274 Results

View 274 Winter Park Florida Homes for Sale

Pended $599,900

Reduced By $50,100

Modern two-story house with gray siding, paver driveway, and landscaped lawn at 1875 Staunton Ave, Winter Park, FL 32789
Modern two-story house with gray siding, paver driveway, and landscaped lawn at 1875 Staunton Ave, Winter Park, FL 32789
Inviting front entrance with gray siding, paver walkway, and potted plants at 1875 Staunton Ave, Winter Park, FL 32789
On Market For 58 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2036

  • Year Built

    1954

  • $/SqFt

    $295

Karolina On Killarney - You are less than 2 miles from Park Avenue. THE AGENCY ORLANDO.

Pended $579,000

Reduced By $10,000

Relaxing backyard oasis featuring a refreshing pool with patio furniture at 1424 Cavendish Rd, Winter Park, FL 32789
Charming bungalow with lush landscaping, driveway, and a green exterior at 1424 Cavendish Rd, Winter Park, FL 32789
House exterior with a green facade, black garage door, and manicured lawn at 1424 Cavendish Rd, Winter Park, FL 32789
On Market For 59 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1132

  • Year Built

    1949

  • $/SqFt

    $511

Don’t miss the opportunity to make this Gem your new home! KEYSEEKERS REAL ESTATE.

Pended $414,000

Reduced By $17,000

Bright living room with hardwood floors, comfy seating, and modern decor at 2111 Staunton Ave, Winter Park, FL 32789
Spacious living area showcasing hardwood floors and ample natural light at 2111 Staunton Ave, Winter Park, FL 32789
Spacious bedroom with light walls, hardwood floors, and built-in storage at 2111 Staunton Ave, Winter Park, FL 32789
On Market For 59 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1292

  • Year Built

    1954

  • $/SqFt

    $320

This property is a true gem, offering comfort and sophistication. OPENDOOR BROKERAGE LLC.

Pended $379,000

Reduced By $6,000

Newly renovated home with white exterior, brown garage door, and landscaped yard at 1562 Lawndale Cir, Winter Park, FL 32792
Newly renovated home with white exterior, brown garage door, and landscaped yard at 1562 Lawndale Cir, Winter Park, FL 32792
Newly renovated home with white exterior, brown accents, and landscaped yard at 1562 Lawndale Cir, Winter Park, FL 32792
On Market For 60 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1118

  • Year Built

    1986

  • $/SqFt

    $339

Country Lane - AC and appliances all new in 2024! TERZA REAL ESTATE.

Home For Sale $1,599,900

Home with a pool, outdoor kitchen, and relaxing lounge area at 1417 Miller Ave, Winter Park, FL 32789
Ground floor plan showcasing an open layout with a large living room and kitchen at 1417 Miller Ave, Winter Park, FL 32789
Second floor plan featuring three bedrooms, two bathrooms and a loft at 1417 Miller Ave, Winter Park, FL 32789
On Market For 60 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3312

  • Year Built

    2025

  • $/SqFt

    $483

No HOA fees and just moments from Publix, Trader Joe’s, Park Avenue, Mills/50, the Science Center, Winter Park Events Center, Advent Health and a fantastic array of restaurants and coffee shops. CORCORAN PREMIER REALTY.

Home For Sale $639,999

Reduced By $10,001

Modern kitchen with white cabinets, stainless steel appliances, and quartz countertops at 1401 Lone Feather Trl, Winter Park, FL 32792
Open concept kitchen boasts white cabinets, stainless steel appliances, and an island at 1401 Lone Feather Trl, Winter Park, FL 32792
Private backyard with a spacious patio and lush green lawn at 1401 Lone Feather Trl, Winter Park, FL 32792
On Market For 60 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1770

  • Year Built

    2022

  • $/SqFt

    $362

Convenience is at your doorstep with Park Maitland Preschool, Kelly’s Ice Cream and Foxtail Coffee right at the neighborhood’s entrance. PREMIER SOTHEBY'S INTL. REALTY.

