335 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $4,750,000

Beautiful white stucco house with two-car garage, perfectly manicured lawn, and mature trees at 1150 Via Salerno, Winter Park, FL 32789
Striking contemporary home with a white exterior, multi-level roofline, and professionally landscaped front yard at 1150 Via Salerno, Winter Park, FL 32789
Charming home entrance with unique wood door, complemented by manicured greenery, offering an inviting curb appeal at 1150 Via Salerno, Winter Park, FL 32789
On Market For 2 Days
  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    3850

  • Year Built

    2025

  • $/SqFt

    $1,234

Cloister Grove - Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle tucked within one of Winter Park’s most exclusive enclaves. KELLY PRICE & COMPANY LLC.

Home For Sale $3,975,000

Modern home with a unique facade and multi-paned glass garage door, complemented by decorative driveway at 1742 Temple Dr, Winter Park, FL 32789
Contemporary home featuring distinctive wood siding and artistic driveway, enhanced by lush greenery at 1742 Temple Dr, Winter Park, FL 32789
Charming curb appeal of a modern home featuring unique design elements and professional landscaping at 1742 Temple Dr, Winter Park, FL 32789
On Market For 3 Days
  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    3658

  • Year Built

    2003

  • $/SqFt

    $1,087

Lake Knowles Terrace - Contact us today to schedule your private showing. PREMIER SOTHEBY'S INTL. REALTY.

Pended $3,250,000

Well-maintained home with manicured lawn, mature trees, and a brick facade at 641 Virginia Dr, Winter Park, FL 32789
Charming single-story home with lush landscaping, mature trees, and a two-car garage at 641 Virginia Dr, Winter Park, FL 32789
Home exterior featuring a well-manicured lawn, mature trees, and a two-car garage at 641 Virginia Dr, Winter Park, FL 32789
On Market For 4 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3223

  • Year Built

    1966

  • $/SqFt

    $1,008

Whether you're seeking a peaceful lakefront retreat, a renovation opportunity with character, or the perfect site to build your dream home, 641 Virginia Drive offers a once-in-a-generation opportunity in one of Central Florida’s most distinguished communities. KELLER WILLIAMS WINTER PARK.

Home For Sale $1,550,000

Two-story home boasts a well-manicured lawn, modern garage door, and meticulous landscaping at 1541 Chestnut Ave, Winter Park, FL 32789
Charming front entrance with a modern door, stylish lighting, and lush landscaping at 1541 Chestnut Ave, Winter Park, FL 32789
Inviting front porch with a modern door, stylish seating, and beautiful greenery at 1541 Chestnut Ave, Winter Park, FL 32789
On Market For 3 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2840

  • Year Built

    2018

  • $/SqFt

    $546

Lake Knowles Terrace - Schools are the best with Lakemont Elementary, Maitland Middle and Winter Park High Schools. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $730,000

Two-story home showcasing manicured landscaping, a two-car garage and a welcoming front entrance at 7895 Pleasant Pine Cir, Winter Park, FL 32792
Two-story home showcasing manicured landscaping, a two-car garage and a welcoming front entrance at 7895 Pleasant Pine Cir, Winter Park, FL 32792
Inviting front porch featuring a covered entrance, neutral colors, and comfortable seating at 7895 Pleasant Pine Cir, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 4 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3568

  • Year Built

    2014

  • $/SqFt

    $205

Enclave At Aloma - Schedule your private showing today to experience the beauty and elegance of this Winter Park gem before it’s gone. ALL REAL ESTATE & INVESTMENTS.

Home For Sale $354,900

Home exterior with attached garage and driveway showcasing the landscaping around the property at 2020 Cocos Ct, Winter Park, FL 32792
Backyard swimming pool bordered by tropical greenery and a concrete patio at 2020 Cocos Ct, Winter Park, FL 32792
Well-lit living room featuring hardwood floors, large windows, and access to an enclosed porch at 2020 Cocos Ct, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 4 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1715

  • Year Built

    1966

  • $/SqFt

    $207

Don’t miss the chance to unlock this home’s full potential and create something special in one of Central Florida’s most sought-after areas. Schedule your private showing today! EXP REALTY LLC.

