Winter Park Homes for Sale

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Single Family

138 DETMAR DRIVE, WINTER PARK, Florida 32789

6Bedroom(s)
8Bathroom(s)
3Parking(s)
25Picture(s)
5,430Sqft
This truly unique historic property built in the 1880's has been described as the most Victorian cottage still standing in Winter Park and perhaps the finest example of Victorian architecture in the region. Over time, it has been carefully restored, remodeled with respect and modern touches, and expanded while retaining its historic character. This beautiful property consists of a 3 bedroom, 4.
$2,250,000

Condominium

315 E NEW ENGLAND AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
2Parking(s)
20Picture(s)
1,605Sqft
STUNNING WINTER PARK two bedroom condo oriented in the most private section of the Jewel of Winter Park! Villa Siena is located 2 blocks off Park Avenue and is directly across from the chic Alfond Inn.
$965,000

Single Family

1830 GIPSON GREEN LN, WINTER PARK, Florida 32789

5Bedroom(s)
7Bathroom(s)
3Parking(s)
25Picture(s)
6,444Sqft
Luxury and elegance abound in this private, gated Winter Park Chain of Lakes estate, nestled on almost an acre at the end of a secluded cul-de-sac, with elevated views of beautiful Lake Maitland. Remodeled by award-winning interior designer, Betsy Godfrey, and designed with entertaining in mind, the rooms are large, timeless and sophisticated.
$4,195,000

Condominium

315 E NEW ENGLAND AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,806Sqft
One or more photo(s) has been virtually staged. Winter Park’s “Luxury Condo Corridor,” featuring VILLA SIENA is just steps away from famed Park Ave with award winning restaurants, cafés, boutiques, and Rollins College and is directly across the street from the Alfond Inn. This 3 bed, 3.
$1,479,000

Single Family

1601 LEGION DRIVE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,281Sqft
Presenting an exquisite new listing in the Heart of Winter Park. Completely remodeled in 2019 from floor to ceiling, this casually elegant, single-story residence features three bedrooms, two full baths as well as two half baths, formal living and dining, a gourmet kitchen, and designer finishes throughout.
$1,295,000

Single Family

433 E NEW ENGLAND AVENUE, WINTER PARK, Florida 32789

10Bedroom(s)
14Bathroom(s)
4Parking(s)
25Picture(s)
8,325Sqft
A unique offering to say the least. Originally built in 1920, the woodwork highlights the best of lost skills retained in the massive renovation done in 2009. Sitting on over 1/2 acre this home is a short walk to park Ave and city hall. The library with an office highlights the skills of the craftsman society.
$4,200,000

Condominium

267 E CANTON AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,057Sqft
DOWNTOWN WINTER PARK condo located in WINTERSET, a secure building with access only by key or buzzer. This fabulous 2 BR - 2 BA has LAKE AND TREE TOP VIEWS! The condo has been TOTALLY RENOVATED: mocha stained oak rift and quartered flooring, new baseboards, solid wood doors, crown moulding, woven wooden blinds, newer windows, designer light fixtures, hardware and paint colors throughout.
$594,000

Condominium

315 E NEW ENGLAND AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,276Sqft
A stunning ground floor offering in the Jewel of Winter Park facing the Alfond Inn! Villa Siena is located 2 blocks off Park Avenue and is within comfortable walking distance to Rollins College, upscale dining, and some of the finest boutique shopping in the Orlando metropolitan area.
$1,750,000

Single Family

911 OSCEOLA AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,244Sqft
One of a kind meticulously maintained ONE STORY Winter Park Charmer within walking distance to Downtown Park Avenue. Originally custom built for the local Miller hardware store family this home sits on almost a half acre lot offering mature landscape, charm, ample natural light and character throughout the grounds.
$1,125,000

Condominium

101 S NEW YORK AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
25Picture(s)
3,174Sqft
Incredible two-story condo unit available at Winter Park’s premier address, The Douglas Grand. Located on the 3rd floor of this access-controlled building, this 3-bedroom, 3.5 bath unit boasts an elegant interior with designer finishes and large, comfortable living spaces. On the first floor of the unit enter the home through the foyer entry.
$1,595,000

Single Family

1324 INDIANA AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
21Picture(s)
1,692Sqft
Absolutely gorgeous renovation of this 1930’s Winter Park bungalow. The home has been impeccably restored to save the historic architectural details and adding the modern amenities such as a beautiful gourmet kitchen, complete with custom cabinetry, stainless steel appliances and hard surface counter tops.
$525,000

Single Family

1370 INDIANA AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
2Bathroom(s)
25Picture(s)
1,184Sqft
Charming four bedroom two bathroom Winter Park gem with updated and great design touches. This home boasts a large open front porch, beautiful hardwood floors, a light and bright kitchen with quartz countertops, stainless steel appliances, a gas range, updated bathrooms, custom-built closets, fresh paint, crown molding, electric fireplaces, and a fenced back yard.
$410,000

