337 Results

View 337 Winter Park Florida Homes for Sale

Pended $2,349,900

Reduced By $150,000

Beautiful backyard with a sparkling pool, outdoor seating, and lush green lawn at 301 Rippling Ln, Winter Park, FL 32789
Stunning waterfront home with a private boat dock and lift, lush landscaping, and a sparkling pool at 301 Rippling Ln, Winter Park, FL 32789
Spacious tiled patio with folding glass doors, a pool, and comfortable outdoor seating at 301 Rippling Ln, Winter Park, FL 32789
On Market For 114 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3694

  • Year Built

    1958

  • $/SqFt

    $636

Contact us today to schedule a private tour. XCLUSIVE HOMES LLC.

Home For Sale $1,275,000

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 116 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

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 116 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

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 116 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.

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 For 117 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

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 120 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

Cozy backyard with pergola creates an inviting outdoor space for relaxing and entertaining surrounded by lush landscape at 1611 Chestnut Ave, Winter Park, FL 32789
Inviting entryway boasts wood-look floors, a red front door, coat rack with storage and a wooden accent table at 1611 Chestnut Ave, Winter Park, FL 32789
Dining room with farmhouse table, barn door, hardwood floors, and designer wallpaper and paint at 1611 Chestnut Ave, Winter Park, FL 32789
On Market For 120 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 $1,125,000

Reduced By $70,000

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
Bright foyer with dark wood door, travertine floors, white pillars, arches and natural light from black-framed windows at 1690 Oneco Ave, Winter Park, FL 32789
On Market For 121 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2703

  • Year Built

    1967

  • $/SqFt

    $416

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

Home For Sale $795,000

Reduced By $24,000

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 121 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.

Pended $449,900

Reduced By $30,100

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 118 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1572

  • Year Built

    1973

  • $/SqFt

    $286

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 $2,389,000

Reduced By $6,000

Modern two-story home featuring a two-car garage, balcony and sportscars in the driveway at 2412 Chantilly Ave, Winter Park, FL 32789
Modern two-story home featuring a two-car garage, balcony and sleek curb appeal at 2412 Chantilly Ave, Winter Park, FL 32789
Modern pool area with covered patio, large sliding glass doors and manicured lawn at 2412 Chantilly Ave, Winter Park, FL 32789
On Market For 109 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4506

  • Year Built

    2024

  • $/SqFt

    $530

Winter Park Village - It’s a masterpiece. Schedule your private tour today. COMPASS FLORIDA LLC.

Home For Sale $549,000

Reduced By $20,500

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 128 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2213

  • Year Built

    1984

  • $/SqFt

    $248

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 $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 131 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 $435,000

Reduced By $54,900

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 131 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1910

  • Year Built

    1966

  • $/SqFt

    $228

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

Home For Sale $1,795,000

Reduced By $200,000

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 121 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3971

  • Year Built

    1990

  • $/SqFt

    $452

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 $2,119,000

Two-story home under construction featuring zip system sheathing and concrete block walls on a sunny day at 785 N Phelps Ave, Winter Park, FL 32789
Modern kitchen features white cabinets, stainless steel appliances, a large island, and bar stool seating at 785 N Phelps Ave, Winter Park, FL 32789
Spacious garage under construction features block walls, wooden ceiling joists, and window openings offering natural light at 785 N Phelps Ave, Winter Park, FL 32789
On Market For 134 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 $349,000

Reduced By $50,900

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 134 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1408

  • Year Built

    1986

  • $/SqFt

    $248

With its superb location and promising features, 3131 Ash Park Loop is an ideal choice for anyone looking to invest in a property with both immediate appeal and long-term value. STRICKLAND REALTY GROUP INC.

Home For Sale $1,300,000

Reduced By $80,000

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 136 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2310

  • Year Built

    1962

  • $/SqFt

    $563

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

Home For Sale $498,000

Reduced By $87,000

Charming home featuring a gray brick exterior, a welcoming front door, and professional landscaping at 2823 Cady Way, Winter Park, FL 32792
Bright living room featuring modern decor, a comfortable sofa and chairs, and stylish shelving at 2823 Cady Way, Winter Park, FL 32792
Cozy living room showcasing a sliding glass door and built-in shelving, inviting natural light and outdoor views at 2823 Cady Way, Winter Park, FL 32792
On Market For 127 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1688

  • Year Built

    1965

  • $/SqFt

    $295

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.