Home For Sale $1,300,000

Charming two-story home featuring lush landscaping, a tiled roof, and a paved driveway at 800 Hamilton Place Ct, Winter Park, FL 32789
Elegant front porch with stone accents, decorative lion statues, and stylish lighting fixtures at 800 Hamilton Place Ct, Winter Park, FL 32789
Elegant foyer featuring a decorative glass front door, a large mirror, and a potted plant at 800 Hamilton Place Ct, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3363

  • Year Built

    2015

  • $/SqFt

    $387

Hamilton Place - This move-in ready home blends luxury and location in one of Central Florida’s most coveted neighborhoods. EPIC REAL ESTATE ADVISORS LLC.

Home For Sale $1,225,000

Attractive single-story house with a landscaped front yard, decorative shrubbery, and a concrete walkway at 2890 Wild Ginger Ct, Winter Park, FL 32792
Beautiful home exterior featuring manicured lawn, mature trees, and a sidewalk leading to the front entrance at 2890 Wild Ginger Ct, Winter Park, FL 32792
Stylish single-story house featuring a lush lawn, mature landscaping, and an attached two-car garage at 2890 Wild Ginger Ct, Winter Park, FL 32792
On Market For 5 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3408

  • Year Built

    1993

  • $/SqFt

    $359

An incredible opportunity in Winter Park. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $799,900

Back exterior view of gray single-story home with a fenced in yard and AC Unit at 311 Cortland Ave, Winter Park, FL 32789
Entrance showing tile floors, ceiling fan and front door at 311 Cortland Ave, Winter Park, FL 32789
Bright living room with white walls, tile floors, ceiling fan, and natural light at 311 Cortland Ave, Winter Park, FL 32789
On Market For 5 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1382

  • Year Built

    1952

  • $/SqFt

    $579

With vintage character, and incredible location with lake access at the end of the street, this Winter Park gem is not to be missed! KELLER WILLIAMS WINTER PARK.

Home For Sale $639,900

Private backyard featuring a sparkling pool, patio seating, and lush green lawn perfect for entertaining at 402 Saint Dunstan Way, Winter Park, FL 32792
Open-concept living room featuring tile floors, comfortable seating, and view into the kitchen and dining areas at 402 Saint Dunstan Way, Winter Park, FL 32792
Modern kitchen with stainless steel appliances, white quartz countertops, and a stylish blue backsplash at 402 Saint Dunstan Way, Winter Park, FL 32792
On Market For 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1779

  • Year Built

    1964

  • $/SqFt

    $360

Metal Roof - 2017, HVAC - 2022, Plumbing - 2017, Electrical - 2018(new panel). KELLER WILLIAMS WINTER PARK.

Home For Sale $1,976,000

Bright foyer showcasing a modern blue door, sleek hardwood floors, and pristine white walls at 617 Worthington Dr, Winter Park, FL 32789
Open-concept living area with hardwood floors, modern furnishings, and views of the backyard pool at 617 Worthington Dr, Winter Park, FL 32789
Comfortable living room with blue accent wall, plush seating, and sliding glass doors to the patio at 617 Worthington Dr, Winter Park, FL 32789
On Market For 7 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3533

  • Year Built

    2018

  • $/SqFt

    $559

Kenilworth Shores - Schedule your private showing today and make this exquisite property your new home. KELLY PRICE & COMPANY LLC.

Home For Sale $6,180,000

Stately home with covered parking, lush greenery, and distinctive architecture, perfect for luxurious living at 2211 Azalea Pl, Winter Park, FL 32789
Beautiful two-story home with manicured landscaping, gated entrance, and a timeless Mediterranean design at 2211 Azalea Pl, Winter Park, FL 32789
Expansive home featuring a porte cochere, well-maintained grounds, and an inviting entrance, ideal for entertaining at 2211 Azalea Pl, Winter Park, FL 32789
On Market For 7 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    7278

  • Year Built

    2008

  • $/SqFt

    $849

Maitland Shores - This is a rare opportunity to own a one-of-a-kind estate in one of Winter Park’s most sought-after locations, where quiet sophistication meets waterfront luxury. FORTUNE INTERNATIONAL REALTY.

