337 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $518,000

Charming one-story home featuring a well-manicured front yard, brick pathway, and a neatly painted garage door at 1921 Heathwood Dr, Winter Park, FL 32792
View Details 72 Photos
Inviting covered entry featuring double doors, textured walls, tiled floors, and natural light at 1921 Heathwood Dr, Winter Park, FL 32792
Bright entryway featuring double doors, hardwood flooring, and modern decor at 1921 Heathwood Dr, Winter Park, FL 32792
Cozy living room featuring neutral decor, plush seating, and abundant natural light at 1921 Heathwood Dr, Winter Park, FL 32792
On Market Today

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1611

  • Year Built

    1980

  • $/SqFt

    $322

Cedar Ridge - Don’t miss your chance to own this exceptional home! NEXTDWELL.

Home For Sale $499,900

Charming single-Gathering home featuring a two-car garage, lush lawn, and mature trees offering shade at 1173 Valley Creek Run, Winter Park, FL 32792
View Details 34 Photos
Beautifully landscaped front yard with a mature tree, green lawn, and a charming home exterior at 1173 Valley Creek Run, Winter Park, FL 32792
Well-maintained home with a manicured lawn, mature landscaping, and a two-car garage at 1173 Valley Creek Run, Winter Park, FL 32792
Spacious living room with tile flooring and a sliding glass door leading to the outdoor patio at 1173 Valley Creek Run, Winter Park, FL 32792
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1906

  • Year Built

    1995

  • $/SqFt

    $262

Don’t miss the opportunity to make this your next home! LUKER & CO REAL ESTATE LLC.

Home For Sale $3,599,999

Stunning two-story white home showcasing manicured landscaping, stone accents, and a circular driveway at 1761 Legion Dr, Winter Park, FL 32789
View Details 32 Photos
Beautifully landscaped side view of a modern home featuring a three-car garage and well-manicured lawn at 1761 Legion Dr, Winter Park, FL 32789
Elegant dining room with modern decor, mirrored wall, stylish lighting, and sophisticated artwork at 1761 Legion Dr, Winter Park, FL 32789
Bright living room featuring a large window, staircase, and contemporary furnishings for stylish comfort at 1761 Legion Dr, Winter Park, FL 32789
On Market For 2 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4955

  • Year Built

    2017

  • $/SqFt

    $727

Green Oaks - All just moments from the shops, dining, and charm of downtown Winter Park. SCANLON REALTY GROUP LLC.

Home For Sale $2,700,000

Modern two-story home with a brick and white facade, two-car garage, and a well-manicured lawn at 1781 Pine Ave, Winter Park, FL 32789
View Details 96 Photos
Open concept living room featuring a large sectional sofa, modern furniture, and access to the backyard at 1781 Pine Ave, Winter Park, FL 32789
Modern kitchen with white cabinets, a center island with seating, and stainless steel appliances at 1781 Pine Ave, Winter Park, FL 32789
Backyard pool and outdoor living area featuring a covered patio and an outdoor kitchen at 1781 Pine Ave, Winter Park, FL 32789
On Market Today

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3882

  • Year Built

    2017

  • $/SqFt

    $696

From the moment you step inside, you’ll fall in love with its elegance and charm. FLORIDA CONNEXION PROPERTIES.

Home For Sale $1,595,000

Modern two-story home boasting a clean white facade, black trim, manicured lawn, and contemporary landscaping at 1733 Harmon Ave, Winter Park, FL 32789
View Details 35 Photos
Modern home exterior featuring clean lines, white facade, and black trim, complemented by a lush green lawn at 1733 Harmon Ave, Winter Park, FL 32789
Modern two-story home boasting a clean white facade, black trim, manicured lawn, and contemporary landscaping at 1733 Harmon Ave, Winter Park, FL 32789
Bright home office featuring hardwood floors, large windows, a modern desk, and stylish decor at 1733 Harmon Ave, Winter Park, FL 32789
On Market Today

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3267

  • Year Built

    2025

  • $/SqFt

    $488

Lawndale - The Pool, the detached two-car garage, and the charming private flex suite are the perfect balance of elegance and comfort Located just minutes from the heart of Park Avenue Winter Park, with top-rated schools, healthcare, restaurants, and shopping, and just a few minutes driving to boat ramps and access to the famous chain of lakes, also a few blocks from downtown Orlando. SOUTH REALTY, INC.

Home For Sale $999,999

Charming brick home featuring a two-car garage, lush green lawn, and decorative landscaping at 2112 Fosgate Dr, Winter Park, FL 32789
View Details 34 Photos
Charming home entrance features a brick walkway, manicured bushes, and covered porch at 2112 Fosgate Dr, Winter Park, FL 32789
Elegant dining room with hardwood floors, a large rug, and a table set for six at 2112 Fosgate Dr, Winter Park, FL 32789
Bright dining room features hardwood floors, large windows with shutters, and neutral walls at 2112 Fosgate Dr, Winter Park, FL 32789
On Market Today

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2348

  • Year Built

    1957

  • $/SqFt

    $426

Don’t miss your chance to make it yours! KELLER WILLIAMS WINTER PARK.

