321 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $2,295,000

On Market Today
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3005

  • Year Built

    2026

  • $/SqFt

    $764

Discover the unmatched quality and comfort of new construction living in a home designed to elevate your everyday experience. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $2,100,000

Charming two-story home with manicured lawn, stone accents, and professionally landscaped yard at 2402.5 Temple Dr, Winter Park, FL 32789
Beautifully landscaped home with lush green lawn, elegant shrubs, and tranquil twilight view at 2402.5 Temple Dr, Winter Park, FL 32789
Inviting front porch with stone columns, manicured hedges, and stylish entryway at 2402.5 Temple Dr, Winter Park, FL 32789
On Market For 2 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3248

  • Year Built

    2015

  • $/SqFt

    $647

Call today for an easy showing! OLDE TOWN BROKERS INC.

Home For Sale $1,450,000

Aerial view of a well-maintained single-story home with a lush green lawn, mature trees, and a brick driveway at 2105 Fosgate Dr, Winter Park, FL 32789
Bright kitchen with stainless steel appliances, farmhouse sink, patterned backsplash, and custom vent hood at 2105 Fosgate Dr, Winter Park, FL 32789
Spacious kitchen with a large island, pendant lighting, stainless steel appliances, and custom wood accents at 2105 Fosgate Dr, Winter Park, FL 32789
On Market Today
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3068

  • Year Built

    1956

  • $/SqFt

    $473

All Double Pane Aluminum Windows throughout home. LPT REALTY, LLC.

Home For Sale $699,000

Close-up of the address numbers and a decorated welcome sign on the entrance gate at 2711 Parkland Dr, Winter Park, FL 32789
A serene outdoor space with a pergola-covered walkway adorned with potted plants and flowers at 2711 Parkland Dr, Winter Park, FL 32789
Spacious living room featuring a fireplace, ceiling fan, and large window for ample natural light at 2711 Parkland Dr, Winter Park, FL 32789
On Market Today
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1618

  • Year Built

    1938

  • $/SqFt

    $432

Parklando - This exceptional home offers the quintessential Winter Park lifestyle in a location that combines established neighborhood character with exciting urban accessibility. CORCORAN PREMIER REALTY.

Pended $300,000

*POTENTIAL GREAT VALUE
On Market For 1 Day
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1611

  • Year Built

    1980

  • $/SqFt

    $186

Cedar Ridge - Pool and layout offer a solid foundation for something truly special! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,165,000

A grand entrance with double doors, decorative plants, and stylish lighting fixtures creates curb appeal at 2832 Bear Island Pointe, Winter Park, FL 32792
Landscaped lawn with palm trees at the entrance of a cream colored stucco home with a dark colored roof at 2832 Bear Island Pointe, Winter Park, FL 32792
Lovely home featuring manicured shrubs and a circular driveway, offering both beauty and convenience at 2832 Bear Island Pointe, Winter Park, FL 32792
On Market For 5 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3983

  • Year Built

    1999

  • $/SqFt

    $292

Experience the best of Winter Park living in this exceptional home. Schedule your private showing today. COMPASS FLORIDA LLC.

Home For Sale $839,900

Charming single-story home with a manicured lawn, brick driveway, and two-car garage at 2168 Marsh Sedge Ln, Winter Park, FL 32792
Inviting entryway with stone accents and a charming blue front door with sidelight at 2168 Marsh Sedge Ln, Winter Park, FL 32792
Stylish foyer featuring sleek tile flooring and a decorative console table, creating a welcoming entrance at 2168 Marsh Sedge Ln, Winter Park, FL 32792
On Market For 5 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2192

  • Year Built

    2019

  • $/SqFt

    $383

Preserve At Hawks Crest - Don’t miss this opportunity—schedule your private showing today! SELECTA REALTY LLC.

