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Winter Park Homes For Sale & Winter Park FL Real Estate

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 Today

  • 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 4 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 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3140

  • Year Built

    2018

  • $/SqFt

    $444

Brookshire Heights - Located within one of Winter Park’s top-rated school districts, this home is just minutes from Park Avenue, offering upscale shopping, dining, and entertainment. PALMANO GROUP RE BROKERAGE LLC.

Home For Sale $1,070,000

Inviting single-story home featuring a two-car garage, well-manicured lawn, and quaint front entrance under a sunny sky at 250 Cortland Ave, Winter Park, FL 32789
View Details 66 Photos
Sparkling pool with attached spa and patio, complemented by lush greenery and a privacy fence for a serene outdoor experience at 250 Cortland Ave, Winter Park, FL 32789
Bright living room boasts sleek hardwood floors, recessed lighting, and neutral walls for a comfortable and welcoming space 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 4 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.

Home For Sale $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 3 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 3 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.

Home For Sale $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 3 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.

Home For Sale $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 4 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 5 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 5 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 5 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 $465,000

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 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1387

  • Year Built

    1984

  • $/SqFt

    $335

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 4 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 $440,000

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 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1627

  • Year Built

    1981

  • $/SqFt

    $270

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 35 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 4 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.

Home For Sale $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 5 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.

Home For Sale $409,000

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 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1409

  • Year Built

    1958

  • $/SqFt

    $290

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.

Home For Sale $370,000

Charming single-story home featuring a brick facade, covered porch, and a bright blue front door at 1612 Eastbrook Blvd, Winter Park, FL 32792
View Details 30 Photos
Cozy living room with modern decor, plush seating, stylish rug, and view into the dining area at 1612 Eastbrook Blvd, Winter Park, FL 32792
Bright living room featuring stylish decor, wood-look floors, and an open layout into the dining area at 1612 Eastbrook Blvd, Winter Park, FL 32792
Inviting living room with modern decor, ample natural light, wood-look floors, and a cozy atmosphere at 1612 Eastbrook Blvd, Winter Park, FL 32792
On Market For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1240

  • Year Built

    1961

  • $/SqFt

    $298

Move-in ready and well-maintained, this home offers both comfort and convenience in a desirable Winter Park location. Schedule your showing today! EXP REALTY LLC.

Home For Sale $4,395,000

Lush backyard with mature trees, a walkway, and a waterfront view with a private dock at 1840 W Fawsett Rd, Winter Park, FL 32789
View Details 49 Photos
Stunning two-story home with manicured lawn, covered front porch, balcony, and elegant design at 1840 W Fawsett Rd, Winter Park, FL 32789
Inviting covered porch featuring comfortable seating, ceiling fans, and beautiful lake views at 1840 W Fawsett Rd, Winter Park, FL 32789
Cozy living room with a fireplace, high ceilings, large windows, and stylish furnishings at 1840 W Fawsett Rd, Winter Park, FL 32789
On Market For 6 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4129

  • Year Built

    1998

  • $/SqFt

    $1,064

Showings are by appointment only – schedule yours today. KELLY PRICE & COMPANY LLC.

Home For Sale $1,095,000

Charming single-story home featuring an attached two-car garage, brick chimney, and beautifully landscaped front yard at 1444 Pelican Bay Trl, Winter Park, FL 32792
View Details 57 Photos
An aerial view showcases the home's proximity to a tranquil lake surrounded by verdant trees at 1444 Pelican Bay Trl, Winter Park, FL 32792
Charming single-Gathering home with a two-car garage and a brick chimney framed by lush landscaping at 1444 Pelican Bay Trl, Winter Park, FL 32792
Home featuring a two-car garage and mature landscaping along with a large tree at 1444 Pelican Bay Trl, Winter Park, FL 32792
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3121

  • Year Built

    1984

  • $/SqFt

    $351

Don’t miss out—schedule a tour today! TRANSCEND REALTY.

