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View 253 Winter Park Florida Homes for Sale

Home For Sale $2,279,000

Charming two-story home featuring a tile roof, a pergola over the garage, and a lush landscaped yard at 141 Oakwood Way, Winter Park, FL 32789
View Details 58 Photos
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 21 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

Two-story modern home with light-colored facade, wood garage doors, and landscaping at 785 N Phelps Ave, Winter Park, FL 32789
View Details 5 Photos
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 21 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 house with a metal roof, lush landscaping, and a brick walkway at 140 Dana Way, Winter Park, FL 32789
View Details 46 Photos
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 21 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

Two-story house with white exterior, gray roof, and landscaped lawn at 1470 Place Picardy, Winter Park, FL 32789
View Details 27 Photos
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 22 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 $499,000

Updated home exterior featuring a large driveway and manicured lawn at 2247 King Edwards Ct, Winter Park, FL 32792
View Details 33 Photos
Inviting front entry with a charming stone pathway and landscaping at 2247 King Edwards Ct, Winter Park, FL 32792
Bright hallway with hardwood floors and access to other rooms at 2247 King Edwards Ct, Winter Park, FL 32792
Spacious living room showcasing hardwood floors and a ceiling fan at 2247 King Edwards Ct, Winter Park, FL 32792
On Market For 22 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2129

  • Year Built

    1968

  • $/SqFt

    $234

Winter Woods - Schedule your private showing today, take the opportunity to own a piece of Winter Park Paradise in the desirable Sunshine State! EMPIRE NETWORK REALTY.

Pended $1,750,000

Stunning two-story home with stone accents and a tile roof at 2185 Talman Court, Winter Park, FL 32792
View Details 54 Photos
Three-car garage with paver driveway and stone accents at 2185 Talman Court, Winter Park, FL 32792
Beautiful two-story home with stone and stucco exterior at 2185 Talman Court, Winter Park, FL 32792
Grand home with stone and stucco exterior, landscaped yard at 2185 Talman Court, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 9 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4760

  • Year Built

    2008

  • $/SqFt

    $368

Additional highlights include a generator, outdoor shower, zoned AC, tankless water heaters, Lutron light control system, AC Nest control system, outdoor security cameras, Lightening protection, and a spacious three-car side/rear-entry garage. WELCOME HOME! FANNIE HILLMAN & ASSOCIATES.

Pended $1,175,000

Charming lakefront property with a dock, perfect for enjoying water activities at 3818 Kinsley Place, Winter Park, FL 32792
View Details 26 Photos
Two-story house with a wrap-around porch and large windows at 3818 Kinsley Place, Winter Park, FL 32792
Two-story house with a wrap-around porch and large windows at 3818 Kinsley Place, Winter Park, FL 32792
Two-story house with a wrap-around porch and large windows at 3818 Kinsley Place, Winter Park, FL 32792
On Market For 21 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3613

  • Year Built

    1989

  • $/SqFt

    $325

Bear Gully Bay - Enjoy lakefront living at its finest, with direct access to Bear Gully Lake for boating, fishing, skiing or simply enjoying the view from the backyard. PREMIER SOTHEBY'S INTL. REALTY.

Pended $434,900

Charming single-story home with blue accents and a well-manicured lawn at 2076 Leanne Ct, Winter Park, FL 32792
View Details 19 Photos
House exterior showcasing a well-maintained lawn and blue garage door at dusk at 2076 Leanne Ct, Winter Park, FL 32792
Brick walkway leading to the front door of a renovated house at 2076 Leanne Ct, Winter Park, FL 32792
Light-filled dining area with laminate wood floors and kitchen access at 2076 Leanne Ct, Winter Park, FL 32792
On Market For 22 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1729

  • Year Built

    1969

  • $/SqFt

    $252

Eastbrook - Schedule a tour today—your dream home awaits! SAND DOLLAR REALTY GROUP INC.

