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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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$1,299,000
$4,812/mo
Monthly Payment:
$4,812
Principal & Interest:
$4,812
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $259,800 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 3,753sq ft $346 / sq ft SFR
Lot Size13,234sq ft Built1991 On Site94days
Stunning 4 bedroom 4 1/2 bath home with a separate study/den that could be a 5th bedroom. This home is in a prime Via location on one of the most desirable streets in Winter... more
Stunning 4 bedroom 4 1/2 bath home with a separate study/den that could be a 5th bedroom. This home is in a prime Via location on one of the most desirable streets in Winter Park. This gorgeous home has been updated with top of the line finishes; Bamboo flooring, hardwood, marble, crown molding, plantation shutters throughout, stainless gas appliances, granite countertops and much more. The private master suite is downstairs on the 1st floor and features a very large walk in closet with organizers and large master bath. Upstairs are 3 additional bedrooms, which one can be another large master suite or bonus room. This home has lots of closets and storage throughout. New gourmet kitchen with gas and large eat in area, and family room all overlooking private fenced yard and beautiful pool with pavers and stone. Separate 2 car detached garage with 1/2 bath and summer kitchen for entertaining. Roof is 2 1/2 years, 3 A/C's (2 new), new tankless hot water heater and pool heater and more. Walk to Winter Park Racquet Club. This is a quality home with Winter Parks A+ Schools. Dommerich Elementary, Maitland Middle, and Winter High School. Come view this home today! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
We show you every available listing. Here's how
$725,000
$2,686/mo
Monthly Payment:
$2,686
Principal & Interest:
$2,686
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $145,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,555sq ft $284 / sq ft SFR
Lot Size10,999sq ft Built1973 On Site95days
Location is everything! Priced to sell by motivated seller, this 2,555-square-foot home with private, rear-entry 600-square-foot two-car garage presents a rare opportunity to... more
Location is everything! Priced to sell by motivated seller, this 2,555-square-foot home with private, rear-entry 600-square-foot two-car garage presents a rare opportunity to live on a quiet tree-lined brick street in one of Winter Park's most desirable neighborhoods. Located near the museums, shops, and restaurants of downtown Winter Park and Park Avenue, the Winter Park Country Club, the Winter Park Racquet Club, and the popular lakeside Kraft Azalea Gardens, this traditional two-story home has 3 (or 4) bedrooms and 2.5 baths, with formal living and dining rooms, a family room with custom-milled coffered ceiling, and a master bedroom suite with seating area and a large, room-sized walk-in closet with custom-designed and built cabinetry. Additional outstanding features include Wood-mode custom cabinets and granite countertops in the kitchen, a Travertine marble and granite guest bathroom, Sunburst plantation shutters throughout, Pella double-pane low-E windows, deep crown molding in every room, Brazilian hardwood and Saltillo tile flooring, a Diamond Brite in-ground pool complemented by an adjacent large, raised patio with Sundek coating, a private fenced backyard, and professional landscaping complemented by custom lighting and automatic, zoned landscape irrigation/sprinkler system. This home offers an exceptional chance to live in Winter Park’s very special Golden Triangle – come see for yourself! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$134,900
$499/mo
Monthly Payment:
$499
Principal & Interest:
$499
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $26,980 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
3bed 2bath 1,540sq ft $88 / sq ft SFR
Lot Size9,264sq ft Built1962 On Site95days
Charming Colonial style home located in the Eastbrook subdivision of Winter Park. Great curb appeal with the classic column front and entry. The kitchen features a dinette area.... more
Charming Colonial style home located in the Eastbrook subdivision of Winter Park. Great curb appeal with the classic column front and entry. The kitchen features a dinette area. Inside you have a formal living room adjacent to the family room which will lead you out the sliding glass doors to the private fenced backyard and covered patio areas. The three bedrooms are located upstairs with a full bath. Conveniently located near Full Sail, UCF, and Downtown Orlando. Easy access to major highways. This is a Fannie Mae HomePath property! less
Listing Provided Courtesy of Re/max Town & Country Realty
Popularity
$63,300
$234/mo
Monthly Payment:
$234
Principal & Interest:
$234
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $12,660 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 1,085sq ft $58 / sq ft CND
Lot Size5,644sq ft Built1974 On Site96days
2 bedroom 1.5 baths unit recently been updated with new carpet, paint, upgraded tile in the baths, a newer AC unit and water heater are just some of the features that make this... more
