156 Results

View 156 32789 Florida Homes for Sale

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 96 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 $1,825,000

Reduced By $170,000

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 96 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3971

  • Year Built

    1990

  • $/SqFt

    $460

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 $2,254,000

Reduced By $25,000

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 99 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3909

  • Year Built

    2015

  • $/SqFt

    $577

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 home under construction with zip system sheathing and a dumpster in the driveway at 785 N Phelps Ave, Winter Park, FL 32789
Modern kitchen with white cabinets, a large island, and stainless steel appliances at 785 N Phelps Ave, Winter Park, FL 32789
View of unfinished home interior with wood framing, block walls, and an unfinished concrete floor at 785 N Phelps Ave, Winter Park, FL 32789
On Market For 99 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 $1,770,000

Reduced By $180,000

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
*POTENTIAL GREAT VALUE
On Market For 99 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4227

  • Year Built

    2003

  • $/SqFt

    $419

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

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 94 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 $1,300,000

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 101 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2060

  • Year Built

    1962

  • $/SqFt

    $631

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

Home For Sale $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 103 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 69 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 $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 108 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 $4,500,000

New construction shows a brick home with an arched entryway under scaffolding at 702 Via Bella, Winter Park, FL 32789
Brick home with herringbone driveway, landscaping, and a two-car garage at 702 Via Bella, Winter Park, FL 32789
Two-story home with a two-car garage and landscaped yard, showcasing a beautiful brick exterior at 702 Via Bella, Winter Park, FL 32789
On Market For 110 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3720

  • Year Built

    2025

  • $/SqFt

    $1,210

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

Pended $995,000

Reduced By $185,000

Two-story house with a blue metal roof and attached garage at 1975 Biscayne Dr, Winter Park, FL 32789
Open concept living room and kitchen with white sofas and modern decor at 1975 Biscayne Dr, Winter Park, FL 32789
Living room features a white sectional sofa, fireplace, and Christmas tree at 1975 Biscayne Dr, Winter Park, FL 32789
On Market For 107 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3270

  • Year Built

    2020

  • $/SqFt

    $304

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

Home For Sale $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 114 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.

Home For Sale $11,900,000

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 122 Days
  • Bedrooms

    7

  • Full Bath(s)

    9

  • Sq. Ft.

    11255

  • Year Built

    2009

  • $/SqFt

    $1,057

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

Home For Sale $1,295,000

Reduced By $100,000

Spacious kitchen featuring a large island and stainless steel appliances at 433 Carolina Ave, Winter Park, FL 32789
Bright kitchen with white cabinets, quartz countertops, and a farmhouse sink at 433 Carolina Ave, Winter Park, FL 32789
Open concept kitchen with island seating and dark hardwood floors at 433 Carolina Ave, Winter Park, FL 32789
On Market For 122 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2700

  • Year Built

    2018

  • $/SqFt

    $480

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

Home For Sale $1,275,000

Reduced By $20,000

Charming house exterior with mature trees and a brick driveway at 1611 Walnut Ave, Winter Park, FL 32789
White house exterior with lush landscaping and a stone pathway at 1611 Walnut Ave, Winter Park, FL 32789
Spacious living room featuring high ceilings, large windows, and comfortable seating at 1611 Walnut Ave, Winter Park, FL 32789
On Market For 122 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2635

  • Year Built

    1951

  • $/SqFt

    $484

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

Pended $365,000

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

    4

  • Full Bath(s)

    1

  • Sq. Ft.

    1248

  • Year Built

    1954

  • $/SqFt

    $292

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

Home For Sale $5,800,000

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 125 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 126 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 $393,000

Reduced By $32,000

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
On Market For 132 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1568

  • Year Built

    1956

  • $/SqFt

    $251

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 $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 134 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 $2,000,000

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 147 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3246

  • Year Built

    2025

  • $/SqFt

    $616

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

Home For Sale $4,985,000

Luxury home with gray and white exterior, landscaping, and a spacious driveway at 2161 Sharon Rd, Winter Park, FL 32789
Stunning two-story home, white exterior, lush landscaping, and a large driveway at 2161 Sharon Rd, Winter Park, FL 32789
Modern home with white exterior, gray accents, and a two-car garage at 2161 Sharon Rd, Winter Park, FL 32789
On Market For 153 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6338

  • Year Built

    2023

  • $/SqFt

    $787

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

Pended $1,100,000

Reduced By $50,000

Ranch style home with a walkway leading to the entrance. Features brick exterior and blue accents at 708 Balmoral Rd, Winter Park, FL 32789
Front entrance with pink door and brick steps, blue siding, and landscaping at 708 Balmoral Rd, Winter Park, FL 32789
Bright entryway with tiled floor, a small table, and a view to the hardwood living area at 708 Balmoral Rd, Winter Park, FL 32789
On Market For 156 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2786

