163 Results

View 163 32789 Florida Homes for Sale

Home For Sale $2,500,000

Stunning two-story home with a grand entrance, featuring a beautifully landscaped front yard and second story balcony at 450 Lakewood Dr, Winter Park, FL 32789
Enjoy outdoor living on this covered patio, with views of the pool and lush landscaping at 450 Lakewood Dr, Winter Park, FL 32789
Backyard pool with fountain and spa, complemented by the home's architecture at 450 Lakewood Dr, Winter Park, FL 32789
On Market For 98 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4676

  • Year Built

    2000

  • $/SqFt

    $535

Osceola Shores - Home has natural gas for the newer tankless water heater, pool heater, cooktop and the outdoor firepit. Roof new 2020. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $659,000

Reduced By $90,000

Modern kitchen featuring white cabinets, granite countertops, stainless steel appliances, and stylish lighting at 2812 Mulford Ave, Winter Park, FL 32789
Contemporary kitchen with black appliances, granite countertops, white cabinets, and sleek modern lighting at 2812 Mulford Ave, Winter Park, FL 32789
Well-lit kitchen featuring stainless steel appliances, white cabinetry, granite counters and a dining area at 2812 Mulford Ave, Winter Park, FL 32789
On Market For 98 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1627

  • Year Built

    1953

  • $/SqFt

    $405

Northwood Terrace - The living room also connects via french doors to a great flex space that could morph into a homework station, home office, or new laundry room. Welcome Home! SYNCHRONICITY REAL ESTATE SOLUTIONS.

Home For Sale $5,200,000

Reduced By $500,000

Beautiful two-story home with a landscaped front yard, manicured hedges and a paver driveway at 1660 Palmer Ave, Winter Park, FL 32789
An elegant two-story home is beautifully landscaped and includes planters and manicured gardens at 1660 Palmer Ave, Winter Park, FL 32789
A charming front entry boasts a covered porch with black lanterns and beautiful double doors at 1660 Palmer Ave, Winter Park, FL 32789
On Market For 99 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6406

  • Year Built

    2024

  • $/SqFt

    $812

Comstock Park - The furnishings package can be purchased separately. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $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 99 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.

Pended $849,000

Reduced By $76,000

Inviting light blue home features a curved driveway, well-kept landscaping, and mid-century modern architectural details at 625 Worthington Dr, Winter Park, FL 32789
A cozy light blue home showcasing a welcoming front porch with white chairs and mid-century modern decorative elements at 625 Worthington Dr, Winter Park, FL 32789
Charming front porch featuring comfortable seating, a decorative front door, and stylish accents at 625 Worthington Dr, Winter Park, FL 32789
On Market For 95 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2133

  • Year Built

    1958

  • $/SqFt

    $398

With the neighborhood rapidly evolving, many homes around this property are being torn down to make way for new, custom-built estates, including expansive 4,000 square foot homes valued at over $3 million. KELLY PRICE & COMPANY 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 100 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 100 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 100 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 $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 104 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

Aerial view of the home showcasing its gray roof, backyard space, and proximity to surrounding neighborhood at 1611 Chestnut Ave, Winter Park, FL 32789
Property highlighted by boundary lines showing its location and surrounding homes and well-manicured lawns at 1611 Chestnut Ave, Winter Park, FL 32789
Overhead image of a neighborhood featuring well-maintained homes, private pools, and mature landscaping at 1611 Chestnut Ave, Winter Park, FL 32789
On Market For 104 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 105 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.

Pended $1,100,000

Reduced By $150,000

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 102 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2220

  • Year Built

    1959

  • $/SqFt

    $495

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

Home For Sale $2,389,000

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 93 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 $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 115 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 $1,795,000

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 105 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 118 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 118 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.

Pended $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 112 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 120 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.

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 122 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 88 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 69 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 127 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 $665,000

Reduced By $34,000

View of a one-story home with an attached garage, gray brick, and a concrete driveway 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
Cozy front porch with chairs, decorative tile, and a view of the neighborhood at 1792 Killarney Dr, Winter Park, FL 32789
On Market For 119 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 133 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 $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 141 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 $1,295,000

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 141 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 $1,265,000

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 140 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.

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 144 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 146 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 $389,000

Reduced By $36,000

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 151 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1568

  • Year Built

    1956

  • $/SqFt

    $248

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 153 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 166 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 $4,750,000

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 172 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.

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 175 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

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
Bright sunroom with white walls, a blue floor, and a comfortable seating area by large windows at 786 Antonette Ave, Winter Park, FL 32789
Inviting living room with hardwood floors, a cozy couch, and a decorative white fireplace at 786 Antonette Ave, Winter Park, FL 32789
On Market For 184 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
On Market For 184 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 193 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 196 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 $509,900

Reduced By $145,000

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 198 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2205

  • Year Built

    1965

  • $/SqFt

    $231

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

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 161 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 216 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.

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 220 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 $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 224 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 $2,270,000

Reduced By $129,000

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 224 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3399

  • Year Built

    2022

  • $/SqFt

    $668

The value on this beauty will soar as Lafayette is transformed into an extension to Temple Ave and the VIA'S of Winter Park, stay ahead of this transformation and make Winter Park Village your home! 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 235 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

Aerial view of the property shows the home's roof, backyard play area, and expansive hardscaped parking area at 1371 Lyndale Blvd, Winter Park, FL 32789
Beautiful, white home with manicured lawn and garden area, with a brick street along the front at 1371 Lyndale Blvd, Winter Park, FL 32789
Stunning home with well-maintained landscaping, a carport and geometric, hardscaped parking in the front at 1371 Lyndale Blvd, Winter Park, FL 32789
On Market For 244 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 269 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 $3,249,000

Reduced By $46,000

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 280 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4080

  • Year Built

    2024

  • $/SqFt

    $796

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 285 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.

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Call to Schedule a Showing

(386) 801-5417

(386) 801-5417