Winter Park Homes for Sale

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Single Family

3127 HEARTLEAF PL, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,913Sqft
Check out this beautiful move-in-ready 3 bedroom with office/den, 2 bath home located in the highly sought out subdivision of Lost Creek in Winter Park, Seminole County. Walking into the front door you will enter the living room with dark wood floors and soaring ceilings with a view to the back yard through the 4 French doors.
$375,000

Single Family

656 WORTHINGTON DRIVE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,970Sqft
Spacious, updated and immaculate 4/3.5 POOL Executive home with almost 3000 sq ft, is awaiting it’s new owner. Full of delightful entertaining space, office and an oversized 4th bedroom, on lower level, which makes a great bonus room, large private guest or teen suite with it’s own private full bathroom.
$850,000

Single Family

7143 GROVE AVENUE, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,495Sqft
Move in ready, 3 bedrooms, 2 bathrooms completely renovated home in great location. This beautiful house features an open concept kitchen with stainless steel appliances and a spacious island, ready to entertain and build amazing memories.
$399,900

Lots And Land

911 OSCEOLA AVENUE, WINTER PARK, Florida 32789

3Picture(s)
0.45Sqft
One of a kind lot in walking distance to Park Avenue, Alfond Inn and Rollins Collège. Come build the home of your dreams on this oversized lot, current home is immaculate so renovation and or addition opportunity.
$949,000

Single Family

1935 MAGNOLIA AVENUE, WINTER PARK, Florida 32792

2Bedroom(s)
1Bathroom(s)
1Parking(s)
13Picture(s)
1,024Sqft
Welcome to this charming Winter Park bungalow located on a quiet dead end street. LARGE 59 x 157 lot features new backyard wood fence & shed. Inside you will find 2 Bedroom/1 FULLY RENOVATED Bath + Family room that is currently furnished as a 3rd Bedroom & boasts a wall of windows overlooking yard.
$250,000

Single Family

861 MAYFIELD AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
4Parking(s)
25Picture(s)
3,373Sqft
Modern and spacious, this RARE Mid-Century Modern home, designed by Frank Sheehy is nestled amongst Alabama Oaks subdivision and just steps away from LAKE MAITLAND.
$999,900

Single Family

3449 ARBUTUS LANE, WINTER PARK, Florida 32792

3Bedroom(s)
1Bathroom(s)
24Picture(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

3130 HEARTWOOD AVENUE, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,627Sqft
Superb home in a great location with wonderful schools. This well priced home is on a tree shaded street in a well established area. This wonderful three Bedroom home is move in ready. Step into the living room and see the beautiful cedar paneling that is real wood, the flooring is exquisite wood look ceramic tile.
$330,000

Single Family

1323 HEAVENLY COVE, WINTER PARK, Florida 32792

4Bedroom(s)
3Bathroom(s)
4Parking(s)
25Picture(s)
2,654Sqft
Beautiful understated LUXURY tucked away in Winter Park in the small GATED community of Eden Point! Enjoy a WATER VIEW ~ CUSTOM IN GROUND SPA ~ OPEN & SPLIT FLOOR PLAN ~ 9’ CEILINGS ~ SURROUND SOUND SYSTEM & DESIGNER touches throughout! The brick paver driveway and impeccable landscaping invite you to come inside and imagine living every day in this gorgeous home.
$725,000

Single Family

901 OSCEOLA AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
2,469Sqft
Stunning Mid-Century flair meets Winter Park charm. This centrally located 3 bed, 2 bath plus office abode offers over 2,400 sq ft and sits on a large .31 acre lot within walking distance to Rollins College and Park Ave. Soaring ceilings in the light-filled foyer showcase large windows on either side and above the front door.
$829,000

Townhouse

607 WARRENTON ROAD, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
1Parking(s)
14Picture(s)
1,365Sqft
This cozy Townhouse is a great bargain for its neighborhood. It has just been fully remodeled with a repainted roof, new closets in master and guest rooms, new vanity in master room, brand new carpet in all bedrooms, stainless appliances in kitchen, etc.
$259,000

Single Family

429 S RANGER BOULEVARD, WINTER PARK, Florida 32792

4Bedroom(s)
2Bathroom(s)
2Parking(s)
24Picture(s)
1,652Sqft
This is the Home Sweet Home your family has been searching for. With solid bones, the home was recently refreshed for the things that matter.
$434,000

Condominium

200 SAINT ANDREWS BOULEVARD, WINTER PARK, Florida 32792

1Bedroom(s)
1Bathroom(s)
1Parking(s)
21Picture(s)
727Sqft
Listing Realtor is the owner. What a beautiful community this is! Four Seasons, one of the most sought-after communities in Winter Park. The association takes pride in a continuous well-done job maintaining the buildings and surroundings. This very nice, simple yet effective one bedroom one bath condo is ideal for an investor to rent out or for a single individual.
$135,000

