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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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$1,050,000
$3,890/mo
Monthly Payment:
$3,890
Principal & Interest:
$3,890
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $210,000 down)
Winter Park, FL 32792
Orange County School District
6bed 4bath 5,449sq ft $193 / sq ft SFR
Lot Size20,128sq ft Built2000 On Site54days
Priced $200,000 below appraisal! Our loss is your gain! Nestled in desirable winter park, come home to your own private oasis! Sprawling oak trees and a sweeping landscape... more
Priced $200,000 below appraisal! Our loss is your gain! Nestled in desirable winter park, come home to your own private oasis! Sprawling oak trees and a sweeping landscape welcome you to this 6 bed/4 bath 2-story custom home on a premium 1/2 acre lot. step in through the front door and fall in love with the soaring cathedral ceilings and stunning floor-to-ceiling glass windows that flood the elegant living room with natural light. This spacious beauty also boasts 2 master suites (one on each floor) and a separate 2-bedroom first floor suite perfect for in-laws or an extended family! the first floor bedrooms open up to a private deck with a hot tub where you can relax in comfort under the stars. Or if you're feeling like entertaining, host a spectacular party in your expansive back yard! Back inside, enjoy the views of your garden or catch a cardinal or blue-jay flying by while making breakfast in your bright, open kitchen or while unwinding in the family room. Upstairs you'll find three bedrooms, including the second master suite all with private balconies! A den/library & large bonus room complete the second floor. entry and exit are easy in your oversized garage, thanks to double doors that open on both sides. When you're ready to leave, nearby shopping & restaurants abound, including the world-class shops and restaurants of park avenue! Plus, convenient to wp hospital, ymca, whole foods, phelps park & interlachen country club; along with a-rated schools. call today for a private showing! less
Listing Provided Courtesy of Keller Williams Heritage Rlty
Popularity
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$365,000
$1,352/mo
Monthly Payment:
$1,352
Principal & Interest:
$1,352
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $73,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 1,705sq ft $214 / sq ft SFR
Lot Size4,908sq ft Built1926 On Site55days
Renovated completely! This 1926 Winter Park Bungalow offers today’s comforts with yesterday’s charm. Refinished hardwood floors throughout. Three bedrooms upstairs... more
Renovated completely! This 1926 Winter Park Bungalow offers today’s comforts with yesterday’s charm. Refinished hardwood floors throughout. Three bedrooms upstairs are the perfect place to find rest & relaxation. The Master Suite is large and one of the other bedrooms upstairs can be used as an office, library or nursery. Upstairs bathroom was recently remodeled with a new shower, tile, and more! Light and bright kitchen offers counter bar seating, all appliances and cabinetry – all open to the Sun Room with French doors overlooking the courtyard and patio. Detached Guest Suite also remodeled – new metal roof, doors, windows and separate A/C! Many, many more upgrades! You will love the feel and style of this impeccably maintained home! Call today for your private showing! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$369,900
$1,370/mo
Monthly Payment:
$1,370
Principal & Interest:
$1,370
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $73,980 down)
Winter Park, FL 32792
Orange County School District
5bed 3bath 2,990sq ft $124 / sq ft SFR
Lot Size8,282sq ft Built1991 On Site55days
Well Maintained and Move In Ready. This 5 bedroom, 3 bath, spacious home is located on a private, low traffic cul-de-sac. The home has a very open floor plan with vaulted... more
Well Maintained and Move In Ready. This 5 bedroom, 3 bath, spacious home is located on a private, low traffic cul-de-sac. The home has a very open floor plan with vaulted ceilings. Kitchen has granite and a large breakfast bar overlooking the great room. Wood burning fireplace in the great room. The master and one other bedroom are down stairs. There are three large bedrooms and a loft upstairs. Enjoy your private completely fenced back yard from the covered and screened lanai. The home has been re-plumbed. Truly well maintained and shows well! WINTER PARK HIGH School District. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$395,000
