310 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

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 Today
  • 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 4 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 most 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 4 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 4 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
Open-concept living space with hardwood floors, arched windows, a chaise lounge, and dining area 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 5 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 $750,000

Charming home featuring a stone accent garage, well maintained lawn, and mature trees at 1139 Fairway Dr, Winter Park, FL 32792
Inviting walkway to the front door surrounded by lush greenery and foliage at 1139 Fairway Dr, Winter Park, FL 32792
Bright hallway with natural light from the atrium and neutral decor at 1139 Fairway Dr, Winter Park, FL 32792
On Market For 4 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2385

  • Year Built

    1979

  • $/SqFt

    $314

Golfside - It’s a lifestyle. Come experience it for yourself! KELLER WILLIAMS WINTER PARK.

Home For Sale $415,000

Beautiful home exterior with a brick facade, mature trees, and a well-maintained front yard creating a serene setting at 2024 Linden Road, Winter Park, FL 32792
Attractive brick home with manicured lawn, complemented by a brick driveway and mature trees, creating a welcoming ambiance at 2024 Linden Road, Winter Park, FL 32792
Close-up showcasing the charming brick facade and front door with brick paver walkway and landscaped accents at 2024 Linden Road, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 4 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1872

  • Year Built

    1972

  • $/SqFt

    $222

For those with a vision, this is your chance to transform this property into your own! PREMIER SOTHEBY'S INTL. REALTY.

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 5 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.

Home For Sale $699,900

Inviting entrance with meticulously maintained landscaping, creating a warm, secure entry at 2817 Prince John Rd, Winter Park, FL 32792
Bright kitchen featuring white cabinets, stainless steel appliances, and central island at 2817 Prince John Rd, Winter Park, FL 32792
Open-concept living area featuring a modern kitchen, dining area, and wood-look tile flooring at 2817 Prince John Rd, Winter Park, FL 32792
On Market For 5 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2183

  • Year Built

    1963

  • $/SqFt

    $321

Come visit this amazing, warm and friendly Winter Park neighborhood because you are sure to want to stay forever! LORI GILMORE REAL ESTATE LLC.

Home For Sale $525,000

This property features a brick facade, a two-car garage and beautifully maintained landscaping and driveway at 3306 Fishermans Cv, Winter Park, FL 32792
A charming single-story brick home boasts a well-kept lawn, manicured landscaping, and a welcoming entrance at 3306 Fishermans Cv, Winter Park, FL 32792
Well-maintained front yard featuring lush green grass, trimmed bushes, and a brick mailbox at 3306 Fishermans Cv, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2408

  • Year Built

    1985

  • $/SqFt

    $218

You will think the same as you take a tour. WEICHERT REALTORS HALLMARK PROPERTIES.

Home For Sale $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 5 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.

Pended $685,000

Home exterior with a large driveway, a well-maintained lawn, and a charming single-story facade at 1726 Sarong Pl, Winter Park, FL 32792
Inviting screened-in pool area with comfortable lounge chairs, offering a private outdoor retreat at 1726 Sarong Pl, Winter Park, FL 32792
Inviting pool area surrounded by a screened enclosure and complemented by comfortable lounge chairs at 1726 Sarong Pl, Winter Park, FL 32792
On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2636

  • Year Built

    2005

  • $/SqFt

    $260

Don’t miss the opportunity to show this stunning property to your most discerning buyer! KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $569,999

Front view of a traditional home with a wide driveway and a two-car garage at 7730 Broken Arrow Trl, Winter Park, FL 32792
Well-maintained single-story home with a two-car garage and landscaped front yard at 7730 Broken Arrow Trl, Winter Park, FL 32792
Charming single-story home featuring a well-maintained lawn and front landscaping at 7730 Broken Arrow Trl, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 6 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2706

  • Year Built

    1971

  • $/SqFt

    $211

Arrowhead Cove - Don’t miss your chance to enjoy the comfort and tranquility of this unique property. LA ROSA REALTY PREMIER LLC.

