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Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $1,400,000

Inviting home featuring manicured landscaping, a brick walkway and a grand arched front door at 1370 Alberta Dr, Winter Park, FL 32789
View Details 37 Photos
Close up of the home's beautiful arched doorway, trimmed with columns, and surrounding well maintained landscaping at 1370 Alberta Dr, Winter Park, FL 32789
Bright living room showcasing hardwood floors and an open doorway to the adjacent room at 1370 Alberta Dr, Winter Park, FL 32789
Cozy living room featuring hardwood floors, a fireplace, and ample natural light at 1370 Alberta Dr, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market Today

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3483

  • Year Built

    1957

  • $/SqFt

    $402

ft. with 2 bedrooms and 1 full bath and the guest 1 full bath in the guest house garage, totaling 3,483 sq. ft. All measurements are approximate. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $445,000

Charming single-story home with brown siding, white trim, an attached garage, and a well-maintained front lawn at 3259 Ellwood Ct, Winter Park, FL 32792
View Details 32 Photos
Bright living room featuring a brick wall accent, carpeted floors, and doorways leading to other rooms at 3259 Ellwood Ct, Winter Park, FL 32792
Carpeted bedroom with window, neutral walls, and natural light at 3259 Ellwood Ct, Winter Park, FL 32792
Bedroom features carpeted floors, a ceiling fan, and a closet for storage at 3259 Ellwood Ct, Winter Park, FL 32792
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1889

  • Year Built

    1969

  • $/SqFt

    $236

Call now for your private showing! LPT REALTY LLC.

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 Today

  • 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 2 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

Beautiful two-story home with a well-manicured lawn and a two car garage at 1201 Wading Waters Cir, Winter Park, FL 32792
View Details 50 Photos
Stunning two-story home with a brick driveway, landscaping, and well-maintained lawn 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 4 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.

Home For Sale $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 4 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 64 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
On Market For 5 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.

Pended $1,885,000

Stunning two-story home with a white brick facade, black trim, and lush landscaping at 2144 Sycamore Dr, Winter Park, FL 32789
View Details 6 Photos
Beautiful white modern home with a manicured lawn and a black two-car garage at 2144 Sycamore Dr, Winter Park, FL 32789
Modern kitchen with an island, white cabinetry, stainless steel appliances, and a wine cooler at 2144 Sycamore Dr, Winter Park, FL 32789
Open living and dining area with hardwood floors, a fireplace, and plenty of natural light at 2144 Sycamore Dr, Winter Park, FL 32789
On Market For 4 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3499

  • Year Built

    2024

  • $/SqFt

    $539

Northwood Terrace - Stunning new Winter Park residence. COMPASS FLORIDA LLC.

Home For Sale $1,650,000

Stunning two-story home with modern architecture, brick accents, manicured lawn, and a sleek metal roof at 2408 Lafayette Ave, Winter Park, FL 32789
View Details 31 Photos
Beautiful home showcasing modern design with grey brick, a driveway, and a well-kept lawn at 2408 Lafayette Ave, Winter Park, FL 32789
Open-concept living and dining area featuring hardwood floors, modern decor, and ample natural light at 2408 Lafayette Ave, Winter Park, FL 32789
Cozy sitting room with modern chairs, stylish decor, and a large window with natural light at 2408 Lafayette Ave, Winter Park, FL 32789
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2838

  • Year Built

    2024

  • $/SqFt

    $581

Winter Park Village - This home is a true gem that combines thoughtful details with sophisticated style. CORCORAN PREMIER REALTY.

Home For Sale $1,495,000

Charming two-story home with brick accents, a two-car garage, and lush landscaping at 1601 Chestnut Ave, Winter Park, FL 32789
View Details 34 Photos
Inviting home exterior with lush greenery, trimmed hedges, and a cozy seating area on the porch at 1601 Chestnut Ave, Winter Park, FL 32789
Welcoming front porch with chairs, lush greenery and a decorative door at 1601 Chestnut Ave, Winter Park, FL 32789
Bright foyer featuring wood floors, decorative table with mirror, and a glass panel door at 1601 Chestnut Ave, Winter Park, FL 32789
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2795

  • Year Built

    2017

  • $/SqFt

    $535

Lake Knowles Terrace - A location like no other, call today to schedule your private tour. KELLER WILLIAMS ELITE PARTNERS III REALTY.

Home For Sale $1,395,000

Charming two-story home with landscaped yard and mature trees along the lakefront at 7706 Waunatta Ct, Winter Park, FL 32792
View Details 52 Photos
Aerial view of a lakefront property featuring a covered boat dock and lush green trees at 7706 Waunatta Ct, Winter Park, FL 32792
Aerial view of the home showcasing its lakeside location and spacious lawn at 7706 Waunatta Ct, Winter Park, FL 32792
Well-maintained home with a spacious front yard and attached two-car garage at 7706 Waunatta Ct, Winter Park, FL 32792
On Market For 4 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3858

  • Year Built

    1978

  • $/SqFt

    $362

Complete with a spacious two-car garage, this home is the ideal blend of comfort, elegance and waterfront charm. PREMIER SOTHEBY'S INTL. REALTY.

