322 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $1,495,000

Backyard pool area perfect for relaxing, with outdoor seating and well-maintained landscaping, offering a private oasis at 1420 Palmer Ave, Winter Park, FL 32789
Bright foyer with hardwood floors, staircase, and an archway that leads to a dining area with stylish decor at 1420 Palmer Ave, Winter Park, FL 32789
Cozy living room featuring hardwood floors, large window, and an archway leading to the formal dining room at 1420 Palmer Ave, Winter Park, FL 32789
On Market For 2 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2953

  • Year Built

    2004

  • $/SqFt

    $506

Comstock Park - (Roof: 2019, HVAC 2017, Mini Splits (2) 2024, Electrical 2004, Plumbing 2004) KELLER WILLIAMS WINTER PARK.

Home For Sale $799,000

Inviting front entrance featuring a blue door, white columns, and a cozy seating area at 676 Dunblane Dr, Winter Park, FL 32792
Relaxing front porch with stylish seating, perfect for enjoying the outdoors at 676 Dunblane Dr, Winter Park, FL 32792
Bright white front door with decorative glass and classic hardware, offering a welcoming entry at 676 Dunblane Dr, Winter Park, FL 32792
On Market Today
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1962

  • $/SqFt

    $437

676 Dunblane Drive is a rare opportunity to own a well-located, move-in-ready home in one of Winter Park’s most established and sought-after neighborhoods. Book your private showing TODAY! BALDWIN PARK REALTY LLC.

Home For Sale $449,000

Lovely exterior view of single-story home, featuring a well-kept lawn and an attached two-car garage at 2312 Poinciana Rd, Winter Park, FL 32792
Lovely one-story home with a well-maintained lawn and mature tree at 2312 Poinciana Rd, Winter Park, FL 32792
Enclosed front entrance with an arched gateway, adorned with brick accents and decorative wall cutouts at 2312 Poinciana Rd, Winter Park, FL 32792
On Market Today
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1806

  • Year Built

    1972

  • $/SqFt

    $249

Winter Woods - Whether you're starting a new chapter or looking to settle into a welcoming neighborhood, this home has everything you need and more. KELLER WILLIAMS WINTER PARK.

Home For Sale $440,000

Bright kitchen with white cabinetry, modern appliances and quartz countertops at 5436 Tangerine Ave, Winter Park, FL 32792
Updated kitchen featuring white cabinetry, stainless steel appliances and subway tile backsplash at 5436 Tangerine Ave, Winter Park, FL 32792
Open kitchen layout with new appliances, quartz countertops and wood flooring at 5436 Tangerine Ave, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market Today
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1996

  • Year Built

    1977

  • $/SqFt

    $220

Wrenwood Heights - Meticulously maintained, tastefully updated, and move-in ready — schedule your private showing today! CALL IT CLOSED INTL REALTY.

Home For Sale $439,999

Inviting front entrance with a decorative door, potted plants, brick accents, and stylish house numbers at 2209 Fairglenn Way, Winter Park, FL 32792
Comfortable living room with tile floors, ample seating, large windows, and a decorative ceiling fan at 2209 Fairglenn Way, Winter Park, FL 32792
Bright living area with tile floors, ceiling fan, arched windows, and elegant furnishings at 2209 Fairglenn Way, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market Today
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2027

  • Year Built

    1986

  • $/SqFt

    $217

Don’t miss your chance to make this well-maintained home your own—schedule your showing today! HIVE REALTY LLC.

Home For Sale $4,175,000

Beautiful home featuring a lush green lawn, manicured landscaping, and modern architectural design at 1581 Forest Ave, Winter Park, FL 32789
Striking modern home featuring manicured landscaping, mature trees, and a covered front entrance at 1581 Forest Ave, Winter Park, FL 32789
Elegant foyer features black-and-white checkered floors, a dazzling chandelier, and grand staircase at 1581 Forest Ave, Winter Park, FL 32789
On Market For 3 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4683

  • Year Built

    1954

  • $/SqFt

    $892

(Don't miss the secret wine room!) BHHS FLORIDA REALTY.

