274 Results

View 274 Winter Park Florida Homes for Sale

Pended $459,995

Reduced By $10,000

White single-story home with brown roof and garage at 1005 Carvell Dr, Winter Park, FL 32792
View Details 45 Photos
Single-story house with palm tree and well-maintained lawn at 1005 Carvell Dr, Winter Park, FL 32792
Ranch style home with lush green lawn and blue sky at 1005 Carvell Dr, Winter Park, FL 32792
One-story house with a large yard and shed at 1005 Carvell Dr, Winter Park, FL 32792
On Market For 98 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1932

  • Year Built

    1971

  • $/SqFt

    $238

Don’t miss your opportunity to own this incredible home; schedule a showing today and make your dream of Winter Park living a reality! EXP REALTY LLC.

Home For Sale $439,500

Reduced By $25,500

Charming single-story home featuring a well-maintained lawn, mature landscaping, and a long private driveway at 2158 Sussex Rd, Winter Park, FL 32792
View Details 17 Photos
Spacious living room with hardwood floors and large windows at 2158 Sussex Rd, Winter Park, FL 32792
Laundry room with tile floors, shelving, and hookups at 2158 Sussex Rd, Winter Park, FL 32792
Modern kitchen with granite countertops and stainless steel appliances at 2158 Sussex Rd, Winter Park, FL 32792
On Market For 104 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1669

  • Year Built

    1973

  • $/SqFt

    $263

Winter Woods - Convenient to 426/Aloma, 417, 50/Colonial, Park Ave., airport, shopping and restaurants. MUST SEE! KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $4,985,000

Modern two-story home with white exterior, gray accents, and a paved driveway at 2161 Sharon Rd, Winter Park, FL 32789
View Details 90 Photos
Luxury home with gray and white exterior, landscaping, and a spacious driveway at 2161 Sharon Rd, Winter Park, FL 32789
Stunning two-story home, white exterior, lush landscaping, and a large driveway at 2161 Sharon Rd, Winter Park, FL 32789
Modern home with white exterior, gray accents, and a two-car garage at 2161 Sharon Rd, Winter Park, FL 32789
On Market For 105 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6338

  • Year Built

    2023

  • $/SqFt

    $787

Tuscania - Get one step closer to owning the realization of your dream dwelling experience! LA ROSA REALTY HORIZONS LLC.

Home For Sale $1,150,000

Brick ranch home with blue accents and a pink door, landscaped lawn and walkway at 708 Balmoral Rd, Winter Park, FL 32789
View Details 45 Photos
Ranch style home with a walkway leading to the entrance. Features brick exterior and blue accents at 708 Balmoral Rd, Winter Park, FL 32789
Front entrance with pink door and brick steps, blue siding, and landscaping at 708 Balmoral Rd, Winter Park, FL 32789
Bright entryway with tiled floor, a small table, and a view to the hardwood living area at 708 Balmoral Rd, Winter Park, FL 32789
On Market For 108 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2786

  • Year Built

    1960

  • $/SqFt

    $413

Kenilworth Shores - This fantastic location provides easy access to shopping, dining, and the popular Park Avenue with its boutique shopping and great restaurants. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $530,000

Reduced By $32,000

House exterior featuring a light-grey facade, white garage door, and a well-maintained lawn at 4026 Tenita Dr, Winter Park, FL 32792
View Details 33 Photos
Spacious living room with a stone fireplace, tiled floors, and comfortable seating at 4026 Tenita Dr, Winter Park, FL 32792
Living room with a stone fireplace and brown tiled floors at 4026 Tenita Dr, Winter Park, FL 32792
Bright bedroom with large bed, modern nightstands, and ample closet space at 4026 Tenita Dr, Winter Park, FL 32792
On Market For 110 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2122

  • Year Built

    1979

  • $/SqFt

    $250

Lake Waunatta Woods - Don't miss out on this exceptional property. OPENDOOR BROKERAGE LLC.

Pended $399,900

Reduced By $10,000

Newly renovated house with gray exterior, covered porch, and well-manicured lawn at 3607 Datura Ct, Winter Park, FL 32792
View Details 66 Photos
Aerial view showcasing the house's position on a corner lot near a waterway at 3607 Datura Ct, Winter Park, FL 32792
Aerial view showing home's location near water, neighborhood context, and surrounding houses at 3607 Datura Ct, Winter Park, FL 32792
Gray house with a covered porch, freshly mulched landscaping, and a neatly kept lawn at 3607 Datura Ct, Winter Park, FL 32792
On Market For 111 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1600

  • Year Built

    1962

  • $/SqFt

    $250

Eastbrook - Ready for immediate move in. Schedule your showing today! PREMIUM PROPERTIES R.E SERVICE.

