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173 Results

View 173 32789 Florida Homes for Sale

Home For Sale $1,554,950

Reduced By $40,000

Charming two-story home featuring stucco siding, a tile roof, arched windows, and a brick driveway at 952 Moss Ln, Winter Park, FL 32789
View Details 55 Photos
Charming two-story home featuring stucco siding, a tile roof, arched windows, and a brick driveway at 952 Moss Ln, Winter Park, FL 32789
Charming two-story home featuring stucco siding, a tile roof, arched windows, and a brick driveway at 952 Moss Ln, Winter Park, FL 32789
Side view of a charming two-story home featuring stucco siding, a tile roof, arched windows, and manicured landscaping at 952 Moss Ln, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 41 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    3474

  • Year Built

    2008

  • $/SqFt

    $448

Maitland Shores - Schedule a showing today and step into a lifestyle of comfort, sophistication, and unparalleled charm at 952 Moss Ln—a true gem ready to become your forever home. THE SHOP REAL ESTATE CO..

Home For Sale $2,590,000

Stunning two-story home featuring a black tile roof, white stucco, arched front door, and manicured landscaping at 185 Sylvan Blvd, Winter Park, FL 32789
View Details 9 Photos
Bright and airy living room with a modern fireplace, recessed lighting, and stylish furniture at 185 Sylvan Blvd, Winter Park, FL 32789
Gourmet kitchen featuring an island with seating, a custom range hood, and stainless steel appliances at 185 Sylvan Blvd, Winter Park, FL 32789
Serene bedroom with a tufted headboard, neutral color palette, and plenty of natural light at 185 Sylvan Blvd, Winter Park, FL 32789
On Market For 43 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3138

  • Year Built

    2025

  • $/SqFt

    $825

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

Home For Sale $1,595,000

Charming single-story home with a tile roof, a brick driveway, and well-manicured landscaping at 1741 Palmer Ave, Winter Park, FL 32789
View Details 59 Photos
An estate home features a tile roof, a paved driveway, mature landscaping, and a private gate at 1741 Palmer Ave, Winter Park, FL 32789
A stucco house has a tile roof, a two-car garage, a brick entry gate, and a paved driveway at 1741 Palmer Ave, Winter Park, FL 32789
A stucco house has a tile roof, a brick entry gate, a private driveway, and mature landscaping at 1741 Palmer Ave, Winter Park, FL 32789
On Market For 43 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2351

  • Year Built

    2013

  • $/SqFt

    $678

Jenkins - Perfectly situated on the iconic, tree-lined Palmer Avenue, this home offers unbeatable walkability—just a short stroll to Phelps Park and mere minutes from the boutiques and dining of Park Avenue, Interlachen Country Club, and the Winter Park Racquet Club- set up your private showing today. CENTRAL FLORIDA PRIME REAL ESTATE LLC.

Home For Sale $850,000

Charming single-story home boasting a mix of modern wood and white siding, manicured lawn, and inviting curb appeal at 730 W Swoope Ave, Winter Park, FL 32789
View Details 72 Photos
View of a single story home with a wood and white exterior, partially fenced in, located on a residential street at 730 W Swoope Ave, Winter Park, FL 32789
A well maintained lawn with a small tree in the front yard, compliments a modern single story home at 730 W Swoope Ave, Winter Park, FL 32789
Close up of the exterior featuring modern wood siding, a secured glass door, and a manicured front lawn at 730 W Swoope Ave, Winter Park, FL 32789
On Market For 44 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2132

  • Year Built

    1950

  • $/SqFt

    $399

Carver Town - Come discover your new corner home and fall in love with everything Winter Park has to offer. LPT REALTY, LLC.

Pended $599,000

Charming two-story home with black front door, manicured landscaping and mature trees at 490 Shoreview Ave, Winter Park, FL 32789
View Details 35 Photos
Charming two-story home with black front door, manicured landscaping and mature trees at 490 Shoreview Ave, Winter Park, FL 32789
Beautiful aerial view of neighborhood homes and lake with city skyline in the distance at 490 Shoreview Ave, Winter Park, FL 32789
Aerial view of home, lush backyard, a detached garage and neighboring properties at 490 Shoreview Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 43 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2266

  • Year Built

    1935

  • $/SqFt

    $264

Killarney Estates - Don’t miss your chance to call this historic gem home! FLORIDA HOME TEAM REALTY LLC.

Home For Sale $250,000

Reduced By $49,995

Charming home featuring a cozy porch, brick driveway, and mature trees enhancing curb appeal at 1996 Indiana Ave, Winter Park, FL 32789
View Details 3 Photos
Charming single-story home with a covered porch and white trim, surrounded by lush greenery and trees at 1996 Indiana Ave, Winter Park, FL 32789
Exterior view of a cozy single-story home with a covered porch, nestled amongst mature trees and foliage at 1996 Indiana Ave, Winter Park, FL 32789
On Market For 37 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    818

  • Year Built

    1938

  • $/SqFt

    $306

Lawndale - City water and sewer connections are available on the property. MARKET CONNECT REALTY LLC.

