302 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $650,000

Charming single story home featuring manicured lawn and mature landscaping at 2855 Lion Heart Rd, Winter Park, FL 32792
View Details 33 Photos
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 Today

  • 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..

Home For Sale $384,900

Charming single-story home with a well-manicured lawn, vibrant landscaping, and inviting curb appeal at 7543 Dockside St, Winter Park, FL 32792
View Details 34 Photos
Inviting single-story home featuring a lush green lawn, mature trees, and a well-maintained exterior at 7543 Dockside St, Winter Park, FL 32792
Bird's eye view of home featuring mature landscaping, green lawn, a driveway and a neutral color scheme at 7543 Dockside St, Winter Park, FL 32792
Aerial view of backyard featuring mature landscaping, fenced in yard and a concrete patio at 7543 Dockside St, Winter Park, FL 32792
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1434

  • Year Built

    1973

  • $/SqFt

    $268

Woodcrest - Past the porch you have a sizable back yard for gardening and or entertaining. Bring your offers! ! LPT REALTY, LLC.

Home For Sale $675,000

Charming two-story townhouse featuring an attached garage and mature landscaping at 796 Mcintyre Ave, Winter Park, FL 32789
View Details 42 Photos
Stylish two-story townhouse showcasing a well-manicured yard and inviting curb appeal at 796 Mcintyre Ave, Winter Park, FL 32789
Welcoming front entryway with a decorative red door and attractive landscaping at 796 Mcintyre Ave, Winter Park, FL 32789
Quiet street view showcasing beautiful brick-paved road and mature trees at 796 Mcintyre Ave, Winter Park, FL 32789
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1910

  • Year Built

    1988

  • $/SqFt

    $353

Zoned for Audubon K-8 and Winter Park High School. Welcome home! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $625,000

Charming one-story home with a well-manicured lawn and inviting curb appeal at 2707 Prince John Rd, Winter Park, FL 32792
View Details 30 Photos
Inviting backyard pool featuring ample patio space, landscaping, and a storage shed at 2707 Prince John Rd, Winter Park, FL 32792
Open-concept kitchen with stainless steel appliances and hardwood flooring at 2707 Prince John Rd, Winter Park, FL 32792
Modern kitchen featuring white cabinets, stainless steel appliances, and a kitchen island at 2707 Prince John Rd, Winter Park, FL 32792
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1670

  • Year Built

    1962

  • $/SqFt

    $374

Roof - 2022 Hvac - 2022 Plumbing - 2016 Water Heater - 2023 KELLER WILLIAMS WINTER PARK.

Home For Sale $579,900

Charming single-story home featuring a well-maintained lawn and a two-car garage at 7584 Lodge Pole Trl, Winter Park, FL 32792
View Details 40 Photos
Detailed floorplan layout of the house showing room dimensions and layout at 7584 Lodge Pole Trl, Winter Park, FL 32792
Covered front entry with decorative sidelights and a concrete path at 7584 Lodge Pole Trl, Winter Park, FL 32792
Inviting foyer with decorative glass sidelights and attractive wood-look flooring at 7584 Lodge Pole Trl, Winter Park, FL 32792
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1906

  • Year Built

    1972

  • $/SqFt

    $304

Arrowhead Cove - Ready for a new owner. Let's make a deal. SAND DOLLAR REALTY GROUP INC.

Home For Sale $500,000

Charming bungalow with a screened porch, lush landscaping, and a brick-paved street at 2011 Harmon Ave, Winter Park, FL 32789
View Details 3 Photos
Bungalow-style home featuring a screened porch, driveway, and established landscaping at 2011 Harmon Ave, Winter Park, FL 32789
Aerial view of the property showing the backyard, landscaping, and surrounding neighborhood at 2011 Harmon Ave, Winter Park, FL 32789
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1699

  • Year Built

    1925

  • $/SqFt

    $294

Lawndale - Property being sold for lot value. 100 x 140. Zoned R2. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,490,000

Charming two-story home with mature landscaping and manicured front lawn at 1299 Harding Street, Winter Park, FL 32789
View Details 52 Photos
Inviting home exterior with brick path and blooming flowering trees at 1299 Harding Street, Winter Park, FL 32789
Spacious living room with hardwood floors, fireplace, and built-in shelving at 1299 Harding Street, Winter Park, FL 32789
Open living space with hardwood floors, large sofa, and ample natural light at 1299 Harding Street, Winter Park, FL 32789
On Market For 4 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3784

  • Year Built

    1951

  • $/SqFt

    $658

Kronenberger - Located just steps from the 5-acre Kraft Azalea Garden with lakefront trails and a fishing dock, and a short stroll to Park Avenue to enjoy a scenic boat tour or one of the many museums—this is a truly exceptional offering in one of Winter Park’s most sought-after enclaves. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $675,000

Cozy single-story home with gravel yard and carport parking, surrounded by lush trees providing shade and privacy at 3019 Northwood Blvd, Winter Park, FL 32789
View Details 38 Photos
Covered carport area, offering protection from the elements and decorated with potted plants and grilling area at 3019 Northwood Blvd, Winter Park, FL 32789
Inviting entryway with classic furnishings and art, leading to the home's interior spaces at 3019 Northwood Blvd, Winter Park, FL 32789
Comfortable living area featuring retro furniture and decor, offering a cozy and inviting space at 3019 Northwood Blvd, Winter Park, FL 32789
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1662

  • Year Built

    1953

  • $/SqFt

    $406

Northwood Terrace - 2 Car Carport. Value is in the land. SAND DOLLAR REALTY GROUP INC.