Home For Sale $399,900

House exterior with a two car garage and landscaping at 3131 Ash Park Loop, Winter Park, FL 32792
View Details 72 Photos
Aerial view of a house and surrounding neighborhood at 3131 Ash Park Loop, Winter Park, FL 32792
House exterior featuring a two-car garage and landscaping at 3131 Ash Park Loop, Winter Park, FL 32792
Brick home with a red front door and covered porch at 3131 Ash Park Loop, Winter Park, FL 32792
On Market For 23 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1408

  • Year Built

    1986

  • $/SqFt

    $284

STRICKLAND REALTY GROUP INC.

Home For Sale $399,000

Cute one-story home with a red door and well-manicured lawn at 3377 Hamlet Loop, Winter Park, FL 32792
View Details 28 Photos
Idyllic lake view with wooden dock and gazebo in a lush green landscape at 3377 Hamlet Loop, Winter Park, FL 32792
Sparkling community pool surrounded by lounge chairs and lush landscaping at 3377 Hamlet Loop, Winter Park, FL 32792
Cozy living room featuring a fireplace, vaulted ceilings, and comfortable seating at 3377 Hamlet Loop, Winter Park, FL 32792
On Market For 22 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1397

  • Year Built

    1994

  • $/SqFt

    $286

Villas Of Casselberry - Brand New Roof - 2024, Hvac - 2024, Water Heater - 2017. KELLER WILLIAMS WINTER PARK.

Home For Sale $389,900

Reduced By $9,100

Light blue house with palm trees, walkway, and driveway at 1930 Albert Lee Pkwy, Winter Park, FL 32789
View Details 76 Photos
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 23 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

Beautiful home with a large front yard, paved driveway and lush landscaping at 1400 S Pennsylvania Ave, Winter Park, FL 32789
View Details 50 Photos
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 23 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 $569,000

Reduced By $6,000

White house with black garage door, landscaping, and long driveway at 2779 Prince John Rd, Winter Park, FL 32792
View Details 36 Photos
Teal front door and whitewashed brick exterior at 2779 Prince John Rd, Winter Park, FL 32792
Bright living room with hardwood floors and modern furniture at 2779 Prince John Rd, Winter Park, FL 32792
Cozy sitting area with two armchairs and a brown ottoman at 2779 Prince John Rd, Winter Park, FL 32792
On Market For 22 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1579

  • Year Built

    1962

  • $/SqFt

    $360

With its ideal blend of interior luxury and expansive outdoor living, it’s the perfect place to call home. HVAC - 2023, ROOF - 2022 KELLER WILLIAMS WINTER PARK.

Home For Sale $550,000

Reduced By $35,000

Ranch style home with gray exterior, landscaped lawn, and attached garage at 2823 Cady Way, Winter Park, FL 32792
View Details 26 Photos
Living room with hardwood floors, leather couches, and a large piece of art at 2823 Cady Way, Winter Park, FL 32792
Bright living room with hardwood floors, leather furniture, and view into dining room at 2823 Cady Way, Winter Park, FL 32792
Living room with hardwood floors, access to screened patio, and built-in shelving at 2823 Cady Way, Winter Park, FL 32792
On Market For 22 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1688

  • Year Built

    1965

  • $/SqFt

    $326

Easy access to Winter Park shopping, dining and restaurants as well as the Orlando International airport, UCF and Rollins college. Schedule your showing today! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $408,500

Reduced By $10,000

Charming single-story home with a brick accent, green lawn, and a long, inviting driveway at 942 Hanover Ave, Winter Park, FL 32789
View Details 32 Photos
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 23 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 $389,000

Single-story house with attached garage and driveway at 5331 Binnacle Ct, Winter Park, FL 32792
View Details 17 Photos
Living room featuring light beige leather furniture and tile floors at 5331 Binnacle Ct, Winter Park, FL 32792
Dining area with wooden table and hutch at 5331 Binnacle Ct, Winter Park, FL 32792
Simple kitchen with light wood cabinets and appliances at 5331 Binnacle Ct, Winter Park, FL 32792
On Market For 23 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1242

  • Year Built

    1973

  • $/SqFt

    $313

Woodcrest - You will love this big yard and NO HOA fees ! Very easy to show ! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $1,299,990

Aerial view of a single story home with a pool and large backyard at 2258 E Howard Dr, Winter Park, FL 32789
View Details 48 Photos
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 24 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 $459,900

