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32789 Homes For Sale & 32789 FL Real Estate

Home For Sale $1,500,000

Charming two-story home with stone accents, a well-manicured lawn, and a bright blue front door at 1741 Pine Ave, Winter Park, FL 32789
View Details 43 Photos
Inviting covered porch with stone accents, decorative columns, and cozy seating area with a blue front door at 1741 Pine Ave, Winter Park, FL 32789
Bright foyer featuring hardwood floors, an elegant chandelier, and a glimpse into the open-concept living space at 1741 Pine Ave, Winter Park, FL 32789
Elegant dining room with hardwood floors and decoratively appointed furniture adjacent to the living area at 1741 Pine Ave, Winter Park, FL 32789
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3297

  • Year Built

    2002

  • $/SqFt

    $455

Conwill Estates - Plus, with top-rated Winter Park Schools, this home offers everything you need! FANNIE HILLMAN & ASSOCIATES.

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 7 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 3 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 $1,775,000

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 3 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.

Pended $3,500,000

Breathtaking aerial view of a lakefront property with lush landscaping and direct access to the water at 443 Lakewood Dr, Winter Park, FL 32789
View Details 15 Photos
Charming one-story home featuring a large, well-manicured front lawn with mature trees and established landscaping at 443 Lakewood Dr, Winter Park, FL 32789
Spacious tiled back patio with white metal railing overlooking a serene lake view and mature trees at 443 Lakewood Dr, Winter Park, FL 32789
Inviting back patio with comfortable seating and stunning lake views, perfect for outdoor relaxation and entertaining at 443 Lakewood Dr, Winter Park, FL 32789
On Market For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2803

  • Year Built

    1954

  • $/SqFt

    $1,249

Osceola Shores - Opportunity awaits the buyer of this gorgeous property! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,375,000

Large two-car garage featuring an extended driveway and lush landscaping at 1213 Richmond Rd, Winter Park, FL 32789
View Details 27 Photos
An eye-level shot of the home's front exterior with the garage on the left at 1213 Richmond Rd, Winter Park, FL 32789
Welcoming foyer featuring hardwood floors, decorative sconces, and beautiful wrought iron railing at 1213 Richmond Rd, Winter Park, FL 32789
Kitchen with stainless appliances, modern cabinetry, and granite countertops at 1213 Richmond Rd, Winter Park, FL 32789
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3204

  • Year Built

    1925

  • $/SqFt

    $429

This is the rare chance to live in an exceptional location that blends luxury, convenience, and tranquility. KELLY PRICE & COMPANY LLC.

Home For Sale $4,875,000

Stunning modern two-story home with large windows, crisp white exterior, and meticulously landscaped front yard at 229 Alexander Pl, Winter Park, FL 32789
View Details 65 Photos
Modern two-story home with manicured lawn and beautiful landscaping at twilight at 229 Alexander Pl, Winter Park, FL 32789
Stunning contemporary home with a modern stone facade, lush landscaping, and a clean architectural design at 229 Alexander Pl, Winter Park, FL 32789
Detailed view of the entryway, highlighting the modern door, stone facade, and the sleek, minimalist design at 229 Alexander Pl, Winter Park, FL 32789
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4431

  • Year Built

    2012

  • $/SqFt

    $1,100

Experience luxury, innovation and convenience in one of Winter Park’s sought-after locations, moments from dining, shopping and cultural experiences. PREMIER SOTHEBY'S INTL. REALTY.

Pended $4,799,900

Beautiful modern two-story home with a manicured lawn, stone accents, and a spacious three-car garage at 1691 Chestnut Ave, Winter Park, FL 32789
View Details 69 Photos
Beautiful modern two-story home with a manicured lawn, stone accents, and a spacious three-car garage at 1691 Chestnut Ave, Winter Park, FL 32789
Beautiful modern two-story home with manicured landscaping and an inviting, paved driveway and walkway at 1691 Chestnut Ave, Winter Park, FL 32789
Modern two-story home featuring manicured landscaping and an inviting paved driveway and walkway, lit for evening at 1691 Chestnut Ave, Winter Park, FL 32789
On Market For 9 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4582

  • Year Built

    2024

  • $/SqFt

    $1,048

Lake Knowles Terrace - This elegant home will not last! COMPASS FLORIDA LLC.