Home For Sale $550,000

Inviting two-story home with a beautiful lawn, showcasing the front facade at 2227 Coventry Dr, Winter Park, FL 32792
Charming two-story home with a lush lawn, complemented by mature landscaping at 2227 Coventry Dr, Winter Park, FL 32792
Beautiful two-story home featuring a well-kept lawn and neat landscaping at 2227 Coventry Dr, Winter Park, FL 32792
On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2076

  • Year Built

    1970

  • $/SqFt

    $265

Don’t miss the opportunity to own this exceptional property! LPT REALTY, LLC.

Home For Sale $539,000

Beautiful home showcasing a lush green lawn, mature trees, and a concrete driveway leading to a two-car garage at 1157 Valley Creek Run, Winter Park, FL 32792
Close-up of the home's manicured landscaping, garden beds, and inviting front entrance with lots of natural light at 1157 Valley Creek Run, Winter Park, FL 32792
Aerial view of a charming home featuring mature trees, lush lawn, and a well-maintained exterior in a serene neighborhood at 1157 Valley Creek Run, Winter Park, FL 32792
On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2171

  • Year Built

    1995

  • $/SqFt

    $248

Lost Creek - APPRASIAL has been done, and the home is ready for a new owner! CHARLES RUTENBERG REALTY ORLANDO.

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 6 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 7 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 7 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 7 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 7 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 $439,999

Beautiful single-story home featuring a freshly painted exterior, a well-kept lawn, and an attached garage at 2259 King Johns Ct, Winter Park, FL 32792
Close-up view of the home's lovely blue front door adorned with a wreath and stylish exterior lighting at 2259 King Johns Ct, Winter Park, FL 32792
Inviting living room with a comfortable sectional sofa, a modern coffee table, and a stylish entertainment center at 2259 King Johns Ct, Winter Park, FL 32792
On Market For 7 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1551

  • Year Built

    1969

  • $/SqFt

    $284

Winter Woods - This is a rare opportunity to own a move-in-ready home in one of Central Florida’s most sought-after neighborhoods. Schedule your showing today! ARK REALTY LLC.

Home For Sale $420,000

Backyard featuring a well maintained lawn, patio space and white siding at 3063 Ash Park Loop, Winter Park, FL 32792
Beautiful home with brick accents, a well-manicured lawn, and a black two-car garage at 3063 Ash Park Loop, Winter Park, FL 32792
Backyard featuring a well maintained lawn, patio space and white siding at 3063 Ash Park Loop, Winter Park, FL 32792
On Market For 7 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1673

  • Year Built

    1987

  • $/SqFt

    $251

The combination of modern updates, functional spaces, and neighborhood amenities, makes this home an attractive option for anyone seeking a comfortable and convenient lifestyle. ANDERSON INVESTMENT PROPERTIES.

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 7 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 $1,150,000

Modern kitchen with white cabinetry, stainless steel appliances, and wood-look flooring at 2011 Soaring Oak Way, Winter Park, FL 32792
Close-up of modern kitchen featuring gray backsplash, stainless steel range hood and appliances at 2011 Soaring Oak Way, Winter Park, FL 32792
Stainless steel kitchen appliances with view of dining area featuring window views at 2011 Soaring Oak Way, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 8 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4307

  • Year Built

    2021

  • $/SqFt

    $267

Waters Edge At Hawks Crest - Don't miss your opportunity to live in one of the newest and most desirable communities in Winter Park. Schedule your showing today! DEGREE REALTY LLC.

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 8 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.

Pended $650,000

Home exterior featuring an attached two car garage and manicured lawn at 2855 Lion Heart Rd, Winter Park, FL 32792
View of entryway with pendant lighting and decorative console table at 2855 Lion Heart Rd, Winter Park, FL 32792
Open floor plan with living room flowing into dining area and kitchen at 2855 Lion Heart Rd, Winter Park, FL 32792
On Market For 9 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1727

  • Year Built

    1963

  • $/SqFt

    $376

Located on a quiet, tree-lined street with sidewalks for walking or biking, zoned for highly rated Winter Park schools, and with an optional HOA, this property is a perfect choice for families, professionals, or investors alike. MY REALTY GROUP, LLC..