Pended $610,000

Reduced By $39,000

Modern house exterior featuring a white facade, black accents, and a landscaped front yard at 631 Callahan St, Winter Park, FL 32789
Updated home with modern exterior and beautiful landscaping at 631 Callahan St, Winter Park, FL 32789
Charming house exterior with a lush green lawn and beautiful landscaping at 631 Callahan St, Winter Park, FL 32789
On Market For 60 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1751

  • Year Built

    1950

  • $/SqFt

    $348

Carver Town - Come see it for yourself – this is luxury living at its finest. CORCORAN PREMIER REALTY.

Home For Sale $599,900

Reduced By $49,100

House with pool and large lot, desirable location at 2100 Suffield Dr, Winter Park, FL 32792
Inviting rectangular pool with patio and tropical landscaping at 2100 Suffield Dr, Winter Park, FL 32792
Spacious living room with brick fireplace and comfortable seating at 2100 Suffield Dr, Winter Park, FL 32792
On Market For 61 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1807

  • Year Built

    1960

  • $/SqFt

    $332

Don't miss this chance to make this "Great Bones" home your own! RE/MAX 200 REALTY.

Home For Sale $549,900

Reduced By $39,100

Brick ranch house with attached garage and landscaped lawn at 2855 Cady Way, Winter Park, FL 32792
One-story home with gray siding, landscaping, and a curved driveway at 2855 Cady Way, Winter Park, FL 32792
Modern kitchen with stainless steel appliances, granite counters, and white cabinets at 2855 Cady Way, Winter Park, FL 32792
On Market For 62 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1736

  • Year Built

    1964

  • $/SqFt

    $317

Call today to schedule your showing! GLOBAL PROPERTIES SALES & MGMT.

Home For Sale $425,000

Bright living room with fireplace,tile flooring and view to kitchen and backyard at 1309 Paradise Ln, Winter Park, FL 32792
Spacious living room with tiled floors and neutral color palette at 1309 Paradise Ln, Winter Park, FL 32792
Spacious living room with tiled floors and neutral color palette at 1309 Paradise Ln, Winter Park, FL 32792
On Market For 62 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1606

  • Year Built

    1984

  • $/SqFt

    $265

Conveniently located, this home offers easy access to nearby shopping, dining and major roadways and is in the A Rated Lake Howell High school zone. COLDWELL BANKER REALTY.

Home For Sale $4,500,000

Brick home with herringbone driveway, landscaping, and a two-car garage at 702 Via Bella, Winter Park, FL 32789
Two-story home with a two-car garage and landscaped yard, showcasing a beautiful brick exterior at 702 Via Bella, Winter Park, FL 32789
Two-story brick home with dark brown accents, landscaping, and a two-car garage at 702 Via Bella, Winter Park, FL 32789
On Market For 62 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3720

  • Year Built

    2025

  • $/SqFt

    $1,210

The perfect home for those seeking luxurious living and refined elegance. FLORIDIAN REALTY GROUP LLC.

Pended $769,000

Reduced By $30,000

Two-story gray house with black shutters, nicely landscaped front yard at 1375 Suffolk Rd, Winter Park, FL 32789
Two-story gray house with black shutters, landscaped yard, at dusk at 1375 Suffolk Rd, Winter Park, FL 32789
Two-story gray house with black shutters, landscaped yard, and driveway at 1375 Suffolk Rd, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 45 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2548

  • Year Built

    1940

  • $/SqFt

    $302

Don’t miss your chance to see it - schedule your showing today! MAINFRAME REAL ESTATE.

