34

Homes for Sale near Brookshire Elementary

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  • /30

    $500,000

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    410 Saint Dunstan Way, Winter Park, FL 32792

    Welcome to 410 Saint Dunstan Way, a beautifully maintained 3-bedroom, 2-bath home ideally located in desirable Winter Park. Situated on a spacious .22-acre lot with **no HOA**, this property offers an excellent combination of comfort, convenience, and value.Offering 1,519 square feet of thoughtfully designed living space, the home features a functional floor plan with generous living and

    Agent Photo

    Milton James

    COLDWELL BANKER REALTY

    410 Saint Dunstan Way, Winter Park, FL 32792
  • /5

    $138,000

    $10K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 776 Sq Ft

    1000 S Semoran Blvd Unit 404, Winter Park, FL 32792

    Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool

    Scott Butts KIMBRIDGE REALTY, LLC

    1000 S Semoran Blvd Unit 404, Winter Park, FL 32792
  • /11

    $138,000

    $10K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 776 Sq Ft

    1000 S Semoran Blvd Unit 408, Winter Park, FL 32792

    Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool

    Scott Butts KIMBRIDGE REALTY, LLC

    1000 S Semoran Blvd Unit 408, Winter Park, FL 32792
  • /47

    $614,500

    $21K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,785 Sq Ft

    2708 Lion Heart Rd, Winter Park, FL 32792

    Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality.Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The

    Navid Rokh EQUITYPRO LLC

    2708 Lion Heart Rd, Winter Park, FL 32792
  • /83

    $1,800,000

    $389K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,382 Sq Ft

    2032 Kimbrace Place, Winter Park, FL 32792

    A PRIVATE BALINESE RESORT IN THE HEART OF WINTER PARK5 Bedrooms | 4 Bathrooms | 3,400+ SF|Saltwater Pool & Spa|Minutes to Park AvenueWelcome to a rare offering where luxury, tranquility, and architectural sophistication converge. Nestled in one of Winter Park's most desirable neighborhoods, just minutes from the boutiques, fine dining, and cultural attractions of Park Avenue, this custom

    Rob Sassos SIMPLICITY: A RE BROKERAGE CO

    2032 Kimbrace Place, Winter Park, FL 32792
  • /59

    $1,999,990

    New Construction $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,330 Sq Ft

    525 S Lakemont Ave, Winter Park, FL 32792

    Thoughtfully designed with an uncompromising commitment to quality, craftsmanship, and detail, this exceptional new construction residence is an expression of luxury living. Defined by its striking architecture and refined contemporary design, the home makes an unforgettable first impression with a dramatic two-story foyer featuring soaring ceilings, a statement staircase with custom millwork,

    Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    525 S Lakemont Ave, Winter Park, FL 32792
  • /8

    $2,700,000

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 3,588 Sq Ft

    648 Worthington Dr, Winter Park, FL 32789

    Under Construction. Located in the Kenilworth Shores neighborhood, this stunning new residence brings an elevated level of new construction to an increasingly desirable pocket of Winter Park. A sophisticated modern farmhouse façade creates an impressive first impression, framed by a sweeping double-entry curved driveway that gives the home a commanding yet welcoming presence. Inside, the

    Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    648 Worthington Dr, Winter Park, FL 32789
  • /22

    $660,000

    • 3 Beds
    • 3 Baths
    • 1,690 Sq Ft

    1256 Melissa Ct, Winter Park, FL 32789

    Very well maintained townhouse great location in Waterbridge on cul-de-sac near tennis courts. This 2 bedroom/den or 3 bedroom , 3 bathroom with primary upstairs and additional bedroom on main floor is renovated with hardwood floors downstairs, updated recessed lighting throughout, updated plumbing, volume ceilings, great ambient light and windows, barrel tile roof. Kitchen with updated

    Wesley Morales KELLER WILLIAMS REALTY AT THE PARKS

    1256 Melissa Ct, Winter Park, FL 32789
  • /29

    $494,900

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,565 Sq Ft

    2715 Prince John Rd, Winter Park, FL 32792

    GREAT HOME & GREAT VALUE — home needs cosmetic work and some TLC - if you DIY you could have instant equity. Thoughtful floor plan with two living spaces and a screened-in porch. Located in desirable Winter Park, 3 blocks from parks, cycling trails, and a public pool, plus minutes from Park Avenue’s shops and restaurants. Enjoy top-rated schools and a lovely, walkable neighborhood. Zoned for

