143 Results

32789 Homes For Sale & 32789 FL Real Estate

Home For Sale $675,000

Stylish two-story townhouse showcasing a well-manicured yard and inviting curb appeal at 796 Mcintyre Ave, Winter Park, FL 32789
Welcoming front entryway with a decorative red door and attractive landscaping at 796 Mcintyre Ave, Winter Park, FL 32789
Quiet street view showcasing beautiful brick-paved road and mature trees at 796 Mcintyre Ave, Winter Park, FL 32789
On Market For 3 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1910

  • Year Built

    1988

  • $/SqFt

    $353

Zoned for Audubon K-8 and Winter Park High School. Welcome home! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $500,000

Bungalow-style home featuring a screened porch, driveway, and established landscaping at 2011 Harmon Ave, Winter Park, FL 32789
Aerial view of the property showing the backyard, landscaping, and surrounding neighborhood at 2011 Harmon Ave, Winter Park, FL 32789
On Market For 4 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1699

  • Year Built

    1925

  • $/SqFt

    $294

Lawndale - Property being sold for lot value. 100 x 140. Zoned R2. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,490,000

Inviting home exterior with brick path and blooming flowering trees at 1299 Harding Street, Winter Park, FL 32789
Spacious living room with hardwood floors, fireplace, and built-in shelving at 1299 Harding Street, Winter Park, FL 32789
Open living space with hardwood floors, large sofa, and ample natural light at 1299 Harding Street, Winter Park, FL 32789
On Market For 5 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3784

  • Year Built

    1951

  • $/SqFt

    $658

Kronenberger - Located just steps from the 5-acre Kraft Azalea Garden with lakefront trails and a fishing dock, and a short stroll to Park Avenue to enjoy a scenic boat tour or one of the many museums—this is a truly exceptional offering in one of Winter Park’s most sought-after enclaves. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $675,000

Covered carport area, offering protection from the elements and decorated with potted plants and grilling area at 3019 Northwood Blvd, Winter Park, FL 32789
Inviting entryway with classic furnishings and art, leading to the home's interior spaces at 3019 Northwood Blvd, Winter Park, FL 32789
Comfortable living area featuring retro furniture and decor, offering a cozy and inviting space at 3019 Northwood Blvd, Winter Park, FL 32789
On Market For 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1662

  • Year Built

    1953

  • $/SqFt

    $406

Northwood Terrace - 2 Car Carport. Value is in the land. SAND DOLLAR REALTY GROUP INC.

Home For Sale $569,000

Charming light blue single story home with a well manicured front yard and walkway to the front door at 1368 Devon Rd, Winter Park, FL 32789
Spacious living room with beautiful parquet flooring, large sofa, ceiling fans, and dining area visible at 1368 Devon Rd, Winter Park, FL 32789
Spacious living room and dining area with beautiful parquet flooring and modern ceiling fans at 1368 Devon Rd, Winter Park, FL 32789
On Market For 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1642

  • Year Built

    1952

  • $/SqFt

    $347

Orwin Manor - Call for your private showing today! LPT REALTY, LLC.

Home For Sale $450,000

Charming home featuring a dark green exterior, metal roof, fenced yard and white window awnings at 710 W Swoope W Ave, Winter Park, FL 32789
Spacious backyard with a small storage shed, perfect for outdoor activities and entertaining at 710 W Swoope W Ave, Winter Park, FL 32789
Spacious backyard featuring green grass and view of the back of house with screened in back porch at 710 W Swoope W Ave, Winter Park, FL 32789
On Market For 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    960

  • Year Built

    1950

  • $/SqFt

    $469

Bungalow with metal roof approximately one block from Winter Park mall. Considered an excellent location. FIRMAN A. EMANUEL.

Home For Sale $4,100,000

Charming home with a well-manicured lawn and a classic facade, perfect for suburban living at 1782 Pine Ave, Winter Park, FL 32789
Backyard featuring a refreshing pool, lush lawn, perfect for relaxation and entertainment at 1782 Pine Ave, Winter Park, FL 32789
Detailed floor plan showcasing spacious layout with multiple bedrooms, living areas, and garages at 1782 Pine Ave, Winter Park, FL 32789
On Market For 6 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4782

  • Year Built

    2025

  • $/SqFt

    $857

Conwill Estates - Interlachen Golf community less than 5 min, Park Ave 10 min and restaurant and retail minutes away. Schedule your private tour today. EXP REALTY LLC.