Pended $1,190,000

Reduced By $60,000

Two-story home with a wrap-around porch, and manicured hedges at 567 Osceola Ave, Winter Park, FL 32789
Two-story house with a wrap-around porch and brick driveway at 567 Osceola Ave, Winter Park, FL 32789
Two-story house with a wrap-around porch and brick driveway at 567 Osceola Ave, Winter Park, FL 32789
On Market For 60 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2651

  • Year Built

    1912

  • $/SqFt

    $449

Osceola Court - Parking is easy with a circular driveway, carport and a 2-car garage with plenty of storage. Call today for an appointment! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $429,900

Reduced By $10,000

Landscaped one story house with gray siding, attached garage, and spacious yard at 5405 Justine Way, Winter Park, FL 32792
Bright living room featuring hardwood floors and neutral walls at 5405 Justine Way, Winter Park, FL 32792
Spacious living area with hardwood floors and access to kitchen and backyard at 5405 Justine Way, Winter Park, FL 32792
On Market For 63 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1247

  • Year Built

    1981

  • $/SqFt

    $345

Wrenwood Heights - Don’t just take my word for it – come see how your life fits perfectly into this Winter Park wonder. TBRO REALTY LLC.

Pended $385,000

Reduced By $15,000

Inviting front entrance with a white door, and sidelights, a welcoming poinsettia plant at 5102 Lake Howell Rd, Winter Park, FL 32792
Open living room with tile floors, partial kitchen view, and access to backyard at 5102 Lake Howell Rd, Winter Park, FL 32792
Living room with tile floors, kitchen view, and access to backyard at 5102 Lake Howell Rd, Winter Park, FL 32792
On Market For 62 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1452

  • Year Built

    1957

  • $/SqFt

    $265

Tanglewood - You will want to call this one home. COLDWELL BANKER REALTY.

Home For Sale $995,000

Reduced By $185,000

Two-story house with a blue metal roof and attached garage at 1975 Biscayne Dr, Winter Park, FL 32789
Open concept living room and kitchen with white sofas and modern decor at 1975 Biscayne Dr, Winter Park, FL 32789
Living room features a white sectional sofa, fireplace, and Christmas tree at 1975 Biscayne Dr, Winter Park, FL 32789
On Market For 62 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3270

  • Year Built

    2020

  • $/SqFt

    $304

Karolina On Killarney - Don’t miss your chance to own this property! SOGO REAL ESTATE SERVICES LLC.

Home For Sale $680,000

Reduced By $19,000

Inviting front porch with colorful seating and patterned tile at 1792 Killarney Dr, Winter Park, FL 32789
Spacious living room featuring a fireplace and mid-century modern furniture at 1792 Killarney Dr, Winter Park, FL 32789
Bright living room with a green sofa and hardwood floors at 1792 Killarney Dr, Winter Park, FL 32789
On Market For 64 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2082

  • Year Built

    1958

  • $/SqFt

    $327

Additionally, it is less than 1 mile to Trader Joe's and 1.5 miles to Park Ave. Don't miss out on this exceptional opportunity to own a piece of Winter Park paradise. THE AGENCY ORLANDO.

Pended $675,000

Reduced By $24,000

Aerial view showcases a remodeled home with a golf course view, and a large backyard at 1037 Fairway Dr, Winter Park, FL 32792
Newly remodeled home features a clean, modern exterior and a spacious driveway at 1037 Fairway Dr, Winter Park, FL 32792
Attractive home is situated on a golf course and features a large backyard at 1037 Fairway Dr, Winter Park, FL 32792
On Market For 65 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2145

  • Year Built

    1978

  • $/SqFt

    $315

This home offers the perfect combination of style, functionality, and comfort – a true gem on Winter Golfside Community! LEGACY REALTY & BROKERS LLC.