Home For Sale $1,599,000

Charming exterior with lush green lawn, brick driveway, and meticulous landscaping at 1327 Bridgeport Dr, Winter Park, FL 32789
Beautiful backyard oasis with a sparkling pool, brick patio, and poolside seating at 1327 Bridgeport Dr, Winter Park, FL 32789
Inviting freeform pool area, surrounded by lush landscaping and serene privacy at 1327 Bridgeport Dr, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 2 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4181

  • Year Built

    1979

  • $/SqFt

    $382

Waterbridge - Move right in, everything has been done. RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $795,000

Well-maintained home featuring a spacious two-car garage and brick-paved driveway at 627 Darcey Dr, Winter Park, FL 32792
Inviting front porch with brick flooring, classic columns, and seating area at 627 Darcey Dr, Winter Park, FL 32792
Bright and airy living room with hardwood floors, large windows, and stylish decor at 627 Darcey Dr, Winter Park, FL 32792
On Market For 2 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2509

  • Year Built

    1967

  • $/SqFt

    $317

Brookshire Heights - Don’t miss the opportunity to own this move-in-ready gem in one of Winter Park’s most desirable neighborhoods! COLDWELL BANKER RESIDENTIAL RE.

Pended $675,000

Inviting single-story house with a well-kept front yard and ample parking space at 1511 Chestnut Ave, Winter Park, FL 32789
Welcoming front porch with a cozy seating area and an orange front door at 1511 Chestnut Ave, Winter Park, FL 32789
Charming front porch featuring tiled flooring, white columns, and a peaceful view at 1511 Chestnut Ave, Winter Park, FL 32789
On Market For 2 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1275

  • Year Built

    1960

  • $/SqFt

    $529

Lake Knowles Terrace - Don’t miss your chance to become part of the Winter Park lifestyle! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $569,000

Expansive backyard featuring lush green grass and a privacy fence, offering ample space for outdoor activities at 240 Cambridge Blvd, Winter Park, FL 32789
Aerial view of a property showcasing its location within a neighborhood and proximity to a serene lake at 240 Cambridge Blvd, Winter Park, FL 32789
Bright living room features neutral decor, two sofas, two windows, and a modern entertainment center at 240 Cambridge Blvd, Winter Park, FL 32789
On Market Today
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1630

  • Year Built

    1950

  • $/SqFt

    $349

Glencoe - Don’t miss this opportunity to own a move-in-ready gem in the heart of Winter Park. Schedule your private showing today! REAL BROKER, LLC.

Pended $530,000

Inviting home featuring a lush green lawn, mature trees, and a convenient driveway for easy access at 2525 Lafayette Ave, Winter Park, FL 32789
Beautifully landscaped front yard with a well-maintained lawn and easy street access at 2525 Lafayette Ave, Winter Park, FL 32789
Bright living room with beautiful wood floors, a large window, and ample natural light at 2525 Lafayette Ave, Winter Park, FL 32789
On Market For 1 Day
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    817

  • Year Built

    1956

  • $/SqFt

    $649

Winter Park Village - Value is in the land. Schedule your showing today! KELLER WILLIAMS WINTER PARK.

Home For Sale $518,000

Well-maintained home showcasing a clean driveway, two-car garage, and lush green lawn on a sunny day at 1360 Gladiolas Dr, Winter Park, FL 32792
Inviting entrance with stone accents, a modern door, and fresh landscaping, creating curb appeal at 1360 Gladiolas Dr, Winter Park, FL 32792
Open entryway featuring a modern door, stone accents, and a glimpse into the bright, inviting interior at 1360 Gladiolas Dr, Winter Park, FL 32792
On Market For 2 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2006

  • Year Built

    1981

  • $/SqFt

    $258

Garden Lake Estates - Located in a top-rated Seminole County school district, this move-in-ready home offers the perfect blend of comfort, and functionality. A true lifestyle upgrade! VISTA HOMES REALTY LLC.