Home For Sale $649,900

Charming home featuring light green siding, white trim, and a well-manicured lawn with beautiful, mature landscaping at 236 N Ranger Blvd, Winter Park, FL 32792
Modern kitchen boasting an expansive island with seating, stainless steel appliances, and stylish backsplash at 236 N Ranger Blvd, Winter Park, FL 32792
Open kitchen featuring a large island with seating, stainless steel appliances, and a stunning backsplash at 236 N Ranger Blvd, Winter Park, FL 32792
On Market For 4 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1844

  • Year Built

    1963

  • $/SqFt

    $352

Winter Park Pines - This is your opportunity to live in a thoughtfully renovated home in a community that offers both serenity and vibrant activity, right outside your doorstep. EXP REALTY LLC.

Pended $585,000

Inviting front porch with a decorative door wreath and cozy seating area with stylish chairs at 2441 Banchory Rd, Winter Park, FL 32792
Bright open kitchen featuring white cabinetry, stainless steel appliances, and hardwood floors at 2441 Banchory Rd, Winter Park, FL 32792
Modern kitchen with stainless steel appliances, quartz countertops, and a light blue backsplash at 2441 Banchory Rd, Winter Park, FL 32792
On Market For 3 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1630

  • Year Built

    1960

  • $/SqFt

    $359

Don’t miss this incredible opportunity to make this house your home! FANNIE HILLMAN & ASSOCIATES.

Pended $459,999

Enclosed patio has an outdoor dining set with a hot tub and pool visible at 5326 Lanyard Ct, Winter Park, FL 32792
Covered patio features a dining table, chairs, and a relaxing hot tub for outdoor enjoyment at 5326 Lanyard Ct, Winter Park, FL 32792
Relaxing covered patio complete with comfortable seating, grill, and an egg chair at 5326 Lanyard Ct, Winter Park, FL 32792
On Market For 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1634

  • Year Built

    1973

  • $/SqFt

    $282

Woodcrest - Nestled in vibrant Winter Park, you’re minutes from top-rated schools, charming boutiques, gourmet dining, and scenic parks. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $1,495,000

Landscaped front yard featuring a circular driveway and mature magnolia tree providing ample shade at 1644 Hibiscus Ave, Winter Park, FL 32789
Well-maintained single-story home with a large front lawn, circular driveway, and carefully manicured landscaping at 1644 Hibiscus Ave, Winter Park, FL 32789
Exterior shot of a home showcasing a circular driveway, well-manicured lawn, and mature trees at 1644 Hibiscus Ave, Winter Park, FL 32789
On Market For 6 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2145

  • Year Built

    1974

  • $/SqFt

    $697

Flora Park - This is more than a home—it's an opportunity to live in one of Winter Park's most iconic neighborhoods. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $1,275,000

Charming single-story brick home featuring a well-manicured lawn and an attached two-car garage at 309 Park North Ct, Winter Park, FL 32789
Inviting home entrance with a decorative double door, brick pathway, and manicured landscaping at 309 Park North Ct, Winter Park, FL 32789
Spacious living room featuring neutral tile flooring, recessed lighting, and a view to the backyard at 309 Park North Ct, Winter Park, FL 32789
On Market For 6 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3096

  • Year Built

    1968

  • $/SqFt

    $412

Schedule your private showing today and explore the possibilities! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,025,000

Well-appointed kitchen with an island, dark wood cabinetry, stainless steel appliances, and hardwood floors at 2923 Cove Trl, Winter Park, FL 32789
Spacious home office with hardwood floors, built-in shelving, and ample desk space for productivity at 2923 Cove Trl, Winter Park, FL 32789
Temperature-controlled wine cellar featuring custom shelving and storage for an extensive collection at 2923 Cove Trl, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3377

  • Year Built

    1964

  • $/SqFt

    $304

*CLICK on Virtual tour link for 3D Walk Through. * KELLER WILLIAMS ADVANTAGE III.

Pended $975,000

Charming single story home with paver driveway, manicured lawn, and a well-maintained landscape at 1265 Park Pointe Ln, Winter Park, FL 32789
Inviting entryway featuring wood columns, a welcoming front door, and a well-kept stone walkway at 1265 Park Pointe Ln, Winter Park, FL 32789
Bright and spacious living room with hardwood floors, a ceiling fan, and an open floor plan at 1265 Park Pointe Ln, Winter Park, FL 32789
On Market For 4 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2295

  • Year Built

    1989

  • $/SqFt

    $425

**Sellers will contribute $3,000 to a buyers closing costs with an accepted full price offer** KELLER WILLIAMS ADVANTAGE III.