Pended $799,990

Charming two-story home featuring a manicured lawn, two-car garage, and inviting curb appeal on a sunny day at 440 Shoreview Ave, Winter Park, FL 32789
View Details 41 Photos
An elevated view showcasing a well-maintained home with manicured landscaping and a beautiful roof at 440 Shoreview Ave, Winter Park, FL 32789
A stunning aerial view of a home near a picturesque lake and lush greenery, highlighting serene surroundings at 440 Shoreview Ave, Winter Park, FL 32789
Inviting entryway featuring dark hardwood floors, a striking front door, and elegant decor at 440 Shoreview Ave, Winter Park, FL 32789
On Market For 4 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2205

  • Year Built

    2014

  • $/SqFt

    $363

Killarney Estates - Call/Text for a private showing today. COMPASS FLORIDA LLC.

Pended $554,900

Charming single-story home featuring a landscaped yard and attached garage on a sunny day at 2025 Kimbrace Pl, Winter Park, FL 32792
View Details 22 Photos
Inviting living room featuring brick flooring, a ceiling fan, and natural lighting at 2025 Kimbrace Pl, Winter Park, FL 32792
Bright living room with brick floors, neutral furniture, and large windows at 2025 Kimbrace Pl, Winter Park, FL 32792
Cozy living room with exposed brick floors, ceiling fan and bright white walls at 2025 Kimbrace Pl, Winter Park, FL 32792
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1416

  • Year Built

    1957

  • $/SqFt

    $392

Kenilworth Shores - This is more than just a home – it's an invitation to create your ideal living space in one of Winter Park's most promising neighborhoods. CORCORAN PREMIER REALTY.

Pended $525,000

Charming single-story home featuring a well-manicured lawn, arched entryway, and two-car garage at 1946 King Arthurs Ct, Winter Park, FL 32792
View Details 44 Photos
Elegant entryway with an arched doorway, black door, and tropical plants enhancing curb appeal at 1946 King Arthurs Ct, Winter Park, FL 32792
Inviting front porch featuring an arched entry and stylish black door with a 'Welcome' mat at 1946 King Arthurs Ct, Winter Park, FL 32792
Detailed floor plan showcasing the layout with dimensions of all rooms and spaces of the home at 1946 King Arthurs Ct, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2254

  • Year Built

    1969

  • $/SqFt

    $233

Winter Woods - With a newer roof, HVAC, electrical panels, this move-in-ready home is an incredible opportunity for carefree living. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $450,000

Charming single Gathering home showcasing brick accents, a well manicured lawn and a two car garage at 7602 Glenmoor Ln, Winter Park, FL 32792
View Details 48 Photos
View of single Gathering home on a sunny day showcasing brick accents, manicured lawn and a two car garage at 7602 Glenmoor Ln, Winter Park, FL 32792
Charming single Gathering home showcasing brick accents, a well manicured lawn and a two car garage at 7602 Glenmoor Ln, Winter Park, FL 32792
View of single Gathering home showcasing brick accents, a manicured lawn, and a two-car garage at 7602 Glenmoor Ln, Winter Park, FL 32792
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1687

  • Year Built

    1984

  • $/SqFt

    $267

Glenmoor - Don’t miss this incredible opportunity—schedule your showing today! KELLER WILLIAMS REALTY AT THE PARKS.

Pended $399,000

Charming single Gathering home featuring a lush green lawn, stone accents and a two-car garage at 7145 Knottypine Ave, Winter Park, FL 32792
View Details 54 Photos
Inviting hallway showcasing stylish tile flooring and decor leading to the spacious living room at 7145 Knottypine Ave, Winter Park, FL 32792
Spacious living room featuring neutral paint, tile floors and lots of natural light at 7145 Knottypine Ave, Winter Park, FL 32792
Inviting hallway leading to kitchen and dining area; features stylish tile flooring and decor at 7145 Knottypine Ave, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1894

  • Year Built

    1981

  • $/SqFt

    $211

Highest and Best Offers Due Monday, March 31st by 5:00 pm. HAMPTON WINDSOR REALTY LLC.

Home For Sale $2,200,000

Beautiful home with lush landscaping, brick driveway, and gated entrance for added security and privacy at 4469 Old Bear Run, Winter Park, FL 32792
View Details 71 Photos
An aerial view showcasing the home's waterfront location and surrounding neighborhood, complete with a private pool at 4469 Old Bear Run, Winter Park, FL 32792
Overhead view of the home's architectural layout with a pool and outdoor living space, mature trees for privacy at 4469 Old Bear Run, Winter Park, FL 32792
Panoramic view highlighting this home's scenic surroundings, expansive lawn, pool area, and convenient waterfront access at 4469 Old Bear Run, Winter Park, FL 32792
On Market For 5 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4288

  • Year Built

    1978

  • $/SqFt

    $513

Don't miss your chance to own a one-of-a-kind lakefront home, call today! HOME WISE REALTY GROUP, INC..