    Donna Peebles VIA PROPERTIES LLC

    2715 Prince John Rd, Winter Park, FL 32792
  • /75

    $1,949,500

    $241K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,422 Sq Ft

    1420 Aloma Ave, Winter Park, FL 32789

    Experience a rare expression of design-forward lakefront living on Lake Sylvan in the heart of Old Winter Park. Fully remodeled through a comprehensive, down-to-the-studs transformation, virtually every major component is new—giving this approximately 2,400-square-foot residence the quality, systems and finishes of a modern custom home. Framed by mature live oaks and sweeping 180-degree water

    Alejandra Silva METROPOLITAN R.E SOLUTIONS INC

    1420 Aloma Ave, Winter Park, FL 32789
  • /44

    $999,000

    $46K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 2,638 Sq Ft

    616 Brechin Dr, Winter Park, FL 32792

    Welcome to your fully reimagined Florida home. Among tree-canopied streets in the desired Kenilworth Shores neighborhood, this mid-century modern ranch home was completely transformed in 2005. The redesign added substantial square footage and created a completely unique, functional floor plan that separates it from any other home in the area. Spanning 2,638 square feet of seamless indoor-outdoor

    Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    616 Brechin Dr, Winter Park, FL 32792
  • /4

    $1,750,000

    • Land
    • 16,117 Sq Ft
    • $4,729,730 per Acre

    313L Sylvan Dr, Winter Park, FL 32789

    Exceptional opportunity to build on beautiful Lake Sylvan with this 0.37-acre (approximately 16,603-square-foot) lakefront homesite. Offering a picturesque waterfront setting, the property is ideally positioned just minutes from Park Avenue's shops and restaurants, major roadways, leading hospitals and top private schools. Create a custom lakefront residence tailored to your vision in one of

    Mick Night PREMIER SOTHEBY'S INTL. REALTY

    313L Sylvan Dr, Winter Park, FL 32789
  • /10

    $5,500,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 4,775 Sq Ft

    313 Sylvan Dr, Winter Park, FL 32789

    Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportunity to own a thoughtfully curated custom home by renowned builder Floridian Custom Homes, brought to life in collaboration with Winter Park Design, Brianna Michelle Interior Design and Signature Landscape. Offering 4,775 heated

    Mick Night PREMIER SOTHEBY'S INTL. REALTY

    313 Sylvan Dr, Winter Park, FL 32789
  • /42

    $830,000

    $145K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,003 Sq Ft

    1507 Golfside Dr, Winter Park, FL 32792

    Virtually Staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW Wood & porcelain tile flooring

    Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    1507 Golfside Dr, Winter Park, FL 32792
  • /50

    $1,380,000

    $95K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,170 Sq Ft

    1751 Goodrich Ave, Winter Park, FL 32789

    Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes

    Stephanie Baldner EXP REALTY LLC

    1751 Goodrich Ave, Winter Park, FL 32789
  • /20

    $2,200,000

    • Land
    • 23,522 Sq Ft
    • $4,074,074 per Acre

    1415 Grove Terrace, Winter Park, FL 32789

    Exceptional opportunity to build your dream home in one of Winter Park’s most sought-after neighborhoods! This cleared, vacant homesite is ready for construction and offers the perfect canvas to create a custom residence tailored to your vision. Nestled on a quiet street, the property is surrounded by beautiful homes while providing convenient access to Park Avenue’s renowned shopping and dining,

    Milena Fernandes GOLDEN GROUP REALTY LLC

    1415 Grove Terrace, Winter Park, FL 32789
  • /22

    $115,000

    $14K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 735 Sq Ft

    1000 S Semoran Blvd Unit 305, Winter Park, FL 32792

    Freshly Updated 1-Bedroom Condo – Perfect for Homeowners or Investors! Whether you're looking for your first home, downsizing, or adding to your investment portfolio, this move-in-ready 1-bedroom, 1-bath condominium is an excellent opportunity. Featuring brand-new luxury vinyl plank flooring and a freshly painted interior, this home offers a clean, modern feel throughout. The open-concept floor