Reduced By $19,100

Charming single-story home featuring a well-manicured lawn and a welcoming front porch with brick accents at 2207 Winter Woods Blvd, Winter Park, FL 32792
View Details 45 Photos
Attractive home exterior showcases a brick pathway leading to the front door, complemented by green landscaping at 2207 Winter Woods Blvd, Winter Park, FL 32792
Bird's eye view of single-Gathering home and neighborhood at 2207 Winter Woods Blvd, Winter Park, FL 32792
Charming front door with decorative details and a welcoming porch light at 2207 Winter Woods Blvd, Winter Park, FL 32792
On Market For 24 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1710

  • Year Built

    1969

  • $/SqFt

    $269

Winter Woods - The perfect blend of space, convenience, and flexibility—a true must-see. Schedule your private showing today! COLDWELL BANKER REALTY.

Home For Sale $1,759,000

Two-story home with modern design, three-car garage, and landscaped front yard at 1660 Walnut Ave, Winter Park, FL 32789
View Details 9 Photos
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 25 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

Charming bungalow with lush landscaping and a spacious yard at 1937 Eland Ave, Winter Park, FL 32789
View Details 17 Photos
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 23 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

Inviting front porch with blue door and screened enclosure at 747 Mcintyre Ave, Winter Park, FL 32789
View Details 44 Photos
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 25 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 $795,000

White single story home with dark gray garage door and landscaped lawn at 607 Dunblane Dr, Winter Park, FL 32792
View Details 41 Photos
Modern single story home with white exterior and dark gray garage at 607 Dunblane Dr, Winter Park, FL 32792
Newly renovated single-story home with a spacious lawn at 607 Dunblane Dr, Winter Park, FL 32792
Updated single story home with a large tree in the front yard at 607 Dunblane Dr, Winter Park, FL 32792
On Market For 26 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2046

  • Year Built

    1964

  • $/SqFt

    $389

Kenilworth Shores - Take advantage of this opportunity to own a beautifully renovated home in one of Winter Park's most sought-after neighborhoods—schedule your showing today! NETWORTH REALTY OF ORLANDO, LLC.

Pended $370,000

Pink house with white garage door and landscaping at 3890 Waterview Loop, Winter Park, FL 32792
View Details 28 Photos
Living room with hardwood floors, a couch and a coffee table at 3890 Waterview Loop, Winter Park, FL 32792
Dining room with hardwood floors and a wooden table at 3890 Waterview Loop, Winter Park, FL 32792
Living room with hardwood floors, a couch and end tables at 3890 Waterview Loop, Winter Park, FL 32792
On Market For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1527

  • Year Built

    1991

  • $/SqFt

    $242

Autumn Glen - Don’t miss your chance to own a home in one of Central Florida’s most desirable areas at an UNBEATABLE VALUE. KELLER WILLIAMS WINTER PARK.

Home For Sale $2,995,000

A charming two-story home with light blue shutters and manicured lawn at 1400 Place Picardy, Winter Park, FL 32789
View Details 48 Photos
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 29 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
View Details 24 Photos
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 29 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

Inviting front porch with patterned tile, wooden post, and a charming wreath at 1424 Cavendish Rd, Winter Park, FL 32789
View Details 47 Photos
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 29 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 $420,000

Reduced By $11,000

Charming yellow house with a brick driveway and well-manicured lawn at 2111 Staunton Ave, Winter Park, FL 32789
View Details 23 Photos
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 29 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1292

  • Year Built

    1954

  • $/SqFt

    $325

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

Home For Sale $379,000

Reduced By $6,000

Newly renovated home with white exterior, brown garage door, and landscaped yard at 1562 Lawndale Cir, Winter Park, FL 32792
View Details 42 Photos
Newly renovated home with white exterior, brown garage door, and landscaped yard at 1562 Lawndale Cir, Winter Park, FL 32792
Newly renovated home with white exterior, brown garage door, and landscaped yard at 1562 Lawndale Cir, Winter Park, FL 32792
Newly renovated home with white exterior, brown accents, and landscaped yard at 1562 Lawndale Cir, Winter Park, FL 32792
On Market For 30 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1118

  • Year Built

    1986

  • $/SqFt

    $339

Country Lane - AC and appliances all new in 2024! TERZA REAL ESTATE.