Home For Sale $424,900

Reduced By $40,100

Newly renovated home with gray siding, blue door, and red mulch at 1566 Lawndale Cir, Winter Park, FL 32792
View Details 39 Photos
Gray house with blue garage door and red mulch at 1566 Lawndale Cir, Winter Park, FL 32792
House entrance with blue door and red mulch landscaping at 1566 Lawndale Cir, Winter Park, FL 32792
Blue front door with white sidelight and black hardware at 1566 Lawndale Cir, Winter Park, FL 32792
On Market For 112 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1592

  • Year Built

    1985

  • $/SqFt

    $267

Country Lane - Lovely walkable neighborhood with playground, tennis courts and lakefront dock for fishing. TERZA REAL ESTATE.

Home For Sale $2,949,999

Reduced By $50,000

Relaxing deck overlooking lake with fire pit and seating at 2652 Lake Howell Ln, Winter Park, FL 32792
View Details 38 Photos
Aerial view of waterfront property with lush landscaping at 2652 Lake Howell Ln, Winter Park, FL 32792
Two-car garage and boat parking at 2652 Lake Howell Ln, Winter Park, FL 32792
Elegant front entry with columns and brick steps at 2652 Lake Howell Ln, Winter Park, FL 32792
On Market For 115 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3898

  • Year Built

    1954

  • $/SqFt

    $757

Whether you're looking for a vacation getaway or a forever home, this is a rare opportunity you won't want to miss. Schedule your private showing today! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $749,000

Reduced By $50,000

Charming yellow bungalow with screened porch, mature trees, and a landscaped yard at 786 Antonette Ave, Winter Park, FL 32789
View Details 31 Photos
Aerial view showing home's location in a vibrant, tree-lined neighborhood near the water at 786 Antonette Ave, Winter Park, FL 32789
Spacious backyard with lush grass, tropical plants, and a fire pit area at 786 Antonette Ave, Winter Park, FL 32789
Inviting front porch with blue door, wicker furniture, and a tranquil atmosphere at 786 Antonette Ave, Winter Park, FL 32789
On Market For 117 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1146

  • Year Built

    1925

  • $/SqFt

    $654

College Place - Sure to attract a lot of attention (as homes in this area don’t come up for sale often) seize the opportunity to make it your own! RE/MAX 200 REALTY.

Home For Sale $8,799,000

Reduced By $2,200,999

Modern home with sleek design, light color, and a landscaped lawn at 2661 Via Tuscany, Winter Park, FL 32789
View Details 100 Photos
Grand foyer with wood door, cowhide rug, and view into the living room with high ceilings and natural light at 2661 Via Tuscany, Winter Park, FL 32789
Bright living room with modern decor, floor-to-ceiling windows, and an open layout for seamless entertaining at 2661 Via Tuscany, Winter Park, FL 32789
Modern kitchen featuring an island with seating, sleek cabinetry, and high-end stainless steel appliances at 2661 Via Tuscany, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 118 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4564

  • Year Built

    2024

  • $/SqFt

    $1,928

Experience the pinnacle of luxury living—schedule a private tour today. PV LUXURY GROUP PA.

Home For Sale $1,395,000

Reduced By $55,000

Two-story farmhouse style home with white siding, landscaping, and a two-car garage at dusk at 777 Halifax Ave, Winter Park, FL 32792
View Details 49 Photos
Bright, open kitchen with island and modern appliances flows into a living area with soaring ceilings at 777 Halifax Ave, Winter Park, FL 32792
Bright living room features high ceilings and large windows overlooking the backyard at 777 Halifax Ave, Winter Park, FL 32792
A spacious main bedroom features tray ceilings and large windows at 777 Halifax Ave, Winter Park, FL 32792
On Market For 123 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3161

  • Year Built

    2021

  • $/SqFt

    $441

Don’t miss the opportunity to make this exceptional home yours—schedule a private showing today! EXP REALTY LLC.

Home For Sale $405,000

Reduced By $35,000

Ranch-style home with a two-car garage and a spacious driveway at 3076 Crane Strand Dr, Winter Park, FL 32792
View Details 36 Photos
Newly renovated home with a large front yard and mature trees at 3076 Crane Strand Dr, Winter Park, FL 32792
Charming neighborhood street view with mature trees and well-maintained lawns creates a welcoming atmosphere at 3076 Crane Strand Dr, Winter Park, FL 32792
A quaint single-Gathering home with a well-kept lawn and a two-car garage at 3076 Crane Strand Dr, Winter Park, FL 32792
On Market For 123 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1200

  • Year Built

    1972

  • $/SqFt

    $338

Laurel Springs - Don’t miss this incredible opportunity to enjoy all the perks of Winter Park living in a tranquil and welcoming community. KELLER WILLIAMS LEGACY REALTY.

