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323 Results

View 323 Winter Park Florida Homes for Sale

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 55 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 $1,996,000

Reduced By $204,000

Stunning aerial view of estate home with large brick driveway and beautiful landscaping close to the water at 4469 Old Bear Run, Winter Park, FL 32792
View Details 74 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
Scenic water view featuring a beautiful sunset with bright oranges and yellows and peaceful reflections on the water at 4469 Old Bear Run, Winter Park, FL 32792
Scenic water view featuring a sunset with bright oranges and yellows and peaceful reflections on the water at 4469 Old Bear Run, Winter Park, FL 32792
On Market For 54 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4288

  • Year Built

    1978

  • $/SqFt

    $465

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

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 55 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 $685,000

Reduced By $14,000

Charming single-story home featuring a stone facade, solar panels, a two-car garage and a curved driveway at 690 S Lakemont Ave, Winter Park, FL 32792
View Details 34 Photos
Charming single-story home with solar panels, a stone facade, two-car garage, and a curved driveway at 690 S Lakemont Ave, Winter Park, FL 32792
Inviting single-story home featuring solar panels, a stone facade, a two-car garage and a curved driveway at 690 S Lakemont Ave, Winter Park, FL 32792
Comfortable living room with hardwood floors, bookshelves, and sliding glass doors to the pool area at 690 S Lakemont Ave, Winter Park, FL 32792
On Market For 45 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1897

  • Year Built

    1965

  • $/SqFt

    $361

Kenilworth Shores - The seller is offering a $10,000 credit to buyer. MARK SPAIN REAL ESTATE.

Pended $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 54 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 $585,000

Reduced By $15,000

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 54 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1856

  • Year Built

    1961

  • $/SqFt

    $315

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

Home For Sale $549,000

Reduced By $20,000

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 46 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1656

  • Year Built

    1955

  • $/SqFt

    $332

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

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
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 $489,000

Reduced By $26,000

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 58 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1140

  • Year Built

    1953

  • $/SqFt

    $429

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

Home For Sale $479,000

Reduced By $31,000

Charming single-story home featuring a garage and a driveway for additional parking at 2829 Aloma Ave, Winter Park, FL 32792
View Details 44 Photos
Refreshing pool with steps for easy access, surrounded by a patio and backyard at 2829 Aloma Ave, Winter Park, FL 32792
Cozy living room featuring a fireplace, wood floors, and a relaxed atmosphere at 2829 Aloma Ave, Winter Park, FL 32792
Functional kitchen with stainless steel appliances and ample counter space at 2829 Aloma Ave, Winter Park, FL 32792
On Market For 58 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1821

  • Year Built

    1963

  • $/SqFt

    $263

Winter Park Estates - Homes in this prestigious community sell fast—schedule your showing today before it’s gone! KELLER WILLIAMS CLASSIC.

Pended $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 53 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.

Pended $485,000

Reduced By $30,000

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 59 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1672

  • Year Built

    1956

  • $/SqFt

    $290

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

Pended $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 61 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 $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 60 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 56 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 $438,500

Reduced By $500

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 61 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1998

  • Year Built

    1967

  • $/SqFt

    $219

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

Home For Sale $415,000

Reduced By $10,000

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 29 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 49 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1598

  • Year Built

    1990

  • $/SqFt

    $260

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 $399,900

Reduced By $50,000

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 61 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1788

  • Year Built

    1989

  • $/SqFt

    $224

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 $529,900

Reduced By $20,000

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 63 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1953

  • Year Built

    1968

  • $/SqFt

    $271

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

Home For Sale $1,645,000

Reduced By $605,000

Lounge chairs and outdoor umbrella on deck with lake and dock views at 7841 Georgeann St, Winter Park, FL 32792
View Details 63 Photos
Gated driveway leads to an elegant home surrounded by mature landscaping at 7841 Georgeann St, Winter Park, FL 32792
Long, gated brick driveway leading to a modern two-story home with mature trees and manicured landscaping at 7841 Georgeann St, Winter Park, FL 32792
Lush landscaping and a circular driveway complement the modern exterior of this two-story home with a grey brick driveway at 7841 Georgeann St, Winter Park, FL 32792
On Market For 48 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4000

  • Year Built

    1977

  • $/SqFt

    $411

Lakefront luxury meets privacy and convenience—schedule your private tour today! SPECTRUM GLOBAL REALTY, INC.