Home For Sale $650,000

Traditional single-story home with a well-maintained lawn, mature trees, and a large driveway at 1730 Oneco Ave, Winter Park, FL 32789
View Details 12 Photos
A cozy single-story home with muted colors, shutters and mature landscaping at 1730 Oneco Ave, Winter Park, FL 32789
View of a lush backyard, featuring a screened-in porch at 1730 Oneco Ave, Winter Park, FL 32789
Spacious bedroom featuring a ceiling fan, closet and plenty of natural light at 1730 Oneco Ave, Winter Park, FL 32789
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1408

  • Year Built

    1967

  • $/SqFt

    $462

Winter Park Heights - This winter park corner lot is highly sought after for its location and its potential. THE TEAM REAL ESTATE GROUP INC.

Home For Sale $575,000

Well-manicured home featuring a spacious front yard, long driveway, and attached two car garage at 7852 Broken Arrow Trl, Winter Park, FL 32792
View Details 26 Photos
Inviting front porch with rocking chairs, and stately columns with decorative trim at 7852 Broken Arrow Trl, Winter Park, FL 32792
Bright and airy living room with large window, calming colors, and lots of comfortable seating at 7852 Broken Arrow Trl, Winter Park, FL 32792
Expansive open-concept kitchen with island seating, modern lighting, and light wood flooring at 7852 Broken Arrow Trl, Winter Park, FL 32792
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2219

  • Year Built

    1972

  • $/SqFt

    $259

Don’t miss your chance to own this irresistible gem, set in the serene neighborhood you’ve been looking for. Schedule your private showing today! CREEGAN GROUP.

Home For Sale $429,000

Charming single-story home with a well-maintained lawn and covered carport in a desirable neighborhood at 2809 Sanbina St, Winter Park, FL 32789
View Details 26 Photos
Charming single-story home with a well-maintained lawn and covered carport in a desirable neighborhood at 2809 Sanbina St, Winter Park, FL 32789
Sprawling backyard with a sparkling pool and lush landscaping at 2809 Sanbina St, Winter Park, FL 32789
Well maintained lawn, clean front exterior, and driveway parking at 2809 Sanbina St, Winter Park, FL 32789
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1140

  • Year Built

    1961

  • $/SqFt

    $376

Howell Heights - Don't miss this incredible opportunity, schedule your showing today! STRONG FOUNDATION REALTY LLC.

Home For Sale $425,000

Charming single-Gathering home with a brick facade and mature landscaping in a well-maintained yard at 3107 Ash Park Loop, Winter Park, FL 32792
View Details 24 Photos
Well-kept single-Gathering home with lush lawn, mature trees, and classic brick and siding exterior at 3107 Ash Park Loop, Winter Park, FL 32792
Charming home with brick accents, mature landscaping, and well-maintained lawn, in a peaceful setting at 3107 Ash Park Loop, Winter Park, FL 32792
Spacious living room with tile flooring, fireplace, and a wall of mirrors reflecting natural light at 3107 Ash Park Loop, Winter Park, FL 32792
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1518

  • Year Built

    1987

  • $/SqFt

    $280

This home will not last long. Schedule your showing today! COLDWELL BANKER REALTY.

Home For Sale $575,000

Charming single-story home with a well-maintained lawn, mature trees, and a long driveway at 1387 Sawgrass Court, Winter Park, FL 32792
View Details 30 Photos
Inviting single-story home with lush landscaping in front of the house and well-maintained bushes at 1387 Sawgrass Court, Winter Park, FL 32792
An aerial view of a lovely home near a golf course with lush greenery and a pond in a serene setting at 1387 Sawgrass Court, Winter Park, FL 32792
Aerial view of property near a golf course with lush greenery and a pond in a serene setting at 1387 Sawgrass Court, Winter Park, FL 32792
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1867

  • Year Built

    1979

  • $/SqFt

    $308

Greenview Winter Pines - Recent updates include: New windows 2023-24, New AC 2022, New driveway 2022, New fence 2022, roof 2015, New electrical panel 2022, updated porcelain tile. WELCOME HOME! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $489,000

Charming single story home with a large tree offering plenty of shade and curb appeal at 2648 Amsden Rd, Winter Park, FL 32792
View Details 40 Photos
Well-maintained single story home with a lush lawn and mature landscaping at 2648 Amsden Rd, Winter Park, FL 32792
Exterior view of the single story home showcasing the neutral colors, updated windows and manicured landscaping at 2648 Amsden Rd, Winter Park, FL 32792
Inviting front porch with hanging flower baskets, decorative plants, and updated windows at 2648 Amsden Rd, Winter Park, FL 32792
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1623

  • Year Built

    1959

  • $/SqFt

    $301

All measurements are approximate and should be verified by the buyer and their agent. CHOICEPOINTE REALTY, INC..