Home For Sale $1,999,900

Modern two-story home with meticulously landscaped front yard and paver driveway, surrounded by mature palm trees at 1521 Chestnut Ave, Winter Park, FL 32789
View Details 55 Photos
Charming two-story home with landscaped front yard, paver driveway, and modern architectural details at sunset at 1521 Chestnut Ave, Winter Park, FL 32789
Modern home featuring a private pool, covered patio, second story balcony and lush backyard at sunset at 1521 Chestnut Ave, Winter Park, FL 32789
Overhead view of modern home, showcasing the roof, pool, driveway, and landscaped yard surrounded by neighboring properties at 1521 Chestnut Ave, Winter Park, FL 32789
On Market For 47 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3117

  • Year Built

    2022

  • $/SqFt

    $642

Lake Knowles Terrace - Don't miss your chance to own this exceptional home in the heart of Winter Park! COMPASS FLORIDA LLC.

Home For Sale $414,999

Reduced By $5,001

Charming single-story home with a lush front yard, mature trees, and a covered carport showcasing curb appeal at 920 Gloriosa Ave, Winter Park, FL 32789
View Details 51 Photos
This backyard offers a serene, partially shaded space with trees, a small patio, and a well-maintained grassy area at 920 Gloriosa Ave, Winter Park, FL 32789
Charming single-story home with a lush front yard, mature trees, and a covered carport showcasing curb appeal at 920 Gloriosa Ave, Winter Park, FL 32789
A well-kept carport with a concrete floor, storage doors, and direct access to the home's entrance at 920 Gloriosa Ave, Winter Park, FL 32789
On Market For 47 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1540

  • Year Built

    1956

  • $/SqFt

    $269

Albert Lee Ridge - This home is a true gem—schedule your private showing today before it’s gone! EXP REALTY LLC.

Home For Sale $2,999,000

Reduced By $201,000

Stunning two-story home featuring a brick driveway, lush landscaping, and a welcoming front entrance at 1891 Lake Spier Dr, Winter Park, FL 32789
View Details 34 Photos
Bright living room featuring stylish seating, coffered ceiling, and sliding glass doors overlooking a beautiful lake at 1891 Lake Spier Dr, Winter Park, FL 32789
Open-concept kitchen featuring marble countertops, pendant lighting, and seamless flow into the living space at 1891 Lake Spier Dr, Winter Park, FL 32789
Well-appointed kitchen island with seating, pendant lights, and stylish backsplash at 1891 Lake Spier Dr, Winter Park, FL 32789
On Market For 48 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3932

  • Year Built

    2024

  • $/SqFt

    $763

South Lakemont Shores - Call today to schedule your private showing. LPT REALTY, LLC.

Pended $2,375,000

Charming two-story home featuring a balcony, manicured lawn, and brick accents at 104 Cortland Ave, Winter Park, FL 32789
View Details 65 Photos
Charming two-story home featuring a balcony, manicured lawn, and brick accents at 104 Cortland Ave, Winter Park, FL 32789
Landscaped front yard with manicured hedges, stone walkway, and lush greenery at 104 Cortland Ave, Winter Park, FL 32789
Inviting front entrance with brick columns, landscaped garden, and stone walkway at 104 Cortland Ave, Winter Park, FL 32789
On Market For 44 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3182

  • Year Built

    1926

  • $/SqFt

    $746

Cortland Park - This residence is a compelling blend of character, craftsmanship and contemporary living. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $499,000

Charming home with a welcoming front porch, manicured landscaping, and classic curb appeal at 674 Douglas Ave, Winter Park, FL 32789
View Details 33 Photos
Charming home with a welcoming front porch, manicured landscaping, and classic curb appeal at 674 Douglas Ave, Winter Park, FL 32789
Charming home featuring a blue door, white picket fence, well-manicured landscaping, and a private, fenced driveway at 674 Douglas Ave, Winter Park, FL 32789
Kitchen with granite island, vaulted ceiling, stainless steel appliances, and eating area at 674 Douglas Ave, Winter Park, FL 32789
On Market For 48 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1260

  • Year Built

    1925

  • $/SqFt

    $396

The roof was updated in December 2023, and the air conditioning unit was replaced in 2019, the air-conditioning compressor in 2022, and the water heater in 2019. PREMIER SOTHEBYS INT'L REALTY.

Home For Sale $2,900,000

Stunning home featuring a stone turret, red tile roof, and lush, manicured landscaping at 1401 Green Cove Rd, Winter Park, FL 32789
View Details 77 Photos
Charming two-story home boasts a stone turret, red tile roof and well-maintained lawn at 1401 Green Cove Rd, Winter Park, FL 32789
Beautiful home with a stone turret, red tile roof, two-car garage, and verdant lawn at 1401 Green Cove Rd, Winter Park, FL 32789
Lovely home features a stone archway, balcony, and professionally landscaped front yard at 1401 Green Cove Rd, Winter Park, FL 32789
On Market For 50 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    5416

  • Year Built

    2009

  • $/SqFt

    $535

Camwood - Please see Matterport link for layout of this Beautiful Home. BUCKEYE REALTY LLC.