Home For Sale $579,500

Charming single-story home with a brick facade, lush lawn, and a long driveway under a sunny, partly cloudy sky at 3131 Lowndes Dr, Winter Park, FL 32792
View Details 24 Photos
Charming single-story home with well-manicured lawn and inviting curb appeal at 3131 Lowndes Dr, Winter Park, FL 32792
Bright living room with ceiling fan, stylish decor, and lots of natural light at 3131 Lowndes Dr, Winter Park, FL 32792
Modern eat-in kitchen with white cabinets, stainless steel appliances, and updated countertops at 3131 Lowndes Dr, Winter Park, FL 32792
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2126

  • Year Built

    1967

  • $/SqFt

    $273

Georgetown Estates - Schedule your private tour today and step into the home that defines Winter Park living! A +ROI PROPERTY.

Home For Sale $569,000

Charming light blue single story home with a well manicured front yard and walkway to the front door at 1368 Devon Rd, Winter Park, FL 32789
View Details 28 Photos
Charming light blue single story home with a well manicured front yard and walkway to the front door at 1368 Devon Rd, Winter Park, FL 32789
Spacious living room with beautiful parquet flooring, large sofa, ceiling fans, and dining area visible at 1368 Devon Rd, Winter Park, FL 32789
Spacious living room and dining area with beautiful parquet flooring and modern ceiling fans at 1368 Devon Rd, Winter Park, FL 32789
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1642

  • Year Built

    1952

  • $/SqFt

    $347

Orwin Manor - Call for your private showing today! LPT REALTY, LLC.

Home For Sale $450,000

Charming home featuring a dark green exterior, metal roof, fenced yard and white window awnings at 710 W Swoope W Ave, Winter Park, FL 32789
View Details 12 Photos
Charming home featuring a dark green exterior, metal roof, fenced yard and white window awnings at 710 W Swoope W Ave, Winter Park, FL 32789
Spacious backyard with a small storage shed, perfect for outdoor activities and entertaining at 710 W Swoope W Ave, Winter Park, FL 32789
Spacious backyard featuring green grass and view of the back of house with screened in back porch at 710 W Swoope W Ave, Winter Park, FL 32789
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    960

  • Year Built

    1950

  • $/SqFt

    $469

Bungalow with metal roof approximately one block from Winter Park mall. Considered an excellent location. FIRMAN A. EMANUEL.

Home For Sale $4,100,000

Beautiful two-story home featuring a front-entry garage, balcony and manicured lawn at 1782 Pine Ave, Winter Park, FL 32789
View Details 13 Photos
Charming home with a well-manicured lawn and a classic facade, perfect for suburban living at 1782 Pine Ave, Winter Park, FL 32789
Backyard featuring a refreshing pool, lush lawn, perfect for relaxation and entertainment at 1782 Pine Ave, Winter Park, FL 32789
Detailed floor plan showcasing spacious layout with multiple bedrooms, living areas, and garages at 1782 Pine Ave, Winter Park, FL 32789
On Market For 5 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4782

  • Year Built

    2025

  • $/SqFt

    $857

Conwill Estates - Interlachen Golf community less than 5 min, Park Ave 10 min and restaurant and retail minutes away. Schedule your private tour today. EXP REALTY LLC.

Home For Sale $1,349,000

New construction home featuring a covered front porch, white siding, and modern windows at 1077 Minnesota Ave, Winter Park, FL 32789
View Details 12 Photos
Spacious home featuring a three-car garage and manicured landscaping at 1077 Minnesota Ave, Winter Park, FL 32789
Three-car garage featuring white doors at 1077 Minnesota Ave, Winter Park, FL 32789
Spacious home with a two-car garage and exterior paint touch ups in progress at 1077 Minnesota Ave, Winter Park, FL 32789
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3046

  • Year Built

    2025

  • $/SqFt

    $443

Don’t miss your opportunity to own a statement home that offers both sophistication and lifestyle. Private tours available by appointment. SHORES REAL ESTATE.

Home For Sale $479,900

Charming single-Gathering home featuring a two-car garage and mature landscaping at 1532 Lawndale Cir, Winter Park, FL 32792
View Details 36 Photos
A lovely two-story home with a well-maintained lawn and attached two-car garage at 1532 Lawndale Cir, Winter Park, FL 32792
Inviting front entrance with a white door, sidelight window, and decorative potted plant at 1532 Lawndale Cir, Winter Park, FL 32792
Open-concept living space with tile flooring, soaring ceilings, and natural light at 1532 Lawndale Cir, Winter Park, FL 32792
On Market For 4 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2035

  • Year Built

    1986

  • $/SqFt

    $236

Country Lane - Don’t miss your chance to own a piece of paradise—schedule your private tour today! KELLER WILLIAMS WINTER PARK.

