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View 141 32789 Florida Homes for Sale

Home For Sale $1,350,000

Charming home featuring a circular brick driveway, manicured landscaping, and a bright white exterior at 181 N Phelps Ave, Winter Park, FL 32789
View Details 50 Photos
Inviting front porch featuring a stylish door, sleek black shutters and a cozy seating area at 181 N Phelps Ave, Winter Park, FL 32789
Aerial view of a home featuring a long rectangular pool and mature landscaping at 181 N Phelps Ave, Winter Park, FL 32789
Backyard pool area with cabana, dining table, and lush greenery at 181 N Phelps Ave, Winter Park, FL 32789
On Market For 39 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3000

  • Year Built

    1948

  • $/SqFt

    $450

Sylvan Lake Shores - Additional House Benefits include: Remodeled living room ; Original wood fireplace ; New AC (2021) ; Tankless water heater 2021 ; Dual masters ; 4 full baths ; Insulated 2 car garage with exAC Garage ; New vinyl flooring ; Remodeled office / guest room with built-in cabinets ; Heated swimming pool ; Renovated backyard with artificial grass and summer kitchen (outdoor furniture negotiable) ; New detached office space w/ air conditioning ; Outdoor ambient lighting ; New alarm system ; All appliances will stay ; Extended Kitchen Island ; New sprinkler system ; Outdoor shed storage; Acclimate Attic ; New PVC Wood Deck ; Water filtration system in the kitchen ; Underground gas line for stovetop, water heater, and pool heater Located just minutes from Windsong, Park Avenue, Baldwin Park, top-rated schools (Brookshire, Glenridge, WPHS), parks, dining, and shopping, this home offers both charm and convenience. ORLANDO BROTHERS REAL ESTATE LLC.

Home For Sale $1,675,000

Beautifully landscaped two story home with modern architectural details at 607 Ellen Dr, Winter Park, FL 32789
View Details 4 Photos
Waterfront homes featuring private docks and pools, situated on a picturesque lake at 607 Ellen Dr, Winter Park, FL 32789
Scenic lake view featuring a private dock and residents paddle boarding at 607 Ellen Dr, Winter Park, FL 32789
Elegant two-story house boasting contemporary design with a flat roof and vibrant landscaping at 607 Ellen Dr, Winter Park, FL 32789
On Market For 42 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2812

  • Year Built

    2025

  • $/SqFt

    $596

Last home available in the neighborhood and is priced well as this home will not last long! ! COMMUNITY REALTY ASSOCIATES.

Home For Sale $1,295,000

Charming single-Gathering home featuring a light-colored exterior, wood-look garage door, and well-manicured landscaping at 1611 Chestnut Ave, Winter Park, FL 32789
View Details 84 Photos
Aerial view of the home showcasing its gray roof, backyard space, and proximity to surrounding neighborhood at 1611 Chestnut Ave, Winter Park, FL 32789
Property highlighted by boundary lines showing its location and surrounding homes and well-manicured lawns at 1611 Chestnut Ave, Winter Park, FL 32789
Overhead image of a neighborhood featuring well-maintained homes, private pools, and mature landscaping at 1611 Chestnut Ave, Winter Park, FL 32789
On Market For 42 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2916

  • Year Built

    1973

  • $/SqFt

    $444

Lake Knowles Terrace - According to the owner backyard can accommodate a POOL! PARK AVENUE REALTY LLC.

Pended $1,595,000

Charming home featuring columns, a black roof, and decorative plants surrounded by privacy walls at 335 Beloit Ave, Winter Park, FL 32789
View Details 31 Photos
Charming pink home featuring stately white columns, a landscaped front yard, and tropical palm trees at 335 Beloit Ave, Winter Park, FL 32789
Detailed floor plan showcasing the layout of the home's rooms and dimensions at 335 Beloit Ave, Winter Park, FL 32789
Inviting foyer with tile floors, artwork, and a view into the living space at 335 Beloit Ave, Winter Park, FL 32789
On Market For 31 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2420

  • Year Built

    1978

  • $/SqFt

    $659

Enjoy a NEW A/C unit (2024), new washer/dryer (2024), and one of the best locations in the City of Winter Park! ! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,195,000

Charming single-story home with a well-maintained lawn, stucco facade, and a beautiful terracotta tile roof at 1690 Oneco Ave, Winter Park, FL 32789
View Details 28 Photos
Inviting single-story home with a brick driveway, lush lawn, and a charming terracotta-tiled roof at 1690 Oneco Ave, Winter Park, FL 32789
Beautiful single-story home featuring a well-manicured lawn, brick driveway, and a classic terracotta tile roof at 1690 Oneco Ave, Winter Park, FL 32789
Elegant foyer featuring arched entryways, a dark wood front door, neutral paint and travertine tile flooring at 1690 Oneco Ave, Winter Park, FL 32789
On Market For 43 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2703

