Winter Park Homes for Sale

Sort Option
  • _score
  • Price ↓
  • Newest Listings First
  • Square Footage ↓
  • Year Built ↓
Grid
List
Map

Lots And Land

HOWELL BRANCH, WINTER PARK, Florida 32792

1Picture(s)
7.13Acre
2 parcels located at Dodd Rd. and Howell Branch Rd. Winter Park, Fl Over 1 acre of redevelopment land with a future land use of OFFICE! Great location, high daily traffic, 2 parcels.
$1,800,000

Residential

3054 Bluebrook Drive, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
25Picture(s)
1,850Sqft
Lovingly immaculate home remodeled to perfection and strategically located in a beautiful family neighborhood in Winter Park! This home is conveniently located less than 15 minutes away from Downtown Orlando, University of Central Florida, Full Sail University, and Winter Park High School. It is the perfect modern home for any family with an open floor plan.
$359,000

Commercial

5541 HOWELL BRANCH ROAD, WINTER PARK, Florida 32792

10Picture(s)
3,768Sqft
3 story home with 5 bed and 3.5 baths and zoned for work/live to make this beautiful property your home AND office. The site can also be redeveloped and with an additional 6+ Acre of vacant land located right behind this site you can combine the lots and build almost any commercial building you'd like.
$974,000

Commercial

7608 ALOMA AVENUE, WINTER PARK, Florida 32792

5Picture(s)
0.52Acre
Great Daycare Center Opportunity. Freestanding Street Building with Brand New Daycare Center Build Out in progress. Delivery expected Q1 2021. Excellent Winter Park location on Aloma Avenue with affluent neighborhood and strong demographics.
$11,912

Single Family

5541 HOWELL BRANCH ROAD, WINTER PARK, Florida 32792

5Bedroom(s)
4Bathroom(s)
2Parking(s)
10Picture(s)
3,768Sqft
IMMEDIATE SALE!! Don't miss out on this one of a kind, 3 story home. This home is 5 bedroom, 3.5 bathroom homes zoned for a work/live so you can easily make this space your office as well! Current owners have business on first floor and live on second and third. This home features spacious rooms and plenty of room for entertaining.
$974,000

Single Family

4575 WHIMBREL PLACE, WINTER PARK, Florida 32792

5Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,284Sqft
Back on the market!! Owners wanted one more holiday season of memories before parting with their home of 35 years. This home provides a popular 5/2.5 three way split pool home with almost an acre of property on private, spring fed Bear Gully lake.
$925,000

Condominium

3014 Antique Oaks Circle, WINTER PARK, Florida 32792

1Bedroom(s)
1Bathroom(s)
18Picture(s)
749Sqft
Connect to all that the Orlando area offers from this Nicely Updated one-bedroom / 1-bath unit Available Now in Beautiful Parkview Village! The Gorgeous Kitchen with Granite Countertops and Cherry-stained Oak Cabinets highlights the roomy open floor plan. Recently New Appliances and plenty of room for a nice dining table and barstools at the counter! Large, Master Bedroom with walk-in closet.
$139,900

Single Family

3449 ARBUTUS LANE, WINTER PARK, Florida 32792

3Bedroom(s)
1Bathroom(s)
19Picture(s)
1,170Sqft
WINTER PARK HOME AT EASTBROOK COMMUNITY. COMPLETED RENOVATED HOME !!! NEW WATER HEATER, NEW LUXURY VINYL PLANKS FLOORING THROUGHOUT THE WHOLE HOUSE, NEWER A/C, NEW KITCHEN CABINETS WITH GRANITE COUNTER TOPS, NEW KITCHEN APPLIANCIES, AND RENOVATED BATH. FRESHLY PAINTED INSIDE AND OUTSIDE. NEW SCREEN IN THE BACK PORCH. LARGE SCREENED PATIO OVERLOOKS LARGE FENCED BACKYARD.
$269,900

Single Family

7748 WAUNATTA COURT, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
2,281Sqft
Lake Front on large, clear, spring fed Lake Waunatta. Bass fishing / water ski / jet ski. 3 Bed 2 Bath. Approx 3244 SF single story home. 2 year new roof. Ceramic tile throughout. Large master bedroom and bathroom with walk-in closet. Fire Place, sun room. Screen Patio off master bedroom. Outdoor deck, boat dock. Over sized large covered parking. Over 1/2 acre of land. Mature landscaping.
$624,000