Pended $1,759,000

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 138 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

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 11 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 $625,000

Reduced By $25,000

Two-story home featuring a gray facade, white window trim, and a well-maintained front lawn at 1875 Staunton Ave, Winter Park, FL 32789
Charming two-story home showcasing a modern gray exterior with white window trim and a paved driveway at 1875 Staunton Ave, Winter Park, FL 32789
Stylish black front door with a glass insert, complemented by a modern digital lock and a vintage mailbox at 1875 Staunton Ave, Winter Park, FL 32789
On Market For 86 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2036

  • Year Built

    1954

  • $/SqFt

    $307

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

Home For Sale $1,599,900

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 143 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.

Home For Sale $398,000

Reduced By $27,000

Bright living room with fireplace,tile flooring and view to kitchen and backyard at 1309 Paradise Ln, Winter Park, FL 32792
Spacious living room with tiled floors and neutral color palette at 1309 Paradise Ln, Winter Park, FL 32792
Spacious living room with tiled floors and neutral color palette at 1309 Paradise Ln, Winter Park, FL 32792
On Market For 145 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1606

  • Year Built

    1984

  • $/SqFt

    $248

Conveniently located, this home offers easy access to nearby shopping, dining and major roadways and is in the A Rated Lake Howell High school zone. COLDWELL BANKER REALTY.

Home For Sale $665,000

Reduced By $34,000

Beautiful single-story home with a detached two-car garage and lush landscaping, great curb appeal at 1792 Killarney Dr, Winter Park, FL 32789
Paver walkway to front door with modern wood siding and beautiful landscaping at 1792 Killarney Dr, Winter Park, FL 32789
Inviting covered porch with decorative tile, seating, and views of the lush front yard, a relaxing spot at 1792 Killarney Dr, Winter Park, FL 32789
On Market For 135 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2082

  • Year Built

    1958

  • $/SqFt

    $319

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 $849,900

Reduced By $90,000

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
*POTENTIAL GREAT VALUE
On Market For 149 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2962

  • Year Built

    2010

  • $/SqFt

    $287

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

Pended $679,000

Reduced By $36,000

Updated kitchen featuring wood cabinets, stainless steel appliances, and quartz countertops at 958 Dunraven Dr, Winter Park, FL 32792
Updated kitchen with stainless steel appliances and wood cabinets at 958 Dunraven Dr, Winter Park, FL 32792
Bright kitchen boasts modern appliances and ample cabinet space at 958 Dunraven Dr, Winter Park, FL 32792
On Market For 136 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1835

  • Year Built

    1957

  • $/SqFt

    $370

Kenilworth Shores - All of this and Much, Much More! WELCOME HOME !! ! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $474,900

Reduced By $30,000

Inviting front entry with stone pillars and a double door at 1710 Aster Dr, Winter Park, FL 32792
Bright entryway with hardwood floors and a console table at 1710 Aster Dr, Winter Park, FL 32792
Spacious living room featuring a stone fireplace and hardwood floors at 1710 Aster Dr, Winter Park, FL 32792
On Market For 149 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1664

  • Year Built

    1979

  • $/SqFt

    $285

Garden Lake Estates - Highly desirable area with easy access to shopping & main roads. FOLIO REALTY LLC.

Home For Sale $549,900

Reduced By $50,000

Shows a spacious layout with multiple bedrooms and living areas at 1116 Fairway Dr, Winter Park, FL 32792
Single-story house with attached garage and landscaping at 1116 Fairway Dr, Winter Park, FL 32792
Single-story house with attached garage and landscaping at 1116 Fairway Dr, Winter Park, FL 32792
On Market For 150 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1738

  • Year Built

    1978

  • $/SqFt

    $316

You will surely LOVE to call this place your home! TURN-KEY MOVES REALTY.

Home For Sale $457,900

Reduced By $27,100

Home entryway with dark gray door and terracotta tile floor at 1354 Tierra Cir, Winter Park, FL 32792
Living room with hardwood floors, a large TV, and comfortable seating at 1354 Tierra Cir, Winter Park, FL 32792
Living room with hardwood floors, a large TV, and comfortable seating at 1354 Tierra Cir, Winter Park, FL 32792
On Market For 153 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1969

  • $/SqFt

    $251

Schedule your showing today and make this beautiful home yours! REAL ESTATE FIRM OF ORLANDO.

Home For Sale $10,900,000

Reduced By $1,000,000

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 157 Days
  • Bedrooms

    7

  • Full Bath(s)

    9

  • Sq. Ft.

