136 Results

32789 Homes For Sale & 32789 FL Real Estate

Pended $1,395,000

On Market For 1 Day
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2516

  • Year Built

    1957

  • $/SqFt

    $554

Located in a sought-after school district, this neighborhood offers an exceptional educational environment. FANNIE HILLMAN & ASSOCIATES.

Pended $1,265,000

Attractive single-story home with brick exterior, well-kept lawn, and inviting curb appeal at 420 Sylvan Dr, Winter Park, FL 32789
Brick home with a driveway and well maintained front yard and appealing landscaping at 420 Sylvan Dr, Winter Park, FL 32789
Bright living space with a fireplace, neutral furniture, and an open layout to the dining area at 420 Sylvan Dr, Winter Park, FL 32789
On Market For 0 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2676

  • Year Built

    1950

  • $/SqFt

    $473

Sylvan Park - Data entry only. CORCORAN PREMIER REALTY.

Home For Sale $649,000

Beautiful home showcasing well-maintained landscaping, a quaint walkway, and a bright, welcoming facade at 721 Glenridge Way, Winter Park, FL 32789
Inviting outdoor patio with a turquoise table set and lush artificial turf, perfect for relaxing or entertaining at 721 Glenridge Way, Winter Park, FL 32789
Welcoming front entrance with a dark wood door, tiled flooring, and decorative plants for added curb appeal at 721 Glenridge Way, Winter Park, FL 32789
On Market For 2 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1545

  • Year Built

    1981

  • $/SqFt

    $420

Lake Virginia - Call today to schedule your private showing! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $4,500,000

Charming white home showcasing a whimsical blue sky door and manicured front yard at 1336 College Pt, Winter Park, FL 32789
Beautiful backyard features an in-ground pool, lounge chairs, and guest house surrounded by green lawns at 1336 College Pt, Winter Park, FL 32789
Waterfront view of home with boat dock, lush lawns and tall trees at 1336 College Pt, Winter Park, FL 32789
On Market For 4 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3181

  • Year Built

    1926

  • $/SqFt

    $1,415

Virginia Heights - This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $2,990,000

Beautiful two-story home featuring a manicured lawn, classic black shutters, and elegant architectural details at 1860 Via Contessa, Winter Park, FL 32789
Inviting living room with neutral sofas, stylish wood accent wall, and bright natural light at 1860 Via Contessa, Winter Park, FL 32789
Elegant dining room featuring a modern light fixture, wood accent wall, and seating for six at 1860 Via Contessa, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 7 Days
  • Bedrooms

    8

  • Full Bath(s)

    6

  • Sq. Ft.

    7000

  • Year Built

    2003

  • $/SqFt

    $427

Lugano Terrace - One or more photo(s) has been virtually staged. SIERRA REALTY GROUP LLC.

Home For Sale $975,000

On Market For 8 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1045

  • Year Built

    1925

  • $/SqFt

    $933

This home has been remodeled and is a show place. A must see!! ! KELLER WILLIAMS WINTER PARK.

Home For Sale $2,500,000

Stunning two-story home with a grand entrance, featuring a beautifully landscaped front yard and second story balcony at 450 Lakewood Dr, Winter Park, FL 32789
Enjoy outdoor living on this covered patio, with views of the pool and lush landscaping at 450 Lakewood Dr, Winter Park, FL 32789
Backyard pool with fountain and spa, complemented by the home's architecture at 450 Lakewood Dr, Winter Park, FL 32789
On Market For 8 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4676

  • Year Built

    2000

  • $/SqFt

    $535

Osceola Shores - Home has natural gas for the tankless water heater, pool heater, cooktop and the outdoor firepit. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $749,000

Modern kitchen featuring white cabinets, granite countertops, stainless steel appliances, and stylish lighting at 2812 Mulford Ave, Winter Park, FL 32789
Contemporary kitchen with black appliances, granite countertops, white cabinets, and sleek modern lighting at 2812 Mulford Ave, Winter Park, FL 32789
Well-lit kitchen featuring stainless steel appliances, white cabinetry, granite counters and a dining area at 2812 Mulford Ave, Winter Park, FL 32789
On Market For 8 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1527

  • Year Built

    1953

  • $/SqFt

    $491

Northwood Terrace - The living room also connects via french doors to a great flex space that could morph into a homework station, home office, or new laundry room. Welcome Home! SYNCHRONICITY REAL ESTATE SOLUTIONS.