Home For Sale $800,000

Stunning pool area surrounded by lush landscaping and a brick paver deck, perfect for outdoor entertaining and relaxation at 600 Brechin Dr, Winter Park, FL 32792
Inviting living room featuring hardwood floors, a ceiling fan, a neutral color palette, and lots of natural light at 600 Brechin Dr, Winter Park, FL 32792
Bright living room with hardwood floors, a ceiling fan, neutral decor, and ample natural light from a large window at 600 Brechin Dr, Winter Park, FL 32792
On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2360

  • Year Built

    1962

  • $/SqFt

    $339

Roof - 2013 Hvac - 2013 Electrical Updates - 2013 Plumbing - 2022 Water Heater - 2022 KELLER WILLIAMS WINTER PARK.

Home For Sale $670,000

Coverage sheet including square footage for 3006 Northwood Blvd showing setbacks and square footage coverage at 3006 Northwood Blvd, Winter Park, FL 32789
This document details minimum setbacks allowed for the property and also lists existing setbacks at 3006 Northwood Blvd, Winter Park, FL 32789
Survey shows property lines, landscaping, and the location of the home at 3006 Northwood Blvd at 3006 Northwood Blvd, Winter Park, FL 32789
On Market For 6 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1729

  • Year Built

    1953

  • $/SqFt

    $388

Northwood Terrace - Enjoy walking distance to local favorites like East End Market, Kelly’s Ice Cream, Redlight Redlight, and Sushi Lola. ORLANDO HOMES GROUP LLC.

Home For Sale $498,000

Charming home featuring a brick driveway, lovely yard, and inviting facade with a carport at 808 Denton Rd, Winter Park, FL 32792
Charming home featuring a brick driveway, lovely yard, and inviting facade with a carport at 808 Denton Rd, Winter Park, FL 32792
Inviting entryway with natural wood door, tiled flooring and stylish wall mirror at 808 Denton Rd, Winter Park, FL 32792
On Market For 6 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1740

  • Year Built

    1961

  • $/SqFt

    $286

Winter Park Estates - With its timeless style, modern updates and natural beauty, this home is a one-of-a-kind gem. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,150,000

Charming two-story home showcasing a beautifully landscaped front yard and a striking red front door at 795 W Canton Ave, Winter Park, FL 32789
Aerial view of the home featuring a well-manicured lawn and mature landscaping at 795 W Canton Ave, Winter Park, FL 32789
Charming two-story home featuring a striking red front door and professionally landscaped front yard at 795 W Canton Ave, Winter Park, FL 32789
On Market For 7 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2374

  • Year Built

    2017

  • $/SqFt

    $484

Don't miss this rare opportunity to own a modern gem in one of Central Florida’s most sought-after neighborhoods! WEICHERT REALTORS HALLMARK PROPERTIES.

Home For Sale $1,100,000

Spacious dining area featuring a black brick accent wall and modern furnishings at 913 Moss Ln, Winter Park, FL 32789
Cozy living room with stylish decor, modern furniture, and sheer curtains at 913 Moss Ln, Winter Park, FL 32789
Open kitchen with stainless steel appliances, white cabinets, and a breakfast bar at 913 Moss Ln, Winter Park, FL 32789
On Market For 7 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1887

  • Year Built

    1953

  • $/SqFt

    $583

Schools: Zoned for top-rated schools, including Dommerich Elementary, Maitland Middle, and Winter Park High School. FLAT FEE MLS REALTY.

