EasyStreet Realty
REALTOR ®
(386) 801-5417
Email Sherri
mobile navigation links
326 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $1,180,000

Charming two-story home features a manicured lawn, brick driveway, and inviting front porch with second-story balcony at 2607 Lafayette Ave, Winter Park, FL 32789
View Details 71 Photos
Charming two-story home features a manicured lawn, brick driveway, and inviting front porch with second-story balcony at 2607 Lafayette Ave, Winter Park, FL 32789
Charming two-story home features a manicured lawn, brick driveway, and inviting front porch with second-story balcony at 2607 Lafayette Ave, Winter Park, FL 32789
Charming two-story home features a manicured lawn, brick driveway, and inviting front porch with second-story balcony at 2607 Lafayette Ave, Winter Park, FL 32789
On Market Today

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2770

  • Year Built

    2018

  • $/SqFt

    $426

Winter Park Village - Located just minutes from Park Avenue’s shopping and dining, Rollins College, the Winter Park Chain of Lakes, and zoned for A-rated Dommerich Elementary, Maitland Middle, and Winter Park High School—this property blends luxury, location, and lifestyle. FORTUNE INTERNATIONAL REALTY.

Home For Sale $775,000

Charming single-story home featuring a uniquely landscaped front yard and a cozy front patio at 1840 Laurel Rd, Winter Park, FL 32789
View Details 33 Photos
Stunning front exterior with paver driveway, mature landscaping, and a pergola detail at 1840 Laurel Rd, Winter Park, FL 32789
Covered front porch with a decorative door, textured walls, and paver flooring at 1840 Laurel Rd, Winter Park, FL 32789
Cozy covered porch with unique plants, textured wall and convenient door access at 1840 Laurel Rd, Winter Park, FL 32789
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2245

  • Year Built

    1957

  • $/SqFt

    $345

Charmont - Don’t miss this rare opportunity to create something truly special in the heart of Olde Winter Park! KEYSEEKERS REAL ESTATE.

Home For Sale $675,000

Charming home featuring lush landscaping and mature trees in a serene front yard setting at 4030 Cool Water Ct, Winter Park, FL 32792
View Details 75 Photos
Attractive home exterior with a well-manicured lawn and mature trees providing ample shade at 4030 Cool Water Ct, Winter Park, FL 32792
Well-maintained home featuring a manicured lawn and mature trees shading the front of the house at 4030 Cool Water Ct, Winter Park, FL 32792
Lovely home with a well-kept lawn and shade trees highlighting the property's curb appeal at 4030 Cool Water Ct, Winter Park, FL 32792
On Market Today

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2910

  • Year Built

    1979

  • $/SqFt

    $232

Don’t miss this exceptional opportunity, schedule your private showing today! CREEGAN GROUP.

Home For Sale $1,300,000

Charming home with mature trees and well-manicured lawn at 171 Cortland Ave, Winter Park, FL 32789
View Details 23 Photos
Charming home with mature trees and well-manicured lawn at 171 Cortland Ave, Winter Park, FL 32789
Charming home with mature trees and well-manicured lawn at 171 Cortland Ave, Winter Park, FL 32789
Backyard with mature trees at 171 Cortland Ave, Winter Park, FL 32789
On Market For 2 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1683

  • Year Built

    1940

  • $/SqFt

    $772

Cortland Park - You will live just minutes away from top rated schools, healthcare, restaurants and shopping and just a few minutes' drive to boat ramp access to Winter Parks famous chain of lakes. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $779,000

Charming home featuring a well-manicured lawn and palm trees, offering a welcoming curb appeal at 103 Longhorn Rd, Winter Park, FL 32792
View Details 59 Photos
Inviting front porch with a white brick facade, plants, and a walkway, perfect for relaxing outdoors at 103 Longhorn Rd, Winter Park, FL 32792
Outdoor patio area featuring comfortable seating, a dining table, and a stylish design, perfect for entertaining at 103 Longhorn Rd, Winter Park, FL 32792
The exterior of a single story home with white paint, white framed windows and a grey roof at 103 Longhorn Rd, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 2 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3493

  • Year Built

    1969

  • $/SqFt

    $223

Call today to schedule your showing. KELLER WILLIAMS WINTER PARK.

