Winter Park, Florida MLS listings - Homes for Sale

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Homes For Sale » Florida » Orange county » Winter Park
Villa View Park
$1,425,000
660 Pansy Avenue
5 bed / 5 bath Single Family Home
MLS #O5363481
4,350 sq. ft.
New Construction! 5 bdrm, 5 bath, 1 half bath, 4350 sf French New Orleans style within a bike ride to Winter Park's renowned Park Ave shopping/dining district. Guest and masters suite downstairs. 11x16 walk in closet!…
Villa Siena
$1,495,000
315 E New England Avenue #3
3 bed / 4 bath Condo
MLS #O5345837
3,839 sq. ft.
Winter Park, FL 32789
First Floor, End Unit, $389.00 sq. ft. MUST SEE!
Cloister Grove
$1,950,000
1270 Via Salerno
4 bed / 4 bath Single Family Home
MLS #G4814923
6,138 sq. ft.
Winter Park, FL 32789
This home is ready for you to decorate it for the holidays. Bring in the New Year in your new home. Located in the “Via’s” Winter Park neighborhood, this Lake Front home offers panoramic views of Lake Knowles…
Robert Dhu Macdonald Park
$2,800,000
1020 N Park Avenue
5 bed / 8 bath Single Family Home
MLS #O5380685
8,342 sq. ft.
Winter Park, FL 32789
Your opportunity to own a Masterpiece on the most prestigious street in Central Florida! This Classic Estate offers elegance, luxury and entertainment in the heart of desired Winter Park. With just a short walk…
South Interlachen Place
$2,144,000
125 S Interlachen Avenue #5
2 bed / 5 bath Town Home
MLS #O5389629
3,244 sq. ft.
Winter Park, FL 32789
Under Construction. Only two residences remain! Your opportunity to own unprecedented luxury in the most exclusive area of Winter Park has arrived. South Interlachen Place is around the corner from world famous Park…
Windermere Woods
$4,250,000
1000 Genius Drive
5 bed / 7 bath Single Family Home
MLS #O5398017
8,157 sq. ft.
Winter Park, FL 32789
Welcome to 1000 Genius Drive……..a piece of Winter Park history! This Mediterranean lakefront estate on 1.89 acres was originally designed and constructed in 1925 by a group of Winter Park league of businessmen to be…
Adair Place
$3,500,000
2150 Via Tuscany
7 bed / 10 bath Single Family Home
MLS #O5398109
7,670 sq. ft.
Winter Park, FL 32789
Timeless perfection encompasses every room of this stunning Winter Park estate. Custom built by Charles Clayton, this seven bedroom, seven bath home exudes character and charm throughout and includes features so seldom…
Campo Bello
$625,000
1790 Edwin Boulevard
4 bed / 4 bath Single Family Home
MLS #O5405458
2,393 sq. ft.
Winter Park, FL 32789
N E W P R I C E!!! PRISTINE. SOPHISTICATED. TURN KEY! Beautiful new front double doors welcome you to this immaculate home complete with lovely finishes. Gleaming hardwood floors, high ceilings & crown molding…
$875,000

Commercial Property
MLS #S4823408
4,032 sq. ft.
Winter Park, FL 32792
good location,on busy area of Aloma Avenue, total of 5 spaces. 1 is vacant and for lease now for $1100.00/ mo I occupied by Insurance Agency, convenience STORE clean place and enough parking space. Back is using by…
Landmark Winter Park Condo
$1,544,236
140 E Morse Boulevard #D
3 bed / 3 bath Condo
MLS #O5411468
2,450 sq. ft.
Winter Park, FL 32789
Don't miss the opportunity to own the last "shell" residence with buildout allowance in "The Landmark" - Winter Park's most esteemed condominium residence nestled among high profile streets and only steps from Park…
Lake Waunatta Woods Unit 02
$849,900
8041 Lake Waunatta Drive
4 bed / 5 bath Single Family Home
MLS #O5410691
5,329 sq. ft.