Home For Sale $5,700,000

Beautiful two-story home with a landscaped front yard, manicured hedges and a paver driveway at 1660 Palmer Ave, Winter Park, FL 32789
An elegant two-story home is beautifully landscaped and includes planters and manicured gardens at 1660 Palmer Ave, Winter Park, FL 32789
A charming front entry boasts a covered porch with black lanterns and beautiful double doors at 1660 Palmer Ave, Winter Park, FL 32789
On Market For 9 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6406

  • Year Built

    2024

  • $/SqFt

    $890

Comstock Park - The furnishings package can be purchased separately. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $2,499,900

Lakeside home with a private boat dock, jet ski, and manicured lawn at 301 Rippling Ln, Winter Park, FL 32789
Beautiful backyard with a sparkling pool, outdoor seating, and lush green lawn at 301 Rippling Ln, Winter Park, FL 32789
Spacious tiled patio with folding glass doors, a pool, and comfortable outdoor seating at 301 Rippling Ln, Winter Park, FL 32789
On Market For 9 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3694

  • Year Built

    1958

  • $/SqFt

    $677

Contact us today to schedule a private tour. XCLUSIVE HOMES LLC.

Pended $2,495,000

Charming home with black and white striped awnings and a well manicured lawn at dusk at 140 Cortland Ave, Winter Park, FL 32789
Charming home with an American flag, striped awnings, and a brick walkway at 140 Cortland Ave, Winter Park, FL 32789
Bright entryway featuring hardwood floors, a staircase with white railing, and elegant decor at 140 Cortland Ave, Winter Park, FL 32789
On Market For 9 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    4168

  • Year Built

    1926

  • $/SqFt

    $599

Cortland Park - You’ll love the inviting ambiance of both this home and its vibrant Winter Park location. FLAT FEE MLS REALTY.

Home For Sale $925,000

Inviting light blue home features a curved driveway, well-kept landscaping, and mid-century modern architectural details at 625 Worthington Dr, Winter Park, FL 32789
A cozy light blue home showcasing a welcoming front porch with white chairs and mid-century modern decorative elements at 625 Worthington Dr, Winter Park, FL 32789
Charming front porch featuring comfortable seating, a decorative front door, and stylish accents at 625 Worthington Dr, Winter Park, FL 32789
On Market For 9 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2133

  • Year Built

    1958

  • $/SqFt

    $434

With the neighborhood rapidly evolving, many homes around this property are being torn down to make way for new, custom-built estates, including expansive 4,000 square foot homes valued at over $3 million. KELLY PRICE & COMPANY LLC.

Home For Sale $1,275,000

Modern home with white exterior, complemented by a brick driveway and manicured landscaping at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
Aerial view of a modern white home near a golf course with mature landscaping at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
Bright open-concept living room with modern furnishings flowing into a stylish kitchen at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 10 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2284

  • Year Built

    2015

  • $/SqFt

    $558

Don’t miss your chance to own this exceptional property in one of Winter Park’s most sought-after locations. Schedule your private showing today! RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $750,000

Aerial view of modern home adjacent to a lush golf course and featuring ample parking at 726 N Pennsylvania Ave, Winter Park, FL 32789
Modern kitchen featuring stainless steel appliances, a black marble backsplash and a stylish breakfast bar at 726 N Pennsylvania Ave, Winter Park, FL 32789
Contemporary kitchen with stainless steel appliances, sleek black cabinetry and tiled flooring at 726 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 10 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1167

  • Year Built

    2015

  • $/SqFt

    $643

Don’t miss this incredible opportunity in one of Winter Park’s most sought-after locations, Schedule your private showing today! RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $550,000