Pended $384,900

Inviting single-story home featuring a lush green lawn, mature trees, and a well-maintained exterior at 7543 Dockside St, Winter Park, FL 32792
Bird's eye view of home featuring mature landscaping, green lawn, a driveway and a neutral color scheme at 7543 Dockside St, Winter Park, FL 32792
Aerial view of backyard featuring mature landscaping, fenced in yard and a concrete patio at 7543 Dockside St, Winter Park, FL 32792
On Market For 9 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1434

  • Year Built

    1973

  • $/SqFt

    $268

Woodcrest - Past the porch you have a sizable back yard for gardening and or entertaining. Bring your offers! ! LPT REALTY, LLC.

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 12 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.

Pended $625,000

Inviting backyard pool featuring ample patio space, landscaping, and a storage shed at 2707 Prince John Rd, Winter Park, FL 32792
Open-concept kitchen with stainless steel appliances and hardwood flooring at 2707 Prince John Rd, Winter Park, FL 32792
Modern kitchen featuring white cabinets, stainless steel appliances, and a kitchen island at 2707 Prince John Rd, Winter Park, FL 32792
On Market For 11 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1670

  • Year Built

    1962

  • $/SqFt

    $374

Roof - 2022 Hvac - 2022 Plumbing - 2016 Water Heater - 2023 KELLER WILLIAMS WINTER PARK.

Home For Sale $579,900

Detailed floorplan layout of the house showing room dimensions and layout at 7584 Lodge Pole Trl, Winter Park, FL 32792
Covered front entry with decorative sidelights and a concrete path at 7584 Lodge Pole Trl, Winter Park, FL 32792
Inviting foyer with decorative glass sidelights and attractive wood-look flooring at 7584 Lodge Pole Trl, Winter Park, FL 32792
On Market For 11 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1906

  • Year Built

    1972

  • $/SqFt

    $304

Arrowhead Cove - Ready for a new owner. Let's make a deal. SAND DOLLAR REALTY GROUP INC.

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 11 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 12 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 12 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 11 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 $565,500

Reduced By $14,000

Charming single-story home with well-manicured lawn and inviting curb appeal at 3131 Lowndes Dr, Winter Park, FL 32792
Bright living room with ceiling fan, stylish decor, and lots of natural light at 3131 Lowndes Dr, Winter Park, FL 32792
Modern eat-in kitchen with white cabinets, stainless steel appliances, and updated countertops at 3131 Lowndes Dr, Winter Park, FL 32792
On Market For 12 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2126

  • Year Built

    1967

  • $/SqFt

    $266

Georgetown Estates - Schedule your private tour today and step into the home that defines Winter Park living! A +ROI PROPERTY.

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 11 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 13 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 13 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 $479,900

A lovely two-story home with a well-maintained lawn and attached two-car garage at 1532 Lawndale Cir, Winter Park, FL 32792
Inviting front entrance with a white door, sidelight window, and decorative potted plant at 1532 Lawndale Cir, Winter Park, FL 32792
Open-concept living space with tile flooring, soaring ceilings, and natural light at 1532 Lawndale Cir, Winter Park, FL 32792
On Market For 13 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2035

  • Year Built

    1986

  • $/SqFt

    $236

Country Lane - Don’t miss your chance to own a piece of paradise—schedule your private tour today! KELLER WILLIAMS WINTER PARK.

Home For Sale $419,000

Spacious driveway leading to a blue garage door, set against a well-kept lawn at 1566 Lawndale Cir, Winter Park, FL 32792
Bright, open living area featuring vaulted ceilings and modern wood-look flooring at 1566 Lawndale Cir, Winter Park, FL 32792
Vaulted ceilings and fan highlight this open living space with modern vinyl plank flooring at 1566 Lawndale Cir, Winter Park, FL 32792
On Market For 13 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1592

  • Year Built

    1985

  • $/SqFt

    $263

Experience the best of Winter Park living—text your real estate agent today for more information or to schedule a viewing! OPTIMA ONE REALTY, INC..