Winter Park, FL 32792
PRICED BELOW APPRAISED VALUE! Fabulous lakefront opportunity in Winter Park! This stunning custom-built pool home, which sits on private spring-fed Lake Waunatta, offers vaulted ceilings, wood floors & a spacious…
Enclave At Aloma
$548,597
7868 Pleasant Pine Circle
4 bed / 4 bath Single Family Home
MLS #T2803970
3,514 sq. ft.
Winter Park, FL 32792
Brand new 2 story home in Winter Park community! Separate tub & shower in master, hand scraped wood flooring in most of home All stainless steel appliances in kitchen, and a washer and dryer, custom window treatments…
Penn North
$1,375,000
1010 N Pennsylvania Avenue
4 bed / 5 bath Single Family Home
MLS #O5423348
3,763 sq. ft.
Winter Park, FL 32789
under construction with november 2016 completion. the first of four fabulous single family detached homes as a part of a planned development being built in downtown winter park adjacent to the golf course and a short…
Landmark Winter Park Condo
$1,629,000
140 E Morse Boulevard #J
3 bed / 3 bath Condo
MLS #O5423251
2,143 sq. ft.
Winter Park, FL 32789
Welcome home to an exclusive residence detailing all the amenities of luxurious living. Located in the heart of charming downtown Winter Park, just steps off beautiful Park Avenue with its many fine bars, boutiques,…
Windsong North Shore 43/74
$949,000
567 Genius Drive
5 bed / 4 bath Single Family Home
MLS #O5425905
3,672 sq. ft.
Winter Park, FL 32789
Windsong 5 bedroom 3.5 bath Mediterranean. First floor master bedroom overlooking beautiful pool are with summer kitchen. Hardwood floors, crown molding, travertine and custom gourmet kitchen opens to family room and…
$1,795,000
210 E Canton Avenue
3 bed / 3 bath Town Home
MLS #O5425778
4,100 sq. ft.
Winter Park, FL 32789
Walk to Park Avenue. This prime luxury townhouse has amazing features with stylish retro touches in the most desirable location of Winter Park. Private elevator within the residence, private terraces, balconies and a…
Killarney Estates
$699,000
430 Killarney Drive
2 bed / 1 bath Single Family Home
MLS #O5424645
1,444 sq. ft.
Winter Park, FL 32789
build your new lakefront estate on beautiful 234 acre lake killarney, a mile long, private, spring-fed lake. site is on the southeast shore just 3 blocks from hillstone's restaurant, and an area where there is much new…
Lake Virginia Shores
$869,000
543 E Lake Sue Avenue
4 bed / 5 bath Single Family Home
MLS #O5418499
3,657 sq. ft.
Four bedroom, four and one-half bath pool home tucked away in Lake Virginia Shores. Full of character, this home features dark, wide-plank wood floors, crown molding, and high beadboard ceilings. Formal living and…
Sicilian Shores
$2,850,000
711 Pinetree Road
4 bed / 5 bath Single Family Home
MLS #O5427789
4,770 sq. ft.
Winter Park, FL 32789
Gorgeous Lake Maitland one-owner custom home on premier street in the heart of the Vias. Situated on over 1/2 acre, this home boasts abundant extras throughout. Huge kitchen with granite counters, great storage, sunny…
Killarney Estates
$699,000
MLS #O5425925
0.5 acres
Winter Park, FL 32789
build your new lakefront estate on beautiful 234 acre lake killarney, a mile long, private, spring-fed lake. site is on the southeast shore just 3 blocks from hillstone's restaurant, and an area where there is much new…
Sevilla
$985,000
304 Santiago Drive
5 bed / 5 bath Single Family Home
MLS #O5416567
4,213 sq. ft.
Winter Park, FL 32789
Just Reduced! Custom built, five bedroom, four and one-half bath pool home in Sevilla. Beautifully designed with every thought and consideration the home boasts a very desirable 3-way split floorplan with a downstairs…
Lugano Terrace
$1,374,900
1880 Via Contessa
4 bed / 4 bath Single Family Home
MLS #O5425461
4,343 sq. ft.