$1,463/mo
Monthly Payment:
$1,463
Principal & Interest:
$1,463
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $79,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,513sq ft $157 / sq ft SFR
Lot Size9,771sq ft Built1954 On Site55days
Live big on burks circle in this updated 2513 sf one level home with an open floor plan and four bedrooms plus an office or 5th bedroom! Sleek kitchen with black granite,... more
Live big on burks circle in this updated 2513 sf one level home with an open floor plan and four bedrooms plus an office or 5th bedroom! Sleek kitchen with black granite, stainless appliances and maple cabinets. Large master suite has a nice bath with a jetted soaking tub, double vanities, double headed shower and huge walk in closet. The master and living area open onto a wonderful deck for backyard entertaining. Open kitchen, dining and living areas and a split bedroom plan with two other full baths beautifully redone in 2012. A-rated schools, and all in 32789. Neat as a pin, freshly painted and move in ready this home is in a most convenient location near schools, hospital, restaurants and the lovely windsong community of winter park. This is the perfect starter home for a young family or a superb downsize home for the empty nester with plenty of room for guests and space for entertaining. Make it yours and have great location, good schools and a fun open home for living the winter park lifestyle. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$214,800
$795/mo
Monthly Payment:
$795
Principal & Interest:
$795
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $42,960 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
4bed 2bath 1,786sq ft $120 / sq ft SFR
Lot Size9,495sq ft Built1977 On Site56days
Location, location, location! Zoned for three a schools in seminole county. Winter park address with no hoa fees, a must see, make this your home sweet home. Not a short-sale or... more
Location, location, location! Zoned for three a schools in seminole county. Winter park address with no hoa fees, a must see, make this your home sweet home. Not a short-sale or a bank owned. This beautiful home has new ac 3 years old (2012) and new roof 8 years old (2006). Don't miss this opportunity to own a 4 bedroom 2 bath home with a bonus room that can be used as an office/den/study or as a 5th bedroom in the desirable winter park area. Enjoy barbeques and parties with family and friends in this amazing, oversized and newer fenced back-yard. Eastbrook elementary is 2 blocks away, close to shopping centers, entertainment just minutes from winter park villages. Easy access to mayor express highways and main roads. All fees and measurements needs to be verified by the buyer. Please submit your offer on an as is contract today!! less
Listing Provided Courtesy of Luxury Realty, Inc.
Popularity
$419,000
$1,552/mo
Monthly Payment:
$1,552
Principal & Interest:
$1,552
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $83,800 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,221sq ft $189 / sq ft SFR
Lot Size12,764sq ft Built1956 On Site56days
Owners have loved this home for many years and you will feel the warmth from the moment you walk into the front door. Extremely clean and well maintained, and located in one of... more
Owners have loved this home for many years and you will feel the warmth from the moment you walk into the front door. Extremely clean and well maintained, and located in one of Winter Parks most established neighborhoods. Roof was replaced in 2009 with 30 year architectural shingles. Entire house was re-plumbed last year, most of the windows have been replaced with double pane glass. Inside and outside electrical panels were recently replaced and 4 ton air conditioning unit is only a few years new. One of the few homes in this price range with a two car garage and inside laundry room. Kitchen has been remodeled and has granite countertops, wood cabinets, under cabinet lighting and a bonus walk in pantry! The focal point of this home is located in the living room where there is a stunning fireplace surrounded by Italian Granite. The landing on the fireplace is also granite. So light and bright in the living and family room. Overlooks an amazing and heavily landscaped fenced back yard. The back yard is so tranquil and beautiful you will immediately feel at home. This home has a sprinkler system, surround sound, walk in closets in bedrooms, electrical outlets replaced, interior doors replaced, built in shelving in master bed closet, replaced garage door. Top schools in Orange County. Close to Baldwin Park restaurants and shopping, downtown Orlando and Park Avenue. Excellent central location for easy access around our City Beautiful! less