Pended $4,600,000

Stunning lakefront home featuring a pool, covered patio, and lush landscaping at 2118 Lake Dr, Winter Park, FL 32789
View Details 41 Photos
Beautiful two-story home with a brick driveway, manicured landscaping, and a three-car garage at 2118 Lake Dr, Winter Park, FL 32789
Inviting covered porch with wood floors, landscaping, and views of the property at 2118 Lake Dr, Winter Park, FL 32789
Outdoor patio area with seating overlooking the waterfront at 2118 Lake Dr, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 10 Days

  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    6000

  • Year Built

    2012

  • $/SqFt

    $767

Experience the serenity and tranquility of old Florida under the majestic cypress trees beaming with wildlife/eagles/beavers and the ever changing landscape from sunrise to sunset. COMPASS FLORIDA LLC.

Home For Sale $429,900

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 34 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 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1200

  • Year Built

    1949

  • $/SqFt

    $358

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.

Pended $6,950,000

Elegant two-story home with manicured landscaping and a grand entrance, framed by mature palm trees and decorative driveway at 1400 Alabama Dr, Winter Park, FL 32789
View Details 99 Photos
Stunning Mediterranean home featuring a circular driveway and meticulously landscaped grounds with mature palm trees at 1400 Alabama Dr, Winter Park, FL 32789
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
On Market For 12 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    7916

  • Year Built

    1996

  • $/SqFt

    $878

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

Home For Sale $1,799,000

An impressive exterior elevation view of a white two-story home with a clay tile roof and meticulously manicured landscaping at 1731 Windsor Dr, Winter Park, FL 32789
View Details 12 Photos
The spacious living room is highlighted by a fireplace, vaulted ceilings, and natural light from abundant windows at 1731 Windsor Dr, Winter Park, FL 32789
A chef's kitchen with a large island, stainless steel appliances, and an open design creates an inviting space at 1731 Windsor Dr, Winter Park, FL 32789
The light filled living room with an open-concept design provides seamless access to the outdoor pool and kitchen at 1731 Windsor Dr, Winter Park, FL 32789
On Market For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3669

  • Year Built

    2007

  • $/SqFt

    $490

Previous MLS listing 3669sqft heated. Sellers=Listing Agents. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $669,000

Charming single-Gathering home with a modern design and well-manicured lawn, complemented by a two-car garage at 2739 Riddle Dr, Winter Park, FL 32789
View Details 45 Photos
Charming single-Gathering home with a modern design and well-manicured lawn, complemented by a two-car garage at 2739 Riddle Dr, Winter Park, FL 32789
Single Gathering home with a modern design, complemented by a two-car garage, and fenced yard at 2739 Riddle Dr, Winter Park, FL 32789
Close up of a front door of single Gathering home with a modern design, complemented by a two-car garage at 2739 Riddle Dr, Winter Park, FL 32789
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1881

  • Year Built

    2023

  • $/SqFt

    $356

Glencoe - Contact us today to schedule a showing! BRAINARD REALTY.

Pended $565,000

Charming single-story home with manicured lawn, black shutters, and a welcoming entrance at 1531 Norfolk Ave, Winter Park, FL 32789
View Details 25 Photos
Charming single-story home with manicured lawn, black shutters, and a welcoming entrance at 1531 Norfolk Ave, Winter Park, FL 32789
Inviting tiled foyer with natural light, leading to an open floor plan with plant accents at 1531 Norfolk Ave, Winter Park, FL 32789
Bright, tiled foyer featuring a decorative bench and seamless transition to the living area at 1531 Norfolk Ave, Winter Park, FL 32789
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1795

  • Year Built

    1947

  • $/SqFt

    $315

Orwin Manor - Schedule your showing today and experience the charm and convenience of this exceptional College Park home! HOMEVEST REALTY.

Home For Sale $1,580,000

Charming home exterior with white painted brick, a lush lawn, and mature landscaping at 1750 Winchester Dr, Winter Park, FL 32789
View Details 30 Photos
Inviting front porch featuring elegant columns, stone walkway, and attractive landscaping at 1750 Winchester Dr, Winter Park, FL 32789
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
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2637

  • Year Built

    1960

  • $/SqFt

    $599

Reside in one of Orlando’s friendliest and family-centric neighborhoods, all in style and turnkey comfort. FANNIE HILLMAN & ASSOCIATES.