Home For Sale $499,000

Inviting single-story home with white trim, lovely landscaping, and a sunny front yard at 2835 Bongart Rd, Winter Park, FL 32792
A well-maintained home featuring a side entry garage, lush lawn, and manicured landscaping at 2835 Bongart Rd, Winter Park, FL 32792
Aerial shot of a home showcasing a spacious backyard and proximity to nearby pools at 2835 Bongart Rd, Winter Park, FL 32792
On Market For 2 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1880

  • Year Built

    1961

  • $/SqFt

    $265

Winter Park Estates - Don't miss this rare opportunity to own a completely turn-key home in a highly sought-after location with modern finishes and quality craftsmanship. Schedule your private tour today! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $435,000

Traditional style home with an attached garage and well-manicured front yard showcasing curb appeal at 5575 Garden Grove Cir, Winter Park, FL 32792
Bright dining area featuring a modern light fixture and sliding glass doors leading to the outdoors at 5575 Garden Grove Cir, Winter Park, FL 32792
Open-concept dining space with a wooden table adjacent to a kitchen and fireplace at 5575 Garden Grove Cir, Winter Park, FL 32792
On Market For 2 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1414

  • Year Built

    1985

  • $/SqFt

    $308

Garden Grove - Don’t miss the opportunity to make this charming home your own—schedule your private showing today! BENCHMARK REAL ESTATE GRP INC.

Home For Sale $425,000

Well-maintained gray home showcasing a bright yellow front door and lush landscaping at 3443 Arnel Dr, Winter Park, FL 32792
One-story home with an attached garage and a curved driveway, nestled in a well-landscaped front yard at 3443 Arnel Dr, Winter Park, FL 32792
Inviting one-story home with lush front yard landscaping and convenient attached garage at 3443 Arnel Dr, Winter Park, FL 32792
On Market For 2 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1503

  • Year Built

    1967

  • $/SqFt

    $283

Schedule your showing today and don't forget to ask for the full updates list! KELLER WILLIAMS WINTER PARK.

Home For Sale $399,990

Well-maintained single story home with a lush green lawn, complimented by mature trees, shrubbery, and a convenient circular driveway at 1017 Manchester Cir, Winter Park, FL 32792
Inviting single-story home with a two-car garage, lush landscaping, and a long circular driveway, offering curb appeal and convenience at 1017 Manchester Cir, Winter Park, FL 32792
Beautiful single-story home featuring an attached two-car garage, well-kept lawn, and a long driveway, blending comfort and charm at 1017 Manchester Cir, Winter Park, FL 32792
On Market For 4 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1704

  • Year Built

    1974

  • $/SqFt

    $235

Don’t miss out on this incredible opportunity to own a piece of Winter Park paradise! Schedule your showing today! FOWLKES REALTY CO.

Home For Sale $8,500,000

A stately home featuring a circular driveway, manicured landscaping, and symmetrical design elements at 1112 Preserve Point Dr, Winter Park, FL 32789
Elegant exterior of a home with landscaped grounds, featuring a circular driveway and beautiful architectural lighting at 1112 Preserve Point Dr, Winter Park, FL 32789
View of an elegant home, framed by mature trees, with a large circular driveway and landscaped entrance at 1112 Preserve Point Dr, Winter Park, FL 32789
On Market For 4 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6502

  • Year Built

    2013

  • $/SqFt

    $1,307

Windsong Preserve Point - Showings are by appointment only for qualified buyers. KELLY PRICE & COMPANY LLC.

Home For Sale $949,000

On Market For 4 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1314

  • Year Built

    1949

  • $/SqFt

    $722

Charmont - Seller is related to listing broker. RAZZANI INTERNATIONAL REALTY.

Home For Sale $435,000

Reduced By $15,000

A lovely private in-ground swimming pool with a screened-in lanai for outdoor enjoyment at 5547 Garden Grove Cir, Winter Park, FL 32792
Backyard view of the swimming pool and screened-in lanai of this single Gathering home at 5547 Garden Grove Cir, Winter Park, FL 32792
A pristine backyard showcasing a swimming pool, screened-in patio, and green grass at 5547 Garden Grove Cir, Winter Park, FL 32792
On Market For 4 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1517

  • Year Built

    1986

  • $/SqFt

    $287

Recent Updates Include: Roof replaced (2015) HVAC replaced (2021) Water heater (2016) Garage Door (2021) Attic insulation, A/C duct work. ROYALTY R E BOUTIQUE INC.

