$4,675,000

18989 SE WINDWARD ISLAND LN, JUPITER, FL 33458

4 beds5 baths4,650 sq ftHouseBuilt 2000
Updated today, November 3, 2026

This home against the area

$1,005 per sq ft
88 days on the market
Price cut $123,999 since it was listed at $4,798,999
$28,606 in property taxes (2025)
20,909 sq ft lot
Private pool
Waterfront
4 car garage

About this home

Experience ultimate Florida waterfront lifestyle in prestigious, gated Islands of Jupiter, private waterfront estates spread across 4 islands, renowned for its exclusivity, deep-water access, prime location in heart of Jupiter. Situated on 100 feet water frontage with no fixed bridges, this exceptional estate offers direct ocean access minutes from Ocean. Private dock accommodates 2-3 boats. Spanning 4,648 square feet, home features a thoughtfully designed split floor plan with 4 bedrooms, 5 baths, an additional living space, and a rare 4-car garage. Main level showcases an expansive primary suite and two guest suites, upstairs VIP retreat offers a sitting area, wet bar, private balcony with tranquil river views. Indoor-outdoor living, backyard is a private oasis complete with a resort-style pool and spa, screened patio, outdoor kitchen, cabana bath. Desirable eastern rear exposure captures refreshing ocean breezes keeps outdoor living spaces cool and comfortable throughout the afternoon. Ideal setting for year-round entertainment and relaxation. Recent upgrades include new roof, beautifully renovated kitchen, fresh interior/exterior paint, porcelain-paver driveway, impact windows/doors throughout. Secluded setting, New full-house generator, whole-home water filtration system completes this move-in-ready waterfront retreat, where luxury, privacy, and premier boating access come together in one of Jupiter's most coveted boating communities.

Zoned schools

Elementary: Hobe Sound Elementary School
Middle: Murray Middle School
High: South Fork High School

From Martin County School District attendance zones.

Listing courtesy of Premier Flat Fee Realty LLC. MLS# A12068035.

Listing information is provided by the MLS and is deemed reliable but not guaranteed.

Listed August 7, 2026.

Similar homes near JUPITER

Home for sale at 114 SOTA DR, JUPITER, FL 334585 photos

$4,695,000list price

Per sq ft$941

4 bd · 6 ba · 4,988 sq ft House

114 SOTA DR, JUPITER, FL 33458

Listing courtesy of Douglas Elliman. MLS# B26053572.On the MLS · Listed Jul 16

Home for sale at 906 DOLPHIN DR, JUPITER, FL 334585 photos

$4,625,000list price

Per sq ft$1,489

4 bd · 4 ba · 3,107 sq ft House

906 DOLPHIN DR, JUPITER, FL 33458

Listing courtesy of Premier Properties of South Fl. MLS# B26090958.On the MLS · Listed Oct 20

Home for sale at 934 N LOXAHATCHEE DR, JUPITER, FL 334585 photos

$4,795,000list price

Per sq ft$1,613

4 bd · 4 ba · 2,973 sq ft House

934 N LOXAHATCHEE DR, JUPITER, FL 33458

Listing courtesy of Illustrated Properties. MLS# B26078991.On the MLS · Listed Sep 21

Home for sale at 938 TURNER QUAY, JUPITER, FL 334585 photos

$4,490,000list price

Per sq ft$1,136

4 bd · 4.5 ba · 3,954 sq ft House

938 TURNER QUAY, JUPITER, FL 33458

Listing courtesy of Douglas Elliman. MLS# B26018829.On the MLS · Listed Apr 21

Home for sale at 187 BIRKDALE LN, JUPITER, FL 334585 photos

$4,950,000list price

Per sq ft$1,276

3 bd · 4.5 ba · 3,880 sq ft House

187 BIRKDALE LN, JUPITER, FL 33458

Listing courtesy of Frankel Ball Realty LLC. MLS# R11154518.On the MLS · Listed Jan 14

Home for sale at 115 ECHO LN, JUPITER, FL 334585 photos

$4,399,000list price

Per sq ft$884

4 bd · 5.5 ba · 4,978 sq ft House

115 ECHO LN, JUPITER, FL 33458

Listing courtesy of K2 Realty, Inc. (NPB). MLS# B26077499.On the MLS · Listed Sep 16