287 Results

View 287 Winter Park Florida Homes for Sale

Home For Sale $1,580,000

Inviting front porch featuring elegant columns, stone walkway, and attractive landscaping at 1750 Winchester Dr, Winter Park, FL 32789
Close up of the front porch with seating, charming décor, and a beautifully crafted wood door at 1750 Winchester Dr, Winter Park, FL 32789
Open-concept kitchen featuring a blue island, bar seating, and modern finishes at 1750 Winchester Dr, Winter Park, FL 32789
On Market For 31 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2637

  • Year Built

    1960

  • $/SqFt

    $599

Reside in one of Orlando’s friendliest and family-centric neighborhoods, all in style and turnkey comfort. FANNIE HILLMAN & ASSOCIATES.

Pended $719,000

Inviting living room with a fireplace, wood-look floors, and a seamless flow to the kitchen at 2003 Woodcrest Dr, Winter Park, FL 32792
Comfortable living room featuring a plush sofa, stylish rug, and ample natural light at 2003 Woodcrest Dr, Winter Park, FL 32792
Open-concept living space with a fireplace, dining area, and access to the outdoor pool at 2003 Woodcrest Dr, Winter Park, FL 32792
On Market For 31 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1734

  • Year Built

    1961

  • $/SqFt

    $415

Super location with fun neighborhood, block parties on holidays! KELLER WILLIAMS WINTER PARK.

Pended $695,000

Inviting single-story home with a well-maintained lawn and lush, green shrubbery at 604 Darcey Dr, Winter Park, FL 32792
Beautiful single story home features a well-manicured lawn and mature trees at 604 Darcey Dr, Winter Park, FL 32792
Home with a large garage, manicured lawn, and well-maintained landscaping at 604 Darcey Dr, Winter Park, FL 32792
On Market For 30 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2258

  • Year Built

    1968

  • $/SqFt

    $308

Don’t miss the opportunity to make this home yours! NEW ROOF coming March 2025. KELLY PRICE & COMPANY LLC.

Pended $415,000

Charming single Gathering home with a well maintained front yard and long private driveway at 7549 Dockside St, Winter Park, FL 32792
Modern kitchen featuring a large island, stainless steel appliances, and ample cabinet space at 7549 Dockside St, Winter Park, FL 32792
Bright living room with a ceiling fan, large window and an open floor plan at 7549 Dockside St, Winter Park, FL 32792
On Market For 31 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1245

  • Year Built

    1973

  • $/SqFt

    $333

Schedule your showing ASAP to see and purchase this home. COLDWELL BANKER REALTY.

Home For Sale $1,500,000

Contemporary home showcasing manicured landscaping, a stone driveway, and stylish architectural design at 2015 Summerfield Rd, Winter Park, FL 32792
Bright hallway with neutral walls, recessed lighting, and sleek tile flooring at 2015 Summerfield Rd, Winter Park, FL 32792
Cozy living room with comfortable seating, stylish decor, and a view of the pool at 2015 Summerfield Rd, Winter Park, FL 32792
On Market For 31 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2958

  • Year Built

    1957

  • $/SqFt

    $507

This home is located just minutes from Downtown Baldwin Park, Winter Park, Rollins College, and a variety of restaurants and shopping venues. BEYCOME OF FLORIDA LLC.

Pended $649,000

Beautiful home showcasing well-maintained landscaping, a quaint walkway, and a bright, welcoming facade at 721 Glenridge Way, Winter Park, FL 32789
Inviting outdoor patio with a turquoise table set and lush artificial turf, perfect for relaxing or entertaining at 721 Glenridge Way, Winter Park, FL 32789
Welcoming front entrance with a dark wood door, tiled flooring, and decorative plants for added curb appeal at 721 Glenridge Way, Winter Park, FL 32789
On Market For 21 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1545

  • Year Built

    1981

  • $/SqFt

    $420

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

Home For Sale $820,000

Reduced By $30,000

Front entryway featuring a gray front door adorned with a decorative wreath and white stucco walls at 5618 Winterbrook Way, Winter Park, FL 32792
Bright entryway with wood-look tile flooring, a shiplap accent wall, and a modern light fixture at 5618 Winterbrook Way, Winter Park, FL 32792
Staircase and entryway featuring wood stairs, white shiplap accent wall and wood-look tile flooring at 5618 Winterbrook Way, Winter Park, FL 32792
On Market For 33 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    2866

  • Year Built

    2020

  • $/SqFt

    $286

Don’t miss your chance to own this high-end, move-in-ready home in one of Winter Park’s most sought-after communities! Schedule your private showing today! REDFIN CORPORATION.