Home For Sale $900,000

Reduced By $39,900

Two-story house with a two-car garage and paved driveway at 675 Overspin Dr, Winter Park, FL 32789
Front entrance with arched entryway and walkway at 675 Overspin Dr, Winter Park, FL 32789
Spacious kitchen with island, stainless steel appliances, and wood cabinets at 675 Overspin Dr, Winter Park, FL 32789
On Market For 66 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2962

  • Year Built

    2010

  • $/SqFt

    $304

Dubsdread Heights - For golf enthusiasts, the prestigious Dubsdread golf course is located within a mile. COLDWELL BANKER RESIDENTIAL RE.

Pended $587,000

Reduced By $38,000

Charming single story home with a manicured lawn, beautiful trees, a 2-car garage, and freshly painted brick at 7884 Broken Arrow Trl, Winter Park, FL 32792
View of the front porch with a unique painted brick facade, decorative plants, and newly tiled patio at 7884 Broken Arrow Trl, Winter Park, FL 32792
Inviting foyer leading to the dining and living areas with updated flooring and decorative lighting at 7884 Broken Arrow Trl, Winter Park, FL 32792
On Market For 64 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1906

  • Year Built

    1972

  • $/SqFt

    $308

Arrowhead Cove - Reach out with any questions and to schedule a private tour! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $535,000

Reduced By $14,000

Spacious living room with parquet floors and comfy seating at 525 S Lakemont Ave, Winter Park, FL 32792
Open living room showcasing hardwood floors and access to kitchen at 525 S Lakemont Ave, Winter Park, FL 32792
Cozy living room with hardwood floors and a view into the kitchen at 525 S Lakemont Ave, Winter Park, FL 32792
On Market For 67 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1520

  • Year Built

    1955

  • $/SqFt

    $352

Kenilworth Shores - Take advantage of this great opportunity to make it your very own today! MARK SPAIN REAL ESTATE.

Home For Sale $697,000

Reduced By $18,000

Updated kitchen featuring wood cabinets, stainless steel appliances, and quartz countertops at 958 Dunraven Dr, Winter Park, FL 32792
Updated kitchen with stainless steel appliances and wood cabinets at 958 Dunraven Dr, Winter Park, FL 32792
Bright kitchen boasts modern appliances and ample cabinet space at 958 Dunraven Dr, Winter Park, FL 32792
On Market For 67 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1835

  • Year Built

    1957

  • $/SqFt

    $380

Kenilworth Shores - All of this and Much, Much More! WELCOME HOME !! ! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $499,900

Reduced By $5,000

Inviting front entry with stone pillars and a double door at 1710 Aster Dr, Winter Park, FL 32792
Bright entryway with hardwood floors and a console table at 1710 Aster Dr, Winter Park, FL 32792
Spacious living room featuring a stone fireplace and hardwood floors at 1710 Aster Dr, Winter Park, FL 32792
On Market For 67 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1664

  • Year Built

    1979

  • $/SqFt

    $300

Garden Lake Estates - Highly desirable area with easy access to shopping & main roads. FOLIO REALTY LLC.

Pended $449,000

Bright dining room featuring wood table and chairs, view to living room at 2007 Natalen Rd, Winter Park, FL 32792
Efficient kitchen with white cabinetry, built-in desk, and window at 2007 Natalen Rd, Winter Park, FL 32792
White kitchen with appliances, orange tile backsplash, and ample counter space at 2007 Natalen Rd, Winter Park, FL 32792
On Market For 66 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1760

  • Year Built

    1957

  • $/SqFt

    $255

Kenilworth Shores - With its spacious layout, sought-after location, and a generous 9,723-square-foot lot, this home is ready for your personal touch to make it your own. EXP REALTY LLC.

Home For Sale $592,500

Reduced By $7,400

Shows a spacious layout with multiple bedrooms and living areas at 1116 Fairway Dr, Winter Park, FL 32792
Single-story house with attached garage and landscaping at 1116 Fairway Dr, Winter Park, FL 32792
Single-story house with attached garage and landscaping at 1116 Fairway Dr, Winter Park, FL 32792
On Market For 70 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1738

  • Year Built

    1978

  • $/SqFt

    $341

You will surely LOVE to call this place your home! TURN-KEY MOVES REALTY.

