025), and newer toilet. Yo

$145,000

1 bed1 bath645 sq ft

2500 Lee Rd #243, Winter Park, FL 32789

Tidy kitchen • Fresh paint • Brand new front door

ABOUT THIS HOME
Winter Park, FL Homes for Sale
Welcome to Killarney Bay—Winter Park’s best-kept secret for tranquil lakeside living, and just steps from the city’s finest shopping and dining! This beautifully updated and spacious 2-bedroom, 2.5-bath townhome-style condo offers a rare blend of modern upgrades and classic charm. Enjoy a BRAND NEW WATER HEATER, vaulted ceilings, a wood-burning fireplace, and rich wood-like flooring throughout. The open-concept kitchen is a showstopper, featuring quartz countertops and stainless steel appliances. Upstairs, you'll find two oversized bedrooms—each with their own walk-in closet and en-suite bathroom. Additional highlights include a private second-floor balcony, inside

$399,000

2 beds2.5 baths1,536 sq ft

240 Killarney Bay Ct #4, Winter Park, FL 32789

Quartz countertops • Open concept kitchen • Modern upgrades

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ABOUT THIS HOME
Winter Park, FL Homes for Sale
WINTER PARK FIVE BEDROOM POOL HOME - Discover luxurious living in the heart of Winter Park! Crafted with exquisite attention to detail, this 5-bedroom, 4.5-bathroom pool residence showcases absolute perfection and modern elegance. Built in 2018 by David Weekley Homes, the property boasts a captivating stone façade and a private backyard oasis featuring a saltwater, heated pool and spa with water feature, and ambient lighting — an entertainer’s dream. Inside, soaring ceilings, gleaming wood floors, expansive picture windows, and an abundance of natural light create an inviting and sophisticated atmosphere. The gourmet kitchen is a chef’s paradise, with white maple ca