Home For Sale $3,895,000

Beautiful home with mature trees, lush lawn, and a long driveway leading to a charming residence at 1820 Glencoe Rd, Winter Park, FL 32789
Close-up of the attached two-car garage with blue doors and elegant brick paver driveway and manicured landscape at 1820 Glencoe Rd, Winter Park, FL 32789
Inviting foyer features a modern staircase, wood floors, and a bright, open feel at 1820 Glencoe Rd, Winter Park, FL 32789
On Market For 8 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4055

  • Year Built

    2025

  • $/SqFt

    $961

Schedule your private tour today and experience luxury living redefined. CORCORAN PREMIER REALTY.

Home For Sale $2,800,000

Tranquil backyard pool with a jacuzzi, surrounded by lush greenery and a privacy fence at 1341 Place Picardy, Winter Park, FL 32789
Bright entryway with stylish decor, light hardwood floors, and a view to the front yard at 1341 Place Picardy, Winter Park, FL 32789
Open concept living area with hardwood floors, flowing into the kitchen and dining spaces at 1341 Place Picardy, Winter Park, FL 32789
On Market For 8 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4469

  • Year Built

    2016

  • $/SqFt

    $627

Fontainebleau - Call now for your private tour! STOCKWORTH REALTY GROUP.

Home For Sale $1,799,000

Close-up of the front door highlighting its design, sidelights, and the home's address number, '1640' at 1640 Mayfield Ave, Winter Park, FL 32789
Inviting foyer with hardwood floors, elegant lighting, and decor that leads into the main living spaces at 1640 Mayfield Ave, Winter Park, FL 32789
Open-concept view of the foyer featuring hardwood floors, lighting and transition to kitchen and living spaces at 1640 Mayfield Ave, Winter Park, FL 32789
On Market For 8 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2907

  • Year Built

    1953

  • $/SqFt

    $619

Park Avenue and Downtown Winter Park with plenty of fine dining and upscale shopping options are a bike ride away or short drive ! RE/MAX PRIME PROPERTIES.

Home For Sale $985,000

An aerial view of the property showing its location, layout, pool and waterfront access at 7801 Georgeann St, Winter Park, FL 32792
Expansive outdoor patio with views of the pool, outdoor kitchen and lake at 7801 Georgeann St, Winter Park, FL 32792
Charming two-story home featuring a well-manicured lawn and tropical landscaping at 7801 Georgeann St, Winter Park, FL 32792
On Market For 8 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    3158

  • Year Built

    1981

  • $/SqFt

    $312

A little piece of paradise that is conveniently located to shopping, restaurants and SR 417! RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $1,575,000

Charming two-story home showcasing a balcony, arched doorway, two-car garage, and well-manicured landscaping at 1473 Berkshire Ave, Winter Park, FL 32789
Beautiful two-story home with a covered porch, arched entrance, balcony, and lush, green landscaping at 1473 Berkshire Ave, Winter Park, FL 32789
Attractive two-story house displaying an arched entry, balcony, two-car garage, and neat front yard landscaping at 1473 Berkshire Ave, Winter Park, FL 32789
On Market For 9 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    2895

  • Year Built

    2025

  • $/SqFt

    $544

Orwin Manor - Schedule your private tour today — this home defines the Winter Park lifestyle. GOLDEN GROUP REALTY LLC.

Home For Sale $1,795,000

Elegant two-story home featuring a three-car garage, with modern design and a luxury sports car at 1780 Mizell Ave., Winter Park, FL 32789
Charming two-story home featuring a well-manicured lawn and black framed windows at 1780 Mizell Ave., Winter Park, FL 32789
Beautiful front entrance with craftsman style doors and manicured landscaping at 1780 Mizell Ave., Winter Park, FL 32789
On Market For 9 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2743

  • Year Built

    2025

  • $/SqFt

    $654

Schedule your private showing today, this is luxury Winter Park living redefined. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,675,000

Charming two-story home with lush landscaping and a well-manicured lawn at 1350 Lyndale Blvd, Winter Park, FL 32789
Charming two-story home with lush landscaping and a well-manicured lawn at 1350 Lyndale Blvd, Winter Park, FL 32789
Inviting living room with a cozy seating arrangement, French doors leading to the pool, and a ceiling fan at 1350 Lyndale Blvd, Winter Park, FL 32789
On Market For 11 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3478

  • Year Built

    2003

  • $/SqFt

    $482

Dixie Terrace - This truly is a beautiful home with luxurious details throughout, including French doors leading from the primary bedroom room and the family room to the screened pool, high-end flooring, elegant crown molding and millwork, a 1/2 pool bath and tray ceiling and California Closets in the owner’s suite. PALMANO GROUP RE BROKERAGE LLC.