Home For Sale $895,000

Charming single-story home featuring a well-manicured lawn and tasteful landscaping, creating a welcoming curb appeal at 2418 Whitehall Cir, Winter Park, FL 32792
View Details 36 Photos
An aerial view of a home showcasing the property lines and surrounding neighborhood with mature trees at 2418 Whitehall Cir, Winter Park, FL 32792
Modern kitchen features white cabinets, stainless steel appliances, and an island with a black base and quartz countertop at 2418 Whitehall Cir, Winter Park, FL 32792
Well-lit kitchen features white cabinets, stainless steel appliances, an island, and views of the outdoors at 2418 Whitehall Cir, Winter Park, FL 32792
On Market For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2134

  • Year Built

    1962

  • $/SqFt

    $419

DON’T MISS OUT, see the 3D tour, video or schedule your private showing today! CORCORAN PREMIER REALTY.

Home For Sale $785,000

Charming single-story home with well-manicured lawn and lush landscaping in a desirable neighborhood at 1312 Golfside Dr, Winter Park, FL 32792
View Details 27 Photos
Inviting front entrance with a decorative glass door, sconces, and beautiful stone accents at 1312 Golfside Dr, Winter Park, FL 32792
Elegant entryway with decorative door, leading to a living space with a built in workspace at 1312 Golfside Dr, Winter Park, FL 32792
Open-concept living space featuring a rustic sliding barn door, stylish floors, and modern kitchen at 1312 Golfside Dr, Winter Park, FL 32792
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1867

  • Year Built

    1979

  • $/SqFt

    $420

Greenview Winter Pines - Don’t miss this exceptional opportunity—schedule your private tour today! HOPKEY REALTY.

Home For Sale $699,000

Charming home featuring lush green lawn, vibrant landscaping, and warm lighting at 2368 Summerfield Rd, Winter Park, FL 32792
View Details 35 Photos
Sparkling pool area, perfect for relaxation and entertaining, surrounded by lush greenery at 2368 Summerfield Rd, Winter Park, FL 32792
Well-maintained home featuring lush landscaping and a welcoming front yard at 2368 Summerfield Rd, Winter Park, FL 32792
Charming home featuring lush landscaping, and a welcoming front yard at 2368 Summerfield Rd, Winter Park, FL 32792
On Market For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1904

  • Year Built

    1966

  • $/SqFt

    $367

This home’s prime location provides convenient access to I-4, Downtown Orlando, OIA and area attractions. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $525,000

Charming front patio with seating area, perfect for relaxing and enjoying the outdoors at 2463 Brookshire Ave, Winter Park, FL 32792
View Details 24 Photos
Dining area with modern chandelier, tile floors and view to back porch at 2463 Brookshire Ave, Winter Park, FL 32792
Well-maintained kitchen with stainless steel appliances and granite countertops at 2463 Brookshire Ave, Winter Park, FL 32792
Well-maintained kitchen with stainless steel appliances and granite countertops at 2463 Brookshire Ave, Winter Park, FL 32792
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1050

  • Year Built

    1959

  • $/SqFt

    $500

This home won't last long. HOME WISE REALTY GROUP, INC..

Pended $379,000

Charming single-story home featuring a lush front yard and a spacious driveway leading to an attached garage at 1873 Poinciana Rd, Winter Park, FL 32792
View Details 31 Photos
Inviting front porch with brick accents and a covered entrance, complemented by attractive landscaping at 1873 Poinciana Rd, Winter Park, FL 32792
Cozy living room with carpet flooring, a large window, and classic decor, creating a comfortable ambiance at 1873 Poinciana Rd, Winter Park, FL 32792
Open-concept living area featuring neutral walls and carpet, seamlessly connecting to adjacent spaces at 1873 Poinciana Rd, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1904

  • Year Built

    1970

  • $/SqFt

    $199

Winter Woods - This diamond in the rough is being sold AS IS—bring your creativity and make it shine! COLDWELL BANKER REALTY.