  • Year Built

    1967

  • $/SqFt

    $442

Winter Park Heights - NOTE: all interior walls recently painted neutral soft white... also, this home has accessible elemements to it, including a handicapped ramp in garage.... PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $764,900

Reduced By $30,100

Charming single-story home with a white exterior, gray shutters, and a well-maintained front yard at 1037 N Virginia Ave, Winter Park, FL 32789
View Details 39 Photos
Lovely single-story house with a white exterior, attached garage, and green grass at 1037 N Virginia Ave, Winter Park, FL 32789
Beautiful single-story home featuring a white exterior, covered porch, and well-manicured landscaping at 1037 N Virginia Ave, Winter Park, FL 32789
Inviting covered front porch with decorative iron supports and black front door at 1037 N Virginia Ave, Winter Park, FL 32789
On Market For 42 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1101

  • Year Built

    1960

  • $/SqFt

    $695

Don’t miss this “one of kind – live your best Winter Park life” opportunity! KELLER WILLIAMS WINTER PARK.

Pended $425,000

Charming blue home featuring a landscaped front yard, carport, and inviting curb appeal at 328 Lake Fair Ln, Winter Park, FL 32789
View Details 69 Photos
Inviting front entrance with a quaint bench, lush landscaping, and vibrant blue exterior paint at 328 Lake Fair Ln, Winter Park, FL 32789
A close-up of the home's front door, featuring a dark finish and wood post accents at 328 Lake Fair Ln, Winter Park, FL 32789
Bright dining room with hardwood floors, modern fan, and view to adjacent rooms at 328 Lake Fair Ln, Winter Park, FL 32789
On Market For 43 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1485

  • Year Built

    1958

  • $/SqFt

    $286

Fairbanks Shores - Don’t miss the chance to own this lakefront gem—a perfect blend of historic charm, modern upgrades, and an unbeatable location. Schedule your private tour today! RE/MAX 200 REALTY.

Home For Sale $1,225,000

Reduced By $25,000

Charming single-story home featuring a red tile roof, mature landscaping, and an attached garage at 1585 Chestnut Ave, Winter Park, FL 32789
View Details 45 Photos
Inviting single-story home with lush landscaping, brick driveway, and a cozy front yard at 1585 Chestnut Ave, Winter Park, FL 32789
Attractive home showcasing neat landscaping, a gray garage door, and a clay tile roof at 1585 Chestnut Ave, Winter Park, FL 32789
Bright dining room featuring a ceiling fan, large windows, and unique tile flooring at 1585 Chestnut Ave, Winter Park, FL 32789
On Market For 42 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2220

  • Year Built

    1959

  • $/SqFt

    $552

Lake Knowles Terrace - Don’t miss your chance to own a piece of Winter Parks most desirable neighborhood! KELLER WILLIAMS WINTER PARK.

Home For Sale $2,395,000

Contemporary two-story home featuring a two-car garage and well-manicured landscaping at 2412 Chantilly Ave, Winter Park, FL 32789
View Details 48 Photos
Modern home showcases a two-car garage, gravel driveway, and lush, green landscaping at 2412 Chantilly Ave, Winter Park, FL 32789
Elegant entryway featuring a modern glass door, stone path, and stylish landscaping at 2412 Chantilly Ave, Winter Park, FL 32789
Bright foyer with hardwood floors and a modern glass door leading to the exterior at 2412 Chantilly Ave, Winter Park, FL 32789
On Market For 45 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4506

  • Year Built

    2024

  • $/SqFt

    $532

Winter Park Village - Perfectly positioned in a coveted Winter Park local, near top-rated schools and just moments from Park Avenue’s upscale shopping and dining, this exceptional residence offers the pinnacle of contemporary luxury living. COMPASS FLORIDA LLC.

Pended $2,200,000

Stately two-story home boasts a clay tile roof, lush landscaping, and a long, curved driveway at 1446 Berkshire Ave, Winter Park, FL 32789
View Details 92 Photos
Stately two-story home boasts a clay tile roof, lush landscaping, and a long, curved driveway at 1446 Berkshire Ave, Winter Park, FL 32789
Close up shows the home's architectural details and manicured landscaping with towering palms at 1446 Berkshire Ave, Winter Park, FL 32789
Charming facade features a secure gated entry, arched windows, and an attached two-car garage at 1446 Berkshire Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 47 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4612

  • Year Built

    1925

  • $/SqFt

    $477

With its prime Winter Park location, exceptional privacy, and resort-style amenities, this remarkable home offers the perfect blend of style, comfort, and convenience in one of Winter Park’s most desirable neighborhoods. SERHANT.