Listing Provided Courtesy of Keller Williams Advantage 2
Popularity
$369,900
$1,557/mo
Monthly Payment:
$1,557
Principal & Interest:
$1,370
HOA Dues:
$187
(Based on a 30 year fixed loan at 3.75% with $73,980 down)
Winter Park, FL 32789
3bed 2bath 1,900sq ft $195 / sq ft CND
Lot Size2,024sq ft Built1979 On Site56days
Beautiful 3 bedroom 2 bath condo tucked away in the trees in beautiful Winter Park. Hardwood floors, updated kitchen with granite, crown molding, fireplace and more. Small... more
Beautiful 3 bedroom 2 bath condo tucked away in the trees in beautiful Winter Park. Hardwood floors, updated kitchen with granite, crown molding, fireplace and more. Small complex of 4 units total 2 on each side overlooking private courtyard. 2 car garage, walk to Winter Park. A+ Schools! Tour today! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$1,595,000
$5,957/mo
Monthly Payment:
$5,957
Principal & Interest:
$5,909
HOA Dues:
$48
(Based on a 30 year fixed loan at 3.75% with $319,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 5,954sq ft $268 / sq ft SFR
Lot Size17,171sq ft Built2006 On Site56days
Elegant 5 or 6 BE custom home on quiet cul-de-sac brick street. Deeded access to WP Chain of Lakes with neighborhood ramp and park. Terrific entertaining home w/ bright open... more
Elegant 5 or 6 BE custom home on quiet cul-de-sac brick street. Deeded access to WP Chain of Lakes with neighborhood ramp and park. Terrific entertaining home w/ bright open floor plan, generous room sizes, layered crown moldings, volume ceilings, theater and surround sound, decorative lighting, 5 fireplaces, mahogany French doors, plantation shutters, solid Brazilian cherry floors, 2 tankless water heaters, central vac & more... Spacious Master down w/ sitting/exercise rm & adjacent library/home office & 4 more bedroom suites upstairs plus 2 bonus/media rooms and wet bar. Chef's island kitchen featuring gorgeous hand crafted cabinetry, granite countertops with Viking appliances, 2 dishwashers, 2 sinks, 48" built in refrigerator, 6 burner gas range, 2 ovens, warming drawer, wine bar, large walk in pantry, counter w/ rm for 5 barstools and breakfast rm all open to a wonderful large gathering room w/ soaring ceilings & built-ins, separate formal living and dining rooms and great storage... Tremendous outdoor living, private fenced yard, multiple covered porches, putting green, brick and travertine patios, saltwater pool with fountain features, separate patio with outdoor fireplace, circular cobblestone driveway, oversize "4 CAR GARAGE", lush tropical landscaping with towering oaks, whole house gas generator, oversize lot... and walking distance to WPRC, City of WP playground... less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$249,900
$925/mo
Monthly Payment:
$925
Principal & Interest:
$925
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $49,980 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,586sq ft $158 / sq ft SFR
Lot Size9,294sq ft Built1955 On Site56days
Cute 3 bedroom 2 bath Winter Park home close to Dog Park, YMCA, and Baldwin Park. Winter Park A+ schools. Beautiful new kitchen and baths, hardwood floors, large family room and... more
Cute 3 bedroom 2 bath Winter Park home close to Dog Park, YMCA, and Baldwin Park. Winter Park A+ schools. Beautiful new kitchen and baths, hardwood floors, large family room and yard. Move in today! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$69,900
$272/mo
Monthly Payment:
$272
Principal & Interest:
$258
HOA Dues:
$14
(Based on a 30 year fixed loan at 3.75% with $13,980 down)
Winter Park, FL 32789
Orange County School District
1bed 1bath 645sq ft $108 / sq ft CND
Lot SizeN/Asq ft Built1969 On Site56days
Great location! Well maintained, quaint condo overlooking the courtyard. Walk to the back of the building and find the community pool overlooking lake killarney. Walking... more
Great location! Well maintained, quaint condo overlooking the courtyard. Walk to the back of the building and find the community pool overlooking lake killarney. Walking distance to shopping restaurants and more! A must see! less
Listing Provided Courtesy of Don Asher & Associates, Inc.
