274 Results

View 274 Winter Park Florida Homes for Sale

Home For Sale $1,275,000

Modern home with a white exterior, complemented by a brick driveway and lush landscaping at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
View Details 49 Photos
Modern home with white exterior, complemented by a brick driveway and manicured landscaping at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
Aerial view of a modern white home near a golf course with mature landscaping at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
Bright open-concept living room with modern furnishings flowing into a stylish kitchen at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 33 Days

  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2284

  • Year Built

    2015

  • $/SqFt

    $558

Don’t miss your chance to own this exceptional property in one of Winter Park’s most sought-after locations. Schedule your private showing today! RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $750,000

Contemporary home with a manicured yard and a stylish driveway providing ample parking at 726 N Pennsylvania Ave, Winter Park, FL 32789
View Details 30 Photos
Aerial view of modern home adjacent to a lush golf course and featuring ample parking at 726 N Pennsylvania Ave, Winter Park, FL 32789
Modern kitchen featuring stainless steel appliances, a black marble backsplash and a stylish breakfast bar at 726 N Pennsylvania Ave, Winter Park, FL 32789
Contemporary kitchen with stainless steel appliances, sleek black cabinetry and tiled flooring at 726 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 33 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1167

  • Year Built

    2015

  • $/SqFt

    $643

Don’t miss this incredible opportunity in one of Winter Park’s most sought-after locations, Schedule your private showing today! RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $550,000

Stylish modern home with a geometric design, white exterior, brick driveway, and manicured front yard hedge at 720 N Pennsylvania Ave, Winter Park, FL 32789
View Details 26 Photos
A scenic aerial view of a modern home with a golf course, railroad, and lush greenery in the neighborhood at 720 N Pennsylvania Ave, Winter Park, FL 32789
Open-concept living room with modern furniture, a ceiling fan, and an open view into the modern kitchen at 720 N Pennsylvania Ave, Winter Park, FL 32789
Bright living room with wood-look tile flooring, neutral sofa, pops of color, and contemporary decor at 720 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 33 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1115

  • Year Built

    2015

  • $/SqFt

    $493

Don’t miss this chance to own a modern, stylish home in the heart of Winter Park! Schedule your private showing today. RE/MAX TOWN & COUNTRY REALTY.

Pended $539,990

Reduced By $10,010

Charming two-story home with a covered front porch and blue exterior and well manicured landscaping at 423 Ololu Dr, Winter Park, FL 32789
View Details 24 Photos
A bright and inviting blue home, showcasing a large covered porch and outdoor features at 423 Ololu Dr, Winter Park, FL 32789
A bright entryway features wood-look tile flooring, fresh paint and modern light fixture at 423 Ololu Dr, Winter Park, FL 32789
Modern kitchen featuring quartz countertops, new stainless steel appliances, and stylish pendant lighting at 423 Ololu Dr, Winter Park, FL 32789
On Market For 33 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1920

  • Year Built

    1981

  • $/SqFt

    $281

Contact us today for a private showing. AAA GLOBAL VENTURES PA.

Pended $399,900

Charming home with a carport and a beautifully landscaped front yard with lush green grass at 767 Baffie Ave, Winter Park, FL 32789
View Details 25 Photos
Eat-in kitchen featuring white cabinets, an island, terracotta tile floors, and views of the backyard at 767 Baffie Ave, Winter Park, FL 32789
Spacious kitchen with terracotta tile floors, white cabinetry, black appliances, and a door to the backyard at 767 Baffie Ave, Winter Park, FL 32789
Bright dining area with terracotta tile floors, a round table, and a large window with views of the yard at 767 Baffie Ave, Winter Park, FL 32789
On Market For 33 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1132

  • Year Built

    1958

  • $/SqFt

    $353

Combining the perfect blend of modern updates and original character, this home is a must-see in the heart of Winter Park! GECKO REALTY, INC.

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 34 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 $749,000

A stunning aerial view of a home with a long driveway, surrounded by lush trees on a spacious lot at 5150 Old Howell Branch Rd, Winter Park, FL 32792
View Details 38 Photos
An aerial view showcases the home's location near a road and the surrounding neighborhood at 5150 Old Howell Branch Rd, Winter Park, FL 32792
Charming single-story brick home featuring an attached garage and well-maintained lawn at 5150 Old Howell Branch Rd, Winter Park, FL 32792
A bright, modern living room with stylish furniture, sleek flooring, and neutral decor at 5150 Old Howell Branch Rd, Winter Park, FL 32792
On Market For 34 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    2108

  • Year Built

    1964

  • $/SqFt

    $355

This property is perfect for businesses seeking high visibility and accessibility, with excellent potential for various uses and expansion. COMPASS FLORIDA, 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 37 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 37 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.