Home For Sale $299,900

Charming single-story home with a covered carport and well-maintained front yard at 7102 Easter St, Winter Park, FL 32792
View Details 25 Photos
Charming single-story home with a covered carport and well-maintained front yard at 7102 Easter St, Winter Park, FL 32792
Spacious covered carport with a fenced-in area and ample parking space at 7102 Easter St, Winter Park, FL 32792
Charming single-story home with a covered carport and well-maintained front yard at 7102 Easter St, Winter Park, FL 32792
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1114

  • Year Built

    1956

  • $/SqFt

    $269

Don’t miss it—come experience the charm, space, and unbeatable location for yourself! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $1,500,000

Charming blue two-story home with manicured lawn, lush landscaping, and brick walkway leading to the front door at 2401 Lafayette Ave, Winter Park, FL 32789
View Details 60 Photos
Aerial view of a beautiful blue home with manicured landscaping, brick drive, mature trees, and a lush green lawn at 2401 Lafayette Ave, Winter Park, FL 32789
View of the driveway and garage of a two-story blue house with a brick driveway and basketball hoop at 2401 Lafayette Ave, Winter Park, FL 32789
View of the house and porch with white columns, yellow accents, and brick walkway leading to the front door at 2401 Lafayette Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3349

  • Year Built

    2014

  • $/SqFt

    $448

Fontainebleau - Call to set your appointment to view this lovely home! DIVINE ESTATES REALTY LLC.

Home For Sale $1,210,000

Stunning home featuring a circular driveway and grand entrance with columns and mature landscaping at 4048 Gilder Rose Pl, Winter Park, FL 32792
View Details 80 Photos
Relaxing screened-in pool area with a built-in spa, outdoor seating, and a cozy fireplace at 4048 Gilder Rose Pl, Winter Park, FL 32792
Enclosed backyard with sparkling pool, covered outdoor living and towering palm trees at 4048 Gilder Rose Pl, Winter Park, FL 32792
Aerial view showcasing the home's layout, pool, circular driveway, and lush surrounding greenery at 4048 Gilder Rose Pl, Winter Park, FL 32792
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3321

  • Year Built

    1992

  • $/SqFt

    $364

Don’t miss this opportunity to make this exceptional Winter Park residence your own – COMPASS FLORIDA LLC.

Home For Sale $825,000

Charming home featuring a cozy porch, blue door, and well-maintained landscaping at 734 Maryland Ave, Winter Park, FL 32789
View Details 34 Photos
Close up shot of front door featuring a wreath and natural light at 734 Maryland Ave, Winter Park, FL 32789
Cozy porch with seating area, plants, and natural light at 734 Maryland Ave, Winter Park, FL 32789
Inviting living room with bright, white walls and hardwood floors at 734 Maryland Ave, Winter Park, FL 32789
On Market For 4 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1250

  • Year Built

    1925

  • $/SqFt

    $660

New roof, A/C, tankless hot water heater, electric, plumbing, bonus space, updated baths, kitchen, GE Cafe appliances, solid and stone counters, and more during previous major renovation 2021 by the exceptional Z Properties. HOMECOIN.COM.

Home For Sale $635,000

Charming home featuring a quaint front porch, manicured lawn, and lush landscaping with stone walkway at 1339 Orchid Ave, Winter Park, FL 32789
View Details 45 Photos
Inviting single-story home boasting a well-kept lawn, gravel driveway, and freshly painted exterior at 1339 Orchid Ave, Winter Park, FL 32789
Lovely home with a lush green lawn, mature trees, and a decorative palm tree in the front yard at 1339 Orchid Ave, Winter Park, FL 32789
Charming home featuring a cozy front porch, manicured landscaping, and a welcoming entrance at 1339 Orchid Ave, Winter Park, FL 32789
On Market For 4 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    789

  • Year Built

    1953

  • $/SqFt

    $805

Buyer and buyer's agent should verify all prior to submission. ABIDE REALTY.

Home For Sale $2,849,000

Stately home featuring dual garages, mature trees, lush landscaping and a brick paved driveway at dusk at 2652 Lake Howell Ln, Winter Park, FL 32792
View Details 71 Photos
Picturesque lake view featuring a wooden dock with a gazebo at sunset at 2652 Lake Howell Ln, Winter Park, FL 32792
Well-maintained home featuring dual garages, and a brick paved driveway at 2652 Lake Howell Ln, Winter Park, FL 32792
Long brick paved driveway framed by mature trees leads to the property at 2652 Lake Howell Ln, Winter Park, FL 32792
On Market For 5 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3898

  • Year Built

    1954

  • $/SqFt

    $731

Some of the upgrades include new roof in 2022, newer HVAC systems, new kitchen, new bathrooms, upgraded light fixtures, upgraded flooring, new expanded back porch deck with stunning views of lake and natural setting, new interior paint, new exterior paint, upgraded mother-in-law, guest house, office space, separate rental or teenager's retreat. COLDWELL BANKER REALTY.

Home For Sale $949,900

Charming single-story home with a well-manicured lawn, mature trees, and a welcoming blue front door at 609 Langholm Dr, Winter Park, FL 32789
View Details 34 Photos
Inviting home with a lush green lawn, trimmed hedges, and a large shade tree in a tranquil setting at 609 Langholm Dr, Winter Park, FL 32789
Well-maintained home featuring a spacious driveway, mature landscaping, and an attached two-car garage at 609 Langholm Dr, Winter Park, FL 32789
Close-up of a cozy front porch with a light blue door, decorative wreath, and charming landscaping at 609 Langholm Dr, Winter Park, FL 32789
On Market For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1981

  • Year Built

    1960

  • $/SqFt

    $480

Kenilworth Shores - This is a rare opportunity to own a turn-key home in a highly desirable community! JMO REAL ESTATE GROUP.