A scenic aerial view of a modern home with a golf course, railroad, and lush greenery in the neighborhood at 720 N Pennsylvania Ave, Winter Park, FL 32789
Open-concept living room with modern furniture, a ceiling fan, and an open view into the modern kitchen at 720 N Pennsylvania Ave, Winter Park, FL 32789
Bright living room with wood-look tile flooring, neutral sofa, pops of color, and contemporary decor at 720 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 10 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1115

  • Year Built

    2015

  • $/SqFt

    $493

Don’t miss this chance to own a modern, stylish home in the heart of Winter Park! Schedule your private showing today. RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $550,000

A bright and inviting blue home, showcasing a large covered porch and outdoor features at 423 Ololu Dr, Winter Park, FL 32789
A bright entryway features wood-look tile flooring, fresh paint and modern light fixture at 423 Ololu Dr, Winter Park, FL 32789
Modern kitchen featuring quartz countertops, new stainless steel appliances, and stylish pendant lighting at 423 Ololu Dr, Winter Park, FL 32789
On Market For 10 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1920

  • Year Built

    1981

  • $/SqFt

    $286

Contact us today for a private showing. AAA GLOBAL VENTURES PA.

Pended $399,900

Eat-in kitchen featuring white cabinets, an island, terracotta tile floors, and views of the backyard at 767 Baffie Ave, Winter Park, FL 32789
Spacious kitchen with terracotta tile floors, white cabinetry, black appliances, and a door to the backyard at 767 Baffie Ave, Winter Park, FL 32789
Bright dining area with terracotta tile floors, a round table, and a large window with views of the yard at 767 Baffie Ave, Winter Park, FL 32789
On Market For 10 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1132

  • Year Built

    1958

  • $/SqFt

    $353

Combining the perfect blend of modern updates and original character, this home is a must-see in the heart of Winter Park! GECKO REALTY, INC.

Home For Sale $1,350,000

Inviting front porch featuring a stylish door, sleek black shutters and a cozy seating area at 181 N Phelps Ave, Winter Park, FL 32789
Aerial view of a home featuring a long rectangular pool and mature landscaping at 181 N Phelps Ave, Winter Park, FL 32789
Backyard pool area with cabana, dining table, and lush greenery at 181 N Phelps Ave, Winter Park, FL 32789
On Market For 11 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3000

  • Year Built

    1948

  • $/SqFt

    $450

Sylvan Lake Shores - Additional House Benefits include: Remodeled living room ; Original wood fireplace ; New AC (2021) ; Tankless water heater 2021 ; Dual masters ; 4 full baths ; Insulated 2 car garage with exAC Garage ; New vinyl flooring ; Remodeled office / guest room with built-in cabinets ; Heated swimming pool ; Renovated backyard with artificial grass and summer kitchen (outdoor furniture negotiable) ; New detached office space w/ air conditioning ; Outdoor ambient lighting ; New alarm system ; All appliances will stay ; Extended Kitchen Island ; New sprinkler system ; Outdoor shed storage; Acclimate Attic ; New PVC Wood Deck ; Water filtration system in the kitchen ; Underground gas line for stovetop, water heater, and pool heater Located just minutes from Windsong, Park Avenue, Baldwin Park, top-rated schools (Brookshire, Glenridge, WPHS), parks, dining, and shopping, this home offers both charm and convenience. ORLANDO BROTHERS REAL ESTATE LLC.

Home For Sale $1,675,000

Waterfront homes featuring private docks and pools, situated on a picturesque lake at 607 Ellen Dr, Winter Park, FL 32789
Scenic lake view featuring a private dock and residents paddle boarding at 607 Ellen Dr, Winter Park, FL 32789
Elegant two-story house boasting contemporary design with a flat roof and vibrant landscaping at 607 Ellen Dr, Winter Park, FL 32789
On Market For 14 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2812

  • Year Built

    2025

  • $/SqFt

    $596

Last home available in the neighborhood and is priced well as this home will not last long! ! COMMUNITY REALTY ASSOCIATES.