Home For Sale $780,000

Spacious two story home with solar panels, lush lawn, and a two-car garage at 5275 Pine Lily Cir, Winter Park, FL 32792
Hallway with tiled floor, console table with decor and a view of the living room at 5275 Pine Lily Cir, Winter Park, FL 32792
Inviting living room featuring tile floors, a ceiling fan, comfortable seating and a view of the kitchen and dining area at 5275 Pine Lily Cir, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 7 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3152

  • Year Built

    2014

  • $/SqFt

    $247

Sanctuary At Aloma - Don’t miss your chance to call this place home! RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $499,000

Charming home featuring a cozy front porch and well-maintained landscaping at 3601 Midiron Dr, Winter Park, FL 32789
Fenced side yard with a grill, utility connections, and mature landscaping at 3601 Midiron Dr, Winter Park, FL 32789
Back yard with patio area, perfect for outdoor dining and relaxing at 3601 Midiron Dr, Winter Park, FL 32789
On Market For 7 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    954

  • Year Built

    1945

  • $/SqFt

    $523

Golfview - Schedule your showing and don't miss this incredible opportunity! EMPIRE NETWORK REALTY.

Home For Sale $2,575,000

Beautiful front entrance with a stone walkway, manicured landscaping, and a stylish modern door at 1795 Greenwich Ave, Winter Park, FL 32789
Bright and airy living room with a comfortable gray sectional, wood floors, and access to the outdoors at 1795 Greenwich Ave, Winter Park, FL 32789
Stylish living room showcasing a modern fireplace, comfortable seating, and large windows at 1795 Greenwich Ave, Winter Park, FL 32789
On Market For 7 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3852

  • Year Built

    2019

  • $/SqFt

    $668

Zoned for top-rated Winter Park schools (Brookshire, Glenridge, Winter Park High) and near private schools- Lake Highland Prep, Park Maitland, Geneva School and more KELLY PRICE & COMPANY LLC.

Pended $749,000

Inviting front entrance of a brick home with a well-kept lawn and neatly trimmed hedges at 2907 Summerfield Rd, Winter Park, FL 32792
Exterior showcasing a well-maintained two-car garage and manicured front yard with healthy green bushes at 2907 Summerfield Rd, Winter Park, FL 32792
Classic home with brick facade, blue shutters, and a neatly landscaped front yard with mature trees at 2907 Summerfield Rd, Winter Park, FL 32792
On Market For 8 Days
  • Bedrooms

    5

  • Full Bath(s)

    2

  • Sq. Ft.

    2532

  • Year Built

    1968

  • $/SqFt

    $296

Golfside - All this house needs is you! Come see this beauty today! MILLER GRANT AND COMPANY.

Home For Sale $1,299,000

Beautiful home featuring a brick driveway, lush lawn, and meticulous landscaping at 1341 Lyndale Blvd, Winter Park, FL 32789
Inviting front entryway with a stylish light fixture and elegant glass-paneled door at 1341 Lyndale Blvd, Winter Park, FL 32789
Elegant hallway features hardwood floors, archways, and modern chandelier at 1341 Lyndale Blvd, Winter Park, FL 32789
On Market For 8 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2388

  • Year Built

    2007

  • $/SqFt

    $544

Dixie Terrace - Located in a top-rated school district and are the corner from shops, restaurants, parks, and more, this home offers a lifestyle of comfort, charm, and convenience in one of Winter Park’s most sought-after neighborhoods. COMPASS FLORIDA LLC.

Home For Sale $709,000

A winding driveway leads to a beautifully landscaped home with a pop of color on the front door at 624 Dunraven Dr, Winter Park, FL 32792
Modern living room featuring a comfortable sofa, wood floors, and sliding glass doors to the outside at 624 Dunraven Dr, Winter Park, FL 32792
Bright kitchen featuring stainless steel appliances, granite countertops, and ample cabinet space at 624 Dunraven Dr, Winter Park, FL 32792
On Market For 8 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1762

  • Year Built

    1963

  • $/SqFt

    $402

Don't miss your opportunity to live in this amazing neighborhood, schedule your private showing now! COMPASS FLORIDA LLC.

Home For Sale $2,295,000

An inviting backyard with a sparkling pool, jacuzzi, outdoor fireplace, and ample lounging space at 2614 Parkland Dr, Winter Park, FL 32789
A captivating aerial view showcasing the home's backyard pool, patio, and impeccable landscaping at 2614 Parkland Dr, Winter Park, FL 32789
An aerial view displays the home's beautiful landscaping, unique driveway, and a tranquil setting at 2614 Parkland Dr, Winter Park, FL 32789
On Market For 9 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3307

  • Year Built

    2007

  • $/SqFt

    $694

Parklando - With a brand-new tile roof, all-natural gas appliances, and an unbeatable location, this home is the definition of elevated Winter Park living. JW GASTON LLC.