Home For Sale $475,000

Reduced By $10,000

Home entryway with dark gray door and terracotta tile floor at 1354 Tierra Cir, Winter Park, FL 32792
Living room with hardwood floors, a large TV, and comfortable seating at 1354 Tierra Cir, Winter Park, FL 32792
Living room with hardwood floors, a large TV, and comfortable seating at 1354 Tierra Cir, Winter Park, FL 32792
On Market For 70 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1969

  • $/SqFt

    $260

Schedule your showing today and make this beautiful home yours! REAL ESTATE FIRM OF ORLANDO.

Home For Sale $499,900

Reduced By $25,100

House with a large backyard, a pond, and surrounding houses visible in the distance at 2073 Shadyhill Ter, Winter Park, FL 32792
Single-story house with a white garage door and landscaping. It has a yellow exterior with a gray roof at 2073 Shadyhill Ter, Winter Park, FL 32792
Single-story house with a white garage door, lush landscaping, and a brick walkway at 2073 Shadyhill Ter, Winter Park, FL 32792
On Market For 72 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1647

  • Year Built

    1988

  • $/SqFt

    $304

This is your opportunity to own your dream home that includes tranquility along with convenience, while offering access to top-rated Seminole County schools, and perfectly located near plenty of dining and shopping options. KROLL REALTY GROUP.

Home For Sale $11,900,000

Elegant home at sunset, gated entrance, palm trees at 1120 Preserve Point Dr, Winter Park, FL 32789
Stunning home with gated entry and manicured landscaping at 1120 Preserve Point Dr, Winter Park, FL 32789
Beautiful home with gated entry and manicured landscaping at 1120 Preserve Point Dr, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 74 Days
  • Bedrooms

    7

  • Full Bath(s)

    9

  • Sq. Ft.

    11255

  • Year Built

    2009

  • $/SqFt

    $1,057

With its own private gated entrance, this home is a one-of-a-kind opportunity to enjoy all of the amenities that Winter Park and Windsong have to offer. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,295,000

Reduced By $100,000

Spacious kitchen featuring a large island and stainless steel appliances at 433 Carolina Ave, Winter Park, FL 32789
Bright kitchen with white cabinets, quartz countertops, and a farmhouse sink at 433 Carolina Ave, Winter Park, FL 32789
Open concept kitchen with island seating and dark hardwood floors at 433 Carolina Ave, Winter Park, FL 32789
On Market For 74 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2700

  • Year Built

    2018

  • $/SqFt

    $480

Come and visit us. Welcome Home! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $1,275,000

Reduced By $20,000

Charming house exterior with mature trees and a brick driveway at 1611 Walnut Ave, Winter Park, FL 32789
White house exterior with lush landscaping and a stone pathway at 1611 Walnut Ave, Winter Park, FL 32789
Spacious living room featuring high ceilings, large windows, and comfortable seating at 1611 Walnut Ave, Winter Park, FL 32789
On Market For 74 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2635

  • Year Built

    1951

  • $/SqFt

    $484

Lake Knowles Terrace - Come see what could be Your next home! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $799,000

Reduced By $50,000

Updated mid-century home with red front door and paver driveway at 744 London Rd, Winter Park, FL 32792
Bright red front door entry with paver walkway at 744 London Rd, Winter Park, FL 32792
Bright foyer with white tile floors, glass-paneled front door, and mirrors creates a welcoming entrance at 744 London Rd, Winter Park, FL 32792
On Market For 74 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2804

  • Year Built

    1968

  • $/SqFt

    $285

Winter Park Pines - Don’t miss the opportunity to make it yours! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $749,900

Two-story light blue house with gray accents, a fenced yard, and a brick walkway at 1521 Harmon Ave, Winter Park, FL 32789
Two-story light blue house with gray accents, a fenced yard, and a brick walkway at 1521 Harmon Ave, Winter Park, FL 32789
Spacious living room with hardwood floors, a large sectional sofa, and a wooden staircase at 1521 Harmon Ave, Winter Park, FL 32789
On Market For 73 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2302

  • Year Built

    2008

  • $/SqFt

    $326

Lawndale - This exceptional home combines style, functionality, and location in one perfect package! ALL REAL ESTATE & INVESTMENTS.