Home For Sale $1,349,000

Spacious home featuring a three-car garage and manicured landscaping at 1077 Minnesota Ave, Winter Park, FL 32789
Three-car garage featuring white doors at 1077 Minnesota Ave, Winter Park, FL 32789
Spacious home with a two-car garage and exterior paint touch ups in progress at 1077 Minnesota Ave, Winter Park, FL 32789
On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3046

  • Year Built

    2025

  • $/SqFt

    $443

Don’t miss your opportunity to own a statement home that offers both sophistication and lifestyle. Private tours available by appointment. SHORES REAL ESTATE.

Home For Sale $2,199,000

Charming one-story home with dormer windows, covered entryway, and manicured landscaping at 1394 Stewart St, Winter Park, FL 32789
Well-maintained single-story home with lush landscaping and mature trees on an expansive lawn at 1394 Stewart St, Winter Park, FL 32789
Spacious living room with brick fireplace, hardwood floors, and natural light at 1394 Stewart St, Winter Park, FL 32789
On Market For 7 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3907

  • Year Built

    1961

  • $/SqFt

    $563

Residents feel a deep sense of pride and belonging, while visitors are drawn to the charm and warmth that define our town. REALTY ONE GROUP INSPIRATION.

Home For Sale $799,999

On Market For 7 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1128

  • Year Built

    1952

  • $/SqFt

    $709

Lake Forest Park - Demo cost to be included in the purchase price. BALDWIN PARK REALTY LLC.

Home For Sale $375,000

Two-story tan home with a single car garage and mature shade trees at 156 Oak Grove Rd, Winter Park, FL 32789
Aerial view of a home with fenced backyard and mature trees at 156 Oak Grove Rd, Winter Park, FL 32789
Open concept Living Room with ceiling fan and tile floors at 156 Oak Grove Rd, Winter Park, FL 32789
On Market For 10 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1456

  • Year Built

    1995

  • $/SqFt

    $258

Don’t miss this exceptional opportunity—schedule your private showing today! EVERLANE REALTY LLC.

Pended $1,395,000

Inviting entryway showcasing a wood front door with decorative wreath, framed by trimmed hedges and a brick walkway at 1633 Pine Ave, Winter Park, FL 32789
Open-concept living area with hardwood floors, view of the kitchen, and neutral decor perfect for relaxing or entertaining at 1633 Pine Ave, Winter Park, FL 32789
Cozy bedroom with hardwood floors, natural light, and built-in bookcase with a quiet spot to read and unwind at 1633 Pine Ave, Winter Park, FL 32789
On Market For 11 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2481

  • Year Built

    1951

  • $/SqFt

    $562

Lake Knowles Terrace - It's walking distance to Phelps Park and just a short drive to the charming shops and dining on Park Avenue. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $675,000

Inviting home exterior featuring a manicured lawn and a covered carport with a paved driveway at 843 W Swoope Ave, Winter Park, FL 32789
Inviting front entrance with manicured lawn and stone walkway leading to a stylish front door at 843 W Swoope Ave, Winter Park, FL 32789
Quaint home exterior with dark trim and convenient carport in a lush, green setting at 843 W Swoope Ave, Winter Park, FL 32789
On Market For 11 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1232

  • Year Built

    1962

  • $/SqFt

    $548

Request your private showing today and make the move to Winter Park. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $595,000

Inviting living room with hardwood floors, plenty of natural light, and comfortable seating, ideal for relaxation at 1230 N Denning Dr, Winter Park, FL 32789
Spacious living room featuring hardwood floors, a stylish area rug, and plenty of room for entertaining guests at 1230 N Denning Dr, Winter Park, FL 32789
Bright and airy living room with an open layout, hardwood flooring, and comfortable furnishings creating a welcoming space at 1230 N Denning Dr, Winter Park, FL 32789
On Market For 11 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    972