Home For Sale $570,000

Charming single-story home featuring a well-manicured lawn and attached two-car garage at 3231 Lowndes Dr, Winter Park, FL 32792
View Details 3 Photos
Traditional brick home with a lush green lawn, mature trees, and a welcoming front porch at 3231 Lowndes Dr, Winter Park, FL 32792
Spacious backyard with lush green grass, stepping stones, and mature trees providing shade at 3231 Lowndes Dr, Winter Park, FL 32792
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1749

  • Year Built

    1965

  • $/SqFt

    $326

Georgetown Estates - Close to shopping and dining, excellent location with everything you need. LA ROSA REALTY KISSIMMEE.

Home For Sale $480,000

Charming single-story home featuring a solar panel roof, well-manicured lawn, and attached two-car garage at 2832 Buccaneer Dr, Winter Park, FL 32792
View Details 53 Photos
Aerial view of a beautiful home with a solar panel roof, screened-in pool, and fenced yard at 2832 Buccaneer Dr, Winter Park, FL 32792
Aerial view of a home with a screened pool, playground, solar panel roof, and a spacious backyard at 2832 Buccaneer Dr, Winter Park, FL 32792
Inviting single-story house with a gray roof, solar panels, two-car garage, and well-kept front yard at 2832 Buccaneer Dr, Winter Park, FL 32792
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1736

  • Year Built

    1984

  • $/SqFt

    $276

Come experience the lifestyle you’ve been waiting for! ORLANDO EXPERT REALTY LLC.

Home For Sale $399,900

Charming single-story home with a well-maintained lawn and landscaping, set under a partly cloudy sky at 7331 Blue Jacket W Pl, Winter Park, FL 32792
View Details 30 Photos
Spacious backyard featuring a screened lanai, partial fencing, and lush greenery, perfect for outdoor living at 7331 Blue Jacket W Pl, Winter Park, FL 32792
Modern kitchen with stainless steel appliances, white cabinetry, a stylish backsplash, and sleek gray flooring at 7331 Blue Jacket W Pl, Winter Park, FL 32792
Bright kitchen featuring stainless steel appliances, white cabinets, updated backsplash, and ample counter space at 7331 Blue Jacket W Pl, Winter Park, FL 32792
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1581

  • Year Built

    1970

  • $/SqFt

    $253

Woodcrest - Buyer responsible for their own due diligence. SAVVY AVENUE, LLC.

Home For Sale $299,000

Charming single-story home featuring a blue front door, lush greenery, and well-maintained lawn at 1979 Staunton Ave, Winter Park, FL 32789
View Details 21 Photos
Stunning aerial view of the property with lake access, surrounded by mature trees and neighboring homes at 1979 Staunton Ave, Winter Park, FL 32789
Spacious living room boasts wood floors, natural light, and neutral colors, offering a versatile space at 1979 Staunton Ave, Winter Park, FL 32789
Open living area featuring wood floors, a breakfast bar, white cabinets and stainless-steel appliances at 1979 Staunton Ave, Winter Park, FL 32789
On Market For 2 Days

  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    736

  • Year Built

    1948

  • $/SqFt

    $406

Karolina On Killarney - Do Not Submit Offers Site Unseen! CORBELO LLC.

