335 Results

View 335 Winter Park Florida Homes for Sale

Pended $645,000

Charming single-story home featuring dual entryways, brick driveway, and mature tree providing ample shade at 1773 Walnut Ave, Winter Park, FL 32789
View Details 4 Photos
View of a well-maintained home with a brick driveway and lush landscaping, including mature trees and manicured hedges at 1773 Walnut Ave, Winter Park, FL 32789
Single-story home with dual entrances, brick driveway, and mature trees, blending comfort and curb appeal at 1773 Walnut Ave, Winter Park, FL 32789
Attractive home with mature shade tree, manicured hedges, and brick driveway creating a welcoming curb appeal at 1773 Walnut Ave, Winter Park, FL 32789
On Market For 34 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2146

  • Year Built

    1957

  • $/SqFt

    $301

Conwill Estates - This property is being sold as a teardown. CORCORAN PREMIER REALTY.

Home For Sale $519,900

Reduced By $60,000

Charming single-story home with stone facade, well-manicured lawn, mature trees, and a paved driveway at 7679 Bent Bow Trl, Winter Park, FL 32792
View Details 70 Photos
Charming single-story home featuring a well-maintained lawn and a two-car garage at 7679 Bent Bow Trl, Winter Park, FL 32792
The entrance features a gray stone wall, two doors and gray concrete flooring at 7679 Bent Bow Trl, Winter Park, FL 32792
Living room with wood floors, decorative trim, a white front door, and large window at 7679 Bent Bow Trl, Winter Park, FL 32792
On Market For 38 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2616

  • Year Built

    1971

  • $/SqFt

    $199

Call today for a private showing. GILKEY REAL ESTATE.

Home For Sale $2,195,000

Reduced By $154,000

Stately two-story home featuring a terracotta roof, arched windows with flower boxes and lush landscaping at 1361 Palmer Ave., Winter Park, FL 32789
View Details 43 Photos
Two-story home featuring a terracotta roof, arched windows with flower boxes and mature shade trees at 1361 Palmer Ave., Winter Park, FL 32789
Circular driveway featuring a brick paver design and lush landscaping providing privacy at 1361 Palmer Ave., Winter Park, FL 32789
Spacious living room with polished floors, pillars, and sliding glass doors leading to the outdoor pool at 1361 Palmer Ave., Winter Park, FL 32789
On Market For 40 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3558

  • Year Built

    2005

  • $/SqFt

    $617

Temple Heights - Ideally in the Winter Park school district and just minutes from Phelps Park, Park Avenue, Interlachen Country Club, Winter Park Racquet Club and Rollins College, this home presents an unparalleled opportunity to enjoy refined living in one of Central Florida’s desirable communities. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $465,000

Reduced By $10,000

Charming single-story home with a well-manicured lawn, lush landscaping, and an attached two-car garage at 3304 Bennington Ct, Winter Park, FL 32792
View Details 32 Photos
Bright, open-concept living room featuring hardwood floors, modern decor and seamless flow into the kitchen at 3304 Bennington Ct, Winter Park, FL 32792
Open living room with wood floors and sliding glass doors to the outdoor space at 3304 Bennington Ct, Winter Park, FL 32792
Open living room features wood floors and view of archways leading into other rooms at 3304 Bennington Ct, Winter Park, FL 32792
On Market For 38 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1804

  • Year Built

    2003

  • $/SqFt

    $258

You won’t want to miss it! DAHLIA REALTY GROUP.

Home For Sale $429,900

Reduced By $19,100

Charming home featuring a covered porch, updated fixtures, and freshly painted exterior at 1842 Puritan Ave, Winter Park, FL 32792
View Details 23 Photos
Bright living room showcasing new floors, fresh paint, and lots of natural light at 1842 Puritan Ave, Winter Park, FL 32792
Open-concept living room with a modern design and updated kitchen appliances at 1842 Puritan Ave, Winter Park, FL 32792
Open-concept living room and kitchen with light wood floors and recessed lighting throughout the space at 1842 Puritan Ave, Winter Park, FL 32792
On Market For 39 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1836

  • Year Built

    1963

  • $/SqFt

    $234

Eastbrook - Don’t miss this opportunity to own a fully updated home that combines comfort, quality, and convenience in one of Central Florida’s most sought-after communities. COMPASS FLORIDA LLC.

Home For Sale $379,900

Charming single-story home with well-manicured lawn and mature landscaping at 3121 Thistlehill Drive, Winter Park, FL 32792
View Details 29 Photos
Corner lot featuring a well-kept lawn and a charming single-story home at 3121 Thistlehill Drive, Winter Park, FL 32792
Beautiful home with a well-maintained lawn, mature trees, and a two-car garage at 3121 Thistlehill Drive, Winter Park, FL 32792
Close-up of a charming home's entry with brick accents and a secure gate at 3121 Thistlehill Drive, Winter Park, FL 32792
On Market For 34 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1503

  • Year Built

    1967

  • $/SqFt

    $253

Now it’s your turn to come in and make some new memories. Great deal! EXP REALTY LLC.