Home For Sale $1,295,000

Aerial view of the home showcasing its gray roof, backyard space, and proximity to surrounding neighborhood at 1611 Chestnut Ave, Winter Park, FL 32789
Property highlighted by boundary lines showing its location and surrounding homes and well-manicured lawns at 1611 Chestnut Ave, Winter Park, FL 32789
Overhead image of a neighborhood featuring well-maintained homes, private pools, and mature landscaping at 1611 Chestnut Ave, Winter Park, FL 32789
On Market For 14 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2916

  • Year Built

    1973

  • $/SqFt

    $444

Lake Knowles Terrace - Perfectly positioned in a charming neighborhood, the property is near Lakemont Elementary, Phelps Park, and the YMCA, ensuring a vibrant community lifestyle PARK AVENUE REALTY LLC.

Pended $1,595,000

Charming pink home featuring stately white columns, a landscaped front yard, and tropical palm trees at 335 Beloit Ave, Winter Park, FL 32789
Welcoming foyer with neutral tile floors and chic decor that flows into the spacious living area at 335 Beloit Ave, Winter Park, FL 32789
Bright living room with a decorative fireplace, modern furnishings, and access to outdoor living space at 335 Beloit Ave, Winter Park, FL 32789
On Market For 15 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2420

  • Year Built

    1978

  • $/SqFt

    $659

Enjoy a NEW A/C unit (2024), new washer/dryer (2024), and one of the best locations in the City of Winter Park! ! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,195,000

Inviting single-story home with a brick driveway, lush lawn, and a charming terracotta-tiled roof at 1690 Oneco Ave, Winter Park, FL 32789
Beautiful single-story home featuring a well-manicured lawn, brick driveway, and a classic terracotta tile roof at 1690 Oneco Ave, Winter Park, FL 32789
Elegant foyer featuring arched entryways, a dark wood front door, neutral paint and travertine tile flooring at 1690 Oneco Ave, Winter Park, FL 32789
On Market For 15 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2703

  • Year Built

    1967

  • $/SqFt

    $442

Winter Park Heights - Just minutes from the shopping and dining district of Park Avenue in downtown Winter Park, this remarkable home offers the ideal blend of comfort, convenience and style. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $795,000

Lovely single-story house with a white exterior, attached garage, and green grass at 1037 N Virginia Ave, Winter Park, FL 32789
Beautiful single-story home featuring a white exterior, covered porch, and well-manicured landscaping at 1037 N Virginia Ave, Winter Park, FL 32789
Inviting covered front porch with decorative iron supports and black front door at 1037 N Virginia Ave, Winter Park, FL 32789
On Market For 15 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1101

  • Year Built

    1960

  • $/SqFt

    $722

Don’t miss this “one of kind – live your best Winter Park life” opportunity! KELLER WILLIAMS WINTER PARK.

Pended $425,000

Inviting front entrance with a quaint bench, lush landscaping, and vibrant blue exterior paint at 328 Lake Fair Ln, Winter Park, FL 32789
A close-up of the home's front door, featuring a dark finish and wood post accents at 328 Lake Fair Ln, Winter Park, FL 32789
Bright dining room with hardwood floors, modern fan, and view to adjacent rooms at 328 Lake Fair Ln, Winter Park, FL 32789
On Market For 15 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1485

  • Year Built

    1958

  • $/SqFt

    $286

Fairbanks Shores - Don’t miss the chance to own this lakefront gem—a perfect blend of historic charm, modern upgrades, and an unbeatable location. Schedule your private tour today! RE/MAX 200 REALTY.

Home For Sale $1,250,000

Inviting single-story home with lush landscaping, brick driveway, and a cozy front yard at 1585 Chestnut Ave, Winter Park, FL 32789
Attractive home showcasing neat landscaping, a gray garage door, and a clay tile roof at 1585 Chestnut Ave, Winter Park, FL 32789
Bright dining room featuring a ceiling fan, large windows, and unique tile flooring at 1585 Chestnut Ave, Winter Park, FL 32789
On Market For 14 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2220

  • Year Built

    1959

  • $/SqFt

    $563

Lake Knowles Terrace - Don’t miss your chance to own a piece of Winter Parks most desirable neighborhood! KELLER WILLIAMS WINTER PARK.