Popularity
$2,250,000
$8,336/mo
Monthly Payment:
$8,336
Principal & Interest:
$8,336
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $450,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 5,410sq ft $416 / sq ft SFR
Lot Size26,421sq ft Built1992 On Site56days
A contemporary one-of-a-kind work of art located on over half an acre in the heart of the Via’s. This one owner, custom built paradise is light, bright and incredibly... more
A contemporary one-of-a-kind work of art located on over half an acre in the heart of the Via’s. This one owner, custom built paradise is light, bright and incredibly open with soaring ceilings and hand crafted skylights that create the feeling of bringing the outside IN. Large, accommodating living spaces are perfect for entertaining, replete with dining room, living room, kitchen open to family room with fantastic bar area, all overlooking tropical outdoor oasis with covered and screened patios, beautiful pool, and backyard. This one story home is a split plan with spacious private master suite with extra sitting room and luxurious bath. 3 additional bedroom suites with full baths + extra office. Gourmet kitchen with island and breakfast nook. Additional features include extensive crown molding and built-ins, 3 car garage, 4 AC units - all 4 years new, new roof 2014, 2 wine coolers, whole house generator. “A” rated schools include Dommerich Elementary, Maitland Middle and Winter Park High. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$1,199,000
$4,442/mo
Monthly Payment:
$4,442
Principal & Interest:
$4,442
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $239,800 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 3,619sq ft $331 / sq ft SFR
Lot Size12,002sq ft Built2015 On Site57days
Hurry in for this brand new david weekley home in timberlane shores. Come enjoy this spacious 2 story home in the heart of winter park. This beautifully designed and appointed... more
Hurry in for this brand new david weekley home in timberlane shores. Come enjoy this spacious 2 story home in the heart of winter park. This beautifully designed and appointed home has plenty of space with its 5 bedrooms, 4.5 baths, study, bonus room, covered lanai, outdoor kitchen, pool and plenty of storage space. It also boasts the newest david weekley "energy saver" construction science that used double pane/low-e ii vinyl windows, seer 14 a/c system, r-38 blown fiberglass insulation and many other energy-saving features. You will enjoy living among such timeless and elegant upgrades as distressed hardwood flooring that extends throughout the main living spaces and into the owners retreat; full overlay, glazed and raised panel cabinets with crown moulding and beveled knobs in the kitchen and bathrooms and electrical pre-wiring for wall mounted interior electronics. This home is destined to truly enhance the lives of its future owners. Our energy saver homes offer homebuyers the best in energy-efficiency and are backed by our program's heating and cooling energy usage guarantee. These homes are friendlier to you, the environment and your pocketbook! less
Listing Provided Courtesy of Weekley Homes Realty Company
Popularity
$179,900
$991/mo
Monthly Payment:
$991
Principal & Interest:
$666
HOA Dues:
$325
(Based on a 30 year fixed loan at 3.75% with $35,980 down)
Winter Park, FL 32789
2bed 2bath 1,204sq ft $149 / sq ft CND
Lot Size2,743sq ft Built1981 On Site57days
Remarkable unit in wonderful Winter Park.Huntington Court is a quiet, and secluded little street in the most central of downtown Winter Park. Within easy walking distance of... more
Remarkable unit in wonderful Winter Park.Huntington Court is a quiet, and secluded little street in the most central of downtown Winter Park. Within easy walking distance of nearby parks, restaurants, and local shops you cannot do wrong with this location! This safe and charming neighborhood is perfect for any buyer looking to enjoy a very lively area while having the option of quiet and solitude. With 2 bedrooms both with lofts, and 2 and a half bath, stunning hardwood floors throughout the house, all major kitchen appliances, large open and airy rooms, a master bedroom with a scenic patio view, a loft for privacy or extra storage, and many windows, which allow lots of natural light into the home. The exterior space has a picturesque private back patio; perfect for Florida style entertaining. Don’t miss out on this fantastic opportunity to own a wonderful and very affordable home in Winter Park. THis unit has a beautiful fireplace, hardwood floors, and a stunning patio area for enjoying the outdoors without all the yardwork that goes with a large yard. This unit needs a bit of cosmetic attention, but is in super condition. Show and sell today. Live the Winter Park lifestyle! less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