Home For Sale $1,500,000

Charming two-story home with stone accents, a well-manicured lawn, and a bright blue front door at 1741 Pine Ave, Winter Park, FL 32789
View Details 43 Photos
Inviting covered porch with stone accents, decorative columns, and cozy seating area with a blue front door at 1741 Pine Ave, Winter Park, FL 32789
Bright foyer featuring hardwood floors, an elegant chandelier, and a glimpse into the open-concept living space at 1741 Pine Ave, Winter Park, FL 32789
Elegant dining room with hardwood floors and decoratively appointed furniture adjacent to the living area at 1741 Pine Ave, Winter Park, FL 32789
On Market For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3297

  • Year Built

    2002

  • $/SqFt

    $455

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

Home For Sale $564,900

Charming single-story home featuring a manicured lawn, mature landscaping, and a two-car garage at 633 London Rd, Winter Park, FL 32792
View Details 50 Photos
Inviting front entrance with a blue door, red mulch landscaping and sidelights at 633 London Rd, Winter Park, FL 32792
Bright kitchen features tile floors, granite countertops, and stainless steel appliances at 633 London Rd, Winter Park, FL 32792
Open kitchen features a breakfast bar, stainless appliances, and tile flooring at 633 London Rd, Winter Park, FL 32792
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1772

  • Year Built

    1966

  • $/SqFt

    $319

Buyer to verify schools and room measurements. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $525,000

Charming home featuring mature trees, a brick accent wall, and a long driveway at 1307 Lindenwood Ln, Winter Park, FL 32792
View Details 40 Photos
Beautiful home exterior with a two-car garage and a long driveway at 1307 Lindenwood Ln, Winter Park, FL 32792
Spacious two-car garage offering ample parking and storage space at 1307 Lindenwood Ln, Winter Park, FL 32792
Bright dining room featuring hardwood floors, and stylish chandelier at 1307 Lindenwood Ln, Winter Park, FL 32792
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1612

  • Year Built

    1960

  • $/SqFt

    $326

Don’t miss out on this opportunity to live in the heart of it all. CENTRAL FLORIDA PRIME REAL ESTATE LLC.

Pended $439,900

Charming two-story home with a well-manicured lawn and a two-car garage at 1751 Meadowgold Ln, Winter Park, FL 32792
View Details 31 Photos
Spacious living room with a brick fireplace and a view of the second floor at 1751 Meadowgold Ln, Winter Park, FL 32792
Bright living room featuring wood floors, a brick fireplace, and a wood staircase at 1751 Meadowgold Ln, Winter Park, FL 32792
Open living room with wood floors and staircase at 1751 Meadowgold Ln, Winter Park, FL 32792
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1708

  • Year Built

    1986

  • $/SqFt

    $258

Don’t miss the opportunity to own this gem in one of Central Florida’s most desirable areas. Schedule your showing today! KELLER WILLIAMS WINTER PARK.

Home For Sale $1,775,000

Stunning two-story home with a modern design, two-car garage, stone accents, and meticulously landscaped yard at 1682 Arbor Park Dr, Winter Park, FL 32789
View Details 7 Photos
Bright, spacious kitchen with a large island, pendant lighting, modern appliances, and an adjacent dining area at 1682 Arbor Park Dr, Winter Park, FL 32789
Elegant living room with a modern fireplace, hardwood floors, ample seating, and natural light from the large sliding glass doors at 1682 Arbor Park Dr, Winter Park, FL 32789
Serene main bedroom with large windows, modern lighting, and a comfortable seating area, perfect for relaxation at 1682 Arbor Park Dr, Winter Park, FL 32789
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2950

  • Year Built

    2025

  • $/SqFt

    $602

Conwill Estates - Final construction details, finishes, and features may vary. COMPASS FLORIDA LLC.

Home For Sale $1,775,000

Elegant exterior showcases a modern two-story home with a two car garage and manicured lawn at 1702 Arbor Park Dr, Winter Park, FL 32789
View Details 7 Photos
Modern kitchen features a marble island with bar seating, pendant lighting, and stainless steel appliances at 1702 Arbor Park Dr, Winter Park, FL 32789
Bright living room boasts a modern fireplace and light hardwood floors with sliding doors to the pool at 1702 Arbor Park Dr, Winter Park, FL 32789
Stylish primary bedroom features a king bed, hardwood floors, modern lighting, and windows at 1702 Arbor Park Dr, Winter Park, FL 32789
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2950

  • Year Built

    2025

  • $/SqFt

    $602

Conwill Estates - Final construction details, finishes, and features may vary. COMPASS FLORIDA LLC.

