172 Results

View 172 32789 Florida Homes for Sale

Home For Sale $479,000

Reduced By $36,000

Charming one-story home with a well-manicured lawn, a driveway, and an attached garage at 1564 Cavendish Rd, Winter Park, FL 32789
View Details 35 Photos
Inviting one-story home boasts lush landscaping and an attached garage at 1564 Cavendish Rd, Winter Park, FL 32789
A charming one-story home features a lush lawn and an attached garage at 1564 Cavendish Rd, Winter Park, FL 32789
Cozy front porch with white columns and a seating area at 1564 Cavendish Rd, Winter Park, FL 32789
On Market For 84 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1140

  • Year Built

    1953

  • $/SqFt

    $420

This community is in the heart of Winter Park, close to Park Ave, museums, restaurants and shoppes. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $539,000

Reduced By $26,000

Charming single-story home with a well-manicured lawn and beautiful blue shutters at 2381 Roxbury Rd, Winter Park, FL 32789
View Details 22 Photos
Bright living room featuring hardwood floors, cozy furniture, and ample natural light at 2381 Roxbury Rd, Winter Park, FL 32789
Inviting living area with fireplace, hardwood floors, and a ceiling fan at 2381 Roxbury Rd, Winter Park, FL 32789
Spacious open-concept living area featuring a fireplace, hardwood floors, and lots of windows at 2381 Roxbury Rd, Winter Park, FL 32789
On Market For 82 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1645

  • Year Built

    1949

  • $/SqFt

    $328

Glencoe - Highly Sought after- Move in Ready ! HURRY! Won't Last! ! KELLER WILLIAMS HERITAGE REALTY.

Home For Sale $1,395,000

Reduced By $255,000

Charming home featuring manicured landscaping, and a striking, modern front door entrance at 1701 Palmer Ave, Winter Park, FL 32789
View Details 64 Photos
A picturesque home with lush landscaping and mature trees adding natural beauty at 1701 Palmer Ave, Winter Park, FL 32789
Private courtyard area featuring tiled flooring and a charming decorative water feature at 1701 Palmer Ave, Winter Park, FL 32789
Outdoor kitchen area boasting a stainless steel grill and counter space at 1701 Palmer Ave, Winter Park, FL 32789
On Market For 88 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2841

  • Year Built

    1953

  • $/SqFt

    $491

Jenkins - Whether you're looking to move in and make it your own or renovate to create your dream home, this is a chance you don’t want to miss! Schedule your showing today! TRUST EQUITY GROUP LLC.

Pended $3,195,000

Reduced By $205,000

Charming traditional home with a manicured lawn, mature trees, and a welcoming front porch with columns at 1911 Stonehurst Rd, Winter Park, FL 32789
View Details 37 Photos
Charming brick home featuring a welcoming front porch with classic columns and a beautifully landscaped front yard at 1911 Stonehurst Rd, Winter Park, FL 32789
Expansive backyard showcasing the pool, patio, and meticulously maintained landscaping of the estate at 1911 Stonehurst Rd, Winter Park, FL 32789
An aerial view of a backyard with a pool, patio, fountain, and beautiful landscaping and mature trees at 1911 Stonehurst Rd, Winter Park, FL 32789
On Market For 65 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    5097

  • Year Built

    2001

  • $/SqFt

    $627

Stonehurst Estates - *Ask for a list of improvements, the floorplan and click on the virtual tour! FANNIE HILLMAN & ASSOCIATES.

Pended $875,000

Charming single-story home featuring a well-manicured lawn, covered porch, and inviting curb appeal at 1832 Magnolia Ave, Winter Park, FL 32789
View Details 31 Photos
Charming single-story home at dusk, featuring a well-manicured lawn and inviting curb appeal at 1832 Magnolia Ave, Winter Park, FL 32789
Inviting entryway showcasing wood floors, a decorative front door, and neutral wall paint at 1832 Magnolia Ave, Winter Park, FL 32789
Bright living room with stylish decor, wood flooring, modern lighting, and a comfortable sectional sofa at 1832 Magnolia Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 89 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2910

  • Year Built

    1954

  • $/SqFt

    $301

Temple Terrace - Don't miss the opportunity to make this unique Winter Park home yours! COMPASS FLORIDA LLC.