Pended $659,900

Inviting front exterior featuring a well-maintained walkway, lush landscaping and a stylish blue front door at 1926 Natalen Rd, Winter Park, FL 32792
Charming front entrance showcasing a well-designed pathway leading to a vibrant blue front door at 1926 Natalen Rd, Winter Park, FL 32792
Bright living room with modern décor, light wood floors, and seamless transition to the outdoor space at 1926 Natalen Rd, Winter Park, FL 32792
On Market For 10 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1469

  • Year Built

    1957

  • $/SqFt

    $449

Don’t miss this opportunity to make this wonderful home your very own. Schedule your showing today. EXP REALTY LLC.

Home For Sale $575,000

Charming single-story home with a brick pathway and beautiful lawn at 212 Blossom Ln, Winter Park, FL 32789
Inviting living room featuring a comfortable sectional sofa, hardwood floors, and french doors to the backyard at 212 Blossom Ln, Winter Park, FL 32789
Dining room featuring an ornate wooden table and chairs, white shuttered windows, and views into living room at 212 Blossom Ln, Winter Park, FL 32789
On Market For 11 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1771

  • Year Built

    1954

  • $/SqFt

    $325

This seller is motivated so bring your offers! BHHS FLORIDA REALTY.

Home For Sale $459,900

Inviting single-story home with an attached two-car garage and mature landscaping at 2151 Conifer Ave, Winter Park, FL 32792
Private backyard featuring a refreshing in-ground pool and brick-paved patio area at 2151 Conifer Ave, Winter Park, FL 32792
Welcoming foyer showcasing the front door and staircase with iron banister at 2151 Conifer Ave, Winter Park, FL 32792
On Market For 10 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1806

  • Year Built

    1970

  • $/SqFt

    $255

Excellent A-Rated Seminole County Schools. Location, Location, Location. Welcome Home!! ! KORR REALTY CORP.

Pended $439,900

Spacious home with lush backyard, featuring a charming gazebo, mature trees, and a peaceful setting at 1945 Bering Ave, Winter Park, FL 32789
Bright living room with hardwood floors, stylish furniture, modern fan, and an open view of the kitchen at 1945 Bering Ave, Winter Park, FL 32789
Cozy living room with large window, comfortable seating, hardwood floors, and stylish decor at 1945 Bering Ave, Winter Park, FL 32789
On Market For 11 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1576

  • Year Built

    1958

  • $/SqFt

    $279

As for the Theme Parks, you are 35 minutes away from Disney World, Epic Universe/Universal, and less than an hour away from the nearest beach. Welcome home! HORIZON WEST REALTY.

Home For Sale $379,900

Spacious living room featuring high ceilings, lots of natural light, and a staircase at 3352 Hamlet Loop, Winter Park, FL 32792
Spacious living room featuring high ceilings, lots of natural light, and a staircase at 3352 Hamlet Loop, Winter Park, FL 32792
Bright living room featuring high ceilings, lots of natural light, and a decorative chandelier at 3352 Hamlet Loop, Winter Park, FL 32792
On Market For 11 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1397

  • Year Built

    1993

  • $/SqFt

    $272

Villas Of Casselberry - **Seller may offer to buy down the buyer's mortgage interest rate with an acceptable offer. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $1,925,000

Inviting front porch with rocking chairs and a wood door with sidelights at 1355 Hibiscus Ave, Winter Park, FL 32789
Elegant foyer with hardwood floors, a decorative rug, and a wood front door with sidelights at 1355 Hibiscus Ave, Winter Park, FL 32789
Formal dining room with hardwood floors, a chandelier, and a wooden table with chairs at 1355 Hibiscus Ave, Winter Park, FL 32789
On Market For 11 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4155

  • Year Built

    2006

  • $/SqFt

    $463

Lake Knowles Terrace - With a new roof (2023), commercial grade water heater (2022), fresh exterior paint (2024) and many upgrades, this home offers turnkey living in one of Winter Park’s finest communities. PALMANO GROUP RE BROKERAGE LLC.