  • Year Built

    1952

  • $/SqFt

    $612

Dixie Terrace - The homes proximity to The Winter Park Cultural Corridor which includes Rollins College, The Morse Museum, The Scenic Boat Tour, and The Farmer’s Market make this a most sought-after location. Schedule your private showing today! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $3,250,000

Beautiful two-story home with a brick driveway, lush landscaping, and classic architectural details at 266 Chase Ave, Winter Park, FL 32789
Stunning two-story white home with manicured landscaping, mature trees, and brick driveway at 266 Chase Ave, Winter Park, FL 32789
Elegant front door with sidelights and a hanging lantern, framed by manicured hedges at 266 Chase Ave, Winter Park, FL 32789
On Market For 12 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4088

  • Year Built

    1930

  • $/SqFt

    $795

This is more than just a home, it’s a lifestyle and a rare chance to own one of Winter Park’s rare downtown area treasured properties. PREMIER SOTHEBY'S INTL. REALTY.

Pended $550,000

Backyard pool surrounded by a brick border and a wooden fence at 2906 Rapidan Trl, Winter Park, FL 32789
Entryway with parquet floors, decorative shuttered window, and a long hallway leading to the living areas at 2906 Rapidan Trl, Winter Park, FL 32789
Bright living room featuring a fireplace, neutral walls, and ample space at 2906 Rapidan Trl, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 11 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2326

  • Year Built

    1965

  • $/SqFt

    $236

), Hvac 2010, Electrical - 2022 **we Are Accepting Any And All Offers Through 9am Monday April 7, 2025. *** KELLER WILLIAMS WINTER PARK.

Home For Sale $549,000

Exterior view of home with mature trees, landscaping, and a gray truck in the driveway at 2464 Lotafun Ave, Winter Park, FL 32789
Exterior view of home with mature trees, landscaping, and a gray truck in the driveway at 2464 Lotafun Ave, Winter Park, FL 32789
View of the driveway and carport, featuring a truck, trailer, and mature trees around the property at 2464 Lotafun Ave, Winter Park, FL 32789
On Market For 12 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1804

  • Year Built

    1951

  • $/SqFt

    $304

No limit for your imagination on this property. INTERNATIONAL FLORIDA PROPERTIES INC.

Pended $3,850,000

Elegant two-story home with a tile roof, arched entryway, balcony, lush landscaping, and a circular driveway at 861 Bonita Dr, Winter Park, FL 32789
Gorgeous two-story house showcasing manicured landscaping, a tile roof, arched entryway, and a brick-paved driveway at 861 Bonita Dr, Winter Park, FL 32789
Aerial view of a magnificent home surrounded by trees, showcasing the tile roof and circular driveway at 861 Bonita Dr, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 11 Days
  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    6939

  • Year Built

    1999

  • $/SqFt

    $555

Comstock Park - Situated in the heart of Winter Park, this exquisite property offers the perfect blend of sophistication, comfort, privacy, and location. PREMIER SOTHEBY'S INTL. REALTY.

Pended $3,995,000

Beautiful home exterior with mature palms, stone accents, lush landscaping, and a spacious paver driveway at 2020 Venetian Way, Winter Park, FL 32789
Idyllic waterfront backyard with a private dock, lush landscaping, and serene lake views at 2020 Venetian Way, Winter Park, FL 32789
Picturesque backyard with a private dock, beautiful sunset views over the water, and mature trees at 2020 Venetian Way, Winter Park, FL 32789
On Market For 17 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4188

  • Year Built

    1979

  • $/SqFt

    $954

Many amenities are minutes away and include a short distance to Winter Park Racquet Club, close to Park Avenue, major roadways and fantastic schools Dommerich Elementary, Maitland Middle and Winter Park High. PREMIER SOTHEBY'S INTL. REALTY.

Pended $1,885,000

Beautiful white modern home with a manicured lawn and a black two-car garage at 2144 Sycamore Dr, Winter Park, FL 32789
Modern kitchen with an island, white cabinetry, stainless steel appliances, and a wine cooler at 2144 Sycamore Dr, Winter Park, FL 32789
Open living and dining area with hardwood floors, a fireplace, and plenty of natural light at 2144 Sycamore Dr, Winter Park, FL 32789
On Market For 17 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3499

  • Year Built

    2024

  • $/SqFt

    $539

Northwood Terrace - Stunning new Winter Park residence. COMPASS FLORIDA LLC.

