Winter Park Homes for Sale

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Single Family

1371 LYNDALE BOULEVARD, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,599Sqft
On the quiet, tree-lined, brick streets of Winter Park, you'll find 1371 Lyndale Blvd. A 4 bedroom, 3 bath home is situated on a corner lot and close to Winter Park favorites like, The Enzian, Winter Park Village and Park Avenue district.
$589,000

Single Family

1310 SUMMERLAND AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,302Sqft
Updated, timeless & move in ready is this 5 bedroom & 3.5 bath estate pool home in the heart of Winter Park in a sought-after tree-lined neighborhood walking distance to Park Avenue! The new interior/exterior paint and landscaping, welcomes family and guests with the circular drive & additional parking. The large front porch is perfect to relax or catch up from the day.
$1,095,000

Single Family

1751 GOODRICH AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,170Sqft
This almost-new light and bright home with top of the line finishes was fully renovated in 2019. Seller will provide 1 year home warranty. 2,172 sq ft under air, 4 Beds, 3.5 bathrooms and 2 car garage, this home has no details left behind. Full of upgrades and technology, this smart home will do things for you.
$849,900

Single Family

1080 KENWOOD AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
11Picture(s)
3,317Sqft
Under Construction. BRAND NEW CONSTRUCTION IN WINTER PARK! Scheduled to be completed in October 2020 this stunning modern farmhouse was designed and built by Homes by Carmen Dominguez. Every detail of this home has been thoughtfully planned and executed to perfection. The fantastic layout, which was a 2020 Parade of Homes Winner for best design feature, offers 3,317 Sf of open living space.
$1,250,000

Single Family

280 STIRLING AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,428Sqft
Tranquil & Timeless Treasure meticulously maintained by original owner. .58 acre tree canopied property framed by Howell Creek & wooded lot is the perfect setting for this charming yet elegant 4/3.5, 2 story beauty. Outstanding location! Scenic stroll to Rollins College & Park Avenue's shoppes & restaurants.
$2,144,000

Townhouse

1273 MICHIGAN AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
10Picture(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.
$450,000

Townhouse

756 MCINTYRE AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,690Sqft
Just Listed! Walk to Park Avenue from this beautifully maintained 3 bedroom, 2.5 bath townhome in the historic College Quarter neighborhood of Winter Park. Located just blocks from upscale dining and boutique shops as well as Rollins College, this home features an expansive interior layout with over 2,600 SF.
$650,000

Single Family

110 CHELTON CIRCLE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
10Picture(s)
4,225Sqft
WINTER PARK-Amazing character home in the Heart of Winter Park! Stunning interior – 4 bedrooms, 4 full baths, beautiful wood floors, high ceilings, custom details, and bright natural light throughout. Formal living and dining room, large galley kitchen, and an open family room allow for lots of room to entertain friends and family.
$1,425,000

Lots And Land

2888 LOLISSA LANE, WINTER PARK, Florida 32789

17Picture(s)
0.32Acre
Build your dream home on cul-de-sac in Winter Park 32789! Superior 92 x 150 lot cleared, fenced and ready for residential home. Privacy abounds with beautiful views of quiet, wooded backyard. Most desirable schools- Dommerich, Maitland Middle and Winter Park High School. Minutes from Winter Park and Maitland restaurants. Lots of neighborhood biking and walking. Short drive to Park Avenue.
$265,000

Lots And Land

715 DOUGLAS AVENUE, WINTER PARK, Florida 32789

21Picture(s)
0.08Acre
This lot is cleared and ready for you to build your dream home! Douglas Avenue is a quiet street and a must see.
$275,000

Single Family

411 GARFIELD AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
25Picture(s)
912Sqft
Come take a look at this one of a kind farmhouse chic house just 2 blocks from Park Ave and a short stroll to Hannibal Square. Originally built in 1925, this home has been completely redone from top to bottom. First you will notice the lush upscale landscaping, new exterior wood board and batten siding with a touch of wood beams to welcome you on the front porch.
$425,000

Single Family

2218 VIA TUSCANY, WINTER PARK, Florida 32789

5Bedroom(s)
7Bathroom(s)
2Parking(s)
25Picture(s)
4,423Sqft
SUPERIOR QUALITY one of a kind home built by Zoltan Homes, in prime location in Winter Park. Boasting a tremendous open floor plan with over 11ft ceilings on the 1st floor and 10ft ceilings on the 2nd floor, gorgeous wide plank oak flooring and truly exceptional detailed finishes throughout.
$2,345,000

