EasyStreet Realty
REALTOR ®
(954) 439-6446
Email Al
mobile navigation links
323 Results

View 323 Winter Park Florida Homes for Sale

Home For Sale $680,000

Reduced By $19,000

Charming one-story home with gray brick, brown trim, a spacious lawn, and mature trees at 1792 Killarney Dr, Winter Park, FL 32789
View Details 42 Photos
View of a one-story home with an attached garage, gray brick, and a concrete driveway at 1792 Killarney Dr, Winter Park, FL 32789
Paver walkway to front door with modern wood siding and beautiful landscaping at 1792 Killarney Dr, Winter Park, FL 32789
Cozy front porch with chairs, decorative tile, and a view of the neighborhood at 1792 Killarney Dr, Winter Park, FL 32789
On Market For 110 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.

Home For Sale $849,900

Reduced By $90,000

Two-story house with a two-car garage and paved driveway at 675 Overspin Dr, Winter Park, FL 32789
View Details 37 Photos
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
*POTENTIAL GREAT VALUE
On Market For 124 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2962

  • Year Built

    2010

  • $/SqFt

    $287

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

Home For Sale $679,000

Reduced By $36,000

Attractive ranch home with circular driveway and mature landscaping at 958 Dunraven Dr, Winter Park, FL 32792
View Details 35 Photos
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 125 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1835

  • Year Built

    1957

  • $/SqFt

    $370

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

Home For Sale $489,900

Reduced By $15,000

Updated single-story home with a stone facade and a two-car garage at 1710 Aster Dr, Winter Park, FL 32792
View Details 30 Photos
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 124 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1664

  • Year Built

    1979

  • $/SqFt

    $294

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

Home For Sale $569,900

Reduced By $30,000

Single-story house with attached garage and landscaping at 1116 Fairway Dr, Winter Park, FL 32792
View Details 34 Photos
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 128 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1738

  • Year Built

    1978

  • $/SqFt

    $328

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

Home For Sale $464,900

Reduced By $20,100

Single-story home with a white garage door and palm trees in the front yard at 1354 Tierra Cir, Winter Park, FL 32792
View Details 31 Photos
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 128 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1969

  • $/SqFt

    $254

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

Home For Sale $11,900,000

Grand two-story home with gated entry and lush landscaping at 1120 Preserve Point Dr, Winter Park, FL 32789
View Details 85 Photos
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 132 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

Modern two-story house with a landscaped lawn and walkway at 433 Carolina Ave, Winter Park, FL 32789
View Details 22 Photos
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 132 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

Inviting front entrance with lush landscaping and double doors at 1611 Walnut Ave, Winter Park, FL 32789
View Details 41 Photos
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 132 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 $5,800,000

Reduced By $450,000

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 135 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4725

  • Year Built

    2008

  • $/SqFt

    $1,228

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 $999,000

Reduced By $101,000

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
On Market For 137 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3296

  • Year Built

    1928

  • $/SqFt

    $303

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

Home For Sale $509,900

Reduced By $25,100

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 138 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1968

  • $/SqFt

    $279

Come take a tour of this immaculate 4 bedrooms, 2 bathrooms pool home today! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $589,000

Reduced By $41,000

Stunning two-story modern home showcasing a minimalist design with black and white colors and a well-manicured lawn at 5255 Seminole Ave, Winter Park, FL 32792
View Details 87 Photos
Modern kitchen featuring white cabinets, stainless steel appliances, a black farmhouse sink, and marble countertops at 5255 Seminole Ave, Winter Park, FL 32792
Bright kitchen featuring a breakfast bar, white marble countertops, sleek black hardware, and stainless steel appliances at 5255 Seminole Ave, Winter Park, FL 32792
Bright bedroom showcasing a sliding barn door to the closet, large windows, and sleek marble flooring at 5255 Seminole Ave, Winter Park, FL 32792
On Market For 141 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2170

  • Year Built

    1957

  • $/SqFt

    $271

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

Home For Sale $393,000

Reduced By $32,000

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 141 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1568

  • Year Built

    1956

  • $/SqFt

    $251

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.

