325 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $1,250,000

Exterior of a tan home showing the yard with green grass, driveway, and manicured bushes at 4052 Gilder Rose Pl, Winter Park, FL 32792
Lovely exterior of a two story home featuring manicured landscaping, an arched entrance, and a grey tile roof at 4052 Gilder Rose Pl, Winter Park, FL 32792
Bright and spacious foyer with a grand staircase, soaring ceilings, and large windows overlooking the backyard at 4052 Gilder Rose Pl, Winter Park, FL 32792
On Market Today
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4015

  • Year Built

    1995

  • $/SqFt

    $311

Call for your private tour today! HOMEVEST REALTY.

Home For Sale $645,000

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 2 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 $579,900

Inviting single-story home with stone accents, green lawn, and mature trees, offering great curb appeal at 7679 Bent Bow Trl, Winter Park, FL 32792
Covered carport featuring stone accent wall, updated lighting, and access to the main residence at 7679 Bent Bow Trl, Winter Park, FL 32792
Enclosed carport with white walls and a decorative stone accent wall at 7679 Bent Bow Trl, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market Today
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2616

  • Year Built

    1971

  • $/SqFt

    $222

Call today for a private showing. GILKEY REAL ESTATE.

Home For Sale $2,349,000

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 3 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3558

  • Year Built

    2005

  • $/SqFt

    $660

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 $475,000

Open-concept living room featuring hardwood floors, neutral paint, and arched doorways leading to other rooms at 3304 Bennington Ct, Winter Park, FL 32792
Bright living room with hardwood floors and sliding glass doors leading to the outdoor patio at 3304 Bennington Ct, Winter Park, FL 32792
Spacious living room featuring hardwood floors, neutral paint, and an open layout at 3304 Bennington Ct, Winter Park, FL 32792
On Market For 2 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1804

  • Year Built

    2003

  • $/SqFt

    $263

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

Home For Sale $449,000

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
Modern kitchen with stainless steel appliances, white cabinets, and a stylish backsplash at 1842 Puritan Ave, Winter Park, FL 32792
On Market For 2 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1836

  • Year Built

    1963

  • $/SqFt

    $245

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

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 4 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
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 4 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.

Home For Sale $369,900

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 3 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

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 5 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 $2,100,000

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 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2674

  • Year Built

    1968

  • $/SqFt

    $785

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 $1,594,950

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 5 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    3474

  • Year Built

    2008

  • $/SqFt

    $459

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

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 5 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.

Home For Sale $430,000

Inviting single-Gathering home with a lush lawn and a classic design surrounded by trees and a white fence at 5210 Poinsetta Ave, Winter Park, FL 32792
Modern kitchen featuring gray cabinets, stainless steel appliances, and a black backsplash at 5210 Poinsetta Ave, Winter Park, FL 32792
Bright kitchen with stainless steel appliances, large island, and pendant lighting at 5210 Poinsetta Ave, Winter Park, FL 32792
On Market For 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1476

  • Year Built

    1974

  • $/SqFt

    $291

Wrenwood Heights - Discover your perfect Florida haven today! REAL BROKER, LLC.

Home For Sale $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
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 5 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

Elegant living room features a fireplace, stylish decor, and comfortable seating at 185 Sylvan Blvd, Winter Park, FL 32789
Spacious kitchen with modern appliances, an island with seating, and hardwood floors at 185 Sylvan Blvd, Winter Park, FL 32789
Inviting bedroom with large windows, a comfortable bed, and stylish decor at 185 Sylvan Blvd, Winter Park, FL 32789
On Market For 6 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

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 6 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

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 6 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.

Home For Sale $599,000

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 6 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.

Home For Sale $1,749,000

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 9 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3379

  • Year Built

    2005

  • $/SqFt

    $518

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

Home For Sale $625,000

Bright living room with tile flooring, stylish furnishings, and modern decor, ideal for relaxing or entertaining at 2524 Sweetwater Trl, Winter Park, FL 32789
Open-concept living room featuring hardwood floors, neutral paint, and ample natural light, perfect for Gathering gatherings at 2524 Sweetwater Trl, Winter Park, FL 32789
Spacious living room offering hardwood floors and a billiard table to be enjoyed by Gathering and friends at 2524 Sweetwater Trl, Winter Park, FL 32789
On Market For 8 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1728

  • Year Built

    1965

  • $/SqFt

    $362

Extras include: 2 car garage, irrigation system with well, tile & laminate flooring throughout, NO HOA!, Fantastic neighborhood in a great location!! WELCOME HOME! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $510,000

Reduced By $10,000

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 8 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 $299,995

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 10 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    818

  • Year Built

    1938

  • $/SqFt

    $367

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

Home For Sale $1,999,900

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 9 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

Lush front entrance with tropical landscaping leads to a welcoming doorway at 4107 Gabriella Ln, Winter Park, FL 32792
Two-story home with wood deck, surrounded by lush greenery and mature trees in a secluded setting at 4107 Gabriella Ln, Winter Park, FL 32792
Beautiful screened-in pool with a rock waterfall and lush greenery, great for outdoor entertainment at 4107 Gabriella Ln, Winter Park, FL 32792
On Market For 11 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 $485,000