Pended $1,395,000

Charming single-story home with a well-manicured lawn and mature landscaping at 1771 Winchester Dr, Winter Park, FL 32789
View Details 1 Photo
On Market For 13 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2516

  • Year Built

    1957

  • $/SqFt

    $554

Located in a sought-after school district, this neighborhood offers an exceptional educational environment. FANNIE HILLMAN & ASSOCIATES.

Pended $649,000

Charming home featuring a brick driveway, manicured bushes, lush palms, and a two-car garage at 721 Glenridge Way, Winter Park, FL 32789
View Details 28 Photos
Beautiful home showcasing well-maintained landscaping, a quaint walkway, and a bright, welcoming facade at 721 Glenridge Way, Winter Park, FL 32789
Inviting outdoor patio with a turquoise table set and lush artificial turf, perfect for relaxing or entertaining at 721 Glenridge Way, Winter Park, FL 32789
Welcoming front entrance with a dark wood door, tiled flooring, and decorative plants for added curb appeal at 721 Glenridge Way, Winter Park, FL 32789
On Market For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1545

  • Year Built

    1981

  • $/SqFt

    $420

Lake Virginia - Call today to schedule your private showing! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $4,500,000

Stunning two-story home featuring a lush green landscape and a paved circular driveway at 1336 College Pt, Winter Park, FL 32789
View Details 32 Photos
Charming white home showcasing a whimsical blue sky door and manicured front yard at 1336 College Pt, Winter Park, FL 32789
Beautiful backyard features an in-ground pool, lounge chairs, and guest house surrounded by green lawns at 1336 College Pt, Winter Park, FL 32789
Waterfront view of home with boat dock, lush lawns and tall trees at 1336 College Pt, Winter Park, FL 32789
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3181

  • Year Built

    1926

  • $/SqFt

    $1,415

Virginia Heights - This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $2,990,000

Charming two-story home with a manicured front yard, stately columns, and a welcoming entrance at 1860 Via Contessa, Winter Park, FL 32789
View Details 51 Photos
Beautiful two-story home featuring a manicured lawn, classic black shutters, and elegant architectural details at 1860 Via Contessa, Winter Park, FL 32789
Inviting living room with neutral sofas, stylish wood accent wall, and bright natural light at 1860 Via Contessa, Winter Park, FL 32789
Elegant dining room featuring a modern light fixture, wood accent wall, and seating for six at 1860 Via Contessa, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 19 Days

  • Bedrooms

    8

  • Full Bath(s)

    6

  • Sq. Ft.

    7000

  • Year Built

    2003

  • $/SqFt

    $427

Lugano Terrace - One or more photo(s) has been virtually staged. 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 20 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 20 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 $729,000

Reduced By $20,000

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 19 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1527

  • Year Built

    1953

  • $/SqFt

    $477

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 $5,700,000

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 21 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6406

  • Year Built

    2024

  • $/SqFt

    $890

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

Pended $2,495,000

Charming two-story home with striped awnings, lush landscaping, and American flag on display at sunset at 140 Cortland Ave, Winter Park, FL 32789
View Details 28 Photos
Charming home with black and white striped awnings and a well manicured lawn at dusk at 140 Cortland Ave, Winter Park, FL 32789
Charming home with an American flag, striped awnings, and a brick walkway at 140 Cortland Ave, Winter Park, FL 32789
Bright entryway featuring hardwood floors, a staircase with white railing, and elegant decor at 140 Cortland Ave, Winter Park, FL 32789
On Market For 10 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    4168

  • Year Built

    1926

  • $/SqFt

    $599

Cortland Park - You’ll love the inviting ambiance of both this home and its vibrant Winter Park location. FLAT FEE MLS REALTY.