Pended $299,000

Reduced By $51,000

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 142 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1493

  • Year Built

    1981

  • $/SqFt

    $200

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.

Home For Sale $885,000

Reduced By $10,000

Beige two-car garage door in the front of a gray two-story home with a paved brick driveway and walkway at 1263 Verdant Glade Pl, Winter Park, FL 32792
View Details 15 Photos
Two-story home with a light-beige exterior, two-car garage, and landscaped lawn at 1263 Verdant Glade Pl, Winter Park, FL 32792
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 with light-beige exterior, two-car garage, and gabled roof at 1263 Verdant Glade Pl, Winter Park, FL 32792
On Market For 150 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2589

  • Year Built

    2020

  • $/SqFt

    $342

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

Cute ranch home with red door, gray siding, and nicely landscaped yard at 1608 Bomi Cir, Winter Park, FL 32792
View Details 30 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 151 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.

Pended $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 144 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1032

  • Year Built

    1950

  • $/SqFt

    $436

Lawndale - all the information is intended to be accurate and must be verified by buyers / realtor agent. 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 157 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 $4,750,000

Reduced By $235,000

Stunning modern home featuring a grand entrance and meticulously landscaped front yard with paver driveway at 2161 Sharon Rd, Winter Park, FL 32789
View Details 62 Photos
Contemporary home boasting clean lines, a spacious driveway, and lush landscaping under a sunny sky at 2161 Sharon Rd, Winter Park, FL 32789
A modern residence showcased with an expansive paved driveway framed by manicured greenery at 2161 Sharon Rd, Winter Park, FL 32789
Elegant modern home with symmetrical design, manicured landscaping, and expansive driveway at twilight at 2161 Sharon Rd, Winter Park, FL 32789
On Market For 163 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6338

  • Year Built

    2023

  • $/SqFt

    $749

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

Pended $1,100,000

Reduced By $50,000

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 166 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2786

  • Year Built

    1960

  • $/SqFt

    $395

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 $518,000

Reduced By $44,000

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 167 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2122

  • Year Built

    1979

  • $/SqFt

    $244

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

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 173 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 $695,000

Reduced By $104,000

Charming yellow home featuring arched windows and a welcoming front entrance with potted plants at 786 Antonette Ave, Winter Park, FL 32789
View Details 36 Photos
A covered boathouse on a grassy lawn near the lake, featuring a fenced gate and wooden deck at 786 Antonette Ave, Winter Park, FL 32789
Covered boat dock with ceiling fans, Adirondack chairs, and boat lift ready for lake adventures at 786 Antonette Ave, Winter Park, FL 32789
An aerial shot of the home's location amid lush greenery and numerous lakes in Winter Park at 786 Antonette Ave, Winter Park, FL 32789
On Market For 175 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1146

  • Year Built

    1925

  • $/SqFt

    $606

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 $450,000

Reduced By $49,999

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 160 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1765

  • Year Built

    1963

  • $/SqFt

    $255

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 $8,799,000

Reduced By $2,200,999

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 176 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4564

  • Year Built

    2024

  • $/SqFt

    $1,928

Experience the pinnacle of luxury living—schedule a private tour today. PV LUXURY GROUP PA.

Home For Sale $2,799,000

Reduced By $500,000

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 184 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4875

  • Year Built

    2008

  • $/SqFt

    $574

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

Home For Sale $1,599,999

Reduced By $99,001

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 187 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3116

  • Year Built

    2014

  • $/SqFt

    $513

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
On Market For 187 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 $509,900

Reduced By $145,000

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 189 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2205

  • Year Built

    1965

  • $/SqFt

    $231

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

Home For Sale $455,000

Reduced By $120,000

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 149 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2290

  • Year Built

    1987

  • $/SqFt

    $199

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

Pended $450,000

Reduced By $49,000

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
On Market For 150 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1773

  • Year Built

    1953

  • $/SqFt

    $254

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

Home For Sale $425,000

Reduced By $24,000

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 197 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1725

  • Year Built

    1990

  • $/SqFt

    $246

LPT REALTY.

