242 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $1,350,000

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 Today
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2652

  • Year Built

    1948

  • $/SqFt

    $509

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

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 Today
  • 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

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 5 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

On Market For 5 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2916

  • Year Built

    1973

  • $/SqFt

    $444

Lake Knowles Terrace - Owner put a lot of special touches to this home.Office is not separate it is the extra space in the master. PARK AVENUE REALTY LLC.

Home For Sale $449,990

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 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1326

  • Year Built

    1971

  • $/SqFt

    $339

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

Home For Sale $399,900

Charming single-story home featuring a well-maintained yard and attached one-car garage at 5055 Lake Howell Rd, Winter Park, FL 32792
Spacious living room with arched entryway, a decorative fireplace, and new gray wood-look floors at 5055 Lake Howell Rd, Winter Park, FL 32792
Bright living room with a fireplace and new gray wood-look flooring at 5055 Lake Howell Rd, Winter Park, FL 32792
On Market For 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1381

  • Year Built

    1957

  • $/SqFt

    $290

Tanglewood - Newer A/C unit and water heater. SPECTRUM PROPERTY GROUP LLC.

Home For Sale $1,595,000

Charming pink home featuring stately white columns, a landscaped front yard, and tropical palm trees at 335 Beloit Ave, Winter Park, FL 32789
Welcoming foyer with neutral tile floors and chic decor that flows into the spacious living area at 335 Beloit Ave, Winter Park, FL 32789
Bright living room with a decorative fireplace, modern furnishings, and access to outdoor living space at 335 Beloit Ave, Winter Park, FL 32789
On Market For 6 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

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 5 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2703

  • Year Built

    1967

  • $/SqFt

    $442

Winter Park Heights - Just minutes from the shopping and dining district of Park Avenue in downtown Winter Park, this remarkable home offers the ideal blend of comfort, convenience and style. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $819,000

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 6 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1961

  • $/SqFt

    $448

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 $795,000

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 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1101

  • Year Built

    1960

  • $/SqFt

    $722

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

Home For Sale $480,000

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 6 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1572

  • Year Built

    1973

  • $/SqFt

    $305

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

Home For Sale $430,000

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 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1581

  • Year Built

    1970

  • $/SqFt

    $272

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

Home For Sale $425,000

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 6 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 $1,250,000

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 4 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2220

  • Year Built

    1959

  • $/SqFt

    $563

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

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 7 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.

Home For Sale $499,900

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 7 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.

Pended $474,000

Charming single-story home featuring a well-manicured front yard with rainbow in the distance at 236 N Ranger Blvd, Winter Park, FL 32792
Inviting home featuring a neatly landscaped yard and a walkway to the front door at 236 N Ranger Blvd, Winter Park, FL 32792
Inviting home featuring a neatly landscaped walkway to the front door and bench at 236 N Ranger Blvd, Winter Park, FL 32792
On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1844

  • Year Built

    1963

  • $/SqFt

    $257

Don’t miss the opportunity to make 236 North Ranger Boulevard your own, schedule a showing today! FOLIO REALTY LLC.

Home For Sale $293,000

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 8 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1187

  • Year Built

    1994

  • $/SqFt

    $247

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

Home For Sale $2,395,000

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 7 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 $825,000

Reduced By $74,000

Single-story home with a carport and a tidy front lawn offers curb appeal at 1811 Oneco Ave, Winter Park, FL 32789
Aerial view of a home with a large, private backyard oasis and lush greenery at 1811 Oneco Ave, Winter Park, FL 32789
Aerial view of a home nestled in a tranquil neighborhood surrounded by mature trees at 1811 Oneco Ave, Winter Park, FL 32789
On Market For 8 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1348

  • Year Built

    1972

  • $/SqFt

    $612

Flora Park - Great Wp Schools. Survey Available In Attachments. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $690,000

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 9 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
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
On Market For 10 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.

Home For Sale $425,000

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 8 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 $399,900

Beautifully landscaped front yard with colorful flowers and lush greenery enhancing the curb appeal of this lovely home at 3354 Hamlet Loop, Winter Park, FL 32792
Spacious living room featuring new grey tone vinyl floors, a comfortable sectional couch and a sleek ceiling fan at 3354 Hamlet Loop, Winter Park, FL 32792
Bright and spacious living room boasts grey tone vinyl floors, recessed lighting, and a comfortable sectional couch at 3354 Hamlet Loop, Winter Park, FL 32792
On Market For 10 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1533

  • Year Built

    1993

  • $/SqFt

    $261

Villas Of Casselberry - Homes like this are rarely available—schedule your private tour today before it’s gone! CHARLES RUTENBERG REALTY ORLANDO.

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
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 12 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 $569,500

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 11 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2213

  • Year Built

    1984

  • $/SqFt

    $257

Amberwood - **2018 ROOF, 2021 AC Condenser, 2019 Water Heater** OLYMPUS EXECUTIVE REALTY INC.

Home For Sale $534,900

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 13 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 $492,000

Reduced By $14,000

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 14 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 $450,000

Attractive two-story home with green lawn, mature trees, and an attached two-car garage in a desirable location at 8413 Commander Cv, Winter Park, FL 32792
A charming home is viewed from under the branches of a large, mature tree with a wooden swing at 8413 Commander Cv, Winter Park, FL 32792
Inviting two-story home featuring manicured lawn, mature trees, and an attached two-car garage in a desirable neighborhood at 8413 Commander Cv, Winter Park, FL 32792
On Market For 14 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1634

  • Year Built

    1985

  • $/SqFt

    $275

Don’t miss the opportunity to call this beautiful Trinity Bay property your home—schedule your private tour today! CREEGAN GROUP.

