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Winter Park, FL Real Estate — Homes For Sale in Winter Park, FL

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Winter Park Real Estate Overview

Originally founded as a resort destination by affluent New Englanders in the late 1880s, Winter Park is today known for its majestic trees, beautiful parks, brick-lined streets, stunning homes, a private liberal arts college, educational museums, sparkling lakes, and amazing shops. Winter Park is located just 15 minutes from the...
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$1,450,000
$5,131/mo
Monthly Payment:
$5,131
Principal & Interest:
$5,131
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $290,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 3,862sq ft $375 / sq ft SFR
Lot Size11,081sq ft Built2006 On Site92days
Exquisite Winter Park Custom Pool home features outstanding quality. Impeccably maintained, this 5 Bedroom, 4/2 Bath home will appeal to the most discriminating buyer.... more
Exquisite Winter Park Custom Pool home features outstanding quality. Impeccably maintained, this 5 Bedroom, 4/2 Bath home will appeal to the most discriminating buyer. Reminiscent of Spanish Colonial Architecture, the grand entrance is enhanced by exquisite exterior features including an inviting expansive waterfall, intricate landscaping incorporating winding brick paths. Back patio includes brand new built in grill. The Interior features an inviting open floorplan with seamless flow between formal and casual areas. Design elements include travertine Brazilian wood flooring, trey/coffered 12 ft ceilings, extensive custom ironwork, 8 baseboards, crown molding and stone fireplace. 4 bedrooms and 3.5 bathrooms in the main house. 1st floor master bedroom leads to pool and outdoor living areas through French doors. Master bath is enhanced with stand alone jetted tub. A butler pantry separates the formal dining room from the chefs delight gourmet kitchen. Granite counters with large work areas, stainless steel appliances, breakfast bar and separate eating area are just some of the highlights. The 2nd floor has a large bonus room, 2nd bedroom ensuite plus 2 additional bedrooms with jack and jill bath. Arcaded walkways lead to pool/spa and detached casita featuring a beautiful full bedroom ensuite perfect for guest or nanny quarters. The property runs the width of the street providing the utmost of courtyard privacy. This quaint brick street is convenient to Park Avenue. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
Your search results are current and complete. Learn more
$1,375,000
$4,866/mo
Monthly Payment:
$4,866
Principal & Interest:
$4,866
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $275,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,569sq ft $385 / sq ft SFR
Lot Size9,480sq ft Built2016 On Site95days
Under-construction with september 2016 completion. The first of four fabulous single family detached homes as a part of a planned development being built in downtown winter park... more
Under-construction with september 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 walk to park avenue. This 3,569 sf air-conditioned space (and 5,108 sf built-up) beautiful modern santa barbara style custom home, has been thoughtfully designed by winter park's award wining architect slocum platts, and is being built by experienced winter park builder, feely custom homes. Featuring an elegant, bright and open floor plan with high celeings, you enter the home through an impressive foyer with a 16 foot ceiling leading, on one side, to a guest suite or study/office with it's own private full bath; and on the other side, to the master retreat with 11.4 foot tray ceiling and dual walk-in closets, a spa-like all marble bath with, a free-standing tub, an enclosed w.C with bidet, and a shower. The living area starts with the grand room with 14.4 foot ceilings flowing seamlessly into the dining room area opens to the gourmet kitchen with an island and counter seating, high end appliances and cabinetry; and is open to the gathering room. The double sided gas fireplace is the centerpiece to all of these rooms, which overlook a huge 14 x 35 covered lanai with a summer kitchen. Folding french doors from the lanai make this part of the living space and is ideal for entertaining or dining al fresco. **see attachment for additional remarks featuring the second floor. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$490,000
$2,034/mo
Monthly Payment:
$2,034
Principal & Interest:
$1,734
HOA Dues:
$300
(Based on a 30 year fixed loan at 3.38% with $98,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,354sq ft $208 / sq ft TWN
Lot SizeN/Asq ft Built1989 On Site95days
Spacious and bright 3 bedroom, 2.5 bath townhouse in walking distance of Winter Park shopping and dining on the avenue. Also, it is a short walk to community tennis courts and... more