Home For Sale $419,000

Charming single-story home featuring a blue garage door and well-maintained front lawn at 1566 Lawndale Cir, Winter Park, FL 32792
View Details 25 Photos
Spacious driveway leading to a blue garage door, set against a well-kept lawn at 1566 Lawndale Cir, Winter Park, FL 32792
Bright, open living area featuring vaulted ceilings and modern wood-look flooring at 1566 Lawndale Cir, Winter Park, FL 32792
Vaulted ceilings and fan highlight this open living space with modern vinyl plank flooring at 1566 Lawndale Cir, Winter Park, FL 32792
On Market For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1592

  • Year Built

    1985

  • $/SqFt

    $263

Experience the best of Winter Park living—text your real estate agent today for more information or to schedule a viewing! OPTIMA ONE REALTY, INC..

Home For Sale $2,199,000

Charming single-story home featuring dormer windows, stone walkway, manicured lawn, and professional landscaping at 1394 Stewart St, Winter Park, FL 32789
View Details 59 Photos
Charming one-story home with dormer windows, covered entryway, and manicured landscaping at 1394 Stewart St, Winter Park, FL 32789
Well-maintained single-story home with lush landscaping and mature trees on an expansive lawn at 1394 Stewart St, Winter Park, FL 32789
Spacious living room with brick fireplace, hardwood floors, and natural light at 1394 Stewart St, Winter Park, FL 32789
On Market For 6 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3907

  • Year Built

    1961

  • $/SqFt

    $563

Residents feel a deep sense of pride and belonging, while visitors are drawn to the charm and warmth that define our town. REALTY ONE GROUP INSPIRATION.

Pended $914,000

Beautiful single-story home featuring a three-car garage and a tile roof at 2012 Soaring Oak Way, Winter Park, FL 32792
View Details 55 Photos
Aerial view of a well-maintained home with a pristine yard, nearby pond, and three-car garage at 2012 Soaring Oak Way, Winter Park, FL 32792
Beautiful single-story home featuring a three-car garage and a tile roof at 2012 Soaring Oak Way, Winter Park, FL 32792
Charming entryway with stone accents and a cozy seating area at 2012 Soaring Oak Way, Winter Park, FL 32792
On Market For 4 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3050

  • Year Built

    2021

  • $/SqFt

    $300

Waters Edge At Hawks Crest - VIEW WALK THROUGH VIDEO - at Virtual tour link KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $799,999

Charming single-story home featuring a neatly maintained yard and a welcoming blue front door at 2838 Wright Ave, Winter Park, FL 32789
View Details 1 Photo
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1128

  • Year Built

    1952

  • $/SqFt

    $709

Lake Forest Park - Demo cost to be included in the purchase price. BALDWIN PARK REALTY LLC.

Home For Sale $1,360,000

Charming two-story home with a three-car garage, brick driveway, manicured lawn, and appealing curb appeal at 1269 Wading Waters Cir, Winter Park, FL 32792
View Details 68 Photos
Stunning two-story white home with a three-car garage, brick driveway, and manicured lawn with curb appeal at 1269 Wading Waters Cir, Winter Park, FL 32792
Beautiful aerial view of several homes with lush green trees and a scenic lake backdrop at 1269 Wading Waters Cir, Winter Park, FL 32792
Aerial shot of a private home with pool and patio, lush yard, and neighborhood street at 1269 Wading Waters Cir, Winter Park, FL 32792
On Market For 7 Days

  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    4468

  • Year Built

    2021

  • $/SqFt

    $304

Waters Edge At Hawks Crest - Put in your paddle board, kayak or just enjoy the wonderful sunsets from the fishing dock. HAMILTON REALTY.

Home For Sale $478,000

Charming single-story home with a stone facade, lush landscaping, and a bright turquoise front door at 7320 Fieldcrest Ave, Winter Park, FL 32792
View Details 54 Photos
Close-up of the front entrance with a gray walkway, colorful flowers, and a bright turquoise door at 7320 Fieldcrest Ave, Winter Park, FL 32792
Front exterior view of a white home with stone accents, manicured landscaping, and palm trees at 7320 Fieldcrest Ave, Winter Park, FL 32792
Close up of the front of the house, featuring a bright turquoise door and meticulously maintained landscaping at 7320 Fieldcrest Ave, Winter Park, FL 32792
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1919

  • Year Built

    1970

  • $/SqFt

    $249

Woodcrest - The property is situated in a cul-de-sac with no through traffic, no HOA with easy access to Full Sail, UCF, Winter Park shopping, restaurants, Downtown Orland, International Airport. COLDWELL BANKER REALTY.

Home For Sale $375,000

Two-story tan home with a single car garage and green lawn at 156 Oak Grove Rd, Winter Park, FL 32789
View Details 21 Photos
Two-story tan home with a single car garage and mature shade trees at 156 Oak Grove Rd, Winter Park, FL 32789
Aerial view of a home with fenced backyard and mature trees at 156 Oak Grove Rd, Winter Park, FL 32789
Open concept Living Room with ceiling fan and tile floors at 156 Oak Grove Rd, Winter Park, FL 32789
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1456

  • Year Built

    1995

  • $/SqFt

    $258

Don’t miss this exceptional opportunity—schedule your private showing today! EVERLANE REALTY LLC.