Home For Sale $1,888,000

Striking two-story home with modern design, manicured lawn, and a spacious two-car garage at 2407 Lafayette Ave, Winter Park, FL 32789
View Details 35 Photos
Charming two-story home boasts a modern design, manicured lawn, and a spacious driveway leading to the two-car garage at 2407 Lafayette Ave, Winter Park, FL 32789
Bright entryway with hardwood floors, modern decor, and a view of the outdoors through a glass door at 2407 Lafayette Ave, Winter Park, FL 32789
Bright office space features hardwood floors, a comfortable seating area, and ample natural light at 2407 Lafayette Ave, Winter Park, FL 32789
On Market For 49 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3133

  • Year Built

    2018

  • $/SqFt

    $603

Fontainebleau - Don’t miss this rare opportunity to own a one-of-a-kind home in one of Central Florida’s premier neighborhoods. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $349,000

Reduced By $40,900

Charming single-story home with a bright blue and white exterior, red door, and well-maintained landscaping at 657 Overspin Dr, Winter Park, FL 32789
View Details 25 Photos
Dining room features light wood floors, dining table with seating for four, and decorative art pieces at 657 Overspin Dr, Winter Park, FL 32789
Spacious living room features light wood floors, a comfortable couch, and a decorative rug at 657 Overspin Dr, Winter Park, FL 32789
Bright living room with large windows, comfortable seating, and a stylish round coffee table at 657 Overspin Dr, Winter Park, FL 32789
On Market For 49 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1349

  • Year Built

    1955

  • $/SqFt

    $259

Dubsdread Heights - RE/MAX 200 REALTY.

Pended $995,000

Reduced By $105,000

Charming home featuring a two-car garage, solar panels, and well-manicured landscaping with a spacious driveway at 1821 Windsor Dr, Winter Park, FL 32789
View Details 66 Photos
Attractive home showcasing solar panels, a spacious driveway, and a manicured lawn with tasteful landscaping at 1821 Windsor Dr, Winter Park, FL 32789
Inviting home exterior highlighting a two-car garage, stone accents, and landscaped garden with a paved walkway at 1821 Windsor Dr, Winter Park, FL 32789
Welcoming front porch with stone pillars, stylish seating, and a contemporary front door, creating curb appeal at 1821 Windsor Dr, Winter Park, FL 32789
On Market For 50 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2188

  • Year Built

    2017

  • $/SqFt

    $455

It's a One-of-a-Kind Home! Book your appointment today! CREEGAN GROUP.

Home For Sale $3,150,000

Elegant white two-story home with symmetrical windows, shutters, and landscaped front yard at 541 W Canton Ave, Winter Park, FL 32789
View Details 49 Photos
Stunning white two-story home featuring symmetrical design, shuttered windows, and a charming brick pathway at 541 W Canton Ave, Winter Park, FL 32789
Bright dining room featuring a chandelier, light pink walls, and glass doors leading to the patio at 541 W Canton Ave, Winter Park, FL 32789
Elegant dining room with modern chandelier, farm table, and glass doors to the outside at 541 W Canton Ave, Winter Park, FL 32789
On Market For 53 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3553

  • Year Built

    2024

  • $/SqFt

    $887

This masterpiece set in the heart of Winter Park, thoughtfully surrounded by lush landscaping and carefully placed privacy screens, offers polish and presence in the perfect location. KELLER WILLIAMS WINTER PARK.

Home For Sale $999,000

Reduced By $101,000

Charming two-story home with a two-car garage, black trim, and mature trees offering ample shade at 913 Moss Ln, Winter Park, FL 32789
View Details 38 Photos
Aerial view of the home nestled among mature trees with a large, fenced backyard at 913 Moss Ln, Winter Park, FL 32789
Two story home with a two car garage, a long driveway, and mature shade trees at 913 Moss Ln, Winter Park, FL 32789
Two-story home with a 2-car garage, dark trim and a concrete driveway at 913 Moss Ln, Winter Park, FL 32789
On Market For 54 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1887

  • Year Built

    1953

  • $/SqFt

    $529

Maitland Shores - Don’t let this rare opportunity slip away—913 Moss Lane is your chance to own a fully updated masterpiece, so schedule your exclusive showing now and step into the life you’ve always dreamed of—call today before this gem is gone! VECTOR PROPERTY GROUP.

Home For Sale $3,600,000

Stunning two-story home featuring a modern design, three-car garage, and beautifully landscaped front yard at 182 N Phelps Ave, Winter Park, FL 32789
View Details 57 Photos
Beautifully landscaped two-story home with a three-car garage and modern architectural design at 182 N Phelps Ave, Winter Park, FL 32789
Two-story home with three-car garage, modern architectural design, landscaped front yard, and paver driveway at 182 N Phelps Ave, Winter Park, FL 32789
Exterior home featuring a modern design, three-car garage, and illuminated architectural details at twilight at 182 N Phelps Ave, Winter Park, FL 32789
On Market For 47 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    4812

  • Year Built

    2025

  • $/SqFt

    $748

Golfview - In conclusion, the home exhibits a smooth blend of advanced technology and high-end finishes, promising a luxurious living experience! LA ROSA REALTY HORIZONS LLC.