Home For Sale $2,999,900

Reduced By $299,100

Beautiful two-story home with a lush green lawn at 2550 Venetian Way, Winter Park, FL 32789
View Details 41 Photos
Elegant entryway with high ceilings and wood door at 2550 Venetian Way, Winter Park, FL 32789
Stunning entryway with a unique architectural design at 2550 Venetian Way, Winter Park, FL 32789
Dramatic entryway with a circular staircase and high ceilings at 2550 Venetian Way, Winter Park, FL 32789
On Market For 125 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4875

  • Year Built

    2008

  • $/SqFt

    $615

Maitland Shores - Relaxation and a renewed sense of self await! COMPASS FLORIDA LLC.

Home For Sale $1,649,000

Reduced By $50,000

Modern two-story house with stone accents at 1429 Chapman Cir, Winter Park, FL 32789
View Details 36 Photos
Elegant entryway with blue doors and stone pillars at 1429 Chapman Cir, Winter Park, FL 32789
Open living area with stone wall and backyard access at 1429 Chapman Cir, Winter Park, FL 32789
Bright living room with white sofas and large windows at 1429 Chapman Cir, Winter Park, FL 32789
On Market For 128 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3116

  • Year Built

    2014

  • $/SqFt

    $529

This masterfully designed residence offers the perfect balance of sophisticated style, modern convenience, and prime location. CORCORAN PREMIER REALTY.

Home For Sale $1,299,000

Two-story Mediterranean home with tile roof and attached garage at 7440 Aloma Ave, Winter Park, FL 32792
View Details 39 Photos
Luxury two-story home with tile roof and large driveway at 7440 Aloma Ave, Winter Park, FL 32792
Grand living room with ornate furnishings and a sweeping staircase at 7440 Aloma Ave, Winter Park, FL 32792
Elegant living room showcasing a dramatic staircase and high ceilings at 7440 Aloma Ave, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 129 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4435

  • Year Built

    1950

  • $/SqFt

    $293

The possibilities are endless—don’t miss out on this incredible opportunity! MARZUCCO REAL ESTATE.

Home For Sale $815,000

Reduced By $20,000

Two-story house with three-car garage, landscaped yard, and stone accents at 1316 Fountain Hills Ct, Winter Park, FL 32792
View Details 33 Photos
Inviting front entrance with stone columns and a charming welcome sign at 1316 Fountain Hills Ct, Winter Park, FL 32792
Relaxing backyard oasis featuring a refreshing pool and fire pit at 1316 Fountain Hills Ct, Winter Park, FL 32792
Bright and airy entryway with staircase, built-in storage and tile flooring at 1316 Fountain Hills Ct, Winter Park, FL 32792
On Market For 128 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2823

  • Year Built

    2018

  • $/SqFt

    $289

This home is a one of a kind find in Winter Park with its location close to Winter Springs Oviedo, UCF, Orlando downtown, Winter Park shopping, the airport, 417 & major roadways. Schedule a Showing Today! EMPIRE NETWORK REALTY.

Home For Sale $579,900

Reduced By $75,000

Brick ranch house with a two-car garage, landscaping, and a long driveway at 2518 Sweetwater Trl, Winter Park, FL 32789
View Details 41 Photos
Brick ranch home with a two-car garage and a curved driveway at 2518 Sweetwater Trl, Winter Park, FL 32789
Ranch style brick home with a two-car garage and landscaped lawn at 2518 Sweetwater Trl, Winter Park, FL 32789
Brick ranch house with a two-car garage and lush green lawn at 2518 Sweetwater Trl, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 131 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2205

  • Year Built

    1965

  • $/SqFt

    $263

Do not miss out on the perfect blend of style, comfort, and location! BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY.

Home For Sale $500,000

Reduced By $75,000

Charming two-story home with a well-manicured lawn and an American flag waving in the breeze at 5240 N Lake Burkett Ln, Winter Park, FL 32792
View Details 73 Photos
Detailed floorplan showcasing the layout of the home's two floors with room dimensions and major features at 5240 N Lake Burkett Ln, Winter Park, FL 32792
Charming two-story home featuring a well-manicured lawn and a classic design with a two-car garage at 5240 N Lake Burkett Ln, Winter Park, FL 32792
Inviting front yard with lush green grass and a well-maintained exterior featuring a charming entryway and manicured landscaping at 5240 N Lake Burkett Ln, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 92 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2290

  • Year Built

    1987

  • $/SqFt

    $218

Come see all this amazing home has to offer. COLDWELL BANKER REALTY.