Pended $372,000

Welcoming single-story home with brick accents, a two-car garage, and a well-manicured lawn at 5339 Cypress Dr, Winter Park, FL 32792
Functional kitchen with stainless steel appliances, wood cabinetry, and ample counter space at 5339 Cypress Dr, Winter Park, FL 32792
Bright living room featuring a large window with natural light, neutral carpeting, and comfortable seating at 5339 Cypress Dr, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 33 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1782

  • Year Built

    1975

  • $/SqFt

    $209

Perfect for FHA 203k renovation mortgage FUTURE HOME REALTY INC.

Home For Sale $4,500,000

Charming white home showcasing a whimsical blue sky door and manicured front yard at 1336 College Pt, Winter Park, FL 32789
Beautiful backyard features an in-ground pool, lounge chairs, and guest house surrounded by green lawns at 1336 College Pt, Winter Park, FL 32789
Waterfront view of home with boat dock, lush lawns and tall trees at 1336 College Pt, Winter Park, FL 32789
On Market For 34 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3181

  • Year Built

    1926

  • $/SqFt

    $1,415

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

Home For Sale $995,000

Charming front exterior features lush landscaping, stone accents, and a two-car garage, perfect for curb appeal at 210 Laurel Park Ct, Winter Park, FL 32792
This cozy bedroom boasts hardwood floors, decorative rugs, and large windows letting in natural light at 210 Laurel Park Ct, Winter Park, FL 32792
This elegant bedroom boasts hardwood floors, decorative rugs, and large windows letting in natural light at 210 Laurel Park Ct, Winter Park, FL 32792
On Market For 34 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2838

  • Year Built

    2006

  • $/SqFt

    $351

One time capital contribution of $1,000 to HOA is required at closing. PR REAL ESTATE SERVICES.

Home For Sale $750,000

Picturesque pond featuring a fountain and ducks, with residential buildings in the background, all reflected in the water at 1312 Blue Stem Ln, Winter Park, FL 32792
Two-story gray home featuring a well-manicured lawn, a palm tree, and a brick driveway leading to the garage at 1312 Blue Stem Ln, Winter Park, FL 32792
Elegant front entrance featuring a decorative glass door, a brick pathway, and lush landscaping, creating a welcoming approach at 1312 Blue Stem Ln, Winter Park, FL 32792
On Market For 35 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2197

  • Year Built

    2022

  • $/SqFt

    $341

Don’t miss your chance to own a slice of paradise—schedule your private showing today and step into the luxurious city living you deserve! FORTUNE INTERNATIONAL REALTY.

Home For Sale $415,000

Reduced By $14,900

This home has a brick driveway, an attached garage, and a well manicured lawn with room to play at 3117 Shady Pine Ave, Winter Park, FL 32792
Fenced in back yard that is great for pets and play, and abuts to open grassy land at 3117 Shady Pine Ave, Winter Park, FL 32792
Side view of home showcasing crisp white exterior, black shutters, and well-maintained landscaping at 3117 Shady Pine Ave, Winter Park, FL 32792
On Market For 35 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1214

  • Year Built

    1983

  • $/SqFt

    $342

Coupled with efficient appliances, this home is designed to be eco-friendly while keeping utility costs low. EXP REALTY LLC.

Home For Sale $2,990,000

Beautiful two-story home featuring a manicured lawn, classic black shutters, and elegant architectural details at 1860 Via Contessa, Winter Park, FL 32789
Inviting living room with neutral sofas, stylish wood accent wall, and bright natural light at 1860 Via Contessa, Winter Park, FL 32789
Elegant dining room featuring a modern light fixture, wood accent wall, and seating for six at 1860 Via Contessa, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 37 Days
  • Bedrooms

    8

  • Full Bath(s)

    6

  • Sq. Ft.