Home For Sale $710,000

Charming two-story home featuring a tile roof, neutral stucco exterior, and a brick paver driveway at 1147 Wildmeadow Run, Winter Park, FL 32792
View Details 38 Photos
Charming two-story home featuring a tile roof, neutral stucco exterior, and a brick paver driveway at 1147 Wildmeadow Run, Winter Park, FL 32792
Welcoming front porch featuring decorative sign, seating, and a charming front door with floral wreath at 1147 Wildmeadow Run, Winter Park, FL 32792
Bright entryway features wood-look floors, staircase with metal railing, and view of the dining and kitchen at 1147 Wildmeadow Run, Winter Park, FL 32792
On Market For 40 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2002

  • Year Built

    2020

  • $/SqFt

    $355

Meadows At Hawks Crest - The HOA fee includes lawn care and irrigation for the best of maintenance free living. HONEST REAL ESTATE COMPANY.

Pended $369,900

Charming single-Gathering home with a brick facade, attached garage and landscaped front yard at 1748 Harvest Cv, Winter Park, FL 32792
View Details 37 Photos
Picturesque backyard view featuring lush green grass and mature trees along a tranquil stream at 1748 Harvest Cv, Winter Park, FL 32792
Relaxing screened-in patio with a dining table, chairs, and potted plants for outdoor enjoyment at 1748 Harvest Cv, Winter Park, FL 32792
Inviting screened-in patio with dining area and view of the backyard at 1748 Harvest Cv, Winter Park, FL 32792
On Market For 35 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1368

  • Year Built

    1987

  • $/SqFt

    $270

Autumn Glen - With great bones, a prime location, and a price that leaves room for updates, this one is a smart buy in a neighborhood that rarely has homes available. EXP REALTY LLC.

Home For Sale $2,455,000

Stunning two-story white home featuring arched entry, front balcony, well-manicured landscaping and a wood-look garage door at 521 S Phelps Ave, Winter Park, FL 32789
View Details 34 Photos
Charming home at dusk with meticulously maintained landscaping and inviting curb appeal at 521 S Phelps Ave, Winter Park, FL 32789
Elegant home with a paver driveway, lush lawn, and a side-entry garage at twilight at 521 S Phelps Ave, Winter Park, FL 32789
Bright hallway with hardwood floors, staircase, and custom built-in storage at 521 S Phelps Ave, Winter Park, FL 32789
On Market For 41 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3883

  • Year Built

    2015

  • $/SqFt

    $632

Kenilworth Shores - This property brilliantly integrates cosmopolitan living while retaining the warmth of home at every corner. LA ROSA REALTY HORIZONS LLC.

Home For Sale $1,999,000

Reduced By $101,000

Charming single-story home with a mature landscaped front yard and red window shutters at 633 Balmoral Rd, Winter Park, FL 32789
View Details 25 Photos
Charming single-story home with a mature landscaped front yard and red window shutters at 633 Balmoral Rd, Winter Park, FL 32789
Rear exterior view of home with brick patio and French doors leading to backyard at 633 Balmoral Rd, Winter Park, FL 32789
Screened-in porch with wood flooring and ceiling fans overlooking lake view at 633 Balmoral Rd, Winter Park, FL 32789
On Market For 42 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2674

  • Year Built

    1968

  • $/SqFt

    $748

Kenilworth Shores - Whether you renovate or start fresh, this opportunity is a rare chance to craft your own lakeside retreat in one of Winter Park's most desirable locations. Call today for details. COMPASS FLORIDA LLC.

Home For Sale $1,554,950

Reduced By $40,000

Charming two-story home featuring stucco siding, a tile roof, arched windows, and a brick driveway at 952 Moss Ln, Winter Park, FL 32789
View Details 55 Photos
Charming two-story home featuring stucco siding, a tile roof, arched windows, and a brick driveway at 952 Moss Ln, Winter Park, FL 32789
Charming two-story home featuring stucco siding, a tile roof, arched windows, and a brick driveway at 952 Moss Ln, Winter Park, FL 32789
Side view of a charming two-story home featuring stucco siding, a tile roof, arched windows, and manicured landscaping at 952 Moss Ln, Winter Park, FL 32789
On Market For 41 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    3474

  • Year Built

    2008

  • $/SqFt

    $448

Maitland Shores - Schedule a showing today and step into a lifestyle of comfort, sophistication, and unparalleled charm at 952 Moss Ln—a true gem ready to become your forever home. THE SHOP REAL ESTATE CO..

Home For Sale $450,000

Charming single-story home with a manicured lawn, colorful flower beds, and an attached two-car garage at 619 Byron Rd, Winter Park, FL 32792
View Details 40 Photos
An overhead view of a well-maintained property with lush landscaping, a screened-in patio, and a defined property line at 619 Byron Rd, Winter Park, FL 32792
Inviting living room with hardwood floors and neutral decor, featuring a large sofa and entertainment center at 619 Byron Rd, Winter Park, FL 32792
Well-lit kitchen featuring white cabinets and ample counter space, providing a clean and functional cooking area at 619 Byron Rd, Winter Park, FL 32792
On Market For 41 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1349

  • Year Built

    1957

  • $/SqFt

    $334

Eastgate - This move-in-ready gem in a highly sought-after neighborhood won’t last—schedule your showing today! RE/MAX 200 REALTY.