Spacious and bright 3 bedroom, 2.5 bath townhouse in walking distance of Winter Park shopping and dining on the avenue. Also, it is a short walk to community tennis courts and Rollins College. This townhouse features soaring ceilings and expansive windows. There is a stunning floor to ceiling designer wood display cabinet in the family room. A warm and cozy fireplace centers the room. The large kitchen features eat-in dining and tall cabinets for optimal storage. There is also a separate dining room or office. There are two very private patios for outside enjoyment that belong to the townhouse. The community of four townhouses also has its own private pool in the back. The complex has just completed a large landscaping project. Upstairs you will find an elegant and relaxing master suite with 12 ft high his and hers closets, dual vanities, separate tub and shower. Two other bedrooms with a Jack and Jill bath complete the upstairs. This townhouse is one of four each with a two car garage, community pool and Winter Park schools. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$1,675,000
$7,207/mo
Monthly Payment:
$7,207
Principal & Interest:
$5,927
HOA Dues:
$1,280
(Based on a 30 year fixed loan at 3.38% with $335,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,143sq ft $782 / sq ft CND
Lot Size13,765sq ft Built2008 On Site95days
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... more
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, shops, fine restaurants, wine rooms and sidewalk cafes.This Penthouse condominium is full of surprises and elegant touches of handcrafted architecture and design. The warm and inviting Chef's kitchen is perfect when entertaining guests as it sits adjacent to a spacious living and dining area. As you sit admiring the views of the illuminating gas fireplace, the glass lined walls display peaceful tree-lined images boasting the ambiance of serenity. The private Master Bedroom is designed with a unique his and her bathroom. A shower dressed in glass is shared by two separate private vanity areas. Not only will you witness the awe-inspiring views from the full length balcony, you have the privilege of the panoramic sights from the private roof-top terrace, which is an exclusive amenity of this residence. The quality and charm is unmistakable in this fully dressed Penthouse Suite. less
Listing Provided Courtesy of REGAL R.E. PROFESSIONALS LLC
Popularity
$551,597
$2,035/mo
Monthly Payment:
$2,035
Principal & Interest:
$1,952
HOA Dues:
$83
(Based on a 30 year fixed loan at 3.38% with $110,319 down)
Winter Park, FL 32792
Seminole County School District
4bed 4bath 3,514sq ft $157 / sq ft SFR
Lot SizeN/Asq ft Built2013 On Site97days
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... more
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 throughout home as well as custom painting and detailing. THIS IS A MODEL HOME FOR SALE! Close to downtown Winter Parks charming historical district, residents of Enclave at Aloma take pleasure in a town whose admirable gems include gorgeous Rollins College and the Morse Museum of American Art, home to the worlds largest collection of Tiffany glass. Winter Park, an Old Florida resort business titans founded more than a century ago, is full of excellent boutiques and eateries, upscale art galleries, deluxe golf courses, parks, and historic architecture. Enclave at Aloma Park also sits less than one mile from the GreeneWay (SR 417), putting homeowners within reach of Orlando, the international airport, lakes, theme parks, and, of course, the Sunshine States world-popular beaches. less
Listing Provided Courtesy of STANDARD PACIFIC OF TAMPA
Popularity
$299,900
$1,562/mo
Monthly Payment:
$1,562
Principal & Interest:
$1,061
HOA Dues:
$501
(Based on a 30 year fixed loan at 3.38% with $59,980 down)
Winter Park, FL 32789
Orange County School District
1bed 1bath 1,000sq ft $300 / sq ft CND
Lot SizeN/Asq ft Built1960 On Site97days
Huge price reduction - owner is onto her next home and this one has to go !!! Great opportunity in "whispering waters" - this 1 bed 1 bath 2nd floor condo has been upgraded with... more
Huge price reduction - owner is onto her next home and this one has to go !!! Great opportunity in "whispering waters" - this 1 bed 1 bath 2nd floor condo has been upgraded with pgt vinyl framed, dual glazed, argon gas filled, low e windows and sliders which adds security, energy efficiency and blocks out noise. The unit has an open spacious layout that is light and bright and has all motorized remote controlled custom blinds that can be operated from the comfort of your couch or bed. The building has an elevator so no steps have to be navigated to get to the unit, laundry or underground parking garage. Location is ideal for the person who likes to get out and go down to the lake or browse the shops of park ave which has numerous shops, restaurants and saloons. Best priced unit currently so don't let this one pass by... less
Listing Provided Courtesy of THE TITAN GROUP, INC.