Home For Sale $1,825,000

Beautiful single-story home with a lush green lawn, mature trees, and nice curb appeal at 446 Alberta Dr, Winter Park, FL 32789
Breathtaking aerial view of a home on the water with surrounding trees at sunset at 446 Alberta Dr, Winter Park, FL 32789
Gorgeous aerial view of a lakeside home surrounded by lush greenery and beautiful waterfront scenery at 446 Alberta Dr, Winter Park, FL 32789
On Market For 12 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    3263

  • Year Built

    1968

  • $/SqFt

    $559

Whether you're looking to renovate, invest, expand upward, or build your dream home — the potential here is truly exceptional. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $549,000

Beautiful kitchen with granite countertops, stainless steel appliances, and stylish gray cabinets at 2244 Brookshire Ave, Winter Park, FL 32792
Bright kitchen featuring stainless steel appliances, granite countertops, and updated cabinetry at 2244 Brookshire Ave, Winter Park, FL 32792
Open kitchen layout with granite countertops, wood floors and a view into the living area at 2244 Brookshire Ave, Winter Park, FL 32792
On Market For 11 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1464

  • Year Built

    1958

  • $/SqFt

    $375

More recent improvements include overhead garage storage (2024), new exterior doors leading to the backyard and garage (2024), and brand-new ceiling fans in all bedrooms (2025). EXP REALTY LLC.

Pended $389,000

Open-concept kitchen and living area with hardwood floors, pendant lighting, and stainless steel appliances at 7331 Blue Jacket W Pl, Winter Park, FL 32792
Living area featuring hardwood floors, modern lighting, and a view of the front entrance at 7331 Blue Jacket W Pl, Winter Park, FL 32792
Modern kitchen with stainless steel appliances, stone countertops, and backsplash at 7331 Blue Jacket W Pl, Winter Park, FL 32792
On Market For 12 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1581

  • Year Built

    1970

  • $/SqFt

    $246

Woodcrest - Don’t miss this move-in-ready gem with modern upgrades and an unbeatable location—schedule your showing today! NETWORTH REALTY OF ORLANDO, LLC.

Home For Sale $515,000

Classic dining room featuring hardwood floors, tan walls, and decorative vintage accents at 1924 Summerfield Rd, Winter Park, FL 32792
Inviting living room with a cozy seating arrangement and classic design elements at 1924 Summerfield Rd, Winter Park, FL 32792
This main bedroom has an en suite bath, and a mirrored closet with room for a work out area at 1924 Summerfield Rd, Winter Park, FL 32792
On Market For 13 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1492

  • Year Built

    1956

  • $/SqFt

    $345

Kenilworth Shores - Come see for yourself and imagine the next chapter of your story here. KELLER WILLIAMS REALTY AT THE PARKS.

Pended $430,000

Beautifully landscaped single-story home with lush green lawn and lovely curb appeal at 5210 Poinsetta Ave, Winter Park, FL 32792
Attractive single-story home with large driveway, lush lawn, and charming curb appeal at 5210 Poinsetta Ave, Winter Park, FL 32792
Modern kitchen with stainless steel appliances, sleek cabinetry, and stylish black hardware at 5210 Poinsetta Ave, Winter Park, FL 32792
On Market For 12 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1476

  • Year Built

    1974

  • $/SqFt

    $291

Wrenwood Heights - Discover your perfect Florida haven today! CHARLES RUTENBERG REALTY ORLANDO.

Pended $700,000

Inviting home showcasing a well-maintained lawn and an appealing facade with cozy front porch seating at 2190 Temple Dr, Winter Park, FL 32789
Property featuring a paved driveway, green lawn, and privacy fence, perfect for outdoor enjoyment at 2190 Temple Dr, Winter Park, FL 32789
Cozy living room featuring hardwood floors, a ceiling fan, and a comfortable seating area at 2190 Temple Dr, Winter Park, FL 32789
On Market For 14 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1442

  • Year Built

    1956

  • $/SqFt

    $485

Fontainebleau - A simply stunning home built with the most exquisite luxuries. MAINFRAME REAL ESTATE.