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 14 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 $914,000

Aerial view of a well-maintained home with a pristine yard, nearby pond, and three-car garage at 2012 Soaring Oak Way, Winter Park, FL 32792
Beautiful single-story home featuring a three-car garage and a tile roof at 2012 Soaring Oak Way, Winter Park, FL 32792
Charming entryway with stone accents and a cozy seating area at 2012 Soaring Oak Way, Winter Park, FL 32792
On Market For 12 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3050

  • Year Built

    2021

  • $/SqFt

    $300

Waters Edge At Hawks Crest - VIEW WALK THROUGH VIDEO - at Virtual tour link KELLER WILLIAMS REALTY AT THE PARKS.

Pended $799,999

On Market For 10 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 $1,360,000

Stunning two-story white home with a three-car garage, brick driveway, and manicured lawn with curb appeal at 1269 Wading Waters Cir, Winter Park, FL 32792
Beautiful aerial view of several homes with lush green trees and a scenic lake backdrop at 1269 Wading Waters Cir, Winter Park, FL 32792
Aerial shot of a private home with pool and patio, lush yard, and neighborhood street at 1269 Wading Waters Cir, Winter Park, FL 32792
On Market For 15 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    4468

  • Year Built

    2021

  • $/SqFt

    $304

Waters Edge At Hawks Crest - Put in your paddle board, kayak or just enjoy the wonderful sunsets from the fishing dock. HAMILTON REALTY.

Home For Sale $478,000

Close-up of the front entrance with a gray walkway, colorful flowers, and a bright turquoise door at 7320 Fieldcrest Ave, Winter Park, FL 32792
Front exterior view of a white home with stone accents, manicured landscaping, and palm trees at 7320 Fieldcrest Ave, Winter Park, FL 32792
Close up of the front of the house, featuring a bright turquoise door and meticulously maintained landscaping at 7320 Fieldcrest Ave, Winter Park, FL 32792
On Market For 15 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1919

  • Year Built

    1970

  • $/SqFt

    $249

Woodcrest - The property is situated in a cul-de-sac with no through traffic, no HOA with easy access to Full Sail, UCF, Winter Park shopping, restaurants, Downtown Orland, International Airport. COLDWELL BANKER REALTY.

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 17 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 18 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.

Pended $950,000

Beautiful home showcasing the manicured lawn, trimmed bushes, and two-car garage, all under a bright blue sky at 901 Golfside Dr, Winter Park, FL 32792
Corner lot featuring a charming brick house with a well-manicured lawn, pathway, and two-car garage at 901 Golfside Dr, Winter Park, FL 32792
Spacious living room featuring hardwood floors, a leather sofa, a dining area, and lots of natural light at 901 Golfside Dr, Winter Park, FL 32792
On Market For 14 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2392

  • Year Built

    1969

  • $/SqFt

    $397

Golfside - Don't miss out on this perfect home for creating memories for years to come! COLDWELL BANKER RESIDENTIAL RE.

Pended $799,000

Inviting foyer featuring neutral paint, paneled walls, a console table with decorative accents, and a tiled floor at 2255 Marsh Sedge Ln, Winter Park, FL 32792
Cozy living room featuring large windows, a comfortable seating arrangement, and a stylish area rug at 2255 Marsh Sedge Ln, Winter Park, FL 32792
Elegant living room featuring recessed lighting, neutral paint, comfortable seating, and a stylish area rug at 2255 Marsh Sedge Ln, Winter Park, FL 32792
On Market For 17 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2192

  • Year Built

    2020

  • $/SqFt

    $365

Preserve At Hawks Crest - Click the link for the virtual 3-D tour! KELLER WILLIAMS ADVANTAGE 2 REALTY.

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 18 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.

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 407-967-1435 and speak with one of our real estate consultants.

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