Popularity
$225,000
$796/mo
Monthly Payment:
$796
Principal & Interest:
$796
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $45,000 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
3bed 2bath 1,568sq ft $143 / sq ft SFR
Lot Size14,971sq ft Built1950 On Site98days
New price! Location! Location! Location! Cute winter park cottage ready for you to make it your own! Situated on a quiet dead-end street, just one block away from lake... more
New price! Location! Location! Location! Cute winter park cottage ready for you to make it your own! Situated on a quiet dead-end street, just one block away from lake killarney, this 3 bed home with 2 full baths has a large eat-in kitchen, separate dining room and indoor laundry room. The roof was replaced approx. 9 years ago and home is move-in ready while you plan your renovation projects, maybe to include exposing the original hardwood floors (per owner). Yard is partially fenced and very private, with room for a pool and also includes a storage shed with additional parking pad for rv or truck (no hoa) and another storage area connected to house. Popular residential area, close to killarney elementary school, winter park shopping, dining, entertainment and with easy access to i-4 for beaches, parks and everything that this area has to offer. Call to see today! less
Listing Provided Courtesy of TOLARIS REALTY GROUP LLC
Popularity
$599,000
$2,119/mo
Monthly Payment:
$2,119
Principal & Interest:
$2,119
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $119,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 1,978sq ft $303 / sq ft SFR
Lot Size12,409sq ft Built1988 On Site99days
This beautiful Mediterranean custom home located in charming Winter Park features four bedrooms, two-and-a-half baths and an open floor plan perfect for family living or... more
This beautiful Mediterranean custom home located in charming Winter Park features four bedrooms, two-and-a-half baths and an open floor plan perfect for family living or entertaining. Wood-burning fireplace is located in the family room, which leads out to wonderful views of the covered lanai, pool and spa area, and summer kitchen. The gourmet kitchen has wood cabinets, stainless appliances, a gas cooktop, dark hammered farmhouse sink and a center island. Two-car garage, a private fenced backyard with mature landscaping all throughout the property. Many upgrades were completed by the current sellers. Just minutes away from Park Avenue, Rollins College and local shopping. Additional square footage was added to interior and exterior by current owners. less
Listing Provided Courtesy of PREMIER SOTHEBY'S INT'L REALTY
Popularity
$775,000
$2,742/mo
Monthly Payment:
$2,742
Principal & Interest:
$2,742
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $155,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,773sq ft $279 / sq ft SFR
Lot Size16,985sq ft Built1982 On Site100days
This is a one-of-a-kind home in the lovely via area of winter park. Custom built home has a unique character and charm that typically is not found in central florida. First time... more
This is a one-of-a-kind home in the lovely via area of winter park. Custom built home has a unique character and charm that typically is not found in central florida. First time on the market for many years. If you like character and charm then this home is for you. Anyone who enjoys the easy feeling of a day in the country while living in the city will appreciate the interior of this home. There is no home like this one in all of central florida and it makes me nostalgic for a north carolina cabin. Also located in a sweet cul-de-sac neighborhood that reeks of charm and quintessential winter park vibe. Great a-rated schools are an added bonus. The master bedroom is the only room upstairs with a fireplace and vaulted ceilings and recently renovated master bath. Updated kitchen and lots of flex space in this home. 2450 via sienna will appeal to someone who likes the french country style with lots of wood and a million ways to decorate. Oversized yard is inviting with towering oaks and private garden spaces. Downstairs has three bedrooms although one bedroom can be used for a giant media/family room. So many options in this super luscious home and i know it will appeal to the creative buyer with a sense of style and who knows quality. I hope that person is you! less
Listing Provided Courtesy of CHARLES RUTENBERG REALTY
Popularity
$629,000
$2,259/mo
Monthly Payment:
$2,259
Principal & Interest:
$2,226
HOA Dues:
$33
(Based on a 30 year fixed loan at 3.38% with $125,800 down)
Winter Park, FL 32792
Seminole County School District
4bed 3bath 3,287sq ft $191 / sq ft SFR
Lot Size1.2acre Built1986 On Site102days