    7000

  • Year Built

    2003

  • $/SqFt

    $427

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

Home For Sale $975,000

On Market For 38 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1045

  • Year Built

    1925

  • $/SqFt

    $933

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

Pended $599,999

Reduced By $8,001

Stylish front entrance with a wrought iron gate and a modern black brick accent wall at 7531 Lodge Pole Trl, Winter Park, FL 32792
Bright courtyard featuring skylights, a textured accent wall, and rock landscaping at 7531 Lodge Pole Trl, Winter Park, FL 32792
Inviting entrance with a wrought iron gate offering a view of the front yard at 7531 Lodge Pole Trl, Winter Park, FL 32792
On Market For 37 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2141

  • Year Built

    1972

  • $/SqFt

    $280

Don’t miss the opportunity to own this pristine, move-in-ready home—contact us today to schedule your private showing! NEXTDWELL.

Home For Sale $370,000

Charming single-story home with neutral paint and a mature, sprawling tree in the front yard at 3047 Riverbrook Dr, Winter Park, FL 32792
Charming single-story home with neutral paint, attached garage, and landscaped front yard at 3047 Riverbrook Dr, Winter Park, FL 32792
Close up front exterior shot of a charming home with a covered porch and landscaped front yard at 3047 Riverbrook Dr, Winter Park, FL 32792
On Market For 38 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1106

  • Year Built

    1973

  • $/SqFt

    $335

Don’t miss your chance to own this exceptional home in one of Winter Park’s most desirable neighborhoods! Schedule your showing today! KELLER WILLIAMS ADVANTAGE REAL.

Home For Sale $2,500,000

Stunning two-story home with a grand entrance, featuring a beautifully landscaped front yard and second story balcony at 450 Lakewood Dr, Winter Park, FL 32789
Enjoy outdoor living on this covered patio, with views of the pool and lush landscaping at 450 Lakewood Dr, Winter Park, FL 32789
Backyard pool with fountain and spa, complemented by the home's architecture at 450 Lakewood Dr, Winter Park, FL 32789
On Market For 38 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4676

  • Year Built

    2000

  • $/SqFt

    $535

Home has natural gas for the newer tankless water heater, pool heater, cooktop and the outdoor firepit. Roof new 2020. CHARLES RUTENBERG REALTY ORLANDO.

Pended $1,890,000

Well-manicured lawn and driveway leading up to the two-car garage of this two-story home at 2248 Middleton Ave, Winter Park, FL 32792
An elegant dining room featuring a modern chandelier, panelled wall and hardwood floors at 2248 Middleton Ave, Winter Park, FL 32792
A spacious living room, hardwood floors, and grand sliding doors to another space at 2248 Middleton Ave, Winter Park, FL 32792
On Market For 37 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3505

  • Year Built

    2025

  • $/SqFt

    $539

It’s the rare find that elevates your lifestyle in a way that’s simply unparalleled! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $729,000

Reduced By $20,000

Modern kitchen featuring white cabinets, granite countertops, stainless steel appliances, and stylish lighting at 2812 Mulford Ave, Winter Park, FL 32789
Contemporary kitchen with black appliances, granite countertops, white cabinets, and sleek modern lighting at 2812 Mulford Ave, Winter Park, FL 32789
Well-lit kitchen featuring stainless steel appliances, white cabinetry, granite counters and a dining area at 2812 Mulford Ave, Winter Park, FL 32789
On Market For 38 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1527

  • Year Built

    1953

  • $/SqFt

    $477

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

Home For Sale $489,900

Reduced By $35,100

Inviting single-Gathering home with a spacious driveway, mature trees, and manicured lawn at 7448 Grand Ct, Winter Park, FL 32792
Aerial view of a home with a backyard pool and patio area surrounded by trees at 7448 Grand Ct, Winter Park, FL 32792
Inviting backyard pool with blue tile accents and a spacious concrete deck at 7448 Grand Ct, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 38 Days
  • Bedrooms

    5

  • Full Bath(s)

    2

  • Sq. Ft.

    2158

  • Year Built

    1982

  • $/SqFt

    $227

OTHER FEATURES: new carpets, fresh paint, oversized lot (.25 acres), no backyard neighbor, on cul-de-sac, oversized driveway. KELLER WILLIAMS ADVANTAGE III.

