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253 Results

View 253 Winter Park Florida Homes for Sale

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
View Details 31 Photos
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 62 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

Ranch style home with a spacious yard and attached garage at 513 Cornwall Rd, Winter Park, FL 32792
View Details 60 Photos
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 63 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 walkway and palm tree at 770 Carver St, Winter Park, FL 32789
View Details 6 Photos
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 35 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

Brick ranch house with attached garage and well-maintained lawn at 7276 Abbey Ln, Winter Park, FL 32792
View Details 46 Photos
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 51 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

Mid-century modern home with landscaped yard, driveway, and updated exterior at 992 Carnation Dr, Winter Park, FL 32792
View Details 39 Photos
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 64 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 $6,100,000

Reduced By $150,000

Spanish style home with brick driveway, lush landscaping, and two-car garage at 541 Virginia Dr, Winter Park, FL 32789
View Details 57 Photos
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 66 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4725

  • Year Built

    2008

  • $/SqFt

    $1,291

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

Updated single-story home with a stone accent and a two-car garage at 1860 Gladiolas Dr, Winter Park, FL 32792
View Details 33 Photos
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 67 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

Charming ranch home with mature landscaping and a two-car garage at 2330 Westminster Ct, Winter Park, FL 32789
View Details 49 Photos
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 67 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.

Pended $875,000

Reduced By $75,000

Single story home with driveway, surrounded by lush trees and other houses at 1655 N Park Ave, Winter Park, FL 32789
View Details 13 Photos
Single-story home with a yard, viewed from above, surrounded by houses and trees at 1655 N Park Ave, Winter Park, FL 32789
Single story home with a large yard, viewed from above at 1655 N Park Ave, Winter Park, FL 32789
Single story home with driveway and yard, aerial view at 1655 N Park Ave, Winter Park, FL 32789
On Market For 68 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1134

  • Year Built

    1955

  • $/SqFt

    $772

Villa View Park - The 14,290 SF lot is zoned for Lakemont Elementary, Maitland Middle and Winter Park High schools in the heart of Winter Park! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $525,000

Reduced By $10,000

Ranch-style home with attached garage and well-manicured lawn at 1422 Tierra Cir, Winter Park, FL 32792
View Details 20 Photos
House exterior showcasing a well-maintained lawn and attached garage 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 70 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1968

  • $/SqFt

    $287

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

Home For Sale $425,000

Brick house with a two-car garage and a well-maintained lawn at 1397 Hyde Park Dr, Winter Park, FL 32792
View Details 25 Photos
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 71 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1518

  • Year Built

    1987

  • $/SqFt

    $280

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

New construction home aerial view, showcasing the modern design and spacious layout at 5255 Seminole Ave, Winter Park, FL 32792
View Details 34 Photos
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 72 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

Ranch style home with a large front yard, driveway, and mature landscaping at 1860 Linden Rd, Winter Park, FL 32792
View Details 47 Photos
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 70 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

Charming house with a spacious front yard and walkway at 2827 Euston Rd, Winter Park, FL 32789
View Details 30 Photos
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 73 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

Updated house exterior boasts a fresh coat of paint and landscaping at 2762 Hilda Cv, Winter Park, FL 32792
View Details 24 Photos
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 73 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 home with pool and lakefront access at 1032 Early Ave, Winter Park, FL 32789
View Details 73 Photos
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 50 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 a light-beige exterior, two-car garage, and landscaped lawn at 1263 Verdant Glade Pl, Winter Park, FL 32792
View Details 9 Photos
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 81 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 $500,000

Reduced By $25,000

Cute ranch home with red door, gray siding, and nicely landscaped yard at 1608 Bomi Cir, Winter Park, FL 32792
View Details 33 Photos
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 83 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1807

  • Year Built

    1983

  • $/SqFt

    $277

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

Home For Sale $449,990

Reduced By $10,000

Charming light blue house with a white porch and landscaped yard at 1550 Indiana Ave, Winter Park, FL 32789
View Details 33 Photos
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 77 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 with modern design, two-car garage, and palm trees at 2260 Mulbry Dr, Winter Park, FL 32789
View Details 4 Photos
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 88 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.

Home For Sale $459,995

Reduced By $10,000

White single-story home with brown roof and garage at 1005 Carvell Dr, Winter Park, FL 32792
View Details 45 Photos
Single-story house with palm tree and well-maintained lawn at 1005 Carvell Dr, Winter Park, FL 32792
Ranch style home with lush green lawn and blue sky at 1005 Carvell Dr, Winter Park, FL 32792
One-story house with a large yard and shed at 1005 Carvell Dr, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 93 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1932

  • Year Built

    1971

  • $/SqFt

    $238

Don’t miss your opportunity to own this incredible home; schedule a showing today and make your dream of Winter Park living a reality! EXP REALTY LLC.