Back on market. Buyer financing fell through, don''t miss this chance.Come home to your private oasis in the sought out Bear Gully Bay! This lakefront home greets you with its... more
Back on market. Buyer financing fell through, don''t miss this chance.Come home to your private oasis in the sought out Bear Gully Bay! This lakefront home greets you with its large front porch to give you an old Florida living feel. Open the front door and walk into your foyer with beautiful wood flooring. Straight ahead you large family room with a spectacular view of the lake. The gourmet kitchen opens to your family room with granite countertops, travertine flooring, island, wood cabinets with lighting, pantry,breakfast bar and breakfast nook with picture window. The master suite bathroom will melt the day away with a spa tub sitting under stained glass window. His and Her vanity sinks with granite and walk in shower stall complete this bathroom remodel. Additional storage? Not a problem! The attic flooring has been installed for extra storage & cabinetry has been added to the garage for organization. The Florida room is meant to be enjoyed by all year round with all glass windows floor to ceiling. Double slider doors open to your paver patio area intended easy entertaining and backyard bbq's. Work on your summer tan with very own private "backyard beach". Boater will be delighted to know there is a deeded boat dock & boat lift. Enjoy water sports in the summer with boating, tubing or skiing. Take the kayak or paddle board out and connect to smaller lakes and Econ River. This spring fed ski lake is residence access and the association maintains the bass population for the fisherman in the family. less
Listing Provided Courtesy of KELLER WILLIAMS AT THE PARKS
Popularity
$270,000
$998/mo
Monthly Payment:
$998
Principal & Interest:
$955
HOA Dues:
$43
(Based on a 30 year fixed loan at 3.38% with $54,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,587sq ft $170 / sq ft SFR
Lot Size5,846sq ft Built1992 On Site102days
Beautiful 3 bedroom home, your wait is over! This home has everything you're looking for! Tile Throughout the house, fully renovated kitchen, new a/c, new light fixtures,... more
Beautiful 3 bedroom home, your wait is over! This home has everything you're looking for! Tile Throughout the house, fully renovated kitchen, new a/c, new light fixtures, beautifully done fireplace, all new paint on the inside and out! Come see this house today and make it your home. less
Listing Provided Courtesy of ODRY VARGAS REALTY GROUP
Popularity
$849,000
$3,007/mo
Monthly Payment:
$3,007
Principal & Interest:
$3,004
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.38% with $169,800 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 2,966sq ft $286 / sq ft SFR
Lot Size11,885sq ft Built1960 On Site103days
Wonderfully renovated home in the sought after quiet neighborhood of Timberlane Shores. This four bedroom, three and a half bath sun filled home has been designed for indoor and... more
Wonderfully renovated home in the sought after quiet neighborhood of Timberlane Shores. This four bedroom, three and a half bath sun filled home has been designed for indoor and outdoor living and is perfect for family gatherings and entertaining both inside and out. Gourmet cooking in a new custom outdoor kitchen as well as in indoor kitchen fitted with all the extras. Some of this home's many features include hardwood floors, all new windows, Kohler fixtures, new mahogany exterior doors, new interior doors, and storage throughout. The fining room and kitchen have a two way wood burning fireplace. Three bathrooms have been completely re-plumbed and one half bath has been added. Private master retreat features a built-in storage entertainment center and a custom walk in closet. Enjoy entertaining in the backyard. The pool has been resurfaced with an added travertine deck and saltwater system, rotisserie grill, fridge and sink. Both the location and flexible floor plan offers the best of Winter Park living. Top A rated schools, convenient to all Winter Park amenities, parks and downtown area. You have to see this home to believe all that it has to offer. This home will not last, schedule a showing today. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$3,995,000
$14,138/mo
Monthly Payment:
$14,138
Principal & Interest:
$14,138
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $799,000 down)
Winter Park, FL 32789
Virginia Heights Orange County School District
5bed 7bath 6,323sq ft $632 / sq ft SFR
Lot Size19,960sq ft Built2008 On Site103days
2008 Parade Home was the recipient of numerous awards, built by renowned architect Phil Kean. This expansive estate boasts an indoor/outdoor lifestyle surrounded by a custom... more