Pended $1,395,000

Charming single-story home featuring a beautifully landscaped front yard with lush green lawn, manicured hedges, and palm trees at 1633 Pine Ave, Winter Park, FL 32789
View Details 36 Photos
Inviting entryway showcasing a wood front door with decorative wreath, framed by trimmed hedges and a brick walkway at 1633 Pine Ave, Winter Park, FL 32789
Open-concept living area with hardwood floors, view of the kitchen, and neutral decor perfect for relaxing or entertaining at 1633 Pine Ave, Winter Park, FL 32789
Cozy bedroom with hardwood floors, natural light, and built-in bookcase with a quiet spot to read and unwind at 1633 Pine Ave, Winter Park, FL 32789
On Market For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2481

  • Year Built

    1951

  • $/SqFt

    $562

Lake Knowles Terrace - It's walking distance to Phelps Park and just a short drive to the charming shops and dining on Park Avenue. FANNIE HILLMAN & ASSOCIATES.

Pended $950,000

Charming brick home featuring a manicured lawn, walkway, and two white Adirondack chairs on a beautiful sunny day at 901 Golfside Dr, Winter Park, FL 32792
View Details 44 Photos
Beautiful home showcasing the manicured lawn, trimmed bushes, and two-car garage, all under a bright blue sky at 901 Golfside Dr, Winter Park, FL 32792
Corner lot featuring a charming brick house with a well-manicured lawn, pathway, and two-car garage at 901 Golfside Dr, Winter Park, FL 32792
Spacious living room featuring hardwood floors, a leather sofa, a dining area, and lots of natural light at 901 Golfside Dr, Winter Park, FL 32792
On Market For 6 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2392

  • Year Built

    1969

  • $/SqFt

    $397

Golfside - Don't miss out on this perfect home for creating memories for years to come! COLDWELL BANKER RESIDENTIAL RE.

Pended $799,000

Charming single-story home featuring a two-car garage, well-manicured lawn, and beautiful brick paver driveway at 2255 Marsh Sedge Ln, Winter Park, FL 32792
View Details 36 Photos
Inviting foyer featuring neutral paint, paneled walls, a console table with decorative accents, and a tiled floor at 2255 Marsh Sedge Ln, Winter Park, FL 32792
Cozy living room featuring large windows, a comfortable seating arrangement, and a stylish area rug at 2255 Marsh Sedge Ln, Winter Park, FL 32792
Elegant living room featuring recessed lighting, neutral paint, comfortable seating, and a stylish area rug at 2255 Marsh Sedge Ln, Winter Park, FL 32792
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2192

  • Year Built

    2020

  • $/SqFt

    $365

Preserve At Hawks Crest - Click the link for the virtual 3-D tour! KELLER WILLIAMS ADVANTAGE 2 REALTY.

Home For Sale $675,000

Charming single-story home featuring a well-manicured lawn and convenient carport at 843 W Swoope Ave, Winter Park, FL 32789
View Details 36 Photos
Inviting home exterior featuring a manicured lawn and a covered carport with a paved driveway at 843 W Swoope Ave, Winter Park, FL 32789
Inviting front entrance with manicured lawn and stone walkway leading to a stylish front door at 843 W Swoope Ave, Winter Park, FL 32789
Quaint home exterior with dark trim and convenient carport in a lush, green setting at 843 W Swoope Ave, Winter Park, FL 32789
On Market For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1232

  • Year Built

    1962

  • $/SqFt

    $548

Request your private showing today and make the move to Winter Park. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $575,000

Charming single-story home with a well-maintained yard, long driveway, and a carport at 2007 Strathaven Road, Winter Park, FL 32792
View Details 30 Photos
Inviting single-story home featuring lush landscaping, a curved driveway, and mature trees at 2007 Strathaven Road, Winter Park, FL 32792
Carport entrance showcasing updated exterior features including fresh paint, and new windows at 2007 Strathaven Road, Winter Park, FL 32792
Open-concept living room with modern flooring, connecting seamlessly to a bright, updated kitchen at 2007 Strathaven Road, Winter Park, FL 32792
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1699

  • Year Built

    1957

  • $/SqFt

    $338

You’ll be glad you did! EXP REALTY LLC.