Pended $949,900

Inviting front entrance with a lush, verdant pergola, and a security system at 533 Balmoral Rd, Winter Park, FL 32789
Up-close view of a stunning wooden front door surrounded by lush greenery and stone accents at 533 Balmoral Rd, Winter Park, FL 32789
Cozy covered patio featuring wood-look tile flooring, a unique chair, and ample natural light at 533 Balmoral Rd, Winter Park, FL 32789
On Market For 16 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1900

  • Year Built

    1957

  • $/SqFt

    $500

Upgrades include: New Paint & Finishes, Modernized Bathrooms (New vanities and a renovated master shower) Custom Master Closet, New Interior Doors and windows, New Upgraded HVAC System (2021), Tankless gas hot water heater, Roof (2020), HVAC (2021) Exterior Stone Façade, Updated Landscaping & Outdoor Living spaces (Lanai, pergola, and firepit) irrigation, New Front Door & Exterior Lighting, Solar Panels (paid off) Security System Ready (Wired for easy setup) Upgraded Laundry Room (Added storage, tile, and cabinetry) CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $2,395,000

Modern home showcases a two-car garage, gravel driveway, and lush, green landscaping at 2412 Chantilly Ave, Winter Park, FL 32789
Elegant entryway featuring a modern glass door, stone path, and stylish landscaping at 2412 Chantilly Ave, Winter Park, FL 32789
Bright foyer with hardwood floors and a modern glass door leading to the exterior at 2412 Chantilly Ave, Winter Park, FL 32789
On Market For 17 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4506

  • Year Built

    2024

  • $/SqFt

    $532

Winter Park Village - Perfectly positioned in a coveted Winter Park local, near top-rated schools and just moments from Park Avenue’s upscale shopping and dining, this exceptional residence offers the pinnacle of contemporary luxury living. COMPASS FLORIDA, LLC.

Pended $825,000

Reduced By $74,000

Single-story home with a carport and a tidy front lawn offers curb appeal at 1811 Oneco Ave, Winter Park, FL 32789
Aerial view of a home with a large, private backyard oasis and lush greenery at 1811 Oneco Ave, Winter Park, FL 32789
Aerial view of a home nestled in a tranquil neighborhood surrounded by mature trees at 1811 Oneco Ave, Winter Park, FL 32789
On Market For 16 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1348

  • Year Built

    1972

  • $/SqFt

    $612

Flora Park - Great Wp Schools. Survey Available In Attachments. FANNIE HILLMAN & ASSOCIATES.

Pended $2,200,000

Stately two-story home boasts a clay tile roof, lush landscaping, and a long, curved driveway at 1446 Berkshire Ave, Winter Park, FL 32789
Close up shows the home's architectural details and manicured landscaping with towering palms at 1446 Berkshire Ave, Winter Park, FL 32789
Charming facade features a secure gated entry, arched windows, and an attached two-car garage at 1446 Berkshire Ave, Winter Park, FL 32789
On Market For 19 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4612

  • Year Built

    1925

  • $/SqFt

    $477

With its prime Winter Park location, exceptional privacy, and resort-style amenities, this remarkable home offers the perfect blend of style, comfort, and convenience in one of Winter Park’s most desirable neighborhoods. SERHANT.

Home For Sale $1,295,000

Inviting single-story home with a white exterior, well-manicured landscaping, and a large shade tree at 1932 Temple Dr, Winter Park, FL 32789
Charming single-story home with lush landscaping and a grand shade tree at twilight at 1932 Temple Dr, Winter Park, FL 32789
Bright and airy living room featuring a large white sectional, wood floors, and an open layout at 1932 Temple Dr, Winter Park, FL 32789
On Market For 22 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2432

  • Year Built

    1952

  • $/SqFt

    $532

Lake Knowles Terrace - A great investment opportunity to live among the finest homes in Winter Park and in well-established neighborhood providing a lifestyle like no other. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $534,900

Inviting two-story home with a well-kept lawn and quaint pathway leading to the front porch at 1481 Harmon Ave, Winter Park, FL 32789
Welcoming front porch featuring fresh exterior paint and bright windows at 1481 Harmon Ave, Winter Park, FL 32789
Bright living room with hardwood floors, white walls, and decorative furnishings at 1481 Harmon Ave, Winter Park, FL 32789
On Market For 22 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1900

  • Year Built

    1926

  • $/SqFt

    $282

Lawndale - Don’t miss out on this rare opportunity—schedule your private showing today! KELLER WILLIAMS WINTER PARK.