  • Year Built

    1960

  • $/SqFt

    $395

Kenilworth Shores - This fantastic location provides easy access to shopping, dining, and the popular Park Avenue with its boutique shopping and great restaurants. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $695,000

Reduced By $104,000

A covered boathouse on a grassy lawn near the lake, featuring a fenced gate and wooden deck at 786 Antonette Ave, Winter Park, FL 32789
Covered boat dock with ceiling fans, Adirondack chairs, and boat lift ready for lake adventures at 786 Antonette Ave, Winter Park, FL 32789
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
On Market For 165 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 $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
*POTENTIAL GREAT VALUE
On Market For 166 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 174 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 177 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 $534,900

Reduced By $120,000

Brick ranch home with a two-car garage and a curved driveway at 2518 Sweetwater Trl, Winter Park, FL 32789
Ranch style brick home with a two-car garage and landscaped lawn at 2518 Sweetwater Trl, Winter Park, FL 32789
Brick ranch house with a two-car garage and lush green lawn at 2518 Sweetwater Trl, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 179 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2205

  • Year Built

    1965

  • $/SqFt

    $243

Do not miss out on the perfect blend of style, comfort, and location! BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY.

Pended $450,000

Reduced By $49,000

Bright living room featuring light wood floors and a ceiling fan at 2341 Devon Ct, Winter Park, FL 32789
Spacious living room with light wood floors, open to kitchen at 2341 Devon Ct, Winter Park, FL 32789
Open concept living room with hardwood floors and a view to kitchen at 2341 Devon Ct, Winter Park, FL 32789
On Market For 148 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1773

  • Year Built

    1953

  • $/SqFt

    $254

Glencoe - Schedule your appointment today to preview this Winter Park jem! UNITED REAL ESTATE PREFERRED.

Pended $829,000

Reduced By $140,000

Modern kitchen with white cabinets, quartz countertops, and gold accents at 1795 Walker Ave, Winter Park, FL 32789
Bright dining room with wood table and mustard yellow chairs at 1795 Walker Ave, Winter Park, FL 32789
Modern kitchen with a breakfast bar, white cabinets and gold fixtures at 1795 Walker Ave, Winter Park, FL 32789
On Market For 184 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    1813

  • Year Built

    1958

  • $/SqFt

    $457

Osceola Heights - Don't miss out on this opportunity—act quickly! ALIGN REAL ESTATE LLC.

Home For Sale $1,295,000

Reduced By $155,000

Charming lakeside home featuring a private dock, perfect for boating and enjoying waterfront living at 632 Country Club Dr, Winter Park, FL 32789
Elegant living room with French doors offering scenic views of the tranquil lake at 632 Country Club Dr, Winter Park, FL 32789
Inviting home with well-maintained landscaping and a charming exterior, perfect for curb appeal at 632 Country Club Dr, Winter Park, FL 32789
On Market For 197 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2342

  • Year Built

    1952

  • $/SqFt

    $553

632 Country Club is approximately 1.5 miles from luxurious Park Avenue and 5 miles from downtown Orlando. KELLER WILLIAMS ADVANTAGE REALTY.

Pended $3,250,000

Reduced By $325,000

Aerial of waterfront home with boat dock at 1900 W Fawsett Rd, Winter Park, FL 32789
Aerial of waterfront property with boathouse at 1900 W Fawsett Rd, Winter Park, FL 32789
Aerial view of waterfront homes and boat docks at 1900 W Fawsett Rd, Winter Park, FL 32789
On Market For 195 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4600

  • Year Built

    1969

  • $/SqFt

    $707

Don’t miss the opportunity to make this stunning lakefront home your own! KELLY PRICE & COMPANY LLC.

Home For Sale $855,555

Reduced By $33,333

Mid-century modern home with white exterior, black accents, and a spacious lawn at 2128 Sycamore Dr, Winter Park, FL 32789
Mid-century modern home with white exterior, black accents, and a spacious lawn at 2128 Sycamore Dr, Winter Park, FL 32789
White mid-century modern home with a large backyard at 2128 Sycamore Dr, Winter Park, FL 32789
On Market For 201 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1760

  • Year Built

    1953

  • $/SqFt

    $486

Northwood Terrace - Act fast—opportunities like this don’t last long! EXP REALTY LLC.