Pended $497,500

Charming single-story home with lush landscaping and mature trees lining the front yard at 2817 Fitzooth Dr, Winter Park, FL 32792
View Details 26 Photos
Private backyard pool surrounded by a spacious patio and lush greenery for relaxation at 2817 Fitzooth Dr, Winter Park, FL 32792
Inviting backyard pool featuring a white concrete surround and verdant landscaping at 2817 Fitzooth Dr, Winter Park, FL 32792
Functional kitchen with stainless steel refrigerator, black dishwasher, and bright cabinetry at 2817 Fitzooth Dr, Winter Park, FL 32792
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1619

  • Year Built

    1965

  • $/SqFt

    $307

Pool equipment at the home, washer and dryer and 2nd refrigerator in garage is included. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $1,125,000

Stunning home with elegant architectural details, mature landscaping, and palm trees at 2880 Old Castle Dr, Winter Park, FL 32792
View Details 32 Photos
Gated entrance to the community with brick pillars, providing privacy and security at 2880 Old Castle Dr, Winter Park, FL 32792
Well-equipped kitchen with stainless steel appliances, granite countertops, and white cabinetry at 2880 Old Castle Dr, Winter Park, FL 32792
Spacious kitchen with granite countertops, double sinks, hardwood floors and stainless appliances at 2880 Old Castle Dr, Winter Park, FL 32792
On Market For 5 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3839

  • Year Built

    1993

  • $/SqFt

    $293

This is Florida living at its finest. CORCORAN PREMIER REALTY.

Pended $779,000

Charming home featuring an attached two-car garage, well-maintained landscaping, and mature palm trees at 1823 Sunset Dr, Winter Park, FL 32789
View Details 1 Photo
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2414

  • Year Built

    1940

  • $/SqFt

    $323

Call today for your private tour ! ! COMPASS FLORIDA LLC.

Home For Sale $1,495,000

Inviting two-story home featuring a well-manicured lawn, blue shutters and a paver driveway leading to a two-car garage at 1420 Palmer Ave, Winter Park, FL 32789
View Details 47 Photos
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
A beautiful backyard pool with a tranquil waterfall, lounge chairs, and lush landscaping against a colorful sunset backdrop 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
On Market For 7 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

Charming single-story home with a well-manicured lawn and inviting curb appeal under a gorgeous sunset sky at 676 Dunblane Dr, Winter Park, FL 32792
View Details 43 Photos
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 For 6 Days

  • 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

Charming single-story home boasts a well-manicured lawn, beautiful landscaping, and a welcoming front entrance at 2312 Poinciana Rd, Winter Park, FL 32792
View Details 36 Photos
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 For 6 Days

  • 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

Inviting front entry features double glass doors and colorful flower arrangement at 5436 Tangerine Ave, Winter Park, FL 32792
View Details 33 Photos
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 For 5 Days

  • 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

Charming single-story home with a well-manicured lawn, mature trees, and a two-car garage on a sunny day at 2209 Fairglenn Way, Winter Park, FL 32792
View Details 30 Photos
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 For 5 Days

  • 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

Stunning modern home with manicured lawn, dark trim, and lush landscaping at 1581 Forest Ave, Winter Park, FL 32789
View Details 45 Photos
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 8 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

Stunning aerial view of lakeside home, lush greenery, and inviting pool, making it perfect for relaxation at 1327 Bridgeport Dr, Winter Park, FL 32789
View Details 48 Photos
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 7 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

Charming single-story home with mature trees, lush lawn, and manicured shrubbery at 627 Darcey Dr, Winter Park, FL 32792
View Details 38 Photos
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 7 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

Charming single-story home featuring a quaint front porch, covered parking, and a well-maintained lawn at 1511 Chestnut Ave, Winter Park, FL 32789
View Details 25 Photos
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 7 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

Charming single-story home with a well-maintained lawn, beautiful pavers, and a striking blue double-door entrance at 240 Cambridge Blvd, Winter Park, FL 32789
View Details 23 Photos
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 For 7 Days

  • 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

Charming single-story home with a well-maintained lawn and mature trees offering curb appeal at 2525 Lafayette Ave, Winter Park, FL 32789
View Details 23 Photos
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 6 Days

