Jack Winter Real Estate Agent - Cascade Hasson Sotheby's International Realty

5758 SW Cupola Dr, South Beach, OR For Sale $829,000 - listed by Jack Winter — For Sale $829,000

Jack Winter listing agent for 175 SW 59th St, South Beach, OR - sold for $965,000 — Sold $965,000

6440 SW Arbor Dr, Newport, OR For Sale $675,000 - listed by Jack Winter — For Sale $675,000

Jack Winter buyer's agent for 5920 SW Arbor Dr, Newport, OR - sold for $850,000 — Sold $850,000

220 SW 61st St, South Beach, OR For Sale $779,000 - listed by Jack Winter — For Sale $779,000

Jack Winter

Gleneden Beach OR

Cascade Hasson Sotheby's International Realty

35 Closed Sales

$23.5M Total Value

$395K - $1.8M Price Range

$670.3K Average Price

Prior 5 years

About Jack

With a business career built on trust and leadership, Jack Winter delivers an exceptional level of client service few can match.

Jack spent most of his professional career advising business organizations on significant transactions and strategic decisions. Today, he brings executive-level insight to every real estate transaction. Known for his integrity, responsiveness, and dedication to client success, Jack has earned a reputation as a trusted advisor who listens carefully, communicates consistently, and delivers results.

As a thirty-year homeowner in Newport's Southshore community, Jack offers firsthand knowledge of Oregon's central coast lifestyle and differences in the various coastal cities and neighborhoods. His understanding of these communities—combined with a passion for helping clients achieve their goals—makes him an invaluable partner throughout the buying and selling process.

When you work with Jack Winter, you are not just hiring a Realtor®—you are gaining a seasoned business leader, skilled negotiator, and trusted advocate committed to helping you make confident real estate decisions.

Home Types: Mobile Homes, House, Lot/Land, Condo

Years of Experience: 8

Education: BA Degree in Accounting

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	2
Total Value	$1,700,000
Average Sale Price	$850,000
Price Range	$735K - $965K

Buyer Deals
Total Deals	1
Total Value	$850,000
Average Sale Price	$850,000

Seller Deals
Total Deals	7
Total Value	$5,708,000
Average Sale Price	$815,429
Price Range	$275K - $1.8M

Buyer Deals
Total Deals	2
Total Value	$1,810,000
Average Sale Price	$905,000
Price Range	$850K - $960K

Seller Deals
Total Deals	31
Total Value	$20,970,000
Average Sale Price	$676,452
Price Range	$200K - $1.8M

Buyer Deals
Total Deals	4
Total Value	$2,492,000
Average Sale Price	$623,000
Price Range	$287K - $960K

5 Year View

Areas Jack is Experienced In

Jack's Listings and Deals

Jack's Recent Active Listings

$829,000
- 2 Beds
- 2 Baths
- 1,614 Sq Ft
5758 SW Cupola Dr

South Beach, OR
This rare end-unit oceanfront condominium is in the Southshore gated community in South Beach, Oregon. This home was built with exterior concrete walls, ceilings and floors. This construction method offers superior energy efficiency and sound proofing than traditional stick-built construction. The condo has extra-large windows and its specific location on the north-end results in premium views of

Jack Winter Cascade Hasson Sotheby's International Realty

$675,000
- Land
- 0.3 Acre
- $2,250,000 per Acre
6440 SW Arbor Dr

Newport, OR
This premium oceanfront lot is fully developed and ready for your dream home in the private, gated Southshore community in Newport, Oregon. The building site offers a spectacular 180-degree vantage point of the mighty Pacific on 100' feet of low-bank ocean front. The lot is fully developed with all utilities at the street including public water and sewer. Geological hazard assessment reports are

Jack Winter Cascade Hasson Sotheby's International Realty

$779,000
- 2 Beds
- 2 Baths
- 2,094 Sq Ft
220 SW 61st St

South Beach, OR
One of the original Southshore cottages, this well-maintained Cape Cod-style residence in Southshore's village by the sea presents a great opportunity to own a home located near the community clubhouse, sports courts and beach access paths. Designed with convenience in mind, the home provides the comfort of main-floor living plus a large open space loft that can be used as flex space for overflow

Jack Winter Cascade Hasson Sotheby's International Realty

$885,000
- 3 Beds
- 2.5 Baths
- 2,150 Sq Ft
205 SW 58th St

South Beach, OR
Offered for the first time by the original owners, this beautifully maintained Cape Cod-style residence in Southshore's village by the sea presents a rare opportunity to own a former model home showcasing premium upgrades and timeless coastal charm. Situated on a desirable corner lot just a short stroll from beach access and miles of uninterrupted sandy shoreline, this 2,150 square-foot home

Jack Winter Cascade Hasson Sotheby's International Realty

$975,000
- 3 Beds
- 2.5 Baths
- 3,467 Sq Ft
110 SW 61st St

South Beach, OR
Enjoy life at the beach in this custom designed two-level home in the Southshore community Newport Oregon. This home was originally designed for multi-generational living. Each area of the home is spacious and can be configured to fit the lifestyle of the new owners. The main floor living area has a vaulted ceiling, gas insert fireplace and is currently used as a combination living and formal