Home For Sale $5,700,000

Beautiful two-story home with a landscaped front yard, manicured hedges and a paver driveway at 1660 Palmer Ave, Winter Park, FL 32789
An elegant two-story home is beautifully landscaped and includes planters and manicured gardens at 1660 Palmer Ave, Winter Park, FL 32789
A charming front entry boasts a covered porch with black lanterns and beautiful double doors at 1660 Palmer Ave, Winter Park, FL 32789
On Market For 39 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6406

  • Year Built

    2024

  • $/SqFt

    $890

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

Pended $2,495,000

Charming home with black and white striped awnings and a well manicured lawn at dusk at 140 Cortland Ave, Winter Park, FL 32789
Charming home with an American flag, striped awnings, and a brick walkway at 140 Cortland Ave, Winter Park, FL 32789
Bright entryway featuring hardwood floors, a staircase with white railing, and elegant decor at 140 Cortland Ave, Winter Park, FL 32789
On Market For 28 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    4168

  • Year Built

    1926

  • $/SqFt

    $599

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

Home For Sale $2,399,900

Reduced By $100,000

Lakeside home with a private boat dock, jet ski, and manicured lawn at 301 Rippling Ln, Winter Park, FL 32789
Beautiful backyard with a sparkling pool, outdoor seating, and lush green lawn at 301 Rippling Ln, Winter Park, FL 32789
Spacious tiled patio with folding glass doors, a pool, and comfortable outdoor seating at 301 Rippling Ln, Winter Park, FL 32789
On Market For 39 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3694

  • Year Built

    1958

  • $/SqFt

    $650

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

Home For Sale $899,000

Reduced By $26,000

Inviting light blue home features a curved driveway, well-kept landscaping, and mid-century modern architectural details at 625 Worthington Dr, Winter Park, FL 32789
A cozy light blue home showcasing a welcoming front porch with white chairs and mid-century modern decorative elements at 625 Worthington Dr, Winter Park, FL 32789
Charming front porch featuring comfortable seating, a decorative front door, and stylish accents at 625 Worthington Dr, Winter Park, FL 32789
On Market For 38 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2133

  • Year Built

    1958

  • $/SqFt

    $421

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

Home For Sale $619,999

Backyard features a refreshing pool, brick patio, spa, and comfortable seating at 701 Denton Rd, Winter Park, FL 32792
Beautiful backyard pool with a spa, patio, grill, and outdoor seating area at 701 Denton Rd, Winter Park, FL 32792
Elegant dining room featuring natural light, stylish chandelier, and tile flooring at 701 Denton Rd, Winter Park, FL 32792
On Market For 31 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2268

  • Year Built

    1961

  • $/SqFt

    $273

Centrally located in sought-after schools and provides convenient access to Downtown Winter Park, Rollins College, Downtown Orlando, UCF, & MCO. Come enjoy Winter Park living! ATRIUM REALTY, LLC.

Pended $545,000

Reduced By $5,000

Beautiful single-story home with well-kept landscaping, a two car garage, and a bright blue front door at 4200 Bear Gully Rd, Winter Park, FL 32792
Inviting single-story home with lush landscaping, a two-car garage, and blue door under a colorful sky at 4200 Bear Gully Rd, Winter Park, FL 32792
Spacious dining room features hardwood floors, a modern light fixture, and a large dining table at 4200 Bear Gully Rd, Winter Park, FL 32792
On Market For 38 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1945

  • Year Built

    2003

  • $/SqFt

    $280

Not often does a home in this area on this size lot come available, so schedule your showing now before it's too late. RED BIRD REALTY OF FLORIDA INC.

Pended $394,900

Reduced By $14,100

Single-story home with a well-maintained lawn and a driveway leading to the garage at 6901 Jackman Blvd, Winter Park, FL 32792
Inviting front porch of a cozy home, enhanced by lush landscaping and a neat lawn at 6901 Jackman Blvd, Winter Park, FL 32792
Comfortable living room with hardwood floors, large windows, and stylish furnishings at 6901 Jackman Blvd, Winter Park, FL 32792
On Market For 38 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1196

  • Year Built

    1978

  • $/SqFt

    $330

This home offers both comfort and space in an established and peaceful neighborhood. REDFIN CORPORATION.

Home For Sale $1,275,000

Modern home with white exterior, complemented by a brick driveway and manicured landscaping at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
Aerial view of a modern white home near a golf course with mature landscaping at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
Bright open-concept living room with modern furnishings flowing into a stylish kitchen at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 40 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2284

  • Year Built

    2015

  • $/SqFt

    $558

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

Home For Sale $750,000

Aerial view of modern home adjacent to a lush golf course and featuring ample parking at 726 N Pennsylvania Ave, Winter Park, FL 32789
Modern kitchen featuring stainless steel appliances, a black marble backsplash and a stylish breakfast bar at 726 N Pennsylvania Ave, Winter Park, FL 32789
Contemporary kitchen with stainless steel appliances, sleek black cabinetry and tiled flooring at 726 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 40 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1167