Winter Park, FL 32789
THIS SOUTHERN LIVING STYLE POOL HOME BUILT BY POSADA CUSTOM HOMES IS LOADED W/ CHARM. SITUATED ON A QUIET STREET IN THE HEART OF THE PRESTIGIOUS VIAS, THIS HOME HAS THREE FIREPLACES, BEAUTIFUL HARD WOOD FLOORS, FOUR…
Maitland Shores
$839,900
2200 Azalea Place
5 bed / 5 bath Single Family Home
MLS #O5430399
3,774 sq. ft.
Winter Park, FL 32789
Prime Winter Park location just off of Via Tuscany and in close proximity to the Winter Park Racquet Club and Lake Maitland. Home offers 5 bedrooms and 5 baths, hardwood floors throughout first floor, new kitchen and…
Winter Park Village
$799,900
1324 Morton Road
4 bed / 5 bath Single Family Home
MLS #O5426181
3,488 sq. ft.
Winter Park, FL 32789
NEW CONSTRUCTION!!! This spectacular two-story French-Contemporary inspired estate perfectly situated on a cul-de-sac in desirable Winter Park. With captivating curb appeal and allured landscaping, this French flared…
Boiley Green Sub
$4,300,000
1830 Gipson Green Lane
5 bed / 7 bath Single Family Home
MLS #O5427054
6,850 sq. ft.
Winter Park, FL 32789
LUXURY LAKEFRONT LIVING! Privately nestled on Winter Park's Chain of Lakes, this Spectacular Home w/ gated entrance, has it all! Entirely remodeled w/award-winning interior designer, Betsy Godfrey, no attention to…
Douglas Grand Winter Park Residential
$1,699,000
102 S Virginia Avenue #110
3 bed / 4 bath Condo
MLS #O5432184
3,778 sq. ft.
Winter Park, FL 32789
Central Florida's most distinctive, historic and established in-town living experiences. Welcome your guest directly from your own front door located on Virginia Avenue. Sit on your corner covered porch to read the…
Fontainebleau
$639,000
2255 Chantilly Avenue
4 bed / 4 bath Single Family Home
MLS #O5431891
3,289 sq. ft.
Winter Park, FL 32789
JUST REDUCED - MOTIVATED SELLERS! Stunning custom designed four bedroom, three and one half bath home located on one of the most quiet streets in Winter Park! Amazing floor plan with more than 2,900 square feet of…
Douglas Grand Of Winter Park
$1,299,900
101 S New York Avenue #301
3 bed / 4 bath Condo
MLS #O5426014
3,176 sq. ft.
Winter Park, FL 32789
with the opulent finishes you would expect of a luxury residence in the heart of winter park, the douglas grand is one of the finest places to call home. elegant shops and boutiques that line park avenue, direct access…
Penn North
$1,325,000
1008 N Pennsylvania Avenue
4 bed / 5 bath Single Family Home
MLS #O5426166
3,410 sq. ft.
Winter Park, FL 32789
"pre construction to be built". one of four fabulous single family detached homes to be built as a part of a planned development being built in downtown winter park adjacent to the golf course and a short walk to park…
Penn North
$1,325,000
1006 N Pennsylvania Avenue
4 bed / 5 bath Single Family Home
MLS #O5426424
3,410 sq. ft.
Winter Park, FL 32789
"pre construction to be built". one of four fabulous single family detached homes to be built as a part of a planned development being built in downtown winter park adjacent to the golf course and a short walk to park…
Preserve Point/Windsong
$3,450,000
MLS #O5429362
1.48 acres
Winter Park, FL 32789
Located in Windsong on a quiet cul-de-sac only 10 minutes from Downtown Orlando. This lot faces West and overlooks Rollins College. The total square footage of the lot is 64,407 sq. ft. (1.48 acres). There are 5 very…
Maitland Shores First Add
$1,199,000
2525 Via Tuscany
5 bed / 8 bath Single Family Home
MLS #O5435297
4,841 sq. ft.