Pended $398,000

Charming single-Gathering home with a well-manicured front yard, brick driveway, and an attached two-car garage at 2009 Nottingdale Ln, Winter Park, FL 32792
View Details 42 Photos
Charming single-Gathering home with a well-manicured front yard, brick driveway, and an attached two-car garage at 2009 Nottingdale Ln, Winter Park, FL 32792
Charming single-Gathering home with a well-manicured front yard, brick driveway, and an attached two-car garage at 2009 Nottingdale Ln, Winter Park, FL 32792
Charming single-Gathering home with a well-manicured front yard, brick driveway, and an attached two-car garage at 2009 Nottingdale Ln, Winter Park, FL 32792
On Market For 38 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1582

  • Year Built

    1980

  • $/SqFt

    $252

Cedar Ridge - This home has great bones and needs some TLC. OLDE TOWN BROKERS INC.

Home For Sale $2,590,000

Stunning two-story home featuring a black tile roof, white stucco, arched front door, and manicured landscaping at 185 Sylvan Blvd, Winter Park, FL 32789
View Details 9 Photos
Bright and airy living room with a modern fireplace, recessed lighting, and stylish furniture at 185 Sylvan Blvd, Winter Park, FL 32789
Gourmet kitchen featuring an island with seating, a custom range hood, and stainless steel appliances at 185 Sylvan Blvd, Winter Park, FL 32789
Serene bedroom with a tufted headboard, neutral color palette, and plenty of natural light at 185 Sylvan Blvd, Winter Park, FL 32789
On Market For 42 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3138

  • Year Built

    2025

  • $/SqFt

    $825

Sylvan Lake Shores - Schedule your private showing today and experience the epitome of luxury Winter Park living. COMPASS FLORIDA LLC.

Home For Sale $1,595,000

Charming single-story home with a tile roof, a brick driveway, and well-manicured landscaping at 1741 Palmer Ave, Winter Park, FL 32789
View Details 59 Photos
An estate home features a tile roof, a paved driveway, mature landscaping, and a private gate at 1741 Palmer Ave, Winter Park, FL 32789
A stucco house has a tile roof, a two-car garage, a brick entry gate, and a paved driveway at 1741 Palmer Ave, Winter Park, FL 32789
A stucco house has a tile roof, a brick entry gate, a private driveway, and mature landscaping at 1741 Palmer Ave, Winter Park, FL 32789
On Market For 42 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2351

  • Year Built

    2013

  • $/SqFt

    $678

Jenkins - Perfectly situated on the iconic, tree-lined Palmer Avenue, this home offers unbeatable walkability—just a short stroll to Phelps Park and mere minutes from the boutiques and dining of Park Avenue, Interlachen Country Club, and the Winter Park Racquet Club- set up your private showing today. CENTRAL FLORIDA PRIME REAL ESTATE LLC.

Home For Sale $850,000

Charming single-story home boasting a mix of modern wood and white siding, manicured lawn, and inviting curb appeal at 730 W Swoope Ave, Winter Park, FL 32789
View Details 72 Photos
View of a single story home with a wood and white exterior, partially fenced in, located on a residential street at 730 W Swoope Ave, Winter Park, FL 32789
A well maintained lawn with a small tree in the front yard, compliments a modern single story home at 730 W Swoope Ave, Winter Park, FL 32789
Close up of the exterior featuring modern wood siding, a secured glass door, and a manicured front lawn at 730 W Swoope Ave, Winter Park, FL 32789
On Market For 43 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2132

  • Year Built

    1950

  • $/SqFt

    $399

Carver Town - Come discover your new corner home and fall in love with everything Winter Park has to offer. LPT REALTY, LLC.

Pended $599,000

Charming two-story home with black front door, manicured landscaping and mature trees at 490 Shoreview Ave, Winter Park, FL 32789
View Details 35 Photos
Charming two-story home with black front door, manicured landscaping and mature trees at 490 Shoreview Ave, Winter Park, FL 32789
Beautiful aerial view of neighborhood homes and lake with city skyline in the distance at 490 Shoreview Ave, Winter Park, FL 32789
Aerial view of home, lush backyard, a detached garage and neighboring properties at 490 Shoreview Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 42 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2266

  • Year Built

    1935

  • $/SqFt

    $264

Killarney Estates - Don’t miss your chance to call this historic gem home! FLORIDA HOME TEAM REALTY LLC.

Pended $1,699,000

Reduced By $50,000

Beautiful two-story home featuring a manicured lawn and charming front porch with black shutters at 2339 Lafayette Ave, Winter Park, FL 32789
View Details 63 Photos
Aerial view of a neighborhood showcasing tree-lined streets and proximity to a lake and parks at 2339 Lafayette Ave, Winter Park, FL 32789
Stunning two-story home with black shutters, a lovely lawn, and well manicured landscaping at 2339 Lafayette Ave, Winter Park, FL 32789
Charming two-story home featuring a well-manicured lawn, landscaping, and a quaint porch at 2339 Lafayette Ave, Winter Park, FL 32789
On Market For 45 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3379

  • Year Built

    2005

  • $/SqFt

    $503

Fontainebleau - All measurements are approximate and Buyer is responsible to verify dimensions. COLLADO REAL ESTATE.

Home For Sale $510,000

Reduced By $10,000

An aerial view of a single-Gathering home with a large yard and mature trees in a residential neighborhood at 1742 Willa Cir, Winter Park, FL 32792
View Details 42 Photos
Charming single-story home with a brick and stucco facade and a well-manicured front yard at 1742 Willa Cir, Winter Park, FL 32792
Bright living room with neutral decor, wood floors, ceiling fan and lots of natural light at 1742 Willa Cir, Winter Park, FL 32792
Inviting front porch with a decorative wood front door and large windows at 1742 Willa Cir, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 45 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2313

  • Year Built

    1987

  • $/SqFt

    $220

This move-in-ready home combines comfort, convenience, and flexibility—an exceptional opportunity not to be missed. CENTURY 21 CARIOTI.