Home For Sale $1,599,900

Two-story home with a modern design, dark brown garage doors, and landscaping at 1417 Miller Ave, Winter Park, FL 32789
View Details 4 Photos
Home with a pool, outdoor kitchen, and relaxing lounge area at 1417 Miller Ave, Winter Park, FL 32789
Ground floor plan showcasing an open layout with a large living room and kitchen at 1417 Miller Ave, Winter Park, FL 32789
Second floor plan featuring three bedrooms, two bathrooms and a loft at 1417 Miller Ave, Winter Park, FL 32789
On Market For 30 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3312

  • Year Built

    2025

  • $/SqFt

    $483

No HOA fees and just moments from Publix, Trader Joe’s, Park Avenue, Mills/50, the Science Center, Winter Park Events Center, Advent Health and a fantastic array of restaurants and coffee shops. CORCORAN PREMIER REALTY.

Home For Sale $639,999

Reduced By $10,001

Stunning curb appeal! This home features a two-car garage and a beautifully landscaped yard at 1401 Lone Feather Trl, Winter Park, FL 32792
View Details 49 Photos
Modern kitchen with white cabinets, stainless steel appliances, and quartz countertops at 1401 Lone Feather Trl, Winter Park, FL 32792
Open concept kitchen boasts white cabinets, stainless steel appliances, and an island at 1401 Lone Feather Trl, Winter Park, FL 32792
Private backyard with a spacious patio and lush green lawn at 1401 Lone Feather Trl, Winter Park, FL 32792
On Market For 29 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1770

  • Year Built

    2022

  • $/SqFt

    $362

Convenience is at your doorstep with Park Maitland Preschool, Kelly’s Ice Cream and Foxtail Coffee right at the neighborhood’s entrance. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $620,000

Reduced By $29,000

Charming remodeled home with modern exterior and landscaped lawn at 631 Callahan St, Winter Park, FL 32789
View Details 37 Photos
Modern house exterior featuring a white facade, black accents, and a landscaped front yard at 631 Callahan St, Winter Park, FL 32789
Updated home with modern exterior and beautiful landscaping at 631 Callahan St, Winter Park, FL 32789
Charming house exterior with a lush green lawn and beautiful landscaping at 631 Callahan St, Winter Park, FL 32789
On Market For 29 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1751

  • Year Built

    1950

  • $/SqFt

    $354

Carver Town - Come see it for yourself – this is luxury living at its finest. CORCORAN PREMIER REALTY.

Home For Sale $649,000

Mid-century ranch home with carport and well-manicured lawn at 2100 Suffield Dr, Winter Park, FL 32792
View Details 46 Photos
House with pool and large lot, desirable location at 2100 Suffield Dr, Winter Park, FL 32792
Inviting rectangular pool with patio and tropical landscaping at 2100 Suffield Dr, Winter Park, FL 32792
Spacious living room with brick fireplace and comfortable seating at 2100 Suffield Dr, Winter Park, FL 32792
On Market For 31 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1807

  • Year Built

    1960

  • $/SqFt

    $359

Don't miss this chance to make this "Great Bones" home your own! RE/MAX 200 REALTY.

Home For Sale $568,000

Reduced By $21,000

Brick ranch house with attached garage and landscaped lawn at 2855 Cady Way, Winter Park, FL 32792
View Details 35 Photos
Brick ranch house with red front door and landscaped yard at 2855 Cady Way, Winter Park, FL 32792
One-story home with gray siding, landscaping, and a curved driveway at 2855 Cady Way, Winter Park, FL 32792
Modern kitchen with stainless steel appliances, granite counters, and white cabinets at 2855 Cady Way, Winter Park, FL 32792
On Market For 32 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1736

  • Year Built

    1964

  • $/SqFt

    $327

Call today to schedule your showing! GLOBAL PROPERTIES SALES & MGMT.