Pended $2,495,000

Reduced By $855,000

Beautiful home featuring a winding brick drive, lush landscaping, and a second-story balcony, offering great curb appeal at 940 Lincoln Cir, Winter Park, FL 32789
View Details 81 Photos
Stunning white home with manicured landscaping, a metal roof, and a second-story balcony offers luxurious curb appeal at 940 Lincoln Cir, Winter Park, FL 32789
Charming home entrance featuring manicured shrubs, a brick pathway, and covered porch at 940 Lincoln Cir, Winter Park, FL 32789
Charming porch with seating area overlooking lush landscape at 940 Lincoln Cir, Winter Park, FL 32789
On Market For 52 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3551

  • Year Built

    1995

  • $/SqFt

    $703

A rare opportunity in Winter Park’s most walkable and desirable neighborhood. KELLY PRICE & COMPANY LLC.

Home For Sale $1,625,000

Reduced By $174,000

Charming home with well-manicured lawn and pathway leading to the front door, shaded by mature trees at 1742 Barcelona Way, Winter Park, FL 32789
View Details 62 Photos
Inviting home exterior showcasing a lush lawn and brick driveway framed by mature trees and landscaping at 1742 Barcelona Way, Winter Park, FL 32789
Charming home with well-manicured lawn and pathway leading to the front door, shaded by mature trees at 1742 Barcelona Way, Winter Park, FL 32789
Home exterior with lush lawn, mature trees, and a brick pathway leading to the front entrance at 1742 Barcelona Way, Winter Park, FL 32789
On Market For 54 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    3626

  • Year Built

    1973

  • $/SqFt

    $448

This one-of-a-kind estate home is truly special and a must-see. KELLY PRICE & COMPANY LLC.

Home For Sale $299,000

Reduced By $16,000

Charming single-story home featuring a cozy front porch and well-maintained lawn with mature trees at 849 Driver Ave, Winter Park, FL 32789
View Details 31 Photos
Inviting home exterior showcases a small front porch, attached garage, and a lush green lawn at 849 Driver Ave, Winter Park, FL 32789
Aerial view of single-story home featuring a small front porch, attached garage, and well-maintained lawn at 849 Driver Ave, Winter Park, FL 32789
Bright sun room with large windows offering plenty of natural light and pleasant outdoor views at 849 Driver Ave, Winter Park, FL 32789
On Market For 43 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    894

  • Year Built

    1957

  • $/SqFt

    $334

Dubsdread Heights - Don’t miss out—schedule your showing today! CASTLE & COTTAGE REALTY LLC.

Home For Sale $3,595,000

Reduced By $385,000

Elegant two-story home featuring lush landscaping and a classic architectural design at 141 S Phelps Ave, Winter Park, FL 32789
View Details 60 Photos
Beautiful home exterior with stone pillar, lush landscaping, and mature trees at 141 S Phelps Ave, Winter Park, FL 32789
Covered outdoor living space with a built-in kitchen, comfortable seating, and pool view at 141 S Phelps Ave, Winter Park, FL 32789
Inviting backyard pool area surrounded by lush landscaping and patio seating at 141 S Phelps Ave, Winter Park, FL 32789
On Market For 55 Days

  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    5878

  • Year Built

    2006

  • $/SqFt

    $612

Windsong Lakeside - Don't miss the opportunity to own this spectacular home in one of Winter Park's most sought after neighborhoods with its top-rated schools, and proximity to shopping and dining on Park Avenue in picturesque downtown Winter Park! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $1,695,000

Stunning two-story modern home with stone accents and a spacious three-car garage at 1831 Mizell Ave, Winter Park, FL 32789
View Details 40 Photos
Inviting front entrance with stylish door, stone accents, and manicured landscaping at 1831 Mizell Ave, Winter Park, FL 32789
Contemporary two-story home boasts striking stone accents and a three-car garage at 1831 Mizell Ave, Winter Park, FL 32789
Bright and modern foyer with hardwood floors, glass-railed staircase, and elegant lighting at 1831 Mizell Ave, Winter Park, FL 32789
On Market For 56 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3204

  • Year Built

    2016

  • $/SqFt

    $529

Zoned for A-rated Brookshire Elementary, Glenridge Middle, and Winter Park High School. MORE PICTURES FRIDAY! EXP REALTY LLC.