Home For Sale $430,000

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 14 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1327

  • Year Built

    1965

  • $/SqFt

    $324

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

Pended $3,295,000

White two-story house with a three-car garage and manicured lawn at 100 E Rockwood Way, Winter Park, FL 32789
Two-story white house with black accents and a walkway to the front door at 100 E Rockwood Way, Winter Park, FL 32789
Bright and spacious entryway with elegant staircase and hardwood floors at 100 E Rockwood Way, Winter Park, FL 32789
On Market For 13 Days
  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    4304

  • Year Built

    2020

  • $/SqFt

    $766

Charmont - A rare opportunity to own a turnkey masterpiece that offers the ideal balance of comfort style, and exceptional entertainment spaces. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,950,000

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 16 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

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 16 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1910

  • Year Built

    1966

  • $/SqFt

    $256

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

Home For Sale $485,000

Newly renovated home with blue exterior, white garage door, and landscaping at 7104 Wrenwood Way, Winter Park, FL 32792
Newly renovated home with blue exterior, white garage door, and landscaping at 7104 Wrenwood Way, Winter Park, FL 32792
Dark blue front door with sidelights, enhancing curb appeal at 7104 Wrenwood Way, Winter Park, FL 32792
On Market For 15 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1778

  • Year Built

    1974

  • $/SqFt

    $273

Wrenwood Heights - Home is under video and audio surveillance. KELLER WILLIAMS ADVANTAGE REAL.

Pended $3,130,000

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 $1,995,000

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 16 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3971

  • Year Built

    1990

  • $/SqFt

    $502

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

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 19 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

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 19 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    2964

  • Year Built

    2025

  • $/SqFt

    $715

Comstock Park - Conveniently located just 1.9 miles or 8 minutes from the vibrant Park Avenue, you'll have easy access to boutique shopping and fine dining. Call today for more information. COMPASS FLORIDA, LLC.

Pended $2,100,000

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 19 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 $1,950,000

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
On Market For 19 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4227

  • Year Built

    2003

  • $/SqFt

    $461

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

Home For Sale $499,000

Inviting front entry with a charming stone pathway and landscaping at 2247 King Edwards Ct, Winter Park, FL 32792
Bright hallway with hardwood floors and access to other rooms at 2247 King Edwards Ct, Winter Park, FL 32792
Spacious living room showcasing hardwood floors and a ceiling fan at 2247 King Edwards Ct, Winter Park, FL 32792
On Market For 20 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2129

  • Year Built

    1968

  • $/SqFt

    $234

Winter Woods - Schedule your private showing today, take the opportunity to own a piece of Winter Park Paradise in the desirable Sunshine State! EMPIRE NETWORK REALTY.

Pended $1,750,000

Three-car garage with paver driveway and stone accents at 2185 Talman Court, Winter Park, FL 32792
Beautiful two-story home with stone and stucco exterior at 2185 Talman Court, Winter Park, FL 32792
Grand home with stone and stucco exterior, landscaped yard at 2185 Talman Court, Winter Park, FL 32792
On Market For 6 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4760

  • Year Built

    2008

  • $/SqFt

    $368

Additional highlights include a generator, outdoor shower, zoned AC, tankless water heaters, Lutron light control system, AC Nest control system, outdoor security cameras, Lightening protection, and a spacious three-car side/rear-entry garage. WELCOME HOME! FANNIE HILLMAN & ASSOCIATES.

Pended $1,175,000

Two-story house with a wrap-around porch and large windows at 3818 Kinsley Place, Winter Park, FL 32792
Two-story house with a wrap-around porch and large windows at 3818 Kinsley Place, Winter Park, FL 32792
Two-story house with a wrap-around porch and large windows at 3818 Kinsley Place, Winter Park, FL 32792
On Market For 19 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3613

  • Year Built

    1989

  • $/SqFt

    $325

Bear Gully Bay - Enjoy lakefront living at its finest, with direct access to Bear Gully Lake for boating, fishing, skiing or simply enjoying the view from the backyard. PREMIER SOTHEBY'S INTL. REALTY.

Pended $434,900

House exterior showcasing a well-maintained lawn and blue garage door at dusk at 2076 Leanne Ct, Winter Park, FL 32792
Brick walkway leading to the front door of a renovated house at 2076 Leanne Ct, Winter Park, FL 32792
Light-filled dining area with laminate wood floors and kitchen access at 2076 Leanne Ct, Winter Park, FL 32792
On Market For 20 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1729

  • Year Built

    1969

  • $/SqFt

    $252

Eastbrook - Schedule a tour today—your dream home awaits! SAND DOLLAR REALTY GROUP INC.

Home For Sale $399,900

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 21 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1408

  • Year Built

    1986

  • $/SqFt

    $284

STRICKLAND REALTY GROUP INC.

Home For Sale $399,000

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 21 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1397

  • Year Built

    1994

  • $/SqFt

    $286

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

Home For Sale $389,900

Reduced By $9,100

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 21 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 $1,380,000

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 21 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 $575,000

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 21 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1579

  • Year Built

    1962

  • $/SqFt

    $364

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 $550,000

Reduced By $35,000

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 21 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1688

  • Year Built

    1965

  • $/SqFt

    $326

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.

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 407-967-1435 and speak with one of our real estate consultants.

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