Home For Sale $2,150,000

Charming home with a circular driveway and lush landscaping provides an inviting curb appeal at 1560 Woodland Ave, Winter Park, FL 32789
View Details 48 Photos
Inviting home with a metal roof, manicured landscaping, and front porch at 1560 Woodland Ave, Winter Park, FL 32789
Charming home featuring a circular driveway, mature trees, and a well-manicured lawn at 1560 Woodland Ave, Winter Park, FL 32789
Beautifully landscaped home with a circular driveway, stone accents, and a welcoming front porch at 1560 Woodland Ave, Winter Park, FL 32789
On Market For 6 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3851

  • Year Built

    1990

  • $/SqFt

    $558

Comstock Park - A must see for those seeking the tranquil and exquisite Winter Park standard of living. LOKATION.

Home For Sale $1,050,000

Charming two-story home boasts a modern design with a well-manicured lawn and a brick-paved driveway leading to a two-car garage at 2680 Oglesby Ave, Winter Park, FL 32789
View Details 44 Photos
The bright, sunny home has a two-car garage and a brick-paved driveway, and is surrounded by manicured landscaping at 2680 Oglesby Ave, Winter Park, FL 32789
The front entrance features a modern blue door with glass panes, complemented by well-maintained landscaping at 2680 Oglesby Ave, Winter Park, FL 32789
Bright, open foyer with hardwood floors leads to the living area, showcasing the home's modern design at 2680 Oglesby Ave, Winter Park, FL 32789
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2546

  • Year Built

    2019

  • $/SqFt

    $412

Dubsdread Heights - There is no HOA in this community. This home is available immediately. COMPASS FLORIDA LLC.

Home For Sale $749,900

Charming single-story home with a well-manicured lawn and mature trees offering shade and curb appeal at 2925 Banchory Rd, Winter Park, FL 32792
View Details 67 Photos
Inviting front entrance with arched entryway, updated landscaping, and a charming gate enhancing curb appeal at 2925 Banchory Rd, Winter Park, FL 32792
Close-up of the front porch showcasing the arched entryway, stylish light fixture, and well-maintained door at 2925 Banchory Rd, Winter Park, FL 32792
Bright living room featuring new flooring, large windows offering ample natural light, and a stylish front door at 2925 Banchory Rd, Winter Park, FL 32792
On Market For 6 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2419

  • Year Built

    1970

  • $/SqFt

    $310

Winter Park Pines - Don’t miss this opportunity—schedule your private showing today! BALDWIN PARK REALTY LLC.

Home For Sale $625,000

Charming single-story home with an orange front door and beautiful landscaping at 2712 Cady Way, Winter Park, FL 32792
View Details 39 Photos
Comfortable living room featuring a leather sofa, colorful rug, and bright decor at 2712 Cady Way, Winter Park, FL 32792
Open concept living room with hardwood floors, ceiling fans, and a view of the kitchen at 2712 Cady Way, Winter Park, FL 32792
Spacious living room with french doors, hardwood floors, and comfortable seating at 2712 Cady Way, Winter Park, FL 32792
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2197

  • Year Built

    1964

  • $/SqFt

    $284

Roof - 2016 Hvac - 2015 Electrical - 2010 KELLER WILLIAMS WINTER PARK.

Home For Sale $600,000

Charming single-story home with brick facade, manicured landscaping, and a driveway leading to an attached garage at 2310 Cady Way, Winter Park, FL 32792
View Details 37 Photos
Inviting living room with neutral tones, tile flooring, ceiling fan, and sliding doors to outdoor space at 2310 Cady Way, Winter Park, FL 32792
Bright living room featuring tile floors, comfortable seating, and a sliding glass door leading to the backyard at 2310 Cady Way, Winter Park, FL 32792
Spacious living and dining area with tile floors, plush seating, and a chandelier over the dining table at 2310 Cady Way, Winter Park, FL 32792
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1856

  • Year Built

    1961

  • $/SqFt

    $323

ROOF - 2012 HVAC - 2015 PLUMBING - 2013(re-piped) ELECTRICAL - 2012(new panel) KELLER WILLIAMS WINTER PARK.

