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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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$2,099,999
$7,780/mo
Monthly Payment:
$7,780
Principal & Interest:
$7,780
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $420,000 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 6,138sq ft $342 / sq ft SFR
Lot Size20,335sq ft Built2002 On Site26days
Gorgeous 5 bedroom home with lake view. When you enter through the double, hand carved, wood front doors, you will be greeted with the elegant living room and fireplace. The... more
Gorgeous 5 bedroom home with lake view. When you enter through the double, hand carved, wood front doors, you will be greeted with the elegant living room and fireplace. The formal banquet sized dining has a window seat and view of the lake. The office/library also has a fireplace. The gourmet kitchen has beautiful granite counters, miele built in coffee maker and a Thermador 6 burner gas stove that will excite the chef in you. The kitchen flows into the family room and breakfast area. Off the family room is a bonus room full of light and french doors to the private patio and pool area. The master bedroom and 5th bedroom complete the first floor. Both have french doors to the pool area. There are 2 staircases to the upstairs. The main staircase leads you to a loft, bedroom with balcony and bath, and two very large bedrooms with spacious connecting bath. There is also an additional room for toys, crafts or storage. The second staircase brings you to a large media and game room above the three car garage. measurements are approximate . less
Listing Provided Courtesy of Terza Real Estate
Popularity
Your search results are current and complete. Learn more
$599,000
$2,219/mo
Monthly Payment:
$2,219
Principal & Interest:
$2,219
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $119,800 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,948sq ft $307 / sq ft SFR
Lot Size16,140sq ft Built1963 On Site26days
PARK GROVE! Terrific opportunity in one of Winter Park's most desirable, sought after and long-established neighborhoods. This home is situated on a large, corner lot and... more
PARK GROVE! Terrific opportunity in one of Winter Park's most desirable, sought after and long-established neighborhoods. This home is situated on a large, corner lot and features include a new kitchen with granite, glass tile backsplash, and handsome cabinets. The private backyard, open pool and patio are great for entertaining. Interior appointments include a brick, wood-burning fireplace, built-ins, separate dining room, crown molding, 3 bedrooms, 2.5 baths and an interior utility/laundry room. Roof and a/c replaced in 2014. "A" rated public schools as well as a private elementary (Park Maitland School) are just minutes away. Bonus: This home is within steps to downtown Winter Park's charming Park Avenue - loaded with both unique and well-known shops, acclaimed restaurants, wine bars, museums, Central Park, a public golf course and much more. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$899,900
$3,334/mo
Monthly Payment:
$3,334
Principal & Interest:
$3,334
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $179,980 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 3,266sq ft $276 / sq ft SFR
Lot Size12,035sq ft Built1958 On Site26days
One of a kind charming 5 bedroom 4 bath in the much sought after Winter Park Via neighborhood. Top rated Winter Park Schools. As you enter this inviting relaxed family home... more
One of a kind charming 5 bedroom 4 bath in the much sought after Winter Park Via neighborhood. Top rated Winter Park Schools. As you enter this inviting relaxed family home through the double doors you will notice a warm friendly large kitchen showcasing light wood cabinets with dark granite counter tops . Saltillo tile and wood floors throughout the home. Large family room with wood burning fireplace , bright sunroom overlooking private backyard and pool. Large master suite, split plan on first floor with additional 3 bedrooms. Upstairs you will find an oversized bedroom with ensuite bath and large closet. This home showcases exceptional value. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$149,000
$552/mo
Monthly Payment:
$552
Principal & Interest:
$552
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $29,800 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
3bed 1bath 973sq ft $153 / sq ft SFR
Lot Size6,750sq ft Built1940 On Site26days
Winter Park, Lake Killarney area. Modern and Classic styles come together in this attractive 3 bed/1 bath home with new roof, new front and back doors, updated kitchen, freshly... more
Winter Park, Lake Killarney area. Modern and Classic styles come together in this attractive 3 bed/1 bath home with new roof, new front and back doors, updated kitchen, freshly painted inside and out, new septic system. Features eat-in kitchen, interior laundry, hardwood floors, claw foot bathtub, brick paver driveway. Desirable location close to shopping, restaurants, and Winter Park area amenities. Convenient access to I-4 and 408. less
Listing Provided Courtesy of Ferrell Realty, Inc.