Home For Sale $2,795,000

Reduced By $100,000

Beautiful two-story home featuring a red tile roof, white stucco and meticulously landscaped front yard with tropical palm trees at 1630 Lasbury Ave, Winter Park, FL 32789
View Details 46 Photos
Beautiful backyard pool with travertine tile and white pergola surrounded by lush greenery at 1630 Lasbury Ave, Winter Park, FL 32789
Stunning aerial view of the property showcasing the house, pool, and landscaped yard at 1630 Lasbury Ave, Winter Park, FL 32789
Elegant home with a red tile roof, white exterior, circular driveway, and manicured landscaping at 1630 Lasbury Ave, Winter Park, FL 32789
On Market For 94 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    4912

  • Year Built

    2003

  • $/SqFt

    $569

Comstock Park - It’s a rare find in one of Winter Park’s most desirable neighborhoods. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $995,000

Reduced By $75,000

Charming single-story home with a well-manicured lawn, lush landscaping, and a spacious two-car garage at 250 Cortland Ave, Winter Park, FL 32789
View Details 68 Photos
Aerial view of a home with a private pool, lush greenery, and neatly fenced yard providing a serene retreat at 250 Cortland Ave, Winter Park, FL 32789
Bright living room features vaulted ceiling, hardwood floors, sliding glass doors to a pool, and neutral decor at 250 Cortland Ave, Winter Park, FL 32789
Spacious game room with a pool table, drum set, hardwood floors, and skylights, perfect for entertaining and leisure at 250 Cortland Ave, Winter Park, FL 32789
On Market For 94 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2114

  • Year Built

    1981

  • $/SqFt

    $471

Cortland Park - Don't miss the opportunity to own this true neighborhood gem in Winter Park, where luxury living and convenience meet. EXP REALTY LLC.

Home For Sale $1,475,000

Charming brick home with manicured lawn, brick pathway, and lush landscaping, creating inviting curb appeal at 1600 Barcelona Way, Winter Park, FL 32789
View Details 65 Photos
Charming brick home with manicured lawn, brick pathway, and lush landscaping, creating inviting curb appeal at 1600 Barcelona Way, Winter Park, FL 32789
Charming brick home with manicured lawn, brick pathway, and lush landscaping, creating inviting curb appeal at 1600 Barcelona Way, Winter Park, FL 32789
Charming brick home with manicured lawn, brick pathway, and lush landscaping, creating inviting curb appeal at 1600 Barcelona Way, Winter Park, FL 32789
On Market For 95 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3014

  • Year Built

    1972

  • $/SqFt

    $489

Don't miss your chance to own a piece of Winter Park's rich heritage! LPT REALTY, LLC.

Home For Sale $4,395,000

Lush backyard with mature trees, a walkway, and a waterfront view with a private dock at 1840 W Fawsett Rd, Winter Park, FL 32789
View Details 49 Photos
Stunning two-story home with manicured lawn, covered front porch, balcony, and elegant design at 1840 W Fawsett Rd, Winter Park, FL 32789
Inviting covered porch featuring comfortable seating, ceiling fans, and beautiful lake views at 1840 W Fawsett Rd, Winter Park, FL 32789
Cozy living room with a fireplace, high ceilings, large windows, and stylish furnishings at 1840 W Fawsett Rd, Winter Park, FL 32789
On Market For 96 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4129

  • Year Built

    1998

  • $/SqFt

    $1,064

Showings are by appointment only – schedule yours today. KELLY PRICE & COMPANY LLC.

