172 Results

32789 Homes For Sale & 32789 FL Real Estate

Home For Sale $3,599,999

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

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 For 2 Days
  • 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 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 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 For 2 Days
  • 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

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 $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
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 For 2 Days
  • 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 $1,500,000

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 5 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 $825,000

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 5 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

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 5 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 $949,900

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 6 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 $775,000

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 7 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 $2,399,000

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 9 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 $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
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 10 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.

Pended $1,200,000

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 8 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

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 11 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 $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
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 12 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

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 7 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 $1,300,000

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 13 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 $269,000

Reduced By $30,000

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 $779,000

On Market For 6 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

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 $4,175,000

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 18 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.

Home For Sale $1,599,000

Charming exterior with lush green lawn, brick driveway, and meticulous landscaping at 1327 Bridgeport Dr, Winter Park, FL 32789
Beautiful backyard oasis with a sparkling pool, brick patio, and poolside seating at 1327 Bridgeport Dr, Winter Park, FL 32789
Inviting freeform pool area, surrounded by lush landscaping and serene privacy at 1327 Bridgeport Dr, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 17 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4181

  • Year Built

    1979

  • $/SqFt

    $382

Waterbridge - Move right in, everything has been done. RE/MAX TOWN & COUNTRY REALTY.

Pended $675,000

Inviting single-story house with a well-kept front yard and ample parking space at 1511 Chestnut Ave, Winter Park, FL 32789
Welcoming front porch with a cozy seating area and an orange front door at 1511 Chestnut Ave, Winter Park, FL 32789
Charming front porch featuring tiled flooring, white columns, and a peaceful view at 1511 Chestnut Ave, Winter Park, FL 32789
On Market For 17 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1275

  • Year Built

    1960

  • $/SqFt

    $529

Lake Knowles Terrace - Don’t miss your chance to become part of the Winter Park lifestyle! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $559,000

Reduced By $10,000

Expansive backyard featuring lush green grass and a privacy fence, offering ample space for outdoor activities at 240 Cambridge Blvd, Winter Park, FL 32789
Aerial view of a property showcasing its location within a neighborhood and proximity to a serene lake at 240 Cambridge Blvd, Winter Park, FL 32789
Bright living room features neutral decor, two sofas, two windows, and a modern entertainment center at 240 Cambridge Blvd, Winter Park, FL 32789
On Market For 17 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1630

  • Year Built

    1950

  • $/SqFt

    $343

Glencoe - Don’t miss this opportunity to own a move-in-ready gem in the heart of Winter Park. Schedule your private showing today! REAL BROKER, LLC.

Pended $530,000

Inviting home featuring a lush green lawn, mature trees, and a convenient driveway for easy access at 2525 Lafayette Ave, Winter Park, FL 32789
Beautifully landscaped front yard with a well-maintained lawn and easy street access at 2525 Lafayette Ave, Winter Park, FL 32789
Bright living room with beautiful wood floors, a large window, and ample natural light at 2525 Lafayette Ave, Winter Park, FL 32789
On Market For 16 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    817

  • Year Built

    1956

  • $/SqFt

    $649

Winter Park Village - Value is in the land. Schedule your showing today! KELLER WILLIAMS WINTER PARK.

Home For Sale $8,500,000

A stately home featuring a circular driveway, manicured landscaping, and symmetrical design elements at 1112 Preserve Point Dr, Winter Park, FL 32789
Elegant exterior of a home with landscaped grounds, featuring a circular driveway and beautiful architectural lighting at 1112 Preserve Point Dr, Winter Park, FL 32789
View of an elegant home, framed by mature trees, with a large circular driveway and landscaped entrance at 1112 Preserve Point Dr, Winter Park, FL 32789
On Market For 17 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6502

  • Year Built

    2013

  • $/SqFt

    $1,307

Windsong Preserve Point - Showings are by appointment only for qualified buyers. KELLY PRICE & COMPANY LLC.

Home For Sale $924,900

Reduced By $24,100

On Market For 18 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1314

  • Year Built

    1949

  • $/SqFt

    $704

Charmont - Seller is related to listing broker. RAZZANI INTERNATIONAL REALTY.

Pended $1,899,000

Inviting two-story home featuring manicured landscaping and stone walkway to front door, with a second story balcony at 1665 Temple Dr, Winter Park, FL 32789
Beautiful two-story home features lush landscaping, paver driveway, wood garage door covered by greenery, and balcony at 1665 Temple Dr, Winter Park, FL 32789
Paver driveway leading to garage featuring mature landscaping and charming vines climbing the front entrance at 1665 Temple Dr, Winter Park, FL 32789
On Market For 17 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3830

  • Year Built

    2007

  • $/SqFt

    $496

Woodmere Terrace - Don’t miss your chance to own a home that offers exceptional space, stylish design, and one of the most desirable locations in Winter Park. COMPASS FLORIDA LLC.

Pended $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 18 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 $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 24 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 $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 25 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
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 25 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 $1,594,950

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 25 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 $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 26 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 26 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 27 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
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 26 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

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 29 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 $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 29 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1728

  • Year Built

    1965

  • $/SqFt

    $362

* Located in one of the most sought-after neighborhoods in Winter Park—this is the home you’ve been waiting for. WELCOME HOME! FANNIE HILLMAN & ASSOCIATES.

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 19 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 29 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 $414,999

Reduced By $5,001

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 30 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 $3,150,000

Reduced By $50,000

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 31 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3932

  • Year Built

    2024

  • $/SqFt

    $801

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 31 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 31 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 32 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 32 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.

Home For Sale $369,000

Reduced By $20,900

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 31 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1349

  • Year Built

    1955

  • $/SqFt

    $274

Dubsdread Heights - RE/MAX 200 REALTY.

Pended $995,000

Reduced By $105,000

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 33 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.

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.

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