Condominium

1000 S SEMORAN BOULEVARD, WINTER PARK, Florida 32792

2Bedroom(s)
2Bathroom(s)
13Picture(s)
1,049Sqft
2 Bedroom 2 Bath. cute apartment overlooking the community pool. back access to the unit. Close to UCF, Full Sale & Rollins . Close to downtown. Winter park public schools. close to shopping centers and malls. Laundry facility in the subdivision no in property Laundry but can be easily placed. Rent can be much more than what it was leased for . Great investment or for first time home buyers.
$132,000

Other

331 S PARK AVENUE, WINTER PARK, Florida 32789

13Picture(s)
1,184Sqft
Prime downtown Winter Park Retail for Sub-Lease. Three years remaining at current rate, with option to renew or negotiate future rent. This nearly 1,200 square foot space is the perfect size for your retail shop with plenty of walk-by traffic and amazing neighboring stores to compliment your business. Rate quoted includes all CAM, NNN, and parking fees.
$7,500

Single Family

1737 INDIANA AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
1Picture(s)
2,473Sqft
VALUE $$$ IS IN THE LAND! ...CURRENTLY SINGLE LOT 0.317 ACRE..PUBLIC SEWER AVAILABLE TO BE CONNECTED...UPON LOT SPLIT...TWO LOTS 0.15 ACRE EACH...THE CURRENT GUTTED RESIDENCE IS UN-LIVABLE...
$456,750

Lots And Land

1737 INDIANA AVENUE, WINTER PARK, Florida 32789

1Picture(s)
0.32Acre
VALUE $$$ IS IN THE LAND! ...CURRENTLY SINGLE LOT 0.317 ACRE..PUBLIC SEWER AVAILABLE TO BE CONNECTED...UPON LOT SPLIT...TWO LOTS 0.15 ACRE EACH...THE CURRENT GUTTED RESIDENCE IS UN-LIVABLE...
$456,750

Townhouse

1503 INDIANA AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,843Sqft
Brand new construction Winter Park townhome- turn key, lock and leave. Gorgeous light and bright 3 bed / 2.5 bath end unit is minutes from Hillstones, Trader Joes, Whole Foods and more. Convenient to Rollins College, Park Maitland, Lake Highland, Killarney Elementary and Advent Health. This open concept, 1843 sq. ft. townhome is flooded with natural light.
$512,000

Single Family

2255 CHANTILLY AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
1Parking(s)
25Picture(s)
3,158Sqft
Captivating and Traditional Southern Home in Winter Park! Situated on a sizeable 0.26+acre lot, this storybook 4BR/4BA abode captures attention with a muted buttercream exterior, bright white siding, and onyx black shutters. Subtle details in the architecture add warmth to this Floridian beauty, while the covered front porch and balcony add a touch of old-world charm and whimsy to the design.
$849,000

Single Family

1841 JESSICA COURT, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
2Parking(s)
5Picture(s)
1,646Sqft
Lovely 3 bedroom, 2 bath home in Winter Park’s highly-desirable Waterbridge Community. Tucked away on a quiet, tree-lined street this lovely tennis community sits in a central location putting you within minutes of Baldwin Park, Audubon Park, Park Avenue, and the Advent Health Winter Park Campus.
$575,000

Single Family

1470 PLACE PICARDY, WINTER PARK, Florida 32789

5Bedroom(s)
6Bathroom(s)
2Parking(s)
25Picture(s)
4,227Sqft
Welcome Home! Gorgeous traditional home featuring mother in law apartment is nestled next to the Vias in Olde Winter Park. Enjoy the tranquility of the front patio on a quiet, tree-lined, non-cut-through dead end street. Enter the beautiful front door from the Chicago brick front porch to a foyer which greets you with high ceilings and a view of the stunning pool through the rear French doors.
$1,600,000