Pended $1,295,000

Inviting single-story home with a white exterior, well-manicured landscaping, and a large shade tree at 1932 Temple Dr, Winter Park, FL 32789
View Details 55 Photos
Inviting single-story home with a white exterior, well-manicured landscaping, and a large shade tree at 1932 Temple Dr, Winter Park, FL 32789
Charming single-story home with lush landscaping and a grand shade tree at twilight at 1932 Temple Dr, Winter Park, FL 32789
Bright and airy living room featuring a large white sectional, wood floors, and an open layout at 1932 Temple Dr, Winter Park, FL 32789
On Market For 48 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2432

  • Year Built

    1952

  • $/SqFt

    $532

Lake Knowles Terrace - A great investment opportunity to live among the finest homes in Winter Park and in well-established neighborhood providing a lifestyle like no other. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $534,900

Charming two-story home features a manicured lawn, long driveway, and inviting front entrance at 1481 Harmon Ave, Winter Park, FL 32789
View Details 31 Photos
Inviting two-story home with a well-kept lawn and quaint pathway leading to the front porch at 1481 Harmon Ave, Winter Park, FL 32789
Welcoming front porch featuring fresh exterior paint and bright windows at 1481 Harmon Ave, Winter Park, FL 32789
Bright living room with hardwood floors, white walls, and decorative furnishings at 1481 Harmon Ave, Winter Park, FL 32789
On Market For 50 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1900

  • Year Built

    1926

  • $/SqFt

    $282

Lawndale - Don’t miss out on this rare opportunity—schedule your private showing today! KELLER WILLIAMS WINTER PARK.

Home For Sale $1,950,000

Two-story white house with a front yard and landscaping at 622 Penn Pl, Winter Park, FL 32789
View Details 26 Photos
Elegant entryway with hardwood floors, chandelier, and staircase at 622 Penn Pl, Winter Park, FL 32789
Spacious living room with hardwood floors, fireplace, and French doors at 622 Penn Pl, Winter Park, FL 32789
Open living room with hardwood floors and views into kitchen at 622 Penn Pl, Winter Park, FL 32789
On Market For 53 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2767

  • Year Built

    2001

  • $/SqFt

    $705

Don’t miss your chance to make this exceptional property your next home! COMMUNITY REALTY ASSOCIATES.

Pended $3,130,000

Modern two-story home with gray brick exterior, two-car garage, and a paved driveway at 210 E Lake Sue Ave, Winter Park, FL 32789
View Details 46 Photos
Stunning contemporary home at night, featuring gray brick and a landscaped yard at 210 E Lake Sue Ave, Winter Park, FL 32789
Modern front entry with glass door, gray brick, and landscaping at 210 E Lake Sue Ave, Winter Park, FL 32789
Elegant entryway with wood floors, high ceilings, and built-in wet bar at 210 E Lake Sue Ave, Winter Park, FL 32789
On Market For 22 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4188

  • Year Built

    2025

  • $/SqFt

    $747

Charmont - Schedule your private showing today and experience the epitome of luxury Winter Park living. COMPASS FLORIDA LLC.

Home For Sale $1,895,000

Reduced By $100,000

Charming two-story coral home with landscaped front yard and brick pathway at 817 Antonette Ave, Winter Park, FL 32789
View Details 60 Photos
Elegant entryway with checkered floor and unique decor at 817 Antonette Ave, Winter Park, FL 32789
Green striped sitting room with French doors opening to sunroom at 817 Antonette Ave, Winter Park, FL 32789
Green striped sitting room with ample natural light and unique decor at 817 Antonette Ave, Winter Park, FL 32789
On Market For 53 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3971

  • Year Built

    1990

  • $/SqFt

    $477

College Place - Don't miss the opportunity to schedule a private viewing of this unique, one-of-a-kind treasure! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,279,000

Charming two-story home featuring a tile roof, a pergola over the garage, and a lush landscaped yard at 141 Oakwood Way, Winter Park, FL 32789
View Details 58 Photos
View of house featuring a tile roof, well-manicured lawn, mature trees, and a paved driveway leading to the garage at 141 Oakwood Way, Winter Park, FL 32789
Close up of home's entry featuring a blue double door, manicured bushes, walkway, and exterior accent lighting at 141 Oakwood Way, Winter Park, FL 32789
Bright dining room with hardwood floors and chandelier at 141 Oakwood Way, Winter Park, FL 32789
On Market For 55 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3909

  • Year Built

    2015

  • $/SqFt

    $583

Charmont - This is more than a home—it’s an expression of refined living and timeless design. Schedule your private tour today! MAINFRAME REAL ESTATE.