Home For Sale $1,650,000

Beautiful home showcasing modern design with grey brick, a driveway, and a well-kept lawn at 2408 Lafayette Ave, Winter Park, FL 32789
Open-concept living and dining area featuring hardwood floors, modern decor, and ample natural light at 2408 Lafayette Ave, Winter Park, FL 32789
Cozy sitting room with modern chairs, stylish decor, and a large window with natural light at 2408 Lafayette Ave, Winter Park, FL 32789
On Market For 18 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2838

  • Year Built

    2024

  • $/SqFt

    $581

Winter Park Village - This home is a true gem that combines thoughtful details with sophisticated style. CORCORAN PREMIER REALTY.

Pended $1,495,000

Inviting home exterior with lush greenery, trimmed hedges, and a cozy seating area on the porch at 1601 Chestnut Ave, Winter Park, FL 32789
Welcoming front porch with chairs, lush greenery and a decorative door at 1601 Chestnut Ave, Winter Park, FL 32789
Bright foyer featuring wood floors, decorative table with mirror, and a glass panel door at 1601 Chestnut Ave, Winter Park, FL 32789
On Market For 17 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2795

  • Year Built

    2017

  • $/SqFt

    $535

Lake Knowles Terrace - A location like no other, call today to schedule your private tour. KELLER WILLIAMS ELITE PARTNERS III REALTY.

Pended $799,990

An elevated view showcasing a well-maintained home with manicured landscaping and a beautiful roof at 440 Shoreview Ave, Winter Park, FL 32789
A stunning aerial view of a home near a picturesque lake and lush greenery, highlighting serene surroundings at 440 Shoreview Ave, Winter Park, FL 32789
Inviting entryway featuring dark hardwood floors, a striking front door, and elegant decor at 440 Shoreview Ave, Winter Park, FL 32789
On Market For 16 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2205

  • Year Built

    2014

  • $/SqFt

    $363

Killarney Estates - Call/Text for a private showing today. COMPASS FLORIDA LLC.

Home For Sale $2,150,000

Inviting home with a metal roof, manicured landscaping, and front porch at 1560 Woodland Ave, Winter Park, FL 32789
Charming home featuring a circular driveway, mature trees, and a well-manicured lawn at 1560 Woodland Ave, Winter Park, FL 32789
Beautifully landscaped home with a circular driveway, stone accents, and a welcoming front porch at 1560 Woodland Ave, Winter Park, FL 32789
On Market For 18 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3851

  • Year Built

    1990

  • $/SqFt

    $558

Comstock Park - A must see for those seeking the tranquil and exquisite Winter Park standard of living. LOKATION.

Home For Sale $1,050,000

The bright, sunny home has a two-car garage and a brick-paved driveway, and is surrounded by manicured landscaping at 2680 Oglesby Ave, Winter Park, FL 32789
The front entrance features a modern blue door with glass panes, complemented by well-maintained landscaping at 2680 Oglesby Ave, Winter Park, FL 32789
Bright, open foyer with hardwood floors leads to the living area, showcasing the home's modern design at 2680 Oglesby Ave, Winter Park, FL 32789
On Market For 19 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2546

  • Year Built

    2019

  • $/SqFt

    $412

Dubsdread Heights - There is no HOA in this community. This home is available immediately. COMPASS FLORIDA LLC.

Pended $2,395,000

A luxurious backyard with a pool, spa, outdoor kitchen, fireplace, and covered patio at 2814 Parkland Dr, Winter Park, FL 32789
Gorgeous exterior showing a two-car garage, stone details, a lush lawn, and dark facade at 2814 Parkland Dr, Winter Park, FL 32789
A well-lit backyard featuring a pool, spa, outdoor patio, fireplace, and exterior kitchen at 2814 Parkland Dr, Winter Park, FL 32789
On Market For 20 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3089

  • Year Built

    2025

  • $/SqFt

    $775

Lake Forest Park - You will not find a better opportunity to secure a recently completed, highly detailed, unique luxury home in the WP area that offers the feel, presentation, and function of 2814 Parkland Drive. KELLER WILLIAMS REALTY AT THE PARKS.