Home For Sale $1,425,000

Stunning aerial view of lakeside community featuring beautiful homes, lush trees, and tranquil waters at 2922 Reef Knot Pl, Winter Park, FL 32792
View Details 54 Photos
Charming home with a manicured lawn, brick driveway, and a three-car garage perfect for a Gathering at 2922 Reef Knot Pl, Winter Park, FL 32792
Gorgeous aerial view showcasing homes with pools in a community near the lake at 2922 Reef Knot Pl, Winter Park, FL 32792
Bright and airy living room seamlessly connects to the kitchen for modern, open-concept living at 2922 Reef Knot Pl, Winter Park, FL 32792
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3153

  • Year Built

    2019

  • $/SqFt

    $452

Conveniently located near shopping, dining, and top-rated schools this is a rare opportunity for lakefront living in a prime location! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $775,000

Charming single-story home features a well-maintained lawn and classic white-painted brick facade at 1961 Winter Park Rd, Winter Park, FL 32789
View Details 29 Photos
Stunning aerial view of the property, highlighting its lush surroundings, and proximity to a lake at 1961 Winter Park Rd, Winter Park, FL 32789
Spacious living room features neutral paint, large tile flooring, and lots of natural light at 1961 Winter Park Rd, Winter Park, FL 32789
Bright living room with tile floors, a decorative fireplace, and abundant natural light at 1961 Winter Park Rd, Winter Park, FL 32789
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1598

  • Year Built

    1958

  • $/SqFt

    $485

Charmont - Don’t miss your chance—schedule your private showing today! THE REAL ESTATE PRINCIPLE, INC.

Home For Sale $998,000

Beautiful two-story home with a stone-accented entrance and well-manicured lawn at 1319 Heavenly Cv, Winter Park, FL 32792
View Details 23 Photos
Modern kitchen with sleek white cabinets, stainless steel appliances and waterfall island with seating at 1319 Heavenly Cv, Winter Park, FL 32792
Bright foyer with hardwood floors, wrought iron railing, and soaring ceilings overlooking the living room at 1319 Heavenly Cv, Winter Park, FL 32792
Elegant dining room with a modern chandelier, tray ceiling, and a large table with seating for twelve at 1319 Heavenly Cv, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 7 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4088

  • Year Built

    2015

  • $/SqFt

    $244

Also included are solar panels which drastically reduce electricity costs. This home has it all! COMMUNITY REALTY ASSOCIATES.

Home For Sale $2,399,000

An elegant two-story home featuring lush landscaping, a circular driveway and tasteful architectural details at 922 N Pennsylvania Ave, Winter Park, FL 32789
View Details 39 Photos
Inviting covered front porch with stone columns, wooden front door, and manicured landscaping at 922 N Pennsylvania Ave, Winter Park, FL 32789
Open-concept living room featuring tile floors, a staircase with iron railing, and views to the backyard at 922 N Pennsylvania Ave, Winter Park, FL 32789
Bright and airy living room featuring custom built-ins, fireplace and comfortable seating at 922 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    4

  • Sq. Ft.

    3440

  • Year Built

    2001

  • $/SqFt

    $697

A rare gem in an unbeatable location! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $567,000

Charming single-story home with a well-manicured lawn and covered carport at 1901 Loch Berry Rd, Winter Park, FL 32792
View Details 13 Photos
Inviting single-Gathering home featuring a spacious carport and lush green lawn at 1901 Loch Berry Rd, Winter Park, FL 32792
Aerial view showcases the property's proximity to Winter Park in a leafy neighborhood at 1901 Loch Berry Rd, Winter Park, FL 32792
An aerial view shows the location of the home in a tree-filled neighborhood near Winter Park at 1901 Loch Berry Rd, Winter Park, FL 32792
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1420

  • Year Built

    1957

  • $/SqFt

    $399

Kenilworth Shores - Showings of the home will be accommodated only by limited request due to current occupancy. FOLIO REALTY LLC.

Pended $459,900

Charming single-story home with white exterior, dark shutters, and well-manicured landscaping at 7446 Houston E Ct, Winter Park, FL 32792
View Details 25 Photos
A beautifully renovated single-story home featuring fresh landscaping and a well-maintained lawn at 7446 Houston E Ct, Winter Park, FL 32792
Inviting front entrance with double doors, decorative black tile, and fresh landscape at 7446 Houston E Ct, Winter Park, FL 32792
Bright foyer featuring neutral paint colors, wood-look floors, and a modern front door at 7446 Houston E Ct, Winter Park, FL 32792
On Market For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1795

  • Year Built

    1971

  • $/SqFt

    $256

Don’t miss your chance to own this stunning property—schedule your showing today! KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $425,000

Charming single-story home with well-maintained landscaping and a two-car garage at 5559 Pats Pt, Winter Park, FL 32792
View Details 19 Photos
Inviting single-story home featuring a two-car garage and mature landscaping at 5559 Pats Pt, Winter Park, FL 32792
Bright and airy living room with tile flooring and large windows, creating an open feel at 5559 Pats Pt, Winter Park, FL 32792
Spacious living room featuring neutral tile flooring, a window, and adjacent dining area at 5559 Pats Pt, Winter Park, FL 32792
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1613

  • Year Built

    2003

  • $/SqFt

    $263

Bear Gully Forest - Schedule your showing today so you don't miss out on this gem. RED BIRD REALTY OF FLORIDA INC.

