150 Results

32789 Homes For Sale & 32789 FL Real Estate

Home For Sale $2,575,000

Beautiful front entrance with a stone walkway, manicured landscaping, and a stylish modern door at 1795 Greenwich Ave, Winter Park, FL 32789
Bright and airy living room with a comfortable gray sectional, wood floors, and access to the outdoors at 1795 Greenwich Ave, Winter Park, FL 32789
Stylish living room showcasing a modern fireplace, comfortable seating, and large windows at 1795 Greenwich Ave, Winter Park, FL 32789
On Market Today
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3852

  • Year Built

    2019

  • $/SqFt

    $668

Zoned for top-rated Winter Park schools (Brookshire, Glenridge, Winter Park High) and near private schools- Lake Highland Prep, Park Maitland, Geneva School and more KELLY PRICE & COMPANY LLC.

Home For Sale $1,299,000

Beautiful home featuring a brick driveway, lush lawn, and meticulous landscaping at 1341 Lyndale Blvd, Winter Park, FL 32789
Inviting front entryway with a stylish light fixture and elegant glass-paneled door at 1341 Lyndale Blvd, Winter Park, FL 32789
Elegant hallway features hardwood floors, archways, and modern chandelier at 1341 Lyndale Blvd, Winter Park, FL 32789
On Market For 2 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2388

  • Year Built

    2007

  • $/SqFt

    $544

Dixie Terrace - Located in a top-rated school district and are the corner from shops, restaurants, parks, and more, this home offers a lifestyle of comfort, charm, and convenience in one of Winter Park’s most sought-after neighborhoods. COMPASS FLORIDA LLC.

Home For Sale $2,295,000

An inviting backyard with a sparkling pool, jacuzzi, outdoor fireplace, and ample lounging space at 2614 Parkland Dr, Winter Park, FL 32789
A captivating aerial view showcasing the home's backyard pool, patio, and impeccable landscaping at 2614 Parkland Dr, Winter Park, FL 32789
An aerial view displays the home's beautiful landscaping, unique driveway, and a tranquil setting at 2614 Parkland Dr, Winter Park, FL 32789
On Market For 3 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3307

  • Year Built

    2007

  • $/SqFt

    $694

Parklando - With a brand-new tile roof, all-natural gas appliances, and an unbeatable location, this home is the definition of elevated Winter Park living. JW GASTON LLC.

Home For Sale $3,850,000

Charming two-story home with manicured lawn, gray metal roof and blue shutters at 2171 Forrest Rd, Winter Park, FL 32789
Elegant foyer with hardwood floors, a chandelier, and a wood-framed glass door at 2171 Forrest Rd, Winter Park, FL 32789
Inviting sitting room with built-in bookshelves and comfortable seating at 2171 Forrest Rd, Winter Park, FL 32789
On Market For 5 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4565

  • Year Built

    2016

  • $/SqFt

    $843

This remarkable property offers the ultimate in refined living, combining luxury, comfort and convenience in one of Central Florida’s sought-after communities. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $3,195,000

Charming home entrance featuring a pergola with covered walkway, leading to the custom doors and lush landscaping at 1020 Mayfield Ave, Winter Park, FL 32789
Beautiful custom entryway with modern pergola and custom door design framed by manicured greenery at 1020 Mayfield Ave, Winter Park, FL 32789
Elegant front entrance with custom wood door framed by symmetrical landscaping and a neutral color palette at 1020 Mayfield Ave, Winter Park, FL 32789
On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2663

  • Year Built

    1989

  • $/SqFt

    $1,200

Kronenberger - Located just a short drive, walk, or bike ride from Park Avenue, this impeccable home it close to both Interlachen Golf and Country Club, the Winter Park Raquet Club, nearby shops and dining, Advent Health, and is zoned for the A-rated Lakemont/Maitland/WPHS school district. KELLY PRICE & COMPANY LLC.