Home For Sale $1,395,000

Reduced By $255,000

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 63 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2841

  • Year Built

    1953

  • $/SqFt

    $491

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 $478,700

Reduced By $17,000

Charming single-story home featuring stone accents, a well-manicured lawn, and mature landscaping at 1776 E Cheryl Dr, Winter Park, FL 32792
View Details 14 Photos
View of the home featuring stone accents and a long driveway leading to a two-car garage at 1776 E Cheryl Dr, Winter Park, FL 32792
Bright living room featuring a wooden fireplace, hardwood floors, and lots of natural light at 1776 E Cheryl Dr, Winter Park, FL 32792
Modern kitchen with white cabinets, stainless steel appliances, and a view to the pool at 1776 E Cheryl Dr, Winter Park, FL 32792
On Market For 63 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2014

  • Year Built

    1982

  • $/SqFt

    $238

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

Home For Sale $3,195,000

Reduced By $205,000

Charming traditional home with a manicured lawn, mature trees, and a welcoming front porch with columns at 1911 Stonehurst Rd, Winter Park, FL 32789
View Details 37 Photos
Charming brick home featuring a welcoming front porch with classic columns and a beautifully landscaped front yard at 1911 Stonehurst Rd, Winter Park, FL 32789
Expansive backyard showcasing the pool, patio, and meticulously maintained landscaping of the estate at 1911 Stonehurst Rd, Winter Park, FL 32789
An aerial view of a backyard with a pool, patio, fountain, and beautiful landscaping and mature trees at 1911 Stonehurst Rd, Winter Park, FL 32789
On Market For 39 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    5097

  • Year Built

    2001

  • $/SqFt

    $627

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

Pended $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 62 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 31 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 65 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 66 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 $2,795,000

Reduced By $100,000

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 69 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    4912

  • Year Built

    2003

  • $/SqFt

    $569

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

Home For Sale $1,299,000

Reduced By $96,000

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 68 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3140

  • Year Built

    2018

  • $/SqFt

    $414

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 68 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 $834,900

Reduced By $14,100

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 51 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2563

  • Year Built

    2020

  • $/SqFt

    $326

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

Pended $565,000

Reduced By $60,000

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 66 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2309

  • Year Built

    1963

  • $/SqFt

    $245

Enjoy mature, green trees, sidewalks for biking and walking in this charming and sought-after neighborhood. KELLY PRICE & COMPANY 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 69 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 $739,000

Reduced By $11,000

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 69 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2046

  • Year Built

    1964

  • $/SqFt

    $361

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

Pended $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 60 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 $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 10 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 $395,000

Reduced By $15,000

Charming single-story home with a well-manicured lawn and a freshly painted exterior at sunset at 1021 Mare Bello Dr, Winter Park, FL 32792
View Details 37 Photos
Bright and airy living room with large windows, modern furniture, and a neutral color palette at 1021 Mare Bello Dr, Winter Park, FL 32792
Spacious living room featuring hardwood floors, large windows and an ornate chandelier 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 69 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1730

  • Year Built

    1965

  • $/SqFt

    $228

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 $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 59 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.

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 38 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 70 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.

Pended $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 70 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    3121

  • Year Built

    1984

  • $/SqFt

    $351

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

Home For Sale $825,000

Reduced By $70,000

Charming single-story home nestled among mature trees, perfect for peaceful living at 2418 Whitehall Cir, Winter Park, FL 32792
View Details 36 Photos
Inviting single-story home featuring a well-manicured lawn and classic curb appeal at 2418 Whitehall Cir, Winter Park, FL 32792
Modern kitchen features white cabinetry, stainless steel appliances, and a dark island with quartz countertop and pendant lighting at 2418 Whitehall Cir, Winter Park, FL 32792
Bright kitchen showcasing white cabinets, a stainless steel refrigerator, and an island with a quartz countertop and stylish light fixture at 2418 Whitehall Cir, Winter Park, FL 32792
On Market For 70 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2134

  • Year Built

    1962

  • $/SqFt

    $387

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

Pended $735,000

Reduced By $50,000

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 70 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1867

  • Year Built

    1979

  • $/SqFt

    $394

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

Pended $1,800,000

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 73 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2950

  • Year Built

    2025

  • $/SqFt

    $610

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 73 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 $1,299,000

Reduced By $76,000

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
*POTENTIAL GREAT VALUE
On Market For 76 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3204

  • Year Built

    1925

  • $/SqFt

    $405

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

Home For Sale $564,000

Reduced By $5,000

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 76 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2733

  • Year Built

    1979

  • $/SqFt

    $206

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.

Home For Sale $559,500

Reduced By $20,000

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 76 Days

  • Bedrooms

    5

  • Full Bath(s)

    2

  • Sq. Ft.

    2272

  • Year Built

    1956

  • $/SqFt

    $246

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

Pended $389,900

Reduced By $20,099

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 74 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1236

  • Year Built

    1963

  • $/SqFt

    $315

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

Home For Sale $4,395,000

Reduced By $480,000

Modern two-story home with manicured lawn and beautiful landscaping at twilight at 229 Alexander Pl, Winter Park, FL 32789
View Details 64 Photos
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
Open-concept living room with access to an outdoor lounge and a view of the pool area and modern tile flooring at 229 Alexander Pl, Winter Park, FL 32789
On Market For 78 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4431

  • Year Built

    2012

  • $/SqFt

    $992

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 $699,000

Reduced By $50,000

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 79 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2446

  • Year Built

    1979

  • $/SqFt

    $286

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.

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