2008 Parade Home was the recipient of numerous awards, built by renowned architect Phil Kean. This expansive estate boasts an indoor/outdoor lifestyle surrounded by a custom concrete wall trimmed with brick offering complete privacy. Stunning Iron gate opens to a custom Mahogany door which leads the way to private casita & pool/lanai area. As you enter the lavish foyer you will be captivated with the level of elegance and opulence. Home boast 5 en-suite, 2 half baths, 2 kitchens, state of the art media room, spa with sauna, custom office, bonus rm, exercise area & balcony. The main kitchen features a mosaic barrel ceiling, ebony rifted oak cabinets, custom coral stone walls & back splash, 2 sub-zero refrig., 2 conv ovens, a pizza oven, natural gas Wolf cook top, ice maker and vegetable steamer. Hidden walk-in pantry, solid sandstone & nickel hood, plus granite counters complete this spectacular kitchen. The 2nd kitchen is fully equipped. The master retreat offers a spa-like bathroom with steam shower, his & her water closets, custom floor to ceiling closet, 2 sided fireplace, sitting room with 80"TV, refrigerator & access to lanai. The interior blends seamlessly to the exterior creating another level for entertaining! Additional amenities: Elevator, Wine Room, Custom heated pool, Automatic screens, Dbl pane Hurd windows, Generator, Solar power for H20, Crestron Audio system with wall panels to control 15 security cameras & Lutron Lighting with ipad's. Gated driveway with 3 garages & capacity for 5 cars. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$699,900
$2,479/mo
Monthly Payment:
$2,479
Principal & Interest:
$2,476
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.38% with $139,980 down)
Winter Park, FL 32789
Orange County School District
5bed 3bath 3,477sq ft $201 / sq ft SFR
Lot Size15,311sq ft Built1958 On Site103days
Check out this great home in Winter Park today! This 2 story home features a first floor master suite and 2 additional bedrooms downstairs. There are 3 rooms upstairs which... more
Check out this great home in Winter Park today! This 2 story home features a first floor master suite and 2 additional bedrooms downstairs. There are 3 rooms upstairs which offers flexibility for any buyer! The renovated kitchen opens to the dining room for easy access. This home is on an over sized lot with plenty of room in the backyard to meet any of your needs! It is conveniently located near Baldwin Park, plenty shopping and restaurants and is zoned for Winter Park schools. Don't miss an opportunity to check out this home today! less
Listing Provided Courtesy of RE/MAX OPTIMA
Popularity
$929,500
$3,397/mo
Monthly Payment:
$3,397
Principal & Interest:
$3,289
HOA Dues:
$108
(Based on a 30 year fixed loan at 3.38% with $185,900 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 3,462sq ft $268 / sq ft SFR
Lot Size10,905sq ft Built2004 On Site104days
Immaculate, traditional 1 owner home situated on prime lot in charming Pennsylvania Place. Located in the heart of olde Winter Park just blocks from Park Avenue. Built in 2004... more
Immaculate, traditional 1 owner home situated on prime lot in charming Pennsylvania Place. Located in the heart of olde Winter Park just blocks from Park Avenue. Built in 2004 and meticulously maintained & upgraded. Spacious downstairs master suite including gorgeous bath with garden tub, separate shower and 2 custom walk-in closets. Office or additional bedroom + full bath downstairs. Dining room & living room with natural gas fireplace overlook beautiful park like setting off your covered back porch. Huge kitchen with abundant designer cabinetry, stainless appliances, gas cooktop, giant walk in pantry, & breakfast room all open to large family room with built-ins and French doors for entertaining. Upstairs houses 3 additional bedrooms/2 baths plus a bonus room and tons of storage. Additional features include hardwood floors, crown molding, plantation shutters, pavers, wrought iron fencing, 10' ceilings, designer light fixtures, large indoor laundry, rear entry garage, central vacuum, double pane windows, whole house audio system, security system & much more! less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
16 17 18 19 20 21 22 23 24 ... 29
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Local real estate services provided by:
Coldwell Banker Residential Real Estate
Coldwell Banker Residential Real Estate
5951 Cattleridge Ave
Sarasota, FL 34232

844.662.5638
Website provided and owned by Coldwell Banker Residential Real Estate.
 
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Data last updated: Monday, May 30, 2016 at 1:40 PM. Properties in listings may have been sold or may no longer be available.