Pended $575,000

Reduced By $25,000

Bright entryway with built-in shelving and home office at 513 Cornwall Rd, Winter Park, FL 32792
Living room featuring a brick accent wall and stylish furniture at 513 Cornwall Rd, Winter Park, FL 32792
Living room with built-in shelving and comfortable seating at 513 Cornwall Rd, Winter Park, FL 32792
On Market For 74 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1735

  • Year Built

    1965

  • $/SqFt

    $331

The optional $60 per year ensures the upkeep of the community signage and common area landscaping, the distribution of the bi-monthly "Needles from the Pines" newsletter, special neighborhood events, and more. BHHS FLORIDA REALTY.

Pended $365,000

Tan single-story house with a yard and palm tree at 770 Carver St, Winter Park, FL 32789
Tan single story house with a walkway and palm tree at 770 Carver St, Winter Park, FL 32789
Tan single-story house with a yard at 770 Carver St, Winter Park, FL 32789
On Market For 13 Days
  • Bedrooms

    4

  • Full Bath(s)

    1

  • Sq. Ft.

    1248

  • Year Built

    1954

  • $/SqFt

    $292

Schedule your private showing today and make your home dreams a reality! LEGENDS REALTY.

Pended $400,000

Bright living room featuring hardwood floors and built-in shelving at 7276 Abbey Ln, Winter Park, FL 32792
Living room with hardwood floors, red accent wall, and comfy seating at 7276 Abbey Ln, Winter Park, FL 32792
Living room, hardwood floors, and view into dining area and kitchen at 7276 Abbey Ln, Winter Park, FL 32792
On Market For 62 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1321

  • Year Built

    1984

  • $/SqFt

    $303

With no HOA, you’ll enjoy the freedom to make this property truly your own. Schedule a private tour today! KELLER WILLIAMS ADVANTAGE REAL.

Pended $359,000

Inviting front porch with blue chairs and a black door at 992 Carnation Dr, Winter Park, FL 32792
Light and airy living room with wood-look floors and ceiling fan at 992 Carnation Dr, Winter Park, FL 32792
Living room with wood-look floors, and a view into the kitchen at 992 Carnation Dr, Winter Park, FL 32792
On Market For 62 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1000

  • Year Built

    1959

  • $/SqFt

    $359

Eastbrook - Don't miss out on this exceptional opportunity to own a piece of Winter Park paradise! RE/MAX ASSURED.

Home For Sale $5,999,999

Reduced By $250,001

Elegant Spanish-style home with a brick driveway and beautifully lit at night at 541 Virginia Dr, Winter Park, FL 32789
Stunning Spanish-style home with a brick driveway and lush landscaping at 541 Virginia Dr, Winter Park, FL 32789
Beautiful Spanish-style home with a large tree and brick driveway at 541 Virginia Dr, Winter Park, FL 32789
On Market For 77 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4725

  • Year Built

    2008

  • $/SqFt

    $1,270

Experience luxury living at its finest with unparalleled lakefront views, exceptional amenities and convenience to all the restaurants and shopping that Winter Park has to offer. HOMEVEST REALTY.