Pended $325,000

Landscaped front yard and charming single-story home with a red brick chimney and ample sunlight at 712 Baffie Ave, Winter Park, FL 32789
Well-kept home with mature trees, a manicured lawn, and great curb appeal at 712 Baffie Ave, Winter Park, FL 32789
Inviting sunroom with tile floors, wood ceiling, and bright lighting, perfect for relaxing at 712 Baffie Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 18 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1304

  • Year Built

    1925

  • $/SqFt

    $249

Dubsdread Heights - A great opportunity for first-time buyers, builders, or investors looking to buy smart and improve the asset. BALDWIN PARK REALTY LLC.

Pended $2,400,000

Charming single-story home featuring a well-manicured lawn, mature landscaping and a covered front porch at 673 Balmoral Rd, Winter Park, FL 32789
Charming single-story home featuring a well-manicured lawn, mature landscaping and a covered front porch at 673 Balmoral Rd, Winter Park, FL 32789
Charming single-story home featuring a well-manicured lawn, mature landscaping and a covered front porch at 673 Balmoral Rd, Winter Park, FL 32789
On Market For 18 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2663

  • Year Built

    1964

  • $/SqFt

    $901

Kenilworth Shores - Don’t miss the opportunity to tour this home – schedule your showing today. KELLY PRICE & COMPANY LLC.

Home For Sale $499,000

Reduced By $16,000

Inviting one-story home boasts lush landscaping and an attached garage at 1564 Cavendish Rd, Winter Park, FL 32789
A charming one-story home features a lush lawn and an attached garage at 1564 Cavendish Rd, Winter Park, FL 32789
Cozy front porch with white columns and a seating area at 1564 Cavendish Rd, Winter Park, FL 32789
On Market For 22 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1140

  • Year Built

    1953

  • $/SqFt

    $438

This community is in the heart of Winter Park, close to Park Ave, museums, restaurants and shoppes. CHARLES RUTENBERG REALTY ORLANDO.

Pended $1,875,000

Contemporary home with a manicured lawn, trimmed hedges, and tall palm trees enhancing curb appeal at 1970 Laurel Rd, Winter Park, FL 32789
Sophisticated modern architecture featuring a well-kept lawn, manicured greenery, and stately palm trees at 1970 Laurel Rd, Winter Park, FL 32789
Close-up of the home's entrance, showcasing the walkway and professionally maintained landscaping at 1970 Laurel Rd, Winter Park, FL 32789
On Market For 17 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3440

  • Year Built

    2015

  • $/SqFt

    $545

Charmont - Don’t miss this opportunity and schedule your private showing today! PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $3,950,000

Expansive aerial view of the house surrounded by lush greenery, mature trees, and featuring a pool and brick driveway at 851 Georgia Ave, Winter Park, FL 32789
Inviting entryway features a detailed wooden door, brick pathway, and decorative plants, creating a warm welcome at 851 Georgia Ave, Winter Park, FL 32789
Elegant foyer showcasing wood floors, arched doorways, a staircase, and a stylish console table with vibrant artwork at 851 Georgia Ave, Winter Park, FL 32789
On Market For 26 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4314

  • Year Built

    1935

  • $/SqFt

    $916

This home offers the best of both worlds: a rare opportunity to own a piece of Winter Park history, yet lovingly maintained with modern updates and conveniences throughout. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $565,000

Bright living room featuring hardwood floors, cozy furniture, and ample natural light at 2381 Roxbury Rd, Winter Park, FL 32789
Inviting living area with fireplace, hardwood floors, and a ceiling fan at 2381 Roxbury Rd, Winter Park, FL 32789
Spacious open-concept living area featuring a fireplace, hardwood floors, and lots of windows at 2381 Roxbury Rd, Winter Park, FL 32789
On Market For 20 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1645

  • Year Built

    1949

  • $/SqFt

    $343

Glencoe - Highly Sought after- Move in Ready ! HURRY! Won't Last! ! KELLER WILLIAMS HERITAGE REALTY.