Popularity
$1,400,000
$5,303/mo
Monthly Payment:
$5,303
Principal & Interest:
$5,186
HOA Dues:
$117
(Based on a 30 year fixed loan at 3.75% with $280,000 down)
Winter Park, FL 32792
Seminole County School District
6bed 5bath 5,796sq ft $242 / sq ft SFR
Lot Size15,001sq ft Built2002 On Site27days
Stunning custom home in a gated community of 15 homes in winter park is waiting for a new owner. This spacious 6/4.5 home, 4-car garage, around 6,300 sq ft (per the seller) has... more
Stunning custom home in a gated community of 15 homes in winter park is waiting for a new owner. This spacious 6/4.5 home, 4-car garage, around 6,300 sq ft (per the seller) has something for everyone. First level features huge master bedroom overlooking the pool with a luxurious bathroom, huge mother-in-law or guest suite with private bath, large office with built-in bamboo shelves and flooring. The estate features custom contemporary kitchen with 42+ inch cabinets with blue pearl granite countertops, top of the line appliances including a sub-zero refrigerator, two dishwashers, island, gas cooktop. Family room is wrapped in custom cabinets adding convenient hidden storage space. Living room, which the owner uses as a music room, fits a grand piano and is separated from the master bedroom by a soundproof wall. The second floor offers three more bedrooms and two bathrooms, giant game room with bar and refrigerator, study den equipped with custom cabinetry, breathtaking upstairs patio overlooking a neighborhood pond and a lake! Top of the line insulation, 3 ac units, a water heater with re-circulating water flow secure the lowest utility bills in the neighborhood! Each room in the house is accentuated with custom ceiling designs, crown moldings, central vacuum and 12'-20' ceilings. Strategic floor plan layout is ideal for large family who loves to entertain. Custom outdoor kitchen and a saltwater pool with jacuzzi and a waterfall. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$699,000
$2,589/mo
Monthly Payment:
$2,589
Principal & Interest:
$2,589
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $139,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,428sq ft $204 / sq ft SFR
Lot Size7,518sq ft Built1998 On Site27days
Delightful 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... more
Delightful 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 and updated appliances, a downstairs office, and an oversized bonus room. Master suite offers French doors that lead to the screened lanai, a deep garden tub, his and her vanities and a large walk-in closet. Upstairs are three generously sized bedrooms, each with great closet space, a full bath, and a bonus room over the garage. Fenced in backyard, open brick courtyard, and mature landscaping provide a private, outdoor escape. Zoned for A-rated Dommerich Elementary, Maitland Middle, and Winter Park High. Minutes from Park Avenue, shops and dining, and neighborhood parks. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$149,900
$555/mo
Monthly Payment:
$555
Principal & Interest:
$555
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $29,980 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
4bed 3bath 2,820sq ft $53 / sq ft SFR
Lot Size10,932sq ft Built1922 On Site27days
Fabulous home, HUGE lot, huge potential!! Property is sold as is, where is. The seller never occupied this home. Needs work & TLC. All showings must be accompanied by an Agent.... more
Fabulous home, HUGE lot, huge potential!! Property is sold as is, where is. The seller never occupied this home. Needs work & TLC. All showings must be accompanied by an Agent. Cash only offers!! All offers must be sent in with As-Is Contract and Proof of Funds. GREAT POTENTIAL!!! less
Listing Provided Courtesy of Carolyn Moriarty & Company Inc
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
Orange County School District
3bed 2bath 2,080sq ft $264 / sq ft SFR
Lot Size9,684sq ft Built1960 On Site27days
Move in ready!! Do not miss this wonderful winter park home located in the kenilworth shores area. This home boast pride of ownership as soon as you walk up the driveway. Notice... more
Move in ready!! Do not miss this wonderful winter park home located in the kenilworth shores area. This home boast pride of ownership as soon as you walk up the driveway. Notice the amazing manicured yard with brick accents, large oak trees, and a very inviting front patio! The home has original hardwood and brazilian cherry floors, crown molding, large baseboards and plantation shutters through out the home. In the formal living room you will find a wood burning fireplace, built in cabinets and a wonderful bay window overlooking the lush front yard. The gourmet kitchen is a cooks dream with cherry cabinets, granite counter tops and a wonderful breakfast nook overlooking the well landscaped backyard. Off the kitchen you will find a formal dining room that leads into a cozy family room that also opens to yet another outdoor patio. The master suite is over sized and includes a walk in closet and updated master bathroom. New ac unit, home has been recently been re-plumbed and new electrical work. 2 car garage and great school district! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$749,000
