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323 Results

View 323 Winter Park Florida Homes for Sale

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 274 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.

Pended $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 276 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 $1,739,000

Reduced By $56,000

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 280 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3472

  • Year Built

    1961

  • $/SqFt

    $501

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.

Home For Sale $997,000

Reduced By $202,900

Two-story farmhouse style home with white siding, gray roof, and a paved driveway at 1840 Biscayne Dr, Winter Park, FL 32789
View Details 34 Photos
Bright and airy entryway with hardwood floors and stylish decor at 1840 Biscayne Dr, Winter Park, FL 32789
Modern home office featuring large windows and comfortable seating at 1840 Biscayne Dr, Winter Park, FL 32789
Spa-like bathroom with a glass shower and gray vanity at 1840 Biscayne Dr, Winter Park, FL 32789
On Market For 299 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2641

  • Year Built

    2024

  • $/SqFt

    $378

Karolina On Killarney - Calling all medical professionals, this home is located 1.7 miles or 7 minutes to Advent Health and a mere 5.6 miles or 14 minutes to Orlando Health. COMPASS FLORIDA LLC.

Home For Sale $1,625,000

Reduced By $70,000

Brick home with lush landscaping and inviting front porch at 1650 Lakehurst Ave, Winter Park, FL 32789
View Details 61 Photos
Inviting front porch entry to this beautiful brick home at 1650 Lakehurst Ave, Winter Park, FL 32789
Elegant entryway with hardwood floors and a chandelier at 1650 Lakehurst Ave, Winter Park, FL 32789
Light and bright staircase with hardwood floors at 1650 Lakehurst Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 299 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3777

  • Year Built

    1992

  • $/SqFt

    $430

Comstock Park - Located minutes from Park Avenue, Rollins College, Advent Health, and more this home is conveniently located and zoned for the A-rated Lakemont/Maitland Middle/WPHS school district. KELLY PRICE & COMPANY LLC.

Pended $4,200,000

Luxury two-story home with lake views at 571 Lake Front Blvd, Winter Park, FL 32789
View Details 7 Photos
Luxury two-story home with lake views at 571 Lake Front Blvd, Winter Park, FL 32789
Lakefront property with modern home at 571 Lake Front Blvd, Winter Park, FL 32789
Lakefront home nestled among trees at 571 Lake Front Blvd, Winter Park, FL 32789
On Market For 309 Days

  • Bedrooms

    7

  • Full Bath(s)

    5

  • Sq. Ft.

    5500

  • Year Built

    2025

  • $/SqFt

    $764

From upscale dining and shopping to outdoor activities and renowned schools, this location balances convenience and exclusivity. PREMIER SOTHEBY'S INTL. REALTY.

Pended $799,900

Reduced By $50,000

Inviting front yard with a walkway, landscaping, and a stone fountain at 2804 Dike Rd, Winter Park, FL 32792
View Details 54 Photos
Mature landscaping, stone fountain, and a relaxing garden setting at 2804 Dike Rd, Winter Park, FL 32792
Aerial view showing home, pool, dock, and pond; large lot size at 2804 Dike Rd, Winter Park, FL 32792
Wooden dock extending over a serene pond at 2804 Dike Rd, Winter Park, FL 32792
On Market For 312 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2503

  • Year Built

    1980

  • $/SqFt

    $320

Schedule your showing today and experience the tranquility and luxury of this unique home! KELLER WILLIAMS ADVANTAGE REALTY.

Pended $1,575,000

Modern two-story home with a sleek design, balcony, and attached garage at 627 Country Club Dr, Winter Park, FL 32789
View Details 5 Photos
Contemporary home with dark exterior, balcony, and attached garage at 627 Country Club Dr, Winter Park, FL 32789
Two-story modern home with wood and concrete accents, balcony, and attached garage at 627 Country Club Dr, Winter Park, FL 32789
Modern home with a balcony, attached garage, and landscaping at 627 Country Club Dr, Winter Park, FL 32789
On Market For 74 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2858

  • Year Built

    2024

  • $/SqFt

    $551

Lake Killarney Shores - Make an appointment today before this amazing home is gone. CLASSIC HOMES.

Home For Sale $2,160,000

Reduced By $90,000

Two story house with white brick exterior, manicured lawn, and walkway at 2234 Via Luna, Winter Park, FL 32789
View Details 49 Photos
Elegant living room with high ceilings, fireplace, and access to the pool area at 2234 Via Luna, Winter Park, FL 32789
Two story house with white brick exterior, manicured lawn, and walkway at 2234 Via Luna, Winter Park, FL 32789
Expansive backyard with fire pit and seating area under lush trees at 2234 Via Luna, Winter Park, FL 32789
On Market For 320 Days

  • Bedrooms

    6

  • Full Bath(s)

    3

  • Sq. Ft.

    3554

  • Year Built

    1998

  • $/SqFt

    $608

Tuscany Terrace - This home is being sold with all the furniture but can be removed if Buyer does not want it. Some pictures are "Virtually Staged." LOKATION.