  • 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

Charming single-story home with a manicured lawn, accented by stone details and solar panels on the roof at 1360 Gladiolas Dr, Winter Park, FL 32792
View Details 46 Photos
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 5 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

Charming single-story home with a well-manicured lawn and inviting front entrance at 2835 Bongart Rd, Winter Park, FL 32792
View Details 50 Photos
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 7 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 $425,000

Charming one-story home with a winding driveway, mature landscaping, and an attached garage at 3443 Arnel Dr, Winter Park, FL 32792
View Details 55 Photos
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 7 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 $420,000

Reduced By $15,000

Charming single-story home featuring a well-maintained lawn and mature trees providing ample shade at 5575 Garden Grove Cir, Winter Park, FL 32792
View Details 30 Photos
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 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1414

  • Year Built

    1985

  • $/SqFt

    $297

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 $399,990

Charming single-story home featuring a well-manicured lawn and a spacious driveway leading to an attached two-car garage at 1017 Manchester Cir, Winter Park, FL 32792
View Details 50 Photos
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 8 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

Breathtaking lakefront estate with lush landscaping and circular driveway, showcasing the home's elegance at 1112 Preserve Point Dr, Winter Park, FL 32789
View Details 88 Photos
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 8 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

Charming single-story home with a well-manicured lawn, lush landscaping, and a light blue front door at 251 Glenridge Way, Winter Park, FL 32789
View Details 1 Photo
On Market For 8 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

Charming single Gathering home featuring a well-manicured front yard and solar panels at 5547 Garden Grove Cir, Winter Park, FL 32792
View Details 28 Photos
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 8 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

Charming single-story home features a well-manicured front lawn, attached garage, and classic curb appeal at 1670 Clematis Ln, Winter Park, FL 32792
View Details 4 Photos
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 9 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

Charming two-story home features a lush landscaped yard, wood garage door covered by greenery, and second story balcony at 1665 Temple Dr, Winter Park, FL 32789
View Details 58 Photos
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 10 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

Beautiful two story home featuring a blue tiled roof, green lawn, and well maintained landscaping at 4052 Gilder Rose Pl, Winter Park, FL 32792
View Details 43 Photos
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 12 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

Charming single-story home featuring dual entryways, brick driveway, and mature tree providing ample shade at 1773 Walnut Ave, Winter Park, FL 32789
View Details 4 Photos
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 $559,900

Reduced By $20,000

Charming single-story home with stone facade, well-manicured lawn, mature trees, and a paved driveway at 7679 Bent Bow Trl, Winter Park, FL 32792
View Details 71 Photos
Charming single-story home featuring a well-maintained lawn and a two-car garage at 7679 Bent Bow Trl, Winter Park, FL 32792
Stone-clad front entrance featuring an open porch and a single-car garage at 7679 Bent Bow Trl, Winter Park, FL 32792
Covered entryway with stone accent wall, offering a sheltered welcome to the home at 7679 Bent Bow Trl, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2616

  • Year Built

    1971

  • $/SqFt

    $214

Call today for a private showing. GILKEY REAL ESTATE.

Home For Sale $2,349,000

Stately two-story home featuring a terracotta roof, arched windows with flower boxes and lush landscaping at 1361 Palmer Ave., Winter Park, FL 32789
View Details 43 Photos
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 14 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 $465,000

Reduced By $10,000

Charming single-story home with a well-manicured lawn, lush landscaping, and an attached two-car garage at 3304 Bennington Ct, Winter Park, FL 32792
View Details 32 Photos
Bright, open-concept living room featuring hardwood floors, modern decor and seamless flow into the kitchen at 3304 Bennington Ct, Winter Park, FL 32792
Open-concept living room boasts hardwood floors, neutral paint, and a seamless flow to the kitchen at 3304 Bennington Ct, Winter Park, FL 32792
Bright living room features sliding glass doors that open to a screened lanai with views of lush greenery at 3304 Bennington Ct, Winter Park, FL 32792
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1804

  • Year Built

    2003

  • $/SqFt

    $258

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

Home For Sale $449,000

Charming home featuring a covered porch, updated fixtures, and freshly painted exterior at 1842 Puritan Ave, Winter Park, FL 32792
View Details 24 Photos
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 13 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.