Single Family

2032 TEMPLE DRIVE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,931Sqft
Start off the new year #2021 in this Winter Park Home! Move right in and enjoy the gorgeous space with a very flexible floor plan offering 4 bedrooms, plus an extra room downstairs perfect for a home office or amazing customizable home drop zone plus an open upstairs loft.
$919,900

Single Family

1849 LOCH BERRY ROAD, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,490Sqft
MOVE IN TODAY! This charming, updated 3/2 Winter Park home features 1,490 sq.ft. of living space, a split floor plan, crown molding, two-car garage with AC and an epoxy coated flooring, a deck ideal for entertaining, shed for storage, a PVC fenced yard with room to park an RV or boat on a beautifully landscaped, large corner lot.
$459,000

Single Family

1437 CHAPMAN CIRCLE, WINTER PARK, Florida 32789

5Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,732Sqft
Welcome to this elegant, one-of-a-kind, colonial-style home in Winter Park’s Windsong community. The classic brick exterior is remarkable and graciously invites you into the 5 bedroom, 3.5 bath home which is superb.
$1,195,000

Single Family

247 W LYMAN AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
5Picture(s)
988Sqft
Heart of Winter Park! 2 Lots! Build on 14,867 sq ft of land (.34 acres, 2 lots) - - One Block to Park Avenue - - with upscale restaurants and shopping! Two single-family adjacent lots in this parcel. A small home, 2/1, built in 1970, remains today. Has newer A/C and new roof 2019, freshly painted.
$785,000

Single Family

1730 GREENWICH AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
4,611Sqft
One or more photo(s) has been virtually staged. Located in the heart of Winter Park, this virtually new Modern Florida Coastal custom pool home was built by David Cahill (2015) who’s attention to detail is widely respected. It is well appointed and showcases over 4,600 SQFT of open living space.
$1,697,000

Condominium

1163 WASHINGTON AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,263Sqft
One or more photo(s) has been virtually staged. You won't believe this chic and cozy 2/2 condo with a 1 car garage in Winter park. Walk to Park Ave, Rollins College, Meads Garden or play a few sets at the Winter Park Tennis club. Step back in time and marvel unique Winter Park with its cobble stone streets and many beautiful homes from all time periods.
$354,000

Condominium

311 E MORSE BOULEVARD, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
2,006Sqft
Stunning complete renovation makes this spacious lakefront, lake view condo like new! Perfectly situated in Downtown Winter Park, where restaurants, shopping, churches and Central Park are right in your neighborhood, this 2014 reno took everything down to the studs, bare floor and raised the ceiling.
$975,000

Condominium

311 E MORSE BOULEVARD, WINTER PARK, Florida 32789

1Bedroom(s)
1Bathroom(s)
1Parking(s)
25Picture(s)
1,192Sqft
Your new home in the heart of Winter Park is just two blocks from Park Avenue. This one-bedroom, one-bathroom groundfloor condo at Whisperings Waters allows easy access to some of the best dining, entertainment, and luxury shopping options in Central Florida.
$350,000

Single Family

1128 PRESERVE POINT DRIVE, WINTER PARK, Florida 32789

5Bedroom(s)
5Bathroom(s)
3Parking(s)
10Picture(s)
6,179Sqft
Welcome to this gorgeous, one-of-a-kind, contemporary-style home with over 150’ on the shores of Lake Berry. Custom built and architecturally stunning, this 5 bedroom, 4.5 bath home is pure perfection inside and out.
$4,199,000

Condominium

1140 WASHINGTON AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,069Sqft
Fabulous opportunity in the very desirable Winter Park! Location can't be beat! This unique condo with over 2000 SF living space is nestled on a tree and brick-lined street, features a 3 bedroom 2.5 bath townhome with open kitchen/family room concept with wood burning fireplace and beautiful natural light from ceiling to floor windows.
$354,000

Townhouse

345 W WELBOURNE AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,734Sqft
Opportunity at The Douglas Grand! Enjoy a carefree, urban lifestyle in beautiful downtown Winter Park - just one block from chic Park Avenue with its lovely boutique shoppes, bistros, sidewalk cafes and restaurants - and of course the beauty of Central Park - and old-fashioned holiday parades. A wonderful, carefree lifestyle awaits you - and there is so much to do...
$799,000

Condominium

228 SCOTTSDALE SQUARE, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
10Picture(s)
1,250Sqft
Completely renovated 3 Bedroom Loft Style condo for sale, new flooring, painting, main door, lights and fixtures, located on 436/Semoran Blvd only 10 min to Orlando Downtown. Tenant occupied unit offers Perfect opportunity for your Investment cash flow. Call for showing.
$140,000
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