Home For Sale $425,000

Tan house with a two-car garage and mature landscaping at 1309 Paradise Ln, Winter Park, FL 32792
View Details 39 Photos
Bright living room with fireplace,tile flooring and view to kitchen and backyard at 1309 Paradise Ln, Winter Park, FL 32792
Spacious living room with tiled floors and neutral color palette at 1309 Paradise Ln, Winter Park, FL 32792
Spacious living room with tiled floors and neutral color palette at 1309 Paradise Ln, Winter Park, FL 32792
On Market For 32 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1606

  • Year Built

    1984

  • $/SqFt

    $265

Conveniently located, this home offers easy access to nearby shopping, dining and major roadways and is in the A Rated Lake Howell High school zone. COLDWELL BANKER REALTY.

Pended $420,000

Newly renovated home with a modern exterior and landscaped lawn at 1025 Early Ave, Winter Park, FL 32789
View Details 29 Photos
Newly renovated home with a modern exterior and driveway at 1025 Early Ave, Winter Park, FL 32789
Modern front door with sleek black finish and sidelights at 1025 Early Ave, Winter Park, FL 32789
Open concept living area with modern furniture and hardwood floors at 1025 Early Ave, Winter Park, FL 32789
On Market For 30 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1333

  • Year Built

    1956

  • $/SqFt

    $315

Albert Lee Ridge - With a fresh, move-in ready feel and a prime location, this is a must-see. Schedule your showing today! SAND DOLLAR REALTY GROUP INC.

Pended $385,000

Single story home with well-maintained landscaping and a paved driveway at 2100 Shirewood Ct, Winter Park, FL 32792
View Details 19 Photos
Living room features a comfy sofa and a view into the dining area at 2100 Shirewood Ct, Winter Park, FL 32792
Living room with blue floral sofas and a view of the dining area at 2100 Shirewood Ct, Winter Park, FL 32792
Spacious living room with floral sofas and a wood coffee table at 2100 Shirewood Ct, Winter Park, FL 32792
On Market For 31 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1427

  • Year Built

    1986

  • $/SqFt

    $270

Cedar Ridge - This house is packed with potential —don’t miss this one! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $4,500,000

Two-story brick home with dark brown accents, landscaping, and a two-car garage at 702 Via Bella, Winter Park, FL 32789
View Details 7 Photos
Brick home with herringbone driveway, landscaping, and a two-car garage at 702 Via Bella, Winter Park, FL 32789
Two-story home with a two-car garage and landscaped yard, showcasing a beautiful brick exterior at 702 Via Bella, Winter Park, FL 32789
Two-story brick home with dark brown accents, landscaping, and a two-car garage at 702 Via Bella, Winter Park, FL 32789
On Market For 32 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3720

  • Year Built

    2025

  • $/SqFt

    $1,210

The perfect home for those seeking luxurious living and refined elegance. FLORIDIAN REALTY GROUP LLC.

Pended $769,000

Reduced By $30,000

Two-story gray house with black shutters, landscaped yard, and a walkway at 1375 Suffolk Rd, Winter Park, FL 32789
View Details 29 Photos
Two-story gray house with black shutters, nicely landscaped front yard at 1375 Suffolk Rd, Winter Park, FL 32789
Two-story gray house with black shutters, landscaped yard, at dusk at 1375 Suffolk Rd, Winter Park, FL 32789
Two-story gray house with black shutters, landscaped yard, and driveway at 1375 Suffolk Rd, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 30 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2548

  • Year Built

    1940

  • $/SqFt

    $302

Don’t miss your chance to see it - schedule your showing today! MAINFRAME REAL ESTATE.

Pended $399,000

White single-story house with a two-car garage and well-manicured landscaping at 5427 Albert Dr, Winter Park, FL 32792
View Details 38 Photos
White single-story house with a two-car garage and neatly landscaped front yard at 5427 Albert Dr, Winter Park, FL 32792
White single-story house with a two-car garage and lush landscaping at 5427 Albert Dr, Winter Park, FL 32792
Bright entryway with a full-length mirror, bench, and coat rack at 5427 Albert Dr, Winter Park, FL 32792
On Market For 32 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1306

  • Year Built

    1978

  • $/SqFt

    $306

Howell Branch Woods - All disclosures and documentation will be provided transparently to ensure a smooth and professional process for buyers and their agents. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $1,250,000