Pended $3,295,000

White two-story house with a three-car garage and manicured lawn at 100 E Rockwood Way, Winter Park, FL 32789
Two-story white house with black accents and a walkway to the front door at 100 E Rockwood Way, Winter Park, FL 32789
Bright and spacious entryway with elegant staircase and hardwood floors at 100 E Rockwood Way, Winter Park, FL 32789
On Market For 22 Days
  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    4304

  • Year Built

    2020

  • $/SqFt

    $766

Charmont - A rare opportunity to own a turnkey masterpiece that offers the ideal balance of comfort style, and exceptional entertainment spaces. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,950,000

Elegant entryway with hardwood floors, chandelier, and staircase at 622 Penn Pl, Winter Park, FL 32789
Spacious living room with hardwood floors, fireplace, and French doors at 622 Penn Pl, Winter Park, FL 32789
Open living room with hardwood floors and views into kitchen at 622 Penn Pl, Winter Park, FL 32789
On Market For 25 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2767

  • Year Built

    2001

  • $/SqFt

    $705

Don’t miss your chance to make this exceptional property your next home! COMMUNITY REALTY ASSOCIATES.

Pended $3,130,000

Stunning contemporary home at night, featuring gray brick and a landscaped yard at 210 E Lake Sue Ave, Winter Park, FL 32789
Modern front entry with glass door, gray brick, and landscaping at 210 E Lake Sue Ave, Winter Park, FL 32789
Elegant entryway with wood floors, high ceilings, and built-in wet bar at 210 E Lake Sue Ave, Winter Park, FL 32789
On Market For 26 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4188

  • Year Built

    2025

  • $/SqFt

    $747

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

Home For Sale $1,995,000

Elegant entryway with checkered floor and unique decor at 817 Antonette Ave, Winter Park, FL 32789
Green striped sitting room with French doors opening to sunroom at 817 Antonette Ave, Winter Park, FL 32789
Green striped sitting room with ample natural light and unique decor at 817 Antonette Ave, Winter Park, FL 32789
On Market For 26 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3971

  • Year Built

    1990

  • $/SqFt

    $502

College Place - Don't miss the opportunity to schedule a private viewing of this unique, one-of-a-kind treasure! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,279,000

View of house featuring a tile roof, well-manicured lawn, mature trees, and a paved driveway leading to the garage at 141 Oakwood Way, Winter Park, FL 32789
Close up of home's entry featuring a blue double door, manicured bushes, walkway, and exterior accent lighting at 141 Oakwood Way, Winter Park, FL 32789
Bright dining room with hardwood floors and chandelier at 141 Oakwood Way, Winter Park, FL 32789
On Market For 28 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3909

  • Year Built

    2015

  • $/SqFt

    $583

Charmont - This is more than a home—it’s an expression of refined living and timeless design. Schedule your private tour today! MAINFRAME REAL ESTATE.

Home For Sale $2,119,000

Modern kitchen with white cabinets, a large island, and stainless steel appliances at 785 N Phelps Ave, Winter Park, FL 32789
Spacious living area featuring a sectional sofa and a large TV at 785 N Phelps Ave, Winter Park, FL 32789
Bright bedroom with a comfortable bed and access to the backyard at 785 N Phelps Ave, Winter Park, FL 32789
On Market For 27 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    2964

  • Year Built

    2025

  • $/SqFt

    $715

Comstock Park - Conveniently located just 1.9 miles or 8 minutes from the vibrant Park Avenue, you'll have easy access to boutique shopping and fine dining. Call today for more information. COMPASS FLORIDA, LLC.