Home For Sale $474,900

Reduced By $24,100

Ranch style home with blue exterior and a spacious lawn at 2341 Devon Ct, Winter Park, FL 32789
View Details 27 Photos
Bright living room featuring light wood floors and a ceiling fan at 2341 Devon Ct, Winter Park, FL 32789
Spacious living room with light wood floors, open to kitchen at 2341 Devon Ct, Winter Park, FL 32789
Open concept living room with hardwood floors and a view to kitchen at 2341 Devon Ct, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 132 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1773

  • Year Built

    1953

  • $/SqFt

    $268

Glencoe - Schedule your appointment today to preview this Winter Park jem! UNITED REAL ESTATE PREFERRED.

Home For Sale $4,100,000

Two-story modern home with a black roof and landscaped yard at 1751 Glencoe Rd, Winter Park, FL 32789
View Details 18 Photos
Two-story modern home with a black roof and paver driveway at 1751 Glencoe Rd, Winter Park, FL 32789
Modern two story home with a large pool and deck at 1751 Glencoe Rd, Winter Park, FL 32789
Spacious living room with a fireplace and built-in shelving at 1751 Glencoe Rd, Winter Park, FL 32789
On Market For 136 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4520

  • Year Built

    2025

  • $/SqFt

    $907

Experience the epitome of refined living at 1751 Glencoe Road, where every detail has been crafted to perfection. COMPASS FLORIDA LLC.

Pended $2,650,000

Reduced By $150,000

Stunning two-story home with brick pathway, lush landscaping, and a Mediterranean-style design at 1010 N Pennsylvania Ave, Winter Park, FL 32789
View Details 88 Photos
Beautiful home at night with a gated entry and walkway leading to the front door at 1010 N Pennsylvania Ave, Winter Park, FL 32789
Elegant home entrance featuring a brick walkway and ornate double doors at 1010 N Pennsylvania Ave, Winter Park, FL 32789
Bright and spacious entryway with tile floors, double doors, and decorative accents at 1010 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 134 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4074

  • Year Built

    2017

  • $/SqFt

    $650

Feel free to request an upgrades and features sheet outlining all the wonderful aspects of this home! BHHS FLORIDA REALTY.

Home For Sale $432,000

Reduced By $16,800

Mid-century modern home with a paved driveway and lush landscaping at 627 Carvell Dr, Winter Park, FL 32792
View Details 21 Photos
Beautiful mid-century modern home with a well-manicured lawn at 627 Carvell Dr, Winter Park, FL 32792
Bright living room featuring light flooring and a sliding barn door at 627 Carvell Dr, Winter Park, FL 32792
Bright and airy living room with a barn door and hardwood floors at 627 Carvell Dr, Winter Park, FL 32792
On Market For 112 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1346

  • Year Built

    1957

  • $/SqFt

    $321

Winter Park Estates - Don’t miss the opportunity to make this exceptional property your own! NO HOA! EXP REALTY LLC.

Home For Sale $439,000

Reduced By $10,000

Two-story house with gray siding and landscaped lawn at 1820 Blaine Ter, Winter Park, FL 32792
View Details 51 Photos
Two-story house with gray siding and attached garage at 1820 Blaine Ter, Winter Park, FL 32792
Two-story house with gray siding, a two-car garage, and a well-manicured lawn at 1820 Blaine Ter, Winter Park, FL 32792
Two-story house with gray siding, a two-car garage, and a landscaped front yard at 1820 Blaine Ter, Winter Park, FL 32792
On Market For 139 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1725

  • Year Built

    1990

  • $/SqFt

    $254

Don't miss your chance to make this exceptional house your home! LPT REALTY.

Home For Sale $829,000

Reduced By $140,000

Charming single story home with a modern white exterior and landscaped lawn at 1795 Walker Ave, Winter Park, FL 32789
View Details 31 Photos
Modern kitchen with white cabinets, quartz countertops, and gold accents at 1795 Walker Ave, Winter Park, FL 32789
Bright dining room with wood table and mustard yellow chairs at 1795 Walker Ave, Winter Park, FL 32789
Modern kitchen with a breakfast bar, white cabinets and gold fixtures at 1795 Walker Ave, Winter Park, FL 32789
On Market For 140 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    1813

  • Year Built

    1958

  • $/SqFt

    $457

Osceola Heights - Don't miss out on this opportunity—act quickly! ALIGN REAL ESTATE LLC.