Home For Sale $439,990

Reduced By $10,000

Charming single-story home with a two-car garage and a well-maintained front yard at 7427 Houston E Ct, Winter Park, FL 32792
View Details 24 Photos
Charming single-story home with a two-car garage and a well-maintained front yard at 7427 Houston E Ct, Winter Park, FL 32792
Charming single-story home with a two-car garage and a well-maintained front yard at 7427 Houston E Ct, Winter Park, FL 32792
Inviting front entry with decorative door, adjacent window, and clean landscaping at 7427 Houston E Ct, Winter Park, FL 32792
On Market For 37 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1326

  • Year Built

    1971

  • $/SqFt

    $332

Woodcrest - Schedule your visit today and come see why this should be your next home. FUTURE HOME REALTY INC.

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 26 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 38 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 $795,000

Reduced By $24,000

Charming single-story home with well-manicured lawn, mature tree, and brick-paved driveway at 625 Brechin Dr, Winter Park, FL 32792
View Details 42 Photos
Inviting home showcasing a brick driveway leading to an attached garage and landscaped front yard at 625 Brechin Dr, Winter Park, FL 32792
Close-up of the brick-paved entryway with decorative columns and trimmed hedges at 625 Brechin Dr, Winter Park, FL 32792
Bright and airy living room featuring hardwood floors and a doorway to another room at 625 Brechin Dr, Winter Park, FL 32792
On Market For 38 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1961

  • $/SqFt

    $435

Located in one of Winter Park’s most adored communities, residences of Kenilworth Shores are zoned for the highly desirable Brookshire Elementary/Glenridge Middle/Winter Park High school district and are just a few minutes away from the Park Avenue shopping and dining district, Rollins College, Advent Health, Baldwin Park, and more. KELLY PRICE & COMPANY LLC.

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 37 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.

Home For Sale $469,900

Reduced By $10,100

Charming one-story home featuring a brick facade, well-maintained lawn, and a welcoming red front door at 5359 Lanyard Ct, Winter Park, FL 32792
View Details 31 Photos
Well-manicured lawn and lush landscaping surround this single story home with an attached garage at 5359 Lanyard Ct, Winter Park, FL 32792
Charming one-story home featuring a brick facade, well-maintained lawn, and a welcoming red front door at 5359 Lanyard Ct, Winter Park, FL 32792
Warm and inviting foyer with neutral tile flooring, red accent wall, and decorative touches at 5359 Lanyard Ct, Winter Park, FL 32792
On Market For 38 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1572

  • Year Built

    1973

  • $/SqFt

    $299

Woodcrest - This home is a rare gem for first-time buyers or anyone looking for a stress-free, move-in-ready home. REDFIN CORPORATION.

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 38 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 $419,000

Reduced By $11,000

Charming single-story home featuring a well-maintained lawn, dark garage door, and welcoming curb appeal at 7331 Blue Jacket W Pl, Winter Park, FL 32792
View Details 43 Photos
Bright, open-concept kitchen with white cabinets, stainless steel appliances, and a breakfast bar overlooking the living area at 7331 Blue Jacket W Pl, Winter Park, FL 32792
Open-concept living area with stylish flooring, modern lighting, and an abundance of natural light at 7331 Blue Jacket W Pl, Winter Park, FL 32792
Modern kitchen featuring stainless steel appliances, a sleek backsplash, and a breakfast bar with pendant lighting at 7331 Blue Jacket W Pl, Winter Park, FL 32792
On Market For 38 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1581

  • Year Built

    1970

  • $/SqFt

    $265

Woodcrest - Don’t miss your chance to make this move-in ready gem your new home! NETWORTH REALTY OF ORLANDO, LLC.

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 36 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.

Pended $949,900

Charming home with a well-manicured lawn, lush landscaping, and a welcoming two-car garage at 533 Balmoral Rd, Winter Park, FL 32789
View Details 39 Photos
Inviting front entrance with a lush, verdant pergola, and a security system at 533 Balmoral Rd, Winter Park, FL 32789
Up-close view of a stunning wooden front door surrounded by lush greenery and stone accents at 533 Balmoral Rd, Winter Park, FL 32789
Cozy covered patio featuring wood-look tile flooring, a unique chair, and ample natural light at 533 Balmoral Rd, Winter Park, FL 32789
On Market For 39 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1900

  • Year Built

    1957

  • $/SqFt

    $500

Upgrades include: New Paint & Finishes, Modernized Bathrooms (New vanities and a renovated master shower) Custom Master Closet, New Interior Doors and windows, New Upgraded HVAC System (2021), Tankless gas hot water heater, Roof (2020), HVAC (2021) Exterior Stone Façade, Updated Landscaping & Outdoor Living spaces (Lanai, pergola, and firepit) irrigation, New Front Door & Exterior Lighting, Solar Panels (paid off) Security System Ready (Wired for easy setup) Upgraded Laundry Room (Added storage, tile, and cabinetry) CHARLES RUTENBERG REALTY ORLANDO.