Home For Sale $699,000

Attractive home exterior featuring an attached garage, arched windows, and lush landscaping in a green neighborhood at 1891 Bryan Ave, Winter Park, FL 32789
Bright living room with a fireplace, modern furnishings, neutral color palette, and wood-look tile floors at 1891 Bryan Ave, Winter Park, FL 32789
Inviting living room with neutral finishes, wood-look tile floors, modern furniture, and an open floor plan at 1891 Bryan Ave, Winter Park, FL 32789
On Market For 13 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1622

  • Year Built

    1989

  • $/SqFt

    $431

Located just minutes from top-rated Winter Park schools, shopping, and dining. Don’t miss this opportunity! CORCORAN PREMIER REALTY.

Home For Sale $390,000

Front yard view of a cozy home with a lush green lawn and a modern facade at 3430 Arbutus Ln, Winter Park, FL 32792
Covered front porch with gray flooring, offering a welcoming entrance to the home at 3430 Arbutus Ln, Winter Park, FL 32792
Bright living room featuring neutral furniture, a ceiling fan, and sliding glass doors to the pool at 3430 Arbutus Ln, Winter Park, FL 32792
On Market For 14 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1674

  • Year Built

    1960

  • $/SqFt

    $233

Eastbrook - Whether you’re looking for a multigenerational setup or a smart investment opportunity, this home has it all. Schedule your private showing today! URBAN NEST CLUB INC.

Home For Sale $889,000

Beautifully landscaped front yard leading to a gray craftsman style home at 1217 Kenwood Ave, Winter Park, FL 32789
Open-concept living room with hardwood floors, modern furnishings, and plenty of natural light at 1217 Kenwood Ave, Winter Park, FL 32789
Bright living room with large windows, sleek furniture, and neutral decor at 1217 Kenwood Ave, Winter Park, FL 32789
On Market For 15 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1240

  • Year Built

    1955

  • $/SqFt

    $717

Dixie Terrace - Don’t miss this rare opportunity in one of Winter Park’s most walkable locations! LEHMANN REALTY INC..

Pended $810,000

Inviting single-story home featuring a well-manicured front yard with mature trees at 1261 Burning Tree Ln, Winter Park, FL 32792
Beautiful kitchen featuring dark countertops, an island, and pendant lighting at 1261 Burning Tree Ln, Winter Park, FL 32792
Well-lit kitchen with white cabinets, dark countertops, and modern appliances at 1261 Burning Tree Ln, Winter Park, FL 32792
On Market For 15 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2223

  • Year Built

    1979

  • $/SqFt

    $364

Greenview Winter Pines - Don’t miss your chance to own a piece of Winter Park paradise. Schedule your private tour today! KELLER WILLIAMS RLTY FL. PARTN.

Home For Sale $1,200,000

Detailed first floor plan showcases open-concept living, kitchen, dining, and garage layout at 1807 Magnolia Ave, Winter Park, FL 32789
Second floor plan features bedrooms, bathrooms, and laundry room layout at 1807 Magnolia Ave, Winter Park, FL 32789
On Market For 16 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2618

  • Year Built

    2026

  • $/SqFt

    $458

Temple Terrace - While the listing does not currently include a pool, the builder's preferred lender can seamlessly integrate a pool into your financing if desired, allowing for a one-time closing and a quick pool installation post-closing. LOMBARDO TEAM REAL ESTATE LLC.

Pended $415,000

Single-story home with lush green lawn and mature trees, offering shade and curb appeal at 5334 Cypress Dr, Winter Park, FL 32792
Home exterior with spacious driveway and green garage door, showcasing a well-maintained property at 5334 Cypress Dr, Winter Park, FL 32792
Inviting front entrance featuring a charming green double door with glass panels and a sidelight window at 5334 Cypress Dr, Winter Park, FL 32792
On Market For 16 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1734

  • Year Built

    1976

  • $/SqFt

    $239

Wrenwood Heights - Don’t miss this opportunity—schedule your private tour today! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $299,900

Spacious living room featuring hardwood floors and ample natural light at 5588 Garden Grove Cir, Winter Park, FL 32792
Functional kitchen with laminate countertops and white appliances at 5588 Garden Grove Cir, Winter Park, FL 32792
Clean bedroom with neutral carpet, a ceiling fan, and a window for natural light at 5588 Garden Grove Cir, Winter Park, FL 32792
*IS BANK OWNED
On Market For 17 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1310

  • Year Built

    1986

  • $/SqFt

    $229

Garden Grove - This home is situated in a highly desirable area with access to top-rated schools, medical facilities, shopping, dining, and convenient transportation options. FLORIDA REAL ESTATE PROPERTIES LLC.