Home For Sale $699,000

Reduced By $50,999

Aerial view of a home with a pool, solar panels, and well-maintained landscaping at 3136 Heartleaf Pl, Winter Park, FL 32792
View Details 33 Photos
Freeform swimming pool with a screened enclosure at 3136 Heartleaf Pl, Winter Park, FL 32792
Relaxing living room with large TV and hardwood floors at 3136 Heartleaf Pl, Winter Park, FL 32792
Well maintained green two story home with landscaped front yard and matching green driveway at 3136 Heartleaf Pl, Winter Park, FL 32792
On Market For 144 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2717

  • Year Built

    1995

  • $/SqFt

    $257

Lost Creek - Situated on almost a quarter-acre corner lot in a beautiful, well-cared-for neighborhood with Seminole County Schools, this well-maintained home offers easy access to 417, is less than 20 minutes from the famous Park Avenue with some of the best shops and restaurants in the city, and 25 minutes from the airport. Schedule your showing today! ALL REAL ESTATE & INVESTMENTS.

Home For Sale $995,000

Modern home with large deck, wood siding, and expansive windows at 870 Carver St, Winter Park, FL 32789
View Details 6 Photos
Contemporary two-story house with a sleek design and wood accents at 870 Carver St, Winter Park, FL 32789
Contemporary design with wood accents, stone walkway, and lush landscaping at 870 Carver St, Winter Park, FL 32789
Modern home with a large deck, and open floor plan visible through large window at 870 Carver St, Winter Park, FL 32789
On Market For 145 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1844

  • Year Built

    1954

  • $/SqFt

    $540

Don’t miss the chance to partner with a premier builder to create a home that meets your unique needs. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,350,000

Reduced By $100,000

Lakefront property with a dock and gazebo at 632 Country Club Dr, Winter Park, FL 32789
View Details 38 Photos
Ranch-style house with a landscaped yard at 632 Country Club Dr, Winter Park, FL 32789
Aerial view of a waterfront home with a lake view and city skyline in the background at 632 Country Club Dr, Winter Park, FL 32789
Lakefront property with a large wooden dock and gazebo at 632 Country Club Dr, Winter Park, FL 32789
On Market For 149 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2342

  • Year Built

    1952

  • $/SqFt

    $576

632 Country Club is approximately 1.5 miles from luxurious Park Avenue and 5 miles from downtown Orlando. KELLER WILLIAMS ADVANTAGE REALTY.

Pended $3,250,000

Reduced By $325,000

Two-story home with circular driveway at 1900 W Fawsett Rd, Winter Park, FL 32789
View Details 93 Photos
Aerial of waterfront home with boat dock at 1900 W Fawsett Rd, Winter Park, FL 32789
Aerial of waterfront property with boathouse at 1900 W Fawsett Rd, Winter Park, FL 32789
Aerial view of waterfront homes and boat docks at 1900 W Fawsett Rd, Winter Park, FL 32789
On Market For 147 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4600

  • Year Built

    1969

  • $/SqFt

    $707

Don’t miss the opportunity to make this stunning lakefront home your own! KELLY PRICE & COMPANY LLC.

Pended $1,275,000

Reduced By $120,000

Ranch style home with light grey exterior, double garage and paver driveway at 1681 Blue Ridge Rd, Winter Park, FL 32789
View Details 52 Photos
Light grey home with double garage and paver driveway at 1681 Blue Ridge Rd, Winter Park, FL 32789
Updated ranch home with paver driveway and lush landscaping at 1681 Blue Ridge Rd, Winter Park, FL 32789
Double garage with paver driveway and landscaping at 1681 Blue Ridge Rd, Winter Park, FL 32789
On Market For 150 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2762

  • Year Built

    1960

  • $/SqFt

    $462

You don’t want to miss this one! CENTRAL FLORIDA PRIME REAL ESTATE LLC.

Home For Sale $399,900

Two-car garage and pink exterior at 5418 S Bracken Ct, Winter Park, FL 32792
View Details 35 Photos
Kidney shaped swimming pool in backyard at 5418 S Bracken Ct, Winter Park, FL 32792
Living room with comfy seating and large TV at 5418 S Bracken Ct, Winter Park, FL 32792
Spacious living room with tile floors, ceiling fan, and sliding glass doors leading to a pool at 5418 S Bracken Ct, Winter Park, FL 32792
On Market For 151 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1301

  • Year Built

    1991

  • $/SqFt

    $307

Bridgewater - Schedule your showing today and submit your offers—don’t miss out on this beautiful home! EXP REALTY LLC.

Home For Sale $875,555

Reduced By $13,333

Mid-century modern home with a large front yard at 2128 Sycamore Dr, Winter Park, FL 32789
View Details 11 Photos
Mid-century modern home with white exterior, black accents, and a spacious lawn at 2128 Sycamore Dr, Winter Park, FL 32789
Mid-century modern home with white exterior, black accents, and a spacious lawn at 2128 Sycamore Dr, Winter Park, FL 32789
White mid-century modern home with a large backyard at 2128 Sycamore Dr, Winter Park, FL 32789
On Market For 153 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1760

  • Year Built

    1953

  • $/SqFt

    $497

Northwood Terrace - Act fast—opportunities like this don’t last long! EXP REALTY LLC.