Winter Park, FL 32789
Huge Price Reduction! This fabulous home with Chain of Lakes Access is situated on a large corner lot in the “Vias”. Built in 2007 with all the modern amenities, warmth & character you would expect. Exceptional…
South Interlachen Place
$2,878,000
125 S Interlachen Avenue #6
3 bed / 5 bath Town Home
MLS #O5432319
4,160 sq. ft.
Winter Park, FL 32789
Under Construction. Only two residences remain! Your opportunity to own unprecedented luxury in the most exclusive area of Winter Park has arrived. South Interlachen Place is around the corner from world famous Park…
$550,000

0 bed / 0 bath Single Family Home
MLS #O5409839
3,230 sq. ft.
Winter Park, FL 32792
An established, on-going six bed assisted living facility located in a quiet neighborhood in Seminole County. Stable patients, competent stable staffing and well executed and budgeted operation yields an immediate…
Maitland Shores
$1,999,900
2219 Venetian Way
5 bed / 6 bath Single Family Home
MLS #O5428074
6,362 sq. ft.
This exclusive William Felkel custom built home has it all in the Winter Park Via's, including a new circular drive. It is a one of a kind 5 br 6 bath, 6,362 sq ft home which has every appointment imaginable! The custom…
Winter Park Old Town
$6,900,000
570 Seminole Drive
Vacant Land
MLS #O5439246
2.25 acres
Winter Park, FL 32789
This 2.25 acre lake front crown jewel is a once-in-a-lifetime offering of one of Old Winter Park’s most prestigious estate lots. Situated high above expansive Lake Osceola and only a short walk from famed Park…
$675,000
241 E Rockwood Way
3 bed / 3 bath Single Family Home
MLS #O5439299
2,608 sq. ft.
Winter Park, FL 32789
JUST REDUCED – Immaculate 3 bedroom, 2.5 baths with an amazing location – walk to the Audubon Park Garden District, Baldwin Park, and even Park Avenue. Beautiful hardwood floors, high ceilings, crown moldings,…
$2,379,000
MLS #O5439527
1.62 acres
Winter Park, FL 32789
Perfect place to build your dream house. Located in Winter Park, this lot abutts Lake Virginia, near shopping A-rated schools, beautiful Lake Baldwin is very near.
Sylvan Lake Shores
$1,795,000
1511 Harris Circle
5 bed / 5 bath Single Family Home
MLS #O5441309
4,224 sq. ft.
Winter Park, FL 32789
Winter Park lakefront, designed like a historic Charleston home with a gated entrance courtyard that is enhanced by lovely gardens and a bubbling fountain. Full balconies along both the front & rear of this spectacular…
Mac Donald Robert Dhu Park
$8,490,000
161 Palmer Avenue
7 bed / 12 bath Single Family Home
MLS #O5436881
17,649 sq. ft.
Winter Park, FL 32789
Welcome to The Winter Park Lakeview Estate, a two-acre, contemporary paradise with panoramic views of Lake Maitland on the Winter Park Chain. Designed by NBA star Horace Grant, expanded by Alan Ginsburg, and featured in…
Waterbridge
$669,000
1327 Bridgeport Drive
5 bed / 4 bath Single Family Home
MLS #O5427689
4,181 sq. ft.
Winter Park, FL 32789
NEW PRICE! Light, bright, open, and airy Winter Park home can be yours! This newly renovated home feeds into the Winter Park school system and is close to shopping, restaurants, and Rollins College. Just steps away from…
Temple Heights
$1,050,000
1361 Palmer Avenue
5 bed / 4 bath Single Family Home
MLS #O5440569
3,559 sq. ft.