Pended $349,900

Enclosed backyard pool with deck, offering a private oasis for relaxation and recreation at 1670 Clematis Ln, Winter Park, FL 32792
Enclosed lanai with patio furniture, perfect for enjoying the outdoors in comfort and style at 1670 Clematis Ln, Winter Park, FL 32792
Spacious backyard with mature trees, and an enclosed pool ideal for outdoor enjoyment at 1670 Clematis Ln, Winter Park, FL 32792
On Market For 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1401

  • Year Built

    1962

  • $/SqFt

    $250

Eastbrook - This property offers huge potential whether you're looking to invest, flip, or make it your dream home. Schedule your showing today! KELLER WILLIAMS WINTER PARK.

Home For Sale $1,899,000

Inviting two-story home featuring manicured landscaping and stone walkway to front door, with a second story balcony at 1665 Temple Dr, Winter Park, FL 32789
Beautiful two-story home features lush landscaping, paver driveway, wood garage door covered by greenery, and balcony at 1665 Temple Dr, Winter Park, FL 32789
Paver driveway leading to garage featuring mature landscaping and charming vines climbing the front entrance at 1665 Temple Dr, Winter Park, FL 32789
On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3830

  • Year Built

    2007

  • $/SqFt

    $496

Woodmere Terrace - Don’t miss your chance to own a home that offers exceptional space, stylish design, and one of the most desirable locations in Winter Park. COMPASS FLORIDA LLC.

Home For Sale $1,250,000

Exterior of a tan home showing the yard with green grass, driveway, and manicured bushes at 4052 Gilder Rose Pl, Winter Park, FL 32792
Spacious kitchen featuring an island with a cooktop, stainless steel appliances, and tile flooring at 4052 Gilder Rose Pl, Winter Park, FL 32792
Expansive kitchen with a large island, bar seating, light wood cabinetry, and tile flooring at 4052 Gilder Rose Pl, Winter Park, FL 32792
On Market For 8 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4015

  • Year Built

    1995

  • $/SqFt

    $311

Call for your private tour today! HOMEVEST REALTY.

Pended $645,000

View of a well-maintained home with a brick driveway and lush landscaping, including mature trees and manicured hedges at 1773 Walnut Ave, Winter Park, FL 32789
Single-story home with dual entrances, brick driveway, and mature trees, blending comfort and curb appeal at 1773 Walnut Ave, Winter Park, FL 32789
Attractive home with mature shade tree, manicured hedges, and brick driveway creating a welcoming curb appeal at 1773 Walnut Ave, Winter Park, FL 32789
On Market For 7 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2146

  • Year Built

    1957

  • $/SqFt

    $301

Conwill Estates - This property is being sold as a teardown. CORCORAN PREMIER REALTY.

Home For Sale $579,900

Inviting single-story home with stone accents, green lawn, and mature trees, offering great curb appeal at 7679 Bent Bow Trl, Winter Park, FL 32792
Covered carport featuring stone accent wall, updated lighting, and access to the main residence at 7679 Bent Bow Trl, Winter Park, FL 32792
Enclosed carport with white walls and a decorative stone accent wall at 7679 Bent Bow Trl, Winter Park, FL 32792
On Market For 7 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2616

  • Year Built

    1971

  • $/SqFt

    $222

Call today for a private showing. GILKEY REAL ESTATE.

Home For Sale $2,349,000

Two-story home featuring a terracotta roof, arched windows with flower boxes and mature shade trees at 1361 Palmer Ave., Winter Park, FL 32789
Circular driveway featuring a brick paver design and lush landscaping providing privacy at 1361 Palmer Ave., Winter Park, FL 32789
Spacious living room with polished floors, pillars, and sliding glass doors leading to the outdoor pool at 1361 Palmer Ave., Winter Park, FL 32789
On Market For 10 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3558

  • Year Built

    2005

  • $/SqFt

    $660

Temple Heights - Ideally in the Winter Park school district and just minutes from Phelps Park, Park Avenue, Interlachen Country Club, Winter Park Racquet Club and Rollins College, this home presents an unparalleled opportunity to enjoy refined living in one of Central Florida’s desirable communities. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $475,000

Open-concept living room featuring hardwood floors, neutral paint, and arched doorways leading to other rooms at 3304 Bennington Ct, Winter Park, FL 32792
Bright living room with hardwood floors and sliding glass doors leading to the outdoor patio at 3304 Bennington Ct, Winter Park, FL 32792
Spacious living room featuring hardwood floors, neutral paint, and an open layout at 3304 Bennington Ct, Winter Park, FL 32792
On Market For 9 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1804

  • Year Built

    2003

  • $/SqFt

    $263

You won’t want to miss it! DAHLIA REALTY GROUP.