Home For Sale $2,395,000

Beautiful exterior elevation showcasing stone accents, a two-car garage, and lush landscaping at 2814 Parkland Dr, Winter Park, FL 32789
View Details 63 Photos
A luxurious backyard with a pool, spa, outdoor kitchen, fireplace, and covered patio at 2814 Parkland Dr, Winter Park, FL 32789
Gorgeous exterior showing a two-car garage, stone details, a lush lawn, and dark facade at 2814 Parkland Dr, Winter Park, FL 32789
A well-lit backyard featuring a pool, spa, outdoor patio, fireplace, and exterior kitchen at 2814 Parkland Dr, Winter Park, FL 32789
On Market For 7 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3089

  • Year Built

    2025

  • $/SqFt

    $775

Lake Forest Park - You will not find a better opportunity to secure a recently completed, highly detailed, unique luxury home in the WP area that offers the feel, presentation, and function of 2814 Parkland Drive. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $760,000

Charming single-story home features a manicured lawn and a classic, inviting facade at 2178 Whitehall Dr, Winter Park, FL 32792
View Details 24 Photos
A single-story home with an attached garage, well-maintained lawn, and lovely landscaping at 2178 Whitehall Dr, Winter Park, FL 32792
Bright, spacious living room with terrazzo flooring and large windows offering serene outdoor views at 2178 Whitehall Dr, Winter Park, FL 32792
Elegant dining room featuring a glass-top table and modern chandelier with a view to the living room at 2178 Whitehall Dr, Winter Park, FL 32792
On Market For 7 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2360

  • Year Built

    1964

  • $/SqFt

    $322

Brookshire Heights - Schedule a showing today to experience the best of Winter Park living. BALDWIN PARK REALTY LLC.

Pended $729,900

Charming single-story home featuring a two-car garage, manicured lawn, and inviting curb appeal at 920 Fairway Dr, Winter Park, FL 32792
View Details 40 Photos
Inviting single-story home with a well-maintained lawn, mature shade tree, and welcoming facade at 920 Fairway Dr, Winter Park, FL 32792
Close-up of the entrance featuring a stylish front door, brick accents, and elegant outdoor lighting at 920 Fairway Dr, Winter Park, FL 32792
Open-concept living space with wood floors, a modern accent wall, and bright natural light at 920 Fairway Dr, Winter Park, FL 32792
On Market For 7 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2155

  • Year Built

    1973

  • $/SqFt

    $339

Golfside - This home is truly move-in ready, schedule your private showing today! WELCOME HOME FANNIE HILLMAN & ASSOCIATES.

Home For Sale $569,000

Charming single-story home boasts a spacious driveway, attached garage, and vibrant landscaping at 426 S Lakemont Ave, Winter Park, FL 32792
View Details 23 Photos
Relaxing backyard pool with mature trees and privacy fence is perfect for outdoor enjoyment at 426 S Lakemont Ave, Winter Park, FL 32792
Open kitchen with stainless appliances, breakfast bar, and cozy living area with fireplace at 426 S Lakemont Ave, Winter Park, FL 32792
Dining area features a wooden table set with kitchen view and ample natural light at 426 S Lakemont Ave, Winter Park, FL 32792
On Market For 7 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1656

  • Year Built

    1955

  • $/SqFt

    $344

Move in Ready Hurry! Won't Last! KELLER WILLIAMS HERITAGE REALTY.

Home For Sale $550,000

Charming one-story blue home with a lush green lawn, garage, and vibrant landscaping at 2565 Brookshire Ave, Winter Park, FL 32792
View Details 7 Photos
Inviting front entrance with brick walkway, chairs, and lush landscaping adding to its curb appeal at 2565 Brookshire Ave, Winter Park, FL 32792
Aerial view of property highlighting the lot lines, landscaping, and surrounding neighborhood at 2565 Brookshire Ave, Winter Park, FL 32792
Aerial view of the property showcases the layout, lush landscaping, and neighborhood context at 2565 Brookshire Ave, Winter Park, FL 32792
On Market For 7 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1000

  • Year Built

    1959

  • $/SqFt

    $550

Just a short walk to top-rated Winter Park schools and with easy access to the Cady Way Trail, this home is a must-see! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $515,000

Charming single-story home featuring a well-manicured lawn and mature trees at 2819 Scarlet Rd, Winter Park, FL 32792
View Details 37 Photos
Open kitchen featuring wood cabinets, granite countertops, and stainless steel appliances at 2819 Scarlet Rd, Winter Park, FL 32792
Spacious kitchen featuring tiled floors, wood cabinets, and granite countertops at 2819 Scarlet Rd, Winter Park, FL 32792
Bright kitchen featuring wood cabinets, a breakfast nook, and modern appliances at 2819 Scarlet Rd, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2197

  • Year Built

    1963

  • $/SqFt

    $234

Hvac - 2013, New Roof - 2024, Plumbing - 1997, New Electrical Panel -2025, New Hot Water Heater - 2025 KELLER WILLIAMS WINTER PARK.

Home For Sale $450,000

Charming single-story home features a modern garage door and well-maintained landscaping at 3073 Bluebrook Dr, Winter Park, FL 32792
View Details 41 Photos
Gorgeous kitchen with a large island featuring bar seating and modern stainless steel appliances at 3073 Bluebrook Dr, Winter Park, FL 32792
Bright kitchen features a large island with bar seating, modern lighting, and stainless steel appliances at 3073 Bluebrook Dr, Winter Park, FL 32792
Open kitchen boasts a large island with bar seating, stone countertops, and modern appliances at 3073 Bluebrook Dr, Winter Park, FL 32792
On Market For 6 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    1486

  • Year Built

    1973

  • $/SqFt

    $303

Laurel Springs - Schedule your showing today and seize the opportunity to own this remarkable property in one of Winter Park’s most desirable neighborhoods! FOWLKES REALTY CO.

