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Winter Park Homes For Sale & Winter Park FL Real Estate

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 Today

  • 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 $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 Today

  • 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 Today

  • 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.

Home For Sale $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 Today

  • 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 Today

  • 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 Today

  • 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 2 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 Today

  • 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 Today

  • 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 2 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 $515,000

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 4 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1140

  • Year Built

    1953

  • $/SqFt

    $452

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 4 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 6 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.

Home For Sale $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 6 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 8 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 6 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 6 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.

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.

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 4 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 $449,900

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 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1788

  • Year Built

    1989

  • $/SqFt

    $252

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 $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 7 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 $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 6 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 7 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 9 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.

Home For Sale $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 9 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 9 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 9 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 9 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.

Pended $525,000

Charming two-story home with a manicured lawn, lush trees and attached garage at 1810 Taylor Ave, Winter Park, FL 32789
View Details 1 Photo
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1396

  • Year Built

    1977

  • $/SqFt

    $376

Under contract. Listing agent is the owner. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $495,700

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 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2014

  • Year Built

    1982

  • $/SqFt

    $246

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

Home For Sale $3,400,000

Stunning brick home with a charming front porch, featuring white columns, black shutters, and inviting curb appeal at 1911 Stonehurst Rd, Winter Park, FL 32789
View Details 37 Photos
Spacious backyard features a brick patio, manicured hedges, and a cozy fire pit area at 1911 Stonehurst Rd, Winter Park, FL 32789
Aerial view of a luxury home showcasing its manicured backyard and sparkling swimming pool at 1911 Stonehurst Rd, Winter Park, FL 32789
Inviting front porch with rocking chairs, a decorative rug, and classic brick facade at 1911 Stonehurst Rd, Winter Park, FL 32789
On Market For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    5097

  • Year Built

    2001

  • $/SqFt

    $667

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

Home For Sale $875,000

Charming single-story home featuring a well-manicured lawn, covered porch, and inviting curb appeal at 1832 Magnolia Ave, Winter Park, FL 32789
View Details 31 Photos
Charming single-story home at dusk, featuring a well-manicured lawn and inviting curb appeal at 1832 Magnolia Ave, Winter Park, FL 32789
Inviting entryway showcasing wood floors, a decorative front door, and neutral wall paint at 1832 Magnolia Ave, Winter Park, FL 32789
Bright living room with stylish decor, wood flooring, modern lighting, and a comfortable sectional sofa at 1832 Magnolia Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 11 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2910

  • Year Built

    1954

  • $/SqFt

    $301

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

Pended $420,000

Charming home with a blue metal roof, stone accents, and well-maintained landscaping at 1189 Lazy Hollow Pl, Winter Park, FL 32792
View Details 27 Photos
Beautiful exterior view with a well-manicured lawn and metal roof at 1189 Lazy Hollow Pl, Winter Park, FL 32792
Aerial view of home showcasing backyard pool, patio, and fenced yard at 1189 Lazy Hollow Pl, Winter Park, FL 32792
Bright living room with tile flooring, neutral walls, and ample natural light at 1189 Lazy Hollow Pl, Winter Park, FL 32792
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1525

  • Year Built

    1984

  • $/SqFt

    $275

Springview - Don’t miss your chance to make this exceptional property yours, schedule your private tour today! ORLANDO EXPERT REALTY LLC.

Home For Sale $950,000

Inviting two-story home boasting a manicured lawn, lush landscaping, and a paver driveway at 5325 Cypress Reserve Pl, Winter Park, FL 32792
View Details 61 Photos
Charming two-story home featuring a brick paver driveway, lush landscaping, and a side-entry garage at 5325 Cypress Reserve Pl, Winter Park, FL 32792
A beautifully landscaped two-story home with mature palm trees, lush shrubbery, and vibrant green lawn at 5325 Cypress Reserve Pl, Winter Park, FL 32792
Two-story home boasting a brick paver driveway, mature trees, manicured landscaping, and a side-entry garage at 5325 Cypress Reserve Pl, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 12 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3598

  • Year Built

    1998

  • $/SqFt

    $264

Homes in Cypress Reserve rarely become available—don’t miss this one! LPT REALTY, LLC.