Home For Sale $250,000

Reduced By $49,995

Charming home featuring a cozy porch, brick driveway, and mature trees enhancing curb appeal at 1996 Indiana Ave, Winter Park, FL 32789
View Details 3 Photos
Charming single-story home with a covered porch and white trim, surrounded by lush greenery and trees at 1996 Indiana Ave, Winter Park, FL 32789
Exterior view of a cozy single-story home with a covered porch, nestled amongst mature trees and foliage at 1996 Indiana Ave, Winter Park, FL 32789
On Market For 36 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    818

  • Year Built

    1938

  • $/SqFt

    $306

Lawndale - City water and sewer connections are available on the property. MARKET CONNECT REALTY LLC.

Home For Sale $1,999,900

Modern two-story home with meticulously landscaped front yard and paver driveway, surrounded by mature palm trees at 1521 Chestnut Ave, Winter Park, FL 32789
View Details 55 Photos
Charming two-story home with landscaped front yard, paver driveway, and modern architectural details at sunset at 1521 Chestnut Ave, Winter Park, FL 32789
Modern home featuring a private pool, covered patio, second story balcony and lush backyard at sunset at 1521 Chestnut Ave, Winter Park, FL 32789
Overhead view of modern home, showcasing the roof, pool, driveway, and landscaped yard surrounded by neighboring properties at 1521 Chestnut Ave, Winter Park, FL 32789
On Market For 46 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3117

  • Year Built

    2022

  • $/SqFt

    $642

Lake Knowles Terrace - Don't miss your chance to own this exceptional home in the heart of Winter Park! COMPASS FLORIDA LLC.

Home For Sale $1,200,000

Breathtaking aerial view of a lakefront property with mature trees, offering serene privacy and natural beauty at 4107 Gabriella Ln, Winter Park, FL 32792
View Details 89 Photos
Charming home with a brick driveway and lush tropical landscaping surrounding the property at 4107 Gabriella Ln, Winter Park, FL 32792
Charming home with a brick driveway and lush tropical landscaping surrounding the property at 4107 Gabriella Ln, Winter Park, FL 32792
Lush front entrance with tropical landscaping leads to a welcoming doorway at 4107 Gabriella Ln, Winter Park, FL 32792
On Market For 47 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3074

  • Year Built

    1998

  • $/SqFt

    $390

Homes like this are rarely available—schedule your private showing today and experience the magic of Bear Gully Lake for yourself. KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $479,900

Reduced By $5,100

Charming single-story home featuring well-maintained landscaping, a lovely lawn, and mature shade trees at 3054 Bluebrook Dr, Winter Park, FL 32792
View Details 34 Photos
Beautiful in-ground swimming pool surrounded by lush landscaping and complemented by an outdoor pergola at 3054 Bluebrook Dr, Winter Park, FL 32792
The backyard features a screened-in porch and a pool deck that surrounds the in-ground pool at 3054 Bluebrook Dr, Winter Park, FL 32792
Enjoy outdoor cooking in this covered outdoor kitchen area, perfect for entertaining guests and Gathering at 3054 Bluebrook Dr, Winter Park, FL 32792
On Market For 46 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1939

  • Year Built

    1973

  • $/SqFt

    $247

Laurel Springs - Schedule your showing today and fall in love with your new forever home. ALORA REALTY GROUP INC.

Home For Sale $414,999

Reduced By $5,001

Charming single-story home with a lush front yard, mature trees, and a covered carport showcasing curb appeal at 920 Gloriosa Ave, Winter Park, FL 32789
View Details 51 Photos
This backyard offers a serene, partially shaded space with trees, a small patio, and a well-maintained grassy area at 920 Gloriosa Ave, Winter Park, FL 32789
Charming single-story home with a lush front yard, mature trees, and a covered carport showcasing curb appeal at 920 Gloriosa Ave, Winter Park, FL 32789
A well-kept carport with a concrete floor, storage doors, and direct access to the home's entrance at 920 Gloriosa Ave, Winter Park, FL 32789
On Market For 46 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1540

  • Year Built

    1956

  • $/SqFt

    $269

Albert Lee Ridge - This home is a true gem—schedule your private showing today before it’s gone! EXP REALTY LLC.

Home For Sale $399,000

Charming one-story home with a two-car garage and well-maintained lawn at 2828 Whispering Way, Winter Park, FL 32792
View Details 92 Photos
Bright foyer features neutral tile flooring, a coat closet, and natural light at 2828 Whispering Way, Winter Park, FL 32792
Spacious living room with a brick fireplace, ceiling fan, and tile flooring at 2828 Whispering Way, Winter Park, FL 32792
Cozy living room features a brick fireplace, neutral walls, and sunlit windows at 2828 Whispering Way, Winter Park, FL 32792
On Market For 47 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1312

  • Year Built

    1986

  • $/SqFt

    $304

Easy access to 417, 436, and University. TOP VALUE PROPERTIES LLC.