Home For Sale $525,000

Reduced By $50,000

Mid-Century Ranch style home with mature trees and driveway at 2821 Chantilly Ave, Winter Park, FL 32789
View Details 18 Photos
Aerial view showing home's location near a pond at 2821 Chantilly Ave, Winter Park, FL 32789
Detailed survey map of the property and surrounding area at 2821 Chantilly Ave, Winter Park, FL 32789
Bright dining area with hardwood floors and kitchen view at 2821 Chantilly Ave, Winter Park, FL 32789
On Market For 155 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1440

  • Year Built

    1959

  • $/SqFt

    $365

Winter Park Manor - Extras include: updated electric panel, 2017 AC, updated plumbing & 24x12 backyard shed. WELCOME HOME! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $5,400,000

Two story home with lush landscaping and a circular driveway at 2228 Azalea Pl, Winter Park, FL 32789
View Details 34 Photos
Elegant home entrance with a pink door, arched entryway, and potted plants at 2228 Azalea Pl, Winter Park, FL 32789
House exterior showcasing a classic design with a green lawn at 2228 Azalea Pl, Winter Park, FL 32789
Vibrant living room with bold colors, unique artwork, and comfortable seating at 2228 Azalea Pl, Winter Park, FL 32789
On Market For 157 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5072

  • Year Built

    2008

  • $/SqFt

    $1,065

Maitland Shores - The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. COMPASS FLORIDA LLC.

Home For Sale $2,374,000

Reduced By $25,000

Modern home with pool and landscaped yard, offering an open floor plan and sleek design at 2522 Lafayette Ave, Winter Park, FL 32789
View Details 55 Photos
Contemporary home with gray and white exterior, showcasing a stylish and modern design at 2522 Lafayette Ave, Winter Park, FL 32789
Modern two-story home with a rooftop deck and attached garage, offering city views at 2522 Lafayette Ave, Winter Park, FL 32789
Stylish home with large windows and a modern facade, creating a welcoming curb appeal at 2522 Lafayette Ave, Winter Park, FL 32789
On Market For 157 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3399

  • Year Built

    2022

  • $/SqFt

    $698

Truly photos and words do not begin to describe this Architectural Brilliance, come out and explore this gem where you will be greeted by Astro the Robot. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $338,000

Reduced By $7,000

Charming light blue bungalow with a covered porch at 5080 Seminole Ave, Winter Park, FL 32792
View Details 35 Photos
Spacious backyard with lush green grass at 5080 Seminole Ave, Winter Park, FL 32792
Large backyard perfect for outdoor activities at 5080 Seminole Ave, Winter Park, FL 32792
Spacious backyard with a long driveway at 5080 Seminole Ave, Winter Park, FL 32792
On Market For 116 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1078

  • Year Built

    1924

  • $/SqFt

    $314

Don’t miss out on this fantastic home in a highly desirable area! SERHANT.

Home For Sale $435,000

Cute yellow house with a carport and well-maintained lawn at 920 Gloriosa Ave, Winter Park, FL 32789
View Details 15 Photos
House exterior showcasing a lush garden and inviting front entrance at 920 Gloriosa Ave, Winter Park, FL 32789
Living Room with white sectional sofa and area rug at 920 Gloriosa Ave, Winter Park, FL 32789
Dining room with a table, chairs, and built-in shelving at 920 Gloriosa Ave, Winter Park, FL 32789
On Market For 165 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1540

  • Year Built

    1956

  • $/SqFt

    $282

Come take a look before it's gone! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $3,892,000

Elegant two-story brick home with a landscaped yard at 1391 Richmond Rd, Winter Park, FL 32789
View Details 66 Photos
Grand two-story brick home with a circular driveway at 1391 Richmond Rd, Winter Park, FL 32789
Brick home nestled in lush landscaping, large driveway at 1391 Richmond Rd, Winter Park, FL 32789
Mature trees and landscaped gardens surround the home at 1391 Richmond Rd, Winter Park, FL 32789
On Market For 168 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    4635

  • Year Built

    2001

  • $/SqFt

    $840

Virginia Heights - Celebrate nature’s wildlife which range from owls, great white egrets, blue herons, hawks, bunnies, and otters in your private sanctuary minutes to Winter Park’s premier dining, upscale shopping, Mead Botanical Garden, and the highly coveted Audubon K-8, and Winter Park High! STOCKWORTH REALTY GROUP.

