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South Shore Wellington Homes For Sale

ESTABLISHED LAKEFRONT LUXURY & CUSTOM ESTATE FREEDOM

Expert Perspective: The South Shore Renovation Play

In the 2026 market, South Shore is the "Grand Dame" of Wellington. As a builder, I view this as one of the best neighborhoods for long-term equity. Most homes were custom-built in the 1980s, meaning they feature substantial CBS construction on lot sizes (0.33 to 0.50 acres) that you simply won't find in newer gated communities. The big draw? Many homes sit directly on Lake Wellington, offering private docks and motorized boating access.

With a current median price of $845,000, South Shore offers a "no-HOA" lifestyle that is increasingly rare. For clients looking to do high-end modernizations, the "bones" of these homes are excellent. You are within walking distance of the Wellington Amphitheater and Scott's Place Playground, making this the perfect blend of nostalgic Wellington charm and modern luxury potential.

Live South Shore Insider Data: April 2026

Properties in South Shore are currently holding 100% of ask price on average. Get the real-time contract and lakefront sales data below.

ACCESS FULL SOUTH SHORE MARKET REPORT →

Search Nearby Wellington Communities

1468 NORTHAMPTON Terrace, Wellington image
1468 NORTHAMPTON Terrace, Wellington — 1 $729,000

Welcome to this 4-bedroom, 2.5-bathroom home on a spacious waterfront lot at the end of a quiet cul-de-sac in the heart of Wellington, with no HOA. The fenced backyard fe...

  • 4 Beds
  • 3 Baths
  • B26089314 MLS
  • 1 Bldg.
12724 Westport Cir, Wellington image
12724 Westport Cir, Wellington — South Shore 1 Of Wellingt $949,900

Welcome to Lakeside Shores of Wellington! Spacious 5-bedroom, 3-car garage Lakefront Home. Features lots of Natural Light, Open Floor Plan with Sunroom, Screen- Enclosed...

  • 5 Beds
  • 3 Baths
  • A12082977 MLS
  • South Shore 1 Of Wellingt Bldg.
990 Hickory Trail, Wellington image
990 Hickory Trail, Wellington $849,000

Charming renovated, 4-bedroom, 2-bath home on a corner lot with screened in private pool. Impact windows with tiled floors throughout. Brand-new roof and NO HOA! Convenie...

  • 4 Beds
  • 2 Baths
  • B26070621 MLS
12768 Westhampton Circle, Wellington image
12768 Westhampton Circle, Wellington — Hampton Bay $399,000

Why rent for season when you can own your own Wellington retreat? This desirable end-unit townhouse is ideally located on corner of Forest Hill Boulevard and within walk...

  • 3 Beds
  • 3 Baths
  • B26067536 MLS
  • Hampton Bay Bldg.
1230 BLOCK ISLAND Road Unit 1, Wellington image
1230 BLOCK ISLAND Road Unit 1, Wellington $800,000

Rare Wellington Duplex Opportunity! Whether you're looking to expand your investment portfolio or live in one unit while generating income from the other, this fully furn...

  • B26067062 MLS
1262 The 12th Fairway, Wellington image
1262 The 12th Fairway, Wellington $2,100,000

Turnkey furnished fourplex on the 12th Fairway! Four identical 2BR/2BA units, each fully furnished (living room, bedrooms, mounted TVs) with private furnished patios and ...

  • B26049019 MLS
1294 White Pine Drive Unit 1294, Wellington image
1294 White Pine Drive Unit 1294, Wellington $349,000 ▼

Recently remodeled 3 Bedroom 2.5 Bathroom home in the heart of Wellington. Bright, open layout with updated finishes throughout. Low monthly association fee. Convenient...

  • 2 Beds
  • 3 Baths
  • F10549624 MLS
1314 White Pine Dr Unit #8-B, Wellington image
1314 White Pine Dr Unit #8-B, Wellington — South Shore 4 Wellington $375,000 ▲

HIGHLY ATTRACTIVE INVESTMENT OPPORTUNITY IN SOUGHT AFTER AREA WELLINGTON! BEAUTIFUL 3 BEDROOM, 2 BATHROOMS ONE OF 4 UNITS FOR SALE! NO SHORT SALE OR REO! Owner selling 4 ...

  • 3 Beds
  • 2 Baths
  • A11917732 MLS
  • South Shore 4 Wellington Bldg.
1316 White Pine Dr, Wellington image
1316 White Pine Dr, Wellington — South Shore 4 Wellington $350,000 ▲

HIGHLY ATTRACTIVE INVESTMENT OPPORTUNITY IN SOUGHT AFTER AREA WELLINGTON! BEAUTIFUL 2 BEDROOMS 2 BATHROOMS ONE OF 4 UNITS FOR SALE! NO SHORT SALE OR REO! Owner selling 4 ...

  • 2 Beds
  • 2 Baths
  • A11917581 MLS
  • South Shore 4 Wellington Bldg.
1318 White Pine Dr, Wellington image
1318 White Pine Dr, Wellington — South Shore 4 Wellington $350,000 ▲

HIGHLY ATTRACTIVE INVESTMENT OPPORTUNITY IN SOUGHT AFTER AREA WELLINGTON! BEAUTIFUL 2 BEDROOMS, 2 BATHROOMS ONE OF 4 UNITS FOR SALE! NO SHORT SALE OR REO! Owner selling 4...

  • 2 Beds
  • 2 Baths
  • A11917799 MLS
  • South Shore 4 Wellington Bldg.
1338 White Pine Dr, Wellington image
1338 White Pine Dr, Wellington — South Shore 4 Wellington $375,000 ▲

HIGHLY ATTRACTIVE INVESTMENT OPPORTUNITY IN SOUGHT AFTER AREA WELLINGTON! BEAUTIFUL 3 BEDROOMS, 2 BATHROOMS ONE OF 4 UNITS FOR SALE! NO SHORT SALE OR REO! Owner is sellin...

  • 3 Beds
  • 2 Baths
  • A11917776 MLS
  • South Shore 4 Wellington Bldg.