Home For Sale $499,900

Charming single-story home with a well-manicured lawn and mature shade tree at 4887 Seminole Ave, Winter Park, FL 32792
View Details 52 Photos
Charming single-story home with a well-manicured lawn and attached two-car garage at 4887 Seminole Ave, Winter Park, FL 32792
Cozy home featuring a mature shade tree and a fenced yard at 4887 Seminole Ave, Winter Park, FL 32792
Well-maintained home featuring a classic white front door and a two-car garage at 4887 Seminole Ave, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2256

  • Year Built

    1954

  • $/SqFt

    $222

Minutes to the 417 Toll Road and Hwy 436 for quick access to Orlando International Airport, University of Central Florida and the surrounding areas. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $399,000

Charming single-story home with a carport and manicured lawn, complemented by a vibrant blue sky at 5144 Orange Ave, Winter Park, FL 32792
View Details 21 Photos
Modern kitchen features stainless steel appliances, granite countertops, and white cabinets, creating a sleek and functional space at 5144 Orange Ave, Winter Park, FL 32792
Dining room showcases a wooden table set for six, a stainless steel refrigerator, and natural light from a window at 5144 Orange Ave, Winter Park, FL 32792
Well-lit kitchen with stainless steel appliances, mosaic backsplash, and granite countertops, offering a stylish cooking area at 5144 Orange Ave, Winter Park, FL 32792
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1274

  • Year Built

    1976

  • $/SqFt

    $313

With modern upgrades, abundant outdoor space, and a fantastic location, this move-in-ready gem is ready for you to call it home! WEMERT GROUP REALTY LLC.

Home For Sale $395,000

Charming single-story home features a well-manicured lawn and inviting curb appeal at 2100 Shirewood Ct, Winter Park, FL 32792
View Details 21 Photos
Inviting single-story home with landscaped front yard and long, curving driveway at 2100 Shirewood Ct, Winter Park, FL 32792
Bright living room featuring a high ceiling, unique wall colors and a mix of flooring types at 2100 Shirewood Ct, Winter Park, FL 32792
Spacious living room with high ceiling, glass sliders and unique combination of flooring types at 2100 Shirewood Ct, Winter Park, FL 32792
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1427

  • Year Built

    1982

  • $/SqFt

    $277

Cedar Ridge - Do not miss the opportunity to make this lovely corner lot residence your own and enjoy the best of quiet neighborhood living. WEICHERT REALTORS HALLMARK PRO.

Home For Sale $595,000

Charming single-story home with light blue exterior, well-maintained lawn, and mature trees, perfect for curb appeal at 1230 N Denning Dr, Winter Park, FL 32789
View Details 39 Photos
Inviting living room with hardwood floors, plenty of natural light, and comfortable seating, ideal for relaxation at 1230 N Denning Dr, Winter Park, FL 32789
Spacious living room featuring hardwood floors, a stylish area rug, and plenty of room for entertaining guests at 1230 N Denning Dr, Winter Park, FL 32789
Bright and airy living room with an open layout, hardwood flooring, and comfortable furnishings creating a welcoming space at 1230 N Denning Dr, Winter Park, FL 32789
On Market For 9 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    972

  • Year Built

    1952

  • $/SqFt

    $612

Dixie Terrace - The homes proximity to The Winter Park Cultural Corridor which includes Rollins College, The Morse Museum, The Scenic Boat Tour, and The Farmer’s Market make this a most sought-after location. Schedule your private showing today! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $3,250,000

Charming home with manicured lawn, brick driveway, and lush landscaping creating curb appeal at 266 Chase Ave, Winter Park, FL 32789
View Details 40 Photos
Beautiful two-story home with a brick driveway, lush landscaping, and classic architectural details at 266 Chase Ave, Winter Park, FL 32789
Stunning two-story white home with manicured landscaping, mature trees, and brick driveway at 266 Chase Ave, Winter Park, FL 32789
Elegant front door with sidelights and a hanging lantern, framed by manicured hedges at 266 Chase Ave, Winter Park, FL 32789
On Market For 11 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4088

  • Year Built

    1930

  • $/SqFt

    $795

This is more than just a home, it’s a lifestyle and a rare chance to own one of Winter Park’s rare downtown area treasured properties. PREMIER SOTHEBY'S INTL. REALTY.

Pended $550,000

Charming one-story home with a brick pathway and mature trees at 2906 Rapidan Trl, Winter Park, FL 32789
View Details 30 Photos
Backyard pool surrounded by a brick border and a wooden fence at 2906 Rapidan Trl, Winter Park, FL 32789
Entryway with parquet floors, decorative shuttered window, and a long hallway leading to the living areas at 2906 Rapidan Trl, Winter Park, FL 32789
Bright living room featuring a fireplace, neutral walls, and ample space at 2906 Rapidan Trl, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2326

  • Year Built

    1965

  • $/SqFt

    $236

), Hvac 2010, Electrical - 2022 **we Are Accepting Any And All Offers Through 9am Monday April 7, 2025. *** KELLER WILLIAMS WINTER PARK.

Home For Sale $549,000

Charming home entrance surrounded by lush landscaping and decorative potted plants at 2464 Lotafun Ave, Winter Park, FL 32789
View Details 22 Photos
Exterior view of home with mature trees, landscaping, and a gray truck in the driveway at 2464 Lotafun Ave, Winter Park, FL 32789
Exterior view of home with mature trees, landscaping, and a gray truck in the driveway at 2464 Lotafun Ave, Winter Park, FL 32789
View of the driveway and carport, featuring a truck, trailer, and mature trees around the property at 2464 Lotafun Ave, Winter Park, FL 32789
On Market For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1804

  • Year Built

    1951

  • $/SqFt

    $304

No limit for your imagination on this property. INTERNATIONAL FLORIDA PROPERTIES INC.