Home For Sale $325,000

Charming home with an inviting red door, light green paint, and well-maintained front yard at 712 Baffie Ave, Winter Park, FL 32789
View Details 41 Photos
Landscaped front yard and charming single-story home with a red brick chimney and ample sunlight at 712 Baffie Ave, Winter Park, FL 32789
Well-kept home with mature trees, a manicured lawn, and great curb appeal at 712 Baffie Ave, Winter Park, FL 32789
Inviting sunroom with tile floors, wood ceiling, and bright lighting, perfect for relaxing at 712 Baffie Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 7 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1304

  • Year Built

    1925

  • $/SqFt

    $249

Dubsdread Heights - A great opportunity for first-time buyers, builders, or investors looking to buy smart and improve the asset. BALDWIN PARK REALTY LLC.

Home For Sale $2,400,000

Expansive lake view featuring a dock with a covered sitting area and lush green landscaping at 673 Balmoral Rd, Winter Park, FL 32789
View Details 76 Photos
Charming single-story home featuring a well-manicured lawn, mature landscaping and a covered front porch at 673 Balmoral Rd, Winter Park, FL 32789
Charming single-story home featuring a well-manicured lawn, mature landscaping and a covered front porch at 673 Balmoral Rd, Winter Park, FL 32789
Charming single-story home featuring a well-manicured lawn, mature landscaping and a covered front porch at 673 Balmoral Rd, Winter Park, FL 32789
On Market For 7 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2663

  • Year Built

    1964

  • $/SqFt

    $901

Kenilworth Shores - Don’t miss the opportunity to tour this home – schedule your showing today. KELLY PRICE & COMPANY LLC.

Home For Sale $504,000

Reduced By $11,000

Charming one-story home with a well-manicured lawn, a driveway, and an attached garage at 1564 Cavendish Rd, Winter Park, FL 32789
View Details 35 Photos
Inviting one-story home boasts lush landscaping and an attached garage at 1564 Cavendish Rd, Winter Park, FL 32789
A charming one-story home features a lush lawn and an attached garage at 1564 Cavendish Rd, Winter Park, FL 32789
Cozy front porch with white columns and a seating area at 1564 Cavendish Rd, Winter Park, FL 32789
On Market For 8 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1140

  • Year Built

    1953

  • $/SqFt

    $442

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

Home For Sale $1,875,000

Striking modern home with well-maintained lawn, lush landscaping, and a stylish gray facade at 1970 Laurel Rd, Winter Park, FL 32789
View Details 40 Photos
Contemporary home with a manicured lawn, trimmed hedges, and tall palm trees enhancing curb appeal at 1970 Laurel Rd, Winter Park, FL 32789
Sophisticated modern architecture featuring a well-kept lawn, manicured greenery, and stately palm trees at 1970 Laurel Rd, Winter Park, FL 32789
Close-up of the home's entrance, showcasing the walkway and professionally maintained landscaping at 1970 Laurel Rd, Winter Park, FL 32789
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3440

  • Year Built

    2015

  • $/SqFt

    $545

Charmont - Don’t miss this opportunity and schedule your private showing today! PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $515,000

Charming single-story home featuring a well-maintained lawn and a one-car garage at 1807 Yorkshire Dr, Winter Park, FL 32792
View Details 46 Photos
Close up of the home's front exterior with a garage and walkway to the front door at 1807 Yorkshire Dr, Winter Park, FL 32792
A cozy front porch with stone steps leads to the entryway at 1807 Yorkshire Dr, Winter Park, FL 32792
A covered front porch with ornate metal supports and a pathway to the side door at 1807 Yorkshire Dr, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1672

  • Year Built

    1956

  • $/SqFt

    $308

This is a rare opportunity to get into Central Florida's most prized community and make a home YOUR OWN! MAINFRAME REAL ESTATE.

Pended $359,900

Reduced By $20,000

Charming single-story home featuring a welcoming front porch, red door, and brick-lined pathway and garage at 1938 Eastbrook Blvd, Winter Park, FL 32792
View Details 31 Photos
Aerial view of a charming single-story home with a well-maintained lawn, red door and brick accents at 1938 Eastbrook Blvd, Winter Park, FL 32792
Charming single-story home with a well-manicured lawn, decorative shutters, and a welcoming front porch at 1938 Eastbrook Blvd, Winter Park, FL 32792
A single-story house with a two-car garage and brick-lined driveway, leading to the front door at 1938 Eastbrook Blvd, Winter Park, FL 32792
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1253

  • Year Built

    1965

  • $/SqFt

    $287

Located in a prime Winter Park location near top-rated schools, shopping, and dining, this move-in-ready home is a must-see! INVESTOR'S REAL ESTATE LLC.