Charming two-story home with a large front porch and brick driveway at 567 Osceola Ave, Winter Park, FL 32789
View Details 39 Photos
Two-story home with a wrap-around porch, and manicured hedges at 567 Osceola Ave, Winter Park, FL 32789
Two-story house with a wrap-around porch and brick driveway at 567 Osceola Ave, Winter Park, FL 32789
Two-story house with a wrap-around porch and brick driveway at 567 Osceola Ave, Winter Park, FL 32789
On Market For 33 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2651

  • Year Built

    1912

  • $/SqFt

    $472

Osceola Court - Parking is easy with a circular driveway, carport and a 2-car garage with plenty of storage. Call today for an appointment! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $429,900

Reduced By $10,000

One-story house with a gray exterior, attached garage, and well-maintained lawn at 5405 Justine Way, Winter Park, FL 32792
View Details 32 Photos
Landscaped one story house with gray siding, attached garage, and spacious yard at 5405 Justine Way, Winter Park, FL 32792
Bright living room featuring hardwood floors and neutral walls at 5405 Justine Way, Winter Park, FL 32792
Spacious living area with hardwood floors and access to kitchen and backyard at 5405 Justine Way, Winter Park, FL 32792
On Market For 33 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1247

  • Year Built

    1981

  • $/SqFt

    $345

Wrenwood Heights - Don’t just take my word for it – come see how your life fits perfectly into this Winter Park wonder. TBRO REALTY LLC.

Home For Sale $385,000

Reduced By $15,000

Mid-century modern home with gray exterior, landscaping, and driveway at 5102 Lake Howell Rd, Winter Park, FL 32792
View Details 23 Photos
Inviting front entrance with a white door, and sidelights, a welcoming poinsettia plant at 5102 Lake Howell Rd, Winter Park, FL 32792
Open living room with tile floors, partial kitchen view, and access to backyard at 5102 Lake Howell Rd, Winter Park, FL 32792
Living room with tile floors, kitchen view, and access to backyard at 5102 Lake Howell Rd, Winter Park, FL 32792
On Market For 33 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1452

  • Year Built

    1957

  • $/SqFt

    $265

Tanglewood - You will want to call this one home. COLDWELL BANKER REALTY.

Home For Sale $1,125,000

Reduced By $55,000

Two-story house with a blue metal roof, attached garage, and basketball hoop at 1975 Biscayne Dr, Winter Park, FL 32789
View Details 37 Photos
Two-story house with a blue metal roof and attached garage at 1975 Biscayne Dr, Winter Park, FL 32789
Open concept living room and kitchen with white sofas and modern decor at 1975 Biscayne Dr, Winter Park, FL 32789
Living room features a white sectional sofa, fireplace, and Christmas tree at 1975 Biscayne Dr, Winter Park, FL 32789
On Market For 34 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3270

  • Year Built

    2020

  • $/SqFt

    $344

Karolina On Killarney - Don’t miss your chance to own this property! SOGO REAL ESTATE SERVICES LLC.

Home For Sale $699,000

Charming ranch home with a two-car garage and well-manicured lawn at 1792 Killarney Dr, Winter Park, FL 32789
View Details 33 Photos
Inviting front porch with colorful seating and patterned tile at 1792 Killarney Dr, Winter Park, FL 32789
Spacious living room featuring a fireplace and mid-century modern furniture at 1792 Killarney Dr, Winter Park, FL 32789
Bright living room with a green sofa and hardwood floors at 1792 Killarney Dr, Winter Park, FL 32789
On Market For 34 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2082

  • Year Built

    1958

  • $/SqFt

    $336

Additionally, it is less than 1 mile to Trader Joe's and 1.5 miles to Park Ave. Don't miss out on this exceptional opportunity to own a piece of Winter Park paradise. THE AGENCY ORLANDO.

Pended $675,000

Reduced By $24,000

Modern home exterior boasts a white and gray color scheme, attached garage, and well-manicured lawn at 1037 Fairway Dr, Winter Park, FL 32792
View Details 47 Photos
Aerial view showcases a remodeled home with a golf course view, and a large backyard at 1037 Fairway Dr, Winter Park, FL 32792
Newly remodeled home features a clean, modern exterior and a spacious driveway at 1037 Fairway Dr, Winter Park, FL 32792
Attractive home is situated on a golf course and features a large backyard at 1037 Fairway Dr, Winter Park, FL 32792
On Market For 35 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2145

  • Year Built

    1978

  • $/SqFt

    $315

This home offers the perfect combination of style, functionality, and comfort – a true gem on Winter Golfside Community! LEGACY REALTY & BROKERS LLC.