$69,900
$573/mo
Monthly Payment:
$573
Principal & Interest:
$258
HOA Dues:
$315
(Based on a 30 year fixed loan at 3.75% with $13,980 down)
Winter Park, FL 32792
Seminole County School District
2bed 2bath 953sq ft $73 / sq ft CND
Lot Size940sq ft Built1973 On Site57days
You've found it!! Be ready to make this 2 bedroom, 2 bathroom condo in The Stratford in Winter Park HOME! The ground floor unit has a sliding glass door leading to the covered... more
You've found it!! Be ready to make this 2 bedroom, 2 bathroom condo in The Stratford in Winter Park HOME! The ground floor unit has a sliding glass door leading to the covered patio- a perfect place to relax with your cup of coffee to start the day! Inside, the floor plan offers a spacious Master Bedroom with an attached bathroom, a large sized second Bedroom, wood laminate and ceramic tile flooring, new Kitchen cabinets, freshly painted interior and more! All of this plus community amenities including a pool, tennis court, clubhouse and picnic area. This is a Freddie Mac Property. Please see attachments for instructions on submitting offers and information on Freddie Mac First Look Initiative. This property is eligible under the Freddie Mac First Look Initiative through June 22, 2015. An Affidavit of Owner-Occupancy signed by the purchaser and selling agent is required in the contract package if an offer was accepted during the initiative’s 20-day window. This is an acknowledgment that the purchaser intends to occupy the property as purchaser’s primary residence. No investor offers will be considered within the 20-day Freddie Mac First Look Initiative. The Seller is offering a “HomeSteps Financing” product for qualified purchasers. Please see the attached flyer for additional information. ***25% Rental Cap Already Met - Purchaser MUST be OWN OCC!!**** less
Listing Provided Courtesy of Century 21 Roo Realty
Popularity
$239,000
$885/mo
Monthly Payment:
$885
Principal & Interest:
$885
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $47,800 down)
Winter Park, FL 32792
Orange County School District
4bed 3bath 2,040sq ft $117 / sq ft SFR
Lot Size8,998sq ft Built1964 On Site58days
Come explore the possibilities of this spacious 4 bedroom 2.5 bathroom home, located near all downtown Winter Park has to offer. Great shopping, dining and entertainment are... more
Come explore the possibilities of this spacious 4 bedroom 2.5 bathroom home, located near all downtown Winter Park has to offer. Great shopping, dining and entertainment are just a short trip away. Located less than 3 miles from Winter Park Hospital and Rollins College as well. With just a bit more work this home's full potential could be realized. Most of the major renovating has already been done. New laminate flooring and tile in main living areas. New cabinets and granite counter tops in kitchen and bathrooms. New carpet in bedrooms. New central a/c. Most of the light fixtures and ceilings fans have been replaced. The modern open layout in the main living area allows for lots of natural light. The large size of the bonus room has so much potential just in itself. Keep it as a 4th bedroom or maybe make it a family room or game room, just use your imagination. ALL MEASUREMENTS ARE APPROXIMATE AND SHOULD BE VERIFIED BY BUYER. Submit all offers on FAR/BAR ASIS-3 less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
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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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The information being provided by Mid-Florida Regional Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Mid-Florida Regional Multiple Listing Service. Coldwell Banker Residential Real Estate is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Coldwell Banker Residential Real Estate, a broker participant of Mid-Florida Regional Multiple Listing Service. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site.

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Data last updated: Wednesday, July 29, 2015 at 4:29 AM. Properties in listings may have been sold or may no longer be available.