Single Family

2218 FOSGATE DRIVE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
25Picture(s)
3,502Sqft
Pure potential in Winter Park. Large, 4 bedroom, 3.5 bath pool home with detached studio and full bath. Incredible location between downtown Winter Park and nearby Baldwin Park and Audubon Park. Zoned for the high-coveted Audubon K-8 school and Winter Park High. With a large, 3,500 +/- single-story layout this home has so much to offer.
$625,000

Single Family

2180 FORREST ROAD, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,605Sqft
Charming updated pool home situated on brick street on a beautiful corner lot in highly desirable Winter Park location. Great curb appeal with rocking chair front porch & swing. Separate formal living, dining & family rooms plus den.
$799,000

Single Family

1554 MINNESOTA AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
1Parking(s)
17Picture(s)
754Sqft
WINTER PARK BUNGALOW - 2 BEDROOMS 1 BATH - LARGE FENCED BACK YARD - FIXER UPPER WITH LOTS OF POTENTIAL! - Enjoy Everything Winter Park Has To Offer - Shopping - Restaurants - Farmer's Market - Golfing and Culture - Excellent Schools - 1 mile from Rollins College - Close to Central Florida Attractions and Major Highways.
$247,850

Single Family

2700 WRIGHT AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
5Bathroom(s)
2Parking(s)
23Picture(s)
2,692Sqft
Move-In Ready!! This Brand New 2021 Custom Home is ready for your family. Rex-Tibbs Construction has been building timeless homes in Winter Park for over 35 years. A guarantee of workmanship and professionalism can assure you that you have chosen the right house. This home’s exterior greets you with a covered entrance and metal roof to last years without worrying about replacement costs.
$1,175,000

Single Family

7909 PLEASANT PINE CIRCLE, WINTER PARK, Florida 32792

5Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,496Sqft
WELCOME TO YOUR FOREVER HOME - LOCATION! LOCATION!! THIS IS A MUST SEE HOME!!! THIS METICULOUSLY GORGEOUS HOME is situated in the HEART OF WINTER PARK in the ESTABLISHED GATED COMMUNITY of ENCLAVE AT ALOMA! TOP- RATED SEMINOLE COUNTY SCHOOLS and conveniently located close to everything and anything you could possibly n
$700,000

Single Family

8016 PLEASANT PINE CIRCLE, WINTER PARK, Florida 32792

4Bedroom(s)
3Bathroom(s)
2Parking(s)
20Picture(s)
2,319Sqft
Wonderful opportunity to own this exquisite 4 bedroom, 3 bath + bonus room home in the heart of Winter Park. Located in the gated community of Enclave at Aloma. This open floor plan home features fresh interior paint, tile throughout the main areas and brand new carpet in the bedrooms.
$469,999

Condominium

234 SCOTTSDALE SQUARE, WINTER PARK, Florida 32792

2Bedroom(s)
2Bathroom(s)
8Picture(s)
1,085Sqft
Great location with proximity to UCF, Full Sale, the airport, Winter Park schools, shopping, etc. Recently upgraded with kitchen backsplash, floors, and fresh paint throughout. Electrical box and plumbing have been updated. Downstairs half bath was converted to a full bath with marble. This particular unit features a wooden staircase that provides a very elegant feature.
$124,900

Single Family

1063 LUNDY COURT, WINTER PARK, Florida 32792

4Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,619Sqft
YOUR GAIN! Laminate floors, plantation shutters, stainless appliances, French doors, in-ground pool, covered patio, NEW ROOF, generous lot, fully fenced yard, and so much more await you in this 4 bedroom, 2 bathroom Winter Park home in an OPTIONAL HOMEOWNERS ASSOCIATION neighborhood.
$325,000

Condominium

186 SCOTTSDALE SQUARE, WINTER PARK, Florida 32792

2Bedroom(s)
2Bathroom(s)
18Picture(s)
1,020Sqft
This is a beautiful and well maintained 2 bedroom 2 bath condo just waiting for the right family to enjoy all of the amenities that it has to offer. Located close to Full Sail University. Freshly painted throughout and the kitchen sports stainless steel appliances with an open style.
$109,995

Single Family

1385 SAWGRASS COURT, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
2Parking(s)
24Picture(s)
2,011Sqft
This three bedroom, two bath home, ideally tucked away on a quiet cul-de-sac, sits on the edge of the Winter Park Pines Golf Course. The traditional layout includes formal dining and living rooms on either side of the large entry foyer, open kitchen & family room concept, and split bedroom plan.
$495,000