Pended $415,000

Aerial view showcases this home's proximity to a golf course, pond, and city skyline at 2259 Minnesota Ave, Winter Park, FL 32789
Charming blue home with well-maintained lawn, fenced backyard and access to paved street at 2259 Minnesota Ave, Winter Park, FL 32789
Inviting home showcasing lush front lawn, mature trees, and paved street access at 2259 Minnesota Ave, Winter Park, FL 32789
On Market For 25 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1015

  • Year Built

    1948

  • $/SqFt

    $409

20k impact fee credit/verify exact when pulling new permit LPT REALTY, LLC.

Pended $2,695,000

An elevated aerial view of the luxury home featuring a beautifully landscaped yard, mature trees, and a brick driveway at 254 Sylvan Blvd, Winter Park, FL 32789
Panoramic aerial view of the property showcasing its expansive layout, lush landscaping, and proximity to a lake at 254 Sylvan Blvd, Winter Park, FL 32789
Beautiful facade with palm trees, well-manicured landscaping, and paver driveway leading to the garage and front entrance at 254 Sylvan Blvd, Winter Park, FL 32789
On Market For 27 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3653

  • Year Built

    2000

  • $/SqFt

    $738

Sylvan Lake Shores - Don’t miss the opportunity to make this lake front home yours. Schedule your private showing today! KELLER WILLIAMS WINTER PARK.

Home For Sale $1,650,000

A picturesque home with lush landscaping and mature trees adding natural beauty at 1701 Palmer Ave, Winter Park, FL 32789
Private courtyard area featuring tiled flooring and a charming decorative water feature at 1701 Palmer Ave, Winter Park, FL 32789
Outdoor kitchen area boasting a stainless steel grill and counter space at 1701 Palmer Ave, Winter Park, FL 32789
On Market For 26 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2841

  • Year Built

    1953

  • $/SqFt

    $581

Jenkins - Whether you're looking to move in and make it your own or renovate to create your dream home, this is a chance you don’t want to miss! Schedule your showing today! TRUST EQUITY GROUP LLC.

Pended $3,400,000

Spacious backyard features a brick patio, manicured hedges, and a cozy fire pit area at 1911 Stonehurst Rd, Winter Park, FL 32789
Aerial view of a luxury home showcasing its manicured backyard and sparkling swimming pool at 1911 Stonehurst Rd, Winter Park, FL 32789
Inviting front porch with rocking chairs, a decorative rug, and classic brick facade at 1911 Stonehurst Rd, Winter Park, FL 32789
On Market For 29 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    5097

  • Year Built

    2001

  • $/SqFt

    $667

Stonehurst Estates - *Ask for a list of improvements, the floorplan and click on the virtual tour! FANNIE HILLMAN & ASSOCIATES.

Pended $875,000

Charming single-story home at dusk, featuring a well-manicured lawn and inviting curb appeal at 1832 Magnolia Ave, Winter Park, FL 32789
Inviting entryway showcasing wood floors, a decorative front door, and neutral wall paint at 1832 Magnolia Ave, Winter Park, FL 32789
Bright living room with stylish decor, wood flooring, modern lighting, and a comfortable sectional sofa at 1832 Magnolia Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 26 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2910

  • Year Built

    1954

  • $/SqFt

    $301

Temple Terrace - Don't miss the opportunity to make this unique Winter Park home yours! COMPASS FLORIDA LLC.

Home For Sale $2,895,000

Elegant stucco home with a red tile roof, framed by palm trees and a circular driveway offering ample parking space at 1630 Lasbury Ave, Winter Park, FL 32789
Long brick paver driveway and lush landscaping leading to beautiful homes; palm tree shadows dappling the walkway at 1630 Lasbury Ave, Winter Park, FL 32789
Bright living room with hardwood floors, a piano, French doors to a pool, and neutral-toned furniture at 1630 Lasbury Ave, Winter Park, FL 32789
On Market For 33 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    4912

  • Year Built

    2003

  • $/SqFt

    $589

Comstock Park - It’s a rare find in one of Winter Park’s most desirable neighborhoods. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,070,000

Aerial view of a home with a private pool, lush greenery, and neatly fenced yard providing a serene retreat at 250 Cortland Ave, Winter Park, FL 32789
Bright living room features vaulted ceiling, hardwood floors, sliding glass doors to a pool, and neutral decor at 250 Cortland Ave, Winter Park, FL 32789
Spacious game room with a pool table, drum set, hardwood floors, and skylights, perfect for entertaining and leisure at 250 Cortland Ave, Winter Park, FL 32789
On Market For 32 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2114

  • Year Built

    1981

  • $/SqFt

    $506

Cortland Park - Don't miss the opportunity to own this true neighborhood gem in Winter Park, where luxury living and convenience meet. EXP REALTY LLC.