Home For Sale $2,895,000

Beautiful two-story home featuring a red tile roof, white stucco and meticulously landscaped front yard with tropical palm trees at 1630 Lasbury Ave, Winter Park, FL 32789
View Details 51 Photos
Elegant stucco home with a red tile roof, framed by palm trees and a circular driveway offering ample parking space at 1630 Lasbury Ave, Winter Park, FL 32789
Long brick paver driveway and lush landscaping leading to beautiful homes; palm tree shadows dappling the walkway at 1630 Lasbury Ave, Winter Park, FL 32789
Bright living room with hardwood floors, a piano, French doors to a pool, and neutral-toned furniture at 1630 Lasbury Ave, Winter Park, FL 32789
On Market For 14 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    4912

  • Year Built

    2003

  • $/SqFt

    $589

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

Home For Sale $1,395,000

Beautiful two-story home featuring a basketball hoop and lush landscaping at 2536 Brookshire Ave, Winter Park, FL 32792
View Details 49 Photos
Beautiful two-story home featuring a basketball hoop and lush landscaping at 2536 Brookshire Ave, Winter Park, FL 32792
Charming two-story home with a well-manicured front lawn and basketball court at 2536 Brookshire Ave, Winter Park, FL 32792
Stately two-story house featuring an attached two-car garage and welcoming entrance at 2536 Brookshire Ave, Winter Park, FL 32792
On Market For 13 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3140

  • Year Built

    2018

  • $/SqFt

    $444

Brookshire Heights - Enjoy nearby outdoor recreation at Ward Park, as well as wellness amenities at the Center for Health & Wellbeing. PALMANO GROUP RE BROKERAGE LLC.

Home For Sale $1,070,000

Charming single-story home with a well-manicured lawn, lush landscaping, and a spacious two-car garage at 250 Cortland Ave, Winter Park, FL 32789
View Details 68 Photos
Aerial view of a home with a private pool, lush greenery, and neatly fenced yard providing a serene retreat at 250 Cortland Ave, Winter Park, FL 32789
Bright living room features vaulted ceiling, hardwood floors, sliding glass doors to a pool, and neutral decor at 250 Cortland Ave, Winter Park, FL 32789
Spacious game room with a pool table, drum set, hardwood floors, and skylights, perfect for entertaining and leisure at 250 Cortland Ave, Winter Park, FL 32789
On Market For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2114

  • Year Built

    1981

  • $/SqFt

    $506

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

Pended $849,000

Charming two-story home with a modern design, manicured lawn, and brick paver driveway at 705 Baffie Ave, Winter Park, FL 32789
View Details 40 Photos
Inviting front entrance showcasing a dark-colored front door, brick paver walkway, and attached garage at 705 Baffie Ave, Winter Park, FL 32789
Bright kitchen features a large center island, stainless steel appliances, and modern pendant lighting at 705 Baffie Ave, Winter Park, FL 32789
Spacious kitchen with a long island featuring stainless steel appliances, hardwood floors, and pendant lighting at 705 Baffie Ave, Winter Park, FL 32789
On Market For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2563

  • Year Built

    2020

  • $/SqFt

    $331

Dubsdread Heights - Don’t miss your chance to make it yours, schedule your showing today. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $625,000

Charming single-story home featuring a bright red front door and lush green lawn at 230 S Ranger Blvd, Winter Park, FL 32792
View Details 47 Photos
A beautifully landscaped home with a circular driveway and an attached two-car garage at 230 S Ranger Blvd, Winter Park, FL 32792
A charming front porch is adorned with a bright red door and manicured landscaping at 230 S Ranger Blvd, Winter Park, FL 32792
A bright open-concept living room flows into a stylish kitchen and dining area at 230 S Ranger Blvd, Winter Park, FL 32792
On Market For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2309

  • Year Built

    1963

  • $/SqFt

    $271

Enjoy mature, green trees, sidewalks for biking and walking in this charming and sought-after neighborhood. KELLY PRICE & COMPANY LLC.