Pended $499,900

Charming two-story home featuring a red brick facade and a two-car garage at 4309 Enright Ct, Winter Park, FL 32792
View Details 36 Photos
A charming two-story home with a red brick facade, a two-car garage, and mature trees at 4309 Enright Ct, Winter Park, FL 32792
Inviting front porch leading to a well-maintained home with a classic brick accent wall at 4309 Enright Ct, Winter Park, FL 32792
Bright living room with a white brick fireplace, large windows, and hardwood floors at 4309 Enright Ct, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 37 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2204

  • Year Built

    1985

  • $/SqFt

    $227

Seize the opportunity to own this charming home and start creating unforgettable memories in a space that truly feels like yours. BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY.

Home For Sale $284,000

Reduced By $9,000

Charming single-story home with a well-manicured lawn and inviting curb appeal at 1727 Winter Green Blvd, Winter Park, FL 32792
View Details 18 Photos
Bright living room with large arched window, neutral decor, and wood-look floors showcasing a comfortable and inviting space at 1727 Winter Green Blvd, Winter Park, FL 32792
Spacious living room with a large window, plenty of sunlight, and wood floors at 1727 Winter Green Blvd, Winter Park, FL 32792
Well-lit kitchen featuring granite countertops, stainless steel appliances, and white cabinetry at 1727 Winter Green Blvd, Winter Park, FL 32792
On Market For 40 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1187

  • Year Built

    1994

  • $/SqFt

    $239

Winter Green - Like what you hear? Come see it for yourself! OPENDOOR BROKERAGE LLC.

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 40 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.

Home For Sale $690,000

Charming two-story home featuring a well-manicured front yard, brick driveway and attached two car garage at 1219 Verdant Glade Pl, Winter Park, FL 32792
View Details 45 Photos
A beautiful home with a brick driveway, two-car garage, and landscaped front yard is seen on a bright sunny day at 1219 Verdant Glade Pl, Winter Park, FL 32792
Inviting front entrance with a brick walkway, lush landscaping, and a welcoming covered porch at 1219 Verdant Glade Pl, Winter Park, FL 32792
Bright foyer featuring tile floors, staircase with iron railing, and an open doorway to the outside at 1219 Verdant Glade Pl, Winter Park, FL 32792
On Market For 41 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2002

  • Year Built

    2019

  • $/SqFt

    $345

Meadows At Hawks Crest - Don't miss out on this exceptional Winter Park home offering luxury, convenience, and a serene setting. FORTUNE INTERNATIONAL REALTY.

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 42 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 $425,000

Charming single-story home featuring blue shutters, a well-manicured lawn, and attached two-car garage at 2642 Tierra Cir, Winter Park, FL 32792
View Details 19 Photos
Close up of the home's front door with brick flooring, white pillars and blue shutters on the front windows at 2642 Tierra Cir, Winter Park, FL 32792
Spacious living room with parquet floors, decorative chandelier, and large windows that provide ample natural light at 2642 Tierra Cir, Winter Park, FL 32792
Open-concept living area features parquet floors, a chandelier and a clear view into the adjacent kitchen space at 2642 Tierra Cir, Winter Park, FL 32792
On Market For 34 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1715

  • Year Built

    1969

  • $/SqFt

    $248

Casa Aloma - The home is in an excellent location, backing to Interlachen Country Club, near the Lakemont YMCA, and with easy access to downtown Winter Park and Maitland. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $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 45 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 $559,000

Reduced By $10,500

Modern two-story home with gray siding, manicured landscaping, and a welcoming walkway to the front door at 3901 Woodglade Cv, Winter Park, FL 32792
View Details 44 Photos
Charming two-story home with gray siding, three-car garage, and lush lawn at 3901 Woodglade Cv, Winter Park, FL 32792
First-floor floor plan showing primary bedroom, kitchen, living room, and bathroom layout at 3901 Woodglade Cv, Winter Park, FL 32792
Second-floor floor plan showcasing bedrooms, flex space, and bathroom at 3901 Woodglade Cv, Winter Park, FL 32792
On Market For 45 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2213

  • Year Built

    1984

  • $/SqFt

    $253

Amberwood - Don’t miss this opportunity for a one-of-a-kind gem at an unbeatable price—schedule your showing today! OLYMPUS EXECUTIVE REALTY INC.