Home For Sale $449,000

Charming single-story home with a manicured lawn and an attached two-car garage in a residential neighborhood at 5132 Goldenrod Place Rd, Winter Park, FL 32792
View Details 17 Photos
Charming single-story home with a well-manicured lawn and lush landscaping, showcasing curb appeal at 5132 Goldenrod Place Rd, Winter Park, FL 32792
Well-maintained home featuring a spacious driveway, attached garage, and welcoming curb appeal at 5132 Goldenrod Place Rd, Winter Park, FL 32792
Charming single-story home with a well-manicured lawn and lush landscaping, showcasing curb appeal at 5132 Goldenrod Place Rd, Winter Park, FL 32792
On Market For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1436

  • Year Built

    1973

  • $/SqFt

    $313

Don't miss out on this rare opportunity - schedule your private tour today! CENTRAL REALTY.

Pended $3,500,000

Breathtaking aerial view of a lakefront property with lush landscaping and direct access to the water at 443 Lakewood Dr, Winter Park, FL 32789
View Details 15 Photos
Charming one-story home featuring a large, well-manicured front lawn with mature trees and established landscaping at 443 Lakewood Dr, Winter Park, FL 32789
Spacious tiled back patio with white metal railing overlooking a serene lake view and mature trees at 443 Lakewood Dr, Winter Park, FL 32789
Inviting back patio with comfortable seating and stunning lake views, perfect for outdoor relaxation and entertaining at 443 Lakewood Dr, Winter Park, FL 32789
On Market For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2803

  • Year Built

    1954

  • $/SqFt

    $1,249

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

Home For Sale $1,375,000

Large two-car garage featuring an extended driveway and lush landscaping at 1213 Richmond Rd, Winter Park, FL 32789
View Details 27 Photos
An eye-level shot of the home's front exterior with the garage on the left at 1213 Richmond Rd, Winter Park, FL 32789
Welcoming foyer featuring hardwood floors, decorative sconces, and beautiful wrought iron railing at 1213 Richmond Rd, Winter Park, FL 32789
Kitchen with stainless appliances, modern cabinetry, and granite countertops at 1213 Richmond Rd, Winter Park, FL 32789
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3204

  • Year Built

    1925

  • $/SqFt

    $429

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

Home For Sale $795,000

Charming two-story home with lush palm trees and a brick paved driveway offers curb appeal at 1344 Blue Stem Lane, Winter Park, FL 32792
View Details 26 Photos
Close up of the front door with decorative glass, brick patio, and stucco exterior at 1344 Blue Stem Lane, Winter Park, FL 32792
Bright kitchen with white cabinets, stainless steel appliances, and stone countertops at 1344 Blue Stem Lane, Winter Park, FL 32792
Spacious living room with neutral carpeting, high ceilings, and sliding glass doors to backyard at 1344 Blue Stem Lane, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2589

  • Year Built

    2022

  • $/SqFt

    $307

Hawks Crest - Don’t miss your chance to own your dream home, schedule your tour today and experience the lifestyle you have been looking for! Welcome home. CASTLE & COTTAGE REALTY LLC.

Home For Sale $579,500

Charming blue single-story home with a well-manicured lawn and inviting front porch at 5073 Lake Howell Rd, Winter Park, FL 32792
View Details 72 Photos
Inviting front porch area with colorful chairs, a small table and decorative plants at 5073 Lake Howell Rd, Winter Park, FL 32792
A well-maintained single-story home with attached garage and a long driveway at 5073 Lake Howell Rd, Winter Park, FL 32792
Refreshing in-ground pool surrounded by a concrete patio and a screened-in lanai at 5073 Lake Howell Rd, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    5

  • Full Bath(s)

    2

  • Sq. Ft.

    2272

  • Year Built

    1956

  • $/SqFt

    $255

Tanglewood - Located in the highly rated Seminole County School District, this home is a must-see. Schedule your showing today! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $569,000

Charming single-story home with a well-maintained lawn and mature trees in a quiet residential neighborhood at 4029 Cool Water Ct, Winter Park, FL 32792
View Details 38 Photos
A well-maintained single-story home features a two-car garage and a neatly landscaped front yard with mature trees at 4029 Cool Water Ct, Winter Park, FL 32792
Charming single-story home featuring a blue front door, complemented by mature trees and a well-manicured lawn at 4029 Cool Water Ct, Winter Park, FL 32792
Bright living room boasts wood floors, a ceiling fan, and a bay window that floods the space with natural light at 4029 Cool Water Ct, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 12 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2733

  • Year Built

    1979

  • $/SqFt

    $208

Lake Waunatta Woods - Don’t miss the opportunity to make this your dream home in this fantastic location! Schedule a showing today! MAGNUS REALTY GROUP LLC.