Home For Sale $2,725,000

Reduced By $100,000

Stately two-story home featuring a manicured lawn, dormer windows, and light blue shutters, exuding classic elegance at 1400 Place Picardy, Winter Park, FL 32789
View Details 44 Photos
Elegant home featuring an expansive lawn, a second-story balcony, and contrasting light blue shutters for a stylish look at 1400 Place Picardy, Winter Park, FL 32789
Inviting backyard pool area with stylish outdoor seating, lush greenery, and a charming pool house at 1400 Place Picardy, Winter Park, FL 32789
Relaxing pool with lounge area, surrounded by lush greenery, perfect for outdoor entertaining at 1400 Place Picardy, Winter Park, FL 32789
On Market For 59 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4338

  • Year Built

    2008

  • $/SqFt

    $628

Fontainebleau - Don’t miss this rare opportunity to own a truly exceptional home in one of Central Florida’s most desirable communities. CORCORAN PREMIER REALTY.

Home For Sale $950,000

Reduced By $50,000

Charming single-story home with white siding, black trim, manicured landscaping, and a welcoming entryway at 3011 Temple Trl, Winter Park, FL 32789
View Details 39 Photos
Relaxing outdoor patio features comfortable seating, ceiling fans, and views of the pool and lush backyard at 3011 Temple Trl, Winter Park, FL 32789
Serene aerial view of home surrounded by lush greenery and lakes, with a pin marking the property location at 3011 Temple Trl, Winter Park, FL 32789
Beautiful aerial view showcases a home with solar panels, pool, a well-manicured lawn, and surrounded by lush trees at 3011 Temple Trl, Winter Park, FL 32789
On Market For 59 Days

  • Bedrooms

    5

  • Full Bath(s)

    2

  • Sq. Ft.

    2406

  • Year Built

    1965

  • $/SqFt

    $395

Call today to schedule your tour! WEMERT GROUP REALTY LLC.

Home For Sale $475,000

Reduced By $20,000

Charming single-story home featuring a well-maintained lawn, covered porch and a convenient attached garage at 2886 Carew Ave, Winter Park, FL 32789
View Details 37 Photos
Single-story home with tidy landscaping, covered entryway, and attached garage for convenience and curb appeal at 2886 Carew Ave, Winter Park, FL 32789
Inviting tiled front porch with vibrant flowers, complemented by a blue-trimmed door and adjacent window at 2886 Carew Ave, Winter Park, FL 32789
Bright living room with dark floors, showcasing a large window offering ample natural light and airy feel at 2886 Carew Ave, Winter Park, FL 32789
On Market For 62 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1766

  • Year Built

    1956

  • $/SqFt

    $269

Fairbanks Shores - A quiet neighborhood in the coveted Edgewater High School district, this home is just waiting to be discovered. Make your showing appointment today. OLDE TOWN BROKERS INC.

Pended $2,749,000

Reduced By $100,000

Two-story home featuring a manicured lawn, a three-car garage, and neatly trimmed hedges and bushes at 1690 Palm Ave, Winter Park, FL 32789
View Details 53 Photos
Two-story home with a brick driveway, a well-maintained lawn, and beautiful landscaping at 1690 Palm Ave, Winter Park, FL 32789
Front exterior view of a white two-story home with well-maintained landscaping, including palm trees at 1690 Palm Ave, Winter Park, FL 32789
The side yard of this home features manicured hedges, flowers and a stepping stone pathway to a black metal gate at 1690 Palm Ave, Winter Park, FL 32789
On Market For 61 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3967

  • Year Built

    2020

  • $/SqFt

    $693

Winter Park Heights - Amenities include: granite & quartz counter tops, Level 4 smooth finish walls & ceilings, hardwood floors in all main living areas, custom closet systems, brick paved driveway, PGT vinyl Low E insulated windows, core fill & block walls, high density spray foam insulation in ceilings, R13 in walls, Trane 16 Seer variable speed AC dual systems & 2 tankless water heaters. HOUWZER INC.

Home For Sale $1,999,500

Reduced By $95,500

Stunning two-story home boasts a meticulously landscaped yard and elegant modern architectural details at 1840 Bryan Ave, Winter Park, FL 32789
View Details 47 Photos
Beautiful two-story home with manicured lawn and inviting entrance, exuding curb appeal at 1840 Bryan Ave, Winter Park, FL 32789
Inviting pool area with fountains, a fire feature, and cozy patio seating for outdoor relaxation at 1840 Bryan Ave, Winter Park, FL 32789
Serene backyard retreat featuring Adirondack chairs, artificial turf, and lush landscaping at 1840 Bryan Ave, Winter Park, FL 32789
On Market For 62 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3727

  • Year Built

    2014

  • $/SqFt

    $536

A mile from Park Avenue, close to hospital and walkable to the YMCA, Phelps Park and fantastic restaurants. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $675,000

Charming single-story home with a brick walkway, covered porch, and well-maintained landscaping at 1399 Aloma Ave, Winter Park, FL 32789
View Details 38 Photos
Welcoming exterior view showcasing landscaped garden, covered porch, and vibrant curb appeal at 1399 Aloma Ave, Winter Park, FL 32789
Cozy front porch with seating, stylish lighting, and unique address plaque detail at 1399 Aloma Ave, Winter Park, FL 32789
Inviting front entrance featuring a bright red door, decorative plants, and a well-lit porch at 1399 Aloma Ave, Winter Park, FL 32789
On Market For 63 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1804

  • Year Built

    1948

  • $/SqFt

    $374

Fix426 improvements starting Spring 2026. Schedule your showing today! FLORIDA HOMES REALTY & MTG.