Pended $499,900

Mid-century modern home with black and white exterior, updated landscaping, and a spacious deck at 1904 Houndslake Dr, Winter Park, FL 32792
View Details 44 Photos
Inviting kidney-shaped swimming pool with light-grey coping and a large surrounding patio at 1904 Houndslake Dr, Winter Park, FL 32792
Modern kitchen featuring white shaker cabinets, stainless steel appliances, and quartz countertops at 1904 Houndslake Dr, Winter Park, FL 32792
Modern kitchen with stainless steel appliances and white cabinets at 1904 Houndslake Dr, Winter Park, FL 32792
On Market For 32 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1840

  • Year Built

    1982

  • $/SqFt

    $272

Cedar Ridge - This home is ideally situated nearby by shopping, dining, and highways. Welcome Home! URBANISTA BROKERS.

Pended $2,495,000

Two-story white farmhouse with black roof, two-car garage, and landscaped yard at 1506 Chestnut Ave., Winter Park, FL 32789
View Details 61 Photos
Two-story white farmhouse with black roof, two-car garage, and landscaped yard at 1506 Chestnut Ave., Winter Park, FL 32789
Inviting front porch with seating area, and lush green landscaping at 1506 Chestnut Ave., Winter Park, FL 32789
Open-concept living space with L-shaped sectional sofa, fireplace, and kitchen views at 1506 Chestnut Ave., Winter Park, FL 32789
On Market For 35 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3545

  • Year Built

    2021

  • $/SqFt

    $704

Lake Knowles Terrace - This home is a masterpiece, combining modern sophistication with comfort and practicality. PREMIER SOTHEBY'S INTL. REALTY.

Pended $990,000

Aerial view of a beautiful house with a three-car garage and a well-manicured lawn at 1484 Via Sangro Pl, Winter Park, FL 32792
View Details 55 Photos
Exterior of a stunning house with a three-car garage and attractive landscaping at 1484 Via Sangro Pl, Winter Park, FL 32792
Elegant entryway with a rich wood door and tile flooring at 1484 Via Sangro Pl, Winter Park, FL 32792
Bright home office featuring a modern desk and large window at 1484 Via Sangro Pl, Winter Park, FL 32792
On Market For 32 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3063

  • Year Built

    2015

  • $/SqFt

    $323

Don't miss this opportunity to own your dream home in one of the most sought-after neighborhoods. Schedule your private tour today! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $930,000

Reduced By $9,900

Two-story house with a two-car garage and paved driveway at 675 Overspin Dr, Winter Park, FL 32789
View Details 37 Photos
Two-story house with a two-car garage and paved driveway at 675 Overspin Dr, Winter Park, FL 32789
Front entrance with arched entryway and walkway at 675 Overspin Dr, Winter Park, FL 32789
Spacious kitchen with island, stainless steel appliances, and wood cabinets at 675 Overspin Dr, Winter Park, FL 32789
On Market For 36 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2962

  • Year Built

    2010

  • $/SqFt

    $314

Dubsdread Heights - For golf enthusiasts, the prestigious Dubsdread golf course is located within a mile. COLDWELL BANKER RESIDENTIAL RE.

Pended $618,000

Charming ranch home with red door, brick facade, and spacious lawn at 2127 Lake Dr, Winter Park, FL 32789
View Details 34 Photos
House nestled in a quiet neighborhood near a lake at 2127 Lake Dr, Winter Park, FL 32789
Bright living room with hardwood floors and comfy couches at 2127 Lake Dr, Winter Park, FL 32789
Living room featuring hardwood floors and a large window at 2127 Lake Dr, Winter Park, FL 32789
On Market For 35 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1732

  • Year Built

    1955

  • $/SqFt

    $357

This home is truly a rare find in a quiet, sought-after neighborhood, NO HOA. Schedule your showing today! FANNIE HILLMAN & ASSOCIATES.

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