Home For Sale $2,399,900

Reduced By $100,000

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
Lakeside home with a private boat dock, jet ski, and manicured lawn at 301 Rippling Ln, Winter Park, FL 32789
Beautiful backyard with a sparkling pool, outdoor seating, and lush green lawn 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 21 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3694

  • Year Built

    1958

  • $/SqFt

    $650

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

Home For Sale $925,000

Charming single-story home boasts a well-manicured lawn, mature trees, and stylish mid-century modern architectural features at 625 Worthington Dr, Winter Park, FL 32789
View Details 42 Photos
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 21 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2133

  • Year Built

    1958

  • $/SqFt

    $434

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 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 22 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 22 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 22 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 $539,990

Reduced By $10,010

Charming two-story home with a covered front porch and blue exterior and well manicured landscaping at 423 Ololu Dr, Winter Park, FL 32789
View Details 24 Photos
A bright and inviting blue home, showcasing a large covered porch and outdoor features at 423 Ololu Dr, Winter Park, FL 32789
A bright entryway features wood-look tile flooring, fresh paint and modern light fixture at 423 Ololu Dr, Winter Park, FL 32789
Modern kitchen featuring quartz countertops, new stainless steel appliances, and stylish pendant lighting at 423 Ololu Dr, Winter Park, FL 32789
On Market For 22 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1920

  • Year Built

    1981

  • $/SqFt

    $281

Contact us today for a private showing. AAA GLOBAL VENTURES PA.

Pended $399,900

Charming home with a carport and a beautifully landscaped front yard with lush green grass at 767 Baffie Ave, Winter Park, FL 32789
View Details 25 Photos
Eat-in kitchen featuring white cabinets, an island, terracotta tile floors, and views of the backyard at 767 Baffie Ave, Winter Park, FL 32789
Spacious kitchen with terracotta tile floors, white cabinetry, black appliances, and a door to the backyard at 767 Baffie Ave, Winter Park, FL 32789
Bright dining area with terracotta tile floors, a round table, and a large window with views of the yard at 767 Baffie Ave, Winter Park, FL 32789
On Market For 22 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1132

  • Year Built

    1958

  • $/SqFt

    $353

Combining the perfect blend of modern updates and original character, this home is a must-see in the heart of Winter Park! GECKO REALTY, INC.

Home For Sale $1,350,000

Charming home featuring a circular brick driveway, manicured landscaping, and a bright white exterior at 181 N Phelps Ave, Winter Park, FL 32789
View Details 50 Photos
Inviting front porch featuring a stylish door, sleek black shutters and a cozy seating area at 181 N Phelps Ave, Winter Park, FL 32789
Aerial view of a home featuring a long rectangular pool and mature landscaping at 181 N Phelps Ave, Winter Park, FL 32789
Backyard pool area with cabana, dining table, and lush greenery at 181 N Phelps Ave, Winter Park, FL 32789
On Market For 23 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3000

  • Year Built

    1948

  • $/SqFt

    $450

Sylvan Lake Shores - Additional House Benefits include: Remodeled living room ; Original wood fireplace ; New AC (2021) ; Tankless water heater 2021 ; Dual masters ; 4 full baths ; Insulated 2 car garage with exAC Garage ; New vinyl flooring ; Remodeled office / guest room with built-in cabinets ; Heated swimming pool ; Renovated backyard with artificial grass and summer kitchen (outdoor furniture negotiable) ; New detached office space w/ air conditioning ; Outdoor ambient lighting ; New alarm system ; All appliances will stay ; Extended Kitchen Island ; New sprinkler system ; Outdoor shed storage; Acclimate Attic ; New PVC Wood Deck ; Water filtration system in the kitchen ; Underground gas line for stovetop, water heater, and pool heater Located just minutes from Windsong, Park Avenue, Baldwin Park, top-rated schools (Brookshire, Glenridge, WPHS), parks, dining, and shopping, this home offers both charm and convenience. ORLANDO BROTHERS REAL ESTATE LLC.