Home For Sale $434,900

Charming home featuring stone accents, a well-manicured lawn, and a spacious two-car garage at 5441 Justine Way, Winter Park, FL 32792
View Details 28 Photos
Inviting backyard pool with lounge chairs, screened-in lanai, and lush landscaping at 5441 Justine Way, Winter Park, FL 32792
Charming home featuring stone accents, a well-manicured lawn, and mature landscaping at 5441 Justine Way, Winter Park, FL 32792
Inviting front porch with seating area and decorative planters at 5441 Justine Way, Winter Park, FL 32792
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1366

  • Year Built

    1978

  • $/SqFt

    $318

Howell Branch Woods - Updates include 2024 attic insulation; 2023 solar; 2022 pool pump; 2021 painted kitchen cabinets; 2017 pool resurface; 2016 washer, dryer, replace two front windows. REDFIN CORPORATION.

Home For Sale $423,900

Charming single Gathering home with well-maintained lawn and beautiful front yard landscaping at 5144 Goldenrod Place Rd, Winter Park, FL 32792
View Details 36 Photos
Charming single Gathering home with well-maintained lawn and beautiful front yard landscaping at sunset at 5144 Goldenrod Place Rd, Winter Park, FL 32792
Charming single Gathering home with well-maintained lawn, garage and beautiful front yard landscaping at 5144 Goldenrod Place Rd, Winter Park, FL 32792
Charming single Gathering home with well-maintained lawn and beautiful front yard landscaping at 5144 Goldenrod Place Rd, Winter Park, FL 32792
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1467

  • Year Built

    1972

  • $/SqFt

    $289

Fully fenced and Large Shed for all your extra Storage needs in addition to 2 car garage. Schedule your showing today ! C. APOLLO REALTY INC.

Home For Sale $415,000

Charming single-story home with a brick facade, gray wood paneling, and a well-manicured lawn at 3214 Lowndes Dr, Winter Park, FL 32792
View Details 29 Photos
A gray single-story home with well-maintained lawn, sidewalk, and mature shade trees at 3214 Lowndes Dr, Winter Park, FL 32792
View of the house from the street highlighting the long driveway and a well-kept front yard at 3214 Lowndes Dr, Winter Park, FL 32792
The front of this home has a covered porch with a chair, stone landscaping, and brick exterior at 3214 Lowndes Dr, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1200

  • Year Built

    1965

  • $/SqFt

    $346

Don’t miss your chance to make this spectacular property yours! MARK SPAIN REAL ESTATE.

Pended $3,850,000

Stunning two-story Mediterranean home featuring lush landscaping, a private driveway, and a two-car garage at 861 Bonita Dr, Winter Park, FL 32789
View Details 59 Photos
Elegant two-story home with a tile roof, arched entryway, balcony, lush landscaping, and a circular driveway at 861 Bonita Dr, Winter Park, FL 32789
Gorgeous two-story house showcasing manicured landscaping, a tile roof, arched entryway, and a brick-paved driveway at 861 Bonita Dr, Winter Park, FL 32789
Aerial view of a magnificent home surrounded by trees, showcasing the tile roof and circular driveway at 861 Bonita Dr, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 10 Days

  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    6939

  • Year Built

    1999

  • $/SqFt

    $555

Comstock Park - Situated in the heart of Winter Park, this exquisite property offers the perfect blend of sophistication, comfort, privacy, and location. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $655,000

Modern home featuring a wooden garage door, white exterior, and lush landscaping with a palm tree at 532 Darcey Dr, Winter Park, FL 32792
View Details 35 Photos
Inviting front porch with a white brick wall, black door, and decorative plants, offering a stylish entryway at 532 Darcey Dr, Winter Park, FL 32792
Charming home with a modern garage door, lush lawn, and flower boxes enhancing its curb appeal at 532 Darcey Dr, Winter Park, FL 32792
Cozy living room featuring a brick fireplace, plantation shutters, and stylish furnishings for comfortable living at 532 Darcey Dr, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1409

  • Year Built

    1958

  • $/SqFt

    $465

Truly a must see! Welcome Home! JWJ REALTY LLC.

Home For Sale $575,000

Charming single-story home with a two-car garage, well-maintained lawn, and beautiful landscaping at 1430 Hyde Park Dr, Winter Park, FL 32792
View Details 35 Photos
Expansive aerial view showcases a serene lake surrounded by lush greenery and beautiful houses at 1430 Hyde Park Dr, Winter Park, FL 32792
Inviting single-Gathering home with brick accents, a two-car garage, and freshly landscaped front yard at 1430 Hyde Park Dr, Winter Park, FL 32792
Attractive single-level home featuring a two-car garage, lovely landscaping, and a welcoming front yard at 1430 Hyde Park Dr, Winter Park, FL 32792
On Market For 11 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1947

  • Year Built

    1987

  • $/SqFt

    $295

Hyde Park - The Roof is only 4 years and the AC was replaced in 2013! KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $424,000

Charming single-story home with brick accents, neat landscaping, and a two-car garage at 3021 Little Cypress Cv, Winter Park, FL 32792
View Details 47 Photos
Single-story home with brick and siding exterior, complemented by a brick walkway and manicured shrubbery at 3021 Little Cypress Cv, Winter Park, FL 32792
Well-maintained single-story home with a brick facade, two-car garage, and neatly trimmed front yard at 3021 Little Cypress Cv, Winter Park, FL 32792
Functional kitchen featuring wood-look flooring, ample cabinet space, and white appliances at 3021 Little Cypress Cv, Winter Park, FL 32792
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1673

  • Year Built

    1987

  • $/SqFt

    $253

Gas used for stovetop, fireplace and water heater. LPT REALTY LLC.