Home For Sale $2,119,000

Two-story modern home with light-colored facade, wood garage doors, and landscaping at 785 N Phelps Ave, Winter Park, FL 32789
View Details 11 Photos
New home construction featuring concrete block walls and open floor plan at 785 N Phelps Ave, Winter Park, FL 32789
Modern kitchen with white cabinets, a large island, and stainless steel appliances at 785 N Phelps Ave, Winter Park, FL 32789
Concrete block wall with window opening showcases backyard greenery and bamboo at 785 N Phelps Ave, Winter Park, FL 32789
On Market For 56 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    2964

  • Year Built

    2025

  • $/SqFt

    $715

Comstock Park - Don’t miss the chance to make this stunning property your own — call today for more details and secure your dream home, ready by September 2025! COMPASS FLORIDA LLC.

Home For Sale $1,850,000

Reduced By $100,000

Two-story house with white exterior, gray roof, and landscaped lawn at 1470 Place Picardy, Winter Park, FL 32789
View Details 27 Photos
Elegant two-story house with white exterior, gray roof, and a manicured lawn at 1470 Place Picardy, Winter Park, FL 32789
Bright entryway with hardwood floors and a classic white door at 1470 Place Picardy, Winter Park, FL 32789
Spacious Gathering room with hardwood floors, built-in shelving, and fireplace at 1470 Place Picardy, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 56 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4227

  • Year Built

    2003

  • $/SqFt

    $438

Fontainebleau - Please see attachments for the full list of improvements. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $389,900

Reduced By $9,100

Light blue house with palm trees, walkway, and driveway at 1930 Albert Lee Pkwy, Winter Park, FL 32789
View Details 76 Photos
Cute light blue house with a walkway leading to the front door at 1930 Albert Lee Pkwy, Winter Park, FL 32789
Ranch style home with a light blue exterior and landscaped yard at 1930 Albert Lee Pkwy, Winter Park, FL 32789
Light blue house with a white garage and a mailbox at 1930 Albert Lee Pkwy, Winter Park, FL 32789
On Market For 51 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1262

  • Year Built

    1955

  • $/SqFt

    $309

Albert Lee Ridge - Don’t miss out on this opportunity to own in one of Central Florida’s most desirable neighborhoods. FLORIDA ONE REAL ESTATE LLC.

Home For Sale $1,350,000

Reduced By $30,000

Beautiful home with a large front yard, paved driveway and lush landscaping at 1400 S Pennsylvania Ave, Winter Park, FL 32789
View Details 50 Photos
Bright entryway with a large, black curio cabinet and white door at 1400 S Pennsylvania Ave, Winter Park, FL 32789
Open concept dining room with a view of the kitchen and living room at 1400 S Pennsylvania Ave, Winter Park, FL 32789
Modern dining room features an oval table, rattan light, and neutral decor at 1400 S Pennsylvania Ave, Winter Park, FL 32789
On Market For 58 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2060

  • Year Built

    1962

  • $/SqFt

    $655

Banks Colonial Estates - Be sure and schedule a viewing. JACK KELLER INC.

Home For Sale $383,500

Reduced By $35,000

Charming single-story home with a brick accent, green lawn, and a long, inviting driveway at 942 Hanover Ave, Winter Park, FL 32789
View Details 32 Photos
Quaint single-story home showcasing a brick facade, green lawn, and mature trees at 942 Hanover Ave, Winter Park, FL 32789
Bright, open living room featuring hardwood floors, neutral walls, and large windows overlooking the lush yard at 942 Hanover Ave, Winter Park, FL 32789
Bright bedroom features hardwood floors, a ceiling fan, and multiple windows offering natural light at 942 Hanover Ave, Winter Park, FL 32789
On Market For 58 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1345

  • Year Built

    1956

  • $/SqFt

    $285

Room dimensions are: Living Room — 19'x12' Kitchen — 10'x6 1/2' Master BR — 16'x11' 2nd BR — 13'x11' Sunroom — 12'x12 1/2' Dining — 10x9 1/2' HOME SOLD REALTY LLC.