Condominium

3020 ANTIQUE OAKS CIRCLE, WINTER PARK, Florida 32792

2Bedroom(s)
2Bathroom(s)
17Picture(s)
1,018Sqft
This stunning condo features 2 spacious bedrooms and full bathrooms with all new flooring, with a lot of windows offering streams of natural light to enjoy with friends and family. Right next to Full Sail University, and minutes from Publix, Target, Fashion Square, and I-4 to easily navigate Central Florida.
$165,000

Single Family

2156 TALMAN COURT, WINTER PARK, Florida 32792

5Bedroom(s)
8Bathroom(s)
6Parking(s)
25Picture(s)
7,762Sqft
Rare opportunity to own a completely multi-generational home in the exclusive neighborhood of Talman Mews on DUAL lots. The statement entrance begins under the portico where you can welcome guests in the 2 story, oversized foyer and lovely sweeping staircase. A true Chef’s kitchen with custom cabinetry/appliances, gas range and Butler's pantry make entertaining easy.
$2,075,000

Townhouse

2504 GALLIANO CIRCLE, WINTER PARK, Florida 32792

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,550Sqft
One or more photo(s) has been virtually staged. This Winter Park two-story home offers a patio, granite countertops, and a one-car garage.
$262,000

Other

1201 LEWIS DRIVE, WINTER PARK, Florida 32789

10Picture(s)
788Sqft
Beautiful 2019 built office/retail space that was built out in 2020. Perfectly situated in sought after Winter Park. This space consisting of 788 sq ft is brand new with an open area, back private office, and separate bathroom and is the only built out retail in the building.
$2,093

Single Family

1441 PLACE VENDOME, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,305Sqft
A quiet, tree lined street leads you to this beautiful cottage style home in Winter Park! A neatly manicured front lawn and towering oak trees greet you as you walk up the driveway. Upon entering you’ll find the SPACIOUS living/kitchen/dining combination floor plan.
$849,900

Single Family

2219 VENETIAN WAY, WINTER PARK, Florida 32789

6Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
6,362Sqft
Beautifully designed and custom-built by premier Winter Park builder Bill Felkel, this stunning home is situated on an oversized 0.40 acre lot in the distinguished Winter Park Via’s. This spacious two-story estate has 6,362 sf of living space, and offers 6 bedrooms and 6 full bathrooms.
$2,550,000

Single Family

1016 MCKEAN CIRCLE, WINTER PARK, Florida 32789

4Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
3,443Sqft
This four-bedroom, four and one-half bath pool home is a unique opportunity with over one-half acre, in the heart of Winter Park, minutes walk to Park Avenue shops and dining, golf course, and Kraft Azalea Park. Secluded on quiet, highly sought-after McKean Circle, the large yard with mature landscaping offers complete privacy and park-like outdoor living.
$1,890,000

Lots And Land

315 VIRGINIA DRIVE, WINTER PARK, Florida 32789

12Picture(s)
1.22Acre
WINTER PARK CHAIN OF LAKES Construction ready 1.22 acre Lot...bring your own builder! Rarely Available Old Winter Park home site on pristine Lake Virginia with unspoiled views looking out towards the Nature Conservancy and Rollins College. Nestled among stately classic Florida homes and mature cypress, this desirable “.
$3,150,000

Single Family

1840 ANZLE AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
4Picture(s)
1,319Sqft
Located in the heart of Winter Park with close proximity to shopping, Winter Park hospital, and A rated schools. This 6,592 square foot lot is ready to build your dream home. Zoned Single Family R-1A, this parcel is priced as a stand-alone property. Other parcels available.
$309,500

Lots And Land

1840 ANZLE AVENUE, WINTER PARK, Florida 32789

4Picture(s)
0.15Acre
Located in the heart of Winter Park with close proximity to shopping, Winter Park hospital, and A rated schools. This 6,592 square foot lot is ready to build your dream home. Zoned Single Family R-1A, this parcel is priced as a stand-alone property. Other parcels available.
$309,500