Home For Sale $3,950,000

Charming home showcasing lush landscaping, a brick driveway, and a classic stucco exterior with a red tile roof at 851 Georgia Ave, Winter Park, FL 32789
View Details 46 Photos
Expansive aerial view of the house surrounded by lush greenery, mature trees, and featuring a pool and brick driveway at 851 Georgia Ave, Winter Park, FL 32789
Inviting entryway features a detailed wooden door, brick pathway, and decorative plants, creating a warm welcome at 851 Georgia Ave, Winter Park, FL 32789
Elegant foyer showcasing wood floors, arched doorways, a staircase, and a stylish console table with vibrant artwork at 851 Georgia Ave, Winter Park, FL 32789
On Market For 13 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4314

  • Year Built

    1935

  • $/SqFt

    $916

This home offers the best of both worlds: a rare opportunity to own a piece of Winter Park history, yet lovingly maintained with modern updates and conveniences throughout. FANNIE HILLMAN & ASSOCIATES.

Pended $735,000

Beautiful two-story home with a well-manicured lawn, mature trees, and a spacious driveway at 7945 Pleasant Pine Cir, Winter Park, FL 32792
View Details 43 Photos
Charming two-story home with a well-maintained lawn, mature trees, and a wide driveway at 7945 Pleasant Pine Cir, Winter Park, FL 32792
Inviting front porch with a decorative door, hanging light fixture, and a cozy seating area at 7945 Pleasant Pine Cir, Winter Park, FL 32792
Covered front porch with seating, a view of landscaped yard, and a charming neighborhood setting at 7945 Pleasant Pine Cir, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 12 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3496

  • Year Built

    2015

  • $/SqFt

    $210

Enclave At Aloma - Don't miss your opportunity to own this great home. Schedule your private showing today! COLDWELL BANKER RESIDENTIAL RE.

Pended $660,000

Charming single-story home with a spacious driveway, green lawn, and a lovely pink front door at 2732 Lion Heart Rd, Winter Park, FL 32792
View Details 21 Photos
Close-up of the home's pink double front doors, brick entryway, and a lush green plant at 2732 Lion Heart Rd, Winter Park, FL 32792
Bright living room with a brown sectional couch, stylish decor, and an open layout at 2732 Lion Heart Rd, Winter Park, FL 32792
Spacious open-concept living area with a brown sectional couch, wooden accents, and views into other rooms at 2732 Lion Heart Rd, Winter Park, FL 32792
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1975

  • Year Built

    1962

  • $/SqFt

    $334

This is not just a home it’s a lifestyle. FANNIE HILLMAN & ASSOCIATES.

Pended $565,000

Charming single-story home featuring a well-manicured lawn, a red front door, and mature trees providing shade at 2012 Loch Berry Rd, Winter Park, FL 32792
View Details 24 Photos
A close-up view of the front of the house, featuring a red front door and two chairs on the porch at 2012 Loch Berry Rd, Winter Park, FL 32792
Aerial view of a lovely home with mature trees, lush greenery, blue skies, and a well-maintained lawn at 2012 Loch Berry Rd, Winter Park, FL 32792
Bright, minimalist dining room showcasing tile flooring and a view into the kitchen at 2012 Loch Berry Rd, Winter Park, FL 32792
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1522

  • Year Built

    1956

  • $/SqFt

    $371

Kenilworth Shores - By marketing the property's potential for a tear-down and rebuild, this scenario attracts buyers interested in long-term investments that promise to uplift the neighborhood. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $565,000

Charming single-story home with a well-manicured lawn and beautiful blue shutters at 2381 Roxbury Rd, Winter Park, FL 32789
View Details 22 Photos
Bright living room featuring hardwood floors, cozy furniture, and ample natural light at 2381 Roxbury Rd, Winter Park, FL 32789
Inviting living area with fireplace, hardwood floors, and a ceiling fan at 2381 Roxbury Rd, Winter Park, FL 32789
Spacious open-concept living area featuring a fireplace, hardwood floors, and lots of windows at 2381 Roxbury Rd, Winter Park, FL 32789
On Market For 7 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1645

  • Year Built

    1949

  • $/SqFt

    $343

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

Home For Sale $439,000

Charming home featuring a well-maintained lawn, mature landscaping and updated gray exterior paint at 3420 Arnel Dr, Winter Park, FL 32792
View Details 37 Photos
Charming home featuring a well-maintained lawn, mature landscaping and updated gray exterior paint at 3420 Arnel Dr, Winter Park, FL 32792
Well-kept home with a long driveway, healthy green lawn and mature landscaping at 3420 Arnel Dr, Winter Park, FL 32792
Residential neighborhood featuring mature trees and well-manicured lawns at 3420 Arnel Dr, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1998

  • Year Built

    1967

  • $/SqFt

    $220

Don’t miss this incredible opportunity—schedule your private showing today! NEXTHOME NEIGHBORHOOD REALTY.