Home For Sale $435,000

Reduced By $30,000

Bright living room with tile floors and an open floor plan at 1860 Gladiolas Dr, Winter Park, FL 32792
Spacious living area featuring neutral walls and tile flooring at 1860 Gladiolas Dr, Winter Park, FL 32792
Cozy dining area with tile floors and a chandelier at 1860 Gladiolas Dr, Winter Park, FL 32792
On Market For 77 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1653

  • Year Built

    1983

  • $/SqFt

    $263

Garden Lake Estates - Thoughtfully designed for comfort, privacy, and style, this home is an ideal retreat for families or those who love to entertain. WEICHERT REALTORS HALLMARK PRO.

Home For Sale $1,070,000

Reduced By $30,000

White brick home with a wood front porch and a charming bench at 2330 Westminster Ct, Winter Park, FL 32789
Relaxing front porch with wooden rocking chairs and brick steps at 2330 Westminster Ct, Winter Park, FL 32789
Wood front door accented with lanterns and a brick walkway at 2330 Westminster Ct, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 79 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3296

  • Year Built

    1928

  • $/SqFt

    $325

Glencoe - Schedule your private showing today and experience the charm of Winter Park living! COMPASS FLORIDA LLC.

Home For Sale $520,000

Reduced By $15,000

Ranch-style home with attached garage and well-manicured lawn at 1422 Tierra Cir, Winter Park, FL 32792
Bright living room showcasing a comfortable sectional sofa and stylish decor at 1422 Tierra Cir, Winter Park, FL 32792
Spacious living area with sectional sofa, TV, and access to the bathroom at 1422 Tierra Cir, Winter Park, FL 32792
On Market For 81 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1968

  • $/SqFt

    $285

Come take a tour of this immaculate pool home today! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $365,000

Reduced By $60,000

Charming one-story home with a spacious front yard at 1397 Hyde Park Dr, Winter Park, FL 32792
Brick home with a white garage door and neat landscaping at 1397 Hyde Park Dr, Winter Park, FL 32792
Large backyard with a white fence and grassy area at 1397 Hyde Park Dr, Winter Park, FL 32792
On Market For 82 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1518

  • Year Built

    1987

  • $/SqFt

    $240

Take advantage of Seminole county schools and convenient location, making this property an enticing opportunity. REALTY HUB.

Home For Sale $615,000

Reduced By $15,000

Modern two-story house under construction, seen from an aerial perspective at 5255 Seminole Ave, Winter Park, FL 32792
New construction home, aerial view showing the roofline and backyard at 5255 Seminole Ave, Winter Park, FL 32792
High-angle view of a new house under construction in a wooded area at 5255 Seminole Ave, Winter Park, FL 32792
On Market For 83 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2170

  • Year Built

    1957

  • $/SqFt

    $283

Don’t wait—schedule your showing today and take the first step toward living in your dream home! COLDWELL BANKER RESIDENTIAL RE.

Pended $668,900

Reduced By $56,100

White ranch house with circular driveway, landscaped lawn, and attached garage at 1860 Linden Rd, Winter Park, FL 32792
Charming ranch home with a spacious lawn and palm trees at 1860 Linden Rd, Winter Park, FL 32792
White brick ranch house with a long driveway and lush green lawn at 1860 Linden Rd, Winter Park, FL 32792
On Market For 81 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1820

  • Year Built

    1957

  • $/SqFt

    $368

Tanglewood - This PRIME LOCATION is close to all of the amazing shopping and dining that Downtown Orlando and Winter Park offer. Schedule your showing soon! COMPASS FLORIDA LLC.

Home For Sale $400,000

Reduced By $25,000

Front porch entry with a unique swing and landscaping at 2827 Euston Rd, Winter Park, FL 32789
Bright and airy living room with hardwood floors and neutral decor at 2827 Euston Rd, Winter Park, FL 32789
Open concept living room featuring hardwood floors and ample natural light at 2827 Euston Rd, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 84 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1568

  • Year Built

    1956

  • $/SqFt

    $255

Fairbanks Shores - Conveniently located just minutes from I-4, this home offers easy access to downtown Orlando, nearby attractions, and top-rated schools. Schedule your private showing today! REGENCY REAL ESTATE LLC.