Pended $525,000

Charming single story home featuring a manicured lawn and mature landscaping at 2019 Loch Berry Rd, Winter Park, FL 32792
View Details 12 Photos
Expansive backyard featuring mature trees and offering ample green space at 2019 Loch Berry Rd, Winter Park, FL 32792
Aerial view of the property in a neighborhood featuring mature trees and well-maintained homes at 2019 Loch Berry Rd, Winter Park, FL 32792
Aerial view of property lines in a neighborhood close to a pool and park at 2019 Loch Berry Rd, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1425

  • Year Built

    1957

  • $/SqFt

    $368

This wonderful neighborhood is also within walking distance to the Cady Way Trail, Cady Way Pool & Pickleball Courts, Showalter Fields & Park and Excellent Winter Park Schools! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $409,999

Charming single-story home with red brick accents and mature landscaping at 1109 Denton Rd, Winter Park, FL 32792
View Details 39 Photos
Single-story home with covered parking, red brick accents and mature landscaping at 1109 Denton Rd, Winter Park, FL 32792
Bright kitchen with stainless steel appliances and a large center island at 1109 Denton Rd, Winter Park, FL 32792
Bright kitchen with stainless steel appliances and a large center island at 1109 Denton Rd, Winter Park, FL 32792
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1236

  • Year Built

    1963

  • $/SqFt

    $332

Come experience Winter Park living at its finest! KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $519,900

Charming single-story home with well-manicured lawn, brick driveway and attached garage at 519 Cornwall Rd, Winter Park, FL 32792
View Details 42 Photos
Covered front porch with brick flooring and white columns offering a welcoming entrance at 519 Cornwall Rd, Winter Park, FL 32792
Foyer with tile flooring, decorative glass front door and view to dining room at 519 Cornwall Rd, Winter Park, FL 32792
Bright dining room featuring wood floors, wainscoting, crown molding and large window at 519 Cornwall Rd, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1630

  • Year Built

    1965

  • $/SqFt

    $319

Easy access to Downtown Orlando, International Airport and 408 and 417. RE/MAX 200 REALTY.

Home For Sale $465,000

Charming single-story home boasts a well-maintained lawn, manicured landscaping, and classic shutters at 7565 Dockside St, Winter Park, FL 32792
View Details 42 Photos
Inviting foyer with decorative front door, neutral paint, tile floors, and a charming straw hat on the closet door at 7565 Dockside St, Winter Park, FL 32792
Open-concept living area with hardwood floors flowing into adjacent dining and kitchen spaces at 7565 Dockside St, Winter Park, FL 32792
Comfortable living room featuring hardwood floors, a ceiling fan, and a large sectional sofa at 7565 Dockside St, Winter Park, FL 32792
On Market For 13 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1948

  • Year Built

    1977

  • $/SqFt

    $239

Woodcrest - VA, FHA, and conventional financing are all welcome, so don’t wait – schedule your private showing today and make this dream home yours! PREMIUM PROPERTIES REAL ESTATE.

Pended $355,000

Charming single-story home featuring a well-manicured lawn, brick facade, and a welcoming blue front door at 1493 Hyde Park Dr, Winter Park, FL 32792
View Details 37 Photos
Charming single-story home featuring a well-manicured lawn, brick facade, and a welcoming blue front door at 1493 Hyde Park Dr, Winter Park, FL 32792
Close-up view of front door with blue paint, wreath and decorative plants at 1493 Hyde Park Dr, Winter Park, FL 32792
Comfortable living room featuring a spacious gray couch, ceiling fan and natural light at 1493 Hyde Park Dr, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1408

  • Year Built

    1989

  • $/SqFt

    $252

Don't miss this incredible opportunity- schedule your private showing today! HOMEVEST REALTY.