Home For Sale $449,000

Bright living room showcasing new floors, fresh paint, and lots of natural light at 1842 Puritan Ave, Winter Park, FL 32792
Open-concept living room with a modern design and updated kitchen appliances at 1842 Puritan Ave, Winter Park, FL 32792
Modern kitchen with stainless steel appliances, white cabinets, and a stylish backsplash at 1842 Puritan Ave, Winter Park, FL 32792
On Market For 8 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1836

  • Year Built

    1963

  • $/SqFt

    $245

Eastbrook - Don’t miss this opportunity to own a fully updated home that combines comfort, quality, and convenience in one of Central Florida’s most sought-after communities. COMPASS FLORIDA LLC.

Pended $379,900

Corner lot featuring a well-kept lawn and a charming single-story home at 3121 Thistlehill Drive, Winter Park, FL 32792
Beautiful home with a well-maintained lawn, mature trees, and a two-car garage at 3121 Thistlehill Drive, Winter Park, FL 32792
Close-up of a charming home's entry with brick accents and a secure gate at 3121 Thistlehill Drive, Winter Park, FL 32792
On Market For 10 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1503

  • Year Built

    1967

  • $/SqFt

    $253

Now it’s your turn to come in and make some new memories. Great deal! EXP REALTY LLC.

Home For Sale $710,000

Charming two-story home featuring a tile roof, neutral stucco exterior, and a brick paver driveway at 1147 Wildmeadow Run, Winter Park, FL 32792
Welcoming front porch featuring decorative sign, seating, and a charming front door with floral wreath at 1147 Wildmeadow Run, Winter Park, FL 32792
Bright entryway features wood-look floors, staircase with metal railing, and view of the dining and kitchen at 1147 Wildmeadow Run, Winter Park, FL 32792
On Market For 10 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2002

  • Year Built

    2020

  • $/SqFt

    $355

Meadows At Hawks Crest - The HOA fee includes lawn care and irrigation for the best of maintenance free living. HONEST REAL ESTATE COMPANY.

Home For Sale $369,900

Picturesque backyard view featuring lush green grass and mature trees along a tranquil stream at 1748 Harvest Cv, Winter Park, FL 32792
Relaxing screened-in patio with a dining table, chairs, and potted plants for outdoor enjoyment at 1748 Harvest Cv, Winter Park, FL 32792
Inviting screened-in patio with dining area and view of the backyard at 1748 Harvest Cv, Winter Park, FL 32792
On Market For 9 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1368

  • Year Built

    1987

  • $/SqFt

    $270

Autumn Glen - With great bones, a prime location, and a price that leaves room for updates, this one is a smart buy in a neighborhood that rarely has homes available. EXP REALTY LLC.

Home For Sale $2,455,000

Charming home at dusk with meticulously maintained landscaping and inviting curb appeal at 521 S Phelps Ave, Winter Park, FL 32789
Elegant home with a paver driveway, lush lawn, and a side-entry garage at twilight at 521 S Phelps Ave, Winter Park, FL 32789
Bright hallway with hardwood floors, staircase, and custom built-in storage at 521 S Phelps Ave, Winter Park, FL 32789
On Market For 11 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3883

  • Year Built

    2015

  • $/SqFt

    $632

Kenilworth Shores - This property brilliantly integrates cosmopolitan living while retaining the warmth of home at every corner. LA ROSA REALTY HORIZONS LLC.