Home For Sale $849,000

Reduced By $151,000

Ranch style home with mature landscaping at 2955 Lolissa Ln, Winter Park, FL 32789
View Details 19 Photos
Open concept kitchen with island and hardwood floors at 2955 Lolissa Ln, Winter Park, FL 32789
Open living room and kitchen with hardwood floors, island, and modern appliances at 2955 Lolissa Ln, Winter Park, FL 32789
Spacious living area with hardwood floors and open concept design at 2955 Lolissa Ln, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 376 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3902

  • Year Built

    1969

  • $/SqFt

    $218

Don't miss this opportunity to live, work and play in Winter Park just 4 miles away from downtown Park Avenue shops, restaurants and recreation. COLDWELL BANKER REALTY.

Home For Sale $325,000

Reduced By $95,000

Newly renovated home with pergola and brick pavers at 1921 Dartmouth Ave, Winter Park, FL 32789
View Details 34 Photos
Relaxing patio with pergola and comfortable seating at 1921 Dartmouth Ave, Winter Park, FL 32789
Relaxing patio with pergola and comfortable seating at 1921 Dartmouth Ave, Winter Park, FL 32789
Patio furniture under pergola with plants at 1921 Dartmouth Ave, Winter Park, FL 32789
On Market For 334 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    987

  • Year Built

    1956

  • $/SqFt

    $329

Stansbury Estates - Make this your dream home today! LPT REALTY.

Pended $549,000

Reduced By $190,000

Ranch style home with stone facade and landscaped lawn at 4041 Yacht Ct, Winter Park, FL 32792
View Details 22 Photos
Elegant entryway with a large wood door and sidelights at 4041 Yacht Ct, Winter Park, FL 32792
Open concept living space with a stone fireplace and kitchen island at 4041 Yacht Ct, Winter Park, FL 32792
Modern kitchen with white cabinetry, quartz countertops and island at 4041 Yacht Ct, Winter Park, FL 32792
*IS SHORT SALE
On Market For 319 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2153

  • Year Built

    1977

  • $/SqFt

    $255

This incredible home also boasts an ideal location and with top-rated schools: Lakemont Elementary, Maitland Middle and Winter Park High. COLDWELL BANKER REALTY.

Home For Sale $340,000

Reduced By $45,000

Charming single-story home with a well-manicured lawn and inviting driveway at 5481 Park Vale Blvd, Winter Park, FL 32792
View Details 25 Photos
Bright living room with stylish furniture, modern decor, and an open layout at 5481 Park Vale Blvd, Winter Park, FL 32792
Spacious living room with tiled floors and natural light, ready for personal touches at 5481 Park Vale Blvd, Winter Park, FL 32792
Cozy main bedroom featuring a large window, ceiling fan, and dresser at 5481 Park Vale Blvd, Winter Park, FL 32792
On Market For 376 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1450

  • Year Built

    1980

  • $/SqFt

    $234

Oakcrest - The sitting area makes it great for BBQs! A must see! OPENDOOR BROKERAGE LLC.

Home For Sale $699,900

Reduced By $200,099

Newly renovated home with gray exterior and stone accents at 2612 Lafayette Ave, Winter Park, FL 32789
View Details 41 Photos
Newly renovated home with gray exterior and stone accents, large tree in front at 2612 Lafayette Ave, Winter Park, FL 32789
Light and bright entryway with gray walls and wood floors at 2612 Lafayette Ave, Winter Park, FL 32789
Entryway with contemporary decor, hardwood floors, and view to living room at 2612 Lafayette Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 440 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2447

  • Year Built

    1956

  • $/SqFt

    $286

Winter Park Village - Discover refined elegance at 2612 Lafayette Avenue in Winter Park EXP REALTY LLC.

Pended $318,000

Reduced By $57,000

Charming bungalow with a well-maintained lawn at 1908 Carrigan Ave, Winter Park, FL 32792
View Details 29 Photos
Living room featuring modern furniture and hardwood floors at 1908 Carrigan Ave, Winter Park, FL 32792
Bright living room with hardwood floors at 1908 Carrigan Ave, Winter Park, FL 32792
Spacious main bedroom with a comfortable bed and hardwood floors at 1908 Carrigan Ave, Winter Park, FL 32792
On Market For 394 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1122

  • Year Built

    1954

  • $/SqFt

    $283

Temple Terrace - Don't miss the chance to make this your dream home! OPENDOOR BROKERAGE LLC.

Pended $850,000

Reduced By $145,000

Two-story home with terracotta tile roof and brick paver driveway at 1310 Aloma Ave, Winter Park, FL 32789
View Details 28 Photos
Front view of two-story home with terracotta tile roof and brick driveway at 1310 Aloma Ave, Winter Park, FL 32789
Two-story home showcasing terracotta tile roof and landscaping at 1310 Aloma Ave, Winter Park, FL 32789
Bright living room with hardwood floors, fireplace, and French doors at 1310 Aloma Ave, Winter Park, FL 32789
On Market For 383 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2533

  • Year Built

    1926

  • $/SqFt

    $336

Sylvan Lake Shores - Centrally located to Rollins College and Park Avenue. KELLY PRICE & COMPANY LLC.