Home For Sale $429,900

Reduced By $20,000

Charming single-story home with a well-manicured lawn, palm trees, and attached two car garage at 4421 Steed Ter, Winter Park, FL 32792
View Details 47 Photos
Well-maintained single-story home featuring a two car garage, manicured lawn, and covered entryway at 4421 Steed Ter, Winter Park, FL 32792
Relaxing screened-in pool area with a spacious deck, perfect for outdoor enjoyment and entertaining at 4421 Steed Ter, Winter Park, FL 32792
Inviting screened-in pool area with a generous patio, ideal for relaxation and recreation at 4421 Steed Ter, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1788

  • Year Built

    1989

  • $/SqFt

    $240

Kings Cove - The location offers easy access to major highways for a quick commute to downtown Orlando and beyond. THIS IS AN AMAZING DEAL! BUSTAMANTE REAL ESTATE INC.

Home For Sale $425,000

Charming single-story home with a well-manicured lawn, lush landscaping, and an attached two-car garage at 5600 Revelwood Loop, Winter Park, FL 32792
View Details 28 Photos
Inviting single-story home with a two-car garage and a well-maintained lawn in a suburban neighborhood at 5600 Revelwood Loop, Winter Park, FL 32792
Charming single-story home with a well-manicured lawn, lush landscaping, and an attached two-car garage at 5600 Revelwood Loop, Winter Park, FL 32792
Inviting single-story home with a two-car garage, mature landscaping, and a well-maintained lawn at 5600 Revelwood Loop, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1598

  • Year Built

    1990

  • $/SqFt

    $266

Easy access to 417 and conveniently located to public am d private schools, shopping, restaurants and entertainment! Don't miss this BEAUTY! REAL ESTATE PROS.

Home For Sale $415,000

Gorgeous aerial view of home's location on the golf course near a pond and lake at 2259 Minnesota Ave, Winter Park, FL 32789
View Details 7 Photos
Aerial view showcases this home's proximity to a golf course, pond, and city skyline at 2259 Minnesota Ave, Winter Park, FL 32789
Charming blue home with well-maintained lawn, fenced backyard and access to paved street at 2259 Minnesota Ave, Winter Park, FL 32789
Inviting home showcasing lush front lawn, mature trees, and paved street access at 2259 Minnesota Ave, Winter Park, FL 32789
On Market For 13 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1015

  • Year Built

    1948

  • $/SqFt

    $409

20k impact fee credit/verify exact when pulling new permit LPT REALTY, LLC.

Home For Sale $549,900

Charming single-story home with a well-manicured lawn and inviting curb appeal and attached two-car garage at 2607 Verde Ln, Winter Park, FL 32792
View Details 46 Photos
Inviting single-story home featuring a pristine driveway, lush lawn, and a convenient two-car garage at 2607 Verde Ln, Winter Park, FL 32792
Attractive single-story home boasts a well-kept lawn, a spacious driveway, and attached two-car garage at 2607 Verde Ln, Winter Park, FL 32792
Welcoming front entrance featuring arched openings, providing a unique architectural charm and curb appeal at 2607 Verde Ln, Winter Park, FL 32792
On Market For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1953

  • Year Built

    1968

  • $/SqFt

    $282

One or more photo(s) have been virtually staged FOUNDERS REALTY GROUP.

Pended $2,695,000

Stunning exterior view of home featuring a three-car garage and meticulously landscaped front yard with paver driveway at 254 Sylvan Blvd, Winter Park, FL 32789
View Details 66 Photos
An elevated aerial view of the luxury home featuring a beautifully landscaped yard, mature trees, and a brick driveway at 254 Sylvan Blvd, Winter Park, FL 32789
Panoramic aerial view of the property showcasing its expansive layout, lush landscaping, and proximity to a lake at 254 Sylvan Blvd, Winter Park, FL 32789
Beautiful facade with palm trees, well-manicured landscaping, and paver driveway leading to the garage and front entrance at 254 Sylvan Blvd, Winter Park, FL 32789
On Market For 14 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3653

  • Year Built

    2000

  • $/SqFt

    $738

Sylvan Lake Shores - Don’t miss the opportunity to make this lake front home yours. Schedule your private showing today! KELLER WILLIAMS WINTER PARK.

Home For Sale $2,250,000

Gated driveway leads to an elegant home surrounded by mature landscaping at 7841 Georgeann St, Winter Park, FL 32792
View Details 64 Photos
Paved driveway leads to a spacious home surrounded by mature landscaping at 7841 Georgeann St, Winter Park, FL 32792
Beautiful home with a spacious, well-maintained front yard and circular driveway at 7841 Georgeann St, Winter Park, FL 32792
Beautiful home featuring lush tropical landscaping and a stone driveway at 7841 Georgeann St, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4560

  • Year Built

    1977

  • $/SqFt

    $493

Ideally situated minutes from the 417 and 408, this home provides easy access to downtown Orlando, the airport, and Central Florida’s renowned attractions, making it both a private sanctuary and a gateway to everything Central Florida offers. SPECTRUM GLOBAL REALTY, INC.