2 bedroom 1.5 baths unit recently been updated with new carpet, paint, upgraded tile in the baths, a newer AC unit and water heater are just some of the features that make this property a great deal for an investor or student. Property is walking distance to Full Sail and just a short commute to UCF and Valencia. less
Listing Provided Courtesy of Jr Kroll Realty
Popularity
$337,000
$1,248/mo
Monthly Payment:
$1,248
Principal & Interest:
$1,248
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $67,400 down)
Winter Park, FL 32792
Orange County School District
3bed 3bath 1,927sq ft $175 / sq ft TWN
Lot Size8,532sq ft Built2014 On Site96days
Open Sun Aug 2, 2pm-4pm
Brand new, stylish 1,927 sq ft 3 bedroom, 2.5 bath front unit town-home in an established and highly desirable area of Winter Park! Town-home features wood & laminate flooring... more
Brand new, stylish 1,927 sq ft 3 bedroom, 2.5 bath front unit town-home in an established and highly desirable area of Winter Park! Town-home features wood & laminate flooring throughout, downstairs bonus room, downstairs utility room, 2nd floor sun deck/terrace perfect for a Jacuzzi, outside entertaining or observing the night sky, cement patio on 1st floor, 42" high European style kitchen cabinets with granite counter-tops, stainless steel appliances and community green spaces. Enjoy living near Cady Way and Ward Parks, top rated Winter Park schools, Winter Park Hospital, Whole Foods and all of the local venues near Aloma and Lakemont Avenue. Near Rollins, UCF and Full Sail University. Front unit located on the right of the building. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$337,000
$1,248/mo
Monthly Payment:
$1,248
Principal & Interest:
$1,248
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $67,400 down)
Winter Park, FL 32792
Orange County School District
3bed 3bath 1,927sq ft $175 / sq ft TWN
Lot Size9,093sq ft Built2014 On Site96days
Open Sun Aug 2, 2pm-4pm
Brand new, stylish 1,927 sq ft three bedroom, two and one half bath front unit townhome in an established and highly desirable area of Winter Park! Townhome features wood &... more
Brand new, stylish 1,927 sq ft three bedroom, two and one half bath front unit townhome in an established and highly desirable area of Winter Park! Townhome features wood & laminate flooring throughout, downstairs bonus room, downstairs utility room, 2nd floor sun deck/terrace perfect for a Jacuzzi, outside entertaining or observing the night sky, cement patio on 1st floor, 42" high European style kitchen cabinets with granite counter-tops, stainless steel appliances and community green spaces. Enjoy living near Cady Way and Ward Parks, top rated Winter Park schools, Winter Park Hospital, Whole Foods and all of the local venues near Aloma and Lakemont Avenue. Near Rollins, UCF and Full Sail University. *Lot size, parcel ID and legal description subject to change once the two units in the building are individually recorded in Orange County. Front unit located on the left of the building. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$600,000
$2,222/mo
Monthly Payment:
$2,222
Principal & Interest:
$2,222
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $120,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size1.3acre BuiltN/A On Site96days
Lot size now 1.35 acres. Seller financing an option - Rare opportunity to find 1.35 acres of Olde Florida charm with 100 ft of lake front on Lake Temple - IN Winter Park city... more
Lot size now 1.35 acres. Seller financing an option - Rare opportunity to find 1.35 acres of Olde Florida charm with 100 ft of lake front on Lake Temple - IN Winter Park city limits. Towering oaks, spanish moss and citrus trees dot the property. Value is in the land but a house and separate studio/guest house on property are ready to put your own touches on, or tear down and build your own lake front dream home - the large mouth bass are literally jumping. This is for the buyer who wants seclusion and privacy - you can't even see most of property or house from Temple Dr. Sought after Winter Park schools - Dommerich Elem, Maitland Middle and Winter Park High. Enjoy the best the metro Orlando area has to offer - Central Florida's gem - Winter Park. Your own piece of old Florida charm. less
Listing Provided Courtesy of Keller Williams Winter Park
Popularity
$208,000
$770/mo
Monthly Payment:
$770
Principal & Interest:
$770
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $41,600 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,261sq ft $165 / sq ft SFR
Lot Size7,613sq ft Built1956 On Site98days
Come home to this beautiful winter park residence that has been totally remodeled. Worry free for years to come with new roof, air conditioner, water heater, recently re-plumbed... more
Come home to this beautiful winter park residence that has been totally remodeled. Worry free for years to come with new roof, air conditioner, water heater, recently re-plumbed and newer appliances with one year home warranty. Bedrooms are bright and spacious with nice size closets. Bonus room/ office has a great view of the lovely newly landscaped backyard. Kitchen boasts new cabinets with adjacent spacious dining and bright living area. Perfect location close to i-4, enjoy the hoping night life and restaurants at winter park village. Trader joes, hillstone and more. Ideal starter home. less