Pended $1,800,000

Stunning two-story home with a modern design, two-car garage, stone accents, and meticulously landscaped yard at 1682 Arbor Park Dr, Winter Park, FL 32789
View Details 7 Photos
Bright, spacious kitchen with a large island, pendant lighting, modern appliances, and an adjacent dining area at 1682 Arbor Park Dr, Winter Park, FL 32789
Elegant living room with a modern fireplace, hardwood floors, ample seating, and natural light from the large sliding glass doors at 1682 Arbor Park Dr, Winter Park, FL 32789
Serene main bedroom with large windows, modern lighting, and a comfortable seating area, perfect for relaxation at 1682 Arbor Park Dr, Winter Park, FL 32789
On Market For 99 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2950

  • Year Built

    2025

  • $/SqFt

    $610

Conwill Estates - Final construction details, finishes, and features may vary. COMPASS FLORIDA LLC.

Home For Sale $1,775,000

Elegant exterior showcases a modern two-story home with a two car garage and manicured lawn at 1702 Arbor Park Dr, Winter Park, FL 32789
View Details 8 Photos
Modern kitchen features a marble island with bar seating, pendant lighting, and stainless steel appliances at 1702 Arbor Park Dr, Winter Park, FL 32789
Bright living room boasts a modern fireplace and light hardwood floors with sliding doors to the pool at 1702 Arbor Park Dr, Winter Park, FL 32789
Stylish primary bedroom features a king bed, hardwood floors, modern lighting, and windows at 1702 Arbor Park Dr, Winter Park, FL 32789
On Market For 99 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2950

  • Year Built

    2025

  • $/SqFt

    $602

Conwill Estates - Final construction details, finishes, and features may vary. COMPASS FLORIDA LLC.

Home For Sale $1,195,000

Reduced By $180,000

This property features a two car garage with a driveway and lush landscaping at 1213 Richmond Rd, Winter Park, FL 32789
View Details 65 Photos
A single story home with a two car garage, a paved driveway and well kept landscaping at 1213 Richmond Rd, Winter Park, FL 32789
An open foyer features tile and wood flooring, decorative trim and a staircase to the second floor at 1213 Richmond Rd, Winter Park, FL 32789
A foyer features wood and tile flooring, decorative trim, and a staircase to the second floor at 1213 Richmond Rd, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 102 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3204

  • Year Built

    1925

  • $/SqFt

    $373

DEEDED LAKE ACCESS on College Point. KELLY PRICE & COMPANY LLC.

Home For Sale $399,900

Reduced By $30,000

Charming single-story home with a well-manicured lawn, complemented by a quaint orange front door at 1975 Staunton Ave, Winter Park, FL 32789
View Details 36 Photos
Charming single-story home with a well-manicured lawn, complemented by a quaint orange front door at 1975 Staunton Ave, Winter Park, FL 32789
Bright living room with hardwood floors, a ceiling fan and stylish furniture; perfect for relaxing and entertaining at 1975 Staunton Ave, Winter Park, FL 32789
Bright living room featuring hardwood floors, a ceiling fan and plenty of natural light at 1975 Staunton Ave, Winter Park, FL 32789
On Market For 105 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1200

  • Year Built

    1949

  • $/SqFt

    $333

Karolina On Killarney - Conveniently located near I-4, Park Avenue, Winter Park Village, Dubsdread Golf Course, restaurants and shopping and downtown Orlando. ABSOLUTE REALTY GROUP, LLC.

Home For Sale $6,500,000

Reduced By $450,000

Stunning two-story yellow home featuring an elegant stone facade, private balcony, and meticulously landscaped front yard at 1400 Alabama Dr, Winter Park, FL 32789
View Details 96 Photos
Elegant stone entryway featuring a dark wood door with decorative glass and stylish outdoor lighting at 1400 Alabama Dr, Winter Park, FL 32789
Aerial view of the luxurious home features a tile roof, mature landscaping, and a stunning backyard pool and spa at 1400 Alabama Dr, Winter Park, FL 32789
Waterfront home with private boat docks surrounded by lush greenery and clear lake views at 1400 Alabama Dr, Winter Park, FL 32789
On Market For 90 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    7916

  • Year Built

    1996

  • $/SqFt

    $821

Kronenberger - Experience quintessential Winter Park living in this one-of-a-kind estate that is the epitome of opulence and grandeur. THE AGENCY ORLANDO.