Pended $539,900

Charming single-story home featuring a well-manicured lawn, a two-car garage, and tasteful landscaping at 2335 Coldstream Dr, Winter Park, FL 32792
View Details 27 Photos
Inviting single-story home showcasing a spacious driveway, a two-car garage, and lush green lawn at 2335 Coldstream Dr, Winter Park, FL 32792
Bright foyer with new wood flooring, stylish console table with decor, and exterior glass paneled doors at 2335 Coldstream Dr, Winter Park, FL 32792
Comfortable living room featuring a decorative chandelier, neutral paint, and stylish furniture at 2335 Coldstream Dr, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1466

  • Year Built

    1958

  • $/SqFt

    $368

Brookshire Heights - All electrical panels have been updated. RE/MAX TOWN & COUNTRY REALTY.

Pended $3,250,000

Stunning two-story home with modern design, manicured landscaping, and a welcoming circular driveway at 1833 Loch Berry Rd, Winter Park, FL 32789
View Details 48 Photos
Beautiful two-story home showcasing modern architecture, a well-maintained lawn, and a spacious driveway at 1833 Loch Berry Rd, Winter Park, FL 32789
Elegant home entrance featuring a striking arched doorway, meticulous landscaping, and stone walkway at 1833 Loch Berry Rd, Winter Park, FL 32789
Bright foyer with herringbone wood floors, designer lighting, and an arched entryway, offering a grand welcome at 1833 Loch Berry Rd, Winter Park, FL 32789
On Market For 9 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4770

  • Year Built

    2025

  • $/SqFt

    $681

Kenilworth Shores - Don’t miss your opportunity to own this stunning Winter Park home crafted by renowned builder Vimaro Homes. COMPASS FLORIDA LLC.

Home For Sale $1,475,000

Charming brick home with manicured lawn, brick pathway, and lush landscaping, creating inviting curb appeal at 1600 Barcelona Way, Winter Park, FL 32789
View Details 65 Photos
Charming brick home with manicured lawn, brick pathway, and lush landscaping, creating inviting curb appeal at 1600 Barcelona Way, Winter Park, FL 32789
Charming brick home with manicured lawn, brick pathway, and lush landscaping, creating inviting curb appeal at 1600 Barcelona Way, Winter Park, FL 32789
Charming brick home with manicured lawn, brick pathway, and lush landscaping, creating inviting curb appeal at 1600 Barcelona Way, Winter Park, FL 32789
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3014

  • Year Built

    1972

  • $/SqFt

    $489

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

Home For Sale $750,000

Charming single-story home featuring a modern design, dark trim, two car garage, and a well-manicured front yard at 607 Dunblane Dr, Winter Park, FL 32792
View Details 44 Photos
Inviting front entrance featuring a decorative glass door, contemporary lighting, and manicured landscaping at 607 Dunblane Dr, Winter Park, FL 32792
Bright foyer showcasing a modern wood slat accent wall, leading into an open-concept kitchen at 607 Dunblane Dr, Winter Park, FL 32792
Modern bathroom with stylish black tile, sleek fixtures, and minimalist design at 607 Dunblane Dr, Winter Park, FL 32792
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2046

  • Year Built

    1964

  • $/SqFt

    $367

Kenilworth Shores - Don’t miss your chance to experience Winter Park living at its best—schedule your showing today! CHARLES RUTENBERG REALTY ORLANDO.