Listing Provided Courtesy of La Rosa Realty, Llc
Popularity
$665,000
$2,596/mo
Monthly Payment:
$2,596
Principal & Interest:
$2,463
HOA Dues:
$133
(Based on a 30 year fixed loan at 3.75% with $133,000 down)
Winter Park, FL 32792
Seminole County School District
5bed 5bath 3,956sq ft $168 / sq ft SFR
Lot Size15,356sq ft Built1993 On Site98days
Absolutely stunning executive pool/spa home w/ separate in-law quarters on an oversized corner lot in winter park’s prestigious & gated bear gully pointe! This home is... more
Absolutely stunning executive pool/spa home w/ separate in-law quarters on an oversized corner lot in winter park’s prestigious & gated bear gully pointe! This home is laden w/ impressive architectural features & upgrades: plantation shutters, crown molding & hardwood floors! From the moment you enter, you’ll love the mesmerizing view of the fabulous pool/lanai, the soaring ceilings, circular-style staircase & bright, open floor plan! Ideal layout features a downstairs master bedrm & an adjacent bedrm. Upstairs are two more bedrms, two baths & a loft. The in-law suite is accessed on the other side of the pool, w/ its own bath/living area. All living areas overlook the expansive screened/covered lanai & htd pool/spa w/ multiple sets of sliding glass doors. The impressive kitchen is the heart of the home & perfect for entertaining w/ granite & corian counters, ss appliances, island, gas cooktop, double ovens, counter bar, butler’s pantry & desk, oversized walk-in pantry & a breakfast nook! Oversized master overlooks pool/lanai & features its own sitting area & a 16x13 bath w/ garden tub, rimless shower & a 14x10 organizer closet! Large laundry rm w/ w/d included; spacious 3-car side entry garage features an epoxy finish; gas water heater; circular front driveway, extended side driveway, upgraded landscaping. Fantastic community w/ its own tennis cts & playground. Conveniently located 2 minutes from trinity prep; 3 minutes to the 417; 10 minutes to downtown winter park/park ave, 15 min to the airport or ucf. less
Listing Provided Courtesy of Keller Williams Advantage Rlty
Popularity
$2,375,000
$8,799/mo
Monthly Payment:
$8,799
Principal & Interest:
$8,799
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $475,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size41,874sq ft BuiltN/A On Site99days
Premier oversized lakefront lot in A+ prime location on Lake Mailtand - largest lake on the 6-lake chain... This lot orients well for a gated entrance and privacy to set home... more
Premier oversized lakefront lot in A+ prime location on Lake Mailtand - largest lake on the 6-lake chain... This lot orients well for a gated entrance and privacy to set home back away from the street... Enjoy picturesque long sunset views from this .96 acre Lake Maitland property. A park like setting surrounded by lush landscaping and mature Oak trees & Cypress tress... Quiet, secluded neighborhood in the heart of the Via's off Via Tuscany... conveninet to the WPRC (Winter Park Racquet Club) and ICC (Interlachen Country Club)... Build your dream lakefront estate on this wonderful proeprty cleared and ready for new constuction! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$309,000
$1,144/mo
Monthly Payment:
$1,144
Principal & Interest:
$1,144
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $61,800 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,919sq ft $161 / sq ft SFR
Lot Size9,344sq ft Built1963 On Site99days
Don't miss out on your chance to own in the desired Brookshire community. This 3/2 ranch home is zoned for "A" schools, close Proximity to Cady Way biking/walking trail,... more
Don't miss out on your chance to own in the desired Brookshire community. This 3/2 ranch home is zoned for "A" schools, close Proximity to Cady Way biking/walking trail, Showalter track and field, and close to downtown Winter Park (Park Ave.) featuring shops, quaint restaurants, churches, Sun Rail and Central Park. . This home also offers a private fenced back yard made to entertain with a pool, hot tub, and covered patio! Call today to schedule a private tour. less
Listing Provided Courtesy of Warner-quinlan Inc
Popularity
$174,900
$669/mo
Monthly Payment:
$669
Principal & Interest:
$647
HOA Dues:
$22
(Based on a 30 year fixed loan at 3.75% with $34,980 down)
Winter Park, FL 32792
Seminole County School District
2bed 2bath 1,367sq ft $128 / sq ft SFR
Lot Size5,336sq ft Built1986 On Site99days
Short Sale. Buyer may need to pay transaction fee - Explained in addendum attached to MLS. Open entry way and kitchen with a pool! Two master suites with walk-in closets both... more
Short Sale. Buyer may need to pay transaction fee - Explained in addendum attached to MLS. Open entry way and kitchen with a pool! Two master suites with walk-in closets both with sliding doors exiting out to the pool/patio. Two full baths and a small office/bonus room. Granite counter tops, two car garage. Bold decorator colors! Fabulous neighborhood with playground, tennis courts, and lake access. Two patios. Beautiful trees and flowering plants. Plantation shutters, corner fireplace, bay window overlooking pool, vaulted ceilings. less