  • Year Built

    2015

  • $/SqFt

    $643

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

Home For Sale $550,000

A scenic aerial view of a modern home with a golf course, railroad, and lush greenery in the neighborhood at 720 N Pennsylvania Ave, Winter Park, FL 32789
Open-concept living room with modern furniture, a ceiling fan, and an open view into the modern kitchen at 720 N Pennsylvania Ave, Winter Park, FL 32789
Bright living room with wood-look tile flooring, neutral sofa, pops of color, and contemporary decor at 720 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 40 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1115

  • Year Built

    2015

  • $/SqFt

    $493

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

Pended $539,990

Reduced By $10,010

A bright and inviting blue home, showcasing a large covered porch and outdoor features at 423 Ololu Dr, Winter Park, FL 32789
A bright entryway features wood-look tile flooring, fresh paint and modern light fixture at 423 Ololu Dr, Winter Park, FL 32789
Modern kitchen featuring quartz countertops, new stainless steel appliances, and stylish pendant lighting at 423 Ololu Dr, Winter Park, FL 32789
On Market For 40 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1920

  • Year Built

    1981

  • $/SqFt

    $281

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

Home For Sale $1,350,000

Inviting front porch featuring a stylish door, sleek black shutters and a cozy seating area at 181 N Phelps Ave, Winter Park, FL 32789
Aerial view of a home featuring a long rectangular pool and mature landscaping at 181 N Phelps Ave, Winter Park, FL 32789
Backyard pool area with cabana, dining table, and lush greenery at 181 N Phelps Ave, Winter Park, FL 32789
On Market For 41 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3000

  • Year Built

    1948

  • $/SqFt

    $450

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

Home For Sale $749,000

An aerial view showcases the home's location near a road and the surrounding neighborhood at 5150 Old Howell Branch Rd, Winter Park, FL 32792
Charming single-story brick home featuring an attached garage and well-maintained lawn at 5150 Old Howell Branch Rd, Winter Park, FL 32792
A bright, modern living room with stylish furniture, sleek flooring, and neutral decor at 5150 Old Howell Branch Rd, Winter Park, FL 32792
On Market For 41 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    2108

  • Year Built

    1964

  • $/SqFt

    $355

This property is perfect for businesses seeking high visibility and accessibility, with excellent potential for various uses and expansion. COMPASS FLORIDA, LLC.

Home For Sale $1,675,000

Waterfront homes featuring private docks and pools, situated on a picturesque lake at 607 Ellen Dr, Winter Park, FL 32789
Scenic lake view featuring a private dock and residents paddle boarding at 607 Ellen Dr, Winter Park, FL 32789
Elegant two-story house boasting contemporary design with a flat roof and vibrant landscaping at 607 Ellen Dr, Winter Park, FL 32789
On Market For 44 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2812

  • Year Built

    2025

  • $/SqFt

    $596

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

Home For Sale $1,295,000

Aerial view of the home showcasing its gray roof, backyard space, and proximity to surrounding neighborhood at 1611 Chestnut Ave, Winter Park, FL 32789
Property highlighted by boundary lines showing its location and surrounding homes and well-manicured lawns at 1611 Chestnut Ave, Winter Park, FL 32789
Overhead image of a neighborhood featuring well-maintained homes, private pools, and mature landscaping at 1611 Chestnut Ave, Winter Park, FL 32789
On Market For 44 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2916

  • Year Built

    1973

  • $/SqFt

    $444

According to the owner backyard can accommodate a POOL! PARK AVENUE REALTY LLC.

Home For Sale $435,000

Reduced By $14,990

Charming single-story home with a two-car garage and a well-maintained front yard at 7427 Houston E Ct, Winter Park, FL 32792
Charming single-story home with a two-car garage and a well-maintained front yard at 7427 Houston E Ct, Winter Park, FL 32792
Inviting front entry with decorative door, adjacent window, and clean landscaping at 7427 Houston E Ct, Winter Park, FL 32792
On Market For 44 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1326

  • Year Built

    1971

  • $/SqFt

    $328

Schedule your visit today and come see why this should be your next home. FUTURE HOME REALTY INC.