Home For Sale $2,100,000

Charming single-story home with a mature landscaped front yard and red window shutters at 633 Balmoral Rd, Winter Park, FL 32789
Rear exterior view of home with brick patio and French doors leading to backyard at 633 Balmoral Rd, Winter Park, FL 32789
Screened-in porch with wood flooring and ceiling fans overlooking lake view at 633 Balmoral Rd, Winter Park, FL 32789
On Market For 12 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2674

  • Year Built

    1968

  • $/SqFt

    $785

Kenilworth Shores - Whether you renovate or start fresh, this opportunity is a rare chance to craft your own lakeside retreat in one of Winter Park's most desirable locations. Call today for details. COMPASS FLORIDA LLC.

Home For Sale $1,594,950

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
On Market For 11 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    3474

  • Year Built

    2008

  • $/SqFt

    $459

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 $450,000

An overhead view of a well-maintained property with lush landscaping, a screened-in patio, and a defined property line at 619 Byron Rd, Winter Park, FL 32792
Inviting living room with hardwood floors and neutral decor, featuring a large sofa and entertainment center at 619 Byron Rd, Winter Park, FL 32792
Well-lit kitchen featuring white cabinets and ample counter space, providing a clean and functional cooking area at 619 Byron Rd, Winter Park, FL 32792
On Market For 11 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1349

  • Year Built

    1957

  • $/SqFt

    $334

Eastgate - This move-in-ready gem in a highly sought-after neighborhood won’t last—schedule your showing today! RE/MAX 200 REALTY.

Home For Sale $430,000

Inviting single-Gathering home with a lush lawn and a classic design surrounded by trees and a white fence at 5210 Poinsetta Ave, Winter Park, FL 32792
Modern kitchen featuring gray cabinets, stainless steel appliances, and a black backsplash at 5210 Poinsetta Ave, Winter Park, FL 32792
Bright kitchen with stainless steel appliances, large island, and pendant lighting at 5210 Poinsetta Ave, Winter Park, FL 32792
On Market For 11 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1476

  • Year Built

    1974

  • $/SqFt

    $291

Wrenwood Heights - Discover your perfect Florida haven today! REAL BROKER, LLC.

Pended $398,000

Charming single-Gathering home with a well-manicured front yard, brick driveway, and an attached two-car garage at 2009 Nottingdale Ln, Winter Park, FL 32792
Charming single-Gathering home with a well-manicured front yard, brick driveway, and an attached two-car garage at 2009 Nottingdale Ln, Winter Park, FL 32792
Charming single-Gathering home with a well-manicured front yard, brick driveway, and an attached two-car garage at 2009 Nottingdale Ln, Winter Park, FL 32792
On Market For 7 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1582

  • Year Built

    1980

  • $/SqFt

    $252

Cedar Ridge - This home has great bones and needs some TLC. OLDE TOWN BROKERS INC.

Home For Sale $2,590,000

Elegant living room features a fireplace, stylish decor, and comfortable seating at 185 Sylvan Blvd, Winter Park, FL 32789
Spacious kitchen with modern appliances, an island with seating, and hardwood floors at 185 Sylvan Blvd, Winter Park, FL 32789
Inviting bedroom with large windows, a comfortable bed, and stylish decor at 185 Sylvan Blvd, Winter Park, FL 32789
On Market For 12 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

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 12 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

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 13 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.

Home For Sale $599,000

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 13 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 $1,699,000

Reduced By $50,000

Aerial view of a neighborhood showcasing tree-lined streets and proximity to a lake and parks at 2339 Lafayette Ave, Winter Park, FL 32789
Stunning two-story home with black shutters, a lovely lawn, and well manicured landscaping at 2339 Lafayette Ave, Winter Park, FL 32789
Charming two-story home featuring a well-manicured lawn, landscaping, and a quaint porch at 2339 Lafayette Ave, Winter Park, FL 32789
On Market For 15 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3379

  • Year Built

    2005

  • $/SqFt

    $503

Fontainebleau - All measurements are approximate and Buyer is responsible to verify dimensions. COLLADO REAL ESTATE.