Home For Sale $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 26 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 84 Photos
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 26 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 $1,595,000

Charming pink home featuring a gated entryway, manicured landscaping, and a classic architectural design with white columns at 335 Beloit Ave, Winter Park, FL 32789
View Details 32 Photos
Charming pink home featuring stately white columns, a landscaped front yard, and tropical palm trees at 335 Beloit Ave, Winter Park, FL 32789
Welcoming foyer with neutral tile floors and chic decor that flows into the spacious living area at 335 Beloit Ave, Winter Park, FL 32789
Bright living room with a decorative fireplace, modern furnishings, and access to outdoor living space at 335 Beloit Ave, Winter Park, FL 32789
On Market For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2420

  • Year Built

    1978

  • $/SqFt

    $659

Enjoy a NEW A/C unit (2024), new washer/dryer (2024), and one of the best locations in the City of Winter Park! ! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,195,000

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 28 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
Elegant foyer featuring arched entryways, a dark wood front door, neutral paint and travertine tile flooring at 1690 Oneco Ave, Winter Park, FL 32789
On Market For 27 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2703

  • Year Built

    1967

  • $/SqFt

    $442

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

Home For Sale $795,000

Charming single-story home with a white exterior, gray shutters, and a well-maintained front yard at 1037 N Virginia Ave, Winter Park, FL 32789
View Details 39 Photos
Lovely single-story house with a white exterior, attached garage, and green grass at 1037 N Virginia Ave, Winter Park, FL 32789
Beautiful single-story home featuring a white exterior, covered porch, and well-manicured landscaping at 1037 N Virginia Ave, Winter Park, FL 32789
Inviting covered front porch with decorative iron supports and black front door at 1037 N Virginia Ave, Winter Park, FL 32789
On Market For 27 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1101

  • Year Built

    1960

  • $/SqFt

    $722

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

Pended $425,000

Charming blue home featuring a landscaped front yard, carport, and inviting curb appeal at 328 Lake Fair Ln, Winter Park, FL 32789
View Details 69 Photos
Inviting front entrance with a quaint bench, lush landscaping, and vibrant blue exterior paint at 328 Lake Fair Ln, Winter Park, FL 32789
A close-up of the home's front door, featuring a dark finish and wood post accents at 328 Lake Fair Ln, Winter Park, FL 32789
Bright dining room with hardwood floors, modern fan, and view to adjacent rooms at 328 Lake Fair Ln, Winter Park, FL 32789
On Market For 27 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1485

  • Year Built

    1958

  • $/SqFt

    $286

Fairbanks Shores - Don’t miss the chance to own this lakefront gem—a perfect blend of historic charm, modern upgrades, and an unbeatable location. Schedule your private tour today! RE/MAX 200 REALTY.

Home For Sale $1,250,000

Charming single-story home featuring a red tile roof, mature landscaping, and an attached garage at 1585 Chestnut Ave, Winter Park, FL 32789
View Details 45 Photos
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 26 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2220

  • Year Built

    1959

  • $/SqFt

    $563

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

Pended $949,900

Charming home with a well-manicured lawn, lush landscaping, and a welcoming two-car garage at 533 Balmoral Rd, Winter Park, FL 32789
View Details 39 Photos
Inviting front entrance with a lush, verdant pergola, and a security system at 533 Balmoral Rd, Winter Park, FL 32789
Up-close view of a stunning wooden front door surrounded by lush greenery and stone accents at 533 Balmoral Rd, Winter Park, FL 32789
Cozy covered patio featuring wood-look tile flooring, a unique chair, and ample natural light at 533 Balmoral Rd, Winter Park, FL 32789
On Market For 28 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1900

  • Year Built

    1957

  • $/SqFt

    $500

Upgrades include: New Paint & Finishes, Modernized Bathrooms (New vanities and a renovated master shower) Custom Master Closet, New Interior Doors and windows, New Upgraded HVAC System (2021), Tankless gas hot water heater, Roof (2020), HVAC (2021) Exterior Stone Façade, Updated Landscaping & Outdoor Living spaces (Lanai, pergola, and firepit) irrigation, New Front Door & Exterior Lighting, Solar Panels (paid off) Security System Ready (Wired for easy setup) Upgraded Laundry Room (Added storage, tile, and cabinetry) CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $2,395,000

Contemporary two-story home featuring a two-car garage and well-manicured landscaping at 2412 Chantilly Ave, Winter Park, FL 32789
View Details 48 Photos
Modern home showcases a two-car garage, gravel driveway, and lush, green landscaping at 2412 Chantilly Ave, Winter Park, FL 32789
Elegant entryway featuring a modern glass door, stone path, and stylish landscaping at 2412 Chantilly Ave, Winter Park, FL 32789
Bright foyer with hardwood floors and a modern glass door leading to the exterior at 2412 Chantilly Ave, Winter Park, FL 32789
On Market For 29 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4506

  • Year Built

    2024

  • $/SqFt

    $532

Winter Park Village - Perfectly positioned in a coveted Winter Park local, near top-rated schools and just moments from Park Avenue’s upscale shopping and dining, this exceptional residence offers the pinnacle of contemporary luxury living. COMPASS FLORIDA, LLC.