Pended $2,100,000

Brick walkway, lush landscaping and a charming house exterior at 140 Dana Way, Winter Park, FL 32789
Brick house with metal roof, landscaping, and a gravel driveway at 140 Dana Way, Winter Park, FL 32789
Housetop view showing the home's size and lot in a wooded area at 140 Dana Way, Winter Park, FL 32789
On Market For 28 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    3441

  • Year Built

    2011

  • $/SqFt

    $610

Charmont - The gated driveway and fully fenced property ensure security and exclusivity, all within one of Winter Park’s most sought-after neighborhoods.This is a rare opportunity to own a luxurious estate in a prestigious Winter Park location, surrounded by the beauty of the Lake Sue neighborhodd and just moments from the best shopping, dining, and cultural experiences the area has to offer. OLDE TOWN BROKERS INC.

Home For Sale $1,950,000

Elegant two-story house with white exterior, gray roof, and a manicured lawn at 1470 Place Picardy, Winter Park, FL 32789
Bright entryway with hardwood floors and a classic white door at 1470 Place Picardy, Winter Park, FL 32789
Spacious Gathering room with hardwood floors, built-in shelving, and fireplace at 1470 Place Picardy, Winter Park, FL 32789
On Market For 29 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4227

  • Year Built

    2003

  • $/SqFt

    $461

Fontainebleau - Please see attachments for the full list of improvements. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $389,900

Reduced By $9,100

Cute light blue house with a walkway leading to the front door at 1930 Albert Lee Pkwy, Winter Park, FL 32789
Ranch style home with a light blue exterior and landscaped yard at 1930 Albert Lee Pkwy, Winter Park, FL 32789
Light blue house with a white garage and a mailbox at 1930 Albert Lee Pkwy, Winter Park, FL 32789
On Market For 29 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1262

  • Year Built

    1955

  • $/SqFt

    $309

Albert Lee Ridge - Don’t miss out on this opportunity to own in one of Central Florida’s most desirable neighborhoods. FLORIDA ONE REAL ESTATE LLC.

Home For Sale $1,380,000

Bright entryway with a large, black curio cabinet and white door at 1400 S Pennsylvania Ave, Winter Park, FL 32789
Open concept dining room with a view of the kitchen and living room at 1400 S Pennsylvania Ave, Winter Park, FL 32789
Modern dining room features an oval table, rattan light, and neutral decor at 1400 S Pennsylvania Ave, Winter Park, FL 32789
On Market For 30 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2060

  • Year Built

    1962

  • $/SqFt

    $670

Banks Colonial Estates - Be sure and schedule a viewing. JACK KELLER INC.

Home For Sale $408,500

Reduced By $10,000

Quaint single-story home showcasing a brick facade, green lawn, and mature trees at 942 Hanover Ave, Winter Park, FL 32789
Bright, open living room featuring hardwood floors, neutral walls, and large windows overlooking the lush yard at 942 Hanover Ave, Winter Park, FL 32789
Bright bedroom features hardwood floors, a ceiling fan, and multiple windows offering natural light at 942 Hanover Ave, Winter Park, FL 32789
On Market For 30 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1345

  • Year Built

    1956

  • $/SqFt

    $304

Room dimensions are: Living Room — 19'x12' Kitchen — 10'x6 1/2' Master BR — 16'x11' 2nd BR — 13'x11' Sunroom — 12'x12 1/2' Dining — 10x9 1/2' HOME SOLD REALTY LLC.

Home For Sale $1,299,990

Modern single story home with attached garage and landscaped lawn at 2258 E Howard Dr, Winter Park, FL 32789
Updated mid century modern home with attached garage and lush landscaping at 2258 E Howard Dr, Winter Park, FL 32789
Modern garage with white door and wood-like accents at 2258 E Howard Dr, Winter Park, FL 32789
On Market For 31 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2747

  • Year Built

    1953

  • $/SqFt

    $473

Northwood Terrace - Zoned for top-rated Audubon K-8 and Winter Park High School, this neighborhood is a true gem, benefiting from its prime location and excellent schools, in an area experiencing rapid transformation. NAIM REAL ESTATE LLC.

