227 Results

View 227 Winter Park Florida Homes for Sale

Pended $1,175,000

Reduced By $210,000

Inviting front entry with gray double doors and lush landscaping at 850 Juanita Rael, Winter Park, FL 32789
Welcoming front entrance with gray double doors and neat landscaping at 850 Juanita Rael, Winter Park, FL 32789
Bright entryway with terracotta tile flooring and double white doors at 850 Juanita Rael, Winter Park, FL 32789
On Market For 234 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2306

  • Year Built

    1966

  • $/SqFt

    $510

Green Oaks - With its desirable single-story layout, large outdoor space, and a corner lot, this ranch-style home offers a blend of comfort and functionality for today's lifestyle. KELLY PRICE & COMPANY LLC.

Home For Sale $1,795,000

Reduced By $190,000

Modern kitchen with large island and stainless steel appliances at 508 W Swoope Ave, Winter Park, FL 32789
Open living room with light hardwood floors and modern furniture at 508 W Swoope Ave, Winter Park, FL 32789
Modern kitchen with a large island and dark brown cabinets at 508 W Swoope Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 228 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4133

  • Year Built

    2021

  • $/SqFt

    $434

Schedule a private viewing today and experience the epitome of luxury living near Park Ave. COLDWELL BANKER REALTY.

Home For Sale $2,495,000

Reduced By $300,000

Modern two-story home with gray and white exterior, two-car garage, and landscaped front yard at dusk at 2412 Chantilly Ave, Winter Park, FL 32789
Modern home exterior featuring gray and white siding, a two-car garage, and a stylish entryway at 2412 Chantilly Ave, Winter Park, FL 32789
Two-car garage with gray doors and gravel driveway at 2412 Chantilly Ave, Winter Park, FL 32789
On Market For 247 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4500

  • Year Built

    2024

  • $/SqFt

    $554

Winter Park Village - Experience the pinnacle of luxury living with this exceptional new construction home.
Brought to you by https://my.matterport.com/show/?m=hii6iJs7gyG COMPASS FLORIDA LLC.

Home For Sale $889,000

Reduced By $111,000

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 254 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3902

  • Year Built

    1969

  • $/SqFt

    $228

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 $1,750,000

Reduced By $100,000

Inviting pool area with covered patio at 1350 Lyndale Blvd, Winter Park, FL 32789
Two-story house with gray accents, a paved driveway, and landscaping at 1350 Lyndale Blvd, Winter Park, FL 32789
Formal dining room with hardwood floors, chandelier, and large window at 1350 Lyndale Blvd, Winter Park, FL 32789
On Market For 256 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3478

  • Year Built

    2003

  • $/SqFt

    $503

Dixie Terrace -

HOMEVEST REALTY.

Home For Sale $370,000

Reduced By $28,990

Newly renovated Ranch style home with a white exterior and landscaped yard at 5118 Lake Howell Rd, Winter Park, FL 32792
Bright and airy entryway with tile flooring, leading to other rooms at 5118 Lake Howell Rd, Winter Park, FL 32792
Spacious bedroom with grey tile flooring and ample closet space at 5118 Lake Howell Rd, Winter Park, FL 32792
*IS SHORT SALE
On Market For 257 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1160

  • Year Built

    1957

  • $/SqFt

    $319

Tanglewood - (Some pictures are one year old) LA ROSA REALTY KISSIMMEE.

Home For Sale $384,900

Reduced By $54,100

Lovely ranch home with brick accents and a mature tree in the front yard at 565 Heritage Blvd, Winter Park, FL 32792
Bright entryway with tiled floor, large mirror, and wood door at 565 Heritage Blvd, Winter Park, FL 32792
Dining area with white table and chairs, view into living room at 565 Heritage Blvd, Winter Park, FL 32792
On Market For 260 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1512

  • Year Built

    1967

  • $/SqFt

    $255

BEAR TEAM REAL ESTATE.

Home For Sale $335,000

Reduced By $85,000

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 242 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    987

  • Year Built

    1956

  • $/SqFt

    $339

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

Home For Sale $488,000

Reduced By $80,000

Ranch style home with landscaped yard and covered porch at 7320 Fieldcrest Ave, Winter Park, FL 32792
One-story home with green lawn and palm trees at 7320 Fieldcrest Ave, Winter Park, FL 32792
House with lush landscaping and large trees at 7320 Fieldcrest Ave, Winter Park, FL 32792
On Market For 262 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1919

  • Year Built

    1970

  • $/SqFt

    $254

Woodcrest - Fall In Love With The Tastfully Designs On The New Kitchen, Bathrooms, Inside Laundryroom With Workspace, Separate Living Room. No Details Are Left Behind! COLDWELL BANKER REALTY.