Pended $1,425,000

Reduced By $155,000

Inviting front porch featuring elegant columns, stone walkway, and attractive landscaping at 1750 Winchester Dr, Winter Park, FL 32789
View Details 30 Photos
Close up of the front porch with seating, charming décor, and a beautifully crafted wood door at 1750 Winchester Dr, Winter Park, FL 32789
Open-concept kitchen featuring a blue island, bar seating, and modern finishes at 1750 Winchester Dr, Winter Park, FL 32789
Modern kitchen design with wood cabinets, a stainless-steel range, and ample natural light at 1750 Winchester Dr, Winter Park, FL 32789
On Market For 108 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2637

  • Year Built

    1960

  • $/SqFt

    $540

This is more than a house - it's an invitation to experience the refined Winter Park lifestyle you've been dreaming of. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,875,000

Reduced By $115,000

Charming two-story home with a lush front lawn and manicured landscaping provides great curb appeal at 1860 Via Contessa, Winter Park, FL 32789
View Details 90 Photos
Elegant two-story home with manicured front yard and covered porch is a perfect Gathering home at 1860 Via Contessa, Winter Park, FL 32789
A two-story home with an attached two-car garage and basketball hoop on a sunny day at 1860 Via Contessa, Winter Park, FL 32789
Inviting front porch with stone tile and white columns, perfect for relaxing or greeting guests at 1860 Via Contessa, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 114 Days

  • Bedrooms

    8

  • Full Bath(s)

    6

  • Sq. Ft.

    7000

  • Year Built

    2003

  • $/SqFt

    $411

Lugano Terrace - All measurements and dimensions should be verified. SIERRA REALTY GROUP LLC.

Home For Sale $975,000

Charming single-story home with a well-manicured lawn, vibrant plants, and an accessibility ramp at 674 W Comstock Ave, Winter Park, FL 32789
View Details 1 Photo
On Market For 115 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1045

  • Year Built

    1925

  • $/SqFt

    $933

This home has been remodeled and is a show place. A must see!! ! KELLER WILLIAMS WINTER PARK.

Home For Sale $2,500,000

Stately two-story home featuring columns, a landscaped yard, and a brick walkway at 450 Lakewood Dr, Winter Park, FL 32789
View Details 87 Photos
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 115 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.

Pended $659,000

Reduced By $90,000

Charming single-story home with a well-maintained lawn, featuring a dark exterior and bright white trim at 2812 Mulford Ave, Winter Park, FL 32789
View Details 18 Photos
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 115 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

Stunning, light-colored, two-story home featuring manicured landscaping and a gated entrance at 1660 Palmer Ave, Winter Park, FL 32789
View Details 48 Photos
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 116 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.

Pended $2,349,900

Reduced By $150,000

Elegant home featuring a gated entrance, black trim, and a meticulously maintained driveway at 301 Rippling Ln, Winter Park, FL 32789
View Details 43 Photos
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 115 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 a white exterior, complemented by a brick driveway and lush landscaping at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
View Details 49 Photos
Modern home with white exterior, complemented by a brick driveway and manicured landscaping at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
Aerial view of a modern white home near a golf course with mature landscaping at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
Bright open-concept living room with modern furnishings flowing into a stylish kitchen at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 117 Days

  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2284

  • Year Built

    2015

  • $/SqFt

    $558

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

Home For Sale $750,000

Contemporary home with a manicured yard and a stylish driveway providing ample parking at 726 N Pennsylvania Ave, Winter Park, FL 32789
View Details 30 Photos
Aerial view of modern home adjacent to a lush golf course and featuring ample parking at 726 N Pennsylvania Ave, Winter Park, FL 32789
Modern kitchen featuring stainless steel appliances, a black marble backsplash and a stylish breakfast bar at 726 N Pennsylvania Ave, Winter Park, FL 32789
Contemporary kitchen with stainless steel appliances, sleek black cabinetry and tiled flooring at 726 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 117 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1167