Home For Sale $3,850,000

Charming two-story home with manicured lawn, gray metal roof and blue shutters at 2171 Forrest Rd, Winter Park, FL 32789
Elegant foyer with hardwood floors, a chandelier, and a wood-framed glass door at 2171 Forrest Rd, Winter Park, FL 32789
Inviting sitting room with built-in bookshelves and comfortable seating at 2171 Forrest Rd, Winter Park, FL 32789
On Market For 12 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4565

  • Year Built

    2016

  • $/SqFt

    $843

This remarkable property offers the ultimate in refined living, combining luxury, comfort and convenience in one of Central Florida’s sought-after communities. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $3,195,000

Charming home entrance featuring a pergola with covered walkway, leading to the custom doors and lush landscaping at 1020 Mayfield Ave, Winter Park, FL 32789
Beautiful custom entryway with modern pergola and custom door design framed by manicured greenery at 1020 Mayfield Ave, Winter Park, FL 32789
Elegant front entrance with custom wood door framed by symmetrical landscaping and a neutral color palette at 1020 Mayfield Ave, Winter Park, FL 32789
On Market For 11 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2663

  • Year Built

    1989

  • $/SqFt

    $1,200

Kronenberger - Located just a short drive, walk, or bike ride from Park Avenue, this impeccable home is close to both Interlachen Country Club, the Winter Park Racquet Club, nearby shops and dining, Advent Health, and is zoned for the A-rated Lakemont/Maitland/WPHS school district. KELLY PRICE & COMPANY LLC.

Home For Sale $2,650,000

Contemporary home boasts a modern facade, two-car garage, manicured lawn, and an elegant design at 1700 Palm Ave, Winter Park, FL 32789
Aerial view of a modern home with a backyard oasis including a swimming pool, patio, and lush green lawn at 1700 Palm Ave, Winter Park, FL 32789
Outdoor kitchen featuring stainless steel appliances, marble counters, a wood ceiling, and a view of the pool at 1700 Palm Ave, Winter Park, FL 32789
On Market For 12 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3770

  • Year Built

    2016

  • $/SqFt

    $703

Winter Park Heights - Ideally located just blocks from Winter Park’s renowned shops, dining, YMCA, and AdventHealth Hospital—and zoned for top-rated schools—this home delivers elevated living in one of Central Florida’s most coveted neighborhoods. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,550,000

Inviting entrance with double wooden doors, white Adirondack chairs, and a circular brick walkway at 1661 Woodland Ave, Winter Park, FL 32789
Elegant foyer with marble floors, staircase with white railings, and a view of the living and dining areas at 1661 Woodland Ave, Winter Park, FL 32789
Spacious living area with hardwood floors, arched windows, a chaise lounge, and a dining table at 1661 Woodland Ave, Winter Park, FL 32789
On Market For 13 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3215

  • Year Built

    1948

  • $/SqFt

    $482

Comstock Park - This home blends elegance, comfort, and functionality—an entertainer’s dream with a fantastic flow for everyday living! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $750,000

Charming home featuring a stone accent garage, well maintained lawn, and mature trees at 1139 Fairway Dr, Winter Park, FL 32792
Inviting walkway to the front door surrounded by lush greenery and foliage at 1139 Fairway Dr, Winter Park, FL 32792
Bright hallway with natural light from the atrium and neutral decor at 1139 Fairway Dr, Winter Park, FL 32792
On Market For 12 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2385

  • Year Built

    1979

  • $/SqFt

    $314

Golfside - It’s a lifestyle. Come experience it for yourself! KELLER WILLIAMS WINTER PARK.