Pended $829,000

Reduced By $140,000

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 152 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    1813

  • Year Built

    1958

  • $/SqFt

    $457

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

Pended $675,000

Reduced By $74,999

Well maintained green two story home with landscaped front yard and matching green driveway at 3136 Heartleaf Pl, Winter Park, FL 32792
View Details 33 Photos
Front porch with rocking chair and seasonal decor at 3136 Heartleaf Pl, Winter Park, FL 32792
Living room with hardwood floors, high ceilings, and elegant decor at 3136 Heartleaf Pl, Winter Park, FL 32792
Open kitchen with breakfast bar and views to living room at 3136 Heartleaf Pl, Winter Park, FL 32792
On Market For 201 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2717

  • Year Built

    1995

  • $/SqFt

    $248

Lost Creek - Don’t miss your chance to own this exceptional home—schedule your showing today! ALL REAL ESTATE & INVESTMENTS.

Home For Sale $1,295,000

Reduced By $155,000

Stunning lakefront property with a private backyard and a sparkling swimming pool at 632 Country Club Dr, Winter Park, FL 32789
View Details 38 Photos
Charming lakeside home featuring a private dock, perfect for boating and enjoying waterfront living at 632 Country Club Dr, Winter Park, FL 32789
Elegant living room with French doors offering scenic views of the tranquil lake at 632 Country Club Dr, Winter Park, FL 32789
Inviting home with well-maintained landscaping and a charming exterior, perfect for curb appeal at 632 Country Club Dr, Winter Park, FL 32789
On Market For 207 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2342

  • Year Built

    1952

  • $/SqFt

    $553

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

Home For Sale $399,900

Two-car garage and pink exterior at 5418 S Bracken Ct, Winter Park, FL 32792
View Details 35 Photos
Kidney shaped swimming pool in backyard at 5418 S Bracken Ct, Winter Park, FL 32792
Living room with comfy seating and large TV at 5418 S Bracken Ct, Winter Park, FL 32792
Spacious living room with tile floors, ceiling fan, and sliding glass doors leading to a pool at 5418 S Bracken Ct, Winter Park, FL 32792
On Market For 209 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1301

  • Year Built

    1991

  • $/SqFt

    $307

Bridgewater - Schedule your showing today and submit your offers—don’t miss out on this beautiful home! EXP REALTY LLC.

Home For Sale $855,555

Reduced By $33,333

Mid-century modern home with a large front yard at 2128 Sycamore Dr, Winter Park, FL 32789
View Details 11 Photos
Mid-century modern home with white exterior, black accents, and a spacious lawn at 2128 Sycamore Dr, Winter Park, FL 32789
Mid-century modern home with white exterior, black accents, and a spacious lawn at 2128 Sycamore Dr, Winter Park, FL 32789
White mid-century modern home with a large backyard at 2128 Sycamore Dr, Winter Park, FL 32789
On Market For 211 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1760

  • Year Built

    1953

  • $/SqFt

    $486

Northwood Terrace - Act fast—opportunities like this don’t last long! EXP REALTY LLC.

Home For Sale $499,000

Reduced By $76,000

Mid-Century Ranch style home with mature trees and driveway at 2821 Chantilly Ave, Winter Park, FL 32789
View Details 18 Photos
Aerial view showing home's location near a pond at 2821 Chantilly Ave, Winter Park, FL 32789
Detailed survey map of the property and surrounding area at 2821 Chantilly Ave, Winter Park, FL 32789
Bright dining area with hardwood floors and kitchen view at 2821 Chantilly Ave, Winter Park, FL 32789
On Market For 214 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1440

  • Year Built

    1959

  • $/SqFt

    $347

Winter Park Manor - Extras include: updated electric panel, 2017 AC, updated plumbing & 24x12 backyard shed. WELCOME HOME! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $5,000,000

Reduced By $400,000

Two story home with lush landscaping and a circular driveway at 2228 Azalea Pl, Winter Park, FL 32789
View Details 34 Photos
Elegant home entrance with a pink door, arched entryway, and potted plants at 2228 Azalea Pl, Winter Park, FL 32789
House exterior showcasing a classic design with a green lawn at 2228 Azalea Pl, Winter Park, FL 32789
Vibrant living room with bold colors, unique artwork, and comfortable seating at 2228 Azalea Pl, Winter Park, FL 32789
On Market For 215 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5072

  • Year Built

    2008

  • $/SqFt

    $986

Maitland Shores - The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. COMPASS FLORIDA LLC.