Pended $1,595,000

Charming pink home featuring stately white columns, a landscaped front yard, and tropical palm trees at 335 Beloit Ave, Winter Park, FL 32789
Detailed floor plan showcasing the layout of the home's rooms and dimensions at 335 Beloit Ave, Winter Park, FL 32789
Inviting foyer with tile floors, artwork, and a view into the living space at 335 Beloit Ave, Winter Park, FL 32789
On Market For 33 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2420

  • Year Built

    1978

  • $/SqFt

    $659

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

Home For Sale $1,195,000

Inviting single-story home with a brick driveway, lush lawn, and a charming terracotta-tiled roof at 1690 Oneco Ave, Winter Park, FL 32789
Beautiful single-story home featuring a well-manicured lawn, brick driveway, and a classic terracotta tile roof at 1690 Oneco Ave, Winter Park, FL 32789
Elegant foyer featuring arched entryways, a dark wood front door, neutral paint and travertine tile flooring at 1690 Oneco Ave, Winter Park, FL 32789
On Market For 45 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2703

  • Year Built

    1967

  • $/SqFt

    $442

NOTE: all interior walls recently painted neutral soft white... also, this home has accessible elemements to it, including a handicapped ramp in garage.... PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $795,000

Reduced By $24,000

Inviting home showcasing a brick driveway leading to an attached garage and landscaped front yard at 625 Brechin Dr, Winter Park, FL 32792
Close-up of the brick-paved entryway with decorative columns and trimmed hedges at 625 Brechin Dr, Winter Park, FL 32792
Bright and airy living room featuring hardwood floors and a doorway to another room at 625 Brechin Dr, Winter Park, FL 32792
On Market For 45 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1961

  • $/SqFt

    $435

Located in one of Winter Park’s most adored communities, residences of Kenilworth Shores are zoned for the highly desirable Brookshire Elementary/Glenridge Middle/Winter Park High school district and are just a few minutes away from the Park Avenue shopping and dining district, Rollins College, Advent Health, Baldwin Park, and more. KELLY PRICE & COMPANY LLC.

Home For Sale $764,900

Reduced By $30,100

Lovely single-story house with a white exterior, attached garage, and green grass at 1037 N Virginia Ave, Winter Park, FL 32789
Beautiful single-story home featuring a white exterior, covered porch, and well-manicured landscaping at 1037 N Virginia Ave, Winter Park, FL 32789
Inviting covered front porch with decorative iron supports and black front door at 1037 N Virginia Ave, Winter Park, FL 32789
On Market For 45 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1101

  • Year Built

    1960

  • $/SqFt

    $695

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

Home For Sale $469,900

Reduced By $10,100

Well-manicured lawn and lush landscaping surround this single story home with an attached garage at 5359 Lanyard Ct, Winter Park, FL 32792
Charming one-story home featuring a brick facade, well-maintained lawn, and a welcoming red front door at 5359 Lanyard Ct, Winter Park, FL 32792
Warm and inviting foyer with neutral tile flooring, red accent wall, and decorative touches at 5359 Lanyard Ct, Winter Park, FL 32792
On Market For 45 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1572

  • Year Built

    1973

  • $/SqFt

    $299

This home is a rare gem for first-time buyers or anyone looking for a stress-free, move-in-ready home. REDFIN CORPORATION.

Pended $425,000

Inviting front entrance with a quaint bench, lush landscaping, and vibrant blue exterior paint at 328 Lake Fair Ln, Winter Park, FL 32789
A close-up of the home's front door, featuring a dark finish and wood post accents at 328 Lake Fair Ln, Winter Park, FL 32789
Bright dining room with hardwood floors, modern fan, and view to adjacent rooms at 328 Lake Fair Ln, Winter Park, FL 32789
On Market For 45 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1485

  • Year Built

    1958

  • $/SqFt

    $286

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

Home For Sale $419,000

Reduced By $11,000

Bright, open-concept kitchen with white cabinets, stainless steel appliances, and a breakfast bar overlooking the living area at 7331 Blue Jacket W Pl, Winter Park, FL 32792
Open-concept living area with stylish flooring, modern lighting, and an abundance of natural light at 7331 Blue Jacket W Pl, Winter Park, FL 32792
Modern kitchen featuring stainless steel appliances, a sleek backsplash, and a breakfast bar with pendant lighting at 7331 Blue Jacket W Pl, Winter Park, FL 32792
On Market For 45 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1581

  • Year Built

    1970

  • $/SqFt

    $265

Don’t miss your chance to make this move-in ready gem your new home! NETWORTH REALTY OF ORLANDO, LLC.