Pended $415,000

Beautiful home exterior with a brick facade, mature trees, and a well-maintained front yard creating a serene setting at 2024 Linden Road, Winter Park, FL 32792
Attractive brick home with manicured lawn, complemented by a brick driveway and mature trees, creating a welcoming ambiance at 2024 Linden Road, Winter Park, FL 32792
Close-up showcasing the charming brick facade and front door with brick paver walkway and landscaped accents at 2024 Linden Road, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 10 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1872

  • Year Built

    1972

  • $/SqFt

    $222

For those with a vision, this is your chance to transform this property into your own! PREMIER SOTHEBY'S INTL. REALTY.

Pended $1,795,000

Landscaped front yard featuring a modern two-story home with a two-car garage and beautiful curb appeal at 2813 Northwood Blvd, Winter Park, FL 32789
Bright foyer featuring a glass-paneled front door, hardwood floors, and modern decor at 2813 Northwood Blvd, Winter Park, FL 32789
Modern staircase with a unique hanging light fixture and natural light from a nearby window at 2813 Northwood Blvd, Winter Park, FL 32789
On Market For 8 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3444

  • Year Built

    2021

  • $/SqFt

    $521

Northwood Terrace - Experience the elegance and lifestyle this home offers and reach out today to arrange your private showing. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $679,000

Reduced By $20,900

Inviting entrance with meticulously maintained landscaping, creating a warm, secure entry at 2817 Prince John Rd, Winter Park, FL 32792
Bright kitchen featuring white cabinets, stainless steel appliances, and central island at 2817 Prince John Rd, Winter Park, FL 32792
Open-concept living area featuring a modern kitchen, dining area, and wood-look tile flooring at 2817 Prince John Rd, Winter Park, FL 32792
On Market For 13 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2183

  • Year Built

    1963

  • $/SqFt

    $311

Come visit this amazing, warm and friendly Winter Park neighborhood because you are sure to want to stay forever! LORI GILMORE REAL ESTATE LLC.

Home For Sale $525,000

This property features a brick facade, a two-car garage and beautifully maintained landscaping and driveway at 3306 Fishermans Cv, Winter Park, FL 32792
A charming single-story brick home boasts a well-kept lawn, manicured landscaping, and a welcoming entrance at 3306 Fishermans Cv, Winter Park, FL 32792
Well-maintained front yard featuring lush green grass, trimmed bushes, and a brick mailbox at 3306 Fishermans Cv, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 13 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2408

  • Year Built

    1985

  • $/SqFt

    $218

You will think the same as you take a tour. WEICHERT REALTORS HALLMARK PROPERTIES.

Pended $414,900

Cozy home with a covered carport and attractive landscaping, situated on a well-kept lot at 2743 Sanbina St, Winter Park, FL 32789
Bright living room with a neutral color palette, Terrazzo floors and stylish decor, creating a modern space at 2743 Sanbina St, Winter Park, FL 32789
Inviting living space with Terrazzo floors, featuring large windows and elegant furnishings for comfortable living at 2743 Sanbina St, Winter Park, FL 32789
On Market For 10 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1226

  • Year Built

    1960

  • $/SqFt

    $338

Howell Heights - Don’t miss your chance to call it yours! KELLER WILLIAMS WINTER PARK.

Pended $685,000

Home exterior with a large driveway, a well-maintained lawn, and a charming single-story facade at 1726 Sarong Pl, Winter Park, FL 32792
Inviting screened-in pool area with comfortable lounge chairs, offering a private outdoor retreat at 1726 Sarong Pl, Winter Park, FL 32792
Inviting pool area surrounded by a screened enclosure and complemented by comfortable lounge chairs at 1726 Sarong Pl, Winter Park, FL 32792
On Market For 11 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2636

  • Year Built

    2005

  • $/SqFt

    $260

Don’t miss the opportunity to show this stunning property to your most discerning buyer! KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $569,999

Charming single-story home featuring stucco, manicured landscaping, and attached garage at 7730 Broken Arrow Trl, Winter Park, FL 32792
Inviting single-story home with driveway and an attached garage and mature shade trees at 7730 Broken Arrow Trl, Winter Park, FL 32792
Attractive single-story home with well-maintained lawn and landscaping under the sunlight at 7730 Broken Arrow Trl, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 14 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2706

  • Year Built

    1971

  • $/SqFt

    $211

Arrowhead Cove - Don’t miss your chance to enjoy the comfort and tranquility of this unique property. LA ROSA REALTY PREMIER LLC.