Home For Sale $2,999,000

Reduced By $201,000

Stunning two-story home featuring a brick driveway, lush landscaping, and a welcoming front entrance at 1891 Lake Spier Dr, Winter Park, FL 32789
View Details 34 Photos
Bright living room featuring stylish seating, coffered ceiling, and sliding glass doors overlooking a beautiful lake at 1891 Lake Spier Dr, Winter Park, FL 32789
Open-concept kitchen featuring marble countertops, pendant lighting, and seamless flow into the living space at 1891 Lake Spier Dr, Winter Park, FL 32789
Well-appointed kitchen island with seating, pendant lights, and stylish backsplash at 1891 Lake Spier Dr, Winter Park, FL 32789
On Market For 47 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3932

  • Year Built

    2024

  • $/SqFt

    $763

South Lakemont Shores - Call today to schedule your private showing. LPT REALTY, LLC.

Pended $2,375,000

Charming two-story home featuring a balcony, manicured lawn, and brick accents at 104 Cortland Ave, Winter Park, FL 32789
View Details 65 Photos
Charming two-story home featuring a balcony, manicured lawn, and brick accents at 104 Cortland Ave, Winter Park, FL 32789
Landscaped front yard with manicured hedges, stone walkway, and lush greenery at 104 Cortland Ave, Winter Park, FL 32789
Inviting front entrance with brick columns, landscaped garden, and stone walkway at 104 Cortland Ave, Winter Park, FL 32789
On Market For 43 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3182

  • Year Built

    1926

  • $/SqFt

    $746

Cortland Park - This residence is a compelling blend of character, craftsmanship and contemporary living. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $499,000

Charming home with a welcoming front porch, manicured landscaping, and classic curb appeal at 674 Douglas Ave, Winter Park, FL 32789
View Details 33 Photos
Charming home with a welcoming front porch, manicured landscaping, and classic curb appeal at 674 Douglas Ave, Winter Park, FL 32789
Charming home featuring a blue door, white picket fence, well-manicured landscaping, and a private, fenced driveway at 674 Douglas Ave, Winter Park, FL 32789
Kitchen with granite island, vaulted ceiling, stainless steel appliances, and eating area at 674 Douglas Ave, Winter Park, FL 32789
On Market For 47 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1260

  • Year Built

    1925

  • $/SqFt

    $396

The roof was updated in December 2023, and the air conditioning unit was replaced in 2019, the air-conditioning compressor in 2022, and the water heater in 2019. PREMIER SOTHEBYS INT'L REALTY.

Home For Sale $2,900,000

Stunning home featuring a stone turret, red tile roof, and lush, manicured landscaping at 1401 Green Cove Rd, Winter Park, FL 32789
View Details 77 Photos
Charming two-story home boasts a stone turret, red tile roof and well-maintained lawn at 1401 Green Cove Rd, Winter Park, FL 32789
Beautiful home with a stone turret, red tile roof, two-car garage, and verdant lawn at 1401 Green Cove Rd, Winter Park, FL 32789
Lovely home features a stone archway, balcony, and professionally landscaped front yard at 1401 Green Cove Rd, Winter Park, FL 32789
On Market For 49 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    5416

  • Year Built

    2009

  • $/SqFt

    $535

Camwood - Please see Matterport link for layout of this Beautiful Home. BUCKEYE REALTY LLC.

Home For Sale $1,888,000

Striking two-story home with modern design, manicured lawn, and a spacious two-car garage at 2407 Lafayette Ave, Winter Park, FL 32789
View Details 35 Photos
Charming two-story home boasts a modern design, manicured lawn, and a spacious driveway leading to the two-car garage at 2407 Lafayette Ave, Winter Park, FL 32789
Bright entryway with hardwood floors, modern decor, and a view of the outdoors through a glass door at 2407 Lafayette Ave, Winter Park, FL 32789
Bright office space features hardwood floors, a comfortable seating area, and ample natural light at 2407 Lafayette Ave, Winter Park, FL 32789
On Market For 48 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3133

  • Year Built

    2018

  • $/SqFt

    $603

Fontainebleau - Don’t miss this rare opportunity to own a one-of-a-kind home in one of Central Florida’s premier neighborhoods. FANNIE HILLMAN & ASSOCIATES.

Pended $775,000

Charming two-story home with an attached two-car garage, brick driveway, and lush tropical landscaping at 1151 Wildmeadow Run, Winter Park, FL 32792
View Details 45 Photos
Bright, open-concept living room with soaring ceilings, wood floors, and access to dining area and staircase at 1151 Wildmeadow Run, Winter Park, FL 32792
Elegant dining room featuring a stone accent wall, modern chandelier, and bright natural light at 1151 Wildmeadow Run, Winter Park, FL 32792
Stylish kitchen with white cabinets, quartz countertops, stainless steel appliances, and a breakfast bar at 1151 Wildmeadow Run, Winter Park, FL 32792
On Market For 47 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2196

  • Year Built

    2020

  • $/SqFt

    $353

Meadows At Hawks Crest - Convenience is just a short distance away, with Park Maitland Preschool, Kelly’s Ice Cream and Foxtail Coffee right at the entrance of the neighborhood. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $640,000