    11255

  • Year Built

    2009

  • $/SqFt

    $968

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 $1,265,000

Reduced By $30,000

White house exterior with lush landscaping and a stone pathway at 1611 Walnut Ave, Winter Park, FL 32789
Charming house exterior with mature trees and a brick driveway at 1611 Walnut Ave, Winter Park, FL 32789
Bright living room with hardwood floors, stylish furniture, and access to the backyard at 1611 Walnut Ave, Winter Park, FL 32789
On Market For 157 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2635

  • Year Built

    1951

  • $/SqFt

    $480

Call to schedule a tour any time! COLDWELL BANKER RESIDENTIAL RE.

Pended $5,800,000

Reduced By $450,000

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 159 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4725

  • Year Built

    2008

  • $/SqFt

    $1,228

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 $999,000

Reduced By $101,000

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
On Market For 162 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3296

  • Year Built

    1928

  • $/SqFt

    $303

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

Home For Sale $499,900

Reduced By $35,100

House exterior showcasing a well-maintained lawn and attached garage at 1422 Tierra Cir, Winter Park, FL 32792
Bright living room showcasing a comfortable sectional sofa and stylish decor at 1422 Tierra Cir, Winter Park, FL 32792
Spacious living area with sectional sofa, TV, and access to the bathroom at 1422 Tierra Cir, Winter Park, FL 32792
On Market For 164 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1968

  • $/SqFt

    $274

Come take a tour of this immaculate 4 bedrooms, 2 bathrooms pool home today! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $575,000

Reduced By $55,000

Modern kitchen featuring white cabinets, stainless steel appliances, a black farmhouse sink, and marble countertops at 5255 Seminole Ave, Winter Park, FL 32792
Bright kitchen featuring a breakfast bar, white marble countertops, sleek black hardware, and stainless steel appliances at 5255 Seminole Ave, Winter Park, FL 32792
Bright bedroom showcasing a sliding barn door to the closet, large windows, and sleek marble flooring at 5255 Seminole Ave, Winter Park, FL 32792
On Market For 165 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2170

  • Year Built

    1957

  • $/SqFt

    $265

Don’t wait—schedule your showing today and take the first step toward living in your dream home! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $375,000

Reduced By $50,000

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 167 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1568

  • Year Built

    1956

  • $/SqFt

    $239

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 $299,000

Reduced By $51,000

Newly painted house exterior with well-maintained lawn at 2762 Hilda Cv, Winter Park, FL 32792
Spacious bonus room with tile floors and ample closet space at 2762 Hilda Cv, Winter Park, FL 32792
Bright bonus room featuring tile flooring and multiple closets at 2762 Hilda Cv, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 167 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1493

  • Year Built

    1981

  • $/SqFt

    $200

Slovak Village - Walking distance to Orlando’s famous Donut King, Kelly’s Homemade Ice Cream, and Foxtail Coffee! Submit your offer today! THE REALTY MEDICS.

Home For Sale $885,000

Reduced By $10,000

Two-story home with a light-beige exterior, two-car garage, and landscaped lawn at 1263 Verdant Glade Pl, Winter Park, FL 32792
Two-story home with festive lights, two-car garage, and brick paver driveway at 1263 Verdant Glade Pl, Winter Park, FL 32792
Two-story home with light-beige exterior, two-car garage, and gabled roof at 1263 Verdant Glade Pl, Winter Park, FL 32792
On Market For 175 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2589

  • Year Built

    2020

  • $/SqFt

    $342

Meadows At Hawks Crest - 20 foot ceilings, tile roof, too much to describe. Pics to follow FLAT FEE MLS REALTY.

Home For Sale $475,000

Reduced By $50,000

Inviting living room featuring a blue sectional, a large window, and a stylish bookshelf at 1608 Bomi Cir, Winter Park, FL 32792
Unique bookcase featuring pendant lights and decorative vases on the shelves at 1608 Bomi Cir, Winter Park, FL 32792
A well decorated living room with unique furniture and an open floor plan at 1608 Bomi Cir, Winter Park, FL 32792
On Market For 175 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1807

  • Year Built

    1983

  • $/SqFt

    $263

Tamarak - Call to schedule your private showing today! KELLER WILLIAMS ADVANTAGE III REALTY.

Pended $449,990

Reduced By $10,000

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 169 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1032

  • Year Built

    1950

  • $/SqFt

    $436

Lawndale - all the information is intended to be accurate and must be verified by buyers / realtor agent. TALENT REALTY SOLUTIONS.