Home For Sale $1,759,000

Two-story home with modern design, three-car garage, and landscaped front yard at 1660 Walnut Ave, Winter Park, FL 32789
View Details 11 Photos
Spacious living room with large windows, comfortable seating, and a modern aesthetic at 1660 Walnut Ave, Winter Park, FL 32789
Modern kitchen with gray cabinetry, center island, and stainless steel appliances at 1660 Walnut Ave, Winter Park, FL 32789
Bright bedroom with a ceiling fan, neutral color palette, and stylish decor at 1660 Walnut Ave, Winter Park, FL 32789
On Market For 60 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2172

  • Year Built

    2025

  • $/SqFt

    $810

Lake Knowles Terrace - Don’t miss the opportunity to make this stunning Winter Park home yours. COMPASS FLORIDA LLC.

Pended $1,500,000

Inviting front porch with blue door and screened enclosure at 747 Mcintyre Ave, Winter Park, FL 32789
View Details 44 Photos
Cute one-story house with a spacious lawn at 747 Mcintyre Ave, Winter Park, FL 32789
Cute one-story house with a spacious lawn at 747 Mcintyre Ave, Winter Park, FL 32789
Cute one-story house with a spacious lawn at 747 Mcintyre Ave, Winter Park, FL 32789
On Market For 26 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1457

  • Year Built

    1950

  • $/SqFt

    $1,030

Opportunities like this are a rare find in Winter Park! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,995,000

A charming two-story home with light blue shutters and manicured lawn at 1400 Place Picardy, Winter Park, FL 32789
View Details 48 Photos
Elegant front entry with a wood door, flanked by light blue shutters at 1400 Place Picardy, Winter Park, FL 32789
Bright and spacious entryway with hardwood floors and blue patterned wallpaper at 1400 Place Picardy, Winter Park, FL 32789
Open dining room with hardwood floors, blue accents and chandelier at 1400 Place Picardy, Winter Park, FL 32789
On Market For 64 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4411

  • Year Built

    2008

  • $/SqFt

    $679

Fontainebleau - Call today to schedule your private showing. You will Love living here! PREMIER SOTHEBY'S INTL. REALTY.

Pended $599,900

Reduced By $50,100

Modern two-story house with gray siding, paver driveway, and landscaped lawn at 1875 Staunton Ave, Winter Park, FL 32789
View Details 24 Photos
Modern two-story house with gray siding, paver driveway, and landscaped lawn at 1875 Staunton Ave, Winter Park, FL 32789
Modern two-story house with gray siding, paver driveway, and landscaped lawn at 1875 Staunton Ave, Winter Park, FL 32789
Inviting front entrance with gray siding, paver walkway, and potted plants at 1875 Staunton Ave, Winter Park, FL 32789
On Market For 63 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2036

  • Year Built

    1954

  • $/SqFt

    $295

Karolina On Killarney - You are less than 2 miles from Park Avenue. THE AGENCY ORLANDO.

Pended $579,000

Reduced By $10,000

Inviting front porch with patterned tile, wooden post, and a charming wreath at 1424 Cavendish Rd, Winter Park, FL 32789
View Details 47 Photos
Relaxing backyard oasis featuring a refreshing pool with patio furniture at 1424 Cavendish Rd, Winter Park, FL 32789
Charming bungalow with lush landscaping, driveway, and a green exterior at 1424 Cavendish Rd, Winter Park, FL 32789
House exterior with a green facade, black garage door, and manicured lawn at 1424 Cavendish Rd, Winter Park, FL 32789
On Market For 64 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1132

  • Year Built

    1949

  • $/SqFt

    $511

Don’t miss the opportunity to make this Gem your new home! KEYSEEKERS REAL ESTATE.

Pended $414,000

Reduced By $17,000

Charming yellow house with a brick driveway and well-manicured lawn at 2111 Staunton Ave, Winter Park, FL 32789
View Details 23 Photos
Bright living room with hardwood floors, comfy seating, and modern decor at 2111 Staunton Ave, Winter Park, FL 32789
Spacious living area showcasing hardwood floors and ample natural light at 2111 Staunton Ave, Winter Park, FL 32789
Spacious bedroom with light walls, hardwood floors, and built-in storage at 2111 Staunton Ave, Winter Park, FL 32789
On Market For 64 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1292

  • Year Built

    1954

  • $/SqFt

    $320

This property is a true gem, offering comfort and sophistication. OPENDOOR BROKERAGE LLC.