Home For Sale $849,000

Inviting front entrance showcasing a dark-colored front door, brick paver walkway, and attached garage at 705 Baffie Ave, Winter Park, FL 32789
Bright kitchen features a large center island, stainless steel appliances, and modern pendant lighting at 705 Baffie Ave, Winter Park, FL 32789
Spacious kitchen with a long island featuring stainless steel appliances, hardwood floors, and pendant lighting at 705 Baffie Ave, Winter Park, FL 32789
On Market For 16 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2563

  • Year Built

    2020

  • $/SqFt

    $331

Dubsdread Heights - Don’t miss your chance to make it yours, schedule your showing today. PREMIER SOTHEBY'S INTL. REALTY.

Pended $3,250,000

Beautiful two-story home showcasing modern architecture, a well-maintained lawn, and a spacious driveway at 1833 Loch Berry Rd, Winter Park, FL 32789
Elegant home entrance featuring a striking arched doorway, meticulous landscaping, and stone walkway at 1833 Loch Berry Rd, Winter Park, FL 32789
Bright foyer with herringbone wood floors, designer lighting, and an arched entryway, offering a grand welcome at 1833 Loch Berry Rd, Winter Park, FL 32789
On Market For 27 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4770

  • Year Built

    2025

  • $/SqFt

    $681

Kenilworth Shores - Don’t miss your opportunity to own this stunning Winter Park home crafted by renowned builder Vimaro Homes. COMPASS FLORIDA LLC.

Home For Sale $1,475,000

Charming brick home with manicured lawn, brick pathway, and lush landscaping, creating inviting curb appeal at 1600 Barcelona Way, Winter Park, FL 32789
Charming brick home with manicured lawn, brick pathway, and lush landscaping, creating inviting curb appeal at 1600 Barcelona Way, Winter Park, FL 32789
Charming brick home with manicured lawn, brick pathway, and lush landscaping, creating inviting curb appeal at 1600 Barcelona Way, Winter Park, FL 32789
On Market For 33 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3014

  • Year Built

    1972

  • $/SqFt

    $489

Don't miss your chance to own a piece of Winter Park's rich heritage! LPT REALTY, LLC.

Pended $589,000

Charming single story home featuring a gravel driveway, covered entryway, and well maintained lawn at 3006 Northwood Blvd, Winter Park, FL 32789
A close up of the front door, shows the house number, covered parking, and clean well kept yard at 3006 Northwood Blvd, Winter Park, FL 32789
Well manicured yard with healthy plants and flowers, featuring a short retaining wall around the landscaped area at 3006 Northwood Blvd, Winter Park, FL 32789
On Market For 33 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1710

  • Year Built

    1953

  • $/SqFt

    $344

Northwood Terrace - Don't miss out and schedule your private tour today! CREEGAN GROUP.

Home For Sale $4,395,000

Stunning two-story home with manicured lawn, covered front porch, balcony, and elegant design at 1840 W Fawsett Rd, Winter Park, FL 32789
Inviting covered porch featuring comfortable seating, ceiling fans, and beautiful lake views at 1840 W Fawsett Rd, Winter Park, FL 32789
Cozy living room with a fireplace, high ceilings, large windows, and stylish furnishings at 1840 W Fawsett Rd, Winter Park, FL 32789
On Market For 34 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4129

  • Year Built

    1998

  • $/SqFt

    $1,064

Showings are by appointment only – schedule yours today. KELLY PRICE & COMPANY LLC.