Winter Park, FL 32789
NEW PRICE. Walk to Park Avenue, Winter Park YMCA and Phelps Park! Like New Construction/One owner 5/3.5 Mediterranean pool home offers a premier address and a bright and clean feel in the heart of Olde Winter Park. …
$675,000
789 S Pennsylvania Avenue
2 bed / 3 bath Single Family Home
MLS #O5433770
1,921 sq. ft.
Winter Park, FL 32789
Truly inspiring and stunning this two bedroom, two and one-half bath home is straight out of a magazine. Gorgeous hardwood floors, a designer kitchen, customized breakfast nook, and crystal chandeliers – the home is…
Winflor Court
$629,000
700 Dixie Parkway
4 bed / 3 bath Single Family Home
MLS #O5443574
2,214 sq. ft.
Winter Park, FL 32789
Welcome to this wonderful pool home in the Park Grove area! Gorgeous wood floors throughout the formal rooms and all the bedrooms. Lovely trim work and plantation shutters. Great 3 way split bedroom plan with a private…
Canton Avenue Cottages
$749,000
437 N Capen Avenue
3 bed / 3 bath Single Family Home
MLS #T2809288
2,031 sq. ft.
Winter Park, FL 32789
Seller to contribute up to a total of $15,000 towards allowable closing costs with preferred mortgage and title companies. But hurry; closing must occur or before December 29, 2016. This new home community of twelve…
Tantum
$1,395,000
364 Beloit Avenue
3 bed / 4 bath Single Family Home
MLS #O5439629
2,914 sq. ft.
Winter Park, FL 32789
Under Construction - Fabulous new construction in prime downtown location. New construction by Z Properties/IBK Construction will leave no detail overlooked. last of 2 available.
Chantilly Sub
$639,000
1441 Vendome Place
4 bed / 3 bath Single Family Home
MLS #O5443700
3,428 sq. ft.
Winter Park, FL 32789
Beautiful four bedroom, two and one-half bath home in Winter Park. Located on a quiet, tree-lined street, this lovely home features hardwood floors, open living room with fireplace, eat-in kitchen with granite counters…
Mondrian
$589,900
1802 Lee Road
3 bed / 4 bath Town Home
MLS #O5443959
2,276 sq. ft.
Winter Park, FL 32789
Under construction to be built. STUNNING, CONTEMPORARY TOWNHOMES ON LAKE KILLARNEY 3BDRM/3.5 BTHRM END UNIT 2276 sq ft...BOAT DOCKS AVAILABLE 2 STORY TOWNHOUSE W/LARGE BALCONY.... THESE UNITS WILL HAVE…
Mondrian
$539,900
1804 Lee Road
3 bed / 4 bath Town Home
MLS #O5443984
2,157 sq. ft.
Winter Park, FL 32789
UNDER CONSTRUCTION, TO BE BUILT . STUNNING.CONTEMPORARY TOWNHOMES ON LAKE KILLARNEY 3BDRM/3.5 BTHRM 2157 sq ft...BOAT DOCKS AVAILABLE 2 STORY TOWNHOUSE W/LARGE BALCONY.... THESE UNITS WILL HAVE LUXURIOUS,UPGRADED…
Golfview Heights
$1,599,000
1700 Greenwich Avenue
4 bed / 6 bath Single Family Home
MLS #R4704715
4,009 sq. ft.
Winter Park, FL 32789
Under Construction! Original custom home built by Dave Cahill Homes on one of the best corner lots in Winter Park. "Contemporary Mediterranean" style with approximately 4,009 SQFT of living area, Light and Bright Great…
Mondrian
$631,900
1820 Lee Road
3 bed / 4 bath Town Home
MLS #O5444043
2,407 sq. ft.
Winter Park, FL 32789
UNDER CONSTRUCTION NEW TOWNHOUSE CONSTRUCTION WITH HUGE ROOF TOP DECKS AND LAKE VIEWS. . STUNNING CONTEMPORARY TOWNHOMES ON LAKE KILLARNEY 3BDRM/3.5 BTHRM END UNIT 2276 sq ft...BOAT DOCKS AVAILABLE 3 STORY…
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