Home For Sale $1,599,900

Two-story home with a modern design, dark brown garage doors, and landscaping at 1417 Miller Ave, Winter Park, FL 32789
View Details 4 Photos
Home with a pool, outdoor kitchen, and relaxing lounge area at 1417 Miller Ave, Winter Park, FL 32789
Ground floor plan showcasing an open layout with a large living room and kitchen at 1417 Miller Ave, Winter Park, FL 32789
Second floor plan featuring three bedrooms, two bathrooms and a loft at 1417 Miller Ave, Winter Park, FL 32789
On Market For 65 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3312

  • Year Built

    2025

  • $/SqFt

    $483

No HOA fees and just moments from Publix, Trader Joe’s, Park Avenue, Mills/50, the Science Center, Winter Park Events Center, Advent Health and a fantastic array of restaurants and coffee shops. CORCORAN PREMIER REALTY.

Pended $610,000

Reduced By $39,000

Charming remodeled home with modern exterior and landscaped lawn at 631 Callahan St, Winter Park, FL 32789
View Details 37 Photos
Modern house exterior featuring a white facade, black accents, and a landscaped front yard at 631 Callahan St, Winter Park, FL 32789
Updated home with modern exterior and beautiful landscaping at 631 Callahan St, Winter Park, FL 32789
Charming house exterior with a lush green lawn and beautiful landscaping at 631 Callahan St, Winter Park, FL 32789
On Market For 65 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1751

  • Year Built

    1950

  • $/SqFt

    $348

Carver Town - Come see it for yourself – this is luxury living at its finest. CORCORAN PREMIER REALTY.

Home For Sale $4,500,000

Two-story brick home with dark brown accents, landscaping, and a two-car garage at 702 Via Bella, Winter Park, FL 32789
View Details 7 Photos
Brick home with herringbone driveway, landscaping, and a two-car garage at 702 Via Bella, Winter Park, FL 32789
Two-story home with a two-car garage and landscaped yard, showcasing a beautiful brick exterior at 702 Via Bella, Winter Park, FL 32789
Two-story brick home with dark brown accents, landscaping, and a two-car garage at 702 Via Bella, Winter Park, FL 32789
On Market For 67 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3720

  • Year Built

    2025

  • $/SqFt

    $1,210

The perfect home for those seeking luxurious living and refined elegance. FLORIDIAN REALTY GROUP LLC.

Pended $1,190,000

Reduced By $60,000

Charming two-story home with a large front porch and brick driveway at 567 Osceola Ave, Winter Park, FL 32789
View Details 39 Photos
Two-story home with a wrap-around porch, and manicured hedges at 567 Osceola Ave, Winter Park, FL 32789
Two-story house with a wrap-around porch and brick driveway at 567 Osceola Ave, Winter Park, FL 32789
Two-story house with a wrap-around porch and brick driveway at 567 Osceola Ave, Winter Park, FL 32789
On Market For 65 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2651

  • Year Built

    1912

  • $/SqFt

    $449

Osceola Court - Parking is easy with a circular driveway, carport and a 2-car garage with plenty of storage. Call today for an appointment! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $995,000

Reduced By $185,000

Two-story house with a blue metal roof, attached garage, and basketball hoop at 1975 Biscayne Dr, Winter Park, FL 32789
View Details 37 Photos
Two-story house with a blue metal roof and attached garage at 1975 Biscayne Dr, Winter Park, FL 32789
Open concept living room and kitchen with white sofas and modern decor at 1975 Biscayne Dr, Winter Park, FL 32789
Living room features a white sectional sofa, fireplace, and Christmas tree at 1975 Biscayne Dr, Winter Park, FL 32789
On Market For 68 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3270

  • Year Built

    2020

  • $/SqFt

    $304

Karolina On Killarney - Don’t miss your chance to own this property! SOGO REAL ESTATE SERVICES LLC.

Home For Sale $680,000

Reduced By $19,000

Charming ranch home with a two-car garage and well-manicured lawn at 1792 Killarney Dr, Winter Park, FL 32789
View Details 33 Photos
Inviting front porch with colorful seating and patterned tile at 1792 Killarney Dr, Winter Park, FL 32789
Spacious living room featuring a fireplace and mid-century modern furniture at 1792 Killarney Dr, Winter Park, FL 32789
Bright living room with a green sofa and hardwood floors at 1792 Killarney Dr, Winter Park, FL 32789
On Market For 69 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2082

  • Year Built

    1958

  • $/SqFt

    $327

Additionally, it is less than 1 mile to Trader Joe's and 1.5 miles to Park Ave. Don't miss out on this exceptional opportunity to own a piece of Winter Park paradise. THE AGENCY ORLANDO.