Listing Provided Courtesy of Me Realty, Llc
Popularity
$549,000
$2,034/mo
Monthly Payment:
$2,034
Principal & Interest:
$2,034
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $109,800 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
6bed 7bath 4,072sq ft $135 / sq ft SFR
Lot Size17,500sq ft Built1935 On Site99days
This newly renovated historic home is on a double lot in the beautiful dubsdread hieghts community. Just steps from the the historic dubsdread golf course and merely minutes... more
This newly renovated historic home is on a double lot in the beautiful dubsdread hieghts community. Just steps from the the historic dubsdread golf course and merely minutes from the art district of winter park and downtown Orlando. This custom home was renovated in 2015 on a lot size of 125 x 140. A detached 652 s/f 1 bed/1 bath home is included in sq. footage. The 2+car garage has also been converted into an 1 bed one bath efficiency as well which is includes in the sq footage calculations. 3 lots on both sides of this home are also for sale. realtor only remarks. Custom designed cathedral ceilings in the Family/Great Room will be the talking point of your guests when they visit your new residence. This home has 2 fireplaces in the main house. The following renovations were completed within the last year; travertine flooring, refinished solid oak hardwood flooring, All new cabinets and granite countertops in the kitchen and bathrooms, New Irrigation system, New paved driveway, New exterior paint, and new interior paint in all rooms. The garage conversion/in law suite features a kitchen and 1 bath. The separate guest house features new cabinets in the kitchen and bathroom, and a fireplace. The main house is around 2900sq ft 4bed 4.1/2 bath. the garage conversion and the guest house are both 1/1 and are each aroun 600sq ft. less
Listing Provided Courtesy of Homefirst Realty
Popularity
$2,984,755
$11,058/mo
Monthly Payment:
$11,058
Principal & Interest:
$11,058
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $596,951 down)
Winter Park, FL 32789
Orange County School District
5bed 8bath 9,161sq ft $326 / sq ft SFR
Lot Size28,577sq ft Built1996 On Site99days
Park Ave Mediterranean 3 story estate just steps to dining, shopping & golf. Privately gated with immaculate landscaping, fruit trees, koi pond, fountain and screen enclosed... more
Park Ave Mediterranean 3 story estate just steps to dining, shopping & golf. Privately gated with immaculate landscaping, fruit trees, koi pond, fountain and screen enclosed pool area with summer kitchen and auto awning. Inside you'll find 5 bedrooms, 7.5 baths, elevator, finished basement and gorgeous features throughout including solid oak hardwood floors with decorative inlays, French solid wood doors, wrought iron fixtures and continuous archways. The dramatic foyer opens into a formal living area complete with French doors leading to lanai. A formal dining room is perfectly situated near the butler's pantry and a gourmet chef's kitchen with built-in shelves and office, commercial 6 burner gas range, 2 Sub-Zero refrigeration systems in wall cabinetry, 6 refrigerator drawers, double full size Thermador ovens, stainless steel appliances, granite counter tops and an ample walk-in pantry. Plenty of counter seating next to the breakfast nook and a spacious family room with vaulted ceiling, built-ins, wet-bar and fireplace. The 1st of 2 master suites is just beyond the well-appointed office with cherry built-ins and fireplace. Both masters feature fireplaces, xtra lrg walk-in closets & cedar closets, double sinks, and separate showers/garden tubs. The 2nd master is upstairs along with 2 bedrooms with private baths, a fully furnished media room and separate loft as well as a separate guest suite above the 3 garage. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$212,000
$785/mo
Monthly Payment:
$785
Principal & Interest:
$785
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $42,400 down)
Winter Park, FL 32789
N/Asq ft N/A / sq ft LND
Lot Size19,316sq ft BuiltN/A On Site99days
Looking to build your dream home?? Perfect location on this 19,000 sq. ft. corner lot with deeded access to Lake Killarney - one of Winter Park's most private and desirable ski... more
Looking to build your dream home?? Perfect location on this 19,000 sq. ft. corner lot with deeded access to Lake Killarney - one of Winter Park's most private and desirable ski lakes! Beautiful new homes on same street. Conveniently located near I-4, Winter Park Village, in the heart of new development, shopping and dining on Park Ave. *Seller paid over 20k for plans for a 5 bed, 5 bath custom home with 3692 sq. ft. (SEE ATTACHMENTS). 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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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.

The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Mid-Florida Regional Multiple Listing Service and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited.

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Data last updated: Thursday, July 30, 2015 at 7:54 PM. Properties in listings may have been sold or may no longer be available.