Reduced By $10,000

Charming single-story home with a well-manicured lawn and inviting walkway at 1218 Fairway Dr, Winter Park, FL 32792
View Details 24 Photos
Inviting front entrance with well-maintained landscaping and a decorative pergola at 1218 Fairway Dr, Winter Park, FL 32792
Close-up of the front entrance with lush landscaping and modern house number at 1218 Fairway Dr, Winter Park, FL 32792
Open-concept dining area with modern chandelier and seamless flow to kitchen at 1218 Fairway Dr, Winter Park, FL 32792
On Market For 27 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1760

  • Year Built

    1979

  • $/SqFt

    $364

Just steps from the 18th tee box at Winter Park Pines Golf Course and zoned for A-rated Winter Park schools, this home delivers the active, upscale lifestyle you've been searching for. Schedule your private showing today! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $499,900

Reduced By $10,000

Charming single-story home featuring a brick driveway, gray facade and well-maintained lawn at 5338 Tangerine Ave, Winter Park, FL 32792
View Details 37 Photos
Bright living room featuring a modern ceiling fan, recessed lighting, and stylish decor at 5338 Tangerine Ave, Winter Park, FL 32792
Open-concept living area with hardwood floors, modern lighting, and seamless flow at 5338 Tangerine Ave, Winter Park, FL 32792
Bright living room featuring a modern ceiling fan, recessed lighting, and stylish decor at 5338 Tangerine Ave, Winter Park, FL 32792
On Market For 48 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2195

  • Year Built

    1976

  • $/SqFt

    $228

Wrenwood Heights - Don't miss your chance to own this turnkey home with every upgrade imaginable. Schedule your private showing today! CENTURY 21 CARIOTI.

Pended $425,000

Charming single story home featuring manicured lawn and mature trees at 3520 Balsam Dr, Winter Park, FL 32792
View Details 30 Photos
Aerial view of the property with a large, tree-filled lot and a well-maintained lawn at 3520 Balsam Dr, Winter Park, FL 32792
Aerial view of landscaped property highlighting a backyard and concrete driveway at 3520 Balsam Dr, Winter Park, FL 32792
Charming single-story home features a well-manicured front yard and a welcoming entrance at 3520 Balsam Dr, Winter Park, FL 32792
On Market For 30 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1468

  • Year Built

    1965

  • $/SqFt

    $290

Eastbrook - Schedule your appointment to view today! EXP REALTY LLC.

Home For Sale $349,000

Reduced By $40,900

Charming single-story home with a bright blue and white exterior, red door, and well-maintained landscaping at 657 Overspin Dr, Winter Park, FL 32789
View Details 25 Photos
Dining room features light wood floors, dining table with seating for four, and decorative art pieces at 657 Overspin Dr, Winter Park, FL 32789
Spacious living room features light wood floors, a comfortable couch, and a decorative rug at 657 Overspin Dr, Winter Park, FL 32789
Bright living room with large windows, comfortable seating, and a stylish round coffee table at 657 Overspin Dr, Winter Park, FL 32789
On Market For 48 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1349

  • Year Built

    1955

  • $/SqFt

    $259

Dubsdread Heights - RE/MAX 200 REALTY.

Pended $995,000

Reduced By $105,000

Charming home featuring a two-car garage, solar panels, and well-manicured landscaping with a spacious driveway at 1821 Windsor Dr, Winter Park, FL 32789
View Details 66 Photos
Attractive home showcasing solar panels, a spacious driveway, and a manicured lawn with tasteful landscaping at 1821 Windsor Dr, Winter Park, FL 32789
Inviting home exterior highlighting a two-car garage, stone accents, and landscaped garden with a paved walkway at 1821 Windsor Dr, Winter Park, FL 32789
Welcoming front porch with stone pillars, stylish seating, and a contemporary front door, creating curb appeal at 1821 Windsor Dr, Winter Park, FL 32789
On Market For 49 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2188

  • Year Built

    2017

  • $/SqFt

    $455

It's a One-of-a-Kind Home! Book your appointment today! CREEGAN GROUP.

Home For Sale $3,150,000

Elegant white two-story home with symmetrical windows, shutters, and landscaped front yard at 541 W Canton Ave, Winter Park, FL 32789
View Details 49 Photos
Stunning white two-story home featuring symmetrical design, shuttered windows, and a charming brick pathway at 541 W Canton Ave, Winter Park, FL 32789
Bright dining room featuring a chandelier, light pink walls, and glass doors leading to the patio at 541 W Canton Ave, Winter Park, FL 32789
Elegant dining room with modern chandelier, farm table, and glass doors to the outside at 541 W Canton Ave, Winter Park, FL 32789
On Market For 52 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3553

  • Year Built

    2024

  • $/SqFt

    $887

This masterpiece set in the heart of Winter Park, thoughtfully surrounded by lush landscaping and carefully placed privacy screens, offers polish and presence in the perfect location. KELLER WILLIAMS WINTER PARK.

Home For Sale $999,000

Reduced By $101,000

Charming two-story home with a two-car garage, black trim, and mature trees offering ample shade at 913 Moss Ln, Winter Park, FL 32789
View Details 38 Photos
Aerial view of the home nestled among mature trees with a large, fenced backyard at 913 Moss Ln, Winter Park, FL 32789
Two story home with a two car garage, a long driveway, and mature shade trees at 913 Moss Ln, Winter Park, FL 32789
Two-story home with a 2-car garage, dark trim and a concrete driveway at 913 Moss Ln, Winter Park, FL 32789
On Market For 53 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1887

  • Year Built

    1953

  • $/SqFt

    $529

Maitland Shores - Don’t let this rare opportunity slip away—913 Moss Lane is your chance to own a fully updated masterpiece, so schedule your exclusive showing now and step into the life you’ve always dreamed of—call today before this gem is gone! VECTOR PROPERTY GROUP.