Home For Sale $625,000

Bright living room with tile flooring, stylish furnishings, and modern decor, ideal for relaxing or entertaining at 2524 Sweetwater Trl, Winter Park, FL 32789
Open-concept living room featuring hardwood floors, neutral paint, and ample natural light, perfect for Gathering gatherings at 2524 Sweetwater Trl, Winter Park, FL 32789
Spacious living room offering hardwood floors and a billiard table to be enjoyed by Gathering and friends at 2524 Sweetwater Trl, Winter Park, FL 32789
On Market For 15 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1728

  • Year Built

    1965

  • $/SqFt

    $362

Extras include: 2 car garage, irrigation system with well, tile & laminate flooring throughout, NO HOA!, Fantastic neighborhood in a great location!! WELCOME HOME! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $510,000

Reduced By $10,000

Charming single-story home with a brick and stucco facade and a well-manicured front yard at 1742 Willa Cir, Winter Park, FL 32792
Bright living room with neutral decor, wood floors, ceiling fan and lots of natural light at 1742 Willa Cir, Winter Park, FL 32792
Inviting front porch with a decorative wood front door and large windows at 1742 Willa Cir, Winter Park, FL 32792
On Market For 14 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2313

  • Year Built

    1987

  • $/SqFt

    $220

This move-in-ready home combines comfort, convenience, and flexibility—an exceptional opportunity not to be missed. CENTURY 21 CARIOTI.

Home For Sale $299,995

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 16 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    818

  • Year Built

    1938

  • $/SqFt

    $367

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

Home For Sale $1,999,900

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 15 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 $1,200,000

Lush front entrance with tropical landscaping leads to a welcoming doorway at 4107 Gabriella Ln, Winter Park, FL 32792
Two-story home with wood deck, surrounded by lush greenery and mature trees in a secluded setting at 4107 Gabriella Ln, Winter Park, FL 32792
Beautiful screened-in pool with a rock waterfall and lush greenery, great for outdoor entertainment at 4107 Gabriella Ln, Winter Park, FL 32792
On Market For 17 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3074

  • Year Built

    1998

  • $/SqFt

    $390

Homes like this are rarely available—schedule your private showing today and experience the magic of Bear Gully Lake for yourself. KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $479,900

Reduced By $5,100

Beautiful in-ground swimming pool surrounded by lush landscaping and complemented by an outdoor pergola at 3054 Bluebrook Dr, Winter Park, FL 32792
The backyard features a screened-in porch and a pool deck that surrounds the in-ground pool at 3054 Bluebrook Dr, Winter Park, FL 32792
Enjoy outdoor cooking in this covered outdoor kitchen area, perfect for entertaining guests and Gathering at 3054 Bluebrook Dr, Winter Park, FL 32792
On Market For 16 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1939

  • Year Built

    1973

  • $/SqFt

    $247

Laurel Springs - Schedule your showing today and fall in love with your new forever home. ALORA REALTY GROUP INC.

Home For Sale $420,000

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 16 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1540

  • Year Built

    1956

  • $/SqFt

    $273

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

Pended $420,000

Inviting single-story home showcasing a well-manicured lawn and a convenient two-car garage at 1301 Paradise Ln, Winter Park, FL 32792
Expansive backyard featuring lush lawn, a screened patio and a classic wooden fence at 1301 Paradise Ln, Winter Park, FL 32792
Open-concept living room with modern furnishings, hardwood floors, and a view of the kitchen and backyard at 1301 Paradise Ln, Winter Park, FL 32792
On Market For 16 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1379

  • Year Built

    1984

  • $/SqFt

    $305

Never lived in since its complete overhaul, this is a one-of-a-kind opportunity to own a move-in ready home that delivers at every level. Book a private tour today. COMPASS FLORIDA LLC.

Home For Sale $399,000

Bright foyer features neutral tile flooring, a coat closet, and natural light at 2828 Whispering Way, Winter Park, FL 32792
Spacious living room with a brick fireplace, ceiling fan, and tile flooring at 2828 Whispering Way, Winter Park, FL 32792
Cozy living room features a brick fireplace, neutral walls, and sunlit windows at 2828 Whispering Way, Winter Park, FL 32792
On Market For 17 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1312

  • Year Built

    1986

  • $/SqFt

    $304

Easy access to 417, 436, and University. TOP VALUE PROPERTIES LLC.

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 386-801-4854 and speak with one of our real estate consultants.

EasyStreet

Call to Schedule a Showing

(386) 801-4854

(386) 801-4854