Pended $2,200,000

Stately two-story home boasts a clay tile roof, lush landscaping, and a long, curved driveway at 1446 Berkshire Ave, Winter Park, FL 32789
View Details 92 Photos
Stately two-story home boasts a clay tile roof, lush landscaping, and a long, curved driveway at 1446 Berkshire Ave, Winter Park, FL 32789
Close up shows the home's architectural details and manicured landscaping with towering palms at 1446 Berkshire Ave, Winter Park, FL 32789
Charming facade features a secure gated entry, arched windows, and an attached two-car garage at 1446 Berkshire Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 31 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4612

  • Year Built

    1925

  • $/SqFt

    $477

With its prime Winter Park location, exceptional privacy, and resort-style amenities, this remarkable home offers the perfect blend of style, comfort, and convenience in one of Winter Park’s most desirable neighborhoods. SERHANT.

Home For Sale $1,295,000

Inviting single-story home with a white exterior, well-manicured landscaping, and a large shade tree at 1932 Temple Dr, Winter Park, FL 32789
View Details 55 Photos
Inviting single-story home with a white exterior, well-manicured landscaping, and a large shade tree at 1932 Temple Dr, Winter Park, FL 32789
Charming single-story home with lush landscaping and a grand shade tree at twilight at 1932 Temple Dr, Winter Park, FL 32789
Bright and airy living room featuring a large white sectional, wood floors, and an open layout at 1932 Temple Dr, Winter Park, FL 32789
On Market For 33 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2432

  • Year Built

    1952

  • $/SqFt

    $532

Lake Knowles Terrace - A great investment opportunity to live among the finest homes in Winter Park and in well-established neighborhood providing a lifestyle like no other. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $534,900

Charming two-story home features a manicured lawn, long driveway, and inviting front entrance at 1481 Harmon Ave, Winter Park, FL 32789
View Details 31 Photos
Inviting two-story home with a well-kept lawn and quaint pathway leading to the front porch at 1481 Harmon Ave, Winter Park, FL 32789
Welcoming front porch featuring fresh exterior paint and bright windows at 1481 Harmon Ave, Winter Park, FL 32789
Bright living room with hardwood floors, white walls, and decorative furnishings at 1481 Harmon Ave, Winter Park, FL 32789
On Market For 34 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1900

  • Year Built

    1926

  • $/SqFt

    $282

Lawndale - Don’t miss out on this rare opportunity—schedule your private showing today! KELLER WILLIAMS WINTER PARK.

Home For Sale $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 37 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.

Pended $3,130,000

Modern two-story home with gray brick exterior, two-car garage, and a paved driveway at 210 E Lake Sue Ave, Winter Park, FL 32789
View Details 46 Photos
Stunning contemporary home at night, featuring gray brick and a landscaped yard at 210 E Lake Sue Ave, Winter Park, FL 32789
Modern front entry with glass door, gray brick, and landscaping at 210 E Lake Sue Ave, Winter Park, FL 32789
Elegant entryway with wood floors, high ceilings, and built-in wet bar at 210 E Lake Sue Ave, Winter Park, FL 32789
On Market For 38 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4188

  • Year Built

    2025

  • $/SqFt

    $747

Charmont - Schedule your private showing today and experience the epitome of luxury Winter Park living. COMPASS FLORIDA, LLC.

Home For Sale $1,895,000

Reduced By $100,000

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 38 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3971

  • Year Built

    1990

  • $/SqFt

    $477

College Place - Don't miss the opportunity to schedule a private viewing of this unique, one-of-a-kind treasure! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,279,000

Charming two-story home featuring a tile roof, a pergola over the garage, and a lush landscaped yard at 141 Oakwood Way, Winter Park, FL 32789
View Details 58 Photos
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 40 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3909

  • Year Built

    2015

  • $/SqFt

    $583

Charmont - This is more than a home—it’s an expression of refined living and timeless design. Schedule your private tour today! MAINFRAME REAL ESTATE.