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 45 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.

Pended $492,000

Reduced By $14,000

Charming single-story home with manicured lawn and neutral-toned exterior at 3447 Astoria Ct, Winter Park, FL 32792
View Details 26 Photos
Bright living room boasts wood floors, modern furniture, and a cozy atmosphere, perfect for relaxing or entertaining guests at 3447 Astoria Ct, Winter Park, FL 32792
Spacious living room with wood-look floors, neutral walls, and recessed lighting at 3447 Astoria Ct, Winter Park, FL 32792
Cozy main bedroom with tray ceiling, large window, and elegant furnishings at 3447 Astoria Ct, Winter Park, FL 32792
On Market For 46 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1750

  • Year Built

    2018

  • $/SqFt

    $281

Eastbrook - Like what you hear? Come see it for yourself! OPENDOOR BROKERAGE LLC.

Home For Sale $419,900

Reduced By $10,100

Charming single-story home with a well-manicured lawn, solar panels and a one car garage at 927 Mare Bello Dr, Winter Park, FL 32792
View Details 22 Photos
Aerial view showcasing home with solar panels and a private pool nestled in a fenced backyard at 927 Mare Bello Dr, Winter Park, FL 32792
Charming one-story home featuring solar panels, an attached garage and a cozy front yard at 927 Mare Bello Dr, Winter Park, FL 32792
Aerial view showcasing the home's layout, solar panels, a private pool, and fenced yard at 927 Mare Bello Dr, Winter Park, FL 32792
On Market For 46 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1327

  • Year Built

    1965

  • $/SqFt

    $316

Experience the perfect blend of modern amenities and prime location at 927 Mare Bello Drive. LA ROSA REALTY KISSIMMEE.

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 48 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.

Home For Sale $489,900

Ranch-style home with attached garage and mature landscaping at 3458 Balsam Dr, Winter Park, FL 32792
View Details 12 Photos
Inviting rectangular pool with light-colored stone decking at 3458 Balsam Dr, Winter Park, FL 32792
Refreshing blue rectangular pool, surrounded by lush greenery at 3458 Balsam Dr, Winter Park, FL 32792
Relaxing blue rectangular pool with stone deck and surrounding trees at 3458 Balsam Dr, Winter Park, FL 32792
On Market For 48 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1910

  • Year Built

    1966

  • $/SqFt

    $256

Eastbrook - Come see what this amazing community and home has to offer. CENTURY 21 BE3.

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 17 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 49 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 51 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 5 Photos
Modern kitchen with white cabinets, a large island, and stainless steel appliances at 785 N Phelps Ave, Winter Park, FL 32789
Spacious living area featuring a sectional sofa and a large TV at 785 N Phelps Ave, Winter Park, FL 32789
Bright bedroom with a comfortable bed and access to the backyard at 785 N Phelps Ave, Winter Park, FL 32789
On Market For 51 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.

Pended $2,100,000

Brick house with a metal roof, lush landscaping, and a brick walkway at 140 Dana Way, Winter Park, FL 32789
View Details 46 Photos
Brick walkway, lush landscaping and a charming house exterior at 140 Dana Way, Winter Park, FL 32789
Brick house with metal roof, landscaping, and a gravel driveway at 140 Dana Way, Winter Park, FL 32789
Housetop view showing the home's size and lot in a wooded area at 140 Dana Way, Winter Park, FL 32789
On Market For 51 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    3441

  • Year Built

    2011

  • $/SqFt

    $610

Charmont - The gated driveway and fully fenced property ensure security and exclusivity, all within one of Winter Park’s most sought-after neighborhoods.This is a rare opportunity to own a luxurious estate in a prestigious Winter Park location, surrounded by the beauty of the Lake Sue neighborhodd and just moments from the best shopping, dining, and cultural experiences the area has to offer. OLDE TOWN BROKERS INC.

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 52 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 $399,900

House exterior with a two car garage and landscaping at 3131 Ash Park Loop, Winter Park, FL 32792
View Details 72 Photos
Aerial view of a house and surrounding neighborhood at 3131 Ash Park Loop, Winter Park, FL 32792
House exterior featuring a two-car garage and landscaping at 3131 Ash Park Loop, Winter Park, FL 32792
Brick home with a red front door and covered porch at 3131 Ash Park Loop, Winter Park, FL 32792
On Market For 53 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1408

  • Year Built

    1986

  • $/SqFt

    $284

STRICKLAND REALTY GROUP INC.