Home For Sale $900,000

Reduced By $39,900

Two-story house with a two-car garage and paved driveway at 675 Overspin Dr, Winter Park, FL 32789
View Details 37 Photos
Two-story house with a two-car garage and paved driveway at 675 Overspin Dr, Winter Park, FL 32789
Front entrance with arched entryway and walkway at 675 Overspin Dr, Winter Park, FL 32789
Spacious kitchen with island, stainless steel appliances, and wood cabinets at 675 Overspin Dr, Winter Park, FL 32789
On Market For 71 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2962

  • Year Built

    2010

  • $/SqFt

    $304

Dubsdread Heights - For golf enthusiasts, the prestigious Dubsdread golf course is located within a mile. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $11,900,000

Grand two-story home with gated entry and lush landscaping at 1120 Preserve Point Dr, Winter Park, FL 32789
View Details 85 Photos
Elegant home at sunset, gated entrance, palm trees at 1120 Preserve Point Dr, Winter Park, FL 32789
Stunning home with gated entry and manicured landscaping at 1120 Preserve Point Dr, Winter Park, FL 32789
Beautiful home with gated entry and manicured landscaping at 1120 Preserve Point Dr, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 79 Days

  • Bedrooms

    7

  • Full Bath(s)

    9

  • Sq. Ft.

    11255

  • Year Built

    2009

  • $/SqFt

    $1,057

With its own private gated entrance, this home is a one-of-a-kind opportunity to enjoy all of the amenities that Winter Park and Windsong have to offer. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,295,000

Reduced By $100,000

Modern two-story house with a landscaped lawn and walkway at 433 Carolina Ave, Winter Park, FL 32789
View Details 22 Photos
Spacious kitchen featuring a large island and stainless steel appliances at 433 Carolina Ave, Winter Park, FL 32789
Bright kitchen with white cabinets, quartz countertops, and a farmhouse sink at 433 Carolina Ave, Winter Park, FL 32789
Open concept kitchen with island seating and dark hardwood floors at 433 Carolina Ave, Winter Park, FL 32789
On Market For 78 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2700

  • Year Built

    2018

  • $/SqFt

    $480

Come and visit us. Welcome Home! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $1,275,000

Reduced By $20,000

Inviting front entrance with lush landscaping and double doors at 1611 Walnut Ave, Winter Park, FL 32789
View Details 41 Photos
Charming house exterior with mature trees and a brick driveway at 1611 Walnut Ave, Winter Park, FL 32789
White house exterior with lush landscaping and a stone pathway at 1611 Walnut Ave, Winter Park, FL 32789
Spacious living room featuring high ceilings, large windows, and comfortable seating at 1611 Walnut Ave, Winter Park, FL 32789
On Market For 79 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2635

  • Year Built

    1951

  • $/SqFt

    $484

Lake Knowles Terrace - Come see what could be Your next home! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $749,900

Two-story light blue house with gray accents, a fenced yard, and a brick walkway at 1521 Harmon Ave, Winter Park, FL 32789
View Details 31 Photos
Two-story light blue house with gray accents, a fenced yard, and a brick walkway at 1521 Harmon Ave, Winter Park, FL 32789
Two-story light blue house with gray accents, a fenced yard, and a brick walkway at 1521 Harmon Ave, Winter Park, FL 32789
Spacious living room with hardwood floors, a large sectional sofa, and a wooden staircase at 1521 Harmon Ave, Winter Park, FL 32789
On Market For 78 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2302

  • Year Built

    2008

  • $/SqFt

    $326

Lawndale - This exceptional home combines style, functionality, and location in one perfect package! ALL REAL ESTATE & INVESTMENTS.

Pended $365,000

Tan single-story house with a walkway and palm tree at 770 Carver St, Winter Park, FL 32789
View Details 6 Photos
Tan single-story house with a yard and palm tree at 770 Carver St, Winter Park, FL 32789
Tan single story house with a walkway and palm tree at 770 Carver St, Winter Park, FL 32789
Tan single-story house with a yard at 770 Carver St, Winter Park, FL 32789
On Market For 18 Days

  • Bedrooms

    4

  • Full Bath(s)

    1

  • Sq. Ft.

    1248

  • Year Built

    1954

  • $/SqFt

    $292

Schedule your private showing today and make your home dreams a reality! LEGENDS REALTY.