$1,770,000

5 beds4.5 baths3,533 sq ft

617 Worthington Dr, Winter Park, FL 32789

Gourmet kitchen • Wrap-around porch • 0.23 acre lot

Property at 1820 Glencoe Rd, Winter Park, FL 32789, 5 beds, 6 baths

$3,825,000

5 beds6 baths4,055 sq ft

1820 Glencoe Rd, Winter Park, FL 32789

Property at 1018 Turner Rd, Winter Park, FL 32789, 3 beds, 2 baths

$835,000

3 beds2 baths2,237 sq ft

1018 Turner Rd, Winter Park, FL 32789

Property at 446 Alberta Dr, Winter Park, FL 32789, 4 beds, 2.5 baths

$1,750,000

4 beds2.5 baths3,263 sq ft

446 Alberta Dr, Winter Park, FL 32789

Property at 1807 Magnolia Ave, Winter Park, FL 32789, 5 beds, 3 baths

$1,201,000

5 beds3 baths2,618 sq ft

1807 Magnolia Ave, Winter Park, FL 32789

Property at 1761 Legion Dr, Winter Park, FL 32789, 5 beds, 5.5 baths

$3,399,999

5 beds5.5 baths4,955 sq ft

1761 Legion Dr, Winter Park, FL 32789

Property at 2922 Reef Knot Pl, Winter Park, FL 32792, 4 beds, 3.5 baths

$1,295,000

4 beds3.5 baths3,153 sq ft

2922 Reef Knot Pl, Winter Park, FL 32792

Property at 3057 Aaron Burr Ave #2, Winter Park, FL 32792, 2 beds, 2 baths

$127,000

2 beds2 baths1,066 sq ft

3057 Aaron Burr Ave #2, Winter Park, FL 32792

Property at 151 N Orlando Ave #212, Winter Park, FL 32789, 3 beds, 2 baths

$570,000

3 beds2 baths1,875 sq ft

151 N Orlando Ave #212, Winter Park, FL 32789

Property at 225 Lewfield Cir #225, Winter Park, FL 32792, 2 beds, 2 baths

$200,000

2 beds2 baths953 sq ft

225 Lewfield Cir #225, Winter Park, FL 32792

Property at 1112 Preserve Point Dr, Winter Park, FL 32789, 5 beds, 6 baths

$8,500,000

5 beds6 baths6,502 sq ft

1112 Preserve Point Dr, Winter Park, FL 32789

Property at 2417 Passamonte Dr Unit 1E, Winter Park, FL 32792, 3 beds, 2.5 baths

$329,999

3 beds2.5 baths1,837 sq ft

2417 Passamonte Dr Unit 1E, Winter Park, FL 32792

Property at 151 N Orlando Ave #118, Winter Park, FL 32789, 2 beds, 1 bath

$299,999

2 beds1 bath710 sq ft

151 N Orlando Ave #118, Winter Park, FL 32789

Property at 1742 Willa Cir, Winter Park, FL 32792, 4 beds, 2 baths

$470,000

4 beds2 baths2,313 sq ft

1742 Willa Cir, Winter Park, FL 32792

Property at 3054 Bluebrook Dr, Winter Park, FL 32792, 3 beds, 2 baths

$469,900

3 beds2 baths1,939 sq ft

3054 Bluebrook Dr, Winter Park, FL 32792

Property at 5338 Tangerine Ave, Winter Park, FL 32792, 4 beds, 2 baths

$459,900

4 beds2 baths2,195 sq ft

5338 Tangerine Ave, Winter Park, FL 32792

Property at 151 N Orlando Ave #204, Winter Park, FL 32789, 2 beds, 1 bath

$229,000

2 beds1 bath710 sq ft

151 N Orlando Ave #204, Winter Park, FL 32789

Property at 913 Moss Ln, Winter Park, FL 32789, 3 beds, 2 baths

$975,000

3 beds2 baths1,887 sq ft

913 Moss Ln, Winter Park, FL 32789

Property at 296 Lewfield Cir, Winter Park, FL 32792, 1 bed, 1 bath

$157,000

1 bed1 bath678 sq ft

296 Lewfield Cir, Winter Park, FL 32792

Property at 2614 Parkland Dr, Winter Park, FL 32789, 4 beds, 3.5 baths

$1,973,200

4 beds3.5 baths3,307 sq ft

2614 Parkland Dr, Winter Park, FL 32789

Property at 1399 Aloma Ave, Winter Park, FL 32789, 3 beds, 2 baths

$665,000

3 beds2 baths1,804 sq ft

1399 Aloma Ave, Winter Park, FL 32789

Property at 1903 S Lakemont Ave, Winter Park, FL 32792, 6 beds, 6 baths

$1,999,999

6 beds6 baths4,056 sq ft

1903 S Lakemont Ave, Winter Park, FL 32792

(305) 854-6247

Property at 1695 Lee Rd Unit E215, Winter Park, FL 32789, 3 beds, 2 baths

$160,000

3 beds2 baths1,149 sq ft

1695 Lee Rd Unit E215, Winter Park, FL 32789

Property at 3254 Oak Lake Pl #137, Winter Park, FL 32792, 2 beds, 2.5 baths

$214,900

2 beds2.5 baths1,031 sq ft

3254 Oak Lake Pl #137, Winter Park, FL 32792

Property at 1910 Glencoe Rd, Winter Park, FL 32789, 4 beds, 5 baths

$3,490,000

4 beds5 baths4,205 sq ft

1910 Glencoe Rd, Winter Park, FL 32789

Property at 1400 Alabama Dr, Winter Park, FL 32789, 5 beds, 7 baths

$5,895,000

5 beds7 baths7,916 sq ft

1400 Alabama Dr, Winter Park, FL 32789

Property at 2500 Lee Rd #208, Winter Park, FL 32789, 2 beds, 2 baths

$195,000

2 beds2 baths956 sq ft

2500 Lee Rd #208, Winter Park, FL 32789

Property at 701 Denton Rd, Winter Park, FL 32792, 3 beds, 2 baths

$565,000

3 beds2 baths2,268 sq ft

701 Denton Rd, Winter Park, FL 32792

Property at 1564 Cavendish Rd, Winter Park, FL 32789, 3 beds, 1 bath

$450,000

3 beds1 bath1,140 sq ft

1564 Cavendish Rd, Winter Park, FL 32789

Property at 101 S Interlachen Ave #104, Winter Park, FL 32789, 2 beds, 2 baths

$635,000

2 beds2 baths949 sq ft

101 S Interlachen Ave #104, Winter Park, FL 32789

Property at 1360 Formosa Ave, Winter Park, FL 32789, 3 beds, 3 baths

$625,000

3 beds3 baths1,890 sq ft

1360 Formosa Ave, Winter Park, FL 32789

Property at 1444 Pelican Bay Trl, Winter Park, FL 32792, 4 beds, 2.5 baths

$999,950

4 beds2.5 baths3,121 sq ft

1444 Pelican Bay Trl, Winter Park, FL 32792

Property at 1901 Lake Sue Dr, Orlando, FL 32803, 3 beds, 3 baths

$1,097,000

3 beds3 baths2,460 sq ft

1901 Lake Sue Dr, Orlando, FL 32803

Property at 607 Dunblane Dr, Winter Park, FL 32792, 4 beds, 2.5 baths

$675,000

4 beds2.5 baths2,046 sq ft

607 Dunblane Dr, Winter Park, FL 32792

Property at 5325 Cypress Reserve Pl, Winter Park, FL 32792, 5 beds, 3.5 baths

$918,000

5 beds3.5 baths3,598 sq ft

5325 Cypress Reserve Pl, Winter Park, FL 32792

Property at 250 Cortland Ave, Winter Park, FL 32789, 3 beds, 2 baths

$950,000

3 beds2 baths2,114 sq ft

250 Cortland Ave, Winter Park, FL 32789

Property at 3071 George Mason Ave #5, Winter Park, FL 32792, 1 bath

$89,900

0 beds1 bath549 sq ft

3071 George Mason Ave #5, 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%

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