Pended $5,695,000

Modern two-story home with landscaped lawn and walkway at 210 Chelton Cir, Winter Park, FL 32789
View Details 97 Photos
Landscaped entry with walkway to modern home at 210 Chelton Cir, Winter Park, FL 32789
Modern home with attached garage and manicured lawn at 210 Chelton Cir, Winter Park, FL 32789
Stunning modern home at sunset with landscaped yard at 210 Chelton Cir, Winter Park, FL 32789
On Market For 167 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5264

  • Year Built

    2024

  • $/SqFt

    $1,082

Welcome home to one of the most exceptional properties on the market! CORCORAN PREMIER REALTY.

Home For Sale $399,000

Reduced By $13,000

Single story home with a large front yard and driveway at 2140 Ridge Dr, Winter Park, FL 32792
View Details 38 Photos
Single story home with a large front yard and driveway at 2140 Ridge Dr, Winter Park, FL 32792
Single story home with a large front yard and driveway at 2140 Ridge Dr, Winter Park, FL 32792
Single story home with a large front yard and driveway at 2140 Ridge Dr, Winter Park, FL 32792
On Market For 153 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1554

  • Year Built

    1959

  • $/SqFt

    $257

Don’t miss out on the chance to own this fully renovated gem that’s move-in ready and waiting for you to make it your own! REAL BROKER, LLC.

Pended $1,069,000

Reduced By $206,000

Ranch style home with a manicured lawn and lush landscaping at 1001 Tuscany Pl, Winter Park, FL 32789
View Details 23 Photos
White front door with sidelights and a landscaped walkway at 1001 Tuscany Pl, Winter Park, FL 32789
Spacious backyard with a detached garage and lush greenery at 1001 Tuscany Pl, Winter Park, FL 32789
Landscaped side yard with mature trees and lush greenery at 1001 Tuscany Pl, Winter Park, FL 32789
On Market For 172 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2458

  • Year Built

    1978

  • $/SqFt

    $435

Being sold AS IS, please see Realtor Remarks for comments. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,445,000

Reduced By $50,000

Stunning contemporary home with a white exterior, landscaped yard, and brick driveway at 1371 Lyndale Blvd, Winter Park, FL 32789
View Details 65 Photos
Modern home nestled on a tree-lined street with a brick road at 1371 Lyndale Blvd, Winter Park, FL 32789
Top-down view of a home showcasing its layout and landscaped yard at 1371 Lyndale Blvd, Winter Park, FL 32789
Aerial view of a home showcasing the property and surrounding neighborhood at 1371 Lyndale Blvd, Winter Park, FL 32789
On Market For 179 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2739

  • Year Built

    1949

  • $/SqFt

    $528

Dixie Terrace - With every detail thoughtfully curated, this property is more than just a home—it's a lifestyle. COLDWELL BANKER RESIDENTIAL RE.

Pended $1,420,000

Reduced By $230,000

Modern two-story home with attractive landscaping at 840 W Comstock Ave, Winter Park, FL 32789
View Details 39 Photos
Small front porch with modern design and seating at 840 W Comstock Ave, Winter Park, FL 32789
Modern staircase with metal railing and light wood at 840 W Comstock Ave, Winter Park, FL 32789
Modern light wood staircase with black metal railing at 840 W Comstock Ave, Winter Park, FL 32789
On Market For 192 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2350

  • Year Built

    2024

  • $/SqFt

    $604

Schedule your visit today and fall in love with this dreamy home! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $1,999,993

Reduced By $200,006

Two-story house with a double front door and landscaped yard at 1451 Lyndale Blvd, Winter Park, FL 32789
View Details 89 Photos
Home's side view, showcasing garage and landscaping at 1451 Lyndale Blvd, Winter Park, FL 32789
Inviting swimming pool with a spacious patio area at 1451 Lyndale Blvd, Winter Park, FL 32789
Two-story house with a double front door and landscaped yard at 1451 Lyndale Blvd, Winter Park, FL 32789
On Market For 202 Days

  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    3853

  • Year Built

    2012

  • $/SqFt

    $519

Dixie Terrace - Schedule your private showing today and discover what makes this Winter Park home truly exceptional. REALTY ONE GROUP MVP.

Home For Sale $630,000

Reduced By $65,000

Cute bungalow with yellow door, newly paved driveway, and manicured lawn at 1848 Mizell Ave, Winter Park, FL 32789
View Details 29 Photos
Charming home with yellow front door and attached garage at 1848 Mizell Ave, Winter Park, FL 32789
Quaint home with brick facade, lush landscaping, and white fence at 1848 Mizell Ave, Winter Park, FL 32789
Bright living room with hardwood floors and a fireplace at 1848 Mizell Ave, Winter Park, FL 32789
On Market For 208 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1162

  • Year Built

    1953

  • $/SqFt

    $542

Ft. with single car garage 1,754 gross square feet Remodeled kitchen and large backyard Winter Park High School A grade school - Elementary and Middle Schools grade B BLUE LIGHTHOUSE REALTY INC.