Jack Winter Cascade Hasson Sotheby's International Realty

$949,000
- 4 Beds
- 3 Baths
- 2,917 Sq Ft
5820 SW Arbor Dr

South Beach, OR
Relax and enjoy life at the beach in this beautiful 4 bed, 3 bath home in the gated Southshore community. The home is constructed with exterior concrete walls with superior insulation and strength compared to traditional wood framing. This method promotes a quiet, clean and energy efficient living environment. The fenced backyard and amenities create a welcoming outdoor living environment to

Jack Winter Cascade Hasson Sotheby's International Realty

$1,449,000
- 4 Beds
- 3.5 Baths
- 4,140 Sq Ft
930 NW Highland Dr

Waldport, OR
Perched in the coveted Alsea Highlands above the coastal tsunami zone, this extraordinaryVictorian estate captures sweeping, panoramic views of Alsea Bay, the iconic Alsea Bay Bridge, and the endless blue horizon of the Pacific Ocean. Set on .41 acres of meticulously curated grounds, this is a rare blend of architectural elegance and coastal serenity.Expertly crafted by Carlson Builders, the

Jack Winter Cascade Hasson Sotheby's International Realty

$750,000
- Land
- 0.27 Acre
- $2,777,778 per Acre
TL 8800 SW Cupola Dr

Newport, OR
This oceanfront lot is shovel ready for your dream home on the beach in the private, gated Southshore community in the South Beach area of Newport Oregon. The building site offers a spectacular 180-degree vantage point of white-water ocean surf, dunes and beach. The property also has northerly views of the Newport jetty and Yaquina Head lighthouse. The lot is fully developed with all utilities

Jack Winter Cascade Hasson Sotheby's International Realty

$250,000
- Land
- 0.17 Acre
- $1,470,588 per Acre
TL 7000 SW Cupola Dr

Newport, OR
This lot is located close to the Clubhouse and beach access paths are only a few steps away. Southshore's 80 acres features a variety of cape-code style single family homes and condominiums in a gated community. This beachside neighborhood features private beach access, recreational facilities including indoor pool/spa, sauna and steam rooms, exercise room, indoor/outdoor tennis and pickleball,

Jack Winter Cascade Hasson Sotheby's International Realty

Recently Sold

$965,000

Sold Jan 5, 2026
- 3 Beds
- 2 Baths
- 2,303 Sq Ft
175 SW 59th St

South Beach, OR
- 1% Below List
- 47 Days On Market
- $419/SF
- Current Est. Value $914K
Jack Winter Cascade Hasson Sotheby's International Realty

$735,000

Sold Jul 31, 2025
- 3 Beds
- 2 Baths
- 1,683 Sq Ft
5940 SW Arbor Dr

Newport, OR
- 2 Days On Market
- $437/SF
- Current Est. Value $732K
Jack Winter Cascade Hasson Sotheby's International Realty

$820,000

Sold Jun 13, 2025
- 2 Beds
- 2 Baths
- 1,697 Sq Ft
5956 SW Cupola Dr

South Beach, OR
- 6% Below List
- 115 Days On Market
- $483/SF
- Current Est. Value $891K
Jack Winter Cascade Hasson Sotheby's International Realty

$1,823,000

Sold Feb 20, 2025
- 3 Beds
- 3 Baths
- 2,399 Sq Ft
8566 NW Coast Rd

Seal Rock, OR
- 8% Below List
- $760/SF
- Current Est. Value $2M
Jack Winter Cascade Hasson Sotheby's International Realty

$815,000

Sold Nov 22, 2024
- 2 Beds
- 2 Baths
- 2,003 Sq Ft
5705 SW Barnacle Ct

South Beach, OR
- 2% Below List
- 110 Days On Market
- $407/SF
- Current Est. Value $828K
Jack Winter Cascade Hasson Sotheby's International Realty

$855,000

Sold Jun 24, 2024
- 4 Beds
- 3 Baths
- 2,656 Sq Ft
5780 SW Barnacle Ct

South Beach, OR
- 5% Below List
- 74 Days On Market
- $322/SF
- Current Est. Value $893K
Jack Winter Cascade Hasson Sotheby's International Realty

$1,050,000

Sold May 3, 2024
- 4 Beds
- 4 Baths
- 3,080 Sq Ft
1034 SE 1st St

Newport, OR
- 12% Below List
- 124 Days On Market
- $341/SF
- Current Est. Value $1M
Jack Winter Cascade Hasson Sotheby's International Realty

$843,500

Sold Apr 18, 2024
- 3 Beds
- 3 Baths
- 2,279 Sq Ft
5730 SW Barnacle Ct

South Beach, OR
- 3% Below List
- 16 Days On Market
- $370/SF
- Current Est. Value $874K
Jack Winter Cascade Hasson Sotheby's International Realty

$235,000

Sold Mar 22, 2024
- Land
- 1.29 Acres Lot
0 SW 68th Dr

Unit 24070511

South Beach, OR
- 24% Below List
- 43 Days On Market
Jack Winter Cascade Hasson Sotheby's International Realty

Other Experience

Luxury Homes, Residential, Waterfront, Vacant Land, Condos & Co-ops

Agent License: Oregon #201226178

Jack Winter

(541) 640-5396

Nearby Homes

Jack Winter

About Jack

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Areas Jack is Experienced In

Jack's Listings and Deals

Jack's Recent Active Listings

Recently Sold

Other Experience