Home For Sale $499,000

Reduced By $76,000

Aerial view showing home's location near a pond at 2821 Chantilly Ave, Winter Park, FL 32789
Detailed survey map of the property and surrounding area at 2821 Chantilly Ave, Winter Park, FL 32789
Bright dining area with hardwood floors and kitchen view at 2821 Chantilly Ave, Winter Park, FL 32789
On Market For 204 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1440

  • Year Built

    1959

  • $/SqFt

    $347

Winter Park Manor - Extras include: updated electric panel, 2017 AC, updated plumbing & 24x12 backyard shed. WELCOME HOME! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $5,000,000

Reduced By $400,000

Elegant home entrance with a pink door, arched entryway, and potted plants at 2228 Azalea Pl, Winter Park, FL 32789
House exterior showcasing a classic design with a green lawn at 2228 Azalea Pl, Winter Park, FL 32789
Vibrant living room with bold colors, unique artwork, and comfortable seating at 2228 Azalea Pl, Winter Park, FL 32789
On Market For 205 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5072

  • Year Built

    2008

  • $/SqFt

    $986

Maitland Shores - The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. COMPASS FLORIDA LLC.

Home For Sale $2,350,000

Reduced By $49,000

Contemporary home with gray and white exterior, showcasing a stylish and modern design at 2522 Lafayette Ave, Winter Park, FL 32789
Modern two-story home with a rooftop deck and attached garage, offering city views at 2522 Lafayette Ave, Winter Park, FL 32789
Stylish home with large windows and a modern facade, creating a welcoming curb appeal at 2522 Lafayette Ave, Winter Park, FL 32789
On Market For 205 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3399

  • Year Built

    2022

  • $/SqFt

    $691

Truly photos and words do not begin to describe this Architectural Brilliance, come out and explore this gem where you will be greeted by Astro the Robot. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $3,499,500

Reduced By $392,500

Grand two-story brick home with a circular driveway at 1391 Richmond Rd, Winter Park, FL 32789
Brick home nestled in lush landscaping, large driveway at 1391 Richmond Rd, Winter Park, FL 32789
Mature trees and landscaped gardens surround the home at 1391 Richmond Rd, Winter Park, FL 32789
On Market For 216 Days
  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    4635

  • Year Built

    2001

  • $/SqFt

    $755

Virginia Heights - Celebrate nature’s wildlife which range from owls, great white egrets, blue herons, hawks, bunnies, and otters in your private sanctuary minutes to Winter Park’s premier dining, upscale shopping, Mead Botanical Garden, and the highly coveted Audubon K-8, and Winter Park High! STOCKWORTH REALTY GROUP.

Home For Sale $1,397,000

Reduced By $98,000

Modern home nestled on a tree-lined street with a brick road at 1371 Lyndale Blvd, Winter Park, FL 32789
Top-down view of a home showcasing its layout and landscaped yard at 1371 Lyndale Blvd, Winter Park, FL 32789
Aerial view of a home showcasing the property and surrounding neighborhood at 1371 Lyndale Blvd, Winter Park, FL 32789
On Market For 226 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2739

  • Year Built

    1949

  • $/SqFt

    $510

Dixie Terrace - With every detail thoughtfully curated, this property is more than just a home—it's a lifestyle. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $1,999,993

Reduced By $200,006

Home's side view, showcasing garage and landscaping at 1451 Lyndale Blvd, Winter Park, FL 32789
Inviting swimming pool with a spacious patio area at 1451 Lyndale Blvd, Winter Park, FL 32789
Two-story house with a double front door and landscaped yard at 1451 Lyndale Blvd, Winter Park, FL 32789
On Market For 250 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    3853

  • Year Built

    2012

  • $/SqFt

    $519

Dixie Terrace - Schedule your private showing today and discover what makes this Winter Park home truly exceptional. REALTY ONE GROUP MVP.

Home For Sale $3,295,000

Inviting covered front porch with stylish seating, providing a tranquil outdoor space at 1730 Winchester Dr, Winter Park, FL 32789
Cozy outdoor living area with a stone fireplace and comfortable seating, perfect for relaxation at 1730 Winchester Dr, Winter Park, FL 32789
Elegant staircase featuring wood treads, iron railings, and stylish lighting at 1730 Winchester Dr, Winter Park, FL 32789
On Market For 261 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4080

  • Year Built

    2024

  • $/SqFt

    $808

Schedule your private tour today to see this stunning property in person! KELLER WILLIAMS WINTER PARK.

Pended $799,900

Reduced By $150,100

Tan house with a garage and driveway at 731 Midget Dr, Winter Park, FL 32789
Aerial view showing a home's location on Midget Dr at 731 Midget Dr, Winter Park, FL 32789
Home with a brick driveway and lush landscaping at 731 Midget Dr, Winter Park, FL 32789
On Market For 266 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    960

  • Year Built

    1941

  • $/SqFt

    $833

Don’t miss this diamond in the rough – call today for your showing!! ! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $1,739,000

Reduced By $56,000

Single story home with brick driveway and rocking chairs on the porch at 279 Rippling Ln, Winter Park, FL 32789
Lakefront property with a spacious wooden dock at 279 Rippling Ln, Winter Park, FL 32789
Lakefront property offering breathtaking water views and lush landscaping at 279 Rippling Ln, Winter Park, FL 32789
On Market For 270 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3472