Home For Sale $450,000

Reduced By $15,000

Charming single-story home featuring a well-maintained lawn, mature landscaping, and a long private driveway at 2158 Sussex Rd, Winter Park, FL 32792
View Details 17 Photos
Spacious living room with hardwood floors and large windows at 2158 Sussex Rd, Winter Park, FL 32792
Laundry room with tile floors, shelving, and hookups at 2158 Sussex Rd, Winter Park, FL 32792
Modern kitchen with granite countertops and stainless steel appliances at 2158 Sussex Rd, Winter Park, FL 32792
On Market For 93 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1669

  • Year Built

    1973

  • $/SqFt

    $270

Winter Woods - Convenient to 426/Aloma, 417, 50/Colonial, Park Ave., airport, shopping and restaurants. MUST SEE! KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $4,985,000

Modern two-story home with white exterior, gray accents, and a paved driveway at 2161 Sharon Rd, Winter Park, FL 32789
View Details 90 Photos
Luxury home with gray and white exterior, landscaping, and a spacious driveway at 2161 Sharon Rd, Winter Park, FL 32789
Stunning two-story home, white exterior, lush landscaping, and a large driveway at 2161 Sharon Rd, Winter Park, FL 32789
Modern home with white exterior, gray accents, and a two-car garage at 2161 Sharon Rd, Winter Park, FL 32789
On Market For 94 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6338

  • Year Built

    2023

  • $/SqFt

    $787

Tuscania - Get one step closer to owning the realization of your dream dwelling experience! LA ROSA REALTY HORIZONS LLC.

Home For Sale $1,150,000

Brick ranch home with blue accents and a pink door, landscaped lawn and walkway at 708 Balmoral Rd, Winter Park, FL 32789
View Details 45 Photos
Ranch style home with a walkway leading to the entrance. Features brick exterior and blue accents at 708 Balmoral Rd, Winter Park, FL 32789
Front entrance with pink door and brick steps, blue siding, and landscaping at 708 Balmoral Rd, Winter Park, FL 32789
Bright entryway with tiled floor, a small table, and a view to the hardwood living area at 708 Balmoral Rd, Winter Park, FL 32789
On Market For 96 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2786

  • Year Built

    1960

  • $/SqFt

    $413

Kenilworth Shores - This fantastic location provides easy access to shopping, dining, and the popular Park Avenue with its boutique shopping and great restaurants. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $535,000

Reduced By $27,000

House exterior featuring a light-grey facade, white garage door, and a well-maintained lawn at 4026 Tenita Dr, Winter Park, FL 32792
View Details 33 Photos
Spacious living room with a stone fireplace, tiled floors, and comfortable seating at 4026 Tenita Dr, Winter Park, FL 32792
Living room with a stone fireplace and brown tiled floors at 4026 Tenita Dr, Winter Park, FL 32792
Bright bedroom with large bed, modern nightstands, and ample closet space at 4026 Tenita Dr, Winter Park, FL 32792
On Market For 99 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2122

  • Year Built

    1979

  • $/SqFt

    $252

Lake Waunatta Woods - Don't miss out on this exceptional property. OPENDOOR BROKERAGE LLC.

Home For Sale $399,900

Reduced By $10,000

Newly renovated house with gray exterior, covered porch, and well-manicured lawn at 3607 Datura Ct, Winter Park, FL 32792
View Details 66 Photos
Aerial view showcasing the house's position on a corner lot near a waterway at 3607 Datura Ct, Winter Park, FL 32792
Aerial view showing home's location near water, neighborhood context, and surrounding houses at 3607 Datura Ct, Winter Park, FL 32792
Gray house with a covered porch, freshly mulched landscaping, and a neatly kept lawn at 3607 Datura Ct, Winter Park, FL 32792
On Market For 100 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1600

  • Year Built

    1962

  • $/SqFt

    $250

Eastbrook - Ready for immediate move in. Schedule your showing today! PREMIUM PROPERTIES R.E SERVICE.