Home For Sale $4,875,000

Stunning modern two-story home with large windows, crisp white exterior, and meticulously landscaped front yard at 229 Alexander Pl, Winter Park, FL 32789
View Details 65 Photos
Modern two-story home with manicured lawn and beautiful landscaping at twilight at 229 Alexander Pl, Winter Park, FL 32789
Stunning contemporary home with a modern stone facade, lush landscaping, and a clean architectural design at 229 Alexander Pl, Winter Park, FL 32789
Detailed view of the entryway, highlighting the modern door, stone facade, and the sleek, minimalist design at 229 Alexander Pl, Winter Park, FL 32789
On Market For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4431

  • Year Built

    2012

  • $/SqFt

    $1,100

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

Pended $4,799,900

Beautiful modern two-story home with a manicured lawn, stone accents, and a spacious three-car garage at 1691 Chestnut Ave, Winter Park, FL 32789
View Details 69 Photos
Beautiful modern two-story home with a manicured lawn, stone accents, and a spacious three-car garage at 1691 Chestnut Ave, Winter Park, FL 32789
Beautiful modern two-story home with manicured landscaping and an inviting, paved driveway and walkway at 1691 Chestnut Ave, Winter Park, FL 32789
Modern two-story home featuring manicured landscaping and an inviting paved driveway and walkway, lit for evening at 1691 Chestnut Ave, Winter Park, FL 32789
On Market For 14 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4582

  • Year Built

    2024

  • $/SqFt

    $1,048

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

Home For Sale $749,000

Charming single-story brick home featuring a well-manicured lawn and a two-car garage at 1321 Medinah Ct, Winter Park, FL 32792
View Details 34 Photos
Charming front entrance featuring lush landscaping and a well-maintained lawn at 1321 Medinah Ct, Winter Park, FL 32792
Inviting entryway featuring wood floors, decorative columns, and a glass accent front door at 1321 Medinah Ct, Winter Park, FL 32792
Bright and airy living space with hardwood floors and decorative columns at 1321 Medinah Ct, Winter Park, FL 32792
On Market For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2446

  • Year Built

    1979

  • $/SqFt

    $306

Greenview Winter Pines - There is an optional HOA in the Winter Park Pines community that puts on neighborhood programming for members. MILLER GRANT AND COMPANY.

Home For Sale $350,000

Charming single-story home with a one-car garage, manicured lawn, and light yellow paint at 3361 Hamlet Loop, Winter Park, FL 32792
View Details 30 Photos
Beautiful single-story home boasting well-maintained landscaping, a driveway, and cheerful yellow siding at 3361 Hamlet Loop, Winter Park, FL 32792
Inviting one-story house features a driveway, nice lawn, and bright yellow exterior paint at 3361 Hamlet Loop, Winter Park, FL 32792
Community sign for 'Hamlet in the Park' with lush landscaping at 3361 Hamlet Loop, Winter Park, FL 32792
On Market For 14 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1114

  • Year Built

    1993

  • $/SqFt

    $314

Villas Of Casselberry - Close to 417 and 408 for ease of travel. EMPIRE NETWORK REALTY.

Pended $4,600,000

Stunning lakefront home featuring a pool, covered patio, and lush landscaping at 2118 Lake Dr, Winter Park, FL 32789
View Details 41 Photos
Beautiful two-story home with a brick driveway, manicured landscaping, and a three-car garage at 2118 Lake Dr, Winter Park, FL 32789
Inviting covered porch with wood floors, landscaping, and views of the property at 2118 Lake Dr, Winter Park, FL 32789
Outdoor patio area with seating overlooking the waterfront at 2118 Lake Dr, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 15 Days

  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    6000

  • Year Built

    2012

  • $/SqFt

    $767

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

Home For Sale $429,900

Charming single-story home with a well-manicured lawn, complemented by a quaint orange front door at 1975 Staunton Ave, Winter Park, FL 32789
View Details 34 Photos
Charming single-story home with a well-manicured lawn, complemented by a quaint orange front door at 1975 Staunton Ave, Winter Park, FL 32789
Bright living room with hardwood floors, a ceiling fan and stylish furniture; perfect for relaxing and entertaining at 1975 Staunton Ave, Winter Park, FL 32789
Bright living room featuring hardwood floors, a ceiling fan and plenty of natural light at 1975 Staunton Ave, Winter Park, FL 32789
On Market For 15 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1200

  • Year Built

    1949

  • $/SqFt

    $358

Karolina On Killarney - Conveniently located near I-4, Park Avenue, Winter Park Village, Dubsdread Golf Course, restaurants and shopping and downtown Orlando. ABSOLUTE REALTY GROUP, LLC.