  • Year Built

    1961

  • $/SqFt

    $501

Don’t miss this rare opportunity to own a slice of paradise in one of Winter Park’s most sought-after locations. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $997,000

Reduced By $202,900

Bright and airy entryway with hardwood floors and stylish decor at 1840 Biscayne Dr, Winter Park, FL 32789
Modern home office featuring large windows and comfortable seating at 1840 Biscayne Dr, Winter Park, FL 32789
Spa-like bathroom with a glass shower and gray vanity at 1840 Biscayne Dr, Winter Park, FL 32789
On Market For 289 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2641

  • Year Built

    2024

  • $/SqFt

    $378

Karolina On Killarney - Calling all medical professionals, this home is located 1.7 miles or 7 minutes to Advent Health and a mere 5.6 miles or 14 minutes to Orlando Health. COMPASS FLORIDA LLC.

Home For Sale $1,625,000

Reduced By $70,000

Inviting front porch entry to this beautiful brick home at 1650 Lakehurst Ave, Winter Park, FL 32789
Elegant entryway with hardwood floors and a chandelier at 1650 Lakehurst Ave, Winter Park, FL 32789
Light and bright staircase with hardwood floors at 1650 Lakehurst Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 289 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3777

  • Year Built

    1992

  • $/SqFt

    $430

Comstock Park - Located minutes from Park Avenue, Rollins College, Advent Health, and more this home is conveniently located and zoned for the A-rated Lakemont/Maitland Middle/WPHS school district. KELLY PRICE & COMPANY LLC.

Pended $4,200,000

Luxury two-story home with lake views at 571 Lake Front Blvd, Winter Park, FL 32789
Lakefront property with modern home at 571 Lake Front Blvd, Winter Park, FL 32789
Lakefront home nestled among trees at 571 Lake Front Blvd, Winter Park, FL 32789
On Market For 298 Days
  • Bedrooms

    7

  • Full Bath(s)

    5

  • Sq. Ft.

    5500

  • Year Built

    2025

  • $/SqFt

    $764

From upscale dining and shopping to outdoor activities and renowned schools, this location balances convenience and exclusivity. PREMIER SOTHEBY'S INTL. REALTY.

Pended $1,575,000

Contemporary home with dark exterior, balcony, and attached garage at 627 Country Club Dr, Winter Park, FL 32789
Two-story modern home with wood and concrete accents, balcony, and attached garage at 627 Country Club Dr, Winter Park, FL 32789
Modern home with a balcony, attached garage, and landscaping at 627 Country Club Dr, Winter Park, FL 32789
On Market For 63 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2858

  • Year Built

    2024

  • $/SqFt

    $551

Lake Killarney Shores - Make an appointment today before this amazing home is gone. CLASSIC HOMES.

Home For Sale $2,160,000

Reduced By $90,000

Elegant living room with high ceilings, fireplace, and access to the pool area at 2234 Via Luna, Winter Park, FL 32789
Two story house with white brick exterior, manicured lawn, and walkway at 2234 Via Luna, Winter Park, FL 32789
Expansive backyard with fire pit and seating area under lush trees at 2234 Via Luna, Winter Park, FL 32789
On Market For 310 Days
  • Bedrooms

    6

  • Full Bath(s)

    3

  • Sq. Ft.

    3554

  • Year Built

    1998

  • $/SqFt

    $608

Tuscany Terrace - This home is being sold with all the furniture but can be removed if Buyer does not want it. Some pictures are "Virtually Staged." LOKATION.

Home For Sale $849,000

Reduced By $151,000

Open concept kitchen with island and hardwood floors at 2955 Lolissa Ln, Winter Park, FL 32789
Open living room and kitchen with hardwood floors, island, and modern appliances at 2955 Lolissa Ln, Winter Park, FL 32789
Spacious living area with hardwood floors and open concept design at 2955 Lolissa Ln, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 366 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3902

  • Year Built

    1969

  • $/SqFt

    $218

Don't miss this opportunity to live, work and play in Winter Park just 4 miles away from downtown Park Avenue shops, restaurants and recreation. COLDWELL BANKER REALTY.

Home For Sale $699,900

Reduced By $200,099

Newly renovated home with gray exterior and stone accents, large tree in front at 2612 Lafayette Ave, Winter Park, FL 32789
Light and bright entryway with gray walls and wood floors at 2612 Lafayette Ave, Winter Park, FL 32789
Entryway with contemporary decor, hardwood floors, and view to living room at 2612 Lafayette Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 430 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2447

  • Year Built

    1956

  • $/SqFt

    $286

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

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Call to Schedule a Showing

(407) 718-3706

(407) 718-3706