Home For Sale $379,500

Charming single-story home with a two-car garage, a well-maintained lawn, and mature trees in the background at 1050 Reading Ct, Winter Park, FL 32792
View Details 18 Photos
Spacious living room featuring neutral carpeting, a modern chandelier, and ample natural light from a window at 1050 Reading Ct, Winter Park, FL 32792
Spacious living room featuring neutral carpeting, a modern chandelier, and ample natural light from a window at 1050 Reading Ct, Winter Park, FL 32792
Open-concept living room featuring tile flooring and sliding glass doors to the outdoor patio at 1050 Reading Ct, Winter Park, FL 32792
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1637

  • Year Built

    1983

  • $/SqFt

    $232

Priced to sell. Will Not Last! REALTY TECH INC.

Home For Sale $3,300,000

Striking two-story modern home featuring a stone accent wall and professionally landscaped front yard at 1820 Englewood Rd, Winter Park, FL 32789
View Details 48 Photos
Striking two-story modern home featuring a stone accent wall and professionally landscaped front yard at 1820 Englewood Rd, Winter Park, FL 32789
Attractive modern two-story house with white stucco, stone accents, and lush green lawn at 1820 Englewood Rd, Winter Park, FL 32789
Modern home with a three-car garage, a large window, and a beautifully landscaped yard at 1820 Englewood Rd, Winter Park, FL 32789
On Market For 9 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4263

  • Year Built

    2015

  • $/SqFt

    $774

Additional highlights: whole-house generator, water filtration, foam insulation, sweep-in vacuum, and an EV-ready garage with custom storage. KELLER WILLIAMS ADVANTAGE III.

Home For Sale $1,200,000

Charming yellow home with a lush front yard, white picket fence, and a bright blue front door at 835 Antonette Ave, Winter Park, FL 32789
View Details 42 Photos
Inviting front entrance with a bright blue door, brick steps, and decorative potted plants on each side at 835 Antonette Ave, Winter Park, FL 32789
Bright living room with hardwood floors, a ceiling fan, and neutral decor creating a cozy atmosphere at 835 Antonette Ave, Winter Park, FL 32789
Spacious living room featuring gleaming hardwood floors, a ceiling fan, and bright natural light at 835 Antonette Ave, Winter Park, FL 32789
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1867

  • Year Built

    1925

  • $/SqFt

    $643

College Place - 4-Point inspection was completed, please see attachments for survey and for home details. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $950,000

Aerial view of home with brick driveway, two-car garage and luscious landscaping on a lake at 1018 Turner Rd, Winter Park, FL 32789
View Details 40 Photos
Charming single-story home with a lush green lawn and attached garage at 1018 Turner Rd, Winter Park, FL 32789
Waterfront property featuring a dock and boat lift, surrounded by lush greenery at 1018 Turner Rd, Winter Park, FL 32789
Relaxing lakeside yard with seating area and walkway to the main house at 1018 Turner Rd, Winter Park, FL 32789
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2237

  • Year Built

    1958

  • $/SqFt

    $425

Lake Bell Terrace - Call today to schedule your tour and start living the LAKE LIFE – where every day feels like a vacation! WEMERT GROUP REALTY LLC.

Home For Sale $650,000

Charming single-story home featuring a lush front yard and attached two-car garage at 1507 Golfside Dr, Winter Park, FL 32792
View Details 28 Photos
Beautiful aerial view of a well-maintained home overlooking a golf course at 1507 Golfside Dr, Winter Park, FL 32792
A well maintained home with a pool, surrounded by mature trees and landscaping adjacent to golf course at 1507 Golfside Dr, Winter Park, FL 32792
Expansive, well-maintained back yard with lush green grass, trees, and a screened in patio at 1507 Golfside Dr, Winter Park, FL 32792
On Market For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2003

  • Year Built

    1981

  • $/SqFt

    $325

Greenview Winter Pines - Bring your vision and renovation ideas to transform this gem into your own private retreat! WELCOME HOME! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $425,000

Charming single-story home with a well-maintained lawn and an attached two-car garage at 2003 Bentwood Dr, Winter Park, FL 32792
View Details 28 Photos
Charming single-story home with a well-maintained lawn and an attached two-car garage at 2003 Bentwood Dr, Winter Park, FL 32792
Single-story home with a well-maintained lawn and a two-car garage at 2003 Bentwood Dr, Winter Park, FL 32792
Single-story home with well-maintained landscaping and a two-car garage at 2003 Bentwood Dr, Winter Park, FL 32792
On Market For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1675

  • Year Built

    1981

  • $/SqFt

    $254

Cedar Ridge - This home offers both comfort and convenience in one wonderful package and is ready for someone to personalize and make it truly their own. PALMANO GROUP RE BROKERAGE LLC.

Home For Sale $1,180,000

Charming two-story home features a manicured lawn, brick driveway, and inviting front porch with second-story balcony at 2607 Lafayette Ave, Winter Park, FL 32789
View Details 72 Photos
Charming two-story home features a manicured lawn, brick driveway, and inviting front porch with second-story balcony at 2607 Lafayette Ave, Winter Park, FL 32789
Charming two-story home features a manicured lawn, brick driveway, and inviting front porch with second-story balcony at 2607 Lafayette Ave, Winter Park, FL 32789
Charming two-story home features a manicured lawn, brick driveway, and inviting front porch with second-story balcony at 2607 Lafayette Ave, Winter Park, FL 32789
On Market For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2770

  • Year Built

    2018

  • $/SqFt

    $426

Winter Park Village - Located just minutes from Park Avenue’s shopping and dining, Rollins College, the Winter Park Chain of Lakes, and zoned for A-rated Dommerich Elementary, Maitland Middle, and Winter Park High School—this property blends luxury, location, and lifestyle. FORTUNE INTERNATIONAL REALTY.