Home For Sale $2,119,000

Two-story modern home with light-colored facade, wood garage doors, and landscaping at 785 N Phelps Ave, Winter Park, FL 32789
View Details 5 Photos
Modern kitchen with white cabinets, a large island, and stainless steel appliances at 785 N Phelps Ave, Winter Park, FL 32789
Spacious living area featuring a sectional sofa and a large TV at 785 N Phelps Ave, Winter Park, FL 32789
Bright bedroom with a comfortable bed and access to the backyard at 785 N Phelps Ave, Winter Park, FL 32789
On Market For 39 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    2964

  • Year Built

    2025

  • $/SqFt

    $715

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

Pended $2,100,000

Brick house with a metal roof, lush landscaping, and a brick walkway at 140 Dana Way, Winter Park, FL 32789
View Details 46 Photos
Brick walkway, lush landscaping and a charming house exterior at 140 Dana Way, Winter Park, FL 32789
Brick house with metal roof, landscaping, and a gravel driveway at 140 Dana Way, Winter Park, FL 32789
Housetop view showing the home's size and lot in a wooded area at 140 Dana Way, Winter Park, FL 32789
On Market For 40 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    3441

  • Year Built

    2011

  • $/SqFt

    $610

Charmont - The gated driveway and fully fenced property ensure security and exclusivity, all within one of Winter Park’s most sought-after neighborhoods.This is a rare opportunity to own a luxurious estate in a prestigious Winter Park location, surrounded by the beauty of the Lake Sue neighborhodd and just moments from the best shopping, dining, and cultural experiences the area has to offer. OLDE TOWN BROKERS INC.

Home For Sale $1,850,000

Reduced By $100,000

Two-story house with white exterior, gray roof, and landscaped lawn at 1470 Place Picardy, Winter Park, FL 32789
View Details 27 Photos
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 40 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4227

  • Year Built

    2003

  • $/SqFt

    $438

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

Viewing HOMES 1 to 50 of 130

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 954 439 6446 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$526,467
$428,950
134
1.5%
49.3%
87

Apopka
$532,144
$463,990
561
1.2%
49.2%
89

Belle Isle
$860,440
$704,950
26
0.0%
50.0%
74

Casselberry
$453,022
$435,000
87
2.3%
50.6%
68

Celebration
$1,439,199
$1,190,000
47
0.0%
46.8%
123

Champions Gate
$711,952
$700,000
19
0.0%
52.6%
261

Chuluota
$745,880
$600,000
20
0.0%
55.0%
47

Clermont
$574,680
$493,652
657
0.8%
48.7%
84

Gotha
$965,905
$649,990
13
0.0%
30.8%
55

Groveland
$483,658
$419,000
251
0.8%
51.0%
85

Harmony
$440,867
$412,900
67
0.0%
31.3%
93

Kissimmee
$515,796
$440,000
2327
1.5%
47.6%
102

Longwood
$748,265
$550,000
181
0.6%
53.0%
86

Maitland
$800,061
$596,900
74
1.4%
48.6%
91

Minneola
$559,550
$534,613
124
0.8%
37.9%
92

Montverde
$1,538,313
$1,100,519
51
0.0%
49.0%
138

Ocoee
$528,647
$469,990
179
2.2%
51.4%
83

Orlando
$688,228
$485,000
2703
1.7%
47.4%
81

Oviedo
$726,816
$626,450
182
1.6%
44.0%
79

Poinciana
$332,039
$315,000
257
0.8%
57.6%
134

Reunion
$1,810,711
$1,249,900
101
1.0%
45.5%
161

Saint Cloud
$552,659
$464,990
595
1.0%
70.1%
152

Sanford
$521,660
$415,000
391
1.0%
51.7%
97

Sorrento
$582,734
$456,500
106
1.9%
67.9%
89

Windermere
$2,113,295
$1,295,000
255
0.4%
43.9%
111

Winter Garden
$844,296
$693,000
578
0.5%
48.4%
86

Winter Springs
$586,818
$474,999
121
0.8%
40.5%
75

EasyStreet

Call to Schedule a Showing

(954) 439-6446

(954) 439-6446