Pended $400,000

Charming single-story home with a well-maintained lawn and mature landscaping at 2292 Hawick Ln, Winter Park, FL 32792
View Details 1 Photo
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1322

  • Year Built

    1958

  • $/SqFt

    $303

Buyer is responsible for doing any research and contacting the city of Winter Park on split's zoning, building codes, permits, etc. KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $1,690,000

Contemporary two-story home featuring a three-car garage, lush landscaping, and a classic chimney at 8041 Lake Waunatta Dr, Winter Park, FL 32792
View Details 85 Photos
Stunning aerial view of a home with private lake access, dock, and inviting backyard pool at 8041 Lake Waunatta Dr, Winter Park, FL 32792
The backyard features a modern pool and outdoor seating area with a view of the lake at 8041 Lake Waunatta Dr, Winter Park, FL 32792
Beautiful backyard with private lake access and dock at 8041 Lake Waunatta Dr, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5329

  • Year Built

    1984

  • $/SqFt

    $317

Schedule your private tour today! KELLER WILLIAMS REALTY AT THE PARKS.

Pended $535,000

Charming single-Gathering home with a well-maintained lawn, mature landscaping, and an attached two-car garage at 7619 Georgeann St, Winter Park, FL 32792
View Details 49 Photos
Charming single-Gathering home with a well-maintained lawn, mature landscaping, and an attached two-car garage at 7619 Georgeann St, Winter Park, FL 32792
Charming single-Gathering home with a well-maintained lawn, mature landscaping, and an attached two-car garage at 7619 Georgeann St, Winter Park, FL 32792
Charming single-Gathering home with a well-maintained lawn, mature landscaping, and an attached two-car garage at 7619 Georgeann St, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2053

  • Year Built

    2003

  • $/SqFt

    $261

CALL TODAY to schedule your private tour! APEXPRO PROPERTY SOLUTIONS LLC.

Pended $430,000

Reduced By $15,000

Charming single story home with a large driveway and attached garage at 3259 Ellwood Ct, Winter Park, FL 32792
View Details 34 Photos
Inviting front entrance with white columns and shutters on a well-maintained exterior at 3259 Ellwood Ct, Winter Park, FL 32792
Spacious two car garage with a beige garage door on a sunny day at 3259 Ellwood Ct, Winter Park, FL 32792
Bright living room featuring a brick wall accent, carpeted floors, and doorways leading to other rooms at 3259 Ellwood Ct, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 14 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1889

  • Year Built

    1969

  • $/SqFt

    $228

Call now for your private showing! LPT REALTY LLC.

Home For Sale $420,000

Single-Gathering home with a two-car garage, manicured lawn, and mature trees at 1041 Manchester Cir, Winter Park, FL 32792
View Details 28 Photos
Well-maintained single-Gathering home with a two-car garage, manicured lawn, and mature trees at 1041 Manchester Cir, Winter Park, FL 32792
Inviting backyard pool surrounded by a spacious patio, perfect for entertaining at 1041 Manchester Cir, Winter Park, FL 32792
Backyard featuring a refreshing pool, screened-in lanai, and well-maintained landscaping at 1041 Manchester Cir, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1678

  • Year Built

    1977

  • $/SqFt

    $250

Howell Estates - Don't miss out on this amazing opportunity in Winter Park! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $599,000

Charming single-story home featuring an attached two-car garage and mature landscaping at 701 Denton Rd, Winter Park, FL 32792
View Details 32 Photos
Charming single-story home featuring mature landscaping and inviting curb appeal at 701 Denton Rd, Winter Park, FL 32792
Charming single-story home featuring mature landscaping and inviting curb appeal at 701 Denton Rd, Winter Park, FL 32792
Charming single-story home featuring mature landscaping at 701 Denton Rd, Winter Park, FL 32792
On Market For 14 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2268

  • Year Built

    1961

  • $/SqFt

    $264

Don’t miss out on this incredible opportunity—schedule your showing today! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $415,000

Charming single-story home features a spacious driveway, covered carport, and mature trees at 1840 Maywood Rd, Winter Park, FL 32792
View Details 23 Photos
Cozy single-Gathering home with mature trees, white trim windows, and well-maintained landscaping at 1840 Maywood Rd, Winter Park, FL 32792
Charming single-story home features a spacious driveway, covered carport, and mature trees at 1840 Maywood Rd, Winter Park, FL 32792
A covered carport with a decorative block wall and well-maintained concrete flooring at 1840 Maywood Rd, Winter Park, FL 32792
On Market For 13 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1570