Home For Sale $775,000

Charming single-story home featuring a uniquely landscaped front yard and a cozy front patio at 1840 Laurel Rd, Winter Park, FL 32789
View Details 33 Photos
Stunning front exterior with paver driveway, mature landscaping, and a pergola detail at 1840 Laurel Rd, Winter Park, FL 32789
Covered front porch with a decorative door, textured walls, and paver flooring at 1840 Laurel Rd, Winter Park, FL 32789
Cozy covered porch with unique plants, textured wall and convenient door access at 1840 Laurel Rd, Winter Park, FL 32789
On Market For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2245

  • Year Built

    1957

  • $/SqFt

    $345

Charmont - Don’t miss this rare opportunity to create something truly special in the heart of Olde Winter Park! KEYSEEKERS REAL ESTATE.

Pended $675,000

Charming home featuring lush landscaping and mature trees in a serene front yard setting at 4030 Cool Water Ct, Winter Park, FL 32792
View Details 75 Photos
Attractive home exterior with a well-manicured lawn and mature trees providing ample shade at 4030 Cool Water Ct, Winter Park, FL 32792
Well-maintained home featuring a manicured lawn and mature trees shading the front of the house at 4030 Cool Water Ct, Winter Park, FL 32792
Lovely home with a well-kept lawn and shade trees highlighting the property's curb appeal at 4030 Cool Water Ct, Winter Park, FL 32792
On Market For 11 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2910

  • Year Built

    1979

  • $/SqFt

    $232

Don’t miss this exceptional opportunity, schedule your private showing today! CREEGAN GROUP.

Pended $1,300,000

Charming home with mature trees and well-manicured lawn at 171 Cortland Ave, Winter Park, FL 32789
View Details 23 Photos
Charming home with mature trees and well-manicured lawn at 171 Cortland Ave, Winter Park, FL 32789
Charming home with mature trees and well-manicured lawn at 171 Cortland Ave, Winter Park, FL 32789
Backyard with mature trees at 171 Cortland Ave, Winter Park, FL 32789
On Market For 12 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1683

  • Year Built

    1940

  • $/SqFt

    $772

Cortland Park - You will live just minutes away from top rated schools, healthcare, restaurants and shopping and just a few minutes' drive to boat ramp access to Winter Parks famous chain of lakes. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $779,000

Charming home featuring a well-manicured lawn and palm trees, offering a welcoming curb appeal at 103 Longhorn Rd, Winter Park, FL 32792
View Details 59 Photos
Inviting front porch with a white brick facade, plants, and a walkway, perfect for relaxing outdoors at 103 Longhorn Rd, Winter Park, FL 32792
Outdoor patio area featuring comfortable seating, a dining table, and a stylish design, perfect for entertaining at 103 Longhorn Rd, Winter Park, FL 32792
The exterior of a single story home with white paint, white framed windows and a grey roof at 103 Longhorn Rd, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 11 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3493

  • Year Built

    1969

  • $/SqFt

    $223

Call today to schedule your showing. KELLER WILLIAMS WINTER PARK.

Home For Sale $570,000

Charming single-story home featuring a well-manicured lawn and attached two-car garage at 3231 Lowndes Dr, Winter Park, FL 32792
View Details 3 Photos
Traditional brick home with a lush green lawn, mature trees, and a welcoming front porch at 3231 Lowndes Dr, Winter Park, FL 32792
Spacious backyard with lush green grass, stepping stones, and mature trees providing shade at 3231 Lowndes Dr, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1749

  • Year Built

    1965

  • $/SqFt

    $326

Georgetown Estates - Close to shopping and dining, excellent location with everything you need. LA ROSA REALTY KISSIMMEE.

Pended $480,000

Charming single-story home featuring a solar panel roof, well-manicured lawn, and attached two-car garage at 2832 Buccaneer Dr, Winter Park, FL 32792
View Details 59 Photos
Aerial view of a beautiful home with a solar panel roof, screened-in pool, and fenced yard at 2832 Buccaneer Dr, Winter Park, FL 32792
Aerial view of a home with a screened pool, playground, solar panel roof, and a spacious backyard at 2832 Buccaneer Dr, Winter Park, FL 32792
Inviting single-story house with a gray roof, solar panels, two-car garage, and well-kept front yard at 2832 Buccaneer Dr, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1736

  • Year Built

    1984

  • $/SqFt

    $276

Come experience the lifestyle you’ve been waiting for! ORLANDO EXPERT REALTY LLC.

Home For Sale $399,900

Charming single-story home with a well-maintained lawn and landscaping, set under a partly cloudy sky at 7331 Blue Jacket W Pl, Winter Park, FL 32792
View Details 30 Photos
Spacious backyard featuring a screened lanai, partial fencing, and lush greenery, perfect for outdoor living at 7331 Blue Jacket W Pl, Winter Park, FL 32792
Modern kitchen with stainless steel appliances, white cabinetry, a stylish backsplash, and sleek gray flooring at 7331 Blue Jacket W Pl, Winter Park, FL 32792
Bright kitchen featuring stainless steel appliances, white cabinets, updated backsplash, and ample counter space at 7331 Blue Jacket W Pl, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1581

  • Year Built

    1970

  • $/SqFt

    $253

Woodcrest - Buyer responsible for their own due diligence. SAVVY AVENUE, LLC.