Single Family

2206 VENETIAN WAY, WINTER PARK, Florida 32789

5Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
4,957Sqft
Welcome to this classic and charming 1925 traditional home in the Vias! The home sits on a lush oversized .45 acre lot in the heart of Winter Park and was completely renovated in 2003. Features include: Yellow and Heart Pine flooring, 10ft.
$1,295,000

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

490 FAIRFAX AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,358Sqft
Winter Park contemporary home that was designed for both grand scale entertaining and comfortable family living. This impeccable light filled residence is well appointed on deep landscaped lot that backs up to active stream - Howell Creek.
$1,335,000

Single Family

1731 VIA GENOA, WINTER PARK, Florida 32789

4Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
3,795Sqft
Exceptionally beautiful private pool home in the most desirable heart of the Vias. Unmatched curb appeal yet very private. Remote gated entry for cars, paved semicircular motor court. Gorgeous mix of warm woods and neutral tones. Minutes from Winter Park Racquet Club, Park Avenue restaurants, shopping, Farmers Market and more.
$1,579,000

Single Family

611 PENN PLACE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
4,023Sqft
This stunning & completely renovated home is the perfect combination of location, functionality, and glamour! Enjoy living walking distance from Park Avenue's restaurants, shops and the WP Golf Course! Over 4,000 SF of effortless living, wrapped in brand new landscaping, on a 3-sided corner lot, with all new landscape & lighting, a brand-new roof (19), new exterior light fixtures, freshly
$1,595,000

Single Family

1745 HOLLYWOOD AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,798Sqft
Located in the heart of Winter Park this home is one of the LOWEST PRICED per square foot you will find! EXTENDED FAMILY? Fabulous 3-way split floor plan with spacious master retreat on main floor along with two other bedrooms provides plenty of privacy for everyone.
$924,888

Single Family

2010 CORNELL AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
1Parking(s)
21Picture(s)
1,389Sqft
** Back on the Market** -Buyer Financing fell trough. -Cute, cozy and well-maintained single family house, conveniently located in very close proximity to Dubsdread Golf Course and College Park area.
$324,000

Single Family

2813 NORTHWOOD BOULEVARD, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
2Picture(s)
3,443Sqft
Under Construction. Under Construction. NEW HOME! all the major appliances and finishes are in the home! This two-story contemporary home features 4 bedrooms, 3 full and one half bathrooms open floor plan, this residence embraces natural light and features a vaulted foyer with a glass railing staircase and beautiful sliding glass doors that frame the outdoor living area.
$1,099,999

Single Family

444 SHEPHERD AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
6Bathroom(s)
2Parking(s)
25Picture(s)
4,322Sqft
This latest masterpiece from Winter Park’s premier builder FG Schaub Custom Homes is complete! This spacious 4,322 s/f home offers five bedrooms, five full baths, and one half bath of exceptional space. This sensational Mid Century Modern home boasts an open floor plan, chef inspired kitchen, oversized master suite, and a second bedroom/office ensuite all on the first floor.
$1,689,900

Single Family

1166 OXFORD ROAD, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
11Picture(s)
3,764Sqft
Charmer in Olde Winter Park, rare renovation opportunity in Virginia Heights! Mother in Law rental above the garage rents at $600 per month. Lots of unique features in this 1947 custom built home - one family has owned it since 1947. Two Story Home.
$898,500

Single Family

1771 BRYAN AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,507Sqft
NEW EXTERIOR PAINT COMING SOON...Gray with White Trim! GORGEOUS, REMODELED Victorian two-story 3BR, 2.5 BA home with 2-car Detached Garage located in the heart of charming Olde Winter Park. ZONED for TOP-RATED WINTER PARK SCHOOLS! You’ll love the light and bright interior with its 10-FT VOLUME CEILINGS & Newer, large baseboards throughout the first floor.
$669,000

Rental

6877 JACKMAN BOULEVARD, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
2Parking(s)
17Picture(s)
1,530Sqft
The home has a fenced outdoor living space! This home features plenty of storage space. The kitchen has updated appliances with rich cabinets and ample counter space. Smart Home is a monthly service that helps you manage access to your home and save on your energy bill.
$1,830

Condominium

203 LEWFIELD CIRCLE, WINTER PARK, Florida 32792

2Bedroom(s)
2Bathroom(s)
17Picture(s)
927Sqft
Winter Park Opportunity, Amazing Location, and Move In Ready! This 2 Bedroom 2 Bath ground floor condo is located in the desirable community of The Stratford. Conveniently near UCF, Rollins College, Valencia College, Park Avenue, Downtown Orlando, as well as easy accessibility to grocery stores, great shopping, and major employers.
$117,000