Lots And Land

2005 SYCAMORE DRIVE, WINTER PARK, Florida 32789

8Picture(s)
0.19Sqft
Winter Park buildable lot - CLEARED and READY to build your dream home! Highly desired location minutes from everything Baldwin Park and Winter Park have to offer, just minutes to downtown and a quick ride to the beaches. Past Septic on site.
$575,000

Single Family

2912 MULFORD AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,830Sqft
LOCATION and gorgeous shady lot make this ranch-style Winter Park home the perfect spot for home sweet home.
$589,000

Condominium

102 S INTERLACHEN AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
1Parking(s)
25Picture(s)
901Sqft
Absolutely DELIGHTFUL & smartly renovated home in THE CLOISTERS!! Designer kitchen with quaint breakfast bar opens to light & bright great room with hardwood floors & crown molding leading to your serene balcony with beautiful views! Redesigned bath includes large shower, granite counters & a wee storage nook. Both bedrooms boast 2 closets & plantation shutters.
$425,000

Single Family

567 OSCEOLA AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,019Sqft
Award Winning, Winter Park Historic 4 Bed, 3-1/2 Bath Home meticulously restored to Perfection. With Features and Finishes that rival new homes in the area, it will not disappoint! Starting out front is the Brick Paver Circular Drive with Lush Landscaping, an expansive Wraparound Porch and Bowed Windows all adding to the Curb Appeal.
$932,000

Condominium

223 E CANTON AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,040Sqft
One or more photo(s) has been virtually staged. DOWNTOWN WINTER PARK CONDO - just steps from Park Avenue. This MODERN condo is located in Winterset, a SECURE building with access only by key or buzzer. This dramatic unit has been renovated from top to bottom with only the very best materials. Wide plank bamboo flooring, new baseboards and crown molding throughout.
$650,000

Single Family

1820 ANZLE AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,289Sqft
2016 LunDev beautiful modern farmhouse on a quiet street in Winter Park. Light, bright and open concept with great split-plan layout. Kitchen open to dining and gathering room areas with sliding doors overlooking private backyard.
$1,025,000

Single Family

1431 MAYFIELD AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
3Bathroom(s)
2Parking(s)
22Picture(s)
2,347Sqft
Sought after and desirable Winter Park. Minutes from Park Ave. This gorgeous 5 bedroom with den/home office, pool home floor plan offers the master suite down stairs. Updated flooring on the first level 4/2020. Upstairs guest bedroom offers a balcony.
$795,000

Townhouse

1281 MICHIGAN AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,866Sqft
Stunning new townhome community in the Heart of Winter Park! Multiple units available. Built by award-winning Osprey Custom Home Builders, this 3 bedroom, 2.5 bath home has been designated a Florida Green Certified Home and offers a highly-desirable, open-concept layout with designer finishes throughout.
$465,000

Townhouse

1269 MICHIGAN AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
10Picture(s)
1,866Sqft
Ready to move in!!! Winter Park's very best value in brand NEW quality construction, location and design. 12 townhomes by award winning Osprey Custom Homes. Convenient to Florida Hospital/Advent Health, Rollins College, Mills 50, College Park, just minutes to downtown Winter Park and Orlando and nearby shopping districts, services and restaurants.
$469,900

Single Family

433 LAKEVIEW AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,925Sqft
CHARMING WINTER PARK BUNGALOW! SPECTACULAR LAKE VIEWS! NO HOA! This is a rare opportunity to live in a serene residential enclave overlooking pristine Lake Killarney with brick streets and brilliant oak canopies. It is only a quick jaunt over to Hillstone, Glass Knife, Trader Joe’s, MLK Park, and the brand new Library and Events Center.
$625,000

Townhouse

1071 ARAGON AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
3Bathroom(s)
1Parking(s)
22Picture(s)
1,851Sqft
Conveniently located between downtown Winter Park and College Park with easy access to shopping, restaurants and highways. All the amenities one could want in this luxurious townhome. Tall ceilings and doorways throughout home. Custom tile floors on the first floor with a gas fireplace in the great room.
$475,000
86 Results returned.Per Page
Tony Johnson - Realtor - Greater Orlando FL Area Homes for Sale and Real Estate Listings