Home For Sale $549,000

Reduced By $190,000

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 283 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 $356,000

Reduced By $29,000

Spacious living room with light tile floors and sectional sofa at 5481 Park Vale Blvd, Winter Park, FL 32792
Spacious living room featuring travertine tile floors and sliding glass doors leading to backyard at 5481 Park Vale Blvd, Winter Park, FL 32792
Bright bedroom with ensuite bathroom and neutral color palette at 5481 Park Vale Blvd, Winter Park, FL 32792
On Market For 266 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1450

  • Year Built

    1980

  • $/SqFt

    $246

Oakcrest - Don't miss out on this fantastic opportunity to make this house your own! OPENDOOR BROKERAGE LLC.

Home For Sale $599,000

Reduced By $50,000

Mid-century modern home with carport, large tree, and lawn at 220 Blossom Ln, Winter Park, FL 32789
Mid-century modern home with carport, large tree, and lawn at 220 Blossom Ln, Winter Park, FL 32789
Mid-century modern home with carport, large tree, and lawn at 220 Blossom Ln, Winter Park, FL 32789
On Market For 287 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2193

  • Year Built

    1954

  • $/SqFt

    $273

Schedule a private tour today and experience luxury living at its finest at 220 Blossom Lane. SUMMERHILL REALTY GROUP LLC.

Home For Sale $659,000

Reduced By $130,000

Newly renovated home exterior with gray siding at 336 Saint Dunstan Way, Winter Park, FL 32792
Light and airy living room with hardwood floors at 336 Saint Dunstan Way, Winter Park, FL 32792
Living room with hardwood floors and patio doors at 336 Saint Dunstan Way, Winter Park, FL 32792
On Market For 313 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1715

  • Year Built

    1964

  • $/SqFt

    $384

This home is one of a kind and will not last long. PARK TOWN REAL ESTATE LLC.

Home For Sale $749,900

Reduced By $150,099

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
On Market For 319 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2447

  • Year Built

    1956

  • $/SqFt

    $306

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

Pended $539,000

Reduced By $10,000

Large backyard with mature trees and privacy fence at 2313 Loch Lomond Dr, Winter Park, FL 32792
Residential lot with mature trees and open space at 2313 Loch Lomond Dr, Winter Park, FL 32792
Dated kitchen with dark cabinets and ample counter space at 2313 Loch Lomond Dr, Winter Park, FL 32792
On Market For 268 Days
  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    1570

  • Year Built

    1948

  • $/SqFt

    $343

Buyer is responsible for doing any research and contacting the city of Winter Park on splits, zoning, building codes, permits, etc. RE/MAX 200 REALTY.

Home For Sale $1,977,000

Reduced By $623,000

Aerial view of a house near a lake in a quiet neighborhood at 1340 Chestnut Ave, Winter Park, FL 32789
Aerial view of a modern home with a flat roof and attached garage at 1340 Chestnut Ave, Winter Park, FL 32789
Bird's eye view of a contemporary house with a pool and lush landscaping at 1340 Chestnut Ave, Winter Park, FL 32789
On Market For 321 Days
  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    4182

  • Year Built

    1963

  • $/SqFt

    $473

Lake Knowles Terrace - With its ideal blend of classic charm and modern updates, this fully remodeled residence is a rare find, offering an exceptional opportunity for those seeking a contemporary lifestyle in a sought-after WRA BUSINESS & REAL ESTATE.

Home For Sale $338,000

Reduced By $37,000

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 277 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1122

  • Year Built

    1954

  • $/SqFt

    $301

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

Home For Sale $1,525,000

Reduced By $350,000

Modern farmhouse style home with black trim and landscaping at 1101 Kenwood Ave, Winter Park, FL 32789
Stylish front entrance with black double doors and gray tile at 1101 Kenwood Ave, Winter Park, FL 32789
Bright and airy entryway with light hardwood floors at 1101 Kenwood Ave, Winter Park, FL 32789
On Market For 343 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2955

  • Year Built

    2024

  • $/SqFt

    $516

Dixie Terrace - Schedule your private showing today and be among the first to experience the charm and luxury of this exceptional residence! CORCORAN PREMIER REALTY.

Pended $850,000

Reduced By $145,000

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 360 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.

Pended $1,499,000

Reduced By $451,000

Mediterranean style home with a three-car garage and lush landscaping at 513 Worthington Dr, Winter Park, FL 32789
Entryway with a wooden door, brick pavers, and a green hedge at 513 Worthington Dr, Winter Park, FL 32789
Pool area with a fountain, patio furniture, and a grill at 513 Worthington Dr, Winter Park, FL 32789
On Market For 412 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3112

  • Year Built

    2005

  • $/SqFt

    $482

This home shows well and is turn key ready due to recent renovations. COLONIALTOWN REALTY.

Pended $4,500,000

Reduced By $995,000

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 291 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

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 455 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
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 253 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

Charming house with white picket fence and brick mailbox at 2009 Oglesby Ave, Winter Park, FL 32789
On Market For 539 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

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 146 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 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 677 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

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 392 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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Call to Schedule a Showing

(407) 967-1435

(407) 967-1435