Home For Sale $1,350,000

Reduced By $50,000

Contemporary home boasts a modern design, featuring a well-manicured lawn, sleek lines and a stylish wood garage door at 2525 Venetian Way, Winter Park, FL 32789
View Details 66 Photos
Contemporary home boasts a manicured lawn, complemented by the home's sleek lines and modern landscape design at 2525 Venetian Way, Winter Park, FL 32789
Modern home featuring a statement driveway, manicured lawn and unique architectural elements at 2525 Venetian Way, Winter Park, FL 32789
Front porch with striking front door and stone accents and landscape at 2525 Venetian Way, Winter Park, FL 32789
On Market For 64 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1993

  • Year Built

    1953

  • $/SqFt

    $677

Maitland Shores - Enjoy exclusive canal access to Lake Maitland for small watercraft in this quiet, community. KELLY PRICE & COMPANY LLC.

Home For Sale $800,000

Charming two-story home with manicured lawn, brick accents, and a secure, decorative black metal fence at 441 N Capen Ave, Winter Park, FL 32789
View Details 36 Photos
Charming two-story home featuring brick accents and decorative black metal fence with a paved walkway at 441 N Capen Ave, Winter Park, FL 32789
Charming two-story home featuring brick accents and decorative black metal fence in a residential area at 441 N Capen Ave, Winter Park, FL 32789
Welcoming foyer with hardwood floors, stairs, and a white front door, offering a bright entrance at 441 N Capen Ave, Winter Park, FL 32789
On Market For 64 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1745

  • Year Built

    2017

  • $/SqFt

    $458

Best value in 32789 zip code!!! Call today for your showing. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $2,295,000

Modern two-story home featuring clean lines, a balcony, a two-car garage, and lush tropical landscaping at 1760 Bryan Ave, Winter Park, FL 32789
View Details 2 Photos
Modern two-story home featuring a pool, outdoor kitchen, and large windows offering a sun-filled interior at 1760 Bryan Ave, Winter Park, FL 32789
On Market For 65 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3005

  • Year Built

    2026

  • $/SqFt

    $764

Perfectly positioned just minutes from the boutiques, restaurants, and cultural experiences of Park Avenue, this residence captures the essence of modern living in one of Central Florida’s most coveted neighborhoods. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,799,000

Reduced By $301,000

Elegant home exterior featuring illuminated address numbers, manicured lawn, and three-car garage at 2402.5 Temple Dr, Winter Park, FL 32789
View Details 39 Photos
Charming two-story home with manicured lawn, stone accents, and professionally landscaped yard at 2402.5 Temple Dr, Winter Park, FL 32789
Beautifully landscaped home with lush green lawn, elegant shrubs, and tranquil twilight view at 2402.5 Temple Dr, Winter Park, FL 32789
Inviting front porch with stone columns, manicured hedges, and stylish entryway at 2402.5 Temple Dr, Winter Park, FL 32789
On Market For 65 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3248

  • Year Built

    2015

  • $/SqFt

    $554

Call today for an easy showing! OLDE TOWN BROKERS INC.

Home For Sale $1,325,000

Reduced By $125,000

Charming single-story home with well-manicured landscaping, brick driveway, and inviting front entrance at 2105 Fosgate Dr, Winter Park, FL 32789
View Details 58 Photos
Aerial view of a well-maintained single-story home with a lush green lawn, mature trees, and a brick driveway at 2105 Fosgate Dr, Winter Park, FL 32789
Bright kitchen with stainless steel appliances, farmhouse sink, patterned backsplash, and custom vent hood at 2105 Fosgate Dr, Winter Park, FL 32789
Spacious kitchen with a large island, pendant lighting, stainless steel appliances, and custom wood accents at 2105 Fosgate Dr, Winter Park, FL 32789
On Market For 65 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3068

  • Year Built

    1956

  • $/SqFt

    $432

All Double Pane Aluminum Windows throughout home. LPT REALTY, LLC.

Pended $669,000

Reduced By $30,000

Inviting front yard with lush landscaping and a charming, paved walkway leading to the home at 2711 Parkland Dr, Winter Park, FL 32789
View Details 14 Photos
Welcoming entrance featuring a decorative address plaque and a secure wooden gate at 2711 Parkland Dr, Winter Park, FL 32789
Charming backyard with a pergola-covered patio and a well-maintained walkway at 2711 Parkland Dr, Winter Park, FL 32789
Spacious living room with a fireplace, new floors and ample natural light at 2711 Parkland Dr, Winter Park, FL 32789
On Market For 48 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1618

  • Year Built

    1938

  • $/SqFt

    $413

Parklando - This exceptional home offers the quintessential Winter Park lifestyle in a location that combines established neighborhood character with exciting urban accessibility. CORCORAN PREMIER REALTY.