Home For Sale $269,000

Reduced By $30,000

Beautiful aerial view of lakeside home with lush trees and a large lake at 1979 Staunton Ave, Winter Park, FL 32789
View Details 21 Photos
Charming home with mature trees, lush green grass, and a blue front door at 1979 Staunton Ave, Winter Park, FL 32789
Inviting living room featuring gleaming hardwood floors, neutral walls, and open layout at 1979 Staunton Ave, Winter Park, FL 32789
Bright living room showcasing hardwood floors, white door, and convenient breakfast bar at 1979 Staunton Ave, Winter Park, FL 32789
On Market For 12 Days

  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    736

  • Year Built

    1948

  • $/SqFt

    $365

Karolina On Killarney - Do Not Submit Offers Site Unseen! CORBELO LLC.

Pended $497,500

Charming single-story home with lush landscaping and mature trees lining the front yard at 2817 Fitzooth Dr, Winter Park, FL 32792
View Details 26 Photos
Private backyard pool surrounded by a spacious patio and lush greenery for relaxation at 2817 Fitzooth Dr, Winter Park, FL 32792
Inviting backyard pool featuring a white concrete surround and verdant landscaping at 2817 Fitzooth Dr, Winter Park, FL 32792
Functional kitchen with stainless steel refrigerator, black dishwasher, and bright cabinetry at 2817 Fitzooth Dr, Winter Park, FL 32792
On Market For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1619

  • Year Built

    1965

  • $/SqFt

    $307

Pool equipment at the home, washer and dryer and 2nd refrigerator in garage is included. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $1,125,000

Stunning home with elegant architectural details, mature landscaping, and palm trees at 2880 Old Castle Dr, Winter Park, FL 32792
View Details 32 Photos
Gated entrance to the community with brick pillars, providing privacy and security at 2880 Old Castle Dr, Winter Park, FL 32792
Well-equipped kitchen with stainless steel appliances, granite countertops, and white cabinetry at 2880 Old Castle Dr, Winter Park, FL 32792
Spacious kitchen with granite countertops, double sinks, hardwood floors and stainless appliances at 2880 Old Castle Dr, Winter Park, FL 32792
On Market For 14 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3839

  • Year Built

    1993

  • $/SqFt

    $293

This is Florida living at its finest. CORCORAN PREMIER REALTY.

Pended $779,000

Charming home featuring an attached two-car garage, well-maintained landscaping, and mature palm trees at 1823 Sunset Dr, Winter Park, FL 32789
View Details 1 Photo
On Market For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2414

  • Year Built

    1940

  • $/SqFt

    $323

Call today for your private tour ! ! COMPASS FLORIDA LLC.

Home For Sale $1,495,000

Inviting two-story home featuring a well-manicured lawn, blue shutters and a paver driveway leading to a two-car garage at 1420 Palmer Ave, Winter Park, FL 32789
View Details 47 Photos
Backyard pool area perfect for relaxing, with outdoor seating and well-maintained landscaping, offering a private oasis at 1420 Palmer Ave, Winter Park, FL 32789
A beautiful backyard pool with a tranquil waterfall, lounge chairs, and lush landscaping against a colorful sunset backdrop at 1420 Palmer Ave, Winter Park, FL 32789
Bright foyer with hardwood floors, staircase, and an archway that leads to a dining area with stylish decor at 1420 Palmer Ave, Winter Park, FL 32789
On Market For 16 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2953

  • Year Built

    2004

  • $/SqFt

    $506

Comstock Park - (Roof: 2019, HVAC 2017, Mini Splits (2) 2024, Electrical 2004, Plumbing 2004) KELLER WILLIAMS WINTER PARK.

Home For Sale $799,000

Charming single-story home with a well-manicured lawn and inviting curb appeal under a gorgeous sunset sky at 676 Dunblane Dr, Winter Park, FL 32792
View Details 43 Photos
Inviting front entrance featuring a blue door, white columns, and a cozy seating area at 676 Dunblane Dr, Winter Park, FL 32792
Relaxing front porch with stylish seating, perfect for enjoying the outdoors at 676 Dunblane Dr, Winter Park, FL 32792
Bright white front door with decorative glass and classic hardware, offering a welcoming entry at 676 Dunblane Dr, Winter Park, FL 32792
On Market For 15 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1962

  • $/SqFt

    $437

676 Dunblane Drive is a rare opportunity to own a well-located, move-in-ready home in one of Winter Park’s most established and sought-after neighborhoods. Book your private showing TODAY! BALDWIN PARK REALTY LLC.