Pended $589,000

Charming single story home featuring a gravel driveway, covered entryway, and well maintained lawn at 3006 Northwood Blvd, Winter Park, FL 32789
View Details 44 Photos
Charming single story home featuring a gravel driveway, covered entryway, and well maintained lawn at 3006 Northwood Blvd, Winter Park, FL 32789
A close up of the front door, shows the house number, covered parking, and clean well kept yard at 3006 Northwood Blvd, Winter Park, FL 32789
Well manicured yard with healthy plants and flowers, featuring a short retaining wall around the landscaped area at 3006 Northwood Blvd, Winter Park, FL 32789
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1710

  • Year Built

    1953

  • $/SqFt

    $344

Northwood Terrace - Don't miss out and schedule your private tour today! CREEGAN GROUP.

Home For Sale $457,900

Reduced By $7,100

Charming single-Gathering home featuring well-manicured landscaping and a brick-accented facade with attached garage at 4442 Glenview Ln, Winter Park, FL 32792
View Details 46 Photos
Sunset view of a charming single-Gathering home with a brick-accented facade and well-manicured front lawn at 4442 Glenview Ln, Winter Park, FL 32792
Inviting front porch with red door, brick columns, house number and colorful landscaping at 4442 Glenview Ln, Winter Park, FL 32792
Bright living room showcasing tile floors, stylish furnishings, and an open concept layout to the kitchen at 4442 Glenview Ln, Winter Park, FL 32792
On Market For 14 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1387

  • Year Built

    1984

  • $/SqFt

    $330

Glenmoor - This home comes with a timed SPRINKLER SYSTEM. Schedule your private showing today! REPETTO REALTY GROUP LLC.

Home For Sale $450,000

Charming single-story home featuring a well-maintained lawn and an attached two-car garage with a screen door at 4991 Tangerine Ave, Winter Park, FL 32792
View Details 26 Photos
Single-story home with a well-manicured lawn, driveway, mature trees, and an attached two-car garage with a screen door at 4991 Tangerine Ave, Winter Park, FL 32792
This single-story home features a well-manicured lawn, mature trees, and a charming exterior at 4991 Tangerine Ave, Winter Park, FL 32792
Inviting front entrance with a well-lit porch, decorative stone accents, a flower bush, and the house number displayed at 4991 Tangerine Ave, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2124

  • Year Built

    1972

  • $/SqFt

    $212

Wrenwood Heights - Don’t miss this incredible opportunity! KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $425,000

Reduced By $15,000

Landscaped front yard of light blue home with palm tree and mature tree providing curb appeal at 3121 Heartwood Ave, Winter Park, FL 32792
View Details 32 Photos
Well-maintained home exterior features a charming front porch with a white garage door at 3121 Heartwood Ave, Winter Park, FL 32792
Spacious living room with tile floors, a modern ceiling fan, and a large TV at 3121 Heartwood Ave, Winter Park, FL 32792
Open living room features a large TV and sliding doors to the backyard at 3121 Heartwood Ave, Winter Park, FL 32792
On Market For 15 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1627

  • Year Built

    1981

  • $/SqFt

    $261

Bel Aire Pines - Zoned for winter Park High School, this amazing location offers amazing dining and shopping being close to Downtown Winter Park and Orlando and easy access to major highways. Schedule your private showing today! KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $410,000

Charming single-story home featuring a spacious driveway, well-maintained lawn, and mature landscaping at 1021 Mare Bello Dr, Winter Park, FL 32792
View Details 37 Photos
Charming single-story home with a spacious driveway, manicured lawn, and vibrant landscaping during sunset at 1021 Mare Bello Dr, Winter Park, FL 32792
Charming single-story home boasting an oversized driveway, a lush lawn, and vibrant landscaping at 1021 Mare Bello Dr, Winter Park, FL 32792
Open-concept living area featuring new floors, neutral paint, and seamless flow into the kitchen at 1021 Mare Bello Dr, Winter Park, FL 32792
On Market For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1730

  • Year Built

    1965

  • $/SqFt

    $237

Eastbrook - This is a prime location and close to everything - restaurants, shopping, Full Sail, UCF and a short distance to attractions and beaches. THE WILKINS WAY LLC.