Home For Sale $1,470,000

Reduced By $25,000

Charming single-story home featuring a neatly landscaped front yard, circular driveway and a vibrant blue front door at 1644 Hibiscus Ave, Winter Park, FL 32789
View Details 16 Photos
Landscaped front yard featuring a circular driveway and mature magnolia tree providing ample shade at 1644 Hibiscus Ave, Winter Park, FL 32789
Well-maintained single-story home with a large front lawn, circular driveway, and carefully manicured landscaping at 1644 Hibiscus Ave, Winter Park, FL 32789
Exterior shot of a home showcasing a circular driveway, well-manicured lawn, and mature trees at 1644 Hibiscus Ave, Winter Park, FL 32789
On Market For 69 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2145

  • Year Built

    1974

  • $/SqFt

    $685

Flora Park - This is more than a home—it's an opportunity to live in one of Winter Park's most iconic neighborhoods. COLDWELL BANKER RESIDENTIAL RE.

Pended $1,200,000

Reduced By $75,000

Charming single-story brick home featuring a well-manicured lawn and an attached two-car garage at 309 Park North Ct, Winter Park, FL 32789
View Details 55 Photos
Charming single-story brick home featuring a well-manicured lawn and an attached two-car garage at 309 Park North Ct, Winter Park, FL 32789
Inviting home entrance with a decorative double door, brick pathway, and manicured landscaping at 309 Park North Ct, Winter Park, FL 32789
Spacious living room featuring neutral tile flooring, recessed lighting, and a view to the backyard at 309 Park North Ct, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 66 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3096

  • Year Built

    1968

  • $/SqFt

    $388

Schedule your private showing today and explore the possibilities! ** SURVEY AVAILABLE IN ATTACHMENTS ** FANNIE HILLMAN & ASSOCIATES.

Pended $1,025,000

Charming brick home with manicured landscaping and a paver driveway, showcasing classic design and curb appeal at 2923 Cove Trl, Winter Park, FL 32789
View Details 53 Photos
Well-appointed kitchen with an island, dark wood cabinetry, stainless steel appliances, and hardwood floors at 2923 Cove Trl, Winter Park, FL 32789
Spacious home office with hardwood floors, built-in shelving, and ample desk space for productivity at 2923 Cove Trl, Winter Park, FL 32789
Temperature-controlled wine cellar featuring custom shelving and storage for an extensive collection at 2923 Cove Trl, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 66 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3377

  • Year Built

    1964

  • $/SqFt

    $304

*CLICK on Virtual tour link for 3D Walk Through. * KELLER WILLIAMS ADVANTAGE III.

Home For Sale $670,000

Charming one-story home with a carport and well-maintained front yard, offering inviting curb appeal at 3006 Northwood Blvd, Winter Park, FL 32789
View Details 4 Photos
Coverage sheet including square footage for 3006 Northwood Blvd showing setbacks and square footage coverage at 3006 Northwood Blvd, Winter Park, FL 32789
This document details minimum setbacks allowed for the property and also lists existing setbacks at 3006 Northwood Blvd, Winter Park, FL 32789
Survey shows property lines, landscaping, and the location of the home at 3006 Northwood Blvd at 3006 Northwood Blvd, Winter Park, FL 32789
On Market For 69 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1729

  • Year Built

    1953

  • $/SqFt

    $388

Northwood Terrace - Enjoy walking distance to local favorites like East End Market, Kelly’s Ice Cream, Redlight Redlight, and Sushi Lola. ORLANDO HOMES GROUP LLC.

Pended $1,150,000

Charming two-story home featuring a striking red front door and professionally landscaped front yard at 795 W Canton Ave, Winter Park, FL 32789
View Details 61 Photos
Charming two-story home showcasing a beautifully landscaped front yard and a striking red front door at 795 W Canton Ave, Winter Park, FL 32789
Aerial view of the home featuring a well-manicured lawn and mature landscaping at 795 W Canton Ave, Winter Park, FL 32789
Charming two-story home featuring a striking red front door and professionally landscaped front yard at 795 W Canton Ave, Winter Park, FL 32789
On Market For 28 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2374

  • Year Built

    2017

  • $/SqFt

    $484

Don't miss this rare opportunity to own a modern gem in one of Central Florida’s most sought-after neighborhoods! WEICHERT REALTORS HALLMARK PROPERTIES.

Home For Sale $499,000

Spacious back yard with mature trees and shade for outdoor enjoyment at 3601 Midiron Dr, Winter Park, FL 32789
View Details 24 Photos
Charming home featuring a cozy front porch and well-maintained landscaping at 3601 Midiron Dr, Winter Park, FL 32789
Fenced side yard with a grill, utility connections, and mature landscaping at 3601 Midiron Dr, Winter Park, FL 32789
Back yard with patio area, perfect for outdoor dining and relaxing at 3601 Midiron Dr, Winter Park, FL 32789
On Market For 70 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    954

  • Year Built

    1945

  • $/SqFt

    $523

Golfview - Schedule your showing and don't miss this incredible opportunity! EMPIRE NETWORK REALTY.