Home For Sale $1,650,000

Charming home featuring manicured landscaping, and a striking, modern front door entrance at 1701 Palmer Ave, Winter Park, FL 32789
View Details 58 Photos
A picturesque home with lush landscaping and mature trees adding natural beauty at 1701 Palmer Ave, Winter Park, FL 32789
Private courtyard area featuring tiled flooring and a charming decorative water feature at 1701 Palmer Ave, Winter Park, FL 32789
Outdoor kitchen area boasting a stainless steel grill and counter space at 1701 Palmer Ave, Winter Park, FL 32789
On Market For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2841

  • Year Built

    1953

  • $/SqFt

    $581

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

Home For Sale $459,999

Charming single-story home boasts a well-manicured lawn, gray exterior, and lovely curb appeal at 3132 Nicholson Dr, Winter Park, FL 32792
View Details 21 Photos
Charming single-story home boasts a well-manicured lawn, gray exterior, and lovely curb appeal at 3132 Nicholson Dr, Winter Park, FL 32792
Inviting foyer features luxury vinyl plank flooring, a grandfather clock, and a dining table at 3132 Nicholson Dr, Winter Park, FL 32792
Cozy living room featuring a stone fireplace, vaulted ceilings, and access to the lanai at 3132 Nicholson Dr, Winter Park, FL 32792
On Market For 14 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1537

  • Year Built

    1977

  • $/SqFt

    $299

Howell Branch Woods - Don’t miss your chance to own a slice of paradise—schedule your showing today! LIVE FLORIDA NOW LLC.

Home For Sale $490,700

Reduced By $5,000

Beautiful single-Gathering home featuring stone accents, a large driveway, and a well-maintained lawn at 1776 E Cheryl Dr, Winter Park, FL 32792
View Details 14 Photos
Bright living room showcasing wood floors, a stone fireplace, and contemporary lighting at 1776 E Cheryl Dr, Winter Park, FL 32792
Modern kitchen boasts white cabinets, stainless steel appliances, and an eye-catching backsplash at 1776 E Cheryl Dr, Winter Park, FL 32792
Relaxing screened-in patio area with a private pool, perfect for outdoor entertaining at 1776 E Cheryl Dr, Winter Park, FL 32792
On Market For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2014

  • Year Built

    1982

  • $/SqFt

    $244

Don't miss out on the chance to make this lovely property your own!. MINK REALTY.

Viewing HOMES 1 to 50 of 280

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 407-967-1435 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$524,688
$449,000
125
1.6%
52.0%
87

Apopka
$525,446
$460,000
531
1.3%
50.8%
91

Belle Isle
$842,498
$639,996
24
0.0%
45.8%
67

Casselberry
$456,181
$429,900
89
2.2%
51.7%
70

Celebration
$1,378,107
$1,079,000
51
0.0%
45.1%
111

Champions Gate
$684,394
$699,990
21
0.0%
52.4%
259

Chuluota
$878,100
$691,450
24
0.0%
41.7%
39

Clermont
$581,415
$499,000
693
0.9%
50.6%
85

Gotha
$1,019,649
$649,990
13
0.0%
38.5%
59

Groveland
$483,841
$410,007
248
0.8%
52.0%
84

Harmony
$445,117
$423,400
71
0.0%
28.2%
82

Kissimmee
$517,642
$440,000
2305
1.6%
48.0%
102

Longwood
$789,349
$575,000
193
1.6%
49.7%
76

Maitland
$840,384
$624,000
75
2.7%
50.7%
92

Minneola
$562,710
$535,000
127
0.8%
40.2%
96

Montverde
$1,499,752
$1,106,322
56
0.0%
39.3%
129

Ocoee
$528,705
$465,000
177
1.7%
55.9%
79

Orlando
$682,830
$497,000
2815
1.6%
48.0%
80

Oviedo
$728,709
$649,450
182
1.1%
42.3%
77

Poinciana
$329,525
$314,995
256
0.4%
60.2%
132

Reunion
$1,836,174
$1,182,500
106
0.9%
49.1%
161

Saint Cloud
$570,564
$474,950
478
1.3%
73.6%
165

Sanford
$525,713
$415,000
369
0.8%
54.5%
99

Sorrento
$614,919
$481,615
106
0.9%
60.4%
88

Windermere
$2,125,828
$1,295,000
275
0.4%
46.5%
103

Winter Garden
$858,994
$700,000
592
0.5%
51.2%
85

Winter Springs
$566,574
$477,000
118
0.0%
47.5%
78

EasyStreet

Call to Schedule a Showing

(407) 967-1435

(407) 967-1435