Multifamily

1503 MICHIGAN AVENUE, WINTER PARK, Florida 32789

20Picture(s)
1,488Sqft
Great Duplex in Winter Park. One side leased and the other vacant. This Duplex is close to the interstate and to Winter Park Village . Private off street parking.
$399,000

Single Family

1987 BISCAYNE DRIVE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
23Picture(s)
1,469Sqft
Beautiful Winter Park Home! Fully renovated just a few years ago! This home features an Open Floor plan as you enter the front door with a Living Room/Kitchen combo, Newer Appliances, and a Dining Room for the family.
$330,000

Single Family

780 PINETREE ROAD, WINTER PARK, Florida 32789

4Bedroom(s)
5Bathroom(s)
1Parking(s)
25Picture(s)
4,553Sqft
New Listing in The Vias. Custom built, this 4 bedroom, 5 full bath pool home sits within Winter Park’s most sought-after neighborhood. Surrounded by multi-million dollar lakefront estates The Vias is a highly desirable, walkable community that’s minutes from the Raquet Club, Interlachen Golf and Country Club, and Park Avenue.
$1,995,000

Single Family

338 BLUE HERON DRIVE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,017Sqft
This 3 Bedroom, 3 bath, amazing mid-century modern home has some very unique features. A dramatic open, wood-burning fireplace that separates the living room and family room areas, renovated bathrooms, the Master bedroom and second bedroom have ensuite baths. The kitchen is updated with granite countertops, stainless appliances, a center island, and a view to the landscaped backyard and pool.
$760,000

Condominium

1695 LEE ROAD, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
19Picture(s)
881Sqft
Lovely 2 bedroom, 1 bathroom on a 2nd floor at Waterfall Cove, close to restaurants, shopping, and all major highways. The open living room is very spacious with sliding doors that lead to a large balcony. The unit comes with one assigned parking spot. This unit is perfect for an owner occupant or an investor, This unit rents very well.
$120,000

Single Family

2550 TEMPLE DRIVE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,227Sqft
Gorgeous, immaculate, well appointed Winter Park Home. This modern floor plan with an open concept and spacious layout is conveniently located in the heart of Winter Park. This home has an oversized lot with a summer kitchen, large area for outdoor entertaining and a lovely pool.
$1,390,000

Single Family

677 W SWOOPE AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
2Picture(s)
754Sqft
Location, Location, Location. Right in the heart of Winter Park. This property is the perfect opportunity to build a new home. Close to the Winter Park Village, Rollins College, Hannibal Square, Sun Rail, and many Fine Restaurants. Not far from Downtown Orlando. Excellent Schools. SOLD AS IS NO HOA Buyer to independently verify all measurements and condition.
$325,000

Lots And Land

27 STYMIE PLACE, WINTER PARK, Florida 32789

1Picture(s)
0.15Sqft
Great location! Walking distance to Dubsdread Golf Course & College Park main street. Close proximity to Downtown Orlando and all of the wonderful entertainment venues it has to offer. Easy access to I4 and other major highways. Excellent schools! Build your dream home! (There is a house on the property. Value is in the land.
$274,900

Lots And Land

25 STYMIE PLACE, WINTER PARK, Florida 32789

1Picture(s)
0.15Sqft
Great location! Close proximity to College Park, Downtown Orlando and all of the wonderful entertainment venues they have to offer. Excellent schools! Build your dream home! (There is a house on the property. Value is in the land.
$274,900

Single Family

1808 HOWELL BRANCH ROAD, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
18Picture(s)
1,539Sqft
Welcome Home! This home is a must see, don't miss out. This is the lowest priced move-in ready home in highly desirable Dommerich Elementary, Maitland Middle School and Winter Park High School zones. Completely hassle-free and move-in ready. Home was recently renovated and has too many upgrades to name.
$349,900

Single Family

690 N NEW YORK AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
5Bathroom(s)
2Parking(s)
6Picture(s)
4,901Sqft
Pre-Construction. To be built. Greens at Park. This address says it all…690 N. New York Avenue, where unparalleled luxury meets quintessential Winter Park lifestyle. Iconic English cottage architecture. This is a once in a lifetime opportunity to own a single family (fee simple) luxury real estate home in the heart of Winter Park.
$3,850,000

Townhouse

1003 S KENTUCKY AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
21Picture(s)
1,803Sqft
Granite counter tops/Stainless steel appliances with natural gas burners. Living area features gas fireplace,bamboo hardwood floors and surround sound speakers. Private court yard/Great for entertaining. Large Master suite with walk in closet. Located near shopping and Park Ave entertainment.
$599,000

Single Family

433 LAKEVIEW AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,925Sqft
Behind the facade of this charming 1940's bungalow, here lies an alluring Winter Park oasis which is far more considerable in size and scale than it appears. Take advantage of a rare opportunity to live in a secluded residential enclave on the shores of pristine Lake Killarney.
$590,000