Single Family

2241 KING JOHNS COURT, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,619Sqft
Fresh clean and in Winter Park. Minutes from major highways, Winter Parks famous Park Avenue and one of the nicest golf clubs in Central Florida, Interlachen Country Club. Be in downtown Orlando in just minutes, Park Ave for some shopping or dining, and so many other local amazing places in just a few short minutes. The property is on a corner lot with a fully fenced-in and private backyard.
$349,900

Condominium

258 LEWFIELD CIRCLE, WINTER PARK, Florida 32792

1Bedroom(s)
1Bathroom(s)
25Picture(s)
678Sqft
Owner occupied the opportunity you've been waiting for has finally arrived. Beautiful renovated Condo with 1 bedroom and 1 Bath on second floor with pool view. New cabinet. New appliances. Freshly painted. Renovated bathroom. New toilet. New vanity. New insulation. The community has two beautiful pools, tennis courts and small gym. Excellent location.
$95,000

Single Family

7503 BETTY STREET, WINTER PARK, Florida 32792

2Bedroom(s)
2Bathroom(s)
2Parking(s)
6Picture(s)
1,338Sqft
A perfect fit for a starter or forever home, this 2/2/2 will be the envy of Zoom meetings everywhere. Lots of great backgrounds in the expansive entry, living room, dining room and kitchen will keep your colleagues and clients engaged instead of daydreaming! The large master with walk-in closet and refurbished vanity also got recent bamboo flooring, just like much of the rest of the home.
$253,390

Single Family

1790 PERUVIAN LANE, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,064Sqft
Cute 3 bedroom, 1.5 bathroom, single-family home in the charming Eastbrook community of Winter Park! This home features an open floor plan which immediately opens to the living room with laminate flooring, and a large window facing the front yard. This home features a primary bedroom with closet space and an attached bathroom with a tub/shower combination.
$227,900

Single Family

1404 PERUVIAN LANE, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
1Parking(s)
23Picture(s)
1,452Sqft
NEW< NEW this home is completely renovated in compliance with current building code done in the years of 2019-2020....the home has new roof, gutters, facia and soffit...new electrical panel and wiring, new 200 amp electrical service, new AC compressor and air handler ,new duck work, new insulation in walls and ceilings.
$279,900

Condominium

252 LEWFIELD CIRCLE, WINTER PARK, Florida 32792

2Bedroom(s)
2Bathroom(s)
25Picture(s)
927Sqft
2ND FLOOR CONDO in an AMAZING LOCATION in WINTER PARK!!! Located in the desirable Stratford community in Winter Park. Perfectly located near Full Sail, Rollins College, UCF, Downtown Winter Park, convenient shopping venues, great restaurants and many more.
$125,000

Condominium

296 LEWFIELD CIRCLE, WINTER PARK, Florida 32792

1Bedroom(s)
1Bathroom(s)
19Picture(s)
678Sqft
Excellent neat as a pin one bedroom condo within the desirable Stratford community of Winter Park. Convenient to shopping and restaurants and access to neighboring towns. New roof, new gutter system, entire unit re-piped, newer water heater, newer stove & dishwasher. Newer stack washer and dryer to remain in the unit. Beautiful wood looking ceramic tile flooring throughout.
$99,900

Commercial

1788 W FAIRBANKS AVENUE, WINTER PARK, Florida 32789

10Picture(s)
7,645Sqft
List Price is for 3 Parcels: This listing includes two other Parcels that are all being sold together. Parcel 12-22-29-5000-04-040, which is a parking lot that serves as this parcel's parking lot. Parcel 12-22-29-5000-04-050, is a two-story building also owned by the seller. See MLS Listing#O5852283 for further details. Both buildings are ADA compliant.
$3,950,000

Rental

600 W CALLAHAN STREET, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
1Parking(s)
25Picture(s)
754Sqft
For Rent - Super cute 2 Bedroom, 1 Bath home in Winter Park! Walking distance to the Winter Park Village, Hannibal Square, Park Avenue and more. Recently updated this home sits on a large corner lot and has been freshly painted inside and out, and features brand new kitchen countertops, all new light fixtures, white tile flooring, and bright natural light. Home also has a brand new roof and AC.
$1,500

Single Family

2011 N PARK AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
1Picture(s)
1,176Sqft
LOWEST PRICE HOME ON N PARK AVE IN WINTER PARK.
$399,000