    Melissa Vance MAINFRAME REAL ESTATE

    1000 S Semoran Blvd Unit 305, Winter Park, FL 32792
  • /46

    $1,780,000

    $215K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,249 Sq Ft

    1750 Carollee Ln, Winter Park, FL 32789

    Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom, 3.5-bath, custom pool and spa residence offers more than 3,200 square feet of thoughtfully updated living space near Park Avenue, the Chain of Lakes and top-rated schools. The fully renovated 2025 kitchen serves as the

    Michelle Hochfelder PREMIER SOTHEBY'S INTL. REALTY

    1750 Carollee Ln, Winter Park, FL 32789
  • /11

    $449,000

    • Land
    • 6,098 Sq Ft
    • $3,207,143 per Acre

    0 Jessica Ct, Winter Park, FL 32789

    Some opportunities don't announce themselves. They show up quietly in Winter Park's most sought-after zip code, waiting for someone who knows exactly what to do with them.This vacant lot inside Waterbridge sits in the 32789 zip code, a rare chance to build the home you've always had in mind, in a neighborhood that has already decided who it is. Waterbridge is a tight-knit, tree-lined enclave

    Hannah True RE/MAX 200 REALTY

    0 Jessica Ct, Winter Park, FL 32789
  • /49

    $1,450,000

    $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,578 Sq Ft

    1421 Chapman Cir, Winter Park, FL 32789

    Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment you arrive, the classic barrel tile roof and timeless architectural character set the tone for what awaits inside — a home with enduring style, gracious proportions, and tremendous potential to be personalized for its next

    Kelly Price KELLY PRICE & COMPANY LLC

    1421 Chapman Cir, Winter Park, FL 32789
  • /2

    $1,590,000

    $100K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,786 Sq Ft

    708 Balmoral Rd, Winter Park, FL 32789

    A rare elevated corner lot in the heart of Winter Park — walkable to Park Avenue's boutique shops and restaurants, and set on one of the area's most desirable streets. Substantial homesite, prime location, endless potential.

    Caitlin De Oliveira EXP REALTY LLC

    708 Balmoral Rd, Winter Park, FL 32789
  • /10

    $335,000

    • 3 Beds
    • 2.5 Baths
    • 1,790 Sq Ft

    2526 Passamonte Dr Unit 10F, Winter Park, FL 32792

    Great investment opportunity, tenant occupied/income producing Winter Park property in gated community.

    Kathi Thomas LEGACY CORNERSTONE INC

    2526 Passamonte Dr Unit 10F, Winter Park, FL 32792
  • /19

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,088 Sq Ft

    2231 Nairn Dr, Winter Park, FL 32792

    Completely Remodeled Winter Park Home – Prime LocationBeautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing.Ideally situated directly across from Advent Health Winter Park Hospital, this property

    David Auerbach PARK TOWN REAL ESTATE LLC

    2231 Nairn Dr, Winter Park, FL 32792
  • /8

    $109,400

    • 1 Bed
    • 1 Bath
    • 785 Sq Ft

    311 Scottsdale Square Unit 311, Winter Park, FL 32792

    This 1 bedroom, 1 bath condo at 311 Scottsdale Sq, Winter Park, FL 32792 is leased to a reliable long-term tenant paying $1,450 / month. Located on the first floor in the established Winter Park Woods community, this unit features an open-concept layout as soon as you walk in. The HOA includes water, access to two community pools, a playground, and tennis courts. Winter Park Woods is also zoned

    Omar Rodriguez EMPIRE NETWORK REALTY

    311 Scottsdale Square Unit 311, Winter Park, FL 32792
  • /44

    $2,050,000

    New Construction $200K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 2,889 Sq Ft

    240 N Phelps Ave, Winter Park, FL 32789

    A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort.The open-concept living areas are

    Nickolas McKee KELLER WILLIAMS WINTER PARK

    240 N Phelps Ave, Winter Park, FL 32789
  • /70

    $2,995,000

    New Construction $505K PRICE DROP
    • 5 Beds
    • 6.5 Baths
    • 4,168 Sq Ft

    1836 Whitehall Dr, Winter Park, FL 32789

    Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil island paradise, this new custom home by Urban Perch, A Boutique Home Builder, offers a timeless front elevation, exquisite finishes inside and out, and unobstructed views of the beautiful outdoors from almost every room. Totaling 4,168 square feet, this five-bedroom, five-bath

    Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

    1836 Whitehall Dr, Winter Park, FL 32789
  • /24

    $3,300,000

    New Construction
    • 5 Beds
    • 5.5 Baths
    • 3,421 Sq Ft

    1627 Mizell Ave, Winter Park, FL 32789

    One or more photo(s) has been virtually staged. Under Construction. Under construction. Experience approachable luxury combined with wellness-focused living in this newly crafted masterpiece by Urban Perch, a boutique home builder. In downtown Winter Park, this stunning new construction home offers 3,421 square feet of elegant, efficient living area. The primary residence features four bedrooms

    Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

    1627 Mizell Ave, Winter Park, FL 32789
  • /13

    $138,000

    $10K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 796 Sq Ft

    1000 S Semoran Blvd Unit 306, Winter Park, FL 32792

    Virtually Staged. Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior

    Scott Butts KIMBRIDGE REALTY, LLC

    1000 S Semoran Blvd Unit 306, Winter Park, FL 32792
  • /12

    $1,750,000

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,350 Sq Ft

    1840 Anzle Ave, Winter Park, FL 32789

    Under Construction. NEW CONSTRUCTION – Under Construction. Welcome to Winter Park! This stunning modern residence is meticulously designed and ideally located near everything. This beautifully crafted home features 4 bedrooms, 2.5 bathrooms, and 2,350 square feet of living space, plus an additional 1,247 square feet of terraces and lanai. The open-concept kitchen showcases quartz countertops,

    Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT

    1840 Anzle Ave, Winter Park, FL 32789
  • /15

    $110,000

    $5K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 796 Sq Ft

    1000 S Semoran Blvd Unit 302, Winter Park, FL 32792

    Virtually Staged. ***Welcome to this exceptionally well-maintained 1-bedroom, 1-bathroom condominium ideally located in Winter Park! Lovingly cared for by its longtime owner, this home offers a wonderful combination of comfort, functionality, and convenience. *WASHER AND DRYER LOCATED IN UNIT* Inside, you'll find a spacious, thoughtfully designed layout featuring a generous living area, an

    Amaal Barakat KELLER WILLIAMS ADVANTAGE III

    1000 S Semoran Blvd Unit 302, Winter Park, FL 32792
  • /43

    $1,599,000

    • 5 Beds
    • 3.5 Baths
    • 3,028 Sq Ft

    1864 Grinnell Terrace, Winter Park, FL 32789

    Situated in the heart of Winter Park, this custom-built Mediterranean-style estate offers an exquisite living experience that marries timeless architecture with modern innovation. A dramatic grand foyer introduces a residence where every finish has been meticulously curated, from Turkish travertine stone and rich wood flooring to Brizo hardware in Brilliance Polished Gold. At the heart of the

    Robyn Brehne COLDWELL BANKER REALTY

    1864 Grinnell Terrace, Winter Park, FL 32789
  • /12

    $499,000

    • 2 Beds
    • 1 Bath
    • 920 Sq Ft

    230 Strathy Ln, Winter Park, FL 32792

    Completely Remodeled Winter Park Home – Prime LocationBeautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing.Ideally situated directly across from Advent Health Winter Park Hospital, this property

    David Auerbach PARK TOWN REAL ESTATE LLC

    230 Strathy Ln, Winter Park, FL 32792
  • /3

    $2,070,000

    New Construction $175K PRICE INCREASE
    • 5 Beds
    • 4.5 Baths
    • 3,617 Sq Ft

    914 Enclave Place, Winter Park, FL 32792

    Pre-Construction. To be built. 914 Enclave Place is a beautiful Alys Beach inspired design. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with

    Matthew Burks CORCORAN PREMIER REALTY

    914 Enclave Place, Winter Park, FL 32792
  • /31

    $1,262,500

    $13K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,024 Sq Ft

    2015 Summerfield Rd, Winter Park, FL 32792

    Welcome to one of Winter Park's most impressive move-in-ready homes, where luxury, comfort, and location come together seamlessly.Completely reimagined and renovated, this stunning 4-bedroom, 4-bath residence offers the rare combination of modern construction quality and an established Winter Park location just minutes from Baldwin Park, Park Avenue, Rollins College, and top-rated

    Courtney Lindsay UNITED REAL ESTATE PREFERRED

    2015 Summerfield Rd, Winter Park, FL 32792
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