Home For Sale $5,999,999

Reduced By $250,001

Spanish style home with brick driveway, lush landscaping, and two-car garage at 541 Virginia Dr, Winter Park, FL 32789
View Details 57 Photos
Elegant Spanish-style home with a brick driveway and beautifully lit at night at 541 Virginia Dr, Winter Park, FL 32789
Stunning Spanish-style home with a brick driveway and lush landscaping at 541 Virginia Dr, Winter Park, FL 32789
Beautiful Spanish-style home with a large tree and brick driveway at 541 Virginia Dr, Winter Park, FL 32789
On Market For 82 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4725

  • Year Built

    2008

  • $/SqFt

    $1,270

Experience luxury living at its finest with unparalleled lakefront views, exceptional amenities and convenience to all the restaurants and shopping that Winter Park has to offer. HOMEVEST REALTY.

Home For Sale $1,070,000

Reduced By $30,000

Charming ranch home with mature landscaping and a two-car garage at 2330 Westminster Ct, Winter Park, FL 32789
View Details 49 Photos
White brick home with a wood front porch and a charming bench at 2330 Westminster Ct, Winter Park, FL 32789
Relaxing front porch with wooden rocking chairs and brick steps at 2330 Westminster Ct, Winter Park, FL 32789
Wood front door accented with lanterns and a brick walkway at 2330 Westminster Ct, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 84 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3296

  • Year Built

    1928

  • $/SqFt

    $325

Glencoe - Schedule your private showing today and experience the charm of Winter Park living! COMPASS FLORIDA LLC.

Home For Sale $400,000

Reduced By $25,000

Charming house with a spacious front yard and walkway at 2827 Euston Rd, Winter Park, FL 32789
View Details 30 Photos
Front porch entry with a unique swing and landscaping at 2827 Euston Rd, Winter Park, FL 32789
Bright and airy living room with hardwood floors and neutral decor at 2827 Euston Rd, Winter Park, FL 32789
Open concept living room featuring hardwood floors and ample natural light at 2827 Euston Rd, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 89 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1568

  • Year Built

    1956

  • $/SqFt

    $255

Fairbanks Shores - Conveniently located just minutes from I-4, this home offers easy access to downtown Orlando, nearby attractions, and top-rated schools. Schedule your private showing today! REGENCY REAL ESTATE LLC.

Pended $2,300,000

Luxury home with pool and lakefront access at 1032 Early Ave, Winter Park, FL 32789
View Details 73 Photos
Luxury lakefront home nestled amongst lush trees at 1032 Early Ave, Winter Park, FL 32789
Stone driveway leading to a beautiful home at 1032 Early Ave, Winter Park, FL 32789
Lakefront property with expansive wooded area at 1032 Early Ave, Winter Park, FL 32789
On Market For 66 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2894

  • Year Built

    1999

  • $/SqFt

    $795

Buyers And Their Agents Must Verify All Information That Is Important To Them. KINCAID REALTY.

Home For Sale $449,990

Reduced By $10,000

Charming light blue house with a white porch and landscaped yard at 1550 Indiana Ave, Winter Park, FL 32789
View Details 33 Photos
Quaint light blue house with a white porch and lush green lawn at 1550 Indiana Ave, Winter Park, FL 32789
Relaxing front porch with rocking chairs and a porch swing at 1550 Indiana Ave, Winter Park, FL 32789
Inviting front porch with rocking chairs and a porch swing at 1550 Indiana Ave, Winter Park, FL 32789
On Market For 93 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1032

  • Year Built

    1950

  • $/SqFt

    $436

Lawndale - Perfect as a cozy retreat or an exceptional investment opportunity in a prime location. TALENT REALTY SOLUTIONS.

Home For Sale $2,000,000

Two-story home with modern design, two-car garage, and palm trees at 2260 Mulbry Dr, Winter Park, FL 32789
View Details 4 Photos
Two-story home floor plan showcasing five bedrooms, a large gathering room, and a two-car garage at 2260 Mulbry Dr, Winter Park, FL 32789
First-floor plan with open concept kitchen, gathering room, and two-car garage at 2260 Mulbry Dr, Winter Park, FL 32789
Second floor plan featuring three bedrooms, a loft, and two bathrooms at 2260 Mulbry Dr, Winter Park, FL 32789
On Market For 104 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3246

  • Year Built

    2025

  • $/SqFt

    $616

Lake Forest Park - Zoned for top-rated schools, this is your opportunity to build your dream Oasis and enjoy the Florida lifestyle! KELLER WILLIAMS WINTER PARK.

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 110 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 113 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 $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 121 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 123 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 $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 131 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.

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