Home For Sale $550,000

Inviting two-story home with a beautiful lawn, showcasing the front facade at 2227 Coventry Dr, Winter Park, FL 32792
Charming two-story home with a lush lawn, complemented by mature landscaping at 2227 Coventry Dr, Winter Park, FL 32792
Beautiful two-story home featuring a well-kept lawn and neat landscaping at 2227 Coventry Dr, Winter Park, FL 32792
On Market For 14 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2076

  • Year Built

    1970

  • $/SqFt

    $265

Don’t miss the opportunity to own this exceptional property! LPT REALTY, LLC.

Home For Sale $539,000

Beautiful home showcasing a lush green lawn, mature trees, and a concrete driveway leading to a two-car garage at 1157 Valley Creek Run, Winter Park, FL 32792
Close-up of the home's manicured landscaping, garden beds, and inviting front entrance with lots of natural light at 1157 Valley Creek Run, Winter Park, FL 32792
Aerial view of a charming home featuring mature trees, lush lawn, and a well-maintained exterior in a serene neighborhood at 1157 Valley Creek Run, Winter Park, FL 32792
On Market For 14 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2171

  • Year Built

    1995

  • $/SqFt

    $248

Lost Creek - APPRASIAL has been done, and the home is ready for a new owner! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $525,000

A single-story home with a screened-in porch and a concrete driveway surrounded by mature trees at 2507 Lafayette Ave, Winter Park, FL 32789
The side of the house with an exterior door, small window and trash bins along a stone path at 2507 Lafayette Ave, Winter Park, FL 32789
The home's backyard with lush green ground cover, trees, a grill, and a ladder at 2507 Lafayette Ave, Winter Park, FL 32789
On Market For 14 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    943

  • Year Built

    1956

  • $/SqFt

    $557

Winter Park Village - Your future of luxury living in Winter Park awaits on Lafayette Avenue. -- RE/MAX ASSURED.

Pended $8,995,000

Beautiful two-story home featuring a brick driveway, manicured landscaping, and a classic architectural style at 2001 Bett Mar Ln, Winter Park, FL 32789
Charming home with lush green landscaping, an inviting entrance, and a brick driveway leading up to the property at 2001 Bett Mar Ln, Winter Park, FL 32789
Elegant estate featuring a brick driveway, wrought iron gate, and mature trees surrounding the property at 2001 Bett Mar Ln, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 9 Days
  • Bedrooms

    8

  • Full Bath(s)

    8

  • Sq. Ft.

    8583

  • Year Built

    1995

  • $/SqFt

    $1,048

Green Oaks - Don’t miss this rare opportunity to claim this stunning residence as your own—schedule a private showing today to experience the unparalleled elegance and uniqueness of this extraordinary estate! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $3,490,000

Modern kitchen with marble island, sleek gray cabinetry, pendant lighting, and stainless steel appliances at 1910 Glencoe Rd, Winter Park, FL 32789
Bright living room with fireplace, custom built-ins, hardwood floors, and large windows at 1910 Glencoe Rd, Winter Park, FL 32789
Serene bedroom with a canopy bed, neutral decor, and a sliding glass door to the outdoors at 1910 Glencoe Rd, Winter Park, FL 32789
On Market For 15 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4205

  • Year Built

    2025

  • $/SqFt

    $830

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

Home For Sale $3,295,000

Close up view of the front entrance with modern design, black door and side lights at 532 Worthington Dr, Winter Park, FL 32789
Close up view of the front entrance with modern design, black door and side lights at 532 Worthington Dr, Winter Park, FL 32789
Open concept Living Room includes hardwood floors, large dining table, and direct access to the patio at 532 Worthington Dr, Winter Park, FL 32789
On Market For 15 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3974

  • Year Built

    2023

  • $/SqFt

    $829

Kenilworth Shores - You can make this home your new reality! FLORIDA ONE REAL ESTATE LLC.