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

Townhouse

125 S INTERLACHEN AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
3,244Sqft
Welcome to South Interlachen Place, an exquisite townhome community, boasting turn-key living at its finest. Showcasing the perfect blend of privacy and accessibility, with high-end finishes in all directions, UNIT # 2 offers 3,244 SF of living space, 3 bedrooms, 3 full baths, and 2 half baths, with multiple outdoor areas to enjoy.
$2,250,000

Single Family

1651 SUMMERLAND AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,023Sqft
Wonderful four bedroom family home on beautiful tree-lined Summerland. Walk to downtown Winter Park & Park Avenue, and close to Maitland City Center. This home sits on large 0.
$999,000

Single Family

2318 MULBRY DRIVE, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
1Parking(s)
25Picture(s)
1,190Sqft
Perfect place to build your dream home! Nestled in a quaint, quiet neighborhood in Winter Park, surrounded by million dollar homes. Tons of new construction on the street and in the surrounding area. Plenty of room to build - the city allows for nearly 3,000 square feet to be built on this lot. Zoned for the area's most sought-after schools: Audubon Park K-8 and Winter Park High School.
$415,000

Townhouse

1843 BLAINE TERRACE, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,114Sqft
Very nice three bedroom two bath split floor plan one car garage home in Winter Park. You’ll love the vaulted ceilings, open concept and the bay window in the spacious family room. This home offers laminate flooring in all 3 bedrooms and tile in the living areas. There is a screened covered patio and a fully fenced backyard.
$259,000

Single Family

2034 EAST END AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
1Parking(s)
25Picture(s)
2,714Sqft
New listing! Check out this amazing, newly built home by Barefoot Brothers, just steps from the East End Market. Built in 2019, this 3-bedroom, 3.5 bath home features an open floor plan with an oversized 1-car garage.
$1,135,000

Single Family

1841 JESSICA COURT, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,646Sqft
WATERBRIDGE IN WINTER PARK-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.
$549,000

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.
$610,000

Single Family

543 SHEPHERD AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,707Sqft
This stunning home is located in the heart of Winter Park on a beautiful street..A courtyard welcomes you with a Wrought Iron Gate. This home has an open floor plan with a Wood-burning Fireplace in the living room that has French Doors that open to a beautiful back terrace.
$1,250,000

Lots And Land

2005 SYCAMORE DRIVE, WINTER PARK, Florida 32789

8Picture(s)
0.19Acre
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.
$550,000

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.
$575,000

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

Single Family

2550 VENETIAN WAY, WINTER PARK, Florida 32789

4Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
4,875Sqft
"The richness of an artist is the fusion of influences that have shaped his life and work", ~ Fernando Botero.
$2,400,000

Single Family

1421 WOODALE AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
25Picture(s)
1,628Sqft
This charming and updated split 3 bedroom 2 bath bungalow on an oversized fenced-in lot, It is located on a quiet cobblestone street in the heart of one of Florida’s most sought-after locations, rich in history, home to Rollins College and Park Avenue.
$523,800

Condominium

1250 S DENNING DRIVE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
23Picture(s)
898Sqft
Cute 2 bedroom , 2 bathroom condo in Winter Park. Mead Gardens Condos are walking distance to Park Ave, Azalea Tennis Center, Rollins College, Mead Gardens, dining options as well as being zoned for the new K-8 Audubon School. This condo is a first floor unit with screened in lanai facing the community pool. New AC 2019.
$189,900

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

Lots And Land

460 W LYMAN AVENUE, WINTER PARK, Florida 32789

16Picture(s)
0.30Acre
Don't miss this rare opportunity to build your dream home in the most prime location in Central Florida! The double lot, approximately 13,125 SF lot, is surrounded by all of the prestige and excitement that makes the City of Winter Park so special.
$750,000

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

Townhouse

125 S INTERLACHEN AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
4,160Sqft
Life doesn’t get more luxurious or convenient than at South Interlachen Place! This prestigious community consists of six exquisitely built townhomes, boasting turn-key living at its finest. Expanding over 4,000 SF, Unit 6 is the marquis CORNER UNIT, and showcases the perfect blend of privacy and accessibility, with high-end finishes in all directions.
$2,990,000

Townhouse

125 S INTERLACHEN AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
3,244Sqft
Welcome to South Interlachen Place, an exquisite townhome community, boasting turn-key living at its finest. Showcasing the perfect blend of privacy and accessibility, with high-end finishes in all directions, UNIT 5 offers 3,244 SF of living space, 3 bedrooms, 3 full baths, and 2 half baths, with multiple outdoor areas to enjoy.
$2,250,000

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

Condominium

100 S VIRGINIA AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,599Sqft
One story unit at the Douglas Grand building in downtown Winter Park. High-end appliances and fixtures, granite counter tops in the kitchen and all baths. Oversized walk-in shower and garden bath in the master suite, walk-in closets. Two reserved parking spots conveniently located on your floor in a gated parking garage make for extremely convenient and secure parking.
$950,000
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Zachary Tuohey - Realtor - Orlando Homes for Sale and Real Estate Listings