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 9 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1939

  • Year Built

    1973

  • $/SqFt

    $250

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

Home For Sale $420,000

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 10 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1540

  • Year Built

    1956

  • $/SqFt

    $273

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

Pended $420,000

Inviting single-story home showcasing a well-manicured lawn and a convenient two-car garage at 1301 Paradise Ln, Winter Park, FL 32792
Expansive backyard featuring lush lawn, a screened patio and a classic wooden fence at 1301 Paradise Ln, Winter Park, FL 32792
Open-concept living room with modern furnishings, hardwood floors, and a view of the kitchen and backyard at 1301 Paradise Ln, Winter Park, FL 32792
On Market For 10 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1379

  • Year Built

    1984

  • $/SqFt

    $305

Never lived in since its complete overhaul, this is a one-of-a-kind opportunity to own a move-in ready home that delivers at every level. Book a private tour today. COMPASS FLORIDA LLC.

Home For Sale $399,000

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 11 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 $3,200,000

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 11 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3932

  • Year Built

    2024

  • $/SqFt

    $814

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

Home For Sale $2,375,000

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 11 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
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 11 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

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 12 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

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 12 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 $849,900

Bright and airy living room featuring hardwood floors, exposed beam, and an open floor plan at 1791 Spruce Ave, Winter Park, FL 32789
Cozy living room boasts hardwood floors, natural light, and an open layout with an eat-in kitchen at 1791 Spruce Ave, Winter Park, FL 32789
Inviting living room featuring hardwood floors, neutral colors, and an open layout with a kitchen at 1791 Spruce Ave, Winter Park, FL 32789
On Market For 11 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1776

  • Year Built

    1956

  • $/SqFt

    $479

Conwill Estates - Don't miss this opportunity to own a home where thoughtful, high quality upgrades meet elegant living in one of Winter Park’s most desirable neighborhoods. KELLER WILLIAMS WINTER PARK.

Home For Sale $775,000

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 13 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 $650,000

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 11 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1760

  • Year Built

    1979

  • $/SqFt

    $369

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 $509,900

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 11 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2195

  • Year Built

    1976

  • $/SqFt

    $232

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

Home For Sale $425,000

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 12 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1468

  • Year Built

    1965

  • $/SqFt

    $290

Eastbrook - SEE MORE IN VIDEO TOUR VIDEO --> WWW.TINYURL.COM/3520BalsamDr EXP REALTY LLC.

Home For Sale $389,900

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 12 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1349

  • Year Built

    1955

  • $/SqFt

    $289

Dubsdread Heights - RE/MAX 200 REALTY.

Home For Sale $1,100,000

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 13 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2188

  • Year Built

    2017

  • $/SqFt

    $503

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

Home For Sale $3,150,000

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 16 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 $1,100,000

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 2-car garage, dark trim and a concrete driveway 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 17 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1887

  • Year Built

    1953

  • $/SqFt

    $583

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

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 17 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.

Pended $4,599,000

Aerial view of an inviting backyard with a sparkling pool, lounge chairs, and an outdoor seating area at 985 Lincoln Cir, Winter Park, FL 32789
Home to be professionally photographed. Photos to be uploaded by May 20 at 985 Lincoln Cir, Winter Park, FL 32789
On Market For 16 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3660

  • Year Built

    1951

  • $/SqFt

    $1,257

Inquire with agent for more information. UNITED REAL ESTATE PREFERRED.

Home For Sale $3,600,000

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 17 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.

Home For Sale $3,095,000

Reduced By $255,000

Beautiful two-story house showcasing manicured landscaping, balcony, and curved brick path at 940 Lincoln Cir, Winter Park, FL 32789
Attractive two-story home showcasing manicured landscaping, balcony, and curved brick path 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
On Market For 17 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3551

  • Year Built

    1995

  • $/SqFt

    $872

Thoughtfully designed and meticulously maintained, this turnkey home blends architectural charm with modern comfort—just a short walk from Park Avenue. KELLY PRICE & COMPANY LLC.

Home For Sale $1,799,000

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 17 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    3626

  • Year Built

    1973

  • $/SqFt

    $496

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

Home For Sale $400,000

Open-concept living room featuring tile floors, modern ceiling fan, and a comfortable leather sofa at 5234 Ohio St, Winter Park, FL 32792
Inviting living room with two leather couches, tile floors, and natural light from large windows at 5234 Ohio St, Winter Park, FL 32792
Cozy room with easy access to pool through french doors, a sleek ceiling fan, and tiled floors at 5234 Ohio St, Winter Park, FL 32792
On Market For 17 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1226

  • Year Built

    1973

  • $/SqFt

    $326

EXP REALTY LLC.

Home For Sale $315,000

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 17 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    894

  • Year Built

    1957

  • $/SqFt

    $352

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

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 407-485-1814 and speak with one of our real estate consultants.

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