Home For Sale $1,897,000

Reduced By $103,000

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 182 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3246

  • Year Built

    2025

  • $/SqFt

    $584

Lake Forest Park - This is your opportunity to build your dream Oasis and enjoy the Florida lifestyle! KELLER WILLIAMS WINTER PARK.

Home For Sale $4,750,000

Reduced By $235,000

Contemporary home boasting clean lines, a spacious driveway, and lush landscaping under a sunny sky at 2161 Sharon Rd, Winter Park, FL 32789
A modern residence showcased with an expansive paved driveway framed by manicured greenery at 2161 Sharon Rd, Winter Park, FL 32789
Elegant modern home with symmetrical design, manicured landscaping, and expansive driveway at twilight at 2161 Sharon Rd, Winter Park, FL 32789
On Market For 188 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6338

  • Year Built

    2023

  • $/SqFt

    $749

Tuscania - Get one step closer to owning the realization of your dream dwelling experience! LA ROSA REALTY HORIZONS LLC.

Home For Sale $510,000

Reduced By $52,000

Spacious living room with a stone fireplace, tiled floors, and comfortable seating at 4026 Tenita Dr, Winter Park, FL 32792
Living room with a stone fireplace and brown tiled floors at 4026 Tenita Dr, Winter Park, FL 32792
Bright bedroom with large bed, modern nightstands, and ample closet space at 4026 Tenita Dr, Winter Park, FL 32792
On Market For 192 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2122

  • Year Built

    1979

  • $/SqFt

    $240

Lake Waunatta Woods - Don't miss out on this exceptional property. OPENDOOR BROKERAGE LLC.

Home For Sale $695,000

Reduced By $104,000

An aerial shot of the home's location amid lush greenery and numerous lakes in Winter Park at 786 Antonette Ave, Winter Park, FL 32789
Covered boat dock featuring a storage shed and outdoor seating at 786 Antonette Ave, Winter Park, FL 32789
Bright sunroom with white walls, a blue floor, and a comfortable seating area by large windows at 786 Antonette Ave, Winter Park, FL 32789
On Market For 200 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1146

  • Year Built

    1925

  • $/SqFt

    $606

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 $460,000

Reduced By $39,999

House exterior with basketball hoop and driveway at 1621 Puritan,, Winter Park, FL 32792
Single-story house with large yard and neighborhood view at 1621 Puritan,, Winter Park, FL 32792
Home exterior featuring a large yard and basketball court at 1621 Puritan,, Winter Park, FL 32792
On Market For 178 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1765

  • Year Built

    1963

  • $/SqFt

    $261

Eastbrook - Conveniently located near Downtown Winter Park, Downtown Orlando, major highways, and top-rated schools, this home offers the perfect blend of tranquility and urban accessibility. Don’t miss this opportunity! PREFERRED REAL ESTATE BROKERS.

Home For Sale $8,799,000

Reduced By $2,200,999

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
On Market For 201 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 $2,799,000

Reduced By $500,000

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 209 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4875

  • Year Built

    2008

  • $/SqFt

    $574

Maitland Shores - Relaxation and a renewed sense of self await! COMPASS FLORIDA LLC.

Home For Sale $1,599,999

Reduced By $99,001

Elegant entryway with blue doors and stone pillars at 1429 Chapman Cir, Winter Park, FL 32789
Open living area with stone wall and backyard access at 1429 Chapman Cir, Winter Park, FL 32789
Bright living room with white sofas and large windows at 1429 Chapman Cir, Winter Park, FL 32789
On Market For 212 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3116

  • Year Built

    2014

  • $/SqFt

    $513

This masterfully designed residence offers the perfect balance of sophisticated style, modern convenience, and prime location. CORCORAN PREMIER REALTY.

Home For Sale $1,299,000

Luxury two-story home with tile roof and large driveway at 7440 Aloma Ave, Winter Park, FL 32792
Grand living room with ornate furnishings and a sweeping staircase at 7440 Aloma Ave, Winter Park, FL 32792
Elegant living room showcasing a dramatic staircase and high ceilings at 7440 Aloma Ave, Winter Park, FL 32792
On Market For 212 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4435

  • Year Built

    1950

  • $/SqFt

    $293

The possibilities are endless—don’t miss out on this incredible opportunity! MARZUCCO REAL ESTATE.

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Call to Schedule a Showing

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(407) 278-2057