Single Family

915 N KENTUCKY AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,676Sqft
CHARMING WINTER PARK BUNGALOW OVERLOOKS LAKE MIDGET CONVENIENT LOCATION- MANY HOMES ON BRICK STREET OVER 1 MILLION DOLLARS - HEART OF PINE WOOD FLOORS IN ORIGINAL LR/DR AND BEDROOMS LARGE MASTER BEDROOM WITH LARGE WINDOWS OVERLOOKING YARD. FRONT PORCH AND REAR SCREENED PORCH CONVENIENT TO PARK AVE AND WINTER PARK VILLAGE. NATURAL GAS ON LOCK BOX.
$450,000

Townhouse

1274 MILLER AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
22Picture(s)
1,628Sqft
Winter Park Townhome offers 3 Bed, 2.5 Bath home amazing location easy access to major roadways, shopping, the very active Orlando ave district of Winter Park, sunrail and Florida Hospital .
$344,900

Single Family

931 N PARK AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
17Picture(s)
2,691Sqft
Here it is!! One of the largest lots on Park Avenue with easy walking to shops and restaurants. The golf course is right here as well. This lovely pool home has been lovingly cared for over the years and is being sold AS IS. Come make it your own or start over and remove the home since the homes on either side have been removed. The prices along the Avenue for newer homes are well over 3 million.
$1,490,000

Lots And Land

931 N PARK AVENUE, WINTER PARK, Florida 32789

23Picture(s)
0.41Acre
A most unique and awesome opportunity to build your dream home on the most sought after address in Winter Park with an easy access to all the shopping and restaurants. No need to drive when you live here and if you love golf you can stroll to the golf course as well.
$1,490,000

Single Family

1737 OAKHURST AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
2,300Sqft
One or more photo(s) has been virtually staged. Charming home located in the heart of Winter Park Historical District. Split floor plan with upgraded laminate floors throughout. Newer roof, newer A/C, vaulted ceilings, updated kitchen including granite counter tops & stainless steel appliances.
$520,000

Single Family

1808 HOWELL BRANCH ROAD, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
18Picture(s)
1,539Sqft
Perfect home for first-time buyers and/or investors alike. Great Winter Park property, zoned for top-rated and sought after Dommerich Elementary, Maitland Middle and Winter Park High School. Too many upgrades in the last couple of years to even think about naming them all. You won't find better bones in Winter Park for less money.
$269,900

Condominium

1500 GAY ROAD, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
25Picture(s)
1,026Sqft
ABSOLUTELY STUNNING CONDO! This unit has been completely renovated with gorgeous finishes. If you like modern, you will love this place. Everything on the interior is new including the a/c duct work, the a/c was replaced in July 2018 and water heater in July 2014. This 2 bedroom 2 bath features large bedrooms with a open living concept. If you like to cook, you will love this kitchen.
$254,900

Single Family

243 ORANGE TERRACE DRIVE, WINTER PARK, Florida 32789

3Bedroom(s)
1Bathroom(s)
2Parking(s)
21Picture(s)
1,178Sqft
LOCATION, LOCATION, LOCATION! THIS 3/1 HOME HAS BEEN REMODELED. ALL NEW APPLIANCES, ROOF, AC AND NEW PAINT! THIS HOME HAS A COZY LAYOUT WITH A FENCED IN BACKYARD. LOCATED MINUTES FROM ALL OF WINTER PARK SHOPS AND EATERIES.
$325,000

Single Family

1571 HARRIS CIRCLE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,816Sqft
Dramatic 3 Bedroom 2.5 bath lakefront Mediterranean home on Lake Sylvan. A large top floor master-suite with luxurious bath & closet and a lakeside balcony. The main floor is great for entertaining with a chef's kitchen featuring a Wolf 6 burner gas range, Sub-Zero refrigerator/freezer, tons of light wood cabinets and an eat-in area.
$949,000

Townhouse

1762 MONDRIAN CIRCLE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,479Sqft
Pre-Construction. To be built. Pre-Construction. To be built. Perfectly located between the tranquility of nature and the best in local shopping, restaurants and bars. Lake Killarney Townhomes offer private boat slips and peaceful views of the lake.
$660,750

Townhouse

1764 MONDRIAN CIRCLE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,479Sqft
Pre-Construction. To be built. Perfectly located between the tranquility of nature and the best in local shopping, restaurants and bars. Lake Killarney Townhomes offer private boat slips and peaceful views of the lake.
$660,750

Condominium

250 CAROLINA AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,340Sqft
Welcome home to Park West Condominiums, and the brick streets of beautiful, historic Winter Park, Florida.
$369,900

Lots And Land

280 E LAKE SUE AVENUE, WINTER PARK, Florida 32789

7Picture(s)
0.45Acre
Beautifully elevated lot on scenic corner in charming Winter Park neighborhood. The existing home was built in 1950 and overall age and functional design imparts negligible value. The value of this property is in the land.
$711,000
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