$2,774/mo
Monthly Payment:
$2,774
Principal & Interest:
$2,774
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $149,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,764sq ft $271 / sq ft SFR
Lot Size15,722sq ft Built1955 On Site27days
Canal front home with direct access to the Winter Park Chain of Lakes. This one-story 4 bedroom traditional home is located in a quiet setting and set up perfect for... more
Canal front home with direct access to the Winter Park Chain of Lakes. This one-story 4 bedroom traditional home is located in a quiet setting and set up perfect for entertaining. Enjoy the waterfront setting directly in your back yard surrounded by nature. Exterior features include boat dock with lift, separate lift for wave runner or smaller watercraft, private pool, mature landscaping, and 2 porches for relaxing. Interior features include a split plan with 4 bedrooms, media room, family room with spectacular views of the canal and “preserve” across the canal, tongue and groove ceilings in family room, stainless steel appliances, wine storage closet, 2 wood burning fireplaces, and newly renovated master bathroom with granite countertops and large spa tub. All located in the Dommerich Elementary, Maitland Middle, and Winter Park High School district. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$179,900
$666/mo
Monthly Payment:
$666
Principal & Interest:
$666
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $35,980 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,554sq ft $116 / sq ft SFR
Lot Size7,757sq ft Built1956 On Site27days
This 2 bedroom/2 bath with bonus room has lots of character and is located in established neighborhood just west of 17-92 in Winter Park. Cute kitchen with brick accent wall,... more
This 2 bedroom/2 bath with bonus room has lots of character and is located in established neighborhood just west of 17-92 in Winter Park. Cute kitchen with brick accent wall, ceramic back splash & ceramic floor opens to dinette with hardwood flooring. Spacious living room with big picture window has hardwood flooring under carpet. A separate family room with new wood flooring has wood burning fireplace and opens to screened in patio with river rock flooring. The master bedroom has a walk-in cedar closet plus separate sitting area perfect for office or reading nook. Replumbed in 1995 with newer windows. The roof, A/C & water heater were replaced in 2003. Very nice corner lot with one carport in front and one in rear. Easy access to I-4 and only minutes to Winter Park Village. less
Listing Provided Courtesy of Anne Rogers Realty Group Inc
Popularity
$3,769,000
$14,184/mo
Monthly Payment:
$14,184
Principal & Interest:
$13,963
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $753,800 down)
Winter Park, FL 32789
Windsong Orange County School District
5bed 7bath 6,472sq ft $582 / sq ft SFR
Lot Size25,911sq ft Built2003 On Site28days
Beautiful 5 bedroom Lakefront Estate in desirable Cul-de-Sac of Windsong South. Main floor boasts beautifully appointed Master bedroom and large ensuite bath, media room with... more
Beautiful 5 bedroom Lakefront Estate in desirable Cul-de-Sac of Windsong South. Main floor boasts beautifully appointed Master bedroom and large ensuite bath, media room with projection screen, family room and gourmet kitchen with large eating area and expansive views of lake Berry. Living room with fireplace and dining room with butler’s pantry ideal for entertaining family and friends. Upstairs bonus room and exercise area, wet bar landing, and 3 large bedrooms each with their own private full bath. Separate entrance to large in-law suite with private stairway. Every room in the rear of the home intentionally captures lake views that are certain to take your breath away ! Covered lanai, outdoor summer kitchen with screened in eating area, boat dock, and lower yard beyond infinity pool is ideal for outdoor entertaining as well. Finish level and floor plan second to none. Custom finishes throughout and attention to every detail. Recent Entertainment and Technology upgrade with Crestron Home Control System. A must see for anyone looking for a home that offers intentional function and truly elegant comfort. less
Listing Provided Courtesy of Parkland International Realty
Popularity
$424,995
$1,708/mo
Monthly Payment:
$1,708
Principal & Interest:
$1,574
HOA Dues:
$134
(Based on a 30 year fixed loan at 3.75% with $84,999 down)
Winter Park, FL 32792
4bed 3bath 2,681sq ft $159 / sq ft SFR
Lot Size7,860sq ft Built2015 On Site28days
The “jackson” is an award winning floorplan! Located in eden point, an exclusive and intimate gated community with a winter park address. Open floorplan with 4... more