Home For Sale $2,650,000

Beautifully landscaped modern home featuring a clean white facade, balcony, and stylish driveway at 1700 Palm Ave, Winter Park, FL 32789
Aerial view of backyard featuring a modern pool, patio furniture, and well-manicured lawn at 1700 Palm Ave, Winter Park, FL 32789
Outdoor kitchen featuring stainless steel appliances, marble counters, a wood ceiling, and a view of the pool at 1700 Palm Ave, Winter Park, FL 32789
On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3770

  • Year Built

    2016

  • $/SqFt

    $703

Winter Park Heights - Ideally located just blocks from Winter Park’s renowned shops, dining, YMCA, and AdventHealth Hospital—and zoned for top-rated schools—this home delivers elevated living in one of Central Florida’s most coveted neighborhoods. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,550,000

Inviting entrance with double wooden doors, white Adirondack chairs, and a circular brick walkway at 1661 Woodland Ave, Winter Park, FL 32789
Elegant foyer with marble floors, staircase with white railings, and a view of the living and dining areas at 1661 Woodland Ave, Winter Park, FL 32789
Spacious living area with hardwood floors, arched windows, a chaise lounge, and a dining table at 1661 Woodland Ave, Winter Park, FL 32789
On Market For 6 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3215

  • Year Built

    1948

  • $/SqFt

    $482

Comstock Park - This home blends elegance, comfort, and functionality—an entertainer’s dream with a fantastic flow for everyday living! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,795,000

Landscaped front yard featuring a modern two-story home with a two-car garage and beautiful curb appeal at 2813 Northwood Blvd, Winter Park, FL 32789
Bright foyer featuring a glass-paneled front door, hardwood floors, and modern decor at 2813 Northwood Blvd, Winter Park, FL 32789
Modern staircase with a unique hanging light fixture and natural light from a nearby window at 2813 Northwood Blvd, Winter Park, FL 32789
On Market For 7 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3444

  • Year Built

    2021

  • $/SqFt

    $521

Northwood Terrace - Experience the elegance and lifestyle this home offers and reach out today to arrange your private showing. PREMIER SOTHEBY'S INTL. REALTY.

Pended $414,900

Cozy home with a covered carport and attractive landscaping, situated on a well-kept lot at 2743 Sanbina St, Winter Park, FL 32789
Bright living room with a neutral color palette, Terrazzo floors and stylish decor, creating a modern space at 2743 Sanbina St, Winter Park, FL 32789
Inviting living space with Terrazzo floors, featuring large windows and elegant furnishings for comfortable living at 2743 Sanbina St, Winter Park, FL 32789
On Market For 4 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1226

  • Year Built

    1960

  • $/SqFt

    $338

Howell Heights - Don’t miss your chance to call it yours! KELLER WILLIAMS WINTER PARK.

Home For Sale $525,000

A single-story home with a screened-in porch and a concrete driveway surrounded by mature trees at 2507 Lafayette Ave, Winter Park, FL 32789
The side of the house with an exterior door, small window and trash bins along a stone path at 2507 Lafayette Ave, Winter Park, FL 32789
The home's backyard with lush green ground cover, trees, a grill, and a ladder at 2507 Lafayette Ave, Winter Park, FL 32789
On Market For 8 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    943

  • Year Built

    1956

  • $/SqFt

    $557

Winter Park Village - Your future of luxury living in Winter Park awaits on Lafayette Avenue. -- RE/MAX ASSURED.

Pended $8,995,000

Beautiful two-story home featuring a brick driveway, manicured landscaping, and a classic architectural style at 2001 Bett Mar Ln, Winter Park, FL 32789
Charming home with lush green landscaping, an inviting entrance, and a brick driveway leading up to the property at 2001 Bett Mar Ln, Winter Park, FL 32789
Elegant estate featuring a brick driveway, wrought iron gate, and mature trees surrounding the property at 2001 Bett Mar Ln, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 2 Days
  • Bedrooms

    8

  • Full Bath(s)

    8

  • Sq. Ft.

    8583

  • Year Built

    1995

  • $/SqFt

    $1,048

Green Oaks - Don’t miss this rare opportunity to claim this stunning residence as your own—schedule a private showing today to experience the unparalleled elegance and uniqueness of this extraordinary estate! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $3,490,000

Modern kitchen with marble island, sleek gray cabinetry, pendant lighting, and stainless steel appliances at 1910 Glencoe Rd, Winter Park, FL 32789
Bright living room with fireplace, custom built-ins, hardwood floors, and large windows at 1910 Glencoe Rd, Winter Park, FL 32789
Serene bedroom with a canopy bed, neutral decor, and a sliding glass door to the outdoors at 1910 Glencoe Rd, Winter Park, FL 32789
On Market For 9 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4205

  • Year Built

    2025

  • $/SqFt

    $830

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

Home For Sale $3,295,000

Close up view of the front entrance with modern design, black door and side lights at 532 Worthington Dr, Winter Park, FL 32789
Close up view of the front entrance with modern design, black door and side lights at 532 Worthington Dr, Winter Park, FL 32789
Open concept Living Room includes hardwood floors, large dining table, and direct access to the patio at 532 Worthington Dr, Winter Park, FL 32789
On Market For 9 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3974

  • Year Built

    2023

  • $/SqFt

    $829

Kenilworth Shores - You can make this home your new reality! FLORIDA ONE REAL ESTATE LLC.