Pended $1,500,000

Inviting covered porch with stone accents, decorative columns, and cozy seating area with a blue front door at 1741 Pine Ave, Winter Park, FL 32789
Bright foyer featuring hardwood floors, an elegant chandelier, and a glimpse into the open-concept living space at 1741 Pine Ave, Winter Park, FL 32789
Elegant dining room with hardwood floors and decoratively appointed furniture adjacent to the living area at 1741 Pine Ave, Winter Park, FL 32789
On Market For 36 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3297

  • Year Built

    2002

  • $/SqFt

    $455

Conwill Estates - Plus, with top-rated Winter Park Schools, this home offers everything you need! FANNIE HILLMAN & ASSOCIATES.

Pended $1,800,000

Bright, spacious kitchen with a large island, pendant lighting, modern appliances, and an adjacent dining area at 1682 Arbor Park Dr, Winter Park, FL 32789
Elegant living room with a modern fireplace, hardwood floors, ample seating, and natural light from the large sliding glass doors at 1682 Arbor Park Dr, Winter Park, FL 32789
Serene main bedroom with large windows, modern lighting, and a comfortable seating area, perfect for relaxation at 1682 Arbor Park Dr, Winter Park, FL 32789
On Market For 37 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2950

  • Year Built

    2025

  • $/SqFt

    $610

Conwill Estates - Final construction details, finishes, and features may vary. COMPASS FLORIDA LLC.

Home For Sale $1,775,000

Modern kitchen features a marble island with bar seating, pendant lighting, and stainless steel appliances at 1702 Arbor Park Dr, Winter Park, FL 32789
Bright living room boasts a modern fireplace and light hardwood floors with sliding doors to the pool at 1702 Arbor Park Dr, Winter Park, FL 32789
Stylish primary bedroom features a king bed, hardwood floors, modern lighting, and windows at 1702 Arbor Park Dr, Winter Park, FL 32789
On Market For 37 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2950

  • Year Built

    2025

  • $/SqFt

    $602

Conwill Estates - Final construction details, finishes, and features may vary. COMPASS FLORIDA LLC.

Home For Sale $1,299,000

Reduced By $76,000

An eye-level shot of the home's front exterior with the garage on the left at 1213 Richmond Rd, Winter Park, FL 32789
Welcoming foyer featuring hardwood floors, decorative sconces, and beautiful wrought iron railing at 1213 Richmond Rd, Winter Park, FL 32789
Kitchen with stainless appliances, modern cabinetry, and granite countertops at 1213 Richmond Rd, Winter Park, FL 32789
On Market For 40 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3204

  • Year Built

    1925

  • $/SqFt

    $405

This is the rare chance to live in an exceptional location that blends luxury, convenience, and tranquility. KELLY PRICE & COMPANY LLC.

Pended $4,799,900

Beautiful modern two-story home with a manicured lawn, stone accents, and a spacious three-car garage at 1691 Chestnut Ave, Winter Park, FL 32789
Beautiful modern two-story home with manicured landscaping and an inviting, paved driveway and walkway at 1691 Chestnut Ave, Winter Park, FL 32789
Modern two-story home featuring manicured landscaping and an inviting paved driveway and walkway, lit for evening at 1691 Chestnut Ave, Winter Park, FL 32789
On Market For 42 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4582

  • Year Built

    2024

  • $/SqFt

    $1,048

Lake Knowles Terrace - This elegant home will not last! COMPASS FLORIDA LLC.

Home For Sale $4,395,000

Reduced By $480,000

Modern two-story home with manicured lawn and beautiful landscaping at twilight at 229 Alexander Pl, Winter Park, FL 32789
Detailed view of the entryway, highlighting the modern door, stone facade, and the sleek, minimalist design at 229 Alexander Pl, Winter Park, FL 32789
Open-concept living room with access to an outdoor lounge and a view of the pool area and modern tile flooring at 229 Alexander Pl, Winter Park, FL 32789
On Market For 42 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4431

  • Year Built

    2012

  • $/SqFt

    $992

Experience luxury, innovation and convenience in one of Winter Park’s sought-after locations, moments from dining, shopping and cultural experiences. PREMIER SOTHEBY'S INTL. REALTY.

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 386-801-4854 and speak with one of our real estate consultants.

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