Pended $779,000

Charming front entryway with a modern door, stone accents, and an ADT security system at 2247 Marsh Sedge Ln, Winter Park, FL 32792
Inviting hallway with wood floors and a view leading into the living room and bathroom at 2247 Marsh Sedge Ln, Winter Park, FL 32792
Entryway featuring stylish wood floors, a white door, and an inviting view into a bedroom at 2247 Marsh Sedge Ln, Winter Park, FL 32792
On Market For 18 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2192

  • Year Built

    2020

  • $/SqFt

    $355

Preserve At Hawks Crest - At the front of the neighborhood shops and dining includes Kelly's Ice Cream, Foxtail Coffee, Sobol, Winter Park Pediatric Dentistry and Park Maitland's Preschool Campus. LPT REALTY, LLC.

Home For Sale $499,999

Reduced By $18,001

Inviting covered entry featuring double doors, textured walls, tiled floors, and natural light at 1921 Heathwood Dr, Winter Park, FL 32792
Bright entryway featuring double doors, hardwood flooring, and modern decor at 1921 Heathwood Dr, Winter Park, FL 32792
Cozy living room featuring neutral decor, plush seating, and abundant natural light at 1921 Heathwood Dr, Winter Park, FL 32792
On Market For 19 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1611

  • Year Built

    1980

  • $/SqFt

    $310

Cedar Ridge - Don’t miss your chance to own this exceptional home! NEXTDWELL.

Home For Sale $499,900

Beautifully landscaped front yard with a mature tree, green lawn, and a charming home exterior at 1173 Valley Creek Run, Winter Park, FL 32792
Well-maintained home with a manicured lawn, mature landscaping, and a two-car garage at 1173 Valley Creek Run, Winter Park, FL 32792
Spacious living room with tile flooring and a sliding glass door leading to the outdoor patio at 1173 Valley Creek Run, Winter Park, FL 32792
On Market For 19 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1906

  • Year Built

    1995

  • $/SqFt

    $262

Don’t miss the opportunity to make this your next home! LUKER & CO REAL ESTATE LLC.

Home For Sale $440,000

Aerial view of the property showcasing the pool, yard, and neighborhood at 4959 Ardmore Dr, Winter Park, FL 32792
Comfortable living room with a blue sofa, desk, and modern decor at 4959 Ardmore Dr, Winter Park, FL 32792
View from living area into the kitchen and a play area, creating an open atmosphere at 4959 Ardmore Dr, Winter Park, FL 32792
On Market For 18 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1664

  • Year Built

    1979

  • $/SqFt

    $264

Wrenwood Heights - With its large lot, peaceful location, and tasteful improvements, this property is a rare find in Winter Park. COMPASS FLORIDA LLC.

Home For Sale $3,599,999

Beautifully landscaped side view of a modern home featuring a three-car garage and well-manicured lawn at 1761 Legion Dr, Winter Park, FL 32789
This bathroom features marble walls and floors, a spacious walk-in shower, and dual vanities with modern fixtures at 1761 Legion Dr, Winter Park, FL 32789
A luxurious bathroom boasts marble walls and floors, mirrored wall, dual sinks and modern lighting at 1761 Legion Dr, Winter Park, FL 32789
On Market For 19 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4955

  • Year Built

    2017

  • $/SqFt

    $727

Green Oaks - All just moments from the shops, dining, and charm of downtown Winter Park. SCANLON REALTY GROUP LLC.

Home For Sale $2,700,000

Open concept living room featuring a large sectional sofa, modern furniture, and access to the backyard at 1781 Pine Ave, Winter Park, FL 32789
Modern kitchen with white cabinets, a center island with seating, and stainless steel appliances at 1781 Pine Ave, Winter Park, FL 32789
Backyard pool and outdoor living area featuring a covered patio and an outdoor kitchen at 1781 Pine Ave, Winter Park, FL 32789
On Market For 19 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3882

  • Year Built

    2017

  • $/SqFt

    $696

From the moment you step inside, you’ll fall in love with its elegance and charm. FLORIDA CONNEXION PROPERTIES.