Home For Sale $1,225,000

Reduced By $25,000

Inviting single-story home with lush landscaping, brick driveway, and a cozy front yard at 1585 Chestnut Ave, Winter Park, FL 32789
Attractive home showcasing neat landscaping, a gray garage door, and a clay tile roof at 1585 Chestnut Ave, Winter Park, FL 32789
Bright dining room featuring a ceiling fan, large windows, and unique tile flooring at 1585 Chestnut Ave, Winter Park, FL 32789
On Market For 44 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2220

  • Year Built

    1959

  • $/SqFt

    $552

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

Pended $499,900

A charming two-story home with a red brick facade, a two-car garage, and mature trees at 4309 Enright Ct, Winter Park, FL 32792
Inviting front porch leading to a well-maintained home with a classic brick accent wall at 4309 Enright Ct, Winter Park, FL 32792
Bright living room with a white brick fireplace, large windows, and hardwood floors at 4309 Enright Ct, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 44 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2204

  • Year Built

    1985

  • $/SqFt

    $227

Seize the opportunity to own this charming home and start creating unforgettable memories in a space that truly feels like yours. BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY.

Home For Sale $284,000

Reduced By $9,000

Bright living room with large arched window, neutral decor, and wood-look floors showcasing a comfortable and inviting space at 1727 Winter Green Blvd, Winter Park, FL 32792
Spacious living room with a large window, plenty of sunlight, and wood floors at 1727 Winter Green Blvd, Winter Park, FL 32792
Well-lit kitchen featuring granite countertops, stainless steel appliances, and white cabinetry at 1727 Winter Green Blvd, Winter Park, FL 32792
On Market For 47 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1187

  • Year Built

    1994

  • $/SqFt

    $239

Like what you hear? Come see it for yourself! OPENDOOR BROKERAGE LLC.

Home For Sale $2,395,000

Modern home showcases a two-car garage, gravel driveway, and lush, green landscaping at 2412 Chantilly Ave, Winter Park, FL 32789
Elegant entryway featuring a modern glass door, stone path, and stylish landscaping at 2412 Chantilly Ave, Winter Park, FL 32789
Bright foyer with hardwood floors and a modern glass door leading to the exterior at 2412 Chantilly Ave, Winter Park, FL 32789
On Market For 46 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4506

  • Year Built

    2024

  • $/SqFt

    $532

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

Home For Sale $690,000

A beautiful home with a brick driveway, two-car garage, and landscaped front yard is seen on a bright sunny day at 1219 Verdant Glade Pl, Winter Park, FL 32792
Inviting front entrance with a brick walkway, lush landscaping, and a welcoming covered porch at 1219 Verdant Glade Pl, Winter Park, FL 32792
Bright foyer featuring tile floors, staircase with iron railing, and an open doorway to the outside at 1219 Verdant Glade Pl, Winter Park, FL 32792
On Market For 48 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2002

  • Year Built

    2019

  • $/SqFt

    $345

Don't miss out on this exceptional Winter Park home offering luxury, convenience, and a serene setting. FORTUNE INTERNATIONAL REALTY.

Pended $2,200,000

Stately two-story home boasts a clay tile roof, lush landscaping, and a long, curved driveway at 1446 Berkshire Ave, Winter Park, FL 32789
Close up shows the home's architectural details and manicured landscaping with towering palms at 1446 Berkshire Ave, Winter Park, FL 32789
Charming facade features a secure gated entry, arched windows, and an attached two-car garage at 1446 Berkshire Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 49 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4612

  • Year Built

    1925

  • $/SqFt

    $477

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

Pended $425,000

Close up of the home's front door with brick flooring, white pillars and blue shutters on the front windows at 2642 Tierra Cir, Winter Park, FL 32792
Spacious living room with parquet floors, decorative chandelier, and large windows that provide ample natural light at 2642 Tierra Cir, Winter Park, FL 32792
Open-concept living area features parquet floors, a chandelier and a clear view into the adjacent kitchen space at 2642 Tierra Cir, Winter Park, FL 32792
On Market For 41 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1715

  • Year Built

    1969

  • $/SqFt

    $248

The home is in an excellent location, backing to Interlachen Country Club, near the Lakemont YMCA, and with easy access to downtown Winter Park and Maitland. FANNIE HILLMAN & ASSOCIATES.

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Call to Schedule a Showing

(407) 485-1814

(407) 485-1814