Pended $410,000

Charming single-story home with a well-maintained lawn and mature trees in a desirable neighborhood at 1921 Taylor Ave, Winter Park, FL 32792
View Details 14 Photos
An aerial view showcasing the home's roof, driveway, and surrounding mature trees at 1921 Taylor Ave, Winter Park, FL 32792
Detailed floor plan of a single-story home showing the layout of rooms and measurements at 1921 Taylor Ave, Winter Park, FL 32792
An overhead view of the property, illustrating its location in a residential neighborhood with mature trees at 1921 Taylor Ave, Winter Park, FL 32792
On Market For 15 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1322

  • Year Built

    1956

  • $/SqFt

    $310

Eastgate - Don't miss taking advantage of this opportunity to invest in a prime lot in the highly desirable Winter Park area with easy access to everything the area has to offer. The possibilities are endless! EXP REALTY LLC.

Pended $389,000

Reduced By $20,000

Charming single-story home with brick facade, walkway, and landscaped front yard under a clear, blue sky at 2805 Bongart Rd, Winter Park, FL 32792
View Details 23 Photos
Expansive front yard of a brick single story home with mature landscaping and blue skies at 2805 Bongart Rd, Winter Park, FL 32792
Single story home with brick accents, symmetrical windows, and a lush green lawn on a sunny day at 2805 Bongart Rd, Winter Park, FL 32792
Open-concept living room featuring hardwood floors, brick accent wall, and seamless access to the dining area at 2805 Bongart Rd, Winter Park, FL 32792
On Market For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1409

  • Year Built

    1958

  • $/SqFt

    $276

Winter Park Estates - This home offers an incredible opportunity in one of Winter Park's most desirable locations—schedule your showing today! CENTURY 21 CARIOTI.

Viewing HOMES 1 to 50 of 278

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 407-485-1814 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$533,454
$439,000
127
1.6%
50.4%
86

Apopka
$531,798
$460,000
553
1.3%
50.8%
93

Belle Isle
$829,763
$667,496
26
0.0%
42.3%
64

Casselberry
$453,535
$438,500
93
2.2%
51.6%
68

Celebration
$1,380,950
$1,127,000
50
0.0%
48.0%
117

Champions Gate
$684,395
$699,990
21
0.0%
52.4%
258

Chuluota
$816,296
$674,900
25
0.0%
48.0%
45

Clermont
$574,704
$496,070
698
0.7%
51.1%
84

Gotha
$1,069,222
$692,495
12
0.0%
33.3%
57

Groveland
$478,849
$410,990
259
0.8%
52.9%
84

Harmony
$442,009
$419,950
74
0.0%
28.4%
87

Kissimmee
$516,294
$440,000
2379
1.7%
48.2%
103

Longwood
$763,610
$565,000
191
1.6%
52.9%
81

Maitland
$868,940
$619,500
72
2.8%
52.8%
93

Minneola
$557,033
$535,000
133
0.8%
38.3%
92

Montverde
$1,470,733
$1,112,124
55
0.0%
41.8%
129

Ocoee
$525,335
$465,000
177
1.7%
57.6%
81

Orlando
$684,610
$490,000
2842
1.7%
47.6%
80

Oviedo
$715,112
$645,000
185
1.1%
43.8%
79

Poinciana
$328,177
$314,990
267
0.4%
59.6%
129

Reunion
$1,826,429
$1,190,000
107
0.9%
49.5%
160

Saint Cloud
$564,309
$472,000
522
1.1%
73.2%
165

Sanford
$520,590
$415,000
375
1.1%
55.7%
99

Sorrento
$609,482
$470,000
113
1.8%
62.8%
87

Windermere
$2,169,944
$1,349,500
274
0.4%
46.4%
106

Winter Garden
$850,336
$698,500
598
0.5%
50.7%
86

Winter Springs
$581,564
$477,000
116
0.0%
45.7%
77

EasyStreet

Call to Schedule a Showing

(407) 485-1814

(407) 485-1814