  • Year Built

    2015

  • $/SqFt

    $643

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

Home For Sale $550,000

Stylish modern home with a geometric design, white exterior, brick driveway, and manicured front yard hedge at 720 N Pennsylvania Ave, Winter Park, FL 32789
View Details 26 Photos
A scenic aerial view of a modern home with a golf course, railroad, and lush greenery in the neighborhood at 720 N Pennsylvania Ave, Winter Park, FL 32789
Open-concept living room with modern furniture, a ceiling fan, and an open view into the modern kitchen at 720 N Pennsylvania Ave, Winter Park, FL 32789
Bright living room with wood-look tile flooring, neutral sofa, pops of color, and contemporary decor at 720 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 117 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

Beautifully landscaped two story home with modern architectural details at 607 Ellen Dr, Winter Park, FL 32789
View Details 4 Photos
Waterfront homes featuring private docks and pools, situated on a picturesque lake at 607 Ellen Dr, Winter Park, FL 32789
Scenic lake view featuring a private dock and residents paddle boarding at 607 Ellen Dr, Winter Park, FL 32789
Elegant two-story house boasting contemporary design with a flat roof and vibrant landscaping at 607 Ellen Dr, Winter Park, FL 32789
On Market For 121 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2812

  • Year Built

    2025

  • $/SqFt

    $596

Last home available in the neighborhood and is priced well as this home will not last long! ! COMMUNITY REALTY ASSOCIATES.

Home For Sale $1,295,000

Charming single-Gathering home featuring a light-colored exterior, wood-look garage door, and well-manicured landscaping at 1611 Chestnut Ave, Winter Park, FL 32789
View Details 77 Photos
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 121 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

Charming single-story home with a well-maintained lawn, stucco facade, and a beautiful terracotta tile roof at 1690 Oneco Ave, Winter Park, FL 32789
View Details 31 Photos
Inviting single-story home with a brick driveway, lush lawn, and a charming terracotta-tiled roof at 1690 Oneco Ave, Winter Park, FL 32789
Beautiful single-story home featuring a well-manicured lawn, brick driveway, and a classic terracotta tile roof at 1690 Oneco Ave, Winter Park, FL 32789
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 122 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 $2,389,000

Reduced By $6,000

Stunning modern two-story home with a gravel driveway, two-car garage, and manicured landscaping at 2412 Chantilly Ave, Winter Park, FL 32789
View Details 84 Photos
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 $1,950,000

Two-story white house with a front yard and landscaping at 622 Penn Pl, Winter Park, FL 32789
View Details 26 Photos
Elegant entryway with hardwood floors, chandelier, and staircase at 622 Penn Pl, Winter Park, FL 32789
Spacious living room with hardwood floors, fireplace, and French doors at 622 Penn Pl, Winter Park, FL 32789
Open living room with hardwood floors and views into kitchen at 622 Penn Pl, Winter Park, FL 32789
On Market For 132 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

Charming two-story coral home with landscaped front yard and brick pathway at 817 Antonette Ave, Winter Park, FL 32789
View Details 60 Photos
Elegant entryway with checkered floor and unique decor at 817 Antonette Ave, Winter Park, FL 32789
Green striped sitting room with French doors opening to sunroom at 817 Antonette Ave, Winter Park, FL 32789
Green striped sitting room with ample natural light and unique decor at 817 Antonette Ave, Winter Park, FL 32789
On Market For 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

Stunning two-story home with black trim windows, a two-car garage, and a well-manicured lawn at 785 N Phelps Ave, Winter Park, FL 32789
View Details 10 Photos
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 135 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.

Home For Sale $1,300,000

Reduced By $80,000

Beautiful home with a large front yard, paved driveway and lush landscaping at 1400 S Pennsylvania Ave, Winter Park, FL 32789
View Details 50 Photos
Bright entryway with a large, black curio cabinet and white door at 1400 S Pennsylvania Ave, Winter Park, FL 32789
Open concept dining room with a view of the kitchen and living room at 1400 S Pennsylvania Ave, Winter Park, FL 32789
Modern dining room features an oval table, rattan light, and neutral decor at 1400 S Pennsylvania Ave, Winter Park, FL 32789
On Market For 137 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.