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 46 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.

Pended $385,000

Reduced By $14,000

Cute one-story home with a red door and well-manicured lawn at 3377 Hamlet Loop, Winter Park, FL 32792
View Details 28 Photos
Idyllic lake view with wooden dock and gazebo in a lush green landscape at 3377 Hamlet Loop, Winter Park, FL 32792
Sparkling community pool surrounded by lounge chairs and lush landscaping at 3377 Hamlet Loop, Winter Park, FL 32792
Cozy living room featuring a fireplace, vaulted ceilings, and comfortable seating at 3377 Hamlet Loop, Winter Park, FL 32792
On Market For 52 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1397

  • Year Built

    1994

  • $/SqFt

    $276

Villas Of Casselberry - Brand New Roof - 2024, Hvac - 2024, Water Heater - 2017. KELLER WILLIAMS WINTER PARK.

Home For Sale $1,380,000

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 53 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2060

  • Year Built

    1962

  • $/SqFt

    $670

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

Home For Sale $569,000

Reduced By $6,000

White house with black garage door, landscaping, and long driveway at 2779 Prince John Rd, Winter Park, FL 32792
View Details 36 Photos
Teal front door and whitewashed brick exterior at 2779 Prince John Rd, Winter Park, FL 32792
Bright living room with hardwood floors and modern furniture at 2779 Prince John Rd, Winter Park, FL 32792
Cozy sitting area with two armchairs and a brown ottoman at 2779 Prince John Rd, Winter Park, FL 32792
On Market For 53 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1579

  • Year Built

    1962

  • $/SqFt

    $360

With its ideal blend of interior luxury and expansive outdoor living, it’s the perfect place to call home. HVAC - 2023, ROOF - 2022 KELLER WILLIAMS WINTER PARK.

Home For Sale $535,000

Reduced By $50,000

Ranch style home with gray exterior, landscaped lawn, and attached garage at 2823 Cady Way, Winter Park, FL 32792
View Details 26 Photos
Living room with hardwood floors, leather couches, and a large piece of art at 2823 Cady Way, Winter Park, FL 32792
Bright living room with hardwood floors, leather furniture, and view into dining room at 2823 Cady Way, Winter Park, FL 32792
Living room with hardwood floors, access to screened patio, and built-in shelving at 2823 Cady Way, Winter Park, FL 32792
On Market For 52 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1688

  • Year Built

    1965

  • $/SqFt

    $317

Easy access to Winter Park shopping, dining and restaurants as well as the Orlando International airport, UCF and Rollins college. Schedule your showing today! COLDWELL BANKER RESIDENTIAL RE.

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 53 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.

Pended $1,299,990

Aerial view of a single story home with a pool and large backyard at 2258 E Howard Dr, Winter Park, FL 32789
View Details 48 Photos
Modern single story home with attached garage and landscaped lawn at 2258 E Howard Dr, Winter Park, FL 32789
Updated mid century modern home with attached garage and lush landscaping at 2258 E Howard Dr, Winter Park, FL 32789
Modern garage with white door and wood-like accents at 2258 E Howard Dr, Winter Park, FL 32789
On Market For 48 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2747

  • Year Built

    1953

  • $/SqFt

    $473

Northwood Terrace - Zoned for top-rated Audubon K-8 and Winter Park High School, this neighborhood is a true gem, benefiting from its prime location and excellent schools, in an area experiencing rapid transformation. NAIM REAL ESTATE LLC.

Home For Sale $459,900

Reduced By $19,100

Charming single-story home featuring a well-manicured lawn and a welcoming front porch with brick accents at 2207 Winter Woods Blvd, Winter Park, FL 32792
View Details 40 Photos
Attractive home exterior showcases a brick pathway leading to the front door, complemented by green landscaping at 2207 Winter Woods Blvd, Winter Park, FL 32792
Bird's eye view of single-Gathering home and neighborhood at 2207 Winter Woods Blvd, Winter Park, FL 32792
Charming front door with decorative details and a welcoming porch light at 2207 Winter Woods Blvd, Winter Park, FL 32792
On Market For 53 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1710

  • Year Built

    1969

  • $/SqFt

    $269

Winter Woods - The perfect blend of space, convenience, and flexibility—a true must-see. Schedule your private showing today! COLDWELL BANKER REALTY.

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 55 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 21 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 59 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.

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