Home For Sale $2,270,000

Reduced By $129,000

Modern home with pool and landscaped yard, offering an open floor plan and sleek design at 2522 Lafayette Ave, Winter Park, FL 32789
View Details 55 Photos
Contemporary home with gray and white exterior, showcasing a stylish and modern design at 2522 Lafayette Ave, Winter Park, FL 32789
Modern two-story home with a rooftop deck and attached garage, offering city views at 2522 Lafayette Ave, Winter Park, FL 32789
Stylish home with large windows and a modern facade, creating a welcoming curb appeal at 2522 Lafayette Ave, Winter Park, FL 32789
On Market For 215 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3399

  • Year Built

    2022

  • $/SqFt

    $668

The value on this beauty will soar as Lafayette is transformed into an extension to Temple Ave and the VIA'S of Winter Park, stay ahead of this transformation and make Winter Park Village your home! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $338,000

Reduced By $7,000

Charming light blue bungalow with a covered porch at 5080 Seminole Ave, Winter Park, FL 32792
View Details 35 Photos
Spacious backyard with lush green grass at 5080 Seminole Ave, Winter Park, FL 32792
Large backyard perfect for outdoor activities at 5080 Seminole Ave, Winter Park, FL 32792
Spacious backyard with a long driveway at 5080 Seminole Ave, Winter Park, FL 32792
On Market For 139 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1078

  • Year Built

    1924

  • $/SqFt

    $314

Don’t miss out on this fantastic home in a highly desirable area! SERHANT.

Home For Sale $3,499,500

Reduced By $392,500

Elegant two-story brick home with a landscaped yard at 1391 Richmond Rd, Winter Park, FL 32789
View Details 66 Photos
Grand two-story brick home with a circular driveway at 1391 Richmond Rd, Winter Park, FL 32789
Brick home nestled in lush landscaping, large driveway at 1391 Richmond Rd, Winter Park, FL 32789
Mature trees and landscaped gardens surround the home at 1391 Richmond Rd, Winter Park, FL 32789
On Market For 226 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    4635

  • Year Built

    2001

  • $/SqFt

    $755

Virginia Heights - Celebrate nature’s wildlife which range from owls, great white egrets, blue herons, hawks, bunnies, and otters in your private sanctuary minutes to Winter Park’s premier dining, upscale shopping, Mead Botanical Garden, and the highly coveted Audubon K-8, and Winter Park High! STOCKWORTH REALTY GROUP.

Home For Sale $599,900

Tan single-story house with a two-car garage and manicured lawn at 8162 Lazy Bear Ln, Winter Park, FL 32792
View Details 30 Photos
House exterior with a driveway, landscaping, and American flag at 8162 Lazy Bear Ln, Winter Park, FL 32792
Aerial view showcasing the house's location and neighborhood at 8162 Lazy Bear Ln, Winter Park, FL 32792
Bright entryway with hardwood floors and decorative console table at 8162 Lazy Bear Ln, Winter Park, FL 32792
On Market For 138 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1843

  • Year Built

    2013

  • $/SqFt

    $326

Enclave At Aloma - Security Video/Audio Devices Operating on Premises AUTHENTIC REAL ESTATE TEAM.

Pended $399,000

Reduced By $13,000

Single story home with a large front yard and driveway at 2140 Ridge Dr, Winter Park, FL 32792
View Details 38 Photos
Single story home with a large front yard and driveway at 2140 Ridge Dr, Winter Park, FL 32792
Single story home with a large front yard and driveway at 2140 Ridge Dr, Winter Park, FL 32792
Single story home with a large front yard and driveway at 2140 Ridge Dr, Winter Park, FL 32792
On Market For 172 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1554

  • Year Built

    1959

  • $/SqFt

    $257

Don’t miss out on the chance to own this fully renovated gem that’s move-in ready and waiting for you to make it your own! REAL BROKER, LLC.