Pended $6,950,000

Elegant two-story home with manicured landscaping and a grand entrance, framed by mature palm trees and decorative driveway at 1400 Alabama Dr, Winter Park, FL 32789
View Details 99 Photos
Stunning Mediterranean home featuring a circular driveway and meticulously landscaped grounds with mature palm trees at 1400 Alabama Dr, Winter Park, FL 32789
Elegant stone entryway featuring a dark wood door with decorative glass and stylish outdoor lighting at 1400 Alabama Dr, Winter Park, FL 32789
Aerial view of the luxurious home features a tile roof, mature landscaping, and a stunning backyard pool and spa at 1400 Alabama Dr, Winter Park, FL 32789
On Market For 17 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    7916

  • Year Built

    1996

  • $/SqFt

    $878

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

Home For Sale $1,799,000

An impressive exterior elevation view of a white two-story home with a clay tile roof and meticulously manicured landscaping at 1731 Windsor Dr, Winter Park, FL 32789
View Details 12 Photos
The spacious living room is highlighted by a fireplace, vaulted ceilings, and natural light from abundant windows at 1731 Windsor Dr, Winter Park, FL 32789
A chef's kitchen with a large island, stainless steel appliances, and an open design creates an inviting space at 1731 Windsor Dr, Winter Park, FL 32789
The light filled living room with an open-concept design provides seamless access to the outdoor pool and kitchen at 1731 Windsor Dr, Winter Park, FL 32789
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3669

  • Year Built

    2007

  • $/SqFt

    $490

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

Viewing HOMES 1 to 50 of 273

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
$534,056
$428,000
131
0.8%
47.3%
87

Apopka
$528,641
$459,146
571
1.2%
50.1%
89

Belle Isle
$846,109
$699,900
27
0.0%
51.9%
75

Casselberry
$454,693
$438,500
89
2.2%
47.2%
68

Celebration
$1,406,095
$1,175,000
47
0.0%
48.9%
115

Champions Gate
$687,428
$699,990
21
0.0%
52.4%
248

Chuluota
$719,896
$599,999
23
0.0%
47.8%
46

Clermont
$575,547
$495,000
675
0.7%
50.1%
84

Gotha
$1,077,831
$692,495
14
0.0%
28.6%
52

Groveland
$481,846
$416,495
262
0.8%
51.1%
84

Harmony
$445,356
$419,900
70
0.0%
28.6%
93

Kissimmee
$515,834
$440,000
2370
1.5%
47.8%
103

Longwood
$767,573
$550,000
183
1.1%
50.8%
83

Maitland
$846,807
$622,000
74
1.4%
50.0%
93

Minneola
$557,205
$533,610
131
0.8%
38.9%
92

Montverde
$1,455,653
$1,095,240
54
0.0%
42.6%
127

Ocoee
$525,103
$466,000
179
1.7%
53.1%
82

Orlando
$688,840
$488,500
2774
1.7%
47.3%
80

Oviedo
$718,920
$630,000
187
1.1%
43.9%
77

Poinciana
$332,287
$315,000
254
0.8%
57.9%
132

Reunion
$1,915,675
$1,230,000
105
1.0%
44.8%
161

Saint Cloud
$556,789
$466,990
570
1.1%
71.9%
156

Sanford
$514,090
$413,990
383
1.0%
53.8%
100

Sorrento
$587,347
$457,995
108
1.9%
67.6%
92

Windermere
$2,139,195
$1,285,970
269
0.4%
43.9%
111

Winter Garden
$849,275
$699,000
597
0.5%
47.4%
85

Winter Springs
$587,218
$475,000
127
0.0%
39.4%
73

EasyStreet

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