Home For Sale $1,759,000

Spacious living room with large windows, comfortable seating, and a modern aesthetic at 1660 Walnut Ave, Winter Park, FL 32789
Modern kitchen with gray cabinetry, center island, and stainless steel appliances at 1660 Walnut Ave, Winter Park, FL 32789
Bright bedroom with a ceiling fan, neutral color palette, and stylish decor at 1660 Walnut Ave, Winter Park, FL 32789
On Market For 32 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2172

  • Year Built

    2025

  • $/SqFt

    $810

Lake Knowles Terrace - Don’t miss the opportunity to make this stunning Winter Park home yours. COMPASS FLORIDA, LLC.

Pended $475,000

Modern kitchen featuring dark cabinetry and granite countertops at 1937 Eland Ave, Winter Park, FL 32789
Bright and airy living room with hardwood floors and open concept at 1937 Eland Ave, Winter Park, FL 32789
Modern kitchen with dark wood cabinets and stainless steel appliances at 1937 Eland Ave, Winter Park, FL 32789
On Market For 31 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1560

  • Year Built

    1957

  • $/SqFt

    $304

Lake Bell Terrace - In less than 10 minutes, you can get from this property to Park Avenue (6 minutes), Hannibal Square (7 minutes), Winter Park Village (5 minutes), Edgewater Drive (7 minutes), I-4 (3 minutes), Rollins College (10 minutes), and Lake Lily Park (6 minutes). MILLER GRANT AND COMPANY.

Pended $1,500,000

Cute one-story house with a spacious lawn at 747 Mcintyre Ave, Winter Park, FL 32789
Cute one-story house with a spacious lawn at 747 Mcintyre Ave, Winter Park, FL 32789
Cute one-story house with a spacious lawn at 747 Mcintyre Ave, Winter Park, FL 32789
On Market For 32 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1457

  • Year Built

    1950

  • $/SqFt

    $1,030

Opportunities like this are a rare find in Winter Park! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,995,000

Elegant front entry with a wood door, flanked by light blue shutters at 1400 Place Picardy, Winter Park, FL 32789
Bright and spacious entryway with hardwood floors and blue patterned wallpaper at 1400 Place Picardy, Winter Park, FL 32789
Open dining room with hardwood floors, blue accents and chandelier at 1400 Place Picardy, Winter Park, FL 32789
On Market For 36 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4411

  • Year Built

    2008

  • $/SqFt

    $679

Fontainebleau - Call today to schedule your private showing. You will Love living here! PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $599,900

Reduced By $50,100

Modern two-story house with gray siding, paver driveway, and landscaped lawn at 1875 Staunton Ave, Winter Park, FL 32789
Modern two-story house with gray siding, paver driveway, and landscaped lawn at 1875 Staunton Ave, Winter Park, FL 32789
Inviting front entrance with gray siding, paver walkway, and potted plants at 1875 Staunton Ave, Winter Park, FL 32789
On Market For 36 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2036

  • Year Built

    1954

  • $/SqFt

    $295

Karolina On Killarney - You are less than 2 miles from Park Avenue. THE AGENCY ORLANDO.

Home For Sale $579,000

Reduced By $10,000

Relaxing backyard oasis featuring a refreshing pool with patio furniture at 1424 Cavendish Rd, Winter Park, FL 32789
Charming bungalow with lush landscaping, driveway, and a green exterior at 1424 Cavendish Rd, Winter Park, FL 32789
House exterior with a green facade, black garage door, and manicured lawn at 1424 Cavendish Rd, Winter Park, FL 32789
On Market For 36 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1132

  • Year Built

    1949

  • $/SqFt

    $511

Don’t miss the opportunity to make this Gem your new home! KEYSEEKERS REAL ESTATE.

Home For Sale $414,000

Reduced By $17,000

Bright living room with hardwood floors, comfy seating, and modern decor at 2111 Staunton Ave, Winter Park, FL 32789
Spacious living area showcasing hardwood floors and ample natural light at 2111 Staunton Ave, Winter Park, FL 32789
Spacious bedroom with light walls, hardwood floors, and built-in storage at 2111 Staunton Ave, Winter Park, FL 32789
On Market For 36 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1292

  • Year Built

    1954

  • $/SqFt

    $320

This property is a true gem, offering comfort and sophistication. OPENDOOR BROKERAGE LLC.

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 407-278-2057 and speak with one of our real estate consultants.

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