Pended $1,759,000

Two-story home with modern design, three-car garage, and landscaped front yard at 1660 Walnut Ave, Winter Park, FL 32789
View Details 11 Photos
Spacious living room with large windows, comfortable seating, and a modern aesthetic at 1660 Walnut Ave, Winter Park, FL 32789
Modern kitchen with gray cabinetry, center island, and stainless steel appliances at 1660 Walnut Ave, Winter Park, FL 32789
Bright bedroom with a ceiling fan, neutral color palette, and stylish decor at 1660 Walnut Ave, Winter Park, FL 32789
On Market For 139 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2172

  • Year Built

    2025

  • $/SqFt

    $810

Lake Knowles Terrace - Don’t miss the opportunity to make this stunning Winter Park home yours. COMPASS FLORIDA LLC.

Pended $1,500,000

Inviting front porch with blue door and screened enclosure at 747 Mcintyre Ave, Winter Park, FL 32789
View Details 44 Photos
Cute one-story house with a spacious lawn at 747 Mcintyre Ave, Winter Park, FL 32789
Cute one-story house with a spacious lawn at 747 Mcintyre Ave, Winter Park, FL 32789
Cute one-story house with a spacious lawn at 747 Mcintyre Ave, Winter Park, FL 32789
On Market For 12 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 with a modern gray facade, white window trim, and a paved driveway, offering curb appeal at 1875 Staunton Ave, Winter Park, FL 32789
View Details 42 Photos
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 87 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

Two-story home with a modern design, dark brown garage doors, and landscaping at 1417 Miller Ave, Winter Park, FL 32789
View Details 6 Photos
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 144 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

Charming single-story home boasts lush landscaping, a brick facade and a detached two-car garage at 1792 Killarney Dr, Winter Park, FL 32789
View Details 42 Photos
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 136 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
View Details 37 Photos
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 150 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

Grand two-story home with gated entry and lush landscaping at 1120 Preserve Point Dr, Winter Park, FL 32789
View Details 85 Photos
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 158 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

Inviting front entrance with lush landscaping and double doors at 1611 Walnut Ave, Winter Park, FL 32789
View Details 41 Photos
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 158 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

Spanish style home with brick driveway, lush landscaping, and two-car garage at 541 Virginia Dr, Winter Park, FL 32789
View Details 57 Photos
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 160 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

Charming ranch home with mature landscaping and a two-car garage at 2330 Westminster Ct, Winter Park, FL 32789
View Details 49 Photos
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 163 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 $375,000

Reduced By $50,000

Charming house with a spacious front yard and walkway at 2827 Euston Rd, Winter Park, FL 32789
View Details 30 Photos
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 168 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 $449,990

Reduced By $10,000

Charming light blue house with a white porch and landscaped yard at 1550 Indiana Ave, Winter Park, FL 32789
View Details 33 Photos
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 170 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 with modern design, two-car garage, and palm trees at 2260 Mulbry Dr, Winter Park, FL 32789
View Details 12 Photos
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 183 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

Stunning modern home featuring a grand entrance and meticulously landscaped front yard with paver driveway at 2161 Sharon Rd, Winter Park, FL 32789
View Details 62 Photos
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 189 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 $695,000

Reduced By $104,000

Charming yellow home featuring arched windows and a welcoming front entrance with potted plants at 786 Antonette Ave, Winter Park, FL 32789
View Details 38 Photos
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 201 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

Modern home with sleek design, light color, and a landscaped lawn at 2661 Via Tuscany, Winter Park, FL 32789
View Details 100 Photos
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 202 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

Beautiful two-story home with a lush green lawn at 2550 Venetian Way, Winter Park, FL 32789
View Details 41 Photos
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 210 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

Modern two-story house with stone accents at 1429 Chapman Cir, Winter Park, FL 32789
View Details 36 Photos
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 213 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.

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