  • Year Built

    1957

  • $/SqFt

    $264

Tanglewood - This home is move-in ready so schedule your tour today! PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,290,000

Stunning two-story home with a brick driveway, landscaping, and well-maintained lawn at 1201 Wading Waters Cir, Winter Park, FL 32792
View Details 50 Photos
Beautiful two-story home with a well-manicured lawn and a two car garage at 1201 Wading Waters Cir, Winter Park, FL 32792
Inviting front entrance with a glass door, stone accents, and a cozy seating area at 1201 Wading Waters Cir, Winter Park, FL 32792
Charming front porch with brick pavers, stone columns, and cozy seating area at 1201 Wading Waters Cir, Winter Park, FL 32792
On Market For 16 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4266

  • Year Built

    2020

  • $/SqFt

    $302

Waters Edge At Hawks Crest - This home is the perfect blend of luxury, comfort, and convenience—don’t miss the opportunity to make it yours COLDWELL BANKER RESIDENTIAL RE.

Pended $3,995,000

Stunning home exterior featuring stone accents, large windows, lush landscaping, and a paver driveway at 2020 Venetian Way, Winter Park, FL 32789
View Details 52 Photos
Beautiful home exterior with mature palms, stone accents, lush landscaping, and a spacious paver driveway at 2020 Venetian Way, Winter Park, FL 32789
Idyllic waterfront backyard with a private dock, lush landscaping, and serene lake views at 2020 Venetian Way, Winter Park, FL 32789
Picturesque backyard with a private dock, beautiful sunset views over the water, and mature trees at 2020 Venetian Way, Winter Park, FL 32789
On Market For 16 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4188

  • Year Built

    1979

  • $/SqFt

    $954

Many amenities are minutes away and include a short distance to Winter Park Racquet Club, close to Park Avenue, major roadways and fantastic schools Dommerich Elementary, Maitland Middle and Winter Park High. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $2,690,000

Beautifully landscaped home exterior with mature trees, paver driveway and a two-car garage, perfect curb appeal at 7849 Georgeann St, Winter Park, FL 32792
View Details 65 Photos
Home with a well-maintained yard, stone accents, a side-entry two-car garage and a covered porch entrance at 7849 Georgeann St, Winter Park, FL 32792
Stunning home with lush landscaping, mature palms and a two-car garage, creating a picturesque view at 7849 Georgeann St, Winter Park, FL 32792
Covered front entrance features a stone pillar, manicured landscaping, and a stone pathway at 7849 Georgeann St, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 17 Days

  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    4860

  • Year Built

    2012

  • $/SqFt

    $553

Be sure to preview the video https://bit.ly/423Mrok and the 3D Matterport Showcase https://bit.ly/3XFly8W KELLER WILLIAMS REALTY AT THE PARKS.

Viewing HOMES 1 to 50 of 302

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.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$514,812
$439,950
138
2.2%
50.7%
83

Apopka
$526,218
$470,000
551
1.3%
47.4%
90

Belle Isle
$867,598
$639,746
24
0.0%
54.2%
70

Casselberry
$446,494
$429,450
102
2.0%
47.1%
64

Celebration
$1,346,895
$1,059,362
52
0.0%
44.2%
98

Champions Gate
$682,426
$687,495
22
0.0%
50.0%
265

Chuluota
$877,584
$689,000
25
0.0%
28.0%
39

Clermont
$578,711
$499,000
711
0.6%
49.5%
80

Gotha
$1,020,229
$649,990
15
0.0%
46.7%
60

Groveland
$481,758
$407,000
263
1.1%
52.1%
85

Harmony
$447,359
$419,900
69
0.0%
34.8%
91

Kissimmee
$518,501
$445,000
2401
1.5%
47.0%
101

Longwood
$746,941
$567,500
216
1.4%
46.3%
72

Maitland
$834,371
$624,495
80
2.5%
48.8%
75

Minneola
$559,225
$538,995
144
0.7%
38.2%
84

Montverde
$1,464,596
$1,090,370
58
0.0%
36.2%
116

Ocoee
$533,306
$489,900
189
1.6%
51.9%
76

Orlando
$682,982
$499,000
2948
1.6%
47.9%
79

Oviedo
$730,679
$649,000
194
1.0%
41.2%
72

Poinciana
$328,133
$314,445
272
0.4%
54.0%
120

Reunion
$1,804,721
$1,125,000
111
0.9%
49.5%
147

Saint Cloud
$561,505
$466,990
371
0.8%
72.0%
180

Sanford
$532,711
$415,990
372
0.8%
53.8%
99

Sorrento
$618,757
$479,990
107
0.9%
52.3%
84

Windermere
$2,145,184
$1,324,500
288
0.3%
45.5%
98

Winter Garden
$871,729
$710,000
605
0.5%
48.9%
84

Winter Springs
$644,991
$489,500
130
0.0%
44.6%
73

EasyStreet

Call to Schedule a Showing

(407) 278-2057

(407) 278-2057