Home For Sale $1,595,000

Modern two-story home with a well-manicured lawn, minimalist landscaping, and contrasting dark trim at 1733 Harmon Ave, Winter Park, FL 32789
Modern two-story home featuring minimalist landscaping, well-manicured lawn, and a glass front door at 1733 Harmon Ave, Winter Park, FL 32789
Modern two-story home with minimalist landscaping, a well-manicured lawn, and dark framed windows at 1733 Harmon Ave, Winter Park, FL 32789
On Market For 19 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3267

  • Year Built

    2025

  • $/SqFt

    $488

Lawndale - Located just minutes from the heart of Park Avenue Winter Park, downtown Orlando, and fine dining, boutique shopping, museums, and local cafés. SOUTH REALTY, INC.

Pended $650,000

A cozy single-story home with muted colors, shutters and mature landscaping at 1730 Oneco Ave, Winter Park, FL 32789
View of a lush backyard, featuring a screened-in porch at 1730 Oneco Ave, Winter Park, FL 32789
Spacious bedroom featuring a ceiling fan, closet and plenty of natural light at 1730 Oneco Ave, Winter Park, FL 32789
On Market For 19 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1408

  • Year Built

    1967

  • $/SqFt

    $462

Winter Park Heights - This winter park corner lot is highly sought after for its location and its potential. THE TEAM REAL ESTATE GROUP INC.

Pended $575,000

Inviting front porch with rocking chairs, and stately columns with decorative trim at 7852 Broken Arrow Trl, Winter Park, FL 32792
Bright and airy living room with large window, calming colors, and lots of comfortable seating at 7852 Broken Arrow Trl, Winter Park, FL 32792
Expansive open-concept kitchen with island seating, modern lighting, and light wood flooring at 7852 Broken Arrow Trl, Winter Park, FL 32792
On Market For 18 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2219

  • Year Built

    1972

  • $/SqFt

    $259

Don’t miss your chance to own this irresistible gem, set in the serene neighborhood you’ve been looking for. Schedule your private showing today! CREEGAN GROUP.

Pended $429,000

Charming single-story home with a well-maintained lawn and covered carport in a desirable neighborhood at 2809 Sanbina St, Winter Park, FL 32789
Sprawling backyard with a sparkling pool and lush landscaping at 2809 Sanbina St, Winter Park, FL 32789
Well maintained lawn, clean front exterior, and driveway parking at 2809 Sanbina St, Winter Park, FL 32789
On Market For 17 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1140

  • Year Built

    1961

  • $/SqFt

    $376

Howell Heights - Don't miss this incredible opportunity, schedule your showing today! STRONG FOUNDATION REALTY LLC.

Home For Sale $425,000

Well-kept single-Gathering home with lush lawn, mature trees, and classic brick and siding exterior at 3107 Ash Park Loop, Winter Park, FL 32792
Charming home with brick accents, mature landscaping, and well-maintained lawn, in a peaceful setting at 3107 Ash Park Loop, Winter Park, FL 32792
Spacious living room with tile flooring, fireplace, and a wall of mirrors reflecting natural light at 3107 Ash Park Loop, Winter Park, FL 32792
On Market For 19 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1518

  • Year Built

    1987

  • $/SqFt

    $280

This home will not last long. Schedule your showing today! COLDWELL BANKER REALTY.

Pended $575,000

Inviting single-story home with lush landscaping in front of the house and well-maintained bushes at 1387 Sawgrass Court, Winter Park, FL 32792
An aerial view of a lovely home near a golf course with lush greenery and a pond in a serene setting at 1387 Sawgrass Court, Winter Park, FL 32792
Aerial view of property near a golf course with lush greenery and a pond in a serene setting at 1387 Sawgrass Court, Winter Park, FL 32792
On Market For 20 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1867

  • Year Built

    1979

  • $/SqFt

    $308

Greenview Winter Pines - Recent updates include: New windows 2023-24, New AC 2022, New driveway 2022, New fence 2022, roof 2015, New electrical panel 2022, updated porcelain tile. WELCOME HOME! FANNIE HILLMAN & ASSOCIATES.

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 386 801 5417 and speak with one of our real estate consultants.

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