Home For Sale $379,900

Charming single-story home with well-manicured lawn and mature landscaping at 3121 Thistlehill Drive, Winter Park, FL 32792
View Details 29 Photos
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 7 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
View Details 38 Photos
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 14 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.

Pended $369,900

Charming single-Gathering home with a brick facade, attached garage and landscaped front yard at 1748 Harvest Cv, Winter Park, FL 32792
View Details 37 Photos
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 13 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

Stunning two-story white home featuring arched entry, front balcony, well-manicured landscaping and a wood-look garage door at 521 S Phelps Ave, Winter Park, FL 32789
View Details 34 Photos
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 15 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
View Details 25 Photos
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 16 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
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
On Market For 15 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

Charming single-story home with a manicured lawn, colorful flower beds, and an attached two-car garage at 619 Byron Rd, Winter Park, FL 32792
View Details 40 Photos
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 15 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

Charming single-story home featuring brick accents, a two-car garage, and a well-manicured lawn at 5210 Poinsetta Ave, Winter Park, FL 32792
View Details 41 Photos
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 15 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
View Details 42 Photos
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 12 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

Stunning two-story home with a modern design, beautiful landscaping, and a grand entrance at 185 Sylvan Blvd, Winter Park, FL 32789
View Details 8 Photos
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 16 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 55 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 16 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.

Viewing HOMES 1 to 50 of 326

Area Stats

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

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$499,118
$439,900
149
2.0%
55.7%
83

Apopka
$533,307
$483,490
570
1.6%
48.6%
86

Belle Isle
$855,518
$659,900
21
0.0%
42.9%
72

Casselberry
$426,023
$416,500
100
3.0%
57.0%
69

Celebration
$1,353,570
$1,072,500
44
0.0%
56.8%
95

Champions Gate
$703,031
$709,500
16
0.0%
50.0%
315

Chuluota
$819,415
$697,450
26
0.0%
50.0%
49

Clermont
$581,260
$487,990
723
0.7%
51.9%
79

Gotha
$1,179,300
$750,000
13
0.0%
61.5%
59

Groveland
$486,027
$400,000
276
1.1%
61.6%
85

Harmony
$431,786
$417,900
71
0.0%
40.8%
98

Kissimmee
$522,258
$445,000
2363
1.9%
50.8%
104

Longwood
$755,656
$555,000
217
1.4%
56.2%
73

Maitland
$1,015,604
$610,000
95
2.1%
53.7%
84

Minneola
$599,964
$548,480
141
0.7%
44.0%
81

Montverde
$1,577,035
$1,100,000
49
0.0%
44.9%
106

Ocoee
$533,155
$487,445
182
1.1%
48.4%
75

Orlando
$683,507
$499,997
3046
1.6%
51.0%
80

Oviedo
$711,071
$621,500
222
0.5%
52.3%
72

Poinciana
$324,649
$313,990
285
1.4%
52.6%
123

Reunion
$1,834,787
$1,069,900
105
2.9%
57.1%
169

Saint Cloud
$668,096
$513,363
46
4.3%
56.5%
283

Sanford
$529,869
$419,995
380
0.8%
49.7%
94

Sorrento
$608,889
$464,900
103
1.0%
53.4%
93

Windermere
$2,128,156
$1,295,000
277
0.0%
47.3%
102

Winter Garden
$873,972
$727,150
609
0.8%
48.8%
83

Winter Springs
$624,844
$494,400
153
0.7%
54.2%
71

EasyStreet

Call to Schedule a Showing

(386) 801-5417

(386) 801-5417