Home For Sale $1,397,000

Reduced By $98,000

Stunning contemporary home with a white exterior, landscaped yard, and brick driveway at 1371 Lyndale Blvd, Winter Park, FL 32789
View Details 69 Photos
Modern home nestled on a tree-lined street with a brick road at 1371 Lyndale Blvd, Winter Park, FL 32789
Top-down view of a home showcasing its layout and landscaped yard at 1371 Lyndale Blvd, Winter Park, FL 32789
Aerial view of a home showcasing the property and surrounding neighborhood at 1371 Lyndale Blvd, Winter Park, FL 32789
On Market For 236 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2739

  • Year Built

    1949

  • $/SqFt

    $510

Dixie Terrace - With every detail thoughtfully curated, this property is more than just a home—it's a lifestyle. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $1,999,993

Reduced By $200,006

Two-story house with a double front door and landscaped yard at 1451 Lyndale Blvd, Winter Park, FL 32789
View Details 89 Photos
Home's side view, showcasing garage and landscaping at 1451 Lyndale Blvd, Winter Park, FL 32789
Inviting swimming pool with a spacious patio area at 1451 Lyndale Blvd, Winter Park, FL 32789
Two-story house with a double front door and landscaped yard at 1451 Lyndale Blvd, Winter Park, FL 32789
On Market For 260 Days

  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    3853

  • Year Built

    2012

  • $/SqFt

    $519

Dixie Terrace - Schedule your private showing today and discover what makes this Winter Park home truly exceptional. REALTY ONE GROUP MVP.

Home For Sale $580,000

Reduced By $70,000

Newly renovated brick and stucco ranch home with a well-maintained lawn at 274 N Ranger Blvd, Winter Park, FL 32792
View Details 40 Photos
Open concept living room with modern furniture and a view of the kitchen at 274 N Ranger Blvd, Winter Park, FL 32792
Open concept living room, featuring modern decor and a view into the kitchen at 274 N Ranger Blvd, Winter Park, FL 32792
Living Room with modern furniture, an open floor plan, and natural light at 274 N Ranger Blvd, Winter Park, FL 32792
On Market For 258 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1420

  • Year Built

    1963

  • $/SqFt

    $408

Don’t miss the chance to make this your new home – schedule a tour today! NETWORTH REALTY OF ORLANDO, LLC.

Home For Sale $805,000

Reduced By $34,000

White brick ranch home with landscaped lawn and driveway at 648 Brechin Dr, Winter Park, FL 32792
View Details 58 Photos
House exterior showcasing manicured lawn and driveway at 648 Brechin Dr, Winter Park, FL 32792
Front view of a renovated mid-century modern home at 648 Brechin Dr, Winter Park, FL 32792
Stylish blue front door and white brick facade at 648 Brechin Dr, Winter Park, FL 32792
On Market For 198 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1820

  • Year Built

    1961

  • $/SqFt

    $442

Kenilworth Shores - ( Owner financing,10% down payment at 5.75% interest rate) RAZZANI INTERNATIONAL REALTY.

Home For Sale $3,249,000

Reduced By $46,000

Stunning modern home with a stone chimney, manicured lawn, and a welcoming two-car garage at 1730 Winchester Dr, Winter Park, FL 32789
View Details 80 Photos
Inviting covered front porch with stylish seating, providing a tranquil outdoor space at 1730 Winchester Dr, Winter Park, FL 32789
Cozy outdoor living area with a stone fireplace and comfortable seating, perfect for relaxation at 1730 Winchester Dr, Winter Park, FL 32789
Elegant staircase featuring wood treads, iron railings, and stylish lighting at 1730 Winchester Dr, Winter Park, FL 32789
On Market For 271 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4080

  • Year Built

    2024

  • $/SqFt

    $796

Schedule your private tour today to see this stunning property in person! KELLER WILLIAMS WINTER PARK.

Viewing HOMES 251 to 300 of 323

EasyStreet

Call to Schedule a Showing

(954) 439-6446

(954) 439-6446