Pended $449,000

Charming single-story home boasts a well-manicured lawn, beautiful landscaping, and a welcoming front entrance at 2312 Poinciana Rd, Winter Park, FL 32792
View Details 36 Photos
Lovely exterior view of single-story home, featuring a well-kept lawn and an attached two-car garage at 2312 Poinciana Rd, Winter Park, FL 32792
Lovely one-story home with a well-maintained lawn and mature tree at 2312 Poinciana Rd, Winter Park, FL 32792
Enclosed front entrance with an arched gateway, adorned with brick accents and decorative wall cutouts at 2312 Poinciana Rd, Winter Park, FL 32792
On Market For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1806

  • Year Built

    1972

  • $/SqFt

    $249

Winter Woods - Whether you're starting a new chapter or looking to settle into a welcoming neighborhood, this home has everything you need and more. KELLER WILLIAMS WINTER PARK.

Home For Sale $439,999

Charming single-story home with a well-manicured lawn, mature trees, and a two-car garage on a sunny day at 2209 Fairglenn Way, Winter Park, FL 32792
View Details 30 Photos
Inviting front entrance with a decorative door, potted plants, brick accents, and stylish house numbers at 2209 Fairglenn Way, Winter Park, FL 32792
Comfortable living room with tile floors, ample seating, large windows, and a decorative ceiling fan at 2209 Fairglenn Way, Winter Park, FL 32792
Bright living area with tile floors, ceiling fan, arched windows, and elegant furnishings at 2209 Fairglenn Way, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2027

  • Year Built

    1986

  • $/SqFt

    $217

Retail Locations Walmart- 1.3 miles Publix- 1.3 miles Kohls- 1.4 miles Schools Red Bug Elementary- 2.3 miles Tuscawilla Middle School- .5 miles Lake Howell High School- 1.1 miles Don’t miss your chance to make this well-maintained home your own—schedule your showing today! HIVE REALTY LLC.

Home For Sale $423,000

Reduced By $7,000

Inviting front entry features double glass doors and colorful flower arrangement at 5436 Tangerine Ave, Winter Park, FL 32792
View Details 33 Photos
Bright kitchen with white cabinetry, modern appliances and quartz countertops at 5436 Tangerine Ave, Winter Park, FL 32792
Updated kitchen featuring white cabinetry, stainless steel appliances and subway tile backsplash at 5436 Tangerine Ave, Winter Park, FL 32792
Open kitchen layout with new appliances, quartz countertops and wood flooring at 5436 Tangerine Ave, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1996

  • Year Built

    1977

  • $/SqFt

    $212

Wrenwood Heights - Meticulously maintained, tastefully updated, and move-in ready — schedule your private showing today! CALL IT CLOSED INTL REALTY.

Home For Sale $4,175,000

Stunning modern home with manicured lawn, dark trim, and lush landscaping at 1581 Forest Ave, Winter Park, FL 32789
View Details 45 Photos
Beautiful home featuring a lush green lawn, manicured landscaping, and modern architectural design at 1581 Forest Ave, Winter Park, FL 32789
Striking modern home featuring manicured landscaping, mature trees, and a covered front entrance at 1581 Forest Ave, Winter Park, FL 32789
Elegant foyer features black-and-white checkered floors, a dazzling chandelier, and grand staircase at 1581 Forest Ave, Winter Park, FL 32789
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4683

  • Year Built

    1954

  • $/SqFt

    $892

(Don't miss the secret wine room!) BHHS FLORIDA REALTY.

Viewing HOMES 1 to 50 of 337

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 407-278-2057 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$498,791
$439,900
148
1.4%
56.8%
86

Apopka
$533,403
$480,000
582
1.4%
48.8%
85

Belle Isle
$883,969
$679,950
20
0.0%
45.0%
75

Casselberry
$415,485
$399,998
96
3.1%
57.3%
69

Celebration
$1,262,401
$973,995
50
0.0%
48.0%
89

Champions Gate
$686,906
$675,000
16
0.0%
43.8%
311

Chuluota
$889,383
$725,000
23
0.0%
47.8%
52

Clermont
$576,514
$492,500
742
0.7%
53.5%
76

Gotha
$1,050,253
$735,000
15
0.0%
53.3%
55

Groveland
$475,151
$400,000
281
1.1%
62.6%
86

Harmony
$438,294
$419,900
75
0.0%
40.0%
96

Kissimmee
$518,210
$444,445
2414
1.8%
51.3%
105

Longwood
$749,985
$555,000
219
0.9%
55.3%
72

Maitland
$1,031,824
$639,450
104
1.9%
52.9%
78

Minneola
$566,319
$542,697
146
0.0%
46.6%
79

Montverde
$1,529,128
$1,097,971
52
0.0%
51.9%
116

Ocoee
$526,966
$484,900
183
1.1%
44.3%
74

Orlando
$681,206
$499,900
3121
1.6%
51.0%
80

Oviedo
$704,284
$617,500
234
0.9%
53.0%
69

Poinciana
$323,520
$310,000
284
1.8%
55.6%
128

Reunion
$1,790,755
$1,059,950
110
2.7%
54.5%
162

Saint Cloud
$693,340
$532,500
36
5.6%
61.1%
313

Sanford
$523,650
$419,000
391
0.8%
51.2%
92

Sorrento
$619,137
$473,815
102
1.0%
49.0%
94

Windermere
$2,099,803
$1,295,000
287
0.0%
44.9%
96

Winter Garden
$869,688
$723,000
618
0.6%
51.6%
85

Winter Springs
$608,142
$489,900
148
0.7%
52.0%
75

EasyStreet

Call to Schedule a Showing

(407) 278-2057

(407) 278-2057