Home For Sale $775,000

Two-story home with paver driveway, grey siding, clay tile roof, and manicured landscaping at 1340 Blue Stem Ln, Winter Park, FL 32792
View Details 20 Photos
Angle view of two-story home showcasing white trim, grey siding, and desert landscaping at 1340 Blue Stem Ln, Winter Park, FL 32792
Bright kitchen with white cabinets, stainless steel appliances, and bar seating at 1340 Blue Stem Ln, Winter Park, FL 32792
Open kitchen design with quartz countertops, stainless steel appliances, and bar seating at 1340 Blue Stem Ln, Winter Park, FL 32792
On Market For 53 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2587

  • Year Built

    2022

  • $/SqFt

    $300

Hawks Crest - Ideally located near top-rated schools, shopping, and dining—schedule your tour today! AGL BROKERAGE CORP.

Home For Sale $3,600,000

Stunning two-story home featuring a modern design, three-car garage, and beautifully landscaped front yard at 182 N Phelps Ave, Winter Park, FL 32789
View Details 57 Photos
Beautifully landscaped two-story home with a three-car garage and modern architectural design at 182 N Phelps Ave, Winter Park, FL 32789
Two-story home with three-car garage, modern architectural design, landscaped front yard, and paver driveway at 182 N Phelps Ave, Winter Park, FL 32789
Exterior home featuring a modern design, three-car garage, and illuminated architectural details at twilight at 182 N Phelps Ave, Winter Park, FL 32789
On Market For 46 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    4812

  • Year Built

    2025

  • $/SqFt

    $748

Golfview - In conclusion, the home exhibits a smooth blend of advanced technology and high-end finishes, promising a luxurious living experience! LA ROSA REALTY HORIZONS LLC.

Pended $2,495,000

Reduced By $855,000

Beautiful home featuring a winding brick drive, lush landscaping, and a second-story balcony, offering great curb appeal at 940 Lincoln Cir, Winter Park, FL 32789
View Details 81 Photos
Stunning white home with manicured landscaping, a metal roof, and a second-story balcony offers luxurious curb appeal at 940 Lincoln Cir, Winter Park, FL 32789
Charming home entrance featuring manicured shrubs, a brick pathway, and covered porch at 940 Lincoln Cir, Winter Park, FL 32789
Charming porch with seating area overlooking lush landscape at 940 Lincoln Cir, Winter Park, FL 32789
On Market For 51 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3551

  • Year Built

    1995

  • $/SqFt

    $703

A rare opportunity in Winter Park’s most walkable and desirable neighborhood. KELLY PRICE & COMPANY LLC.

Home For Sale $1,625,000

Reduced By $174,000

Charming home with well-manicured lawn and pathway leading to the front door, shaded by mature trees at 1742 Barcelona Way, Winter Park, FL 32789
View Details 62 Photos
Inviting home exterior showcasing a lush lawn and brick driveway framed by mature trees and landscaping at 1742 Barcelona Way, Winter Park, FL 32789
Charming home with well-manicured lawn and pathway leading to the front door, shaded by mature trees at 1742 Barcelona Way, Winter Park, FL 32789
Home exterior with lush lawn, mature trees, and a brick pathway leading to the front entrance at 1742 Barcelona Way, Winter Park, FL 32789
On Market For 53 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    3626

  • Year Built

    1973

  • $/SqFt

    $448

This one-of-a-kind estate home is truly special and a must-see. KELLY PRICE & COMPANY LLC.

Home For Sale $299,000

Reduced By $16,000

Charming single-story home featuring a cozy front porch and well-maintained lawn with mature trees at 849 Driver Ave, Winter Park, FL 32789
View Details 31 Photos
Inviting home exterior showcases a small front porch, attached garage, and a lush green lawn at 849 Driver Ave, Winter Park, FL 32789
Aerial view of single-story home featuring a small front porch, attached garage, and well-maintained lawn at 849 Driver Ave, Winter Park, FL 32789
Bright sun room with large windows offering plenty of natural light and pleasant outdoor views at 849 Driver Ave, Winter Park, FL 32789
On Market For 42 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    894

  • Year Built

    1957

  • $/SqFt

    $334

Dubsdread Heights - Don’t miss out—schedule your showing today! CASTLE & COTTAGE REALTY LLC.

Home For Sale $3,595,000

Reduced By $385,000

Elegant two-story home featuring lush landscaping and a classic architectural design at 141 S Phelps Ave, Winter Park, FL 32789
View Details 60 Photos
Beautiful home exterior with stone pillar, lush landscaping, and mature trees at 141 S Phelps Ave, Winter Park, FL 32789
Covered outdoor living space with a built-in kitchen, comfortable seating, and pool view at 141 S Phelps Ave, Winter Park, FL 32789
Inviting backyard pool area surrounded by lush landscaping and patio seating at 141 S Phelps Ave, Winter Park, FL 32789
On Market For 53 Days

  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    5878

  • Year Built

    2006

  • $/SqFt

    $612

Windsong Lakeside - Don't miss the opportunity to own this spectacular home in one of Winter Park's most sought after neighborhoods with its top-rated schools, and proximity to shopping and dining on Park Avenue in picturesque downtown Winter Park! COLDWELL BANKER RESIDENTIAL RE.