Pended $649,000

On Market For 9 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1812

  • Year Built

    1953

  • $/SqFt

    $358

Lake Knowles Terrace - Value is in the land. RE/MAX 200 REALTY.

Home For Sale $349,990

Charming single-story home featuring manicured shrubs and a concrete walkway at 320 Granada Dr, Winter Park, FL 32789
Spacious living room with hardwood floors and a cozy fireplace at 320 Granada Dr, Winter Park, FL 32789
Bright living room featuring hardwood floors and several windows for natural light at 320 Granada Dr, Winter Park, FL 32789
On Market For 9 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1401

  • Year Built

    1946

  • $/SqFt

    $250

Don’t miss the opportunity to own a piece of Winter Park charm! KELLER WILLIAMS WINTER PARK.

Home For Sale $595,000

Landscaped front yard with mature tree, a driveway leading to a garage, and a well-maintained lawn at 1821 Goodrich Ave, Winter Park, FL 32789
Well-maintained front yard with a mature tree, a long driveway, and partial view of the cozy home at 1821 Goodrich Ave, Winter Park, FL 32789
Functional kitchen featuring bright yellow cabinetry, white appliances, and stylish tiled backsplash at 1821 Goodrich Ave, Winter Park, FL 32789
On Market For 10 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1000

  • Year Built

    1955

  • $/SqFt

    $595

Sylvan Heights - Note: no house showings prior to entering into an acceptable contract and having access during the inspection period, as value is in the land. PREMIER SOTHEBY'S INTL. REALTY.

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 14 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 13 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 $2,249,000

Reduced By $241,000

Charming two-story home with mature landscaping and a manicured lawn at 1299 Harding Street, Winter Park, FL 32789
Inviting home entrance featuring a brick path and lush, colorful landscaping at 1299 Harding Street, Winter Park, FL 32789
Backyard brick patio with dining and lounge seating surrounded by lush landscaping at 1299 Harding Street, Winter Park, FL 32789
On Market For 14 Days
  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    3784

  • Year Built

    1951

  • $/SqFt

    $594

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 14 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1662

  • Year Built

    1953

  • $/SqFt

    $406

Northwood Terrace - 3/1.5 Bath with large Florida Room. 2 Car Carport. SAND DOLLAR REALTY GROUP INC.

Pended $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 13 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.

Pended $495,000

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 4 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    960

  • Year Built

    1950

  • $/SqFt

    $516

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 15 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 15 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 16 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.

Pended $799,999

On Market For 12 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 $359,000

Reduced By $16,000

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
*POTENTIAL GREAT VALUE
On Market For 19 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1456

  • Year Built

    1995

  • $/SqFt

    $247

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 20 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 20 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 20 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 21 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 20 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 21 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.

Home For Sale $1,400,000

Close up of the home's beautiful arched doorway, trimmed with columns, and surrounding well maintained landscaping at 1370 Alberta Dr, Winter Park, FL 32789
Bright living room showcasing hardwood floors and an open doorway to the adjacent room at 1370 Alberta Dr, Winter Park, FL 32789
Cozy living room featuring hardwood floors, a fireplace, and ample natural light at 1370 Alberta Dr, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 15 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3483

  • Year Built

    1957

  • $/SqFt

    $402

Located in Winter Park's prestigious school district, this home represents the perfect combination of luxury, convenience, and long-term value. FANNIE HILLMAN & ASSOCIATES.

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 26 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.

Home For Sale $1,550,000

Reduced By $100,000

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 27 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2838

  • Year Built

    2024

  • $/SqFt

    $546

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 26 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 25 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 28 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 28 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 29 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 15 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 27 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 31 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 26 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.

Pended $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 34 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 29 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 17 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 36 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 35 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.

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 954 439 6446 and speak with one of our real estate consultants.

EasyStreet

Call to Schedule a Showing

(954) 439-6446

(954) 439-6446