Home For Sale $4,500,000

Reduced By $995,000

Luxury home with circular driveway and two-car garage at 421 Lakewood Dr, Winter Park, FL 32789
View Details 41 Photos
Luxury home with circular driveway and two-car garage at 421 Lakewood Dr, Winter Park, FL 32789
Luxury home with pool and lake view at 421 Lakewood Dr, Winter Park, FL 32789
Resort-style pool with spa and expansive patio at 421 Lakewood Dr, Winter Park, FL 32789
On Market For 292 Days

  • Bedrooms

    5

  • Full Bath(s)

    7

  • Sq. Ft.

    5847

  • Year Built

    1957

  • $/SqFt

    $770

Osceola Shores - All within walking distance to downtown Winter Park and famed Park Avenue… PREMIER SOTHEBY'S INTL. REALTY.

Pended $562,000

Reduced By $88,000

Inviting rectangular swimming pool in a backyard oasis at 5233 Lake Howell Rd, Winter Park, FL 32792
View Details 45 Photos
Charming single story home with manicured lawn at 5233 Lake Howell Rd, Winter Park, FL 32792
Welcoming porch with blue rocking chairs and a blue front door at 5233 Lake Howell Rd, Winter Park, FL 32792
Bright living room with comfy sofas, a fireplace, and hardwood floors at 5233 Lake Howell Rd, Winter Park, FL 32792
On Market For 577 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1778

  • Year Built

    1956

  • $/SqFt

    $316

Tanglewood - Refreshing. Peaceful. Happy. Inviting. Private. Convenient. CADENCE LIFESTYLE REAL ESTATE.

Pended $1,550,000

Reduced By $375,000

Two-story modern home with two-car garage and landscaped yard at 1871 Taylor Ave, Winter Park, FL 32789
View Details 41 Photos
Two-story modern home with two-car garage and landscaped yard at 1871 Taylor Ave, Winter Park, FL 32789
Covered front porch with stone facade, blue door, and seating area at 1871 Taylor Ave, Winter Park, FL 32789
Bright entryway with stone accent wall and modern console table at 1871 Taylor Ave, Winter Park, FL 32789
On Market For 223 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3401

  • Year Built

    2016

  • $/SqFt

    $456

Contact us today for more information on the assumable mortgage or to schedule a private showing. CORCORAN PREMIER REALTY.

Home For Sale $750,000

Aerial view showing property lines and lot size at 2009 Oglesby Ave, Winter Park, FL 32789
View Details 2 Photos
Charming house with white picket fence and brick mailbox at 2009 Oglesby Ave, Winter Park, FL 32789
On Market For 661 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1318

  • Year Built

    1948

  • $/SqFt

    $569

Located on the same block as the new 222-unit Seven41 apartment complex, this is a great development opportunity in an ideal Winter Park location. CORCORAN PREMIER REALTY.

Pended $824,900

Reduced By $99,100

Contemporary home with a sleek design and modern garage at 737 N Capen Ave, Winter Park, FL 32789
View Details 37 Photos
Modern home with sleek design, wood garage door, and landscaped lawn at 737 N Capen Ave, Winter Park, FL 32789
Contemporary house with gray roof, wood garage door, and manicured lawn at 737 N Capen Ave, Winter Park, FL 32789
Stylish home, gray roof, wood garage door, and lush green surroundings at 737 N Capen Ave, Winter Park, FL 32789
On Market For 268 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1930

  • Year Built

    2021

  • $/SqFt

    $427

Room Feature: Linen Closet In Bath (Primary Bedroom). LPT REALTY, LLC.

Home For Sale $550,000

Reduced By $49,000

Modern single story home with black garage door at 2627 Ambergate Rd, Winter Park, FL 32792
View Details 19 Photos
Modern kitchen with granite island and stainless steel appliances at 2627 Ambergate Rd, Winter Park, FL 32792
Updated kitchen with granite countertops and island at 2627 Ambergate Rd, Winter Park, FL 32792
Living room with gray sectional sofa and blue chair at 2627 Ambergate Rd, Winter Park, FL 32792
On Market For 799 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1805

  • Year Built

    1959

  • $/SqFt

    $305

Winter Park Estates - *All information is intended to be accurate but is not guaranteed. COLDWELL BANKER REALTY.

Pended $1,600,000

Reduced By $300,000

Two-story light blue modern home with a metal roof and driveway at 281 Brewer Ave, Winter Park, FL 32789
View Details 60 Photos
Modern two-story home with gray paver driveway and landscaped entry at 281 Brewer Ave, Winter Park, FL 32789
Contemporary house with metal roof, paver driveway, and landscaping at 281 Brewer Ave, Winter Park, FL 32789
Two-story home showcasing a metal roof and paver driveway at 281 Brewer Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 514 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4029

  • Year Built

    2022

  • $/SqFt

    $397

Home comes with a ONE-YEAR BUILDERS WARRANTY! Schedule a private tour today! KELLER WILLIAMS REALTY AT THE PARKS.

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