The “jackson” is an award winning floorplan! Located in eden point, an exclusive and intimate gated community with a winter park address. Open floorplan with 4 bedrooms, 2 ½ baths, separate dining room, kitchen nook and family room overlooking the large covered lanai. Large master bedroom separated from the 3 secondary bedrooms. The tandem garage is oversized and could fit 4 cars. This desirable location is within minutes of exhilarating recreation and a vibrant restaurant scene. Excellent schools, and major employers are only a short drive. You will love the “jackson”! eden point is an exclusive gated community that includes a collection of 9 single-family homes and a great winter park address. The natural beauty and mild climate that made this area the preferred winter resort for the wealthy in the early 20th century can be yours year-round in this intimate gated enclave. Built on 26 acres on the southern shore of garden lake, eden point is a rare opportunity to own a new in this desirable location & the community echoes the ambience of old florida while giving residents easy access to all the modern conveniences. Excellent public & private schools, major employment centers, exciting cultural attractions, exhilarating recreation & a vibrant restaurant scene are all within minutes. Builder warranty! (disclaimer: some/all the photos are stock/renderings of the home.) less
Listing Provided Courtesy of Taylor Morrison Rlty Of Fla
Popularity
$674,900
$2,500/mo
Monthly Payment:
$2,500
Principal & Interest:
$2,500
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $134,980 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 3,332sq ft $203 / sq ft SFR
Lot Size7,875sq ft Built1950 On Site29days
Beautiful 3 bedroom 4 bath home in Olde Winter Park. This home was significantly remodeled in 2009 with wood floors, crown molding, gourmet kitchen with granite counters,... more
Beautiful 3 bedroom 4 bath home in Olde Winter Park. This home was significantly remodeled in 2009 with wood floors, crown molding, gourmet kitchen with granite counters, beautiful cabinets & travertine. The home was significantly enlarged, adding a second floor with bonus room along with two bedrooms and baths upstairs. Master down with a spacious master bath. Large fenced backyard with a gorgeous pool. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$1,579,000
$6,071/mo
Monthly Payment:
$6,071
Principal & Interest:
$5,850
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $315,800 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 4,606sq ft $343 / sq ft SFR
Lot Size16,253sq ft Built2004 On Site30days
Spectacular four bedroom, four and one-half bath pool home in prestigious Windsong. Original Charleston Carolina lanterns, Brazilian cherry floors, solid mahogany French doors,... more
Spectacular four bedroom, four and one-half bath pool home in prestigious Windsong. Original Charleston Carolina lanterns, Brazilian cherry floors, solid mahogany French doors, custom wrought iron railings, and soaring ceilings; this home is absolutely stunning! Formal living and dining rooms, an open family room, and a guest suite with full bath provide a comfortable yet very functional first floor. Gorgeous gourmet kitchen, complete with a custom farmhouse sink, gas stove, nickel-finish pendants, and white Carrera marble countertops has eat-in dining and views of the covered lanai and pool. Master bedroom features a private bath with marble shower and vanities, a large soaking tub, and an expansive walk-in closet. Additionally, two generously sized bedrooms and a bonus room over the garage can be found upstairs. Outdoors, enjoy quiet evenings or entertaining guests on the covered lanai with bead-board ceilings, or take a dip in the Hampton’s style pool. Located in one of Winter Park’s most desirable communities, Windsong offers its residents amenities like no other: chain of lake access, private boat rental, fishing pier, parks, two recreational pools, and a children’s water park. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$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 32789
Orange County School District
4bed 4bath 3,606sq ft $291 / sq ft SFR
Lot Size14,118sq ft Built1992 On Site30days
Elegant traditional home in heart of the Via’s on prime brick street… This home greets you with a grand 2-story foyer, extensive wood work/moldings, beautiful... more
Elegant traditional home in heart of the Via’s on prime brick street… This home greets you with a grand 2-story foyer, extensive wood work/moldings, beautiful hardwood floors, plantation shutters, French doors, light & bright home, gorgeous new modern island kitchen w/ stainless appliances & marble counters open to gathering room w/ fireplace & built ins…. Master suite on main level with new lavish master bath along with separate library with closet & built-ins (could be used as a 4th bedroom)… additionally a formal living room & separate dining room for entertaining… Upstairs includes 2 more large bedroom suites along with bonus rooms, and extensive storage… Outdoor living includes an oversized covered lanai open to a large fenced yard (plenty of room for a pool if desired) and private oversized 2-car detached garage… lush landscaping and mature oaks complete this wonderful property… There is room for potential expansion of this home as well… Convenient to ICC, WPRC, Phelps Park & YMCA all nearby! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
4 5 6 7 8 9 10 11 12 ... 17 27
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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: Tuesday, August 4, 2015 at 8:11 PM. Properties in listings may have been sold or may no longer be available.