Pended $599,000

Reduced By $51,000

Newly renovated brick and stucco ranch home with a well-maintained lawn at 274 N Ranger Blvd, Winter Park, FL 32792
View Details 40 Photos
Open concept living room with modern furniture and a view of the kitchen at 274 N Ranger Blvd, Winter Park, FL 32792
Open concept living room, featuring modern decor and a view into the kitchen at 274 N Ranger Blvd, Winter Park, FL 32792
Living Room with modern furniture, an open floor plan, and natural light at 274 N Ranger Blvd, Winter Park, FL 32792
On Market For 210 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1420

  • Year Built

    1963

  • $/SqFt

    $422

Don’t miss the chance to make this your new home – schedule a tour today! NETWORTH REALTY OF ORLANDO, LLC.

Home For Sale $819,900

Reduced By $19,100

White brick ranch home with landscaped lawn and driveway at 648 Brechin Dr, Winter Park, FL 32792
View Details 58 Photos
House exterior showcasing manicured lawn and driveway at 648 Brechin Dr, Winter Park, FL 32792
Front view of a renovated mid-century modern home at 648 Brechin Dr, Winter Park, FL 32792
Stylish blue front door and white brick facade at 648 Brechin Dr, Winter Park, FL 32792
On Market For 140 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1820

  • Year Built

    1961

  • $/SqFt

    $450

Kenilworth Shores - Transferable Sentracon system.Easy show and a must see! PRICED below appraised value! RAZZANI INTERNATIONAL REALTY.

Home For Sale $3,295,000

Attractive two-story home showcasing modern architectural design, beautiful landscaping and large windows at 1730 Winchester Dr, Winter Park, FL 32789
View Details 22 Photos
Bright and modern kitchen featuring a large center island, stylish pendant lighting, and stainless appliances at 1730 Winchester Dr, Winter Park, FL 32789
Covered patio with a stone fireplace, tile flooring, and wood ceiling, perfect for outdoor entertaining at 1730 Winchester Dr, Winter Park, FL 32789
Elegant foyer featuring a staircase with wood treads, black iron railings, and a view into the dining room at 1730 Winchester Dr, Winter Park, FL 32789
On Market For 212 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4080

  • Year Built

    2024

  • $/SqFt

    $808

Schedule your private tour today to see this stunning property in person! KELLER WILLIAMS WINTER PARK.

Home For Sale $995,000

Reduced By $55,000

Ranch-style home with carport, mature trees, and well-maintained lawn at 2260 Hawick Ln, Winter Park, FL 32792
View Details 6 Photos
Land plat showing property boundaries, setbacks, and buildable areas for multiple lots in a planned development at 2260 Hawick Ln, Winter Park, FL 32792
Charming artist rendering of two homes showcasing unique architectural styles and landscaping at 2260 Hawick Ln, Winter Park, FL 32792
Bird's eye architectural rendering of a 4-unit property floor plan, including gardens and parking spaces at 2260 Hawick Ln, Winter Park, FL 32792
On Market For 216 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1374

  • Year Built

    1971

  • $/SqFt

    $724

(150ft street frontage by 140ft lot depth). DAVEN REAL ESTATE INC.

Home For Sale $799,900

Reduced By $150,100

Charming house with a spacious front yard and mature trees at 731 Midget Dr, Winter Park, FL 32789
View Details 19 Photos
Tan house with a garage and driveway at 731 Midget Dr, Winter Park, FL 32789
Aerial view showing a home's location on Midget Dr at 731 Midget Dr, Winter Park, FL 32789
Home with a brick driveway and lush landscaping at 731 Midget Dr, Winter Park, FL 32789
On Market For 219 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    960

  • Year Built

    1941

  • $/SqFt

    $833

Don’t miss this diamond in the rough – call today for your showing!! ! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $1,795,000

Aerial view of a waterfront home with a private dock, lush landscaping, and a brick driveway at 279 Rippling Ln, Winter Park, FL 32789
View Details 55 Photos
Single story home with brick driveway and rocking chairs on the porch at 279 Rippling Ln, Winter Park, FL 32789
Lakefront property with a spacious wooden dock at 279 Rippling Ln, Winter Park, FL 32789
Lakefront property offering breathtaking water views and lush landscaping at 279 Rippling Ln, Winter Park, FL 32789
On Market For 223 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3472

  • Year Built

    1961

  • $/SqFt

    $517

Don’t miss this rare opportunity to own a slice of paradise in one of Winter Park’s most sought-after locations. FANNIE HILLMAN & ASSOCIATES.

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