Pended $485,000

Charming single-story home featuring a well-manicured lawn and a welcoming front porch with blue door at 417 Carvell Dr, Winter Park, FL 32792
View Details 51 Photos
Inviting single-story home with lush green lawn and covered porch, featuring a striking blue front door at 417 Carvell Dr, Winter Park, FL 32792
Exterior of home with green lawn and mailbox in front, a blue front door with glass and house number above at 417 Carvell Dr, Winter Park, FL 32792
Home exterior featuring a covered porch, well-kept lawn, and landscaped front yard in a beautiful neighborhood at 417 Carvell Dr, Winter Park, FL 32792
On Market For 53 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1823

  • Year Built

    1958

  • $/SqFt

    $266

Winter Park Estates - Don’t miss your chance to own this move-in-ready, eco-conscious home in the heart of Winter Park. Schedule your private showing today! KELLER WILLIAMS WINTER PARK.

Pended $430,000

Reduced By $10,000

Charming single-story brick home featuring a well-manicured front yard and attached two car garage at 7249 Abbey Ln, Winter Park, FL 32792
View Details 29 Photos
Inviting one-story brick home showcasing a cozy front porch and a lush green landscape at 7249 Abbey Ln, Winter Park, FL 32792
Aerial view of home featuring a backyard pool surrounded by mature trees and landscaping at 7249 Abbey Ln, Winter Park, FL 32792
Bright and airy living room featuring neutral tile flooring and an open layout to the kitchen at 7249 Abbey Ln, Winter Park, FL 32792
On Market For 54 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1508

  • Year Built

    1983

  • $/SqFt

    $285

Oakcrest - Come invest in your future and make this charming house your dream home. RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $1,695,000

Stunning two-story modern home with stone accents and a spacious three-car garage at 1831 Mizell Ave, Winter Park, FL 32789
View Details 40 Photos
Inviting front entrance with stylish door, stone accents, and manicured landscaping at 1831 Mizell Ave, Winter Park, FL 32789
Contemporary two-story home boasts striking stone accents and a three-car garage at 1831 Mizell Ave, Winter Park, FL 32789
Bright and modern foyer with hardwood floors, glass-railed staircase, and elegant lighting at 1831 Mizell Ave, Winter Park, FL 32789
On Market For 55 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3204

  • Year Built

    2016

  • $/SqFt

    $529

Zoned for A-rated Brookshire Elementary, Glenridge Middle, and Winter Park High School. MORE PICTURES FRIDAY! EXP REALTY LLC.

Pended $777,000

Reduced By $12,000

Charming single-Gathering home featuring a two-car garage, stone accents, and professionally landscaped front yard at 2159 Marsh Sedge Ln, Winter Park, FL 32792
View Details 50 Photos
Charming single-Gathering home featuring a two-car garage, stone accents, and professionally landscaped front yard at 2159 Marsh Sedge Ln, Winter Park, FL 32792
Expansive aerial view of single-Gathering homes in a well-maintained suburban neighborhood at 2159 Marsh Sedge Ln, Winter Park, FL 32792
Lovely aerial view of homes nestled in a lush green community with a scenic lake nearby at 2159 Marsh Sedge Ln, Winter Park, FL 32792
On Market For 55 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2192

  • Year Built

    2019

  • $/SqFt

    $354

Preserve At Hawks Crest - This spectacular home – schedule your showing today! KELLER WILLIAMS REALTY AT THE PARKS.

Pended $434,900

Reduced By $15,100

Charming single-story home with a two-car garage and mature landscaping at 1985 Japonica Rd, Winter Park, FL 32792
View Details 16 Photos
An empty room showcases dark wood flooring and neutral walls at 1985 Japonica Rd, Winter Park, FL 32792
Bright living room featuring tile flooring, a window, and a neutral color scheme at 1985 Japonica Rd, Winter Park, FL 32792
Bright living room with tile flooring, a ceiling fan, and sliding glass doors to outdoor space at 1985 Japonica Rd, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 54 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2096

  • Year Built

    1972

  • $/SqFt

    $207

Winter Woods - If location is everything then this one is PERFECT just minutes from shopping, entertainment, schools, restaurants, hospital and major streets. Please call to schedule today! MIGHTY REALTY INC.

Home For Sale $520,000

Reduced By $30,000

Charming single-story home with a well-maintained yard and inviting curb appeal at 1809 Pineview Cir, Winter Park, FL 32792
View Details 32 Photos
Bright, open kitchen featuring stainless steel appliances and a granite countertop breakfast bar at 1809 Pineview Cir, Winter Park, FL 32792
Inviting backyard with fire pit, mature trees, a hammock, and an entertainment deck at 1809 Pineview Cir, Winter Park, FL 32792
Modern bathroom with glass-enclosed shower, tiled floors, and a bright vanity at 1809 Pineview Cir, Winter Park, FL 32792
On Market For 57 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1631

  • Year Built

    1956

  • $/SqFt

    $319

Lakemont Heights - Don’t miss the chance to make this well-maintained home your own. CHARLES RUTENBERG REALTY ORLANDO.

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