Home For Sale $345,000

Reduced By $5,000

Newly painted house exterior with well-maintained lawn at 2762 Hilda Cv, Winter Park, FL 32792
Spacious bonus room with tile floors and ample closet space at 2762 Hilda Cv, Winter Park, FL 32792
Bright bonus room featuring tile flooring and multiple closets at 2762 Hilda Cv, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 84 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1493

  • Year Built

    1981

  • $/SqFt

    $231

Slovak Village - Walking distance to Orlando’s famous Donut King, Kelly’s Homemade Ice Cream, and Foxtail Coffee! Submit your offer today! THE REALTY MEDICS.

Pended $2,300,000

Luxury lakefront home nestled amongst lush trees at 1032 Early Ave, Winter Park, FL 32789
Stone driveway leading to a beautiful home at 1032 Early Ave, Winter Park, FL 32789
Lakefront property with expansive wooded area at 1032 Early Ave, Winter Park, FL 32789
On Market For 61 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2894

  • Year Built

    1999

  • $/SqFt

    $795

Buyers And Their Agents Must Verify All Information That Is Important To Them. KINCAID REALTY.

Home For Sale $895,000

Two-story home with festive lights, two-car garage, and brick paver driveway at 1263 Verdant Glade Pl, Winter Park, FL 32792
Two-story home floor plan displays an open layout with gourmet kitchen option at 1263 Verdant Glade Pl, Winter Park, FL 32792
Two-story home floor plan shows a loft, three bedrooms, and two bathrooms upstairs at 1263 Verdant Glade Pl, Winter Park, FL 32792
On Market For 92 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2589

  • Year Built

    2020

  • $/SqFt

    $346

Meadows At Hawks Crest - 20 foot ceilings, tile roof, too much to describe. Pics to follow FLAT FEE MLS REALTY.

Home For Sale $485,000

Reduced By $40,000

Spacious living room with blue velvet couch and built-in bookcase at 1608 Bomi Cir, Winter Park, FL 32792
Bright living room with blue couch, Christmas tree, and view to backyard at 1608 Bomi Cir, Winter Park, FL 32792
Quaint dining room with wooden table and chairs, and view to kitchen at 1608 Bomi Cir, Winter Park, FL 32792
On Market For 93 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1807

  • Year Built

    1983

  • $/SqFt

    $268

Tamarak - Call to schedule your private showing today! KELLER WILLIAMS ADVANTAGE III REALTY.

Home For Sale $449,990

Reduced By $10,000

Quaint light blue house with a white porch and lush green lawn at 1550 Indiana Ave, Winter Park, FL 32789
Relaxing front porch with rocking chairs and a porch swing at 1550 Indiana Ave, Winter Park, FL 32789
Inviting front porch with rocking chairs and a porch swing at 1550 Indiana Ave, Winter Park, FL 32789
On Market For 88 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1032

  • Year Built

    1950

  • $/SqFt

    $436

Lawndale - Perfect as a cozy retreat or an exceptional investment opportunity in a prime location. TALENT REALTY SOLUTIONS.

Home For Sale $2,000,000

Two-story home floor plan showcasing five bedrooms, a large gathering room, and a two-car garage at 2260 Mulbry Dr, Winter Park, FL 32789
First-floor plan with open concept kitchen, gathering room, and two-car garage at 2260 Mulbry Dr, Winter Park, FL 32789
Second floor plan featuring three bedrooms, a loft, and two bathrooms at 2260 Mulbry Dr, Winter Park, FL 32789
On Market For 99 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3246

  • Year Built

    2025

  • $/SqFt

    $616

Lake Forest Park - Zoned for top-rated schools, this is your opportunity to build your dream Oasis and enjoy the Florida lifestyle! KELLER WILLIAMS WINTER PARK.

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Call to Schedule a Showing

(407) 278-2057

(407) 278-2057