Home For Sale $429,900

Reduced By $35,100

Newly renovated home with gray siding, blue door, and red mulch at 1566 Lawndale Cir, Winter Park, FL 32792
View Details 39 Photos
Gray house with blue garage door and red mulch at 1566 Lawndale Cir, Winter Park, FL 32792
House entrance with blue door and red mulch landscaping at 1566 Lawndale Cir, Winter Park, FL 32792
Blue front door with white sidelight and black hardware at 1566 Lawndale Cir, Winter Park, FL 32792
On Market For 101 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1592

  • Year Built

    1985

  • $/SqFt

    $270

Country Lane - Lovely walkable neighborhood with playground, tennis courts and lakefront dock for fishing. TERZA REAL ESTATE.

Home For Sale $2,949,999

Reduced By $50,000

Relaxing deck overlooking lake with fire pit and seating at 2652 Lake Howell Ln, Winter Park, FL 32792
View Details 38 Photos
Aerial view of waterfront property with lush landscaping at 2652 Lake Howell Ln, Winter Park, FL 32792
Two-car garage and boat parking at 2652 Lake Howell Ln, Winter Park, FL 32792
Elegant front entry with columns and brick steps at 2652 Lake Howell Ln, Winter Park, FL 32792
On Market For 104 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3898

  • Year Built

    1954

  • $/SqFt

    $757

Whether you're looking for a vacation getaway or a forever home, this is a rare opportunity you won't want to miss. Schedule your private showing today! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $749,000

Reduced By $50,000

Charming yellow bungalow with screened porch, mature trees, and a landscaped yard at 786 Antonette Ave, Winter Park, FL 32789
View Details 31 Photos
Aerial view showing home's location in a vibrant, tree-lined neighborhood near the water at 786 Antonette Ave, Winter Park, FL 32789
Spacious backyard with lush grass, tropical plants, and a fire pit area at 786 Antonette Ave, Winter Park, FL 32789
Inviting front porch with blue door, wicker furniture, and a tranquil atmosphere at 786 Antonette Ave, Winter Park, FL 32789
On Market For 106 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1146

  • Year Built

    1925

  • $/SqFt

    $654

College Place - Sure to attract a lot of attention (as homes in this area don’t come up for sale often) seize the opportunity to make it your own! RE/MAX 200 REALTY.

Home For Sale $460,000

Reduced By $39,999

Ranch-style home with mature landscaping and driveway at 1621 Puritan Ave, Winter Park, FL 32792
View Details 34 Photos
House exterior with basketball hoop and driveway at 1621 Puritan Ave, Winter Park, FL 32792
Single-story house with large yard and neighborhood view at 1621 Puritan Ave, Winter Park, FL 32792
Home exterior featuring a large yard and basketball court at 1621 Puritan Ave, Winter Park, FL 32792
On Market For 106 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1765

  • Year Built

    1963

  • $/SqFt

    $261

Eastbrook - Don’t miss this opportunity to enjoy peaceful living while staying close to everything in Winter Park. PREFERRED REAL ESTATE BROKERS.

Home For Sale $10,999,999

Modern home with sleek design, light color, and a landscaped lawn at 2661 Via Tuscany, Winter Park, FL 32789
View Details 100 Photos
Grand foyer with wood door, cowhide rug, and view into the living room with high ceilings and natural light at 2661 Via Tuscany, Winter Park, FL 32789
Bright living room with modern decor, floor-to-ceiling windows, and an open layout for seamless entertaining at 2661 Via Tuscany, Winter Park, FL 32789
Modern kitchen featuring an island with seating, sleek cabinetry, and high-end stainless steel appliances at 2661 Via Tuscany, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 107 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4564

  • Year Built

    2024

  • $/SqFt

    $2,410

Don’t miss out on this exceptional opportunity! schedule your private showing today! ! PV LUXURY GROUP PA.

Home For Sale $1,395,000

Reduced By $55,000

Two-story farmhouse style home with white siding, landscaping, and a two-car garage at 777 Halifax Ave, Winter Park, FL 32792
View Details 49 Photos
Two-story farmhouse style home with white siding, landscaping, and a two-car garage at dusk at 777 Halifax Ave, Winter Park, FL 32792
Spacious kitchen with a large island, white cabinets, and modern light fixtures at 777 Halifax Ave, Winter Park, FL 32792
Modern kitchen with white cabinets, a large island, and gold hardware at 777 Halifax Ave, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 112 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3161

  • Year Built

    2021

  • $/SqFt

    $441

Located in the heart of Winter Park, known for its tree-lined streets, excellent schools, and vibrant dining and shopping scene, this home is just minutes from everything the area has to offer. EXP REALTY LLC.