Pended $2,490,000

Reduced By $85,000

Stunning two-story home featuring a modern design, well-manicured landscaping, and a paved driveway at 1795 Greenwich Ave, Winter Park, FL 32789
View Details 77 Photos
Beautiful front entrance with a stone walkway, manicured landscaping, and a stylish modern door at 1795 Greenwich Ave, Winter Park, FL 32789
Bright and airy living room with a comfortable gray sectional, wood floors, and access to the outdoors at 1795 Greenwich Ave, Winter Park, FL 32789
Stylish living room showcasing a modern fireplace, comfortable seating, and large windows at 1795 Greenwich Ave, Winter Park, FL 32789
On Market For 36 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3852

  • Year Built

    2019

  • $/SqFt

    $646

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

Home For Sale $1,299,000

Charming two-story home with landscaped front yard and inviting brick paver driveway at 1341 Lyndale Blvd, Winter Park, FL 32789
View Details 45 Photos
Beautiful home featuring a brick driveway, lush lawn, and meticulous landscaping at 1341 Lyndale Blvd, Winter Park, FL 32789
Inviting front entryway with a stylish light fixture and elegant glass-paneled door at 1341 Lyndale Blvd, Winter Park, FL 32789
Elegant hallway features hardwood floors, archways, and modern chandelier at 1341 Lyndale Blvd, Winter Park, FL 32789
On Market For 72 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2388

  • Year Built

    2007

  • $/SqFt

    $544

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

Home For Sale $2,175,000

Reduced By $120,000

Elegant two-story home featuring a tile roof, balcony, and lush landscaping at 2614 Parkland Dr, Winter Park, FL 32789
View Details 73 Photos
Aerial view of the home showcasing pool, landscaping, and architectural style at 2614 Parkland Dr, Winter Park, FL 32789
Stunning backyard featuring a pristine pool, spa, and an outdoor fireplace for relaxing and entertaining 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
On Market For 71 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3307

  • Year Built

    2007

  • $/SqFt

    $658

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 $3,750,000

Reduced By $100,000

Elegant two-story home featuring a manicured lawn, blue shutters, and a light gray metal roof at 2171 Forrest Rd, Winter Park, FL 32789
View Details 42 Photos
Elegant two-story home featuring a manicured lawn, blue shutters, and a light gray metal roof at 2171 Forrest Rd, Winter Park, FL 32789
Backyard pool with waterfall feature, adjacent cabana, landscaping, and lounge chairs at 2171 Forrest Rd, Winter Park, FL 32789
Outdoor kitchen with stone, wood ceiling, modern appliances and dining with pool views at 2171 Forrest Rd, Winter Park, FL 32789
On Market For 75 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4565

  • Year Built

    2016

  • $/SqFt

    $821

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

Home For Sale $2,950,000

Reduced By $245,000

Stunning home featuring manicured lawns, a symmetrical facade, and a welcoming driveway framed by lush landscaping at 1020 Mayfield Ave, Winter Park, FL 32789
View Details 49 Photos
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 75 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2663

  • Year Built

    1989

  • $/SqFt

    $1,108

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

Pended $2,550,000

Reduced By $100,000

Contemporary two-story home featuring a modern design, manicured landscaping, and a spacious driveway at 1700 Palm Ave, Winter Park, FL 32789
View Details 35 Photos
Contemporary home boasts a modern facade, two-car garage, manicured lawn, and an elegant design at 1700 Palm Ave, Winter Park, FL 32789
Aerial view of a modern home with a backyard oasis including a swimming pool, patio, and lush green 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 75 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3770

  • Year Built

    2016

  • $/SqFt

    $676

Winter Park Heights - 1700 Palm Ave. delivers fabulous living in one of Central Florida’s most coveted neighborhoods. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $3,490,000

Modern two-story home featuring a manicured lawn, brick accents, and black trim windows at 1910 Glencoe Rd, Winter Park, FL 32789
View Details 12 Photos
A modern kitchen boasts a marble island with seating and designer pendant lighting at 1910 Glencoe Rd, Winter Park, FL 32789
Bright living room with fireplace, custom built-ins, wood beam ceiling, and large windows at 1910 Glencoe Rd, Winter Park, FL 32789
Relaxing bedroom featuring a four-poster bed, an accent chair, and a full glass exterior door at 1910 Glencoe Rd, Winter Park, FL 32789
On Market For 78 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

Beautiful two-story home featuring a well-manicured lawn, a palm tree, and a sleek, modern design at 532 Worthington Dr, Winter Park, FL 32789
View Details 100 Photos
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 78 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 $360,200

Charming single-story home with well-maintained landscaping and a decorative entryway at 320 Granada Dr, Winter Park, FL 32789
View Details 26 Photos
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 20 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1401

  • Year Built

    1946

  • $/SqFt

    $257

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

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