Home For Sale $439,999

Beautiful single-story home featuring a freshly painted exterior, a well-kept lawn, and an attached garage at 2259 King Johns Ct, Winter Park, FL 32792
Close-up view of the home's lovely blue front door adorned with a wreath and stylish exterior lighting at 2259 King Johns Ct, Winter Park, FL 32792
Inviting living room with a comfortable sectional sofa, a modern coffee table, and a stylish entertainment center at 2259 King Johns Ct, Winter Park, FL 32792
On Market For 15 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1551

  • Year Built

    1969

  • $/SqFt

    $284

Winter Woods - This is a rare opportunity to own a move-in-ready home in one of Central Florida’s most sought-after neighborhoods. Schedule your showing today! ARK REALTY LLC.

Home For Sale $420,000

Backyard featuring a well maintained lawn, patio space and white siding at 3063 Ash Park Loop, Winter Park, FL 32792
Beautiful home with brick accents, a well-manicured lawn, and a black two-car garage at 3063 Ash Park Loop, Winter Park, FL 32792
Backyard featuring a well maintained lawn, patio space and white siding at 3063 Ash Park Loop, Winter Park, FL 32792
On Market For 14 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1673

  • Year Built

    1987

  • $/SqFt

    $251

The combination of modern updates, functional spaces, and neighborhood amenities, makes this home an attractive option for anyone seeking a comfortable and convenient lifestyle. ANDERSON INVESTMENT PROPERTIES.

Home For Sale $349,990

Charming single-story home featuring manicured shrubs and a concrete walkway at 320 Granada Dr, Winter Park, FL 32789
Spacious living room with hardwood floors and a cozy fireplace at 320 Granada Dr, Winter Park, FL 32789
Bright living room featuring hardwood floors and several windows for natural light at 320 Granada Dr, Winter Park, FL 32789
On Market For 15 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1401

  • Year Built

    1946

  • $/SqFt

    $250

Don’t miss the opportunity to own a piece of Winter Park charm! KELLER WILLIAMS WINTER PARK.

Home For Sale $1,150,000

Modern kitchen with white cabinetry, stainless steel appliances, and wood-look flooring at 2011 Soaring Oak Way, Winter Park, FL 32792
Close-up of modern kitchen featuring gray backsplash, stainless steel range hood and appliances at 2011 Soaring Oak Way, Winter Park, FL 32792
Stainless steel kitchen appliances with view of dining area featuring window views at 2011 Soaring Oak Way, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 16 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4307

  • Year Built

    2021

  • $/SqFt

    $267

Waters Edge At Hawks Crest - Don't miss your opportunity to live in one of the newest and most desirable communities in Winter Park. Schedule your showing today! DEGREE REALTY LLC.

Home For Sale $595,000

Landscaped front yard with mature tree, a driveway leading to a garage, and a well-maintained lawn at 1821 Goodrich Ave, Winter Park, FL 32789
Well-maintained front yard with a mature tree, a long driveway, and partial view of the cozy home at 1821 Goodrich Ave, Winter Park, FL 32789
Functional kitchen featuring bright yellow cabinetry, white appliances, and stylish tiled backsplash at 1821 Goodrich Ave, Winter Park, FL 32789
On Market For 16 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1000

  • Year Built

    1955

  • $/SqFt

    $595

Sylvan Heights - Note: no house showings prior to entering into an acceptable contract and having access during the inspection period, as value is in the land. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $650,000

Home exterior featuring an attached two car garage and manicured lawn at 2855 Lion Heart Rd, Winter Park, FL 32792
View of entryway with pendant lighting and decorative console table at 2855 Lion Heart Rd, Winter Park, FL 32792
Open floor plan with living room flowing into dining area and kitchen at 2855 Lion Heart Rd, Winter Park, FL 32792
On Market For 13 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1727

  • Year Built

    1963

  • $/SqFt

    $376

Located on a quiet, tree-lined street with sidewalks for walking or biking, zoned for highly rated Winter Park schools, and with an optional HOA, this property is a perfect choice for families, professionals, or investors alike. MY REALTY GROUP, LLC..

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 407-278-2057 and speak with one of our real estate consultants.

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