Home For Sale $405,000

Reduced By $35,000

Ranch-style home with a two-car garage and a spacious driveway at 3076 Crane Strand Dr, Winter Park, FL 32792
View Details 37 Photos
Newly renovated home with a large front yard and mature trees at 3076 Crane Strand Dr, Winter Park, FL 32792
Inviting front entry with a brick walkway and charming decor at 3076 Crane Strand Dr, Winter Park, FL 32792
Spacious bedroom with a comfortable bed, a desk, and a TV at 3076 Crane Strand Dr, Winter Park, FL 32792
On Market For 111 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1200

  • Year Built

    1972

  • $/SqFt

    $338

Laurel Springs - Don’t miss this incredible opportunity to enjoy all the perks of Winter Park living in a tranquil and welcoming community. KELLER WILLIAMS LEGACY REALTY.

Home For Sale $2,999,900

Reduced By $299,100

Beautiful two-story home with a lush green lawn at 2550 Venetian Way, Winter Park, FL 32789
View Details 41 Photos
Elegant entryway with high ceilings and wood door at 2550 Venetian Way, Winter Park, FL 32789
Stunning entryway with a unique architectural design at 2550 Venetian Way, Winter Park, FL 32789
Dramatic entryway with a circular staircase and high ceilings at 2550 Venetian Way, Winter Park, FL 32789
On Market For 115 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4875

  • Year Built

    2008

  • $/SqFt

    $615

Maitland Shores - Relaxation and a renewed sense of self await! COMPASS FLORIDA LLC.

Pended $1,775,000

Reduced By $175,000

Two-story house with white walls, gray roof, and a two-car garage at 1781 Goodrich Ave, Winter Park, FL 32789
View Details 49 Photos
Two-story house with white walls, gray roof, and a two-car garage at 1781 Goodrich Ave, Winter Park, FL 32789
Front porch detail of a two-story house at 1781 Goodrich Ave, Winter Park, FL 32789
Side view of two-story house with a three-car garage at 1781 Goodrich Ave, Winter Park, FL 32789
On Market For 94 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2701

  • Year Built

    2024

  • $/SqFt

    $657

Sylvan Heights - Completing this house is a seamless transition from the indoor living space to the outdoor pool and entertainment space. COMPASS FLORIDA LLC.

Home For Sale $1,649,000

Reduced By $50,000

Modern two-story house with stone accents at 1429 Chapman Cir, Winter Park, FL 32789
View Details 36 Photos
Elegant entryway with blue doors and stone pillars at 1429 Chapman Cir, Winter Park, FL 32789
Open living area with stone wall and backyard access at 1429 Chapman Cir, Winter Park, FL 32789
Bright living room with white sofas and large windows at 1429 Chapman Cir, Winter Park, FL 32789
On Market For 118 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3116

  • Year Built

    2014

  • $/SqFt

    $529

This masterfully designed residence offers the perfect balance of sophisticated style, modern convenience, and prime location. CORCORAN PREMIER REALTY.

Home For Sale $1,299,000

Two-story Mediterranean home with tile roof and attached garage at 7440 Aloma Ave, Winter Park, FL 32792
View Details 39 Photos
Luxury two-story home with tile roof and large driveway at 7440 Aloma Ave, Winter Park, FL 32792
Grand living room with ornate furnishings and a sweeping staircase at 7440 Aloma Ave, Winter Park, FL 32792
Elegant living room showcasing a dramatic staircase and high ceilings at 7440 Aloma Ave, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 118 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4435

  • Year Built

    1950

  • $/SqFt

    $293

The possibilities are endless—don’t miss out on this incredible opportunity! MARZUCCO REAL ESTATE.

Home For Sale $815,000

Reduced By $20,000

Two-story house with three-car garage, landscaped yard, and stone accents at 1316 Fountain Hills Ct, Winter Park, FL 32792
View Details 33 Photos
Inviting front entrance with stone columns and a charming welcome sign at 1316 Fountain Hills Ct, Winter Park, FL 32792
Relaxing backyard oasis featuring a refreshing pool and fire pit at 1316 Fountain Hills Ct, Winter Park, FL 32792
Bright and airy entryway with staircase, built-in storage and tile flooring at 1316 Fountain Hills Ct, Winter Park, FL 32792
On Market For 117 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2823

  • Year Built

    2018

  • $/SqFt

    $289

This home is a one of a kind find in Winter Park with its location close to Winter Springs Oviedo, UCF, Orlando downtown, Winter Park shopping, the airport, 417 & major roadways. Schedule a Showing Today! EMPIRE NETWORK REALTY.

Home For Sale $579,900

Reduced By $75,000

Brick ranch house with a two-car garage, landscaping, and a long driveway at 2518 Sweetwater Trl, Winter Park, FL 32789
View Details 41 Photos
Brick ranch home with a two-car garage and a curved driveway at 2518 Sweetwater Trl, Winter Park, FL 32789
Ranch style brick home with a two-car garage and landscaped lawn at 2518 Sweetwater Trl, Winter Park, FL 32789
Brick ranch house with a two-car garage and lush green lawn at 2518 Sweetwater Trl, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 120 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2205

  • Year Built

    1965

  • $/SqFt

    $263

Do not miss out on the perfect blend of style, comfort, and location! BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY.

Home For Sale $500,000

Reduced By $75,000

Charming two-story home with a well-manicured lawn and an American flag waving in the breeze at 5240 N Lake Burkett Ln, Winter Park, FL 32792
View Details 73 Photos
Detailed floorplan showcasing the layout of the home's two floors with room dimensions and major features at 5240 N Lake Burkett Ln, Winter Park, FL 32792
Charming two-story home featuring a well-manicured lawn and a classic design with a two-car garage at 5240 N Lake Burkett Ln, Winter Park, FL 32792
Inviting front yard with lush green grass and a well-maintained exterior featuring a charming entryway and manicured landscaping at 5240 N Lake Burkett Ln, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 80 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2290

  • Year Built

    1987

  • $/SqFt

    $218

Come see all this amazing home has to offer. COLDWELL BANKER REALTY.

Home For Sale $474,900

Reduced By $24,100

Ranch style home with blue exterior and a spacious lawn at 2341 Devon Ct, Winter Park, FL 32789
View Details 27 Photos
Bright living room featuring light wood floors and a ceiling fan at 2341 Devon Ct, Winter Park, FL 32789
Spacious living room with light wood floors, open to kitchen at 2341 Devon Ct, Winter Park, FL 32789
Open concept living room with hardwood floors and a view to kitchen at 2341 Devon Ct, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 121 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1773

  • Year Built

    1953

  • $/SqFt

    $268

Glencoe - Schedule your appointment today to preview this Winter Park jem! UNITED REAL ESTATE PREFERRED.

Home For Sale $4,100,000

Two-story modern home with a black roof and landscaped yard at 1751 Glencoe Rd, Winter Park, FL 32789
View Details 18 Photos
Two-story modern home with a black roof and paver driveway at 1751 Glencoe Rd, Winter Park, FL 32789
Modern two story home with a large pool and deck at 1751 Glencoe Rd, Winter Park, FL 32789
Spacious living room with a fireplace and built-in shelving at 1751 Glencoe Rd, Winter Park, FL 32789
On Market For 125 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4520

  • Year Built

    2025

  • $/SqFt

    $907

Experience the epitome of refined living at 1751 Glencoe Road, where every detail has been crafted to perfection. COMPASS FLORIDA, LLC.

Pended $2,650,000

Reduced By $150,000

Stunning two-story home with brick pathway, lush landscaping, and a Mediterranean-style design at 1010 N Pennsylvania Ave, Winter Park, FL 32789
View Details 88 Photos
Beautiful home at night with a gated entry and walkway leading to the front door at 1010 N Pennsylvania Ave, Winter Park, FL 32789
Elegant home entrance featuring a brick walkway and ornate double doors at 1010 N Pennsylvania Ave, Winter Park, FL 32789
Bright and spacious entryway with tile floors, double doors, and decorative accents at 1010 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 123 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4074

  • Year Built

    2017

  • $/SqFt

    $650

Feel free to request an upgrades and features sheet outlining all the wonderful aspects of this home! BHHS FLORIDA REALTY.

Pended $940,000

Charming single story home with mature landscaping at 2050 Temple Dr, Winter Park, FL 32789
View Details 25 Photos
Landscaped street view of a charming home at 2050 Temple Dr, Winter Park, FL 32789
White house with red tile patio and mature trees at 2050 Temple Dr, Winter Park, FL 32789
Large backyard with a pool and a wooden fence at 2050 Temple Dr, Winter Park, FL 32789
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1449

  • Year Built

    1950

  • $/SqFt

    $649

Builders welcome to walk the lot with notice to owner. LISTING AGENT IS OWNER. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $432,000

Reduced By $16,800

Mid-century modern home with a paved driveway and lush landscaping at 627 Carvell Dr, Winter Park, FL 32792
View Details 21 Photos
Beautiful mid-century modern home with a well-manicured lawn at 627 Carvell Dr, Winter Park, FL 32792
Bright living room featuring light flooring and a sliding barn door at 627 Carvell Dr, Winter Park, FL 32792
Bright and airy living room with a barn door and hardwood floors at 627 Carvell Dr, Winter Park, FL 32792
On Market For 101 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1346

  • Year Built

    1957

  • $/SqFt

    $321

Winter Park Estates - Don’t miss the opportunity to make this exceptional property your own! NO HOA! EXP REALTY LLC.

Home For Sale $439,000

Reduced By $10,000

Two-story house with gray siding and landscaped lawn at 1820 Blaine Ter, Winter Park, FL 32792
View Details 51 Photos
Two-story house with gray siding and attached garage at 1820 Blaine Ter, Winter Park, FL 32792
Two-story house with gray siding, a two-car garage, and a well-manicured lawn at 1820 Blaine Ter, Winter Park, FL 32792
Two-story house with gray siding, a two-car garage, and a landscaped front yard at 1820 Blaine Ter, Winter Park, FL 32792
On Market For 128 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1725

  • Year Built

    1990

  • $/SqFt

    $254

Don't miss your chance to make this exceptional house your home! LPT REALTY.

Home For Sale $869,000

Reduced By $100,000

Charming single story home with a modern white exterior and landscaped lawn at 1795 Walker Ave, Winter Park, FL 32789
View Details 31 Photos
Modern kitchen with white cabinets, quartz countertops, and gold accents at 1795 Walker Ave, Winter Park, FL 32789
Bright dining room with wood table and mustard yellow chairs at 1795 Walker Ave, Winter Park, FL 32789
Modern kitchen with a breakfast bar, white cabinets and gold fixtures at 1795 Walker Ave, Winter Park, FL 32789
On Market For 129 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    1813

  • Year Built

    1958

  • $/SqFt

    $479

Osceola Heights - Don't miss out on this opportunity—act quickly! ALIGN REAL ESTATE LLC.

Home For Sale $699,000

Reduced By $50,999

Aerial view of a home with a pool, solar panels, and well-maintained landscaping at 3136 Heartleaf Pl, Winter Park, FL 32792
View Details 33 Photos
Freeform swimming pool with a screened enclosure at 3136 Heartleaf Pl, Winter Park, FL 32792
Relaxing living room with large TV and hardwood floors at 3136 Heartleaf Pl, Winter Park, FL 32792
Well maintained green two story home with landscaped front yard and matching green driveway at 3136 Heartleaf Pl, Winter Park, FL 32792
On Market For 133 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2717

  • Year Built

    1995

  • $/SqFt

    $257

Lost Creek - Situated on almost a quarter-acre corner lot in a beautiful, well-cared-for neighborhood with Seminole County Schools, this well-maintained home offers easy access to 417, is less than 20 minutes from the famous Park Avenue with some of the best shops and restaurants in the city, and 25 minutes from the airport. Schedule your showing today! ALL REAL ESTATE & INVESTMENTS.

Home For Sale $995,000

Modern home with large deck, wood siding, and expansive windows at 870 Carver St, Winter Park, FL 32789
View Details 6 Photos
Contemporary two-story house with a sleek design and wood accents at 870 Carver St, Winter Park, FL 32789
Contemporary design with wood accents, stone walkway, and lush landscaping at 870 Carver St, Winter Park, FL 32789
Modern home with a large deck, and open floor plan visible through large window at 870 Carver St, Winter Park, FL 32789
On Market For 133 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1844

  • Year Built

    1954

  • $/SqFt

    $540

Don’t miss the chance to partner with a premier builder to create a home that meets your unique needs. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,350,000

Reduced By $100,000

Lakefront property with a dock and gazebo at 632 Country Club Dr, Winter Park, FL 32789
View Details 38 Photos
Ranch-style house with a landscaped yard at 632 Country Club Dr, Winter Park, FL 32789
Aerial view of a waterfront home with a lake view and city skyline in the background at 632 Country Club Dr, Winter Park, FL 32789
Lakefront property with a large wooden dock and gazebo at 632 Country Club Dr, Winter Park, FL 32789
On Market For 138 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2342

  • Year Built

    1952

  • $/SqFt

    $576

632 Country Club is approximately 1.5 miles from luxurious Park